Search results for \"naphthalene oxidation\". In naphthalene derivatives Organic chemistry

The simplest of the condensed benzenoid hydrocarbons is naphthalene:

Positions 1,4,5 and 8 are designated "α", positions 2, 3,6,7 are designated "β".

Methods of obtaining.

The bulk of naphthalene is obtained from coal tar.

In laboratory conditions, naphthalene can be obtained by passing benzene and acetylene vapors over charcoal:

Dehydrocyclization over platinum of benzene homologues with a side chain of four or more carbon atoms:

According to the reaction of diene synthesis of 1,3-butadiene with P-benzoquinone:

Naphthalene is a crystalline substance with T pl. 80 0 C, characterized by high volatility.

Naphthalene undergoes electrophilic substitution reactions more easily than benzene. In this case, the first substituent almost always becomes in the α-position:

The entry of an electrophilic agent into the β-position is observed less frequently. As a rule, this happens under specific conditions. In particular, the sulfonation of naphthalene at 60 0 C proceeds as a kinetically controlled process with the predominant formation of 1-naphthalene sulfonic acid. Sulfonation of naphthalene at 160 0 C proceeds as a thermodynamically controlled process and leads to the formation of 2-naphthalene sulfonic acid:

When a second substituent is introduced into a naphthalene molecule, the orientation is determined by the nature of the substituent already present in it. Electron-donating substituents located in the naphthalene molecule direct the attack to the same ring in the 2nd and 4th positions:

Electron-withdrawing substituents located in the naphthalene molecule direct the attack to another ring in the 5th and 8th positions:

Oxidation

Oxidation of naphthalene with atmospheric oxygen using vanadium pentoxide as a catalyst leads to the formation of phthalic anhydride:

Recovery

Naphthalene can be reduced by the action of various reducing agents with the addition of 1, 2 or 5 moles of hydrogen:

2.2. Anthracene, phenanthrene

By growing another ring from naphthalene, two isomeric hydrocarbons can be obtained - anthracene and phenanthrene:

Positions 1, 4, 5 and 8 are designated "α", positions 2, 3, 6 and 7 are designated "β", positions 9 and 10 are designated "γ" or "meso" - the middle position.

Methods of obtaining.

The bulk of anthracene is obtained from coal tar.

In laboratory conditions, anthracene is obtained by the Friedel-Crafts reaction from benzene or with tetrabromoethane:

or by reaction with phthalic anhydride:

The reaction produces anthraquinone, which is easily reduced to anthracene. For example, sodium borohydride:

The Fittig reaction is also used, by which an anthracene molecule is obtained from two molecules ortho-bromobenzyl bromide:

Properties:

Anthracene is a crystalline substance with T pl. 213 0 C. All three benzene rings of anthracene lie in the same plane.

Anthracene easily adds hydrogen, bromine and maleic anhydride to positions 9 and 10:

The product of bromine addition easily loses hydrogen bromide to form 9-bromomanthracene.

Under the influence of oxidizing agents, anthracene is easily oxidized to anthraquinone:

Phenanthrene, like anthracene, is a component of coal tar.

Just like anthracene, phenanthrene adds hydrogen and bromine to the 9,10-position:

Under the influence of oxidizing agents, phenanthrene is easily oxidized to phenanthrenequinone, which is further oxidized to 2,2'-biphenic acid:

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General chemical technology "Production of sulfuric acid. Computer modeling" method. instructions

The guidelines outline the theoretical foundations of the chemical production of sulfuric acid. The instructions are written in accordance with the requirements of the educational program of the State Educational Institution for Higher Education and are intended for students of non-technical specialties of universities.

Oxidation of sulfur dioxide …………………………24 3. 1 Physico-chemical basis of oxidation of sulfur dioxide …………………………...24<...>SO2 oxidation degree 95%.<...>Oxidation of sulfur dioxide 3.1 Physico-chemical basis of sulfur dioxide oxidation 3.1.1 Chemical equilibrium<...>4 Classify the oxidation reaction of sulfur dioxide. 5 How does temperature affect the equilibrium state of oxidation<...>Oxidation of dioxide 3.1 Physicochemical basis of sulfur dioxide oxidation 3.1.1 Chemical equilibrium

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TRANSFORMATION OF NAPHTHALEN AND DIMETHYLNAPHTHALINES BY BACTERIA OF THE GENUS PSEUDOMONAS ABSTRACT DIS. ... CANDIDATE OF BIOLOGICAL SCIENCES

M.: INSTITUTE OF MICROBIOLOGY

1. Study of the ability of representatives of soil microflora to use naphthalene as a source of carbon and energy; 2. Study of the ways of microbiological transformation of naphthalene and dimethylnaphthalenes; 3. Study of the possibility of obtaining compounds of practical value by microbiological transformation of naphthalene and dimethylnaphthalenes.

Adsorption of naphthalene oxidation products from the culture liquid was carried out using an anion exchange<...>The oxidation of naphthalene by isolated bacteria made it possible to divide the studied cultures into two groups.<...>liquid Naphthalene g/l Naphthalene oxidation products at points of maximum concentration Bacteria 1st<...>At the same time, no naphthalene oxidation products were found in the culture liquid.<...>Gentisic acid is a product of microbiological oxidation of naphthalene. Izv.

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The article presents the results of a series of experiments on the effect of high-viscosity oils on the oxygenase activity of native soil microflora. It has been shown that after an adaptation period, microorganisms adapt to the hydrocarbons of high-viscosity oils and the rate of biochemical oxidation increases. It was found that over 180 days of the experiment, the utilization of the studied oils ranged from 62 to 86%. Analysis of residual oil hydrocarbons using IR spectrometry showed the presence of a large number of oxygen-containing compounds, which are intermediate metabolic products during the microbiological oxidation of hydrocarbons (HC) of oil. Using chromatography-mass spectrometry (CMS), the ability of native soil microflora to biodegrade all petroleum hydrocarbons in a model soil system was demonstrated.

Using the GC-MS method, hydrocarbons such as alkanes, cycloalkanes, alkylbenzenes (AB), naphthalenes were identified in oils<...>These components are difficult to reach for microbiological oxidation.<...>4.13838 0.79541 Cycloalkanes 0.17546 0.00138 1.70736 0.07231 Alkylbenzenes 0.02356 0.00023 0.04627 0.00011 Naphthalene<...>5.56824 1.13323 Cyclohexanes 2.30779 0.70320 0.80732 0.12411 Alkylbenzenes 0.59821 0.00398 0.02415 0.00056 Naphthalene<...>Microbiological oxidation of naphthalenes was 65...75%, phenanthrene 57...73%, fluoranthenes 53...71%.

Organic chemistry textbook. allowance (for distance learning)

The textbook is compiled in accordance with the curriculum of the course “Organic Chemistry” for distance learning students in the specialties “Biology” and “Ecology” of the Faculty of Biology and Ecology of Yaroslavl State University. P.G. Demidova. It includes short lectures, tests for the organic chemistry course that students must complete independently, and descriptions of basic laboratory work.

Naphthalene is extracted from coal tar.<...>When naphthalene is oxidized, ortho-phthalic acid is obtained: [O] COOH COOH Naphthalene hydrogenation occurs<...>Write the reaction equations for the oxidation of naphthalene and anthracene. 20.<...>; b) p-dimethylbenzene; c) naphthalene?<...>Write the reaction equations for the oxidation of naphthalene. Option 28 1.

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Introduction to the course of organic chemistry. Technologies for obtaining carbon-containing nanomaterials, textbook. allowance

Publishing house of NSTU

The textbook is a course of lectures on organic chemistry for students majoring in Environmental Engineering. The manual examines general issues of organic chemistry: the basic principles of the structure of organic substances, types of isomerism, nomenclature of the main classes of organic compounds, types of chemical bonds, mechanisms and types of chemical reactions. The methods of preparation and physicochemical properties of the main classes of chemical compounds (alkanes, alkenes, alkadienes, alkynes, cycloalkanes, aromatic compounds, alcohols, aldehydes, ketones, amines, sugars and carbohydrates) are considered in detail. Methods of chemical technology for producing carbon-containing nanomaterials are described. The mechanisms of formation of carbon-containing materials and the scientific basis for regulating the processes of their formation are considered.

Oxidation reaction.<...>Evidence of the presence of two rings in naphthalene can be the reaction of its oxidation with chromic anhydride,<...>Naphthalene oxidation reaction.<...>When naphthalene is oxidized with oxygen in the presence of vanadium pentoxide, one ring is destroyed and<...>Oxidation of naphthalene and some of its derivatives leads to the destruction of the aromatic character of one

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ORGANIC CHEMISTRY Approved by the UMS OGPU as an educational and methodological aid for students in the field of preparation 03/44/05 Pedagogical education (with two profiles of training), profiles Biology and Chemistry in the discipline “Organic Chemistry”

The manual is intended for undergraduate students (profile “Biology and Chemistry”) studying organic chemistry in the 4th and 5th semesters. The manual includes a plan of laboratory and practical classes and instructions for laboratory work, test tasks and texts of tests, as well as questions for tests and exams, a list of recommended literature.

Oxidation of ketones.<...>Naphthalene. Anthracene, phenanthrene. 1. Naphthalene: production and structure. 2.<...>Chemical properties of naphthalene:  substitution reactions;  addition reactions;  oxidation reactions. 3.<...>Oxidation of naphthalene also occurs easily: for example, with chromium (VI) oxide in acetic acid.<...>The sulfonation and oxidation of anthracene proceeds similarly to that of naphthalene.

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Organic chemistry. Selected sections of textbooks. allowance

Publishing house of NSTU

The textbook contains theoretical material on the main sections of organic chemistry, which is difficult for students to study, learning tasks, as well as tasks for independent work and questions for self-control.

aromatic hydrocarbons increases in the series: benzene  naphthalene  anthracene.<...>naphthalene, depending on the conditions, either phthalic anhydride or 1,4-naphthoquinone is obtained.<...>C O C O O O O 1,4 NaphthoquinoneNaphthalenePhthalic anhydride O2/V2O5 CrO3/CH3COOH Phthalic anhydride Naphthalene<...>O CH3 O O Toluene 3,4 oxide Naphthalene 1,2 oxide Benzanthracene epoxide (benzanthracene -5,6 oxide) Toluene<...>proceeds stepwise: Naphthalene 1,4 Dihydronaphthalene Tetralin Decalin 2H 2H 6H Naphthalene 1, 4 – Dihydronaphthalene

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Organic chemistry. Part V, VI textbook. allowance

M.: Prometheus Publishing House

This publication represents parts V and VI of the textbook for the course “Organic Chemistry”. It covers compounds of the cyclic series and includes modern data on the nomenclature and isomerism, electronic structure, methods of preparation and characteristic chemical properties of the class of alicyclic hydrocarbons (cycloalkanes), aromatic compounds, including the benzene series, polynuclear aromatic hydrocarbons with isolated and fused nuclei, as well as heterocyclic compounds with one or more heteroatoms in the ring. Properties are considered in close connection with the structure of organic compounds. Considerable attention is paid to reaction mechanisms that explain the characteristics of chemical behavior. The presentation of the material is accompanied by illustrations of the biological role of organic substances of the corresponding class. At the end of each section there is a list of questions and tasks for repetition and consolidation of the material.

<...> <...> <...>Compare the conditions for the oxidation of one of the nuclei of naphthalene and benzene. Give reaction equations. 13.<...>Oxidation and reduction Oxidation.

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No. 1 [Bulletin of Tomsk State University. Chemistry, 2017]

The journal is a specialized periodical scientific publication. Split into an independent periodical from the general scientific journal “Bulletin of Tomsk State University” in 2014. “Bulletin of Tomsk State University. Chemistry" is the first specialized journal in chemistry in Tomsk and is aimed at increasing the publication activity of research staff at universities in the Tomsk region and beyond. Main sections of the journal: Synthesis and properties of substances and materials Physico-chemical laws of processes, structure and properties of compounds Theoretical and applied issues of analytical chemistry Chemical technology Biochemical properties of inorganic and organic compounds

Fluorescence spectra of naphthalene in the presence of HS and HMC (g/l): 1 – pure naphthalene; 2 – 4×10–2; 3 – 3.2<...>Fluorescence spectra of HS and SMC (C = 10–2 g/l): a – in the absence of naphthalene; b – in the presence of naphthalene<...>Interaction of a HS fragment with naphthalene (stacking interaction) Naphthalene interacts to a lesser extent<...>Synthesis of HA by oxidation of GO. The reactor is filled to no more than half its volume.<...>We processed real mixtures of GO oxidation products.

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Organic chemistry. [At 6 o'clock]. Parts I, II; Parts III, IV; Part V, VI [set] textbook. allowance

This publication consists of three books (parts I – VI) of a textbook for the course “Organic Chemistry”. The first book (parts I and II) includes updated content covering all major classes of acyclic hydrocarbons of the alpha series. The second book covers the main classes of functional (Part III) and heterofunctional (Part IV) derivatives of aliphatic hydrocarbons. Parts V and VI of the textbook cover compounds of the cyclic series and include modern data on nomenclature and isomerism, electronic structure, methods of preparation and characteristic chemical properties of the class of alicyclic hydrocarbons (cycloalkanes), aromatic compounds, as well as heterocyclic compounds with one or more heteroatoms in the ring.

Phthalic acid is produced by the oxidation of naphthalene.<...>Due to the symmetry of the naphthalene molecule, it forms two series of monosubstituted: For disubstituted naphthalenes<...>Nitration of naphthalene leads to the formation of α-nitronaphthalene, upon subsequent oxidation of which we obtain<...>Homologues of naphthalene, when exposed to sodium dichromate in a neutral environment, undergo oxidation at alkyl<...>Compare the conditions for the oxidation of one of the nuclei of naphthalene and benzene. Give reaction equations. 13.

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The article provides data on the preparation and use of aqueous solutions of peracetic acid (PAA). A significant part of the article is devoted to NAA stabilizers and their mechanism of action. A comparative analysis of the effectiveness of various stabilizers was carried out and the kinetic parameters of the process of obtaining aqueous solutions of NAA, which can be used in designing the industrial production of disinfectants based on it, were considered.

It is based on the oxidation reaction of acetic acid (AA) with aqueous solutions of hydrogen peroxide (HP): (<...>Kinetic patterns of liquid-phase oxidation of acetic acid with hydrogen peroxide in the presence<...>In Fig. Figure 3 shows the kinetic curves of UA accumulation during the liquid-phase oxidation of UA with hydrogen peroxide<...>Oxidation of naphthalenes to quinones with peracetic acid. Candidate's dissertation, M., MHTI, 1985. 3.<...>Chain reactions of hydrocarbon oxidation, 1965. 18. Shmid R., Sapunov V.N. Informal kinetics.

Using the methods of IR spectrometry and gas chromatography-mass spectrometry, the processes of biooxidation of oil hydrocarbons were studied and the most significant bioindicators characterizing the activity of biodestructive processes in the conditions of deep wells of the Vakhskoye field were determined.

Monoaromatic (alkylbenzenes), biaromatic (naphthalenes, fluorenes), triaromatic have been identified<...>analysis, the maximum changes in the process of oil biotransformation occurred in the content of alkylbenzenes and naphthalenes<...>Scanning for fragment ions of alkylbenzenes m/z 92, naphthalenes m/z 142, 156, 170, 184, phenanthrene<...>The aromatic rings of alkylbenzenes, naphthalenes, their substitutes, as well as anthracene and phenanthrene are cleaved<...>Mass fragmentogram of the distribution of n-alkylbenzenes (m/z 92) (A), naphthalenes (m/z 142, 156, 170, 184)

Intensification of ethylene production processes using the example of OAO Nizhnekamskneftekhim, abstract. dis. ...cand. tech. sciences

The presented dissertation work is devoted to the development of a set of measures to intensify the processes occurring in an ethylene plant, which includes: increasing the flexibility of the pyrolysis unit for raw materials by involving the gas separation unit in the processing of secondary streams; development of technologies for neutralizing wastewater from an ethylene plant and processing liquid secondary streams into target products.

Oxidation conditions were determined: air flow 415-420 kg/h, oxidation time 1.52.5 hours, dosage<...>technological diagram of the hydrodealkylation unit with a vacuum column (Fig. 7), with the release of commercial naphthalene<...>Vacuum column for separating biphenyl and naphthalene from the bottom product of the resin column.<...>resin separation 35 28 High purity biphenyl for benzene production plant or naphthalene as a commercial product<...>Methylnaphthalenes 82.55 5.51 82.43 39.44 0.12 0.01 Diphenyl 1282.64 85.51 6.63 3.17 1276.01 98.84 Naphthalene

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Intensification of wastewater treatment from chemical industries from hydrocarbons using oxidative methods. dis. ...cand. tech. sciences

The presented dissertation work is devoted to determining effective conditions for the implementation of wastewater treatment from chemical industries from hydrocarbons using oxidative methods.

In addition, compounds such as 1,3,5,7-cyclooctatetraene (2.1%), tridecane (2.1%), naphthalene were found in wastewater<...>benzene (51.4%), 4,7-dimethylindene (7.5%), toluene (5.4%), styrene (5.4%), as well as compounds such as naphthalene<...>The main components of chemically contaminated ethane pyrolysis wastewater are benzene (15.4%), naphthalene<...>treatment of wastewater OVS, such compounds as 1,3,5,7-cyclooctatetraene, tridecane, naphthalene disappeared from its composition<...>9-hexadecenoic acid ester (0.34%), 9-hexadecenoic acid octadecyl ester (0.11%), decanal, naphthalene

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CONCENTRATION OF ZN, SI, CO AND MO WITH ORGANIC CO-PRECIDIENTS IN THE ANALYSIS OF SOILS, PLANTS AND NATURAL WATER ABSTRACT DIS. ... CANDIDATE OF AGRICULTURAL SCIENCES

ALL-UNION ORDER OF LENIN ACADEMY OF AGRICULTURAL SCIENCES NAMED AFTER V. I. LENIN

The objective of this study was to develop methods for concentrating microelements during their determination in soils, plants and natural waters.

eutectic mixture of diphenylamine wt %) and naphthalene (36.4 wt %) diphenylamine naphthalene eutectic<...>mixture of diphenylamine and linen diphenylamine naphthalene eutectic mixture of diphenylamine and linen i (63.6 naphthanaphthaCo<...>Co-precipitation of molybdenum with tannin with “oxidized” Stenhouse dye makes it possible to determine the mobile<...>Elements are effectively coprecipitated with a mixture of diphenylamine and naphthalene. 2.<...>It was established that the ashless organic co-precipitant “oxidized” Stenhouse dye together with tannin

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Tests in organic chemistry, part I method. instructions

This work represents test assignments in organic chemistry on the topic “Hydrocarbons” for distance learning students. It can also be used for independent work and as milestone tests for full-time students of technological specialties.

Give schemes for the production of naphthalene from benzene and acetylene and its sulfonation at 160ºС, followed by<...>Write the following reactions for naphthalene: a) nitration, b) halogenation.<...>Write the following reactions for naphthalene: a) oxidation with chromic anhydride, b) nitration, and then oxidation<...>Indicate all stages of obtaining naphthalene from benzene and acetylene.<...>Write the reactions of naphthalene nitration followed by chlorination of the nitration product 7.

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No. 1 [Petrochemistry, 2017]

The chromium atoms were assigned an oxidation state of II.<...> <...>In this case, the conversion of naphthalene is 100% with a yield of decalins of 82%.<...>Among olefin oxidation processes, cyclohexene oxidation is still the object of intensive research.<...>) and the proportion of enol (less oxidized form) decreased.

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RESEARCH OF WATER PLANT-MICROBIAL ASSOCIATION IN CONDITIONS OF OIL POLLUTION ABSTRACT DIS. ... CANDIDATE OF BIOLOGICAL SCIENCES

The purpose of the work is to study the destructive and associative potential of the aquatic plant-microbial community formed by Elodea canada to identify its role in the processes of self-purification of water bodies from oil. In achieving this goal, the following tasks were solved: 1. Assess the mutual influence of Elodea canada, aquatic microorganisms and oil hydrocarbons. 2. Isolate and examine periphyton bacteria. 3. Determine the destructive potential of the plant-microbial association and its individual components in relation to oil hydrocarbons. 4. Determine the contribution of Elodea enzyme systems to the destruction of pollutants. 5. Investigate individual associative characteristics of the components of the aquatic plant-microbial community formed by Elodea canada.

Naphthalene and phenanthrene were studied as representatives of PAHs.<...>Destructive activity of extract (pH 8.2) and exudates of elodea Activity of elodea enzymes responsible for oxidation<...>min/mg protein), tyrosinase (0.12-0.78 µmol/min/mg protein) and peroxidase activity (1.02-4.11 for oxidation<...>In addition, it has been shown that Elodea has both oxidase and peroxidase mechanisms for the oxidation of catechol.<...>The plant was able to oxidize phenol, toluene, benzene and naphthalene.

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The generation of superoxide anion by oil-oxidizing microorganisms of two strains of the species Acinetobacter calcoaceticus was studied using the lucigenin-activated chemiluminescence method. It was shown that both strains of this microorganism produced superoxide anion when incubated with certain hydrocarbons. The most active generation of superoxide anion in bacteria was caused by diesel fuel and naphthalene

The most active generation of superoxide anion in bacteria was caused by diesel fuel and naphthalene.<...>the hypothesis received experimental confirmation during a series of experiments on inhibition of oxidation<...>Individual hydrocarbons (pentane, decane, hexadecane (HD), benzene, naphthalene,<...>the mechanism of generation of superoxide anion radical is triggered, which confirms the possibility of non-enzymatic oxidation<...>The role of free radical oxidation in the processes of microbiological transformation of oil / I.S.

The spectral (1H NMR, IR), optical and voltammetric characteristics of complexes of Pd(II), Pt(II), Rh(III), Ir(III) with ethylenediamine and metalated azole phosphors – 2-phenylbenzoxazole, 2-phenylbenzothiazole, 2, 5-diphenyloxazole, 2-[(1,1"-biphenyl)-4-yl]-5-phenyloxazole, 2-(naphthalene-1-yl)benzothiazole. The difference in the spectroscopic parameters of the complexes is due to an increase in the efficiency of donor-acceptor interaction with ligands Pt(II), Ir(III) compared with Pd(II), Rh(III). There is a correlation between the energy of the metal–ligand charge transfer bands and the potential difference of one-electron processes of oxidation and reduction of the complexes. Quenching of fluorescence of metalated azoles and phosphorescence of complexes in the visible regions from the metal-modified intra-ligand excited state are associated with an increase in the efficiency of singlet-triplet conversion as a result of the spin-orbit interaction of platinum metals.

phenylbenzoxazole, 2-phenylbenzothiazole, 2,5-diphenyloxazole, 2-[(1,1"-biphenyl)-4-yl]-5-phenyloxazole, 2-(naphthalene<...>phenylbenzothiazole (Hbt), 2,5diphenyloxazole (Hpo), 2-[(1,1"-biphenyl)-4-yl]-5phenyloxazole (Hbpo), 2-(naphthalene<...>Oxidation of azole phosphors occurs at a potential > 2 V.<...>Platinum(II) hexafluorophosphate (ethylenediamine).<...>Bis(ethylenediamine)iridium(III) hexafluorophosphate.

No. 4 [Petrochemistry, 2017]

Founded in 1961. Published original articles and reviews of theoretical and experimental research on the problems of chemistry and geochemistry of oil, oil and gas refining, including deep oil refining, processes and catalysts for petrochemical processes, issues of obtaining new oil products, including lubricants and additives, and environmental protection. The journal is peer-reviewed and included in the List of Higher Attestation Commissions.

Than naphthalene and phenanthrene.<...> <...>Compared to MPF-NiWS catalysts, naphthalene conversion in Table 1.<...>The main product of naphthalene hydrogenation in all cases is tetralin.<...>naphthalene levels increases.

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No. 4 [Kinetics and catalysis, 2017]

Key words: oxidation of dodecyl mercaptan, kinetic patterns of thiol oxidation, immobilized<...>A different pattern was observed in the naphthalene HID reaction (Fig. 1.<...>Catalyst Conversion, % k × 104, mol g–1 h–1 SGID/OS*τ = 0.06 h τ = 0.02 h DBT naphthalene DBT naphthalene<...>A similar approach was used to estimate the rate of naphthalene HID.<...>Catalyst GDS DBT HYD naphthalene n Kads. DK, kPa–1 R2 n Kads.

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Organic chemistry. At 4 p.m. Part 2 tutorial

M.: Knowledge Laboratory

The textbook systematically describes organic compounds by class, and also outlines the basic theoretical principles of organic chemistry. The structure and properties of organic compounds are considered from the standpoint of both the theory of electronic displacements and the theory of molecular orbitals. The second part includes chapters on stereochemistry, nucleophilic substitution and elimination reactions, as well as the chemistry of alcohols, thiols, ethers and sulfides, free radicals, and the concept of aromaticity is introduced.

And also about the greater stability of naphthalene compared to benzene.<...> <...>Substituted naphthalenes behave similarly to benzene derivatives.<...>The oxidation of naphthalene with potassium permanganate in an alkaline medium is accompanied by the destruction of one aromatic<...>Substituted naphthalenes behave similarly to benzene derivatives.

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Laboratory workshop on organic chemistry method. instructions

The guidelines are written in accordance with the requirements of the FGP educational program. The guidelines for the laboratory workshop in organic chemistry outline methods and techniques for working with organic substances, laboratory glassware and materials, determination of the most important constants, and qualitative analysis of the elemental composition of organic compounds and their functional groups. The guidelines consist of nineteen works on the synthesis of organic compounds. Each laboratory work consists of a brief theoretical presentation of the material, a description of the experiments, and ends with control questions that the student must answer.

Sublimation / Sublimation / Reagents and equipment: Naphthalene, or technical phthalic anhydride 1.0 g; technochemical<...>According to the literature, naphthalene has a melting point of 80 °C, phthalic anhydride 130.8 °C. 5.4 Experience<...>substances are experimentally determined by cryoscopy using benzene and naphthalene as a solvent<...>then double the amount of alkali metal is used, or the substances under study are impregnated with naphthalene for nitrogen<...>naphthalene?

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Methods for obtaining organic compounds, textbook. allowance

Methods for obtaining the main classes of organic compounds and some of their derivatives are considered. Each section is equipped with a large number of problems of varying degrees of difficulty, so that students of different levels of preparedness for studying organic chemistry can use the manual. At the end of the manual, answers to problems are given that will allow you to understand the logic of solving problems and check the correctness of their solution. The manual is aimed at independent study of the subject.

Naphthalene, phenol, and quinoline are isolated from medium oil.<...>, as one of the important stages in the production of naphthalene and its trisubstituted derivatives according to Haworth.<...>Oxidation of isopropylbenzene.<...>Preparation methods based on oxidation reactions a) Oxidation and dehydrogenation of alcohols.<...>Oxidation of aromatic hydrocarbons Benzene and naphthalene under harsh conditions and in the presence of pentoxide

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STUDY OF YEAST GLYCERAL DEHYDE-3-PHOSPHATE DEHYDROGENASE ABSTRACT DIS. ... CANDIDATE OF BIOLOGICAL SCIENCES

M.: MOSCOW STATE UNIVERSITY NAMED AFTER M.V. LOMONOSOV

The purpose of this work is to further study the issue of interaction of the cofactor with GAPDH. The following tasks were set in the work: 1) to find out the role of individual fragments of NAD in its binding to protein. 2) To characterize the areas of the surface of the protein molecule involved in the binding of the coenzyme, study the interaction of GAPDH with a hydrophobic compound (1-anilino 8-naphthalene sulfonate, ANS) and find out whether the place of fixation of this fluorescent sample is related to the zone of the active center of the dehydrogenase.

Dependence of the reaction rate of PHA oxidation on pH in Tris-HCI buffer at different ionic strengths.<...>Effect of Nad on the kinetics of the PHA oxidation reaction.<...>Effect of phosphate on the kinetics of the FGD oxidation reaction.<...>A simplified scheme according to which PHA oxidation occurs can be represented as follows: E"HA#*+ PHA<...>Combined inhibition of GAPDH activity by 1-anilino8-naphthalene-sulfonate and ADP.

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Structure and properties of hydrocarbons Guidelines

Ivanovo State University of Chemical Technology

The guidelines were developed as a course of lectures on the discipline Organic chemistry and fundamentals of biochemistry (part I, hydrocarbons) for correspondence students at ISUTU studying in specialties 240202 Chemical technology and equipment for finishing production, 240201 - Technology and equipment for the production of chemical fibers and composite materials based on them and 240501 Chemical technology of macromolecular compounds (HTMC), include tasks for test No. 1 and recommendations for its implementation.

Name the oxidation products. 19.<...>Oxidation reactions When alkynes are oxidized with ozone or KMnO4 at pH=7, they are formed that are less stable for further<...>oxidation of α,α-diketones R-CO-CO-R. 7.<...>Oxidation reactions.<...>Naphthalene (n=2) colorless crystals.

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Laboratory workshop on organic chemistry. allowance

The textbook outlines methods and techniques for working with organic substances and materials. Definitions of the most important constants, a qualitative analysis of the elemental composition of organic substances and their functional groups are given. Each laboratory work consists of brief theoretical material, descriptions of experiments and ends with control questions that the student must answer.

Sublimation is used for the purification of quinones, naphthalene, and polynuclear hydrocarbons; organic acids<...>According to the literature, naphthalene has a melting point of 80 °C, phthalic anhydride 130.8 °C.<...>Alkenes are easily oxidized.<...>Oxidation reactions Oxidation is the process of losing electrons, for example: Fe+2  Fe+3 + eAs<...>What compound is formed during the oxidation of naphthalene?

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No. 4 [Journal of the Siberian Federal University. Chemistry. Journal of Siberian Federal University/ Chemistry, 2011]

The “Chemistry” series is multidisciplinary in terms of the published results of fundamental and applied research. However, preference is given to works devoted to the chemical aspects of environmental management. The high relevance of this topic is due to the presence of huge resources of natural, mineral and organic raw materials in the Siberian region. New technologies for chemical processing of these resources into popular products (precious and non-ferrous metals, motor fuels, cellulose, etc.) must not only be cost-effective, but also ensure minimal damage to the environment and human health.

Naphthalene, tetralin and decalin were investigated as solvents.<...>Under the conditions of the hydrogenation process, tetralin is dehydrogenated, turning into 59-71 wt. % in naphthalene.<...>In the absence of catalysts and coal, these naphthalene conversion products were not detected.<...>Indicators of brown coal hydrogenation in the environment of naphthalene and decalin Catalyst Degree of WMD conversion,<...>in a naphthalene environment, the ratio of coal: naphthalene = 1:1 wt. parts Without catalyst 37.3 13.4 8.7 ≈ 0.1

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M.: PROMEDIA

The electrochemical behavior of silver and the SrM925 alloy in solutions containing an organic compound with two sulfide groups was studied. It has been established that when silver and CrM925 alloy are processed in the studied environments, passivating layers are formed on the metal surface, providing protection against darkening.

sparingly soluble compounds with organic compounds containing sulfur in their structure in the oxidation state<...>Photoelectrochemical properties of surface layers formed on titanium by anodic oxidation<...>Lyubimov QUANTUM-CHEMICAL ASSESSMENT OF ELASTIC PROPERTIES OF NAPHTHALEN MOLECULES UNDER EXTENTION (Yaroslavl State<...> [email protected] The deformation curves of the naphthalene molecule were calculated using the quantum chemical method DFT B3LYP/6-31G*<...>Keywords: nanotubes, naphthalene, deformation, quantum chemical calculation, vibrations, destruction Modeling

In four oils from the north of Western Siberia, the composition of saturated and aromatic hydrocarbons was studied, and the structural and group characteristics of resins and asphaltenes were determined. Cenomanian oils (deposits of layers PK, K2c) of the Russkoye, Barsukovskoye and Pangodinskoye fields, according to information on the distribution of hydrocarbons, are naphthenic, and the Pangodinskaya sample from the Lower Cretaceous reservoir (layer BN9) is methane. Features of the hydrocarbon composition of the saturated fraction and the characteristics of heterocyclic components indicate the formation of the studied oils in the conditions of the main oil formation zone from dispersed organic matter of mixed genesis. Consequently, the source deposits are submerged to depths that significantly exceed the current position of the deposits of the studied oils. Secondary (crypto-hypergene: oxidation and biodegradation) changes in shallow oils determined their modern predominantly naphthenic composition, significantly complicating the reconstruction of the types of original dispersed organic matter. It is assumed that the mixed genotype of the studied oils is due not only to their heterogeneous source, but also to the processes of reformation of primary oil deposits during the Cenozoic stage of tectogenesis. Cenomanian Russian and Pangodinskaya naphthenic oils are enriched with adamantoids, which can selectively accumulate during biodegradation

Secondary (crypto-hypergene: oxidation and biodegradation) changes in shallow oils determined<...>Naphthalene, methylnaphthalenes, and isomers of trimethylnaphthalenes were identified in the fraction of biaromatic hydrocarbons<...>In Pangodinskaya oils, alkylnaphthalenes are arranged in the following concentration series: di> mono> trimethylnaphthalenes > naphthalene<...>The content of methylnaphthalenes in this oil is higher than the content of naphthalene and dimethylnaphthalenes.<...>MF + 9-MF) 1.15 1.22 » 1.38 MP�-3 = (2+ 3-MF)/(9+ 1-MF) 0.76 0.81 » 0.92 Note: nf – naphthalene

No. 10 [Agrochemistry, 2018]

The topics of the articles published in the journal indicate the integral nature of the problems of agrochemistry. The journal publishes the results of fundamental studies of soil fertility with long-term use of fertilizers, the influence of chemical agents on the biological activity of soils, physiological and biochemical aspects of optimizing the mineral nutrition of plants, the use of fertilizers, growth regulators, and pesticides. The issues of plant resistance to abiotic environmental factors and agroecological aspects of the use of genetically modified crops are considered. Much attention is currently paid to the issues of agroecology and ecotoxicology. The journal presents works on research into the consequences of global climate change; reducing the toxicity of soils contaminated with heavy metals, pesticides, and petroleum products; methods are proposed to increase plant resistance to adverse environmental factors.

Several pathways for the transformation of PAHs are possible: chemical oxidation with oxygen, photo-oxidation, leaching<...>putida 53a, a variant was obtained characterized by the accumulation of catechol (one of the products of incomplete oxidation<...>naphthalene).<...>inoculation of mustard seeds with the P. fluorescens strain Pf-5(NPL-41) containing the NPL-41 plasmid with an incomplete oxidation pathway<...>Naphthalene (1 g/kg) or a mixture of PAHs (naphthalene 1 g/kg and phenanthrene) were added as organic pollutants

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No. 5 [Journal of Physical Chemistry, 2017]

The journal publishes theoretical and experimental works devoted to issues of chemical thermodynamics and thermochemistry, biophysical chemistry, photochemistry and magnetochemistry, structure of materials, quantum chemistry, physical chemistry of nanomaterials and solutions, surface phenomena and adsorption, methods and instrumentation of physical and chemical research.

The propane oxidation reaction was carried out at temperatures of 450 and 500°C.<...>In these systems, the reaction of complete oxidation of propane occurs with the formation of CO2 and H2O.<...>organic compounds, in the oxidation of CO, as well as in other processes.<...>Raw materials – 8% naphthalene solution in decane.<...>in OWCNT, an 8% solution of naphthalene in decane was used.

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No. 4 [Oil and gas chemistry, 2017]

The purpose of publishing the journal is to reflect the scientific and technical achievements of specialists from around the world in the fields of oil and gas refining, petrochemicals and gas chemistry, representing a single interconnected petrochemical complex. The editorial board of the journal “Petroleum and Gas Chemistry” aims to strengthen the connection between science and production, to create a platform where scientists and representatives of manufacturing companies in the industry can exchange best practices.

them and thereby breaking the oxidation chain or limiting its development.<...>The acid number of the oil before oxidation is 0.4.<...>When considering the state of mixing of two systems (molecules) naphthalene - 4-methylhexadecane at constant<...>Naphthalene 96.910 97.505 81.96 73.070 3.<...>Naphthalene 5.802 0.0004 3.

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Physical and colloidal chemistry

VSU Publishing House

The manual includes laboratory work on the most important sections of physical and colloidal chemistry (chemical thermodynamics, phase equilibria, electrochemistry, physical chemistry of disperse systems), performed at the educational and laboratory complex (ULC) “Chemistry”.

The melting point of diphenylamine (C6H5)2NH is 54–55 oC, naphthalene C10H8 is 80 oC.<...>Reduction and oxidation reactions in a galvanic cell occur at different electrodes, that is<...>The electrode at which oxidation occurs is called the anode; electrode where reduction occurs<...>Electrons formed during the oxidation process at the anode move along the external circuit to the cathode, participating<...>E is calculated using the Nernst equation: d Ox a a nF RTEE Re ln+°= , (3.14) where aOx and aRed are the activities of the oxidized

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Organic chemistry of fuels, textbook. allowance

Sib. federal university

Brief information on the structure, preparation, properties and application of all considered classes of compounds is presented. Laboratory work is presented with a description of the experimental part, safety rules, equipment, as well as tasks and questions for self-control.

Oxidation.<...>Oxidation.<...>Arenes (except benzene, naphthalene and other hononuclear homologues) readily undergo oxidation reactions.<...>The most resistant to oxidation by atmospheric oxygen are benzene and naphthalene.<...>The most important are benzene, toluene, xylenes, ethylbenzene, naphthalene. 2.10.

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BIOSENSORS FOR DETECTION OF SULFOAROMATIC AND PHENOLIC COMPOUNDS BASED ON BACTERIA OF THE GENERUS COMAMONAS AND PSEUDOMONAS - DESTRUCTORS OF I-TOLUENESULPHONATE AND PHENOL ABSTRACT DIS. ... CANDIDATE OF BIOLOGICAL SCIENCES

INSTITUTE OF BIOCHEMISTRY AND PHYSIOLOGY OF PLANTS AND MICROORGANISMS RUSSIAN ACADEMY OF SCIENCES

Purpose of the study. The goal of the work was to create electrochemical-type biosensors for the detection of sulfoaromatic and phenolic compounds based on bacteria of the genera Comamonas and Pseudomonas, which are destructors of l-toluenesulfonate, as a representative of sulfoaromatic compounds, and phenol, respectively.

Assessment of the stoichiometry of the TC oxidation process by cells.<...>Individual strains were tested for their ability to grow on individual oil component substrates: naphthalene<...>, 2methyl naphthalene, phenanthrene, hexadecane, m-cresol, phenol and a number of others.<...>along the meta-pathway and oxidation of the resulting catechol to pyruvic acid.<...>ethanol, 3-glycerol, 4-sorbitol, 5-sorbose, 6-xylose, 7-butanol, 8-isopropanol, 9-glucose, 10-catechol, 11-naphthalene

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For the first time, a method has been studied for the in situ preparation of unsupported nickel-tungsten sulfide catalysts for hydrodearomatization by decomposition of non-aqueous emulsions of solutions of various precursors in dimethyl sulfoxide (DMSO) in a hydrocarbon medium, stabilized by the surfactant SPAN-80. Ammonium thiotungstate (NH4)2WS4 and nickel thiotungstate 1-butyl-1-methylpiperidinium 2Ni2 were used as precursors. Nickel nitrate hexahydrate was chosen as a source of nickel. The resulting nickel-tungsten catalysts were characterized by TEM and XPS. The catalytic activity of Ni–W particles obtained in situ was studied in the hydrogenation reaction of naphthalene in the temperature range of 350–400°C and a hydrogen pressure of 5.0 MPa.

A 10% solution of naphthalene in n-hexadecane was used as a hydrocarbon medium.<...>The molar ratios of hydrogen/substrate were 60/1, naphthalene/W – 105/1.<...>1.5 98.5 30 Reaction conditions: 350°С, 5.0 MPa H2, 10 h, W/naphthalene = 1/105 Fig. 1.<...>As precursors (NH4)2WS4 and Ni(NO3)2, a catalyst is formed, on the surface of which sulfur in the oxidation state<...>In this case, the conversion of naphthalene is 100% with a yield of decalins of 82%.

Experimental studies have been carried out on the biodegradation of aromatic compounds of light oil from the Vakh field, which pollutes the soil at a concentration of 50 g/kg. Biodestruction was carried out for 30 days by natural soil microflora and microflora activated by a composition solution containing surfactants, nitrogenous substrate and phosphates. Using chromatography-mass spectrometry, it was established that the maximum changes in the composition of aromatic hydrocarbons were observed in oil after biodegradation by activated soil microflora. It has been established that monoarenes, biarenes and triarenes are most susceptible to biodegradation. In the composition of arenes, unsubstituted homologues are eliminated first, and then their methyl- and dimethyl-substituted ones. Minimal changes were noted for tetraarenes. Key words: soil microflora; biodestruction; aromatic petroleum hydrocarbons; nutrient substrate.

The main enzymes that catalyze the oxidation of hydrocarbons are catalase and dehydrogenase<...>They are represented by derivatives of naphthalene and fluorene (Fig. 2).<...>The following aromatic compounds of a number of naphthalenes have been identified: naphthalene (N), its methyl (MH), dimethyl<...>In the oil extracted from the typical variant, there is no unsubstituted naphthalene, its methyl substituted<...>Mass fragmentogram of the distribution of naphthalenes (m/z 142, 156, 170, 184) (A) and fluorenes (m/z 166, 180,

No. 5 [Water: chemistry and ecology, 2013]

The journal publishes original scientific articles and reviews of a theoretical and practical nature, devoted to innovative research in the field of chemistry and technology of water treatment, water supply, wastewater disposal, water quality control and monitoring of water bodies.

M.: PROMEDIA

Using the quantum chemical method DFT B3LYP/6-31G*, the deformation of naphthalene molecules under tension up to destruction in two directions corresponding to the “chair” and “zigzag” structures for carbon nanotubes was calculated. The equilibrium distribution of states over vibrational energy levels is calculated for various temperatures.

silver in solutions containing a passivating additive provides a significant reduction in the oxidation rate<...>In Fig. Figure 1 shows two options for applying force to the carbon atoms of the naphthalene molecule, corresponding to the data<...>Naphthalene molecule loading schemes 1.<...>Deformation curves of a naphthalene molecule: 1st stretch according to scheme a, 2nd stretch according to scheme b 2.<...>Probability distribution of filling levels at different temperatures for a naphthalene molecule (energy

This work presents preliminary tests of adsorption modification of the surface of metal powders with components of motor oils. It has been shown that the method used is capable of showing differences in modification depending on the nature of the modifying agent and the type of metal. Methods have been proposed for determining the nature of the surface (polar or non-polar)

Benzene, naphthalene, anthracene and benzoic acid were used as probe substances.<...>Benzene, naphthalene and anthracene are universal substances for testing columns, as in normal<...>Decane 1.17 Anthracene Decane 1.17 Benzoic acid Decane 1.31 Order of release of benzene, naphthalene, anthracene<...>The order of release of the mixture of benzene, naphthalene, anthracene, benzoic acid on the columns is somewhat different,<...>This suggests that in addition to oxidized surface carbon, the surface contains carbon in

Systematic Nomenclature of Organic Chemistry: A Directory to Comprehension and Application of its Basic Principles

M.: Knowledge Laboratory

Connecting nomenclature: naphthalene -1,2,4,6,7-pentaacetic acid Substituting nomenclature: naphthalene<...>aldehyde group: ...onic acids (common name - aldonic acids); b) terminal oxidation<...>Names of complex compounds naphthalene -2-yl-(E)-diazenolate of lithium Traditional name: naphthalene -2-anti-diazoate<...>Connecting nomenclature: naphthalene -1,2,4,6,7-pentaacetic acid Substituting nomenclature: naphthalene Series compounds

Similarly, the high oxygen content (18%) may be due to oxidation of the sample during<...>Most active in the hydrogenation of naphthalene at a temperature of 380°C and a water content in precursors of 1 wt.<...>The conversion of naphthalene in its presence reached 98%, the overall selectivity for decalins was 55%.<...>Effect of precursor composition on naphthalene conversion (α) and decalin selectivity (S).<...>Replacing naphthalene with sterically more hindered mono and dimethylnaphthalenes led to a noticeable decrease

No. 6 [Kinetics and catalysis, 2017]

Founded in 1960. Currently, the only specialized Russian periodical publishing the results of theoretical and experimental research in the field of homogeneous and heterogeneous kinetics and catalysis. The subject of the journal covers the mechanisms and kinetics of non-catalytic processes in gas, liquid and solid phases, photocatalysis, quantum chemical calculations in the field of kinetics and catalysis, preparation of catalysts, problems of their deactivation, macrokinetics and computer modeling in the field of catalysis. The journal “Kinetics and Catalysis” is included in the List of Higher Attestation Commissions

Rostov n/d.: Southern Federal University Publishing House

The textbook is compiled on the basis of many years of experience in teaching organic chemistry at the Faculty of Chemistry of the Southern Federal University and contains theoretical material, options for individual homework and additional tasks on four module topics (“Electrophilic substitution in the aromatic ring”, “Phenols”, “Aromatic amines. Diazonium salts”, “Nucleophilic substitution in the aromatic nucleus”), studied by students as part of the general course “Organic Chemistry”.

Relation of phenols to oxidation.<...>Starting from naphthalene, get 1-amino-2-hydroxynaphthalene. 3.<...>Side chain oxidation. Oxidation and reduction reactions of the benzene ring. Birch's reaction.<...>Naphthalene, anthracene and phenanthrene. mothballs

The textbook contains the main theoretical principles of the course of lectures on the discipline Organic chemistry and the fundamentals of biochemistry, a test task and recommendations for its implementation. Recommended by the educational and methodological association for education in the field of chemical technology and biotechnology as a teaching aid for students of higher educational institutions studying in the areas of Chemical technology and Energy and resource-saving processes in chemical technology, petrochemistry and biotechnology.

Oxidation reactions.<...>As an impurity, the trimerization of acetylene produces naphthalene. 3.<...>Naphthalene (n=2) colorless crystals.<...>Naphthalene is oxidized in the vapor phase over catalysts containing V2O5 at elevated temperatures.<...>Oxidation of alcohols: a)

according to literature data, those found in water in the highest concentration (phenanthrene, fluoranthene, naphthalene<...>do not interfere (do not cause the disappearance of luminescence at the end of the determination) phenanthrene, fluoranthene, naphthalene<...>standards have been established for benzo(a)pyrene in all media and for another 5 PAHs (anthracene, acenaphthene, naphthalene<...>The following reagents were used: naphthalene, acenaphthylene, fluorene, fluoranthene, pyrene, benzanthracene, chrysene<...>Parameters of fluorimetric detection of PAH PAH tR, min λexcitation, nm λemission, nm Naphthalene

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HIGH ENERGY CHEMISTRY, 2008, volume 42, no. 5, p. 381-387

^ RADIATION

GAS-PHASE RADIATION-CHEMICAL OXIDATION OF NAPHTHALEN

* Joint Institute for Energy and Nuclear Research - "Sosny" of the National Academy of Sciences of Belarus Belarus, 220109, Minsk, st. Academician Krasina, 99 E-mail: [email protected]**Institute of Mechanics, Moscow State University. M.V. Lomonosova 119192, Moscow, Michurinsky Prospekt, 1 E-mail: [email protected] Received by the editor on April 7, 2008.

Based on an analysis of literature data, a kinetic model of gas-phase radiation-chemical oxidation of naphthalene was constructed. Using the model, the main channels of naphthalene conversion were studied. It has been shown that under the conditions of electron beam purification of industrial gases from NO and SO2 (EBDS process), the main product of naphthalene radiolysis is nitronaphthalene. The results of numerical calculations are compared with experimental data.

The current level of use of organic fuels in various spheres of human activity causes significant environmental pollution with the products of their combustion. Among the harmful components of combustion products, polycyclic aromatic hydrocarbons (PAH), many of which have high carcinogenic activity, occupy a special place. The simplest and most common representative of RAS in the urban atmosphere is naphthalene.

Data on the kinetic mechanisms of gas-phase oxidation of even the simplest RAS are quite limited due to the diversity and complexity of the structure of the resulting products and relate mainly to high-temperature oxidation of RAS during combustion and their photochemical transformation in the atmosphere. For a correct quantitative description of the processes under consideration and assessment of their impact on the environment, a more detailed study of their mechanisms and identification of possible oxidation products is required.

A theoretical study of the radiation-chemical oxidation of RAS in gas under the influence of an electron beam was carried out in, where the main ways of formation and transformation of these compounds are considered in relation to the electron beam method of purifying industrial gases from NO and 802 (BBB^-process). However, the kinetic mechanism of the process is presented in a simplified form without quantifying the concentrations of oxidation products, some of which may be more toxic than the original reagents. Experimental

There are no detailed data on RAS radiolysis products in an oxidizing environment.

In this work, a kinetic model of the gas-phase oxidation of naphthalene (No.<) под действием ионизирующего излучения. С помощью модели сделана оценка концентраций основных продуктов окисления при типичных условиях проведения БББ8-процесса.

KINETIC MODEL OF THE PROCESS

The main initiating role in the radiation-chemical oxidation of RAS is played by OH and NO^ radicals as well as 03 molecules. The mechanisms of interaction of aromatic molecules with these active components have not been fully studied and require further clarification. Nevertheless, available theoretical and experimental studies make it possible to determine the main channels of the oxidative process and construct its kinetic model.

The interaction of OH radicals with RAS molecules is characterized by a nonmonotonic dependence of the reaction rate constant on temperature in the region T = 250-1250 K. Two temperature ranges can be distinguished, distinguished by different reaction channels and, accordingly, different behavior of the k0H = ^H(7) curve. At high temperatures (G > 400 K for benzene), the H atom is abstracted from the aromatic molecule and an aromatic radical is formed, which further interacts with the molecular oxygen

house, which ultimately leads to the formation of CO and H20 (combustion process).

At low temperatures (T< 350 К для бензола) начальную стадию окислительного процесса можно представить в виде цепочки реакций присоединения радикала ОН к ароматической молекуле с образованием ОН-аддукта (С10Н8-ОН в случае окисления нафталина), который далее преобразуется в другие соединения в реакциях с участием радикалов ОН и молекул О2, КО, ЫО2 . Скорость процесса практически не зависит от температуры и определяется скоростью первой стадии с константой скорости кОН, зависящей от вида соединения. В частности, для таких молекул, как бензол, нафталин, фенантрен и антрацен кОН равна соответственно 7.2 х 1011, 1.4 х 1013, 1.5 х 1013 и 1.1 х 1014 см3/(моль с) при Т = 350 К .

It should be noted that the low-temperature region, in which the reaction of the interaction of the OH radical with an aromatic molecule proceeds along the path of formation of the OH adduct, almost completely coincides with the temperature regime of the EBB8 process. On the other hand, for RAS molecules, in contrast to benzene, the upper limit of this region is at significantly higher temperatures (about 700 - 900 K for anthracene). Therefore, the high-temperature oxidation of aromatic molecules, which occurs along the path of abstraction of the H atom by OH radicals with the formation and subsequent decomposition of an aromatic radical, is not considered further.

One of the main channels for the radiation-chemical oxidation of naphthalene is the formation of nitronaphthalene C10H7-CO2 during the interaction of the OH adduct with NO2 molecules. At concentrations of NO2 in the gas typical for the EBC8 process (about 100 cm3/m3), this channel, as further calculations show, plays a predominant role in the process of naphthalene conversion at its initial stage (B< 8 кГр).

The interaction of the OH adduct with molecular oxygen leads to the formation of naphthol C10H7-OH, which, when reacting with OH radicals and NO2 molecules, is converted into hydroxy-nitronaphthalene NO2-C10H6-OH. In this chain of reactions, intermediate products can additionally react with O2 and CO2, which leads to a decrease in the yield of hydroxynitronaphthalene and the formation of other products of the oxidation process.

The OH adduct formed by the addition of the OH radical to the PAN molecule in the reaction with O2 can also be converted into a bicyclic radical, which is further destroyed when interacting with molecular oxygen and nitric oxide. The process proceeds in the direction of reducing the number of aromatic rings in the PANO molecule. In the case of naphthalene, the reaction products for this channel of oxidation of PAN8 molecules are glyoxal

HC(O)CHO and 2-formylbenzaldehyde C6H4(CHO)2.

The mechanism of interaction of NO3 radicals with aromatic molecules is in many ways similar to the corresponding mechanism involving OH radicals. The reaction of the addition of the NO3 radical to a naphthalene molecule leads to the formation of a NO3 adduct, which then either decomposes into naphthol and NO2, or, upon interaction with NO2, forms nitronaphthalene and NO2. The rate of the process, as in the case of OH radicals, is determined by the rate of the first stage with a rate constant approximately 4 times less than kOH. Therefore, this mechanism makes a significant contribution to the process of naphthalene conversion only when the concentration of NO3 radicals in the gas exceeds the concentration of OH radicals.

The interaction of O3 molecules with aromatic molecules should not significantly affect the dynamics of the oxidative process. As an analysis of the available data shows, the rate constant of this interaction is eight orders of magnitude less than the corresponding value for the interaction of aromatic molecules with OH radicals.

Based on an analysis of literature data, this work constructs a kinetic model of the radiation-chemical oxidation of naphthalene, taking into account the mechanisms listed above. A list of reactions along with rate constants in the forward (+) and reverse (-) directions is given in table. 1. For reactions for which there is no kinetic information, the reaction products and rate constants are given by analogy with the data for benzene. As can be seen from the table, some oxidation products of naphthalene and its derivatives have not been identified, which is due to the lack of relevant information.

The OH and NO3 radicals, which play the main role in the process under consideration, are formed in the gas during the radiative effect of radiation on the macrocomponents of the gas (K2, O2, H2O and CO2). To determine the concentrations of these radicals in the radiation-chemical zone, a mathematical model of the EBB8 process was used.

RESULTS AND DISCUSSION

Since there are no experimental data on the products of radiation-chemical oxidation of naphthalene, testing of the kinetic model was carried out on the results of photolysis of a mixture of naphthalene, methyl nitrite (CH3ONO), KO and NO2 in air. Process temperature T = 296 K, pressure р = 0.1 MPa, process time r = 500 s, component concentrations: CH3ОШ = 2.1 x 1014, СО = 2.4 x x 1014, Ш2 = 4.1 x 1013, NL = 2.1 x 1013 molecule/cm3 . OH radicals are generated due to the photolytic decomposition of methyl nitrite with a rate constant

Table 1. Kinetic scheme of naphthalene oxidation at T = 300 K

No. Reaction k+ k_ Literature

1 SHI8 + OH - C10H8-OH 13.15 -

In substitution reactions in naphthalene derivatives, the entry of an electrophilic particle occurs in accordance with the following rules:

1) The electron-donating group directs the electrophilic reagent to the ring in which it is located. If this group is at position 1, the electrophilic species displaces a hydrogen at position 2 or at position 4, the electron-donating group at position 2 directs the electrophilic species to position 1.

2) The electron-withdrawing group directs the electrophilic reagent to another unsubstituted ring (to position 5 or 8 in halogenation and nitration).

This direction of substitution can be explained as follows. The orientation has the greatest influence on the ring to which it is associated. Therefore, the most successful is the attack by the electrophile E Å of the ring with the electron-donating group G, in which the positive charge can be better distributed.

Reduction and oxidation of naphthalene

When naphthalene is oxidized in the presence of vanadium pentoxide, one ring is destroyed and phthalic anhydride is formed.

Naphthalene is oxidized by a mixture of K 2 Cr 2 O 7 and H 2 SO 4 to phthalic acid.

If there is a substituent in one of the rings, then the ring with increased electron density is oxidized.

Unlike benzene, naphthalene can be reduced with chemical reducing agents.

The benzene ring in tetralin is reduced only under harsh conditions.

Anthracene and phenanthrene

Anthracene and phenanthrene are aromatic compounds. They are flat cyclic structures containing a closed p- electron cloud located below and above the plane of the rings. Number p- electrons in accordance with Hückel's rule is 4n + 2 = 4 × 3 + 2 = 14.

Anthracene can be considered as a resonance hybrid of structures I-IV.

Its resonance energy is 352 kJ/mol.

Phenanthrene can be represented as a resonance hybrid of structures V-IX.

The resonance energy of phenanthrene is 386 kJ/mol.

Anthracene and phenanthrene undergo electrophilic substitution reactions. Their active positions 9 and 10 are located in the middle ring, since when attacking these positions, the aromaticity of the two side benzene systems is preserved with a resonance energy of 153 × 2 = 306 kJ/mol. When attacking the side rings, the aromaticity of one naphthalene fragment is preserved with a resonance energy of 256 kJ/mol.

The conclusion about the activity of positions 9 and 10 is valid both for electrophilic substitution and for oxidation and reduction reactions.

The main areas of application of naphthalene are presented in the diagram (Fig. 16).

One of the most important areas of industrial use of naphthalene is oxidation to phthalic anhydride. The oxidation of naphthalene is carried out by the vapor phase method on a vanadium-potassium sulfate catalyst in a stationary or fluidized bed:

4-502 - a: > +2С02 + 2Н20

The yield of phthalic anhydride on this catalyst is

86-89%, product productivity 40 kg/h per 1 m3 of catalyst. By-products of the process are 1,4-naf - toquinone, maleic anhydride, CO2.

Modification of the catalyst made it possible to increase its productivity to 50-55 kg/(h m3) and the yield of phthalic anhydride to 90-94%. The oxidation process occurs at a mass ratio of naphthalene: air = 1: 35 and a temperature of 360-370°C. Naphthalene consumption is 1.05-1.1 t per 1 t of phthalic anhydride.

The Badger company has developed a process for oxidizing naphthalene at a higher concentration (mass ratio of naphthalene: air - 1: 12) in a fluidized bed of catalyst.

By vapor-phase oxidation of naphthalene with air at 250-450°C in the presence of catalysts V205, V205-A1203, Zr02, Si02-W03, B203, alkali metal phosphates, 1,4-naphthoquinone is also obtained. It is possible to use V205-K2S04 modified with oxides of Fe, Sn, Si, Ti, Al as a catalyst.

CC) °°n

С6Н^П(С2Н5)„

GeCl3 COCH3

Na28x thioindigoid

С1СН2СН2С1

CH2=C(11)-C(H)=CH2

Rice. 16 (continued)

At a temperature of 430-480 °C, naphthalene oxidation occurs with high conversion, which eliminates the stages of separation and recycling of raw materials.

It is possible to obtain 1,4-naphthoquinone by oxidation of 1-naphthol with oxygen with a yield of 90% in the presence of the catalytic complex Co-salcomine in dimethylformamide.

1,4-Naphthoquinone is used for the synthesis of anthraquinone and its derivatives, dyes, antibacterial drugs and fungicides.

By alkylation of naphthalene with higher linear a-olefins containing 12-20 carbon atoms, higher alkylnaphthalenes are obtained. The catalysts used are macroporous Y-type zeolites with H+ and NH4 exchange centers, the same zeolites modified with rhenium, and solid acid catalysts based on Zr02 modified (NH4)6H4W1205. The resulting monoalkylnaphthalenes are used as lubricating oils and high-temperature coolants with high thermal conductivity.

Alcohols and alkyl halides can be used as an alkylating agent instead of olefins. Mobil Oil Corp. patented the MSM-49 catalyst of the composition X203 pU02 for the alkylation of naphthalene, where p< 35, X - трехвалентный элемент (А1, В, Fe, Ga или их смесь), Y - четырехвалентный элемент (Si, Ti, Ge или их смесь) .

In 1975, the high-temperature coolant Termolan based on higher alkylnaphthalenes was developed, produced by Orgsintez PA (Novomoskovsk). This is a liquid product with a melting point of -30-45°C, a boiling point of 450-500°C and a stable operating temperature range from -35 to 350°C. The coolant is characterized by low toxicity (MPC = 30 mg/m3), low saturated vapor pressure (0.05-0.1 MPa at maximum temperature of use), relatively low viscosity (60 mm2/s at 20 °C), low corrosiveness, and high radiation resistance.

Alkylnaphthalenes, obtained from naphthalene and 1-eicosene or 1-docosene, are used as working fluids in vacuum steam jet pumps and provide the creation of ultra-high vacuum (2.8-4.8) ■ 10“7 Pa. Instead of individual α-olefins, the C18-C20 fraction of paraffin cracking distillate can be used for naphthalene alkylation. Naphthalene alkylation is carried out in the presence of the BF3-H3P04-S03 catalyst at 100 °C for 1 hour, the yield of alkylnaphthalenes is 50-55%. The resulting vacuum liquid, 280
called Alkaren-1, allows you to create a vacuum of about 10“7 Pa in diffusion pumps.

Based on the 180-240 °C fraction of cracking distillate containing C8-C20 a-olefins and naphthalene, vacuum working fluid Alcaren-24 was also obtained. To avoid oligomerization, α-olefins were preliminarily hydrochlorinated in the presence of 1 wt % gpCl2 on silica gel. Alkylation of naphthalene with alkyl chlorides was carried out in the presence of AlC13 at 20-100°C. Vacuum oils were also obtained by alkylation of biphenyl with C8-C12 alkyl chlorides (Alcaren D24) and C12-C14 a-olefins (Alcaren D35). The technology for producing Alkaren vacuum oils was tested at the pilot plant of the Khimprom Production Association (Kemerovo). An important advantage of vacuum oils based on naphthalene or biphenyl and industrial mixtures of a-olefins compared to foreign analogues obtained using individual hydrocarbons is their significantly lower cost.

By alkylation of naphthalene with alcohols, for example 2-butanol, and simultaneous sulfonation with concentrated H2804 or weak oleum, alkylnaphthalene sulfonates are obtained, which are used as surfactants. Alkylnaphthalene sulphates are also used as anti-corrosion and detergent-dispersant additives for lubricating oils.

By nitration of naphthalene with a mixture of concentrated NJ)3 and H2O4 at 50-60°C, 1-nitronaphthalene is obtained. The impurities of 2-nitronaphthalene account for 4-5% (may.) and dinitronaphthalenes - about 3% (may.). Further nitration of 1-nitronaphthalene produces a mixture of 1,5- and 1,8-dinitronaphthalenes.

By hydrogenating 1-nitronaphthalene in the presence of Na or Cu, 1-naphthylamine is obtained, the sulfonation of which produces naphthionic acid:

The rearrangement of 1-naphthylamine hydrosulfate is carried out in o-dichlorobenzene a at 175-180 °C.

Sulfonation of naphthalene with concentrated H2S04 at a temperature of about 80 ° C leads to the formation of 1-naphthalene sulfonic acid, and at temperatures above 150 ° C - to 2-naphthalene linsulfonic acid.

The company Chemie AG Bitterfeld-Wolfen has patented a method for producing naphthionic acid by reacting 1 mol

1-naphthylamine and 1-1.2 mol 95-100% H2S04 with the formation of naphthylamine hydrosulfate and its subsequent sintering with

1-1.3 mol of fine-crystalline amidosulfonic acid at 160-200 °C. Naphthionic acid is isolated by heating the reaction mixture with 1 N. HC1 to boiling and purified through sodium naphthionate using activated carbon. Purified naphthionic acid is suitable for producing food coloring.

By reacting 1-naphthylamine with aniline in the liquid phase at 230-250 °C in the presence of 12 or /g-toluenesulfonic acid or in the vapor phase at 800 °C over gel A1203, N-phenyl-1-naphthylamine (neozone A) is obtained, which is used in the production of arylmethane dyes.

When nitrating 1-naphthalene sulfonic acid, a mixture of 5- and 8-nitronaphthalene-1-sulfonic acids is obtained, the reduction of which with cast iron turnings produces the corresponding amino derivatives:

In a similar way, Kleve acids are obtained from 2-naphthalene sulfonic acid - a mixture of 5- and 8-aminonaphthalene-2-sulfonic acids. Naphthylaminosulfonic acids are used in the production of dyes, as well as reagents for the film and photo industry.

In the two-stage sulfonation of naphthalene, first with 20% oleum at a temperature not exceeding 35°C, then with 65% oleum 282

At 55 °C, naphthalene-1,5-disulfonic acid (Armstrong's acid) with an admixture of naphthalene-1,6-disulfonic acid is obtained.

By alkaline melting of naphthalene-2-sulfonic acid at 300-315 ° C, 2-naphthol is obtained with a yield of up to 82%. It is possible to obtain 2-naphthol by hydroxylation of naphthalene with a 28% solution of H2O2, first at 50 °C, then at 80 °C in the presence of a catalyst - copper tetrakis(decachlor)phthalocyanine. The naphthalene conversion is 22.3%, the selectivity for the formation of 2-naphthol is 90%.

Alkylation of naphthalene with 2-propanol in the presence of mordenite at 250 °C produces 2-isopropylnaphthalene, the oxidation of which to hydroperoxide and acid decomposition also produces 2-naphthol and acetone. The maximum yield of 2-naphthol - 61% - was achieved when using HC104 as a catalyst in a solution of acetic acid.

When naphthalene is alkylated with 2-propanol on H-U and LaH-U zeolites, mainly 1-isopropylnaphthalene is formed, from which 1-naphthol can be obtained. In industry, 1-naphthol is produced by alkaline melting of naphthalene-1-sulfonic acid with NaOH at 300 °C with a yield of about 93% or by hydrolysis of 1-naphthylamine under the influence of 20% H2804 at 185-240 °C.

Alkylation of naphthalene with propylene or 2-propanol in the presence of H-type supported on mordenite with a molar ratio of SiO2/Al2O3 over 15, with a naphthalene conversion of 95.2%, is accompanied by the formation of 2,6-diisopropylnaphthalene with a selectivity of 61.9%. When naphthalene is alkylated on the same mordenite zeolite with 0.5% (wt.) P1 in the presence of water additives, the conversion increases to 97.5% and the selectivity for the formation of 2,6-diisopropylnaphthalene to 67.3%. Impregnation of H-mordenite with cerium nitrate (at 30% (wt.) Ce) leads to an increase in selectivity for the same isomer to 70%

Computer search for the optimal synthesis catalyst

2,6-diisopropylnaphthalene also confirmed the choice of mordenite

During the catalytic interaction of naphthalene with di- and tri-methylnaphthalenes in the presence of zeolites, transmethylation and isomerization reactions occur simultaneously with the enrichment of the reaction mixture with 2,6-dimethylnaphthalene.

When naphthalene is alkylated with methanol using H-hvM-b zeolite, 2-methylnaphthalene is formed. The mechanism of P-selective methylation is explained by the fact that 1-methylnaphthalene molecules, which have a larger volume, do not penetrate into the zeolite channels. Further methylation of 2-methylnaphthalene on ZSM-5 zeolite, especially when its outer surface is poisoned with 2,4-dimethylquinoline, selectively produces 2,6-dimethylnaphthalene.

Similar methods can be used to obtain 2,6-diethylnaphthalene. Alkylation of naphthalene with ethylene or ethyl halide in the presence of zeolites produces predominantly 2,6-diethylnaphthalene, which is purified by crystallization or chromatography on a Y-type zeolite modified with Na, K or Ba ions.

Nippon Steel Chemical Co. patented a process for producing 2,6-diethylnaphthalene by reacting naphthalene or 2-ethylnaphthalene with polyethylbenzenes in the presence of zeolite U. Thus, when 2-ethylnaphthalene reacted with tetraethylbenzenes at 80 °C after 2 hours, a conversion of 2-ethylnaphthalene of 82.7% was achieved, the yield of diethylnaphthalenes was 62.3 %, their composition, %:

2.6-50.1; 2.7-24.8; 1.6-15; 1.7-5.3; other isomers 4.8. Oxidation of 2,6-dialkylnaphthalenes produces 2,6-naphthalenedicarboxylic acid.

Hydrogenation of naphthalene in the presence of nickel catalysts at 150°C leads to the formation of tetralin, and at 200°C - to a mixture of cis- and trans-decalins. The yield of decalins is about 95% when tetralin is hydrogenated on a platinum aluminophosphate catalyst supported on A1203 at a process temperature of 220 °C and a pressure of 5.17 MPa. An effective catalyst for the hydrogenation of naphthalene to decalins is 0.1% (wt.) Ru on mixed oxides Mn203-Ni0.

The hydrogenation of tetralin to cis- and mpawc-decalin occurs with high yield in a two-phase system, including a catalyst - chloro(1,5-hexadiene)rhodium dimer and an aqueous buffer solution with a surfactant. The catalyst remains highly active after 8 cycles.

Tetralin and decalin are recommended to be used instead of 100-200 aromatic solvents - dangerous air pollutants. They are used in paints and inks, pharmaceuticals, and in the production of agrochemicals. Tetralin and decalin are produced, in particular, by the American company Koch Specialty Chemicals at the plant in Corpus Christi, PC. Texas. In Russia, tetralin is produced by JSC Torzhok Printing Inks Plant in the Tver Region.

Based on alkyltetralins, medium-alkaline sulfonate additives for motor oils are obtained.

Liquid-phase chlorination of naphthalene in the presence of FeCl3 produces 1-chloronaphthalene with admixtures of 2-chloro-, 1,4- and 1,5-di-chloronaphthalenes. Chlorination of molten naphthalene also produces a mixture of tri- and tetrachloronaphthalenes - halo - wax. Halovax is used as a phlegmatizer, a substitute for wax and resins in impregnating fabrics, insulating wires, and making capacitors.

When naphthalene is acetylated with acetic anhydride in dichloroethane or chlorobenzene, it is obtained with a yield of 98%

1-acetylnaphthalene, and when the reaction is carried out in nitrobenzene, 2-acetylnaphthalene with a yield of about 70%. 2-Acetyl - naphthalene is used as a fragrant substance and odor fixative in the preparation of fragrances for soaps and perfume compositions.

By reacting 1-acetylnaphthalene with sodium polysulfide, a red-brown thioindigoid dye is obtained:

Thioindigoid dyes are more resistant than indigoid dyes to the action of oxidizing agents and alkalis and are used for printing on cotton, linen, viscose, for vat dyeing of wool and fur, as pigments in printing.

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