Journal "Chemistry and Technology of Organic Substances", N 1 (17) /2021

Section I. ORGANIC SYNTHESIS

Gorelenko S.V., Zinina E.A., Kazakov P.V., Litvinov Yu.M., Derevyagina I.D., Mirzabekova N.S., Kharchenko I.S.
Di(o-xylyl)methanes
Federal state unitary enterprise «State Scientific-Research Institute of Organic Chemistry and Technology» State Scientific Center of n Federation. Moscow 111024, Russia

Abstract
A method for producing diarylmethanes in the presence of isobutanol using phosphoric acid as a catalyst is proposed using the example of the interaction of 
o-xylene with paraform.
Keywords: diarylmethane; di(o-xylyl)methane; 
3,3′,4,4′-tetramethyldiphenylmethane; formaldehyde;paraform; phosphoric acid; butyl alcohols; isobutanol.
References
1. Moshchinskaya N.K., Globus R.L. Issledovaniye v ryadu difenilmetana iy ego proizvodnykh. Soobshcheniye 1. Izucheniye kataliticheskikh faktorov protsessa polucheniya difenilmetana. // Zhurnal Prikladnoy Khimii. 1944. T. 17. N 1–2. S. 76–82.
2. Patent US 2937212A, C07C2/867. Production of diarylmethanes // Dreier Ir.L., Cheney H.A., Knott R.F.: publ. 17.05.1960.
3. Patent SU 563411А, С07С15/16. Sposob polucheniya diarilmetanov. Bondarenko A.V., Farberov M.I., Shustovskaya G.N. i dr.: publ. 30.06.1977.
4. Hendrickson J.G., Wadsworth F.T. Synthesis of durene from pseudocumene // Industrial and Engineering Chemistry. 1958. V. 50. N 6. P. 877–878. DOI: 10.1021/ie50582a029.
5. Mironov G.S., Vetrova V.V., Kozlova I.P., Farberov M.I. Polucheniye diarilmetanov i ikh gidrokreking v polimetilbenzoly // Zhurnal Prikladnoy Khimii. 1966. T. 39. N 7. S. 1614–1621.
6. Patent SU 777022, MPK S 07 S 15/16. Sposob polucheniya dipsevdokumilmetana / Rakhmankulov D.L., Kantor Ye.A., Kukovitskiy M.M. i dr.: publ. 07.11.1980.
7. Patent SU 925925, MPK S 07 S 15/16. Sposob polucheniya diarilmetanov / Bondarenko A.V., Prozorov V.A., Yas’kina V.G. i dr.: publ. 07.05.1982.
8. Heyuan S., Fuxiang J., Ronghua J., Meirong K., Zhen L. Functional ionic liquids as efficient and recyclable catalysts for the methylation of formaldehyde with aromatics // Catalysis Letters. 2016. V. 146. N 7. P. 1264–1272.
DOI 10.1007/s10562-016-1750-5.
9. Patent RU 2182896, MPK S 07 S 15/16, 37/20. Sposob polucheniya diarilmetana ili ego proizvodnykh / Kavamata T., Dokhi KH., Inouye S., Khayasi S.: opubl. 27.05.2002.
10. Patent US 2011/0172481, МПК С 07 С 1/20. Process of producing of 1,1-diaryl alkanes / Dimmit J.H., Cagle M.D: publ. 14.07.2011.
11. Moshchinskaya N.K., Globus R.L. Issledovaniye v ryadu difenilmetana i yego proizvodnykh. Soobshcheniye 2. Zavisimost’ vykhoda difenilmetana ot sootnosheniya vzyatykh dlya reaktsii benzola i formal’degida. // Zhurnal Prikladnoy Khimii. 1944. T 17. № 3. S. 137-143.
12. Patent GB 446450. Improvement in the manufacture of di-aryl-methanes and their derivatives / Blythe W., Bentley W.H., Catlow B.: publ. 06.11.1935.
13. Meyerson S., Drews H., and Fields E. K.Mass spectra of ortho-substituted diaryl methanes // Journal of American Chemical Society. 1964. V 86. N 20. P. 4964–4967. DOI: /10.1021/ja01076a044.
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Rumyantseva T.A., Tkachenko M.A., Alekseeva A.A.
Synthesis of cobaltphthalocyanines containing anthraquinone chromophors
Research Institute of Chemistry of Macroheterocyclic Compounds, Ivanovo State University of Chemical Technology, Ivanovo 153000, Russia

Abstract
Anthraquinone-substituted nitriles have been synthesized by reaction of nucleophilic substitution of bromine in 4-bromo-5-nitrophthalonitrile. The obtained substances were used for the synthesis of the corresponding cobalt complexes by the nitrile method. The compounds obtained were characterized by various physicochemical methods.
Keywords: phthalocyaninates; cobalt complexes; anthraquinone; electronic absorption spectroscopy data; pigments.
References
1. Shaposhnikov G.P., Kulinich V.P., Maizlish V.E. Modifitsirovannye ftalotsianiny i ikh strukturnye analogi. In Koifman O.I. (ed.). Moscow: KRASAND, 2012. 480 s.
2. Stepanov B.I. Vvedenie v khimiyu i tekhnologiyu organicheskikh krasitelei. Moscow: Khimiya, 1984. 527 s. (In Russ.).
3. Shishkina O.V., Maizlish V.E., Shaposhnikov G.P. and other. Galogenonitroftalimidy i ftalodinitrily na ikh osnove. Zhurnal organicheskoi khimii. 1997. T. 76. rel. 5. S. 842.
4. Vorob’ev Yu.G., Shaposhnikov G.P. Laboratornyi praktikum po khimii organicheskikh krasitelei. Ivanovo: IGKhTA, 1996. 76 s.
5. Abramov I.G., Smirnov A.V., Ivanovskij S.A. i dr. Sintezy geterociklov na osnove 4-brom-5-nitroftalonitrila // Himiya geterociklicheskih soedinenij. 2000. T. 36. N 9. S. 1219.
6. Daier D.R. Prilozheniya spektroskopii organicheskikh soedinenii. Moscow: Khimiya, 1970. 163 p. (In Russ.).
7. Elektronnye spektry ftalotsianinov i rodstvennykh soedinenii. In Luk’yantsa E.A. (ed.). Cherkassy: NIITEKhim, 1989. 94 s.
8. Znoyko S.A., Mikhailova A.I., Akopova O.B. et al. Synthesis of Cu(II) and Ni(II) phthalocyanines bearing nitro and 4-(1-methyl-1-phenylethyl)phenoxy groups // Macroheterocycles. 2018. Vol. 11. N 3. P. 41.DOI: 10.6060/mhc180169z.
9. Rumyantseva T.A., Tarasova E.S., Maltseva E.S., Shaposhnikov G.P. Complexes of Erbium and Lutetium of different compositions with 4-R-5-nitro-substituted phthalocyanines // Russian Journal of General Chemistry. 2020. Vol. 90. N. 1. P. 118–122.
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Section II. TECHNOLOGY OF ORGANIC SUBSTANCES

Polkovnichenko A.V.1, Chelyuskina Т.V.2
Mutual transformations of α = 1 lines diagrams of butyl butyrate – butyric acid – separating agent systems
1Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia
2M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA – Russian Technological
University, Moscow 119571, Russia
Abstract
Using the Aspen Plus® V. 9.0 software package a computational experiment on mathematical modeling of the vapor-liquid equilibrium in the three-component systems formed by the biazeotropic binary constituent butyl butyrate – butyric acid and one of the potential separating agents - nitrobenzene or gamma-butyrolactone was performed. It was found that at pressure changes the mutual transformations
of α = 1 lines diagrams of these systems occur while maintaining the structure of the distillation lines diagram. The principal feasibility of the directed formation of α = 1 lines diagrams to control the compositions of product streams of the extractive rectification process due to the inversion of the components volatility of the basic (separated) mixture under various external conditions was shown.
Keywords: vapor-liquid equilibrium; biazeotropic system; α = 1 lines diagram, extractive distillation; product streams.
References
1. Zharov V.T., Serafimov L.A. Physicochemical foundations of distillation and rectification. Leningrad: Khimiya. 1975. 240 s. (in Russ.).
2. Petlyuk F.B., Serafimov L.A. Multicomponent Distillation: Theory and Design. Moscow: Khimiya. 1983. 304 s. (in Russ.).
3. Frolkova A.K. Separation of Azeotropic Mixtures: Physicochemical foundations and technological techniques. Moscow: VLADOS Publ. 2010. 192 s. (in Russ.).
4. Seader J.D., Henley E.J. Separation Process Principles. New York: Wiley. 1998. 886 p.
5. Gorak A., Schoenmakers H. (eds.). Distillation: Operation and Application. Amsterdam: Elsevier. 2014. 450 p.
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7. Serafimov L.A., Gol’berg Yu.E., Kiva V.N., Vitman T.A. Main Properties of Unit ⍺-Manifolds and Their Location in Concentration Spaces // Sbornik nauchnykh trudov Ivanovskogo energeticheskogo in-ta (Research Papers of Ivanovo Power Engineering Institute). Ivanovo. 1972. P. 166–179. (in Russ.).
8. Kiva V.N., Hilmen E.K., Skogestad S. Azeotropic phase equilibrium diagrams: a survey // Chemical Engineering Science. 2003. V. 58. N 10. P. 1903–1953.
9. Myagkova T.O., Chelyuskina T.V., Frolkova A.K. The special features of the phase behavior of multicomponent biazeotropic systems // Russian Journal of Physical Chemistry. A. 2007. V. 81. N 6. P. 841–846.
10. Usol’tseva O.O., Serafimov L.A., Pisarenko Yu.A. Appearance of an internal tangential azeotrope in ternary systems // Theoretical Foundations of Chemical Engineering. 2010. V. 44. N 3. P. 293-299.
11. Reshetov S.A. Predsintez shem rektifikacii mnogokomponentnyh azeotropnyh smesej. (The Initial Development of the Rectification Schemes of Multicomponent Azeotropic Mixtures) M.: «Vlados», 2014. 192 p. (in Russ.).
12. Shcherbakova N., Rodriguez Donis I., Abildskov J., Gerbaud V. Univolatility curves in ternary mixtures: topology and bifurcation // Chemical Engineering Transactions. 2018. V. 69. P. 73-78.
13. Chelyuskina T.V., Polkovnichenko A.V., Modurova D.D. Extension of the classification of three-component systems containing binary biazeotropic components and not containing ternary azeotropes // Theoretical Foundations of Chemical Engineering. 2020. V. 54. N 6. P. 1247–1255.
14. Chelyuskina T., Zakhlevniy A., Modurova D. Mutual transformation of diagrams of k = 1 and ⍺ = 1 lines of three-component systems containing a binary biazeotropic constituent // Proceeding of 45th International Conference of the Slovak Society of Chemical Engineering. Slovakia. 2018. P. 127.
15. Chelyuskina T.V. Theoretical foundations of the distillation of biazeotropic mixtures : Dr. Sc. (Eng.) dissertation. Moscow: Moscow Inst. of Fine Chem. Technol., 2011. 196 p. (in Russ.).
16. Kogan V.B. Azeotropic and extractive distillation. 2nd ed. Leningrad: Khimiya. 1971. 432 p. (in Russ.).
17. Zhigang Lei, Chengyue Li, Biaohua Chen. Extractive Distillation: A Review // Separation & Purification Reviews. 2003. V. 32. N 2. P. 121–213.
18. Serafimov L.A., Chelyuskina T.V. Principles of classifying diagrams for different types of biazeotropic ternary mixtures // Russian Journal of Physical Chemistry. 2011. V. 85. N 5. P. 767–776.
19. Kushner T.M., Shutova G.V., Raeva V.M., Serafimov L.A. Investigation of biazeotropy in the butyric acid - butylbutyrate system // Zhurnal obschei khimii (Russian Journal of General Chemistry). 1993. V. 63. N 1. P. 171–176. (in Russ).
20. Chelyuskina T.V., Bedretdinov F.N. Mathematical modeling of extractive rectification of a butyl butyrate–butyric acid mixture // Theoretical Foundations of Chemical Engineering. 2016. V. 50. N 5. P. 697–704.
21. Chelyuskina T., Modurova D., Lukin N., Serafimov L.A. Mutual transformation of three-component systems diagrams with distinguishable deformation of the distillation lines // Proceedings of 44th International Conference of the Slovak Society of Chemical Engineering. Slovakia. 2017. P. 147.

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Fedosov I.A.1, Lebedev A.V.1, Storozhenko P.A.1, Apal’kov A.V.1, Kitaeva N.S.2,
Shiryakina Yu.M.2, Ponomarenko S.A.2, Novikova A.A.2
The synthesis of α,ω-dihydroxymethylphenylsiloxane polymers with controlled molecular weight distribution
1State Scientific Center of Russian Federation Joint Stock Company “State Research Institute
for Chemistry and Technology of Organoelement Compounds”. Moscow 105118, Russia
2Federal State Unitary Enterprise «All-Russian Institute of Aviation Materials» State Scientific Center of Russian Federation. Moscow 105005, Russia

Abstract
The process of catalytic polymerization of lower methylphenylcyclosiloxanes [MePhSiO]3-5 with the formation of linear α, ω-dihydroxymethylphenylsyloxane polymers, which are in demand for the production of film-forming block co-polymers with branched polysiloxanes, has been studied using NMR spectroscopy, HPLC and GPC. The influence of process parameters, such as temperature, duration of synthesis, composition of initial cyclosiloxanes, mass transfer in the reaction system, the type and amount of the process catalyst, and the method of removing volatile products on the distribution of polymer molecular weights was studied.
Keywords: methylphenylcyclosiloxanes; anionic polymerization; influence of process parameters; molecular weight distribution; linear α,ω-dihydroxymethylphenylpolysiloxanes; depolymerization.
References
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2. Saharudin M.S., Atif R., Shyha I., Inam F. The degradation of mechanical properties in polymer nano-composites exposed to liquid media – a review // RSC Adv. 2016. Vol. 6. P. 1076–1089. DOI: 10.1039/C5RA22620A.
3. Kuznetsova V.A., Semenova L.V., Kondrashov E.K., Lebedeva T.A. Lakokrasochnyye materialy s povyshennym soderzhaniyem vrednykh i toksichnykh komponentov dlya okraski agregatov i konstruktsiy iz PKM // Trudy VIAM. 2013. N 8. URL: http://viam-works.ru (data obrashcheniya 16.09.2020).
4. Patent RU 2467042 S1 MPK C09D 5/33, C09D 175/04. Polimernaya teplootrazhayushchaya kompozitsiya dlya pokrytiya / Malova N.Ye., Kablov Ye.N, Kondrashov E.K., Vereninova N.P., Barbot’ko S.L.: zayav. 07.06.2011; opub. 20.11.2012.
5. Brachaczek W. Comparative analysis of organosilicon polymers of varied chemical composition in respect of their application in silicone-coating manufacture // Progress in Organic Coating. 2014. Vol. 77. P. 609615.
DOI: 10.1016/j.porgcoat.2013.11.026.
6. Kondratenko A.N., Golubkova T.A. Polimernyye kompozitsionnyye materialy v izdeliyakh zarubezhnoy raketno-kosmicheskoy tekhniki // Konstruktsii iz kompozitsionnykh materialov. 2009. N 2. S. 24–35.
7. Zorin V.A. Opyt primeneniya kompozitsionnykh materialov v izdeliyakh aviatsionnoy i raketno-kosmicheskoy tekhniki // Konstruktsii iz kompozitsionnykh materialov. 2011. N 4. S. 44–59.
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10. Marsmann H. NMR Basic Principles and Progress. Vol. 17. Berlin: Springer-Verlag, 1981. Р. 65–235.
11. Ponomarenko S.A., Kitayeva N.S., Shiryakina Yu.M., Apal’kov A.V. Primeneniye metodov zhidkostnoy khromatografii i YAMR spektroskopii dlya kontrolya kachestva poli(metilfenil)siloksanov // Zhurnal prikladnoy khimii. 2014. T. 87. N 2. S. 237–243.
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14. Yuzhelevskiy Yu.A., Kagan Ye.G., Dmokhovskaya Ye.B. Vliyaniye prirody zamestiteley u atoma kremniya na ravnovesiye pri kataliticheskoy peregruppirovke tsiklosiloksanov v rastvore // Khimiya geterotsiklicheskikh soyedineniy. 1967. N 5. S. 951.
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16. Cypryk M. Polymerization of cyclic Siloxanes, Silanes and Related Monomers. In: Polymer Science: A Comprehensive Reference. Vol. 4: Ring-Opening Polymerization and Special Polymerization Processes / Eds.: Penczek S., Grubbs R.H. Elsevier, 2012. P. 451–476. DOI: 10.1016/B978-0-444-53349-4.00112-6.

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Section III. TEST METHODS FOR SUBSTANCES AND MATERIALS

Stan’kov I.N., Derevyagina I.D., Morosova O.T., Serdykova O.V.
Study of the stability of the drug form of Mexicor® by gas chromatography mass spectrometry
Federal state unitary enterprise «State Scientific-Research Institute of Organic Chemistry and Technology» State Scientific Center of n Federation. Moscow 111024, Russia

Abstract
A gas chromatography method with mass spectrometry detector was used for the examination of substances of 2-ethyl-6-methyl-3-hydroxypyridine succinate and colored and colorless dosage forms of the drug of Mexicor® preparation for injection. With the use of the GC-MS technique it was found, that a more intense coloration of the 2-ethyl-6-methyl-3-hydroxypyridine succinate solution acquires is due to the existence of a quinoid structure of one of tautomers of the starting compound. It is proposed to stabilize drug forms for injection bu adding of 5–8 % of ethanol.
Keywords: gas chromatography; tautomerism; mass spectrometry; dosage form; sample preraration.
References
1. Patent RU 2504376 C1. Vysokostabil’nyy farmatsevticheskiy sostav na osnove liofilizata proizvodnykh 3-oksipiridinov, ili metilpiridinov, ili ikh farmatsevticheski priyemlemykh soley / Sukoyan G.V., Luk’yanova L.D .: zayav. 05.04.2012; opubl. 20.01.2014.
2. Prikaz Ministerstva zdravookhraneniya Rossiyskoy Federatsii ot 31 dekabrya 1996 g. № 432. «Rastvor Meksidola® 5 % dlya in′yektsiy».
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4. Patent RU 2444359 C1. Farmatsevticheskaya kompozitsiya 2-etil-6-metil-3-gidroksipiridina suktsinata dlya peroral’nogo primeneniya i sposob yeyo polucheniya / Zabozlayev A.A., Kovalev V.P.: zayav. 06.12.2010; opubl. 10.03.2012.
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6. Patent RU 2205640 C1. Stabil’nyy farmatsevticheskiy sostav, soderzhashchiy meksidol / Sernov L.N., Skachilova S.Ya.: zayav. 09.04.2020; opubl. 10.11.2003.
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Sakovich M.V., Khaibulina O.Yu., Pavlova N.A.
NMR spectroscopy аpplication for the alkylphosphonic asids detection and identification in OPCW professional test samples
Central Laboratory for Chemical and Analytical Control in the Field of Chemical Disarmament, Federal state unitary enterprise «State Scientific-Research Institute of Organic Chemistry and Technology» State Scientific Center of n Federation. Moscow 111024, Russia

Abstract
A comparative analysis of various one-dimensional and two-dimensional NMR experiments used in the alkylphosphonic acids detection and identification in Organization for the Prohibition of Chemical Weapons (OPCW) professional tests samples is carried out. The necessary duration of experiments for different concentrations of analytes under study is established. A alkylphosphonic acids sequential identification method has been developed. 1D HSQC 1Н–31Р experiment was successfully applied to identify an unknown phosphorus-containing compound in sample of the 46 OPCW test.
Keywords: NMR spectrometry; OPCW professional tests; organophosphorus compounds identification; alkylphosphonic acids.
References
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5. QDOC/LAB/WI/PT02 «Work Instruction for the Preparation of Samples for OPCW Proficiency Tests». Issue № 3. Rev. № 2. Effective date: 11 March 2019. Р. 5.
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