Synthesis of stabilizers based on glycerides of monocarboxylic acids for industrial chloroparaffins
https://doi.org/10.32362/2410-6593-2022-17-4-298-310
Abstract
Objectives. The study aimed to develop new effective heat stabilizers based on glycerol esters of monocarboxylic acids for industrial chlorinated paraffins and to select of the optimal ratio of active ingredients in the stabilizing composition in order to provide the maximum thermostabilizing effect.
Methods. The thermostabilizing effect of the studied samples on chlorinated paraffins was evaluated according to the standard method for determining the thermal stability of liquid chlorinated paraffins in terms of the mass fraction of split off hydrogen chloride. Quantitative and qualitative analysis of the obtained mixtures of monocarboxylic acid glycerides was carried out using chromato-mass spectrometry.
Results. Glycerides of monocarboxylic acids (oleic, octanoic, hexanoic, and propionic acids) were obtained and identified, and the compositions of the resulting mixtures of mono-, di- and triesters were determined. The stabilizing effect of the obtained mixtures of glycerides of monocarboxylic acids in the amount of 0.5–2.0 wt parts per 100 wt parts of unstabilized industrial chlorinated paraffin CP-30 was determined. The combined use of glycerides of monocarboxylic acids with calcium-containing compounds as a complex stabilizer with a molar ratio of esters/Ca 0.93–0.86/0.07–0.14, respectively, was investigated. Chloroparaffin CP-470, stabilized by the developed complex stabilizer, was successfully used in a polyvinyl chloride composition for cable compound of the brand OM-40.
Conclusions. A proposed variant of a complex stabilizer for chlorinated paraffins based on Russian raw materials for import substitution will expand the range of effective stabilizers for organochlorine substances. Glycerides of monocarboxylic acids are shown to exhibit a thermostabilizing effect on industrial chlorinated paraffins. The relationship between the length of the hydrocarbon substituent of the carboxylic acid in the ester and the thermostabilizing effect is obtained. With an increase in the number of carbon atoms in the hydrocarbon substituent of the carboxylic acid, the heat-stabilizing ability decreases. The minimum sufficient concentration of glycerides of carboxylic acids was 0.05 ± 0.005 mol/kg, above which no increase in the thermostabilizing effect on chloroparaffin was observed. A synergistic ratio of the components of the stabilizing mixture in terms of thermal stability—glycerides of monocarboxylic acids/calcium-containing compounds—was found equal to 0.85–0.9/0.15–0.1.
About the Authors
Yu. L. ZotovRussian Federation
Yuriy L. Zotov, Dr. Sci. (Chem.), Professor, Department of Organic and Petrochemical Synthesis Technology
28, pr. im. V.I. Lenina, Volgograd, 400005
Scopus Author ID 7003371961
RSCI SPIN-code 7543-9740
D. M. Zapravdina
Russian Federation
Daria M. Zapravdina, Assistant, Department of Organic and Petrochemical Synthesis Technology
28, pr. im. V.I. Lenina, Volgograd, 400005
RSCI SPIN-code 2913-1891
E. V. Shishkin
Russian Federation
Evgeniy V. Shishkin, Dr. Sci. (Chem.), Professor, Department of Organic and Petrochemical Synthesis Technology
28, pr. im. V.I. Lenina, Volgograd, 400005
Scopus Author ID 7004314557
RSCI SPIN-code 3280-1800
Yu. V. Popov
Russian Federation
Yuriy V. Popov, Dr. Sci. (Chem.), Professor, Department of Organic and Petrochemical Synthesis Technology
28, pr. im. V.I. Lenina, Volgograd, 400005
Scopus Author ID 26028090100
RSCI SPIN-code 4582-3342
References
1. Zotov Yu.L., Butakova N.A., Popov Yu.V. Okislenie promyshlennykh khlorparafinov kislorodom vozdukha (Oxidation of industrial chlorinated paraffins with atmospheric oxygen). Volgograd: IUNL VolgGTU; 2014. 124 p. (in Russ.).
2. Oshin L.A., Treger Yu.A., Motsarev G.V., Sonin E.V., Sergeev E.V., Skibinskaya M.B., Gol’fand E.A. Promyshlennye khlororganicheskie produkty: spravochnik ( Industrial organochlorine products: handbook). Moscow: Khimiya; 1978. 656 p. (in Russ.).
3. Rysaev U.Sh., Nafikov A.B., Gil’mutdinov A.T., Nafikova R.F., Rysaev V.U. Synergistic stabilizing compositions for chlorine-containing hydrocarbons. Bashkirskii khimicheskii zhurnal = Bashkir Chemical Journal. 2007;14(4):32–36 (in Russ.).
4. Klichkov I.S., Krishtal’ N.F., Nakhimovich M.L., Poselenov A.I., Levanovich V.S., Kharitonov V.I. Method of stabilization of trichlorethylene and perchlorethylene: USSR Pat. 680303. Publ. 27.12.1999 (in Russ.).
5. Tsuyoshi M., Takushi A., Hirota S. Method for stabilizing chlorinated aliphatic hydrocarbon: JP Pat. 2009046444. Prior publ. data 22.08.2007; date of patent 05.03.2009.
6. Krishtal’ N.F., Klichkov I.S. Nakhimovich M.L., Poselenov A.I., Sankov B.G., Sveshnikov A.V., Velichko I.N., Gerasimov F.E. Method for stabilizing methylene chloride: USSR Pat. 1387349. Publ. 27.06.2000 (in Russ.).
7. Rasulev Z.G., Krishtal’ N.F., Nakhimovich M.L., Abdrashitov Ya.M., Rakhimov R.R., Islamshin A.Z. Method of stabilizing 1,2-dichloroethane or 1,2,3-trichloropropane: USSR Pat. 1555321. Publ. 07.04.1990 (in Russ.).
8. No B.I., Zotov Yu.L., Klimov D.S., Shishkin E.V., Klimov S.A., Shatalin Yu.V., Knyazeva E.A. Multifunctional compositions “SINSTAD” for polymers. XVII. Adamantyl derivatives of imic acids as stabilizers of chlorinated paraffins. Plasticheskie massy. 2004;(2):40–41 (in Russ.).
9. Kutyanin L.I., Kuznetsov A.A., Poddubnyi I.S., Ivanova N.A., Sergeev S.A. Method for stabilizing halogenated paraffins: RF Pat. 2245318. Publ. 27.01.2005.
10. No B.I., Zotov Yu.L., Shipaeva T.A., Klimov D.S. Multifunctional compositions “SINSTAD” for polymers. II. Stabilization of chlorinated paraffins KhP-30 with metal stearates. Plasticheskie massy. 1997;(4):41–42 (in Russ.).
11. Minsker K.S., Fedoseeva G.T. Destruktsiya i stabilizatsiya polivinilkhlorida ( Destruction and stabilization of polyvinyl chloride). Moscow: Khimiya; 1979. 272 p. (in Russ.).
12. Quispe C.A.G., Coronado C.J.R., Carvalho J.A. Glycerol: Production, consumption, prices, characterization and new trends in combustion. Renewable and Sustainable Energy Reviews. 2013;27:475–493. https://doi.org/10.1016/j.rser.2013.06.017
13. León-Reina L., Cabeza Au., Rius J., Maireles-Torres P., Alba-Rubio A.C., Granados M.L. Structural and surface study of calcium glyceroxide, an active phase for biodiesel production under heterogeneous catalysis. J. Catal. 2013;300:30–36. http://dx.doi.org/10.1016/j.jcat.2012.12.016
14. Zotov Yu.L., Zapravdina D.M. Method for obtaining plasticiser for polyvinyl chloride composition: RF Pat. 2643996. Publ. 06.02.2018.
Supplementary files
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1. Dependence of the mass fraction of cleaved hydrogen chloride for chlorpapafin CP-30 on the content of carboxylic acid glycerides | |
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Indexing metadata |
- New complex stabilizers based on glycerides of monocarboxylic acids and calcium carboxylates for industrial chlorinated paraffins were developed.
- It was found that monocarboxylic acid glycerides exhibit a thermostabilizing effect on organochlorine compounds, and the minimum sufficient concentration of carboxylic acid glycerides was found to be 0.05 ± 0.005 mol/kg, above which no increase in the thermostabilizing effect on chlorinated paraffin was observed.
- A synergistic ratio of the components of the stabilizing mixture in terms of thermal stability—glycerides of monocarboxylic acids/calcium-containing compounds—was found equal to 0.85–0.9/0.15–0.1.
Review
For citations:
Zotov Yu.L., Zapravdina D.M., Shishkin E.V., Popov Yu.V. Synthesis of stabilizers based on glycerides of monocarboxylic acids for industrial chloroparaffins. Fine Chemical Technologies. 2022;17(4):298-310. https://doi.org/10.32362/2410-6593-2022-17-4-298-310