Synthesis of nitrogen-containing derivatives of alkenyl succinic acid and their functional properties in diesel fuels of different compositions
https://doi.org/10.21285/achb.962
EDN: WBDOPA
Abstract
The study was aimed at synthesizing amides of different structures and their subsequent testing as paraffin dispersants in hydrotreated summer diesel fuels of different hydrocarbon compositions together with a depressor additive based on ethylene and vinyl acetate copolymer. The following parameters were determined for the hydrotreated base summer diesel fuels under study: molecular weight distribution of n-alkanes, fractional composition, density, kinematic viscosity, low-temperature properties, and sulfur content. The target compounds were synthesized using known procedures. Their structures were confirmed via infrared spectroscopy. For each product, the alkaline and acid numbers were determined using methods described in ASTM standards. The low-temperature parameters were estimated according to the known procedures given in ASTM standards, domestic state standards, as well as STO 11605031-041-2010 of the All-Russian Research Institute for Oil Refining. For the obtained diesel fuel samples, including those containing the additive, the following low-temperature properties were determined: pour point, cloud point, cold filter plugging point, as well as sedimentation stability under cold storage conditions. The amides synthesized in this work were found to improve the low-temperature properties of fuels depending on their alkenyl radical, as well as the composition of the analyzed diesel fuel; in particular, they increase the sedimentation stability under cold storage conditions. The article studied the dependence of the dispersing properties of synthesized amides on their structure and the molecular weight distribution of n-alkanes in the base summer diesel fuels.
About the Authors
A. D. Tubeltseva
Gubkin University
Russian Federation
Russian Federation
Anna D. Tubeltseva, Postgraduate Student
65, Lenin Ave., Moscow, 119991
L. V. Ivanova
Gubkin University
Russian Federation
Russian Federation
Lyudmila V. Ivanova, Dr. Sci. (Chemistry), Professor, Professor
65, Lenin Ave., Moscow, 119991
O. A. Lisechko
Gubkin University
Russian Federation
Russian Federation
Olesya A. Lisechko, Laboratory Assistant
65, Lenin Ave., Moscow, 119991
References
1. Kameshkov A.V., Gaile A.A. Production of diesel fuels with improved low temperature properties (review). Bulletin of the Saint Petersburg State Institute of Technology (Technical University). (In Russian). 2015;29:49-60. DOI: 10.15217/issn998984-9.2015.29.49. EDN: UDOGPB.
2. Afanas’ev I.P., Alekseev S.Z., Ishmurzin A.V., Lebedev B.L., Talalaev S.Yu. Development of industrial technology of the winter diesel fuel production with the sequential combination of the processes of deparaffination on the catalyst SGK-1 and the hydro-desulfurization on the catalyst of KGU-950. Neftepererabotka i neftekhimiya. Nauchno-tekhnicheskie dostizheniya i peredovoi opyt. 2014;(4):3-6. (In Russian). EDN: SFOADJ.
3. Buzyreva E.D., Smyshlyaeva K.I. Paraffin dispersants for diesel fuel. Aktualnye problemy nauki i tekhniki – 2022: materialy XV Mezhdunar. nauch-prakt. konf. molodykh uchenykh i spetsialistov = Current issues of science and technology –2022: Proceedings of the XVth International Scientific Conference of Young Scientists and Specialists. Ufa: Ufa State Petroleum Technological University; 2022, vol. 1, p. 116-117.
4. Sun M., Rezaei N., Firoozabadi A. Mitigating paraffin wax deposition by dispersants and crystal modifiers in flow testing. Fuel. 2022;324:124687. DOI: 10.1016/j.fuel.2022.124687.
5. Rudyak K.B., Polyanskii K.B., Vereshchagina N.V., Zemtsov D.B., Panov D.M., Yumasheva T.M. Depressant and dispersant additives for diesel fuel. Components, brands, new technologies and developments. Chemistryand Technology of Fuels and Oils. 2022;58:741-748. DOI: 10.1007/s10553-022-01444-x.
6. Iovleva E.L. Use of a depressant-dispersant additive during storage of diesel fuel. IOP Conference Series: Earth and Environmental Science. 2022;990:012003. DOI: 10.1088/1755-1315/990/1/012003.
7. Yang T., Yin S., Xie M., Chen F., Su B., Lin H., et al. Effects of N-containing pour point depressants on the cold flow properties of diesel fuel. Fuel. 2020;272:117666. DOI: 10.1016/j.fuel.2020.117666.
8. Yakovlev N.S., Agaev S.G. Influence of physicochemical properties of depressor additives on their performance in diesel fuels. Proceedings of Universities. Applied Chemistry and Biotechnology. 2022;12(4):612-619. (In Russian). DOI: 10.21285/2227-2925-2022-12-4-612-619. EDN: YBJNUE.
9. Ivanova L.V., Makarov I.A., Sorokina A.S., Burov E.A., Primerova O.V., Koshelev V.N. Comparative study of the depressant-dispersant additives efficiency in diesel fuel. ChemChemTech. 2022;65(3):60-66. (In Russian). DOI: 10.6060/ivkkt.20226503.6446. EDN: ORMIIF.
10. Danilov A.M. A new look at fuel additives (review). Neftekhimiya. 2020;60(2):163-171. (In Russian). DOI: 10.31857/S0028242120020033. EDN: HQREHE.
11. Kurzin A.V., Evdokimov A.N. Pour point depressants for fuels based on tall oil fatty acid esters. Izvestia SanktPeterburgskoj lesotehniceskoj akademii. 2021;237:196-203. (In Russian). DOI: 10.21266/2079-4304.2021.237.196-203. EDN: EMLYEK.
12. Tubeltseva A.D., Ivanova L.V., Donskaya E.S., Koshelev V.N. Synthesis and study of oleic acid amides in the summer diesel fuels. Oil and Gas Technologies. 2022;6:23-28. (In Russian). DOI: 10.32935/1815-2600-2022-143-6-23-28. EDN: BRXGHG.
13. Maithufi M.N., Joubert D.J., Klumperman B. Application of gemini surfactants as diesel fuel wax dispersants. Energy & Fuels. 2011;25(1):162-171. DOI: 10.1021/ef1006287.
14. Wenderoth B., Hermeling D. Paraffin dispersants with a lubricity effect for distillates of petroleum products. Patent USA, no. 6786940B1; 2000.
15. Marie E., Chevalier Y., Brunel S., Eydoux F., Germanaud L., Flores P. Settling of paraffin crystals in cooled middle distillate fuels. Journal of Colloid and Interface Science. 2004;269(1):117-125. DOI: 10.1016/j.jcis.2003.07.030.
16. Rudnick L.R. Lubricant additives. Chemistry and applications. CRC Press; 2003, 758 p. (Russ. ed.: Prisadki k smazochnym materialam: svoistva i primenenie. Saint Petersburg: Professiya; 2013, 927 p.).
17. Savelenko V.D., Ershov M.A., Makhova U.A., Makhmudova A.E., Podlesnova E.V., Nizovtsev A.V., et al. Analysis of the fuel additives market in Russia and prospects for import substitution. Oil & Gas Chemistry. 2023;2:12-19. (In Russian). DOI: 10.24412/2310-8266-2023-2-12-19. EDN: ISUWWF.
18. Isayev N.Z., Javadova N.A. Synthesis, properties and areas of application of alkenylsuccinic anhydrides. News of the Tula state university. Natural sciences. 2024;1:3-20. (In Russian). DOI: 10.24412/2071-6176-2024-1-3-20. EDN: EWKMPL.
19. Kuzmenko M.F., Davletshin A.R., Kuzmenko F.F., Khamzin Yu.A., Shiriyazdanov R.R., Hairutdinov I.R., et al. Synthesis alkenyl succinimide dispersant to ensure compliance with motor oil modern environmental and operational requirements. Innovatics and Expert Examination. 2015;2:80-91. (In Russian). EDN: VQZZYD.
20. Wenderoth B., Uzelac L., Faul D., Dralle-Voss G. Paraffin dispersants for crude oil middle distillates. Patent USA, no. 6071993A; 2000.
Review
For citations:
Tubeltseva A.D., Ivanova L.V., Lisechko O.A. Synthesis of nitrogen-containing derivatives of alkenyl succinic acid and their functional properties in diesel fuels of different compositions. Proceedings of Universities. Applied Chemistry and Biotechnology. 2025;15(1):119-127. (In Russ.) https://doi.org/10.21285/achb.962. EDN: WBDOPA
Views:
73
Email this article 