Published January 2026, Pg. 51-56

Section: Oil refining and petroleum chemistry

UOT: 665.612.2-027.22

DOI: 10.37474/0365-8554/ 2026-01-51-56

Synthesis and characterization of diethylene glycol bis-dibenzoate and diethylene glycol bis-p-dichlorobenzoate esters in the presence of perchloric acid catalyst

O.M. Alasgarova PhD in Ch. Sc. - Institute of Petrochemical processes

P.M. Kerimov PhD in Ch. Sc. - Institute of Petrochemical processes

G.G. Nasibova PhD in Ch. Sc. - Institute of Petrochemical processes

S.G. Alieva Dr. in Tech. Sc. - Institute of Petrochemical processes

E.M. Guliyeva PhD in Ch. Sc. - Institute of Petrochemical processes

Kh.V. Hajizade - Institute of Petrochemical processes

The article synthesizes diethylene glycol bis-dibenzoate esters based on benzoic acid and diethylene glycol in the presence of perchloric acid catalyst, as well as diethylene glycol bis-p-dichlorobenzoate based on p-chlorobenzoic acid and diethylene glycol in the presence of 70 % perchloric acid at 110–120 oC for 4–5 hours with yields of 78–91 %. The physicochemical properties of the synthesized esters were determined by analytical and spectral methods. The synthesized esters were tested as antioxidants that improve the thermal-oxidative stability of hydrotreated diesel fuel. Two samples were prepared by adding 0.004 % D/F to each of the synthesized esters. The samples prepared for improving the properties of D/F were tested in the Jet and Diesel Fuels Laboratory of the National Research Institute of Petroleum Engineering. The test was carried out in the LSART apparatus at 120 oC for 4 hours with a copper plate, and the results are presented. Based on the results obtained, it can be said that adding esters at a concentration of 0.004 % in 100 ml of D/F at 120 oC reduced the amount of sediment from 4.1 mg to 1.2 mg and 0.9 mg. Heteroaromatic esters of ethylene glycol can be used as high-quality antioxidant additives in diesel fuel.

References:

1. Kerimov P.M., Alesgerova O.M., Saadova L.M., Nasibova G.G., Guliyeva E.M. Ion mayesi katalizatorunun ishtiraki ile etilenglikolun bis-dibenzoat-, bis-p-dikhlordibenzoat efirlerinin sintezi // Azerbaijan neft teserrufaty, 2022, № 9, s. 55-59.

2. Alesgerova O.M., Kerimov P.M., Aliyeva S.G., Chingiz F.Ch. Perkhloratturshu katalizatorunun ishtiraki ile etilenglikolun-naftenat-p-nitrobenzoat efirinin sintezi ve tedgigi / “Muasir tebiet ve igtisad elmlerinin aktual problemleri” adlı Beynelkhalq elmi konfransy, Gence Dovlet Universiteti, 3-4 may 2024, s. 316-319.

3. Kerimov P.M., Alesgerova O.M., Afandiyeva L.M., Aliyeva S.G., Jafarova A.A. Ion mayesi katalizatorunun ishtiraky ilə etilenglikolun-bis-α-dinaftildiasetat efirinin sintezi və tedgigi / Emekdar Elm Khadimi Akif Hemid oghlu Azizovun 80 illik yubileyine hesr olunmush elmi konfrans, 15 noyabr 2023, s. 164.

4. Kerimov P.M., Elesgerova O.M., Afandiyeva L.M., Guliyeva E.M., Musayeva A.P., Jafarova A.A. Nano-ZnO katalizatorlarının ishtiraky ile etilenglikolun-bis-dihippurat, bis-dianisat efirlerinin sintezi ve tedgigi // Azerbaycan neft teserrufati, 2024, № 2, s. 62-67.

5. Sadiyeva N.F., Nasibova G.G., Afandiyeva L.M., Guliyeva E.M., Mammadova S.A., Mammadova Kh.R. Etilenglikolun geyri-simmetrik diefirlgrinin sintezi ve tedgigi // Azerbaycan neft teserrufati, 2024, № 11, s. 44-51.

6. Sadiyeva N.F., Nasibova G.G., Iskenderova S.A., Efendiyeva L.M., Cherepnova Yu.P., Aliyeva S.G., Maza-
mova T.A. Synthesis and study of mixed diesters of synthetic petroleum acids and fatty acids // Russian Journal of Applied chemistry, 2023, vol. 96, No. 4, pp. 417-421.

7. Abbasov V.M., Afandiyeva L.M., Nasibova G.G., Sadiyeva N.F., Lyadov A.S., Guliyeva E.M. Synthesis and investigation of ethylene glycol monoesters of synthetic petroleum acids // ISSN 0965-5441, Petroleum Chemistry © Pleiades Publishing, Ltd., 2025.

8. Guang B., Wu Y., Liu W. et al. Kinetics Study of the Esterification Reaction of Cyclohexene to Cyclohexyl Acetate Catalyzed by Novel Bronsted–Lewis Acids Bifunctionalized Heteropolyacid Based Ionic Liquids Hybrid Solid Acid Catalysts. Catal Lett, 2022,152, pp. 75-86.

9. Yunfeng Zhu, Liang Gao, Langyou Wen, Baoning Zong, Hao Wang, Minghua Qiao. Cyclohexene esterification–hydrogenation for efficient production of cyclohexanol. Green Chem., 2021, Issue 3, 23, pp. 1185-1192.

10. Domingues LACS, Carriello GM, Pegoraro GM, Mambrini GP. Synthesis of TiO2 nanoparticles by the solvothermal method and application in the catalysis of esterification reactions. An Acad Bras Cienc. 2024, 96
(suppl 3):e20240096.