Preparation of Sebacic Acid via Alkali Fusion of Castor Oil and its Several Derivatives

Abstract

Castor oil and its three derivatives including methyl ricinoleate, sodium ricinoleate and ricinoleic acid were used as the raw material for alkali fusion to prepare sebacic acid. The reaction parameters including catalyst, ratio of oleochemicals/NaOH, reaction time and reaction temperature were optimized. It was found that Pb3O4 (1%) showed the best catalytic performance, and 553 K was considered as the most suitable reaction temperature. The oleochemicals/NaOH ratios of 15:14, 15:14, 15:12 and 15:14 were determined as the optimal ratio for alkali fusion of castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid, respectively. In addition, the optimal reaction time of alkali fusion of castor oil was 5 hours, and that of its derivatives was 3 hours. The maximum yield in sebacic acid of 68.8%, 77.7%, 80.1%, 78.6% can be obtained by using castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid as the raw material, respectively. High purity of sebacic acid was confirmed by GC and melting point analysis. ICP‐OES results illustrated that the content of Pb in sebcic acid was less than 1 mg kg−1. Separating glycerol from castor oil was beneficial for alkali fusion, by which, the yield of sebacic acid was increased of approximately 10%, and the reaction time was reduced from 5 to 3 hours. This study provided guiding significance for the future industrial production of sebacic acid.

Design and Synthesis of Sebacic Acid from Castor Oil by New Alternate Route

“…R f : 0.55 in 10% EtOAc in hexane. 1 H NMR (400 MHz, CDCl 3 ) 𝛿 6.82 (d, J = 15.8, 6.9 Hz, 1H), 6.09 (d, J = 15.9, 1.5 Hz, 1H), 3.67 (s, 3H), 2.55 -2.50 (m, 2H), 2.31 (t, J = 7.5 Hz, 2H), 2.23 -2.17 (m, 2H), 1.67 -1.23 (m, 18H), 0.89 (t, J = 8.9 Hz, 3H);); 13…”

“…R f : 0.6 in 10% EtOAc in hexane. 1 H NMR (400 MHz, CDCl 3 ) 𝛿 5.45-5.65 (m, 2H), 3.67 (s,3H), 3.15 (d, J = 6.2 Hz, 1H), 2.43 (t, J = 7.5 Hz, 1H), 2.30 (t, J = 7.5 Hz, 1H), 2.02 (q, J = 6.6 Hz, 1H), 1.64 -1.26 (m, 5H), 0.89 (t, J = 8.9 Hz, 3H); 13…”

“…The alkali fusion method was modified recently where it was reported that when sodium ricinoleate was used, an increased yield of sebacic acid (80.1%) was observed compared to other starting materials like castor oil, methyl ricinoleate, and ricinoleic acid. [13] The other reported methods include microwave induced alkali fusion of castor oil methyl ester with lead tetroxide, microbial biotransformation using Candida tropicalis, retro-aldolases and oleate hydratase. [14][15][16] In a recent study sebacic acid was produced in a tubular furnace reactor at a temperature of 270 °C using sodium ricinoleate and potassium hydroxide as raw materials and ferric oxide as catalyst.…”

Synthesis and characterization of bio‐based polyesters derived from 1,10‐decanediol

“…To solve the above environmental pollution problems, three derivatives of castor oil without glycerol (methyl ricinoleate, sodium ricinoleate and ricinoleic acid) were used to prepare sebacic acid in 2020. 25 For methyl ricinoleate, ricinoleic acid, and sodium ricinoleate, 77.7% yield (97.8% purity), 78.6% yield (98.0% purity) and 80.1% yield (97.5% purity) can be obtained, respectively. 1,10-Decanediol (DD) can be obtained by oxidation of sebacic acid.…”

“…When castor oil is directly used as a raw material, the glycerol in castor oil can be decomposed into acrolein at high temperature, which will pollute the environment. To solve the above environmental pollution problems, three derivatives of castor oil without glycerol (methyl ricinoleate, sodium ricinoleate and ricinoleic acid) were used to prepare sebacic acid in 2020 25 . For methyl ricinoleate, ricinoleic acid, and sodium ricinoleate, 77.7% yield (97.8% purity), 78.6% yield (98.0% purity) and 80.1% yield (97.5% purity) can be obtained, respectively.…”