Green Process without Thinning Agents for Preparing Sebacic Acid via Solid-Phase Cleavage

Yu, Siyuan; Cui, Jianlan; Zhong, Congshan; Meng, Jian; Xue, Tianyi

doi:10.1021/acsomega.9b00577

Cited by 11 publications

(12 citation statements)

References 24 publications

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“…Alkaline strength is an important factor in alkali fusion, the previous research has confirmed that stronger alkalinity is beneficial for the formation of sebacic acid (Yu et al, ). Nevertheless, from the perspective of economy, low‐cost NaOH was used for preparing sebacic acid in this study.…”

Section: Resultsmentioning

confidence: 95%

“…At present, although some new methods regarding preparing sebacic acid have been reported, the disadvantages hamper their further application. For microwave‐induce (Azcan and Demirel, ) and solid‐phase cleavage (Yu et al, ), despite obtaining high yield of sebacic acid, cannot be further utilized into industrialization due to limitations of the reactor. In addition, electrolytic adipic acid (Mathieu, ) and microbial fermentation (Liu and Gao, ) also cannot be used for large‐scale industrial production.…”

Section: Introductionmentioning

confidence: 99%

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

Cui

Wang

et al. 2020

J Americ Oil Chem Soc

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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.

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Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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

Cui

Wang

et al. 2020

J Americ Oil Chem Soc

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“…In 2015, sebacic acid emerged as the highest consumed derivative of castor oil. 61 A product can be manufactured via different routes, but not all are commercially feasible. Similarly, there are different methods of production, but the caustic fusion of castor oil is used on an industrial scale for the production of sebacic acid.…”

Section: Sebacic Acidmentioning

confidence: 99%

“…The major companies producing sebacic acid in China having a production capacity of over 40,000 tons per year are Hebei Hengshui Jinghua Chemical Co., Ltd. and Hebei Kaide Biomaterials Co., Ltd. In 2015, sebacic acid emerged as the highest consumed derivative of castor oil 61 …”

Section: Commercially Vital Derivatives Of Castor Oilmentioning

confidence: 99%

A comprehensive review of castor oil‐derived renewable and sustainable industrial products

Singh

Sharma

Sarma

et al. 2022

Env Prog and Sustain Energy

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Castor oil is one important raw material that could serve as a renewable feedstock for industries in the age of exhausting fossil fuels. The chemical composition of oil and the structure of hydroxyl fatty acid are responsible for its unique physicochemical properties. The oil has diverse applications from pharmaceuticals to polyamides, from the manufacturing of ski boots to durable frames, and from lubricants to laxatives. The present review gives an insight into the physicochemical properties of castor oil and its application. The oil is used for the production of a great variety of its derivatives. Out of many derivatives of castor oil, four are produced and utilized at a larger scale. The names of the four derivates are ricinoleic acid, sebacic acid, undecylenic acid, and γ-decalactone. The review will aim toward an insight into the evolved techniques for the manufacturing of these derivatives of castor oil, the biotechnological route of production, and metabolic engineering approaches. Though the industrial significance of castor oil and its derivatives had been known for ages, methods for their production are continuously changing.

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“…[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. [17] However, research in this area for producing sebacic acid from castor oil is active due to its huge demand in oleochemical and other industries. In this regard, we attempted to synthesize sebacic acid from castor oil by designing a synthetic route with well-known reagents with a view to explore an alternate route for sebacic acid as India is a major producer of castor oil.…”

Section: Introductionmentioning

confidence: 99%

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

Bhukya

Kaki

2022

Euro J Lipid Sci & Tech

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A simple and alternate organic synthetic route for sebacic acid, a high value ten‐carbon aliphatic dicarboxylic acid from castor oil is described in this study. Castor oil methyl esters are purified to obtain methyl ester of ricinoleic acid that is used as the starting material for the preparation of sebacic acid. The hydroxyl group of methyl ricinoleate is oxidized to corresponding 12‐oxo derivative followed by isomerization of the cis 9, 10 olefinic bond to trans 10, 11 isomer. The isomerized compound is subjected to dihydroxylation followed by oxidative cleavage and subsequent methylation to obtain dimethyl decanedioate. The dimethyl decanedioate is finally hydrolyzed to obtain sebacic acid. The intermediate compounds and final product are purified and characterized by chromatographic and spectral analysis. The final compound is analyzed by 1H and 13C‐NMR as well as high resolution mass spectrometry and compared with standard compound for the confirmation of the structure. Practical Applications: The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated.

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Green Process without Thinning Agents for Preparing Sebacic Acid via Solid-Phase Cleavage

Cited by 11 publications

References 24 publications

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

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

A comprehensive review of castor oil‐derived renewable and sustainable industrial products

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

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