Synthesis of Ricinoleic Acid Estolides by the Esterification of Ricinoleic Acids Using Functional Acid Ionic Liquids as Catalysts

Wang, Gaoshang; Sun, Shangde

doi:10.5650/jos.ess17031

Cited by 20 publications

(14 citation statements)

References 20 publications

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“…Considering protic acids have catalytic effects on the esterification reaction, we designed and synthesized a series of ILs containing protic anions as shown in Scheme 2. With the synthesized ILs as catalyst, the ricinoleic acid esterification was performed and the catalytic activity of these functional ILs was evaluated with the acid value of the product as it is a convenient index to monitor the degree of oligomerization by reflecting the concentration of carboxy groups in the system, which has been cross verified by HPLC method [19,28].…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, the thermal stability and negligible vapor pressure of ILs can facilitate the product separation after reaction. To the best of our knowledge, the IL 1-butylsulfonic-3methylimidazolium tosylate ([HSO 3 -BMim]TS) can be used as catalyst in the synthesis of oligomeric ricinoleic acid, the estolide with an acid value of 48 ± 2.5 mg KOH/g was obtained after 14 h [28]. Nevertheless, the product separation and catalyst reusability have not yet been investigated until now.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

You¹,

He²,

Gao³

et al. 2020

Beilstein J. Org. Chem.

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Raw material from biomass and green preparation processes are the two key features for the development of green products. As a bio-lubricant in metalworking fluids, estolides of ricinoleic acid are considered as the promising substitute to mineral oil with a favorable viscosity and viscosity index. Thus, an efficient and sustainable synthesis protocol is urgently needed to make the product really green. In this work, an environment-friendly Brønsted acidic ionic liquid (IL) 1-butanesulfonic acid diazabicyclo[5.4.0]undec-7-ene dihydrogen phosphate ([HSO3-BDBU]H2PO4) was developed as the efficient catalyst for the production of oligomeric ricinoleic acid from ricinoleic acid under solvent-free conditions. The reaction parameters containing reaction temperature, vacuum degree, amount of catalyst and reaction time were optimized and it was found that the reaction under the conditions of 190 °C and 50 kPa with 15 wt % of the [HSO3-BDBU]H2PO4 related to ricinoleic acid can afford a qualified product with an acid value of 51 mg KOH/g (which corresponds to the oligomerization degree of 4) after 6 h. Furthermore, the acid value of the product can be adjusted by regulating the reaction time, implying this protocol can serve as a versatile method to prepare the products with different oligomerization degree and different applications. The other merit of this protocol is the facile product separation by stratification and decantation ascribed to the immiscibility of the product and catalyst at room temperature. It is also worth mentioning that the IL catalyst can be used at least for five cycles with high catalytic activity. As a result, the protocol based on the IL catalyst, i.e. [HSO3-BDBU]H2PO4 shows great potential in industrial production of oligomeric ricinoleic acid from ricinoleic acid.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

You¹,

He²,

Gao³

et al. 2020

Beilstein J. Org. Chem.

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“…ChCl‐ZnCl 2 exhibited the highest activity of 98% oleic acid conversion and 80% selectivity of monoestolides. Wang and Sun () compared different ionic liquid catalysts, including 1‐butylsulfonic‐3‐methylimidazolium tosylate [BSO 3 HMIM]TS, 1‐butylsulfonic‐3‐methylimidazolium hydrogen sulfate [BSO 3 HMIM]HSO 4 , 1‐butylsulfonic‐3‐methylimidazolium trifluoromethanesulfonate [BSO 3 HMIM]OTF, and 1‐butylsulfonic‐3‐methylimidazolium hydrophosphate [BSO 3 HMIM]HPO 4 for the synthesis of ricinoleic acid estolides. Among the tested ionic liquids, [BSO 3 HMIM]TS showed the best performance and gave a final acid number of 48 under the optimized synthesis conditions.…”

Section: Synthesis Of Fatty Acid Estolidesmentioning

confidence: 99%

Fatty Acid Estolides: A Review

Chen

Biresaw

Cermak

et al. 2020

J Americ Oil Chem Soc

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Estolides are bio‐based oils synthesized from fatty acids or from the reaction of fatty acids with vegetable oils. Estolides have many advantages as lubricant base oils, including excellent biodegradability and cold flow properties. Promising applications for estolides include bio‐lubricant base oils and in cosmetics. In this review, the synthesis of estolides from fatty acids using four different types of catalysts, namely, mineral acids, solid acids, lipases, and ionic liquids, is summarized. The summary includes the yield of estolide obtained from varying synthetic conditions (time, temperature, catalyst). Also reviewed are studies comparing the physical properties of estolides synthesized from refined fatty acids against those synthesized from fatty acid mixtures obtained from vegetable oils such as coconut, castor, Physaria, etc. By varying the structure of the fatty acids, estolides with a wide range of pour point, cloud point, and viscosity are synthesized to meet a wide range of application requirements. Currently, estolide products are being commercialized for personal care and lubricant base oils for automotive, industrial, and marine applications. The application areas and the demand for estolides is expected to grow as the drive for switching from petroleum to bio‐based products keeps growing.

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“…Estolides can be prepared from hydroxy fatty acids by esterification (Figure 1), or from unsaturated fatty acids by the acid-catalyzed addition to the double bond [7][8][9]. Harsh conditions can however result in colored products and undesired side reactions that would require extra costs for purification.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Estolides from Castor Oil

2020

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Estolides are fatty acid polyesters with applications in both industry and consumer products. Recently, reports have emerged detailing lipase-catalyzed synthesis of estolides from free hydroxy fatty acids. In this paper, we describe a simple alternative enzymatic process, in which castor oil is directly converted to an estolide mixture by Candida antarctica lipase A (CALA) catalyzed transesterification. The reaction mixture is analyzed by NMR to determine the estolide number (EN) and MALDI MS to identify individual components, in addition to titration to determine the acid value (AV). Estolide trimers and tetramers (EN 2–3) were formed over 24 h in a system with 2:1 (v/v) castor oil–water. Further, utilizing different lipase specificities, addition of Thermomyces lanuginosus lipase (TLL), allowed the CALA product mixture to be cleaned up by hydrolyzing attached glycerol. In addition, a three-enzyme process is suggested, in which a simple alcohol is added and Candida antarctica lipase B (CALB) is used to esterify carboxylic acids to lower AV.

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Synthesis of Ricinoleic Acid Estolides by the Esterification of Ricinoleic Acids Using Functional Acid Ionic Liquids as Catalysts

Cited by 20 publications

References 20 publications

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

Fatty Acid Estolides: A Review

Enzymatic Synthesis of Estolides from Castor Oil

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