Estolide production with modified clay catalysts and process conditions

Erhan, Selim M.; Isbell, Terry A.

doi:10.1007/s11746-997-0131-z

Cited by 15 publications

(9 citation statements)

References 18 publications

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“…Use of industrial clays as catalysts resulted in low and impractical yields of estolides (2)(3)(4). Mineral acid catalysis, on the other hand, gave good to excellent estolide yields (1,(5)(6) and formed the basis of this process.…”

mentioning

confidence: 99%

Synthesis of estolide esters from cis‐9‐octadecenoic acid estolides

kuru¹,

Isbell²,

Weisleder³

2001

J Americ Oil Chem Soc

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Oleic acid (cis-9-octadecenoic acid ) was converted in excellent yield to the estolide, which was then esterified with 2,2-dimethypropan-1-ol (neopentyl alcohol), cis-9-octadecen-1-ol (oleyl alcohol), and 2-propanol to generate the corresponding estolide esters. Higher-formula mass estolide esters were synthesized by reaction of the parent estolide with 1,3-propanediol, 2,2-dimethyl-1,3-propanediol, and 1,5-pentanediol to give the corresponding diesters of oleic estolide, thus doubling the molecular size of the parent estolide. Pour points and viscosities were determined in order to evaluate these products for possible industrial application.Paper no. J9441 in JAOCS 78, 219-222 (March 2001).KEY WORDS: 2,2-Dimethyl-1,3-propanediol, 2,2-dimethylpropan-1-ol, 2,2-dimethyl-1,3-propyl diester, esterification, neopentyl ester, cis-9-octadecenioc acid (oleic acid), cis-9-octadecen-1-ol, oleic estolide, oleyl ester, 1,5-pentanediol, 1,5-pentyl diester, perchloric acid, phosphoric acid, 1,3-propanediol, 2-propanol, 1,3-propyl diester, 2-propyl ester, sulfuric acid.

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mentioning

confidence: 99%

Synthesis of estolide esters from cis‐9‐octadecenoic acid estolides

kuru¹,

Isbell²,

Weisleder³

2001

J Americ Oil Chem Soc

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“…The literature can be confusing in that for the earlier work, determining the structures in the complex reaction mixture was difficult since sophisticated analytical methods were not available to these researchers. The analysis is also complicated due to formation of lactones, hydroxyl FA, and inter-esters by addition of the carboxylic acid across the olefinic bond, in addition to the branched monomers, and dimers, trimers, and higher-molecular-weight products with different structures [ 22 , 38 , 41 ]. Even though distillation methods are difficult because of the high molecular weights and viscosity of the components, distillations can separate monomeric forms of dimeric and polymeric products, even using wiped-film evaporators.…”

Section: Fatty Acid Dimer Synthesis and Propertiesmentioning

confidence: 99%

“…Among the by-products of the dimerization reaction is the unwanted formation of inter-esters, also referred to as an estolide, that have been discussed even in the first patents on the dimerization process using a clay catalyst [ 20 , 21 , 41 ]. This reaction involves the addition of the carboxylic acid of one FA across the olefinic bond of another FA molecule.…”

Section: Fatty Acid Dimer Synthesis and Propertiesmentioning

confidence: 99%

Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids

Frihart

2023

Polymers

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While there is abundant literature on using a wide range of biomaterials to make polymers for various adhesive applications, most researchers have generally overlooked developing new adhesives from commercially available bio-based dimerized fatty acids. Some of the literature on the chemistry taking place during the clay-catalyzed dimerization of unsaturated fatty acids is generally misleading in that the mechanisms are not consistent with the structures of these dimers and a by-product isostearic acid. A selective acid-catalyzed interlayer model is much more logical than the widely accepted model of clay-catalyzed Diels–Alder reactions. The resulting dimers have a variety of linkages limiting large crystal formation either as oligomeric amides or polyamides. These highly aliphatic fatty acid dimers are used to make a wide range of hot melt polyamide adhesives. The specific structures and amounts of the diacids and diamines and their relative ratios have a big effect on the bio-based polyamide mechanical properties, but analysis of the structure–property relationships has seldom been attempted, since the data are mainly in the patent literature. The diacids derived from plant oils are valuable for making polyamides because of their very high bio-based content and highly tunable properties.

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“…Unlike homogeneous catalysts, the application of heterogenous catalysts for estolide synthesis has several advantages such as recyclability and easy separation, which is highly desirable in industrial products. Erhan and Isbell () reported the application of modified clay catalysts to produce estolides from meadowfoam fatty acid and oleic acid. The esterification reaction was catalyzed by acidic sites on the clay.…”

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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Estolide production with modified clay catalysts and process conditions

Cited by 15 publications

References 18 publications

Synthesis of estolide esters from cis‐9‐octadecenoic acid estolides

Synthesis of estolide esters from cis‐9‐octadecenoic acid estolides

Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids

Fatty Acid Estolides: A Review

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