Polyhydric Alcohol Esters of Fatty Acids. Their Preparation, Properties, and Uses.

Goldsmith, H.

doi:10.1021/cr60106a003

Cited by 32 publications

(6 citation statements)

References 85 publications

(156 reference statements)

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“…One possible approach involves the use of recrystallization methods for purification. However, these methods are diffi cult to implement when the glycerides present have sirnilar crystallization temperatures, as is the case for partial esters of glycerol and partial esters of diglycerol [23,24]. Separa tion by silica gel chromatography is widely used in organic chemistry and is the method that best preserves the struc ture of glycerol esters [6,25].…”

Section: Introductionmentioning

confidence: 99%

Structural Analysis of Partial and Total Esters of Glycerol Undecenoate and Diglycerol Undecenoate

Boussambe

Valentin

Mouloungui

2015

J Americ Oil Chem Soc

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The direct esterification reaction between glycerol and undecylenic acid or between diglycerol and undecylenic acid generates all the possible types of glycerol or diglycerol esters. Purification by silica gel chromatography resulted in the isolation of each of these types of ester in a pure form. The molecular structures of the compounds isolated were characterized and identified by mass spectrometry, 1H NMR, 13C NMR and DEPT‐135. We then studied the composition of esters of undecylenic acid formed with glycerol or diglycerol as a function of their reaction conditions, which constitute a highly complex system. We purified undecylenic acid esters from each polyol family to allow the structural identification of each ester of glycerol and each ester of diglycerol with undecylenic acid. We found that the polarity of these non‐ionic amphiphilic esters directly affected their affinity for organic and inorganic solvents and that these esters behaved very differently from anionic amphiphilic molecules, such as undecylenic acid.

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Section: Introductionmentioning

confidence: 99%

Structural Analysis of Partial and Total Esters of Glycerol Undecenoate and Diglycerol Undecenoate

Boussambe

Valentin

Mouloungui

2015

J Americ Oil Chem Soc

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“…The lipases show activities in surfactants and in aroma production and used in cosmetics and perfumeries also. In the presence of lipase a patent Nippon Oil and Fats obtained from for the preparation of propylene glycerol mono fatty acid ester and also used as emulsifier and a pearling agent in cosmetics and foods [ 292 , 293 ]. Novozym 435, derived from Candida antartica is a nonspecific lipase and determined for the enzymatic combination of isopropyl myristate most suitably [ 294 , 295 ].…”

Section: Industrial Applications Of Lipasesmentioning

confidence: 99%

“…Other benefits of microorganisms are high productivity of substrate conversion into product, environmental conditions versatility, and simplicity of genetic operation and in harvesting situations [ 640 ]. Lipases have capabilities to catalyze the same reaction using from different sources, but the microbial lipases are mostly used for biodiesel production like Aspergillus niger , Candida antarctica, Candida rugosa , Chromobacterium viscosum , Mucor miehei , Lactobacillus plantarum, Pseudomonas cepacia , Pseudomonas fluorescens , Photobacterium lipolyticum , Rhizopus oryzae , Streptomyces sp., and Thermomyces lanuginose, Burkholderia cepacia, Bacillus subtilis Q1 KX712301 [ 293 , 641 ]. Candida rugosa yeast is mostly used for lipase production.…”

Section: Industrial Applications Of Lipasesmentioning

confidence: 99%

Microbial lipases and their industrial applications: a comprehensive review

et al. 2020

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Lipases are very versatile enzymes, and produced the attention of the several industrial processes. Lipase can be achieved from several sources, animal, vegetable, and microbiological. The uses of microbial lipase market is estimated to be USD 425.0 Million in 2018 and it is projected to reach USD 590.2 Million by 2023, growing at a CAGR of 6.8% from 2018. Microbial lipases (EC 3.1.1.3) catalyze the hydrolysis of long chain triglycerides. The microbial origins of lipase enzymes are logically dynamic and proficient also have an extensive range of industrial uses with the manufacturing of altered molecules. The unique lipase (triacylglycerol acyl hydrolase) enzymes catalyzed the hydrolysis, esterification and alcoholysis reactions. Immobilization has made the use of microbial lipases accomplish its best performance and hence suitable for several reactions and need to enhance aroma to the immobilization processes. Immobilized enzymes depend on the immobilization technique and the carrier type. The choice of the carrier concerns usually the biocompatibility, chemical and thermal stability, and insolubility under reaction conditions, capability of easy rejuvenation and reusability, as well as cost proficiency. Bacillus spp., Achromobacter spp., Alcaligenes spp., Arthrobacter spp., Pseudomonos spp., of bacteria and Penicillium spp., Fusarium spp., Aspergillus spp., of fungi are screened large scale for lipase production. Lipases as multipurpose biological catalyst has given a favorable vision in meeting the needs for several industries such as biodiesel, foods and drinks, leather, textile, detergents, pharmaceuticals and medicals. This review represents a discussion on microbial sources of lipases, immobilization methods increased productivity at market profitability and reduce logistical liability on the environment and user.

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“…The original method of the selective synthesis of monoesters using boric acid was reported by Hartman, but this method is of little preparative significance [11]. Many of the esterification reactions are carried out at elevated temperatures in presence of homogeneous acidic, amphoteric or basic catalysts [12]. Sodium or potassium hydroxide or p -toluenesulphonic acid are the most preferred catalysts.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

Nowicki

Woch

Mościpan

et al. 2017

J Surfact & Detergents

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The synthesis of selected polyoxyethylene–polyoxypropylene block copolymer (poloxamer) fatty acid monoesters is presented. Organotin homogeneous catalyst Sn bis(2-ethylhexanoate) effectively catalyzed the esterification reaction of (EO)–(PO)–(EO) block copolymer (poloxamer) with fatty acids. The reaction proceeded in high yield and high selectivity to monoesters. Content of diesters in final products was below 1 wt%. The new protocol opened up a high yield and high selective method for the synthesis of poloxamer fatty acid monoesters. These products are potentially interesting for industrial applications, e.g. in lubricants, cosmetics and, in particular, as potential emulsifying agents compatible with hydrocarbon bases, such as paraffin.Electronic supplementary materialThe online version of this article (doi:10.1007/s11743-017-2020-2) contains supplementary material, which is available to authorized users.

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Polyhydric Alcohol Esters of Fatty Acids. Their Preparation, Properties, and Uses.

Cited by 32 publications

References 85 publications

Structural Analysis of Partial and Total Esters of Glycerol Undecenoate and Diglycerol Undecenoate

Structural Analysis of Partial and Total Esters of Glycerol Undecenoate and Diglycerol Undecenoate

Microbial lipases and their industrial applications: a comprehensive review

Selective Synthesis of Polyoxyethylene–Polyoxypropylene Block Copolymer (Poloxamer) Fatty Acid Monoesters Over Homogeneous Organotin Catalyst

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