Processes for the production of triglycerides of unsaturated fatty acids in the presence of enzymes

a technology of unsaturated fatty acids and enzymes, which is applied in the direction of fatty acid esterification, fermentation, etc., can solve the problems of relatively slow reaction time, secondary products and unwanted isomerizations, etc., and achieve the effect of reducing reaction time, reducing reaction rate, and reducing reaction tim

Inactive Publication Date: 2005-10-20
COGNIS IP MANAGEMENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0011] It has surprisingly been found that the reaction of polyunsaturated fatty acids and/or esters thereof with glycerol to form triglycerides can be significantly accelerated by synthesis in vacuo in the additional presence of an additive, entraining agent or glycerol-binding adsorber or by heat treatment of the partial glycerides occurring as intermediate product in the synthesis. The auxiliaries used in addition to the vacuum lead to a significant reduction in the

Problems solved by technology

Chemical syntheses have the disadvantage that very high temperatures generally have to be used and large quantities of basic catalysts are required so that secondary pr

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Lipase Screening for the Synthesis of Triglycerides:

[0021] Various lipases (see Table 1, batches 1 to 9) were immobilized in 9 bottles. To this end, equal quantities of the enzyme preparation and the adsorber resin Amberlite XAD 16 (Rohm & Haas) were shaken overnight at 30° C. in 10 times the quantity of water. The immobilized enzymes were then filtered off and dried overnight on a paper filter.

[0022] In 12 bottles, various immobilized lipases (see Table 1, batches 1-12; batches 1-9 are the lipases immobilized on Amberlite, batches 10-12 are lipase immobilizates produced by the manufacturer) were tested for their ability to synthesize glycerides. To this end, 0.75 g of CLA fatty acid, 0.07 g of glycerol, 2.5 g of t-butanol, 0.5 g of molecular sieve and 0.15 g of each immobilized lipase were weighed in. The closed bottles were incubated for 48 hours at 45° C. on a shaker operating at 200 r.p.m. The content of glycerides formed was analyzed by gas chromatography and evaluated via t...

example 2

Influence of Basic Salts on the Reaction of CLA-Free Acid with Glycerol:

[0031] Glycerol (2.5 g) and CLA fatty acid (27.5 g) were weighed into 8 flasks in a molar ratio of 1:3.6. 0.33% by weight of various salts suspended in the same quantity of water (see Table below) were added to the batches. After addition of 1.25 g of immobilized Candida antarctica B lipase (lipase from Novozymes, Denmark), a vacuum of 20 mbar was applied while stirring with a magnetic stirring fish at a temperature of 60° C. After 17 hours, a sample of the oil phase was removed and the content of reacted CLA fatty acid was determined by determination of the acid value. The starting acid value was 181.

[0032] Results

TABLE 2Acceleration of the reaction of free CLA to CLA triglycerides,as measured from the acid value as a function of the salt addedBatchSaltAcid value1Blank1002Sodium chloride1323Sodium carbonate464Sodium citrate705Sodium acetate536Sodium phosphate647Sodium tartrate1138Sodium tetraborate101

[0033...

example 3

Dependence of Reaction Rate on the Sodium Carbonate Concentration Added

[0034] Glycerol (9 g) and CLA fatty acid (100 g) were weighed into 3 flasks in a molar ratio of 1:3.7. 0.1% sodium carbonate suspended in the same quantity of water was added to batch 2, 1% of sodium carbonate suspended in the same quantity of water was added to batch 3. After addition of 7 g of immobilized Candida antarctica B lipase, a vacuum of 20 mbar was applied while stirring with a magnetic stirring fish at a temperature of 60° C. Samples of the oil phase were removed after 24 and 48 hours and the content of CLA glycerides formed was determined by gas chromatography. The result is expressed as the percentage triglyceride content, based on the sum of di- and triglyceride formed.

[0035] Results

TABLE 3Acceleration of the reaction of free CLA to CLA triglycerides,as measured from the percentage triglyceride content - basedon the sum of di- and triglyceride formed - as a functionof the sodium carbonate conc...

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Abstract

Processes for the enzyme-catalyzed production of triglycerides using polyunsaturated fatty acids, in which (a) the reaction of polyunsaturated fatty acids and/or C1-4 alkyl esters thereof with glycerol in vacuo in the presence of an immobilized enzyme to form their triglycerides is accelerated by addition of an additive from the group of weakly basic salts, complexing agents and ion exchangers and/or addition of a weakly basic salt and/or addition of an entraining agent in the form of a solvent or a gas and/or addition of glycerol-binding adsorbers and/or heat treatment of the partial glyceride intermediate product, (b) the immobilized enzymes are removed from the triglyceride by separation or filtration and (c) the remaining fatty acids and/or C1-4 alkyl esters thereof are removed from the triglyceride by distillation, refining or extraction.

Description

BACKGROUND OF THE INVENTION [0001] Esters of polyunsaturated fatty acids can be produced both by chemical and by enzymatic methods. Chemical syntheses have the disadvantage that very high temperatures generally have to be used and large quantities of basic catalysts are required so that secondary products and unwanted isomerizations occur to a fairly significant extent. One way of reducing the reaction temperature in the chemical synthesis of glycerol esters of polyunsaturated fatty acids was disclosed in European patent application EP 1 354 934 A1. By using a mixed catalyst of a salt of a weak acid and a strong base together with the soap of an organic C2-26 acid, the reaction temperature was reduced to below 175° C. and preferably to 100-140° C. However, enzyme-catalyzed reactions with lipases still generally take place under milder conditions and give high-purity end products. [0002] Thus, European patent EP 0 950 410 A1 and International patent WO 0 178 531 describe syntheses in...

Claims

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Application Information

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IPC IPC(8): C11C3/06C11C3/10C12P7/64
CPCC12P7/6472
Inventor SCHOERKEN, ULRICHBOTH, SABINEMEYER, CAROLINHORLACHER, PETER
Owner COGNIS IP MANAGEMENT GMBH
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