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US 2012/0052539 A1 Favre Et Al US 20120052539A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0052539 A1 FaVre et al. (43) Pub. Date: Mar. 1, 2012 (54) PROCESS FOR MAKING ATRIGLYCERIDE (30) Foreign Application Priority Data COMPOSITION May 11, 2009 (EP) .................................. O9251287.0 (76) Inventors: Thomas Louis Francois Favre, AZ Wormerveer (NL); Henry Kos, AZ Publication Classification Wormerveer (NL); Krishnadath (51) Int. Cl. Bhaggan, AZ Wormerveer (NL); CI2P 7/64 (2006.01) Sylvain Jacques Fages, Orbe (CH) (52) U.S. Cl. ........................................................ 435/134 (21) Appl. No.: 13/319,403 (57) ABSTRACT (22) PCT Filed: May 10, 2010 A process for preparing a triglyceride composition compris ing from 50 to 80% by weight StC)Stand from 5 to 20% by (86). PCT No.: PCT/EP201 O/OO2865 weight StCO comprises reacting triolein with stearic acid in the presence of a 1.3-specific lipase from Rhizopus Oryzae to S371 (c)(1), form interesterified glycerides and fractionating the interest (2), (4) Date: Nov. 8, 2011 erified triglycerides. US 2012/0052539 A1 Mar. 1, 2012 PROCESS FOR MAKING ATRIGLYCERIDE O010 Seriburietal, JAOCS, vol 75, no 4, 1998, 511-516 COMPOSITION discloses the transesterification of triolein and Stearic acid using lipases from Rhizomucor miehei or Candida antarctica. (0011 U.S. Pat. No. 6,090,598 discloses an enzymatic pro 0001. This invention relates to a process for making a cess for interesterification of fats and oils using distillation. triglyceride composition and to the composition obtainable There is no disclosure of an example for producing StGStand by the process. the only mention of the production of this triglyceride is 0002 Triglycerides comprise three fatty acid moieties starting from a stearic acid ester. bonded to a glycerol backbone. When a triglyceride contains 0012. There remains a need for processes for the forma two or more different fatty acid moieties, its properties, tion of StOSttriglycerides, in particular compositions that are including its physical and chemical properties as well as similar to shea Stearin in terms of the triglycerides that they physiological characteristics, may depend on the position on contain. There is also a need for processes that do not involve the glycerol backbone at which each of the fatty acids is the formation of undesirable side products that need to be attached in the molecule. Therefore, it can be desirable to removed from the product. control processes for producing triglycerides such that the 0013. Accordingly, the present invention provides a pro different fatty acid residues are selectively attached at differ cess for preparing a triglyceride composition comprising ent positions on the glycerol backbone. from 50 to 80% by weight StC)Stand from 5 to 20% by weight 0003) 1,3-Distearoyl 2-oleoyl glyceride (also known as StOO, which process comprises reacting triolein with stearic StOSt) is a valuable commercial product. For example, it may acid in the presence of a 1.3-specific lipase from Rhizopus be used, either alone or together with other glycerides such as Oryzae to form interesterified glycerides and fractionating the 1,3-dipalmitoyl 2-oleoylglyceride, as a cocoa butter equiva interesterified triglycerides. lent or substitute (CBE). 0014. Also provided by the invention is a triglyceride 0004 Shea butter is used commercially as a source of composition comprising from 50 to 80% by weight StC)Stand StOSt. Shea butter is obtained from the shea butter tree Buty up to 20% by weight StCO obtainable by the process of the rospermum parkii. Shea Stearin, the higher melting fraction invention. which is obtained by fractionation of shea butter, is enriched 0015. It has surprisingly been found that it is possible to in StCSt but contains other triglycerides such as StCO and produce a triglyceride composition that is similar to shea StLSt (where L represents linoleic acid). Thus, Shea stearin is stearin. This effect is achieved by using the 1.3-specific lipase used to produce cocoa butter equivalents (CBEs). The avail from Rhizopus Oryzae for the reaction of triolein with stearic ability of Shea stearin is dependent on the supply of Shea acid and Subsequently fractionating the product. nutS. 0016. The reaction between triolein and stearic acid is 0005 EP-A-0882797 relates to the preparation of ABA typically carried out at a temperature of from 45 to 85°C. symmetrical triglycerides from 2-monoglycerides using a Preferably, the step of reacting the triolein with stearic acid is 1.3-selective lipase. carried out at a temperature of from 65 to 80° C., more 0006 U.S. Pat. No. 5.288,619 describes an enzymatic preferably from 65 to 75°C., even more preferably from 68 to transesterification method for preparing a margarine oil hav 73°C. It has unexpectedly been found that surprisingly good ing both low trans-acid and low intermediate chain fatty acid results are obtained at these relatively higher reaction tem content. The method includes the steps of providing a trans peratures. It was Surprising that the lipase retains sufficient esterification reaction mixture containing a stearic acid activity at these high temperatures to catalyse the reaction Source material and an edible liquid vegetable oil, transesteri effectively. The ability to carry out the reaction at these high fying the Stearic acid source material and the vegetable oil temperatures permits the use of Stearic acid as a starting using a 1.3-positionally specific lipase, and then finally material for the process rather than its esters which have lower hydrogenating the fatty acid mixture to provide a recycle melting points. This, in turn, means that the side products Stearic acid source material for a recyclic reaction with the produced from the Stearoyl esters during the reaction can be vegetable oil. avoided. 0007 U.S. Pat. No. 4,268,527 discloses a method for pro 0017. The reaction of the triolein with the stearic acid is ducing a cocoa butter substitute (CBE) by transesterification preferably carried out at atmospheric pressure i.e., in a non of fats and oils containing glycerides rich in the oleyl moiety pressurised system. The reaction may be carried out in a at the 2-position with an alcohol ester of stearic acid and/or packed bed reactor. The reaction is preferably carried out as a palmitic acid in the presence of a lipase having reaction continuous process. specificity to the 1.3-position of triglycerides and not more 0018. The reaction of triolein with stearic acid is prefer than 0.18% by weight of water based on the total weight of the ably carried out in the complete or substantial absence of reaction mixture. A cocoa butter substitute, rich in 1,3-dis added organic solvents, such as alcohols and/or ketones hav tearyl-2-oleyl compound and 1-palmityl-2-oleyl-3-Stearyl ing from 1 to 6 carbon atoms. Typically, alcohols and/or compound is said to be obtained. ketones having from 1 to 6 carbon atoms will be absent from 0008 EP-A-0245076 describes the preparation of edible the reaction mixture or, if present, they will be present in an fats by the reaction of high oleic sunflower oil with stearic amount of less than 1% by weight, more preferably less than acid in the presence of a lipase. The resulting composition, 0.5% by weight, such as less than 0.1% by weight, based on after wet fractionation, is significantly different from shea the weight of the reaction mixture. stearin in its StOSt and StOO contents. 0019. The lipase that is used in the invention is from Rhizo 0009 Nakaya et al. Biotechnology Techniques, Vol 12, no pus Oryzae. The lipase may be produced in Rhizopus Oryzae 12, 1998, 881-884 describes the transesterification reaction itself or produced recombinantly using a different host cell. between triolein and Stearic acid using an immobilised lipase The lipase may be modified, for example by the substitution from Mucor miehei in supercritical CO. or deletion of up to 10% of the amino acid residues in the US 2012/0052539 A1 Mar. 1, 2012 enzyme (i.e., the lipase may have at least 90% identity with 0028. The weight ratio of stearic acid to the starting mate the wild type enzyme) without loss of lipase activity, but it is rial comprising triolein is preferably in the range of from 1:1 preferably the wild type enzyme. The lipase from Rhizopus to 1:2. Oryzae is commercially available from Amano as Lipase D. 0029. The reaction of the triolein with the stearic acid is 0020. The lipase is preferably immobilised on a support. typically carried out for a time of from 20 to 200 hours, more The support is preferably a polymer, more preferably a preferably from 30 to 150 hours. microporous polymer, such as a microporous polypropylene 0030. After the triolein has been reacted with the stearic polymer (e.g., a homopolymer), for example as sold under the acid, the product is fractionated. Fractionation can be dry or trade mark Accurel. The preferred loading of the lipase onto wet but preferably the product is wet fractionated i.e., frac the support is in the range of from 0.1 to 25% by weight of tionated in the presence of a solvent. More preferably, the wet enzyme based on the weight of the Support, more preferably fractionation is carried out using acetone. from 0.3 to 10% by weight, such as from 0.5 to 5% by weight. 0031. The fractionation process can involve one fraction Theoretically (i.e., assuming the immobilisation has no effect ation step or two or more fractionation steps at different on the activity of the enzyme), the activity of the immobilised temperatures. enzyme (i.e., enzyme plus support) is preferably from 10,000 0032 Preferably, the reaction product is fractionated to 10,000,000 U/g, more preferably from 100,000 to 1,000, using acetone in a two-stage fractionation process.
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