- Natural oil metathesis compositions and methods
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A metathesized natural oil composition comprising (i) a mixture olefins and/or esters, or (ii) a metathesized natural oil, is disclosed. The metathesized natural oil composition has a number average molecular weight in the range from about 100 g/mol to about 150,000 g/mol, a weight average molecular weight in the range from about 1,000 g/mol to about 100,000 g/mol, a z-average molecular weight in the range from about 5,000 g/mol to about 1,000,000 g/mol, and a polydispersity index of about 1 to about 20. The metathesized natural oil composition is metathesized at least once.
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Page/Page column 21; 22; 23; 24
(2018/03/07)
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- Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols
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Symmetrical disaturated triacylglycerols of the structure SUS, where S is stearic acid (18:0) and U is an unsaturated fatty acid, either oleic (O; 9cis-18:1), linoleic (L; 9cis, 12cis-18:2), or linolenic (Ln; 9cis, 12cis, 15cis-18:3), are important components providing functionality to interesterified fat blends and structurally modified oils. Nonsymmetrical triacylglycerols of the structure SSU can significantly change melting point and solid fat content profiles. To characterize the physical properties of pure and symmetrical and nonsymmetrical triacylglycerol mixtures, the same reaction sequence has been used to prepare multigram quantities of triacylglycerols SUS and SSU. Tristearin was converted to a mixture of mono-, di-, and triacylglycerols, and the 1,3- and 1,2-diacylglycerol fraction was isolated by silica column chromatography. The 1,3-diacylglycerols were removed by crystallization from acetone and esterified with the appropriate fatty acid to form the symmetrical triacylglycerols with >99% SUS structure. The more difficult to obtain 1,2-diacylglycerols were prepared by esterification of the enriched 1,2-diacylglycerol fraction (80-86% 1,2-diacylglycerols) remaining after removal of much of the 1,3-isomer by crystallization, but silver resin or silver nitrate impregnated silica gel chromatography was required to isolate the nonsymmetrical triacylglycerols. SSL and SSLn were prepared in purities of >98% by this procedure, but not SSO. Silver ion HPLC was found to be as accurate as, and more rapid than, lipolysis/gas chromatography for the determination of the isomeric purities of the synthesized triacylglycerols.
- Adlof, Richard O.,List, Gary R.
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p. 2096 - 2099
(2007/10/03)
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- Enzymatic interesterification of triolein and tristearin: Chemical structure and differential scanning calorimetric analysis of the products
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The structural composition and thermal properties of the products of enzymatic interesterification of triolein and tristearin were investigated. The biocatalyst for the reaction was an immobilized Candida antarctica lipase, SP435. Enzyme load of 10% (w/w reactants) produced 72% of desired total products. Oleoyl-distearoyl triglycerides (SSO, OSS) had higher melting points than dioleoyl-stearoyl triglycerides (OOS, SOO) because the sample contained larger amounts of stearic acid than oleic acid residues. SOS and OSO were hardly produced (0.2 to 1.2%), which indicates that SP435 acted as a nonspecific lipase when catalyzing the interesterification of triolein and tristearin. The maximal yield of OSS and SSO (46.9%) was achieved with a 1:2 mole ratio of triolein to tristearin. As the proportion of tristearin was increased, the production of SOO and OOS decreased, the melting profile of the interesterified triglycerides shifted toward higher melting forms, and the solid fat content increased, indicating formation of hard fats.
- Seriburi, Vimon,Akoh, Casimir C.
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p. 711 - 716
(2007/10/03)
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- Synthesis of Triglycerides from 1,3-Dibromopropan-2-ol
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1,3-Dibromopropan-2-ol (I) was converted into an acyl derivative (VI) by reaction with an appropriate acyl chloride in the presence of pyridine.The acyl derivative (VI) was subjected to nucleophilic substitution with 3 mol. equiv. tris(decyl)methylammonium carboxylate in refluxing hexane.This led to symmetrical diacid triglycerides in 90-94percent yield.Substitution with an equimolar amount of the carboxylate afforded, predominantly, the 1,2-bisacyloxy-3-bromopropane (VII) which could be easily isolated and further substituted to give unsymmetrical diacid- and triacid-triglycerides in ca. 96percent yield.Lipolysis showed the synthetic triglycerides to be ca. 99percent pure.
- Bhati, Asharam,Hamilton, Richard J.,Steven, David A.,Aneja, Rajender,Padley, Frederick B.
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p. 1553 - 1558
(2007/10/02)
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