Octanoic Acid → Diglycerin

HRID 847473

반응식

HRID 847473 반응식
CCCCCCCCCC(O)=O.CCCCCCCC(O)=O.[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH:48]([OH:51])[CH2:49][OH:50])=[O:45].[OH:52][CH2:53][CH:54]([CH2:56][OH:57])[OH:55]>>[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH:48]([OH:51])[CH2:49][OH:50])=[O:45].[C:44]([OH:46])(=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23].[OH:52][CH2:53][CH:54]([CH2:56][OH:57])[OH:55].[CH2:47]([OH:46])[CH:48]([OH:51])[CH2:49][O:52][CH2:53][CH:54]([OH:55])[CH2:56][OH:57]

참가 물질

7

반응물 4

HCID 379Octanoic AcidHCID 753GlycerolHCID 2969Decanoic AcidHCID 5362585Glyceryl Monobehenate2회

생성물 3

HCID 42953Diglycerin수율 0.3%HCID 5362585Glyceryl MonobehenateHCID 22477175Glyceryl Dibehenate

실험 절차

Typically, about 118 kg of a mixture of C10:0 and C8:0 fatty acids (55:45 weight ratio) was preheated to the esterification temperature. This fatty acid mixture was used to esterify about 16.8 kg of monobehenin at a 18:1 acid to monobehenin mole ratio at esterification temperatures in the range of 174°-210° C. for 1.5 to 3.5 hours. (The monobehenin was commercially produced by molecular distillation of behenic acid/glycerol reaction products and comprised 98.1% monoglyceride, 0.5% diglyceride, 0.1% free glycerol, and 0.3% diglycerol.) The monobehenin was added incrementally as a powder over a 10 minute period to the melted fatty acids. Vigorous agitation (571 m./min. tip speed) and a nitrogen gas sparging rate of 1.4-2.1 liter/min. per liter of reaction mixture was used to remove the water generated during the esterification. The light fatty acids were refluxed by the partial condenser operated at 110° C., while generated water was condensed by the total condenser at 40° C. The esterification progress was monitored by thin layer chromatography (TLC) using high performance silica plates and a 75% petroleum ether/25% diethyl ether/1% acetic acid development solvent, followed by charring with 5% phosphomolybdic acid in anhydrous methanol. The esterification were stopped after complete elimination of diglycerides (i.e. measured level typically less than 0.4%). Composite analyses of the six esterification indicated a 6.4% MMM, 89.9% MML/MLM and 3.7% MML/LML triglyceride composition (average) in the reaction mixture. (As determined by CNP (acid free basis), "MMM"≤C24 to C34, "MML/MLM"=C36 to C44, and "MLL/LML"C46 to C56.) The free fatty acid profiles for the reaction mixtures were determined to be 42.9% C8:0, 56.2% C10:0, 0.7% C12:0, and 0.2% C22:0 fatty acids (average), which suggests minimal long chain fatty acid hydrolysis occurred under these esterification conditions. (As determined by free fatty acid profiles, "long chain fatty acid"=combined C20:0C22:0 and C24:0.)

후처리

  1. customin the range of 174°-210° C.
  2. customfor 1.5 to 3.5 hours

출처 및 근거

ORD 기록
ord-ccee45cded3f4bf4973dbce7ce647a54
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142071

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