Glyceryl 1,3-Dilaurate → Vinyl laurate

HRID 718561ノート

反応式

HRID 718561 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH:16](O)COC(CCCCCCCCCCC)=O)=[O:13]>OCC(CO)O>[CH:15]([O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH2:16]

参加物

3

反応物 1

HCID 101758Glyceryl 1,3-Dilaurate

生成物 1

HCID 75069Vinyl laurate

試薬・触媒・溶媒 1

HCID 753Glycerol溶媒

実験手順

1,3 DLa was easily purified and recovered by crystallization in dry methanol at room temperature (RT) or in hexane at −20° C. (purity >98%). When lauric acid (La) was used as an acyl-donor, solvent was added to dissolve the FFA. Though the method as described in J. Am. Oil Chem. Soc., 1992, 69:955-960, allowed faster reaction rate with high yield of 1,3-DLa (65%), the highest yield (78%) of 1,3-DLa obtained from esterification between glycerol and lauric acid vinyl ester (LaVE) at 0° C. in a solvent-free condition catalyzed by CAL-B after 24 h, as illustrated in FIG. 14. FIG. 14 summarizes data of various synthesis of 1,3-dilaurin. Method1=esterification of glycerol and lauric acid in n-hexane at 0° C. catalyzed by CAL-B; Method2=esterification of glycerol and lauric acid vinyl ester in a solvent-free condition at 0° C. catalyzed by CAL-B; Method3 (Schneider's method)=esterification of glycerol (immobilized on silica gel) and lauric acid vinyl ester in MTBE at room temperature catalyzed by Lipozyme RM IM™ (Eurzyme, Dublin, Ireland). (DG=1,3-dilaurin, MG=1-monolaurin). LaVE, as acyl donor, allowed higher yield and faster reaction with less amount of MG than La.

後処理

  1. custom1,3 DLa was easily purified
  2. customrecovered by crystallization in dry methanol at room temperature (RT)
  3. customat −20° C.
  4. additionwas added
  5. dissolutionto dissolve the FFA
  6. customreaction rate with high yield of 1,3-DLa (65%)

出典と根拠

ORDレコード
ord-4fcb0e8926a44ee4aa03c4397866b031
出典データセット
uspto-grants-2015_11
特許番号
US09193962B2

反応ノート

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