HRID1645780

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID196

Adipic Acid

C6H10O4

HCID6101

4-Methylbenzenesulfonic acid

C7H8O3S

HCID227803

未命名化合物

$结构：CCCCCCCC/C=C\CCCCCCCCO$

HCID5284499

cis-Oleyl alcohol

C18H36O

PRODUCTS

生成物

$结构：CCCCCCCC/C=C\CCCCCCCCOC(=O)CC(C=CCCCCCCCCCCCC)C(=O)OCCCCCCCC/C=C\CCCCCCCC$

HCID86746458

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

Seventeen millimoles of tetradecenylsuccinic anhydride (5.0 gm), 34 millimoles of oleyl alcohol (9.1 gm), 50 mg of adipic acid and 10 ml of toluene were combined in a boiling flask (with attached Dean-Stark trap) and refluxed for about 6 hours in the presence of the catalyst p-toluenesulfonic acid. Excess toluene was removed at ambient pressure. The residue was applied to a silica gel column, and eluted with petroleum ether. Elution with petroleum ether gave dioleyl tetradecenylsuccinate. Oleyl alcohol and other impurities were retained on the column. The dioleyl tetradecenylsuccinate has a low melting point and can be used for the commercial production of calorie-reduced fried snack foods.

WORKUP

后处理

customExcess toluene was removed at ambient pressure
washeluted with petroleum ether
washElution with petroleum ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c6e969a2a18d4b858c7481d305f13df8
来源数据集: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05176933
来源说明: uspto-grants-1993_01

反应 SMILES

[CH:1]([CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=[O:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:22]([OH:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[C:41](O)(=O)[CH2:42][CH2:43][CH2:44][CH2:45][C:46](O)=O.[C:51]1([CH3:61])[CH:56]=[CH:55][C:54](S(O)(=O)=O)=[CH:53][CH:52]=1>C1(C)C=CC=CC=1>[CH:1]([CH:15]([CH2:20][C:19]([O:18][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:16][CH2:15]/[CH:1]=[CH:2]\[CH2:3][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:51][CH3:61])=[O:21])[C:16]([O:40][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]