Adipic Acid → HCID 86587302, compound

HRID 992661Notes

Reaction equation

[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH:19][CH2:20][CH:21]([CH2:23][OH:24])[OH:22].[C:25]([OH:34])(=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]>O>[C:25]([OH:34])(=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].[OH:19][CH2:20][CH:21]([CH2:23][OH:24])[OH:22].[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 190 °C

Procedure

A pre-gel composition having carboxyl-rich end groups was made in the following manner. To a 5-liter flask equipped with agitator, heating mantle, thermometer, and distillation setup, 726 g (2.84 equivalents) palmitic acid, 336 g (10.96 equivalents) glycerol, and 954 g (13.07 equivalents) adipic acid were added. The batch was heated at 150-200° C., whereupon water of reaction began to distill. The pressure was gradually reduced while maintaining the reaction temperature at 180-200° C. Heating was continued until water production had essentially stopped. Of the theoretical 197 g of water expected, a total of 181 g (92%) of water was collected. At 100-120° C., the batch remained a thick but stirrable liquid and did not gel. This pre-gel composition had carboxyl-rich end groups.

Workup

customTo a 5-liter flask equipped with agitator
temperatureheating mantle
additionwere added
distillationto distill
temperatureHeating
customa total of 181 g (92%) of water was collected
customAt 100-120° C.

Sources & evidence

ORD record: ord-a1bd46ddb36a41cd8ecc2c59f576ad0e
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469129B1

Reaction notes

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