Adipic Acid → 1,4-Butanediol

HRID 2299606Notes

Reaction equation

HRID 2299606 reaction equation
[C:1](O)(=[O:7])[CH2:2][CH2:3][C:4](O)=[O:5].[C:9](O)(=[O:16])[CH2:10][CH2:11][CH2:12][C:13](O)=[O:14].[C:18](O)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24]>>[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][OH:5].[CH2:9]([OH:16])[CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[CH2:18]([OH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

6

Reactant 3

HCID 196Adipic AcidHCID 743Glutaric AcidHCID 1110Succinic Acid

Product 3

HCID 80641,4-ButanediolHCID 81051,5-PentanediolHCID 123741,6-Hexanediol

Procedure

The obtained reaction mixture was analyzed by HPLC and GC under the conditions mentioned above to determine the conversion of the starting material and the yield of the primary alcohol. The analysis showed that the conversions of succinic acid, glutaric acid and adipic acid were 87%, 87% and 90%, respectively, and the yields of 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol were 43%, 69% and 50%, respectively.

Workup

  1. customThe obtained reaction mixture

Sources & evidence

ORD record
ord-6537d36874f84101ace67bed032ccfaf
Source dataset
uspto-grants-2002_12
Patent number
US06495730B1

Reaction notes

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