Adipic Acid → 1,4-Butanediol

HRID 2299609Notes

Reaction equation

HRID 2299609 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 91%, 92% and 95%, respectively, and the yields of 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol were 57%, 76% and 58%, respectively.

Workup

  1. customThe obtained reaction mixture

Sources & evidence

ORD record
ord-6ffc93d2eb93475ca44fe3189352329e
Source dataset
uspto-grants-2002_12
Patent number
US06495730B1

Reaction notes

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