Adipic Acid → Cyclohexanol

HRID 892222Notes

Reaction equation

HRID 892222 reaction equation
[C:1]([OH:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][C:6](O)=O.C(O)(=O)CCCC(O)=O>C1CCCCC1>[C:1]1(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:1]1([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 196Adipic AcidHCID 743Glutaric Acid

Product 2

HCID 7966CyclohexanolHCID 7967Cyclohexanone

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Conventionally, 1,6-hexanediol is produced from an organic acid mixture containing adipic acid, hydroxycapronic acid and glutaric acid, wherein the organic acid mixture is by-produced during the production of cyclohexanone and/or cyclohexanol by oxidation of cyclohexane with air. For producing 1,6-hexanediol, the organic acid mixture is subjected to esterification and then to hydrogenation in the presence of a copper catalyst to thereby obtain 1,6-hexanediol, and the obtained 1,6-hexanediol is purified by distillation. 1,6-Hexanediol which is conventionally produced in the above-mentioned manner contains 1,4-cyclohexanediol, and such 1,6-hexanediol is not suitable as a raw material for producing the polycarbonate diol of the present invention. The boiling point of 1,4-cyclohexanediol and the boiling point of 1,6-hexanediol are very close to each other and, therefore, it is difficult to decrease the amount of 1,4-cyclohexanediol in 1,6-hexanediol to the above-mentioned preferred level (i.e., 0.5% by weight or less) by distillation.

Sources & evidence

ORD record
ord-929328abada14b4f9780a53f3ac46208
Source dataset
uspto-grants-2006_02
Patent number
US07005495B2

Reaction notes

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