Azelaic Acid → 9-Octadecenedioic acid

HRID 1836076

Reaction equation

HRID 1836076 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](O)=O.[C:14]([OH:33])(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=C\CCCCCCCC>>[C:14]([OH:33])(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:13])=[O:12]

Participants

3

Procedure

Another preferred embodiment of the invention is based on the preparation of azelaic acid by biooxidation of oleic acid to form 9-octadecenedioic acid followed by oxidation of the 9-octadecenedioic acid to azelaic acid. While any grade of oleic acid can be used as the substrate, a typical technical grade oleic acid consists of the following carboxylic acids: 0.42% C12; 2.7% C14; 0.86% C14:1, 6.3% C16; 4.6% C16:1, 0.93% C17; 2.8% C18; 71.8% C18:1; 8.3% C18:2; 0.58% C18:3. The oleic acid can also be a high grade oleic acid obtained from a fatty oil of a Helianthus annuus (sunflower seed oil) species described, for example, in U.S. Pat. No. 4,627,192, the entire contents of which are incorporated herein by reference. Such oils are very rich in oleic acid and contain at least 80% by weight of oleic acid.

Sources & evidence

ORD record
ord-2c4626632c8e4f77b24a2efa5f11c672
Source dataset
uspto-grants-2004_08
Patent number
US06777213B2

Linked notes

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