Ricinoleic Acid → Methyl 10-undecenoate

This example illustrates the synthesis of the C20 diacid starting from ricinoleic acid. During the first stage, methyl ricinoleate is subjected to a pyrolysis at a temperature of 550° C. to form methyl 10-undecenoate, which is converted to the acid form by hydrolysis. In the second homometathesis stage, use is made of the ruthenium complex (3) catalyst described in the publication by Stefan Randl et al., Synlett (2001), 10, 430, which is very stable and does not decompose when it is exposed to air or to water. The homometathesis reaction is carried out in CH2Cl2, at a 0.15M 10-undecenoic acid concentration, at a temperature of 30° C. and for 2 hours with a catalyst concentration of 0.5 mol %. The yields are determined by chromatographic analysis. The yield of diacid HOOC—(CH2)8—CH═CH—(CH2)8—COOH is 67 mol %. This product can be hydrogenated according to a conventional process with a yield of 100%.

1. customis subjected to a pyrolysis at a temperature of 550° C.

ORD record

ord-1a5ab12081fd47b0b43b6ed9b95ed027

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940923B2