Alkaline cleavage of hydroxy unsaturated fatty acids. I. Ricinoleic acid and lesquerolic acid

Abstract

The effects of temperature and media on the fusion of ricinoleic and lesquerolic acid derivatives with concentrated aqueous alkali were examined. Improved yields of३‐hydroxy acids were obtained by use of excess 2‐octanol. The effect of excess 2‐octanol is discussed in relation to a recently proposed reaction mechanism.

Castor oil as a renewable resource for the chemical industry

“…It was disclosed that the major products are 10-hydroxydecanoic acid 8 and 2-octanone 7 at lower reaction temperatures (180-200 7C) and long reaction times (,13 h) with a caustic (NaOH or KOH)/methyl ricinoleate or castor oil ratio of 1 : 1 [61,77,94]. The 10-hydroxydecanoic acid is formed in good yield if the reaction is performed in the presence of a high-boiling unhindered primary or secondary alcohol [96,97]. For instance, iso-octanol (mixed isomers) is a suitable and potentially economical medium for producing high yields of 10-hydroxydecanoic acid.…”

“…It was for instance claimed that, as the reaction continues, the aldehydo acid can be converted irreversibly to sebacic acid. Moreover, the aldehydo acid can accept hydrogen from ricinloeic acid to be converted to a b,g-keto acid, which recycles into the system and gives rise to the 10-hydroxydecanoic acid 7 [96,97]. Furthermore, it is reported that using two equivalents of NaOH at 190-200 7C in ethanol as solvent yields up to 69% of pure 10-hydroxydecanoic acid [98].…”

Chemical transformations of renewable lubricant feedstocks

“…Although it is possible that the end product oils are performing well in the intended applications for some of these reported transformations, the added processing cost is likely to be a hurdle limiting broad commercial adoption. [81,82] © Woodhead Publishing Limited, 2013…”

“…High-quality bio-based polyols obtained by hydroformylation or ozonolysis of vegetable oils such as SBO fi nd many polyurethane applications [281]. Short-chain linear α,ω-dicarboxylic acids such as suberic acid (C 8 ), azelaic acid (C 9 ) or sebacic acid (C 10 ) can be derived from oils and fats by chemical oxidation (alkali fi ssion) of unsaturated fatty acids, which constitute particularly important building blocks for the synthesis of lubricants [81,82].…”

Castor Oil

“…The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1-or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250-275 C produces capryl alcohol[123-96-6], C 8 H 18 O 4 , and sebacic acid [111-20-6], C 10 H 18 O 4 ,(38)(39)(40). Sebacic acid is used in the manufacture of nylon-6,10.5.4.…”