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Reactions of unsaturated fatty alcohols. VI. Guerbet reaction of soybean and linseed alcohols
Author(s) -
Gast L. E.,
Bitner E. D.,
Cowan J. C.,
Teeter H. M.
Publication year - 1958
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02638782
Subject(s) - linseed oil , chemistry , organic chemistry , alcohol , potassium hydroxide , fatty alcohol , solvent , maleic anhydride , soybean oil , food science , polymer , copolymer
Summary Both soybean and linseed alcohols were heated with potassium hydroxide and boric anhydride at 300°C. for 3 to 4 hrs. Products obtained under these conditions contained no unreacted starting alcohol, and each one appeared to be a mixture of condensed alcohols with average molecular weights of 720–860. Infrared spectroscopic studies and chemical analyses indicate that little or no ethers, esters, or carbonyl compounds were present in the final product from either alcohol. Such reactions as thermal cross‐linking of the unsaturated side chains probably account for higher molecular weight products than those obtained in the Guerbet reaction of stearyl alcohol. Condensed alcohols from soybean and linseed alcohol were esterified with acrylic, sorbic, maleic, and soybean fatty acids to yield products with low acid numbers. Preliminary experiments demonstrated that these alcohols and their esters showed promise as materials for protective coatings. Films from these alcohols and esters were cast from toluene containing a cobalt naphthenate drier and were baked at 150°C. for 1 hr. or at 200°C. for 20 min. All of the baked films were hard to moderately hard and showed good resistance to aqueous alkali and organic solvents. In general, films from soybean condensed alcohol and its esters were harder than those from linseed condensed alcohols, but the linseed films were superior in alkali and solvent resistance. A soybean fatty acid ester of soybean condensed alcohol air‐dried to a soft film in 3 days.