Free radical addition of hydrogen sulfide and thiols to linseed oil and methyl oleate View Full Text


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Article Info

DATE

1968-06

AUTHORS

A. W. Schwab, L. E. Gast, J. C. Cowan

ABSTRACT

Free radical additions of hydrogen sulfide, ethanedithiol, and 1,6-hexanedithiol have been made to methyl oleate and linseed oil with ultraviolet radiation. Reactions were carried out in dichloromethane at −70C and in benzene at 25C. With the dithiols, a new dibasic ester has been prepared from methyl oleate in which bridging is accomplished through a dithiol moiety. Hydrogen sulfide has been added to linseed oil in suitable solvents at both −70C and 25C. It appears that zero-order kinetics control the additions at both temperatures. Infrared data show a linear relationship between mercapto absorption and the amount of sulfur incorporated. Nuclear magnetic resonance (NMR) spectra demonstrate a decrease in olefinic protons with an increase in sulfur content. Fair agreement on the extent of reaction exists between data from NMR, sulfur content, and infrared analyses. Hydrogen sulfide-treated linseed oil films air-dry slowly at room temperature; at 250C for 1 hr under a CO2 atmosphere these oils cure to brown films with Sward Rocker values of 24 to 32 and pencil hardness values of five to greater than six. Pencil hardness and alkali resistance increased with sulfur content. The film from the 4.2% sulfur sample resisted alkali at room temperature for 24 hr. More... »

PAGES

461-464

References to SciGraph publications

  • 1958-05. The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1958-09. Epoxidized jojoba oil as a stabilizer for vinyl chloride containing plastics in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1966-01. N-2-mercaptoethyl amides of fatty acids—A new class of derivatives in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1959-07. Device to establish drying conditions for protective coatings at elevated temperatures in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
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    http://dx.doi.org/10.1007/bf02655509

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