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Synthesis of novel urethanes from a castor oil derived C22-acyloin

(2011) ARKIVOC. p.261-271
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Biotechnology for a sustainable economy (Bio-Economy)
Abstract
The synthesis of new bio-based chemical building blocks, resulting from the condensation of a renewable C-22 acyloin derived from non-edible castor oil, with mono- and bifunctional isocyanates is reported. The condensation with aliphatic mono-isocyanates was relatively straightforward, however phenyl isocyanates only resulted in low yields together with the formation of a cyclic hemi-aminal during purification. The condensation with diisocyanates was successful for the aliphatic hexamethylene diisocyanate. As for the aromatic 2,4-toluene diisocyanate, a low yield of the desired product was obtained, since a similar ring closing reaction took place. The urethanes were synthesized in order to evaluate their plasticizing and viscosity-modifying properties.
Keywords
isocyanates, nucleophilic addition, undecylenic acid, urethanes, castor oil, Acyloin, RENEWABLE BUILDING-BLOCK, UNDECYLENIC ACID, ISOCYANATES

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Citation

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Chicago
Van der Steen, Marijke, Maris Vilums, and Christian Stevens. 2011. “Synthesis of Novel Urethanes from a Castor Oil Derived C22-acyloin.” Arkivoc (9): 261–271.
APA
Van der Steen, Marijke, Vilums, M., & Stevens, C. (2011). Synthesis of novel urethanes from a castor oil derived C22-acyloin. ARKIVOC, (9), 261–271.
Vancouver
1.
Van der Steen M, Vilums M, Stevens C. Synthesis of novel urethanes from a castor oil derived C22-acyloin. ARKIVOC. 2011;(9):261–71.
MLA
Van der Steen, Marijke, Maris Vilums, and Christian Stevens. “Synthesis of Novel Urethanes from a Castor Oil Derived C22-acyloin.” ARKIVOC 9 (2011): 261–271. Print.
@article{1889476,
  abstract     = {The synthesis of new bio-based chemical building blocks, resulting from the condensation of a renewable C-22 acyloin derived from non-edible castor oil, with mono- and bifunctional isocyanates is reported. The condensation with aliphatic mono-isocyanates was relatively straightforward, however phenyl isocyanates only resulted in low yields together with the formation of a cyclic hemi-aminal during purification. The condensation with diisocyanates was successful for the aliphatic hexamethylene diisocyanate. As for the aromatic 2,4-toluene diisocyanate, a low yield of the desired product was obtained, since a similar ring closing reaction took place. The urethanes were synthesized in order to evaluate their plasticizing and viscosity-modifying properties.},
  author       = {Van der Steen, Marijke and Vilums, Maris and Stevens, Christian},
  issn         = {1551-7012},
  journal      = {ARKIVOC},
  keyword      = {isocyanates,nucleophilic addition,undecylenic acid,urethanes,castor oil,Acyloin,RENEWABLE BUILDING-BLOCK,UNDECYLENIC ACID,ISOCYANATES},
  language     = {eng},
  number       = {9},
  pages        = {261--271},
  title        = {Synthesis of novel urethanes from a castor oil derived C22-acyloin},
  url          = {http://dx.doi.org/10.3998/ark.5550190.0012.919},
  year         = {2011},
}

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