Increased functionality of methyl oleate using alkene metathesis

References

• Ahmad, F. B. H. , S. Hamdan , M. A. Yarmo , and A. Alimunir . 1995. “Co-metathesis Reaction of Crude Palm Oil and Ethene.” Journal of the American Oil Chemists' Society 72 (6): 757–758.
   Web of Science ®Google Scholar
• Banks, R. L. , and G. C. Bailey . 1964. “Olefin Disproportionation.” Industrial and Engineering Chemistry Product Research 3 (3): 170–173.
   Web of Science ®Google Scholar
• Banks, R. L. , D. S. Banasiak , P. S. Hudson , and J. R. Norell . 1982. “Specialty Chemicals via Olefin Metathesis.” Journal of Molecular Catalysis 15: 21–33.
   Google Scholar
• Behr, A. , and J. P. Gomes . 2011. “The Cross Metathesis of Methyl Oleate with Cis-2-Butene-1,4-Diyl Diacetate and the Influence of Protecting Groups.” Beilstein Journal of Organic Chemistry 7: 1–8.
   PubMed Web of Science ®Google Scholar
• Biermann, U. , U. Bornscheuer , M. A. R. Meier , J. O. Metzger , and H. J. Schafer . 2011. “Oils and Fats as Renewable Raw Materials in Chemistry.” Angewandte Chemie International Edition in English 50 (17): 3854–3871.
   PubMed Web of Science ®Google Scholar
• Biswas, A. , B. K. Sharma , K. M. Doll , S. Z. Erhan , J. L. Willett , and H. N. Cheng . 2009. “Synthesis of an Amine Oleate Derivative Using an Ionic Liquid Catalyst.” Journal of Agricultural and Food Chemistry 57 (18): 8136–8141.
   PubMed Web of Science ®Google Scholar
• Bunker, S. P. , and R. P. Wool . 2002. “Synthesis and Characterization of Monomers and Polymers for Adhesives from Methyl Oleate.” Journal of Polymer Science A 40: 451–458.
   Web of Science ®Google Scholar
• Chatterjee, A. K. , T.-L. Choi , D. P. Sanders , and R. H. Grubbs . 2003. “A General Model for Selectivity in Olefin Cross Metathesis.” Journal of the American Chemical Society 125 (37): 11360–11370.
   PubMed Web of Science ®Google Scholar
• Despagnet-Ayoub, E. , and R. H. Grubbs . 2005. “A Ruthenium Olefin Metathesis Catalyst with a Four-Membered N-Heterocyclic Carbene Ligand.” Organometallics 24 (3): 338–340.
   Web of Science ®Google Scholar
• Dias, E. L. , S. T. Nguyen , and H. Grubbs . 1997. “Well-Defined Ruthenium Olefin Metathesis Catalysts: Mechanism and Activity.” Journal of the American Chemical Society 119 (17): 3887–3897.
   Web of Science ®Google Scholar
• Doll, K. M. , and S. Z. Erhan . 2005a. “The Improved Synthesis of Carbonated Soybean Oil Using Supercritical Carbon Dioxide at a Reduced Reaction Time.” Green Chemistry 7 (12): 849–854.
   Web of Science ®Google Scholar
• Doll, K. M. , and S. Z. Erhan . 2005b. “Synthesis of Carbonated Fatty Methyl Esters Using Supercritical Carbon Dioxide.” Journal of Agricultural and Food Chemistry 53 (24): 9608–9614.
   PubMed Web of Science ®Google Scholar
• Doll, K. M. , and S. Z. Erhan . 2008. “Synthesis of Cyclic Acetals (Ketals) from Oleochemicals Using a Solvent Free Method.” Green Chemistry 10 (6): 712–717.
   Web of Science ®Google Scholar
• Doll, K. M. , B. K. Sharma , and S. Z. Erhan . 2008. “Friction Reducing Properties and Stability of Epoxidized Oleochemicals.” CLEAN – Soil, Air, Water 36 (8): 700–705.
   Web of Science ®Google Scholar
• Erhan, S. Z. , M. O. Bagby , and T. C. Nelsen . 1997. “Drying Properties of Metathesized Soybean Oil.” Journal of the American Oil Chemists' Society 74 (6): 703–706.
   Web of Science ®Google Scholar
• Fürstner, A. , L. Ackermann , K. Beck , H. Hori , D. Koch , K. Langemann , M. Liebl , C. Six , and W. Leitner . 2001. “Olefin Metathesis in Supercritical Carbon Dioxide.” Journal of the American Chemical Society 123 (37): 9000–9006.
   PubMed Web of Science ®Google Scholar
• Holser, R. A. , K. M. Doll , and S. Z. Erhan . 2006. “Metathesis of Methyl Soyate with Ruthenium Catalysts.” Fuel 85 (3): 393–395.
   Web of Science ®Google Scholar
• Hong, S. H. , M. W. Day , and R. H. Grubbs . 2004. “Decomposition of a Key Intermediate in Ruthenium-Catalyzed Olefin Metathesis Reactions.” Journal of the American Chemical Society 126 (24): 7414–7415.
   PubMed Web of Science ®Google Scholar
• Hong, S. H. , D. P. Sanders , R. H. Grubbs , and C. W. Lee . 2005. “Prevention of Undesirable Isomerization During Olefin Metathesis.” Journal of the American Chemical Society 127 (49): 17160–17161.
   PubMed Web of Science ®Google Scholar
• Li, S. , L. Hojabri , and S. S. Narine . 2012. “Controlling Product Composition of Metathesized Triolein by Reaction Concentrations.” Journal of the American Oil Chemists' Society 89 (11): 2077–2089.
   Web of Science ®Google Scholar
• Millis, J. R., M. J. Tupy, T. W. Abraham, and M. L. de Souza . 2011. Method for making industrial chemicals. US Patent 7960599, filed June 14.
   Google Scholar
• Mol, J. C. 2004. “Industrial Applications of Olefin Metathesis.” Journal of Molecular Catalysis A 213 (1): 39–45.
   Web of Science ®Google Scholar
• Montenegro, R. E. , and M. A. R. Meier . 2012. “Lowering the Boiling Point Curve of Biodiesel by Cross-Metathesis.” European Journal of Lipid Science and Technology 114 (1): 55–62.
   Web of Science ®Google Scholar
• Ngo, H. L. , and T. A. Foglia . 2007. “Synthesis of Long Chain Unsaturated-Alpha-Omega-Dicarboxylic Acids from Renewable Materials via Olefin Metathesis.” Journal of the American Oil Chemists' Society 84 (8): 777–784.
   Web of Science ®Google Scholar
• Nicolaides, C. P. , J. H. Opperman , M. S. Scurrell , and W. W. Focke . 1990. “Metathesis of Fatty Esters Derived from South African Sunflower Oil.” Journal of the American Oil Chemists' Society 67 (6): 362–363.
   Web of Science ®Google Scholar
• Nicolaou, K. C. , P. G. Bulger , and D. Sarlah . 2005. “Metathesis Reactions in Total Synthesis.” Angewandte Chemie International Edition in English 44 (29): 4490–4527.
   PubMed Web of Science ®Google Scholar
• Refvik, M. D. , and R. C. Larock . 1999. “The Chemistry of Metathesized Soybean Oil.” Journal of the American Oil Chemists' Society 76 (1): 99–102.
   Web of Science ®Google Scholar
• Refvik, M. D. , R. C. Larock , and Q. Tian . 1999. “Ruthenium-Catalyzed Metathesis of Vegetable Oils.” Journal of the American Oil Chemists' Society 76 (1): 93–98.
   Web of Science ®Google Scholar
• Rölle, T. , and R. H. Grubbs . 2002. “Ring Closing Metathesis in Protic Media by Means of a Neutral and Polar Ruthenium Benzylidene Complex.” Chemical Communications 8 (10): 1070–1071.
   Web of Science ®Google Scholar
• Rybak, A. , and M. A. R. Meier . 2007. “Cross-Metathesis of Fatty Acid Derivatives with Methyl Acrylate: Renewable Raw Materials for the Chemical Industry.” Green Chemistry 9 (12): 1356–1361.
   Web of Science ®Google Scholar
• Sacristan, M. , J. C. Ronda , M. Galia , and V. Cadiz . 2011. “Phosphorus-Containing Soybean-Oil Copolymers: Cross-Metathesis of Fatty Acid Derivatives as an Alternative to Phosphorus-Containing Reactive Flame Retardants.” Journal of Applied Polymer Science 122 (3): 1649–1658.
   Web of Science ®Google Scholar
• Sandford, M. S. , J. A. Love , and R. H. Grubbs . 2001. “Mechanism and Activity of Ruthenium Olefin Metathesis Catalysts.” Journal of the American Chemical Society 123 (27): 6543–6554.
   PubMed Web of Science ®Google Scholar
• Schwab, P. , M. B. France , J. W. Ziller , and R. H. Grubbs . 1995. “A Series of Well-Defined Metathesis Catalysts – Synthesis of [RuCl2( = Ch′)(Pr3)2] and Its Reactions.” Angewandte Chemie International Edition in English 34 (18): 2039–2041.
   Web of Science ®Google Scholar
• Tullo, A. 2008. “Cargill, Materia Launch New Firm.” Chemical & Engineering News 86 (13): 6.
   Web of Science ®Google Scholar
• van Dam, P. B. , M. C. Mittelmeijer , and C. Boelhouwer . 1972. “Metathesis of Unsaturated Fatty Acid Esters by a Homogeneous Tungsten Hexachloride–Tetramethyltin Catalyst.” Chemical Communications 1972: 1221–1222.
   Web of Science ®Google Scholar
• van Dam, P. B. , M. C. Mittelmeijer , and C. Boelhouwer . 1974. “Homogeneous Catalytic Metathesis of Unsaturated Fatty Esters; New Synthetic Method for Preparation of Unsaturated Mono- and Dicarboxylic Acids.” Journal of the American Oil Chemists' Society 51: 389–392.
   Web of Science ®Google Scholar
• Verkuijlen, E. , F. Kapteijn , J. C. Mol , and C. Boelhouwer . 1977. “Heterogeneous Metathesis of Unsaturated Fatty Acid Esters.” Chemical Communications 1977: 198–199.
   Web of Science ®Google Scholar
• Warwel, S. , F. Bruse , C. Demes , and M. Kunz . 2004. “Polymers and Polymer Building Blocks from Meadowfoam Oil.” Industrial Crops and Products 20 (3): 301–309.
   Web of Science ®Google Scholar
• Wu, M.-S., K. S. Colle, R. Y. Saleh, A. D. Goodwin, and J. E. R. Stanat . 2010. Production of Synthetic Hydrocarbon Fluids, Plasticizers and Synthetic Lubricant Base Stocks from Renewable Feedstocks. US Patent 2010-0160506 A1, filed June 24.
   Google Scholar
• Wu, Z. , S. T. Nguyen , R. H. Grubbs , and J. W. Ziller . 1995. “Reactions of Ruthenium Carbenes of the Type (PPh3)2(X)2Ru = Ch–Ch = CPh 2 (X = Cl and CF3COO) with Strained Acyclic Olefins and Functionalized Olefins.” Journal of the American Chemical Society 117 (20): 5503–5511.
   Web of Science ®Google Scholar
• Yao, L. , E. G. Hammond , T. Wang , S. Bhuyan , and S. Sundararajan . 2010. “Synthesis and Physical Properties of Potential Biolubricants Based on Ricinoleic Acid.” Journal of the American Oil Chemists' Society 87 (8): 937–945.
   Web of Science ®Google Scholar
• Yarmo, M. A. , A. Alimuniar , R. Abd Ghani , A. R. Sulaiman , M. Ghani , H. Omar , and A. Malek . 1992. “Transesterification Products from the Metathesis Reaction of Palm Oil.” Journal of Molecular Catalysis 76 (1–3): 373–379.
   Google Scholar
• Zerkowski, J. , and D. Solaiman . 2012. “Omega-Functionalized Fatty Acids, Alcohols, and Ethers Via Olefin Metathesis.” Journal of the American Oil Chemists' Society 89 (7): 1325–1332.
   Web of Science ®Google Scholar
• Zullo, J. L., J. C. Anderson, H. Kaido, R. L. Pederson, Y. Schrodi, W. H. Sperber, M. J. Tupy, and E. H. Wagener . 2011. Surface coating compositions and methods, US Patent 7951232, filed May 31.
   Google Scholar