Stepwise catalytic transformations of renewable feedstock arising from plant oils

European Journal of Lipid Science and Technology

Volumn 115, Issue 5, 2013, Pages 490-500

  Dupé, Antoine ^a,b   Le Ravalec, Virginie ^a,b   Fischmeister, Cédric ^a   Bruneau, Christian ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b ADEME   (France)

Author keywords

Allylic substitution; Diels Alder reaction; Ene yne cross metathesis; Fatty acid esters; Ruthenium catalysis

Indexed keywords

ALNUS;

EID: 84877689984     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201200364     Document Type: Article

References (67)

1. Philippe, M., Didillon, B., Gilbert, L., Industrial commitment to green and sustainable chemistry: Using renewable materials & eco-friendly processes and ingredients in cosmetics. Green Chem. 2012, 14, 952-956.
2. Vennestrøm, P. N. R., Osmundsen, C. M., Christensen, C. H., Taarning, E., Beyond petrochemicals: The renewable chemicals industry. Angew. Chem. Int. Ed. 2011, 50, 10502-10509.
3. Marshall, A.-L., Alaimo, P. J., Useful products from complex starting materials: Common chemicals from biomass feedstocks. Chem. Eur. J. 2010, 16, 4970-4980.
4. Christensen, C. H., Raas-Hansen, J., Marsden, C. C., Taarning, E., Egeblad, K., The renewable chemicals industry. ChemSusChem 2008, 1, 283-289.
5. Gallezot, P., Catalytic conversion of biomass: Challenges and issues. ChemSusChem 2008, 1, 734-737.
6. Corma, A., Iborra, S., Velty, A., Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 2007, 107, 2411-2502.
7. Dodds, D. R., Gross, R. A., Chemicals from biomass. Science 2007, 318, 1250-1251.
8. Biermann, U., Bornscheuer, U., Meier, M. A. R., Metzger, J. O., Schäfer, H. J., Oils and fats as renewable raw materials in chemistry. Angew. Chem. Int. Ed. 2011, 50, 3854-3871.
9. Metzger, J. O., Bornscheuer, U., Lipids as renewable resources: Current state of chemical and biotechnological conversion and diversification. Appl. Microbiol. Biotechnol. 2006, 71, 13-22.
10. Biermann, U., Friedt, W., Lang, S., Lühs, W. et al., New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew. Chem. Int. Ed. 2000, 39, 2206-2224.
11. Behr, A., Perez Gomes, J., The refinement of renewable resources: New important derivatives of fatty acids and glycerol. Eur. J. Lipid Sci. Technol. 2010, 112, 31-50.
12. Montero de Espinosa, L., Meier, M. A. R., Plant oils: The perfect renewable resource for polymer science ?! Eur. Polym. J. 2011, 47, 837-852.
13. Xia, Y., Larock, R. C., Vegetable oil-based polymeric materials: Synthesis, properties, and applications. Green Chem. 2010, 12, 1893-1909.
14. Meier, M. A. R., Metzger, J. O., Schubert, U. S., Plant oil renewable resources as green alternatives in polymer science. Chem. Soc. Rev. 2007, 36, 1788-1802.
15. Petrovic, Z. S., Polymers from biological oils. Polym. Rev. 2008, 48, 109-155.
16. Trzaskowski, J., Quinzler, D., Bährle, C., Mecking, S., Aliphatic long-chain C20 polyesters from olefin metathesis. Macromol. Rapid Commun. 2011, 32, 1352-1356.
17. Petrovi, Z. S., Mili, J., Xu, Y., Cvetkovi, I., A chemical route to high molecular weight vegetable oil-based polyhydroxyalkanoate. Macromolecules 2010, 43, 4120-4125.
18. Quinzler, D., Mecking, S., Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization. Angew. Chem. Int. Ed. 2010, 49, 4306-4308.
19. Cole-Hamilton, D. J., Nature's polyethylene. Angew. Chem. Int. Ed. 2010, 49, 8564-8566.
20. Quinzler, D., Mecking, S., Renewable resource-based poly(dodecyloate) by carbonylation polymerization. Chem. Commun. 2009, 5400-5402.
21. Rybak, A., Meier, M. A. R., Acyclic diene metathesis with a monomer from renewable resources: Control of molecular weight and one-step preparation of block copolymers. ChemSusChem 2008, 1, 542-547.
22. Dubois, J. L., Method for the synthesis of ω-amino alkanoic fatty acids. Patent WO2008104722(A2), Arkema, 2008.
23. Kreye, O., Türünç, O., Sehlinger, A., Rackwitz, J., Meier, M. A. R., Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction. Chem. Eur. J. 2012, 18, 5767-5776.
24. More, A. S., Gadenne, B., Alfos, C., Cramail, H., AB type polyaddition route to thermoplastic polyurethanes from fatty acid derivatives. Polym. Chem. 2012, 3, 1594-1605.
25. Gonzalez-Paz, R. J., lluch, C., Lligadas, G., Ronda, J. C. et al., A green approach toward oleic- and undecylenic acid-derived polyurethanes. J. Polym. Sci. A Polym. Chem. 2011, 49, 2407-2416.
26. Stemmelen, M., Pessel, F., Lapinte, V., Caillol, S. et al., A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thio-ene reaction to the study of the final material. J. Polym. Sci. A Polym. Chem. 2011, 49, 2434-2444.
27. More, A. S., Palaskar, D. V., Cloutet, E., Gadenne, B. et al., Aliphatic polycarbonates and poly(ester carbonate)s from fatty acid drived monomers. Polym. Chem. 2011, 2, 2796-2803.
28. Behr, A., Westfechtel, A., Perez Gomes, J., Catalytic processes for the technical use of natural fats and oils. Chem. Eng. Technol. 2008, 31, 700-714.
29. Ohlmann, D. M., Gooβen, L. J., Dieter, M., Regioselective synthesis of β-aryl- and β-amino-substituted aliphatic esters via rhodium-catalyzed tandem double bond migration/conjugate addition. Chem. Eur. J. 2010, 17, 9508-9519.
30. Gooβen, L. J., Ohlmann, D. M., Dierker, M., Silver triflate-catalysed synthesis of γ-lactones from fatty acids. Green Chem. 2010, 12, 197-200.
31. Dupé, A., Achard, M., Fischmeister, C., Bruneau, C., Methyl ricinoleate as platform chemical for simultaneous production of fine chemicals and polymer precursors. ChemSusChem 2012, 5, 2249-2254.
32. Malacea, R., Fischmeister, C., Bruneau, C., Dubois, J.-L. et al., Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile. Green Chem. 2009, 11, 152-155.
33. Miao, X., Fischmeister, C., Bruneau, C., Dixneuf, P. H., A direct route to bifunctional aldehyde derivatives via self- and cross-metathesis of unsaturated aldehydes. ChemSusChem 2009, 2, 542-545.
34. Rybak, A., Meier, M. A. R., Cross-metathesis of fatty acid derivatives with methyl acrylate: Renewable raw materials for the chemical industry. Green Chem. 2007, 9, 1356-1361.
35. Rybak, A., Meier, M. A. R., Cross-metathesis of oleyl alcohol with methyl acrylate: Optimization of reaction conditions and comparison of their environmental impact. Green Chem. 2008, 10, 1099-1104.
36. Behr, A., Perez Gomes, J., The cross-metathesis of methyl oleate with cis-2-buten-1, 4-diyl diacetate and the influence of protecting groups. Beilstein J. Org. Chem. 2011, 7, 1-8.
37. Miao, X., Malacea, R., Fischmeister, C., Bruneau, C., Dixneuf, P. H., Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: A key step toward long-chain bifunctional and amino acid compounds. Green Chem. 2011, 13, 2911-2919.
38. Miao, X., Fischmeister, C., Dixneuf, P. H., Bruneau, C. et al., Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis. Green Chem. 2012, 14, 2179-2183.
39. Jacobs, T., Rybak, A., Meier, M. A. R., Cross-metathesis reactions of allyl chloride with fatty acid methyl esters: Efficient synthesis of α, ω-difunctional chemical intermediates from renewable raw materials. Appl. Catal. A Gen. 2009, 353, 32-35.
40. Miao, X., Fischmeister, C., Dixneuf, P. H., Bruneau, C. et al., Tandem catalytic acrylonitrile cross-metathesis and hydrogenation of nitriles with ruthenium catalysts: Direct access to linear α, ω-aminoesters from renewables. ChemSusChem 2012, 5, 1410-1414.
41. Miao, X., Dixneuf, P. H., Fischmeister, C., Bruneau, C., A green route to nitrogen-containing groups: The acrylonitrile cross-metathesis and applications to plant oils derivatives. Green Chem. 2011, 13, 2258-2271.
42. Bruneau, C., Fischmeister, C., Miao, X., Malacea, R., Dixneuf, P. H., Cross-metathesis with acrylonitrile and applications to fatty acid derivatives. Eur. J. Lipid Sci. Technol. 2010, 112, 3-9.
43. Abbas, M., Slugovc, C., Optimized reaction conditions for the cross-metathesis of methyl oleate and oleylamine with ethyl acrylate. Monatsh Chem. 2012, 143, 669-673.
44. Schrodi, Y., Ung, T., Vargas, A., Mkrtumyan, G. et al., Ruthenium olefin metathesis catalysts for the ethenolysis of renewable feedstocks. Clean 2008, 36, 669-673.
45. Thurier, C., Fischmeister, C., Bruneau, C., Olivier-Bourbigou, H., Dixneuf, P. H., Ethenolysis of methyl oleate in room-temperature ionic liquids. ChemSusChem 2008, 1, 118-122.
46. Burdett, K. A., Harris, L. D., Margl, P., Maughon, B. R. et al., Renewable monomer feedstocks via olefin metathesis: Fundamental mechanistic studies of methyl oleate ethenolysis with the first-generation Grubbs catalyst. Organometallics 2004, 23, 2027-2047.
47. Mol, J. C., Application of olefin metathesis in oleochemistry: An example of green chemistry. Green Chem. 2002, 4, 5-13.
48. Patel, J., Elaridi, J., Roy Jackson, W., Robinson, A. J. et al., Cross-metathesis of unsaturated natural oils with 2-butene. High conversion and productive catalyst turnovers. Chem. Commun. 2005, 5546-5547.
49. Patel, J., Mujcinovic, S., Roy Jackson, W., Robinson, A. J. et al., High conversion and productive catalyst turnovers in cross-metathesis reactions of natural oils with 2-butene. Green Chem. 2006, 8, 450-454.
50. Fischmeister, C., Bruneau, C., Ene-yne cross-metathesis with ruthenium carbene catalysts. Beilstein J. Org. Chem. 2011, 7, 156-166;
51. Diver, S. T., Ruthenium vinyl carbene intermediates in enyne metathesis. Coord. Chem. Rev. 2007, 251, 671-701.
52. Le Ravalec, V., Fischmeister, C., Bruneau, C., First transformation of unsaturated fatty esters involving enyne cross-metathesis. Adv. Synth. Catal. 2009, 351, 1115-1122.
53. Le Ravalec, V., Dupé, A., Fischmeister, C., Bruneau, C., Improving sustainability in ene-yne cross-metathesis for transformation of unsaturated fatty esters. ChemSusChem 2010, 3, 1291-1297.
54. Kotha, S., Meshram, M., Tiwari, A., Advanced approach to polycyclics by a synergistic combination of enyne metathesis and Diels-Alder reaction. Chem. Soc. Rev. 2009, 38, 2065-2092.
55. Schürer, S. C., Blechert, S., A versatile synthesis of substituted tetrahydropyridines. Tetrahedron Lett. 1999, 40, 1877-1880.
56. Stragies, R., Voigtmann, U., Blechert, S., Improved yne-ene-cross-metathesis utilizing a dihydroimidazole carbene ruthenium complex. Tetrahedron Lett. 2000, 41, 5465-5468.
57. Biermann, U., Butte, W., Eren, T., Haase, D., Metzger, J. O., Regio- and stereoselective Diels-Alder additions of maleic anhydride to conjugated triene fatty acids methyl esters. Eur. J. Org. Chem. 2007, 3859-3862.
58. Biermann, U., Jungbauer, A., Metzger, J. O., Esters of maleinized fatty compounds as plasticizers. Eur. J. Lipid Sci. Technol. 2012, 114, 49-54.
59. Behr, A., Fiene, M., Naendrup, F., Schürmann, K., Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives by Diels-Alder reactions at unsaturated fatty esters. Eur. J. Lipid. Sci. Technol. 2000, 102, 342-350.
60. Eschig, S., Philipp, C., Salthammer, T., Synthesis of fatty acid-based 3, 6-disubstituted-1, 2, 3, 6-tetrahydro-phthalic acid anhydride derivatives. Eur. J. Lipid. Sci. Technol. 2012, 115, 101-110.
61. Fischmeister, C., Doucet, H., Greener solvents for ruthenium and palladium-catalysed aromatic C-H bond functionalisation. Green Chem. 2011, 13, 741-753.
62. Rickerby, J., Vallet, M., Bernardinelli, G., Viton, F., Kündig, E. P., Ruthenium-Lewis acid catalyzed asymmetric Diels-Alder reactions between dienes and α, β-unsaturated ketones. Chem. Eur. J. 2007, 13, 3354-3368.
63. Bruneau, C., Achard, M., Allylic ruthenium(IV) complexes in catalysis. Coord. Chem. Rev. 2012, 256, 525-536.
64. Bruneau, C., Renaud, J.-L., Demerseman, B., Pentamethylcyclopentadienyl-ruthenium catalysts for regio- and enantioselective allylation of nucleophiles. Chem. Eur. J. 2006, 12, 5178-5187.
65. Zhang, H.-J., Demerseman, B., Toupet, L., Xi, Z., Bruneau, C., Ruthenium-catalyzed nucleophilic allylic substitution reactions from β-silylated allylic carbonates. Organometallics 2009, 28, 5173-5182.
66. 6] complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates. Adv. Synth. Catal. 2008, 350, 1601-1609.
67. Miao, X., Fischmeister, C., Bruneau, C., Dixneuf, P., Dimethyl carbonate: An eco-friendly solvent in ruthenium-catalysed olefin metathesis transformations. ChemSusChem 2008, 1, 813-816.