Solvent-free acid-catalyzed ring-opening of epoxidized oleochemicals using stearates/stearic acid, and its applications

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 9, 2012, Pages 2179-2189

  Ahn, Byung Jun Kollbe ^a   Kraft, Stefan ^a,b   Sun, Xiuzhi Susan ^a  

^a KANSAS STATE UNIVERSITY   (United States)

^b Kansas State University ^*  (United States)

Author keywords

Acid catalyzed ring opening; Epoxidized methyl oleate; Epoxidized soybean oil; Grease

Indexed keywords

CATALYSIS; CATALYSTS; LUBRICATING GREASES; REINFORCED PLASTICS; SOLVENTS; SOYBEAN OIL;

ACID CATALYZED RING OPENINGS; ENVIRONMENTAL ISSUES; EPOXIDE RING OPENING; EPOXIDIZED METHYL OLEATES; EPOXIDIZED SOYBEAN OIL; FATTY ACID DERIVATIVES; HIGH-EFFICIENT CATALYSTS; MAGNESIUM STEARATE;

FATTY ACIDS;

GLYCINE MAX;

EID: 84859755925     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204275q     Document Type: Article

References (65)

1. Carlsson, A. S. Plant oils as feedstock alternatives to petroleum-A short survey of potential oil crop platforms. Biochimie 2009, 91 (6), 665-670.
2. Metzger, J. O.; Bornscheuer, U. Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl. Microbiol. Biotechnol. 2006, 71 (1), 13-22. (Pubitemid 43807457)
3. Salimon, J.; Salih, N.; Yousif, E. Biolubricants: Raw materials, chemical modifications and environmental benefits. Eur. J. Lipid Sci. Technol. 2010, 112 (5), 519-530.
4. Bozell, J. J. Feedstocks for the future - Biorefinery production of chemicals from renewable carbon. Clean: Soil, Air, Water 2008, 36 (8), 641-647.
5. 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 (11), 1788-1802.
6. Metzger, J. O. Fats and oils as renewable feedstock for chemistry. Eur. J. Lipid Sci. Technol. 2009, 111 (9), 865-876.
7. Eissen, M.; Metzger, J. O.; Schmidt, E.; Schneidewind, U. 10 years after Rio-Concepts on the contribution of chemistry to a sustainable development. Angew. Chem., Int. Ed. 2002, 41 (3), 414-436. (Pubitemid 34146064)
8. Behr, A.; Gomes, J. P., The refinement of renewable resources: New important derivatives of fatty acids and glycerol. Eur. J. Lipid Sci. Technol. 112, (1), 31-50.
9. Hörner, D. Recent trends in environmentally friendly lubricants. J. Synth. Lubr. 2002, 18 (4), 327-347. (Pubitemid 34159622)
10. Bondioli, P. Lubricants and hydraulic fluids. In Oleochemical Manufacture and Applications; Gunstone, F. D., Hamilton, R. J., Eds.; Sheffield Academic Press: London, 2001; pp 74-105.
11. Erhan, S. Z.; Asadauskas, S. Lubricant basestocks from vegetable oils. Ind. Crops Prod. 2000, 11 (2-3), 277-282. (Pubitemid 30172127)
12. Behr, A.; Westfechtel, A.; Gomes, J. P. Catalytic processes for the technical use of natural fats and oils. Chem. Eng. Technol. 2008, 31 (5), 700-714. (Pubitemid 351712127)
13. Xia, Y.; Larock, R. C. Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem. 2010, 12 (11), 1893-1909.
14. Campanella, A.; Rustoy, E.; Baldessari, A.; Baltanás, M. A. Lubricants from chemically modified vegetable oils. Bioresour. Technol. 2010, 101 (1), 245-254.
15. Adhvaryu, A.; Erhan, S. Z. Epoxidized soybean oil as a potential source of high-temperature lubricants. Ind. Crops Prod. 2002, 15 (3), 247-254. (Pubitemid 34231343)
16. Lu, H.; Sun, S. D.; Bi, Y. L.; Yang, G. L.; Ma, R. L.; Yang, H. F. Enzymatic epoxidation of soybean oil methyl esters in the presence of free fatty acids. Eur. J. Lipid Sci. Technol. 2010, 112 (10), 1101-1105.
17. Andjelkovic, D. D.; Larock, R. C. Novel rubbers from cationic copolymerization of soybean oils and dicyclopentadiene. 1. Synthesis and characterization. Biomacromolecules 2006, 7 (3), 927-936.
18. Helling, R. K.; Russell, D. A. Use of life cycle assessment to characterize the environmental impacts of polyol production options. Green Chem. 2009, 11 (3), 380-389.
19. Burgos, N.; Fiori, S.; Jiménez, A. Recent Advances in Research on Biodegradable Polymers and Sustainable Composites; Nova Science Publisher: Hauppauge, NY, 2009.
20. Erhan, S. Z.; Sharma, B. K.; Liu, Z.; Adhvaryu, A. Lubricant Base Stock Potential of Chemically Modified Vegetable Oils. J. Agric. Food Chem. 2008, 56 (19), 8919-8925.
21. Legisa, I.; Picek, M.; Nahal, K. Some experience with biodegradable lubricants. J. Synth. Lubr. 1997, 13 (4), 347-360. (Pubitemid 126614939)
22. Salimon, J.; Salih, N.; Yousif, E. Industrial development and applications of plant oils and their biobased oleochemicals. Arabian J. Chem. 2010, DOI: http://dx.doi.org/10.1016/j.arabjc.2010.08.007.
23. Lathi, P. S.; Mattiasson, B. Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil. Appl. Catal., B 2007, 69 (3-4), 207-212. (Pubitemid 44959857)
24. Aluyor, E. O.; Obahiagbon, K. O.; Ori-jesu, M. Biodegradation of vegetable oils: A review. Sci. Res. Essays 2009, 4 (6), 543-548.
25. Salimon, J.; Salih, N. Substituted Esters of Octadecanoic Acid as Potential Biolubricants. Eur. J. Sci. Res. 2009, 31, 273-279.
26. Salimon, J.; Salih, N. Preparation and Characteristic of 9,10-Epoxyoleic Acid α-Hydroxy Ester Derivatives as Biolubricant Base Oil. Eur. J. Sci. Res. 2009, 31, 265-272.
27. Salimon, J.; Salih, N. Improved low temperature properties of 2-ethylhexyl 9(10)-hydroxy-10(9)-acyloxystreate derivatives. Eur. J. Sci. Res. 2009, 31, 583-591.
28. Salimon, J.; Salih, N. Modification of Epoxidized Ricinoleic Acid for Biolubricant Base Oil With Improved Flash and Pour Points. Asian J. Chem. 2010, 22 (7), 5468-5476.
29. Sin, S. N.; Chua, H. Degradation pathway of persistent branched fatty acids in natural anaerobic ecosystem. Chemosphere 2000, 41 (1-2), 149-153. (Pubitemid 30226558)
30. Campanella, A.; Baltanas, M. A. Degradation of the oxirane ring of epoxidized vegetable oils with solvated acetic acid using cationexchange resins. Eur. J. Lipid Sci. Technol. 2004, 106 (8), 524-530. (Pubitemid 39220992)
31. Campanella, A.; Baltanas, M. A. Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid heterogeneous reaction systems. Chem. Eng. J. 2006, 118 (3), 141-152.
32. Campanella, A.; Baltanas, M. A. Degradation of the oxirane ring of epoxidized vegetable oils in a liquid-liquid-solid heterogeneous reaction system. Chem. Eng. Process. 2007, 46 (3), 210-221. (Pubitemid 44854297)
33. Schuster, H.; Rios, L. A.; Weckes, P. P.; Hoelderich, W. F. Heterogeneous catalysts for the production of new lubricants with unique properties. Appl. Catal., A 2008, 348 (2), 266-270.
34. Moser, B. R.; Sharma, B. K.; Doll, K. M.; Erhan, S. Z. Diesters from oleic acid: Synthesis, low temperature properties, and oxidation stability. J. Am. Oil Chem. Soc. 2007, 84 (7), 675-680. (Pubitemid 47167282)
35. Pelaez, M.; Orellana, C.; Marques, A.; Busquets, M.; Guerrero, A.; Manresa, A. Natural estolides produced by Pseudomonas sp 42A2 grown on oleic acid: Production and characterization. J. Am. Oil Chem. Soc. 2003, 80 (9), 859-866.
36. Plattner, R. D.; Paynewahl, K.; Tjarks, L. W.; Kleiman, R. Hydroxy acids and estolide triglycerides of Heliophila amplexicaulis L.f. seed oil. Lipids 1979, 14 (6), 576-579.
37. Harry-O'kuru, R. E.; Isbell, T. A.; Weisleder, D. Synthesis of estolide esters from cis-9-octadecenoic acid estolides. J. Am. Oil Chem. Soc. 2001, 78 (3), 219-222. (Pubitemid 32419474)
38. Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Metal saltpromoted alcoholysis of 1,2-epoxides. Synlett 1992, 8, 673-676.
39. Chini, M.; Crotti, P.; Macchia, F. Metal-salts as new catalysts for mild and efficient aminolysis of oxiranes. Tetrahedron Lett. 1990, 31 (32), 4661-4664. (Pubitemid 20226237)
40. Chini, M.; Crotti, P.; Macchia, F. Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxide. J. Org. Chem. 1991, 56 (20), 5939-5942.
41. Chini, M.; Crotti, P.; Flippin, L. A.; Macchia, F.; Pineschi, M. Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis- and transoxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate. J. Org. Chem. 1992, 57 (5), 1405-1412.
42. Parker, R. E.; Isaacs, N. S. Mechanisms Of Epoxide Reactions. Chem. Rev. 1959, 59 (4), 737-799.
43. Paterson, I.; Berrisford, D. J. Meso epoxides in asymmetric synthesis: enantioselective opening by nucleophiles in the presence of chiral Lewis acids. Angew. Chem., Int. Ed. Engl. 1992, 31 (9), 1179-1180.
44. Holland, J. M.; Lewis, M.; Nelson, A. Desymmetrization of a centrosymmetric diepoxide: Efficient synthesis of a key intermediate in a total synthesis of hemibrevetoxin B. J. Org. Chem. 2003, 68 (3), 747-753. (Pubitemid 36176595)
45. McBee, E. T.; Hathaway, C. E.; Roberts, C. W. The Ringcleavage Reactions of 1,1,1-Trifluoro-2,3-epoxypropane. J. Am. Chem. Soc. 1956, 78 (15), 3851-3854.
46. Chini, M.; Crotti, P.; Flippin, L. A.; Macchia, F. Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. Synthesis and reactions of the cis- and trans-oxides derived from 4-(benzyloxy) cyclohexene. J. Org. Chem. 1990, 55 (14), 4265-4272.
47. Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C.; Macchia, F. Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 4. Synthesis and reactions of the cis- and transoxides derived from 3-[(benzyloxy)methyl]cyclohexene. J. Org. Chem. 1992, 57 (6), 1713-1718.
48. Ramachandran, P. V.; Gong, B.; Brown, H. C. Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of Trifluoromethyloxirane. A General Synthesis in High Optical Purities of .alpha.-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide. J. Org. Chem. 1995, 60 (1), 41-46.
49. Thompson, D. H.; Svendsen, C. B.; Di Meglio, C.; Anderson, V. C. Synthesis of Chiral Diether and Tetraether Phospholipids: Regiospecific Ring Opening of Epoxy Alcohol Intermediates Derived from Asymmetric Epoxidation. J. Org. Chem. 1994, 59 (11), 2945-2955.
50. Jones, R. J.; Rapoport, H. Enantiospecific synthesis of an aziridinobenzazocinone, an advanced intermediate containing the core nucleus of FR900482 and FK973. J. Org. Chem. 1990, 55 (4), 1144-1146. (Pubitemid 20124036)
51. Ley, S. V.; Redgrave, A. J. Microbial Oxidation in Synthesis: Concise Preparation of (+)-Conduritol F from Benzene. Synlett 1990, 1990 (07), 393-394.
52. Ahn, B. K.; Kraft, S.; Sun, X. S. Chemical pathways of epoxidized and hydroxylated fatty acid methyl esters and triglycerides with phosphoric acid. J. Mater. Chem. 2011, 21 (26), 9498-9505.
53. McRae, J. A.; Moir, R. Y.; Haynes, J. W.; Ripley, L. G. Methanolysis of Stereoisomeric Oxides of 3-Methoxycyclohexene. J. Org. Chem. 1952, 17 (12), 1621-1629.
54. Lemieux, R. U.; Kullnig, R. K.; Moir, R. Y. The configurations of the 3-Methoxycyclohexene Oxides. A Novel Application of Proton Magnetic Resonance Spectroscopy to the Determination of Structure and Configuration. J. Am. Chem. Soc. 1958, 80 (9), 2237-2242.
55. Reeve, W.; Christoffel, I. The Reaction of Styrene Oxide with Methanol. J. Am. Chem. Soc. 1950, 72 (4), 1480-1483.
56. 12]. J. Am. Chem. Soc. 1968, 90 (2), 319-326.
57. Phan, T. B.; Mayr, H. Comparison of the nucleophilicities of alcohols and alkoxides. Can. J. Chem. 2005, 83 (9), 1554-1560.
58. Golumbic, C.; Cottle, D. L. The Reaction of Styrene Oxide with Methylmagnesium Iodide. J. Am. Chem. Soc. 1939, 61 (5), 996-1000.
59. Federici, C.; Righi, G.; Rossi, L.; Bonini, C.; Chiummiento, L.; Funicello, M. Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols. Tetrahedron Lett. 1994, 35 (5), 797-800. (Pubitemid 24067994)
60. Bonini, C.; Righi, G. Diols obtained via chemoselective and regioselective ring-opening of epoxy alcohols-a straightforward synthesis of 2S,3S-octanediol. Tetrahedron 1992, 48 (8), 1531-1538.
61. Bonini, C.; Righi, G.; Sotgiu, G. Regioselective Opening of epoxy alcohols-mild chemoselective and stereoselective preparation of iodohydrins and 1,2-diols. J. Org. Chem. 1991, 56 (21), 6206-6209.
62. Forsberg, J. W. Magnesium-containing greases and method for their preparation. U.S. Patent 4,200,544, 1980.
63. Koivisto, M.; Jalonen, H.; Lehto, V. P. Effect of temperature and humidity on vegetable grade magnesium stearate. Powder Technol. 2004, 147 (1-3), 79-85. (Pubitemid 39575133)
64. Upadhyay, D.; Mohanty, S.; Nayak, S. K.; Parvaiz, M. R.; Panda, B. P. Impact Modification of Poly(trimethylene terephthalate)/ Polypropylene Blend Nanocomposites: Fabrication and Characterization. J. Appl. Polym. Sci. 2011, 120 (2), 932-943.
65. Chuang, H. K.; Han, C. D. Rheological behavior of blends of nylon with a chemically modified polyolefin. Adv. Chem. Ser. 1984, 206, 171-183.