Ozonolysis of canola oil: A study of product yields and ozonolysis kinetics in different solvent systems

JAOCS, Journal of the American Oil Chemists' Society

Volumn 88, Issue 5, 2011, Pages 689-705

  Omonov, Tolibjon S ^a   Kharraz, Ereddad ^a   Curtis, Jonathan M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Canola oil; Oxidative cleavage; Ozonolysis

Indexed keywords

APROTIC SOLVENTS; CANOLA OIL; COMMERCIAL VIABILITY; DIFFERENT SOLVENTS; ETHYL ACETATES; HIGH MOLECULAR WEIGHT COMPOUNDS; OXIDATIVE CLEAVAGE; OZONOLYSIS; PRODUCT YIELDS; REACTION EXOTHERMICITY; SOLVENT MIXTURES;

CARBOXYLIC ACIDS; OLIGOMERS; REFRACTIVE INDEX; SIZE EXCLUSION CHROMATOGRAPHY; SOLVENTS; VOLATILE FATTY ACIDS;

OZONE;

BRASSICA NAPUS; BRASSICA NAPUS VAR. NAPUS;

EID: 79958844119     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-010-1717-4     Document Type: Article

References (42)

1. Gandini A (2008) Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41:9491-9504
2. CanolaCouncil. http://www.canolacouncil.org. Accessed 20 Aug 2010
3. Neff WE, Mounts TL, Rinsch WM, Konishi H, Elagaimy MA (1994) Oxidative stability of purified canola oil triacylglycerols with altered fatty-acid compositions as affected by triacylglycerol composition and structure. J Am Oil Chem Soc 71:1101-1109
4. Pryde EH, Anders DE, Teeter HM, Cowan JC (1960) The ozonization of methyl oleate. J Org Chem 25:618-621
5. McGuire J, Haslam P, Bond G (2006) Ozonolysis in the production of chiral fine chemicals. In: Ager D (ed) Handbook of Chiral Chemicals. CRC Press, Taylor &Francis, Boca Raton, pp 164-185
6. Graiver D, Tran P, Patrick L, Farminer K, Narayan R (2006) Modifications of soybean oil using novel ozone-based chemistry. In: Khemani KC, Scholz C (eds) Degradable polymers and materials. Principles and practice. ACS, Washington, pp 76-100
7. Bailey PS (1958) The reactions of ozone with organic compounds. Chem Rev 58:925-1010
8. Bailey PS (1978) Ozonation in organic chemistry. Academic Press, New York
9. Criegee R (1975) Mechanism of ozonolysis. Angew Chem Int Ed Engl 14:745-752
10. Fitchet CS, Laughton NG, Chappel CG, Khan ML, Tverezovskiy V, Tomkinson J, Fowler P (2005) Oil ozonolysis. U.S. Patent 2005/0010069 A1
11. Fliszar S, Carles J (1969) A quantitative investigation of ozonolysis reaction. 7. Ozonolyses of phenylethylenes in presence of oxygen-18-labeled benzaldehyde. J Am Chem Soc 91:2637-2643
12. Nishikawa N, Yamada K, Matsutani S, Higo M, Kigawa H, Inagaki T (1995) Structures of ozonolysis products of methyl oleate obtained in a carboxylic-acid medium. J Am Oil Chem Soc 72:735-740
13. Khan ML, Tomkinson J, Fitchet CS, Black MJ (2004) Oxidative cleavage of unsaturated oils and products obtained therefrom. U.S. Patent 6,768,029 B1
14. Throckmorton PE, Pryde EH (1972) Pilot run, plant design and cost-analysis for reductive ozonolysis of methyl soyate. J Am Oil Chem Soc 49:643-648
15. Tran P, Graiver D, Narayan R (2005) Ozone-mediated polyol synthesis from soybean oil. J Am Oil Chem Soc 82:653-659 (Pubitemid 46444849)
16. Yue J, Narine SS (2007) Separation and quantification of vegetable oil based polyols by high performance liquid chromatography with evaporative light scattering detection. J Am Oil Chem Soc 84:803-807 (Pubitemid 47330627)
17. Pryde EH, Anders DE, Teeter HM, Cowan JC (1961) Ozonization of soybean oil-the preparation and some properties of aldehyde oils. J Am Oil Chem Soc 38:375-379
18. Narine SS, Yue J, Kong XH (2007) Production of polyols from canola oil and their chemical identification and physical properties. J Am Oil Chem Soc 84:173-179 (Pubitemid 350091993)
19. Petrovic ZS, Zhang W, Javni I (2005) Structure and properties of polyurethanes prepared from triglyceride polyols by ozonolysis. Biomacromolecules 6:713-719 (Pubitemid 40476052)
20. Guo A, Demydov D, Zhang W, Petrovic ZS (2002) Polyols and polyurethanes from hydroformylation of soybean oil. J Environ Polym Degr 10:49-52 (Pubitemid 41444795)
21. Javni I, Petrovic ZS, Guo A, Fuller R (2000) Thermal stability of polyurethanes based on vegetable oils. J Appl Polym Sci 77:1723-1734
22. Kong X, Narine SS (2008) Physical properties of sequential interpenetrating polymer networks produced from canola oilbased polyurethane and poly (methyl methacrylate). Biomacromolecules 9:1424-1433 (Pubitemid 351757121)
23. Kong XH, Yue J, Narine SS (2007) Physical properties of canola oil based polyurethane networks. Biomacromolecules 8:3584-3589 (Pubitemid 350193760)
24. Petrovic ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:109-155 (Pubitemid 351219982)
25. Beesley TE, Buglio B, Scott RPW (2001) Quantitative chromatographic analysis. Taylor &Francis, New York
26. Boyd RK, Basic C, Bethem RA (2008) Trace quantitative analysis by mass spectrometry. Wiley, New York
27. Zaikov GE, Rakovsky SK (2009) Ozonation of organic and polymer compounds. Smithers-Rapra, Shrewsbury
28. Bantchev GB, Kenar JA, Biresaw G, Han MG (2009) Free radical addition of butanethiol to vegetable oil double bonds. J Agric Food Chem 57:1282-1290
29. Sadezky A, Chaimbault P, Mellouki A, Rompp A, Winterhalter R, Le Bras G, Moortgat GK (2006) Formation of secondary organic aerosol and oligomers from the ozonolysis of enol ethers. Atmos Chem Phys 6:5009-5024 (Pubitemid 44673540)
30. Sadezky A, Winterhalter R, Kanawati B, Rompp A, Spengler B, Mellouki A, Le Bras G, Chaimbault P, Moortgat GK (2008) Oligomer formation during gas-phase ozonolysis of small alkenes and enol ethers: new evidence for the central role of the Criegee intermediate as oligomer chain unit. Atmos Chem Phys 8:2667-2699
31. Sadowska J, Johansson B, Johannessen E, Friman R, Bronlarz- Press L, Rosenholm JB (2008) Characterization of ozonated vegetable oils by spectroscopic and chromatographic methods. Chem Phys Lipids 151:85-91 (Pubitemid 351186407)
32. Greenwood Fl, Rubinstein H (1967) Ozonolysis. 9. alkene ozonation oligomer. J Org Chem 32:3369-3374
33. Murray RW, Ramachandran V (1983) Ozonolysis of trans-ditert- butylethylene-the oligomer. J Org Chem 48:813-816
34. Razumovskii SD, Niazashvili GA, Tutorskii IA, Yuriev YN (1971) Synthesis and study of polymeric ozonides. Polym Sci USSR 13:217-228
35. Fliszar S, Gravel D, Cavalier E (1966) Étude quantitative des réactions D'ozonolyse. 2. Ozonation du trans-stilbéne. Can J Chem 44:1013-1019
36. Barton M, Ebdon JR, Foster AB, Rimmer S (2005) Complete ozonolysis of alkyl substituted ethenes at-60 C-circle: distributions of ozonide and oligomeric products. Org Biomol Chem 3:1323-1329 (Pubitemid 40538253)
37. Wanasundara U, Shahidi F (1993) Application of NMR spectroscopy to assess oxidative stability of canola and soybean oils. J Food Lipids 1:15-24
38. Choe JI, Choi HS, Kuczkowski RL (1986) Deuterium-isotope effects in propylene and ethylene ozonide. Magn Reson Chem 24:1044-1047
39. Greenwood FL (1945) Studies in ozonolysis. 1. Action of ozone on solvents used in ozonization. J Org Chem 10:414-418
40. Fliszar S, Renard J (1970) Quantitative investigation of ozonolysis reaction. 14. A simple carbonium ion stabilization approach to ozone cleavage of unsymmetrical olefins. Can J Chem 48:3002-3018
41. Narine S, Sporns P, Yue J (2009) Bioplastics, monomers thereof, and processes for the preparation thereof from agricultural feedstocks. U.S. Patent 7,538,236 B2
42. Springer H, Heymanns P (2004) Method for producing aliphatic carboxylic acids from aldehydes. U.S. Patent 6,696,582 B2