Preparation of methyl ester sulfonates based on sulfonation in a falling film microreactor from hydrogenated palm oil methyl esters with gaseous SO 3

Industrial and Engineering Chemistry Research

Volumn 52, Issue 10, 2013, Pages 3714-3722

  Xie, Tianming ^a   Zeng, Changfeng ^b   Wang, Chongqing ^a   Zhang, Lixiong ^a  

^a NANJING UNIVERSITY   (China)

^b NANJING TECH UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPONENTS; AGING TEMPERATURES; ENVIRONMENTALLY-FRIENDLY; FALLING FILM REACTOR; FATTY ACID METHYL ESTER; HYDROGENATED PALM OIL; METHYL ESTER SULFONATES; REACTION MECHANISM;

ANIONIC SURFACTANTS; CARBON DIOXIDE; ESTERIFICATION; ESTERS; FLOW RATE; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALM OIL; SULFONATION;

FILM PREPARATION;

EID: 84875000162     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie3028763     Document Type: Article

References (40)

1. Weil, J. K.; Stirton, A. J. Critical micelle concentrations of α -sulfonated fatty acids and their esters J. Phys. Chem 1956, 60, 899
2. Stirton, A. J.; Bistline, R. G., Jr.; Weil, J. K.; Ault, W. C.; Maurer, E. W. Sodium salts of alkyl esters of α -sulfo fatty acids wetting, lime soap dispersion, and related properties J. Am. Oil Chem. Soc. 1962, 39, 128
3. Stirton, J. α -Sulfonated fatty acids and derivatives synthesis, properties, and use J. Am. Oil Chem. Soc. 1962, 39, 490
4. Knaggs, E. A.; Yeager, J. A.; Varenyi, L.; Fischer, E. Alpha sulfo fatty esters in biologically soft detergent formulations J. Am. Oil Chem. Soc. 1965, 42, 805
5. Stein, W.; Baumann, H. α -Sulfonated fatty acids and esters: Manufacturing process, properties, and applications J. Am. Oil Chem. Soc. 1975, 52, 323
6. Kapur, B. L.; Solomon, J. M.; Bluestein, B. R. Summary of the technology for the manufacture of higher alpha-sulfo fatty acid esters J. Am. Oil Chem. Soc. 1978, 55, 549
7. Satsuki, T.; Umehara, K.; Yoneyanma, Y. Performance and physicochemical properties of α -sulfo fatty acid methyl esters J. Am. Oil Chem. Soc. 1992, 69, 672
8. Martínez, D.; Orozco, G.; Rincón, S.; Gil, I. Simulation and pre-feasibility analysis of the production process of α -methyl ester sulfonates (α -MES) Bioresour. Technol. 2010, 101, 8762
9. Foster, N. C.; Hovda, K. Manufacture of methyl ester sulfonates and other derivatives in presentation outlines of the soaps; AOCS Press: Champaign, IL, 1997.
10. Weil, J. K.; Witnauer, L. P.; Stirton, A. J. Evidence for α -sulfonation in the reaction of palmitic acid with sulfur trioxide J. Am. Oil Chem. Soc. 1952, 75, 2526
11. Weil, J. K.; Bistline, R. G., Jr.; Stirton, A. J. Sodium salts of alkyl α -sulfopalmitates and stearates J. Am. Oil Chem. Soc. 1953, 75, 4859
12. Weil, J. K.; Bistline, R. G., Jr.; Stirton, A. J. Organic synthesis; Wiley: New York, 1956.
13. Smith, F. D.; Stirton, A. J. The alpha-sulfonation of alkyl palrnitates and stearates J. Am. Oil Chem. Soc. 1967, 44, 405
14. Stein, W.; Weiss, H.; Koch, O. Sulfonation of saturated fatty acid esters of polyvalent alcohols. U.S. Patent 3,251,868, 1966.
15. Wulff, C.; Stein, W.; Koch, O.; Weiss, H. Process for the production of light colored surface active esters of sulfo-fatty acids and salts thereof. U.S. Patent 3,485,856, 1969.
16. Van Dam, M. H. H.; Corriou, J. P.; Midoux, N. Modeling and measurement of sulfur dioxide absorption rate in a laminar falling film reactor Chem. Eng. Sci. 1999, 54, 5311
17. Akanksha, Pant, K. K.; Srivastava, V. K. Modeling of sulphonation of tridecylbenzene in a falling film reactor Math. Comput. Model. 2007, 46, 1332
18. Akanksha, Pant, K. K.; Pandey, P. M.; Srivastava, V. K. Modeling of gas absorption with an exothermic reaction in a falling liquid film J. Chem. Eng. Jpn. 2006, 39, 1229
19. Talens, F. I.; Hreczuch, W.; Szymanowski, J. Ethoxylation of alcohols in falling film reactor J. Dispersion Sci. Technol. 1998, 19, 423
20. Puma, G. L.; Yue, P. L. Enhanced photocatalysis in a pilot laminar falling film slurry reactor Ind. Eng. Chem. Res. 1999, 38, 3246
21. Nagayama, M.; Okumura, O.; Sakatani, T.; Hashimoto, S.; Noda, S. Studies on sulfonation of esters of fatty acids by a continuous thin film sulfonator and its initial reaction products J. Jpn.Oil. Chem. Soc. 1975, 24, 395
22. Sheats, W. B.; MacArthur, B. W. Methyl ester sulfonate products Detergent Cosmetics 2000, 23, 89
23. Jahnisch, K.; Baerns, M.; Hessel, V.; Ehrfeld, W.; Haverkamp, V.; Löwe, H.; Wille, C.; Guber, A. Direct fuorination of toluene using elemental fluorine in gas/liquid microreactors J. Fluorine Chem. 2000, 105, 117
24. Hessel, V.; Loeb, P.; Löwe, H. Direct fluorination of aromatics with elemental fluorine in microstructured reactors Chim. Oggi. 2004, 22, 10
25. Heike, E.; David, L.; Konrad, M.; Manfred, B.; Klaus, J. Application of microstructured reactor technology for the photochemical chlorination of alkylaromatics Chimia 2002, 56, 647
26. Muller, A.; Cominos, V.; Hessel, V.; Horn, B.; Schurer, J.; Ziogas, A.; Jahnisch, K.; Hillmann, V.; Großer, V.; Jam, K. A.; Bazzanella, A.; Rinke, G.; Kraut, M. Fluidic bus system for chemical process engineering in the laboratory and for small-scale production Chem. Eng. J. 2005, 107, 205
27. Steinfeldt, N.; Abdallah, R.; Dingerdissen, U.; Jahnisch, K. Ozonolysis of acetic acid 1-vinylhexyl ester in a falling film microreactor Org. Process. Res. Dev. 2007, 11, 1025
28. Steinfeldt, N.; Bentrup, U.; Jahnisch, K. Reaction mechanism and in situ ATR spectroscopic studies of the 1-decene ozonolysis in micro-and semibatch reactors Ind. Eng. Chem. Res. 2010, 49, 72
29. Yoshimura, H.; Mandai, Y.; Hashimoto, S. Sulfonation mechanism of fatty acid methyl ester with sulfur trioxide J. Jpn. Oil. Chem. Soc. 1992, 41, 1041
30. MacArthur, B.; W. Brooks, B.; Sheats, W. B.; Foster, N. C. Meeting the challenge of methylester sulfonation; AOCS Press: Champaingn, IL, 1999.
31. Roberts, D. W.; Giusti, L.; Forcella, A. Chemistry of methyl ester sulfonates Int. News Fats, Oils Relat. Mater.. 2008, 19, 2
32. Sun, P. Y.; Wang, B.; Yao, J. F.; Zhang, L. X.; Xu, N. P. Fast synthesis of biodiesel at high throughput in microstructured reactors Ind. Eng. Chem. Res. 2010, 49, 1259
33. Battaglini, G. T.; Larsen-Zobus, J. L.; Baker, T. G. Analytical methods for alpha sulfo methyl tallowate J. Am. Oil Chem. Soc. 1986, 63, 1073
34. Commenge, J. M.; Obein, T.; Framboisier, X.; Rode, S.; Pitiot, P.; Matlosz, M. Gas-phase mass-transfer measurements in a falling-film microreactor Chem. Eng. Sci. 2011, 66, 1212
35. Talens, F. I.; Gutiérrez, J. M. Shorter communication: Estimation of the viscosity and density of lauryl alcohol/laurylsulphuric acid mixtures as a function of the temperature and laurylsulphuric acid molar fraction Chem. Eng. Res. Des. 1995, 73, 206
36. Yeong, K. K.; Gavriilidisa, A.; Zapf, R.; Hessel, V. Experimental studies of nitrobenzene hydrogenation in a microstructured falling film reactor Chem. Eng. Sci. 2004, 59, 3491
37. Yeong, K. K.; Gavriilidis, A.; Zapf, R.; Kost, H. J.; Hessel, V.; Boyde, A. Characterisation of liquid film in a microstructured falling film reactor using laser scanning confocal microscopy Exp. Therm. Fluid Sci. 2006, 30, 463
38. Parris, G. E.; Brinckman, F. E. Reactions which relate to environmental mobility of arsenic and antimony. II. Oxidation of trimethylarsine and trimethylstibine Environ. Sci. Technol. 1976, 12, 1130
39. 3-sulfonation of methyl esters Rev. Investigaciones UNAD 2005, 4, 150
40. Ho, C. D.; Chang, H.; Chen, H. J.; Chang, C. L.; Li, H. H.; Chang, Y. Y. CFD simulation of the two-phase flow for a falling film microreactor Int. J. Heat Mass Transfer 2011, 54, 2740