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Study on the Synthesis and Properties of Novel Alkyl Methylnaphthalene Sulfonate Surfactants

Part 1 Synthesis of Monoalkylated Methylnaphthalene Intermediates for Surfactants

Untersuchung über Synthese und Eigenschaften von neuartigen Alkylmethylnaphtalinsulfonat-Tensiden. Teil 1: Synthese von monoalkylierten Methylnaphtalin-Intermediärverbindungen für Tenside
Zhao Zhongkui , Li Zongshi , Qiao Weihong and Cheng Lubo

Abstract

A series of high purity monoalkyl methylnaphthalene intermediates were prepared by alkylation of β-methylnaphthalene with a series of different chain lengths of n-bromoalkanes. Gas chromatography and gas chromatography-mass spectrometry were used as appropriate methods for this technology. The reaction conditions were optimized. The effect of dosage of catalysts, the molar ratio of β-methyl naphthalene to bromoalkane and of the solvent to β-methyl naphthalene, the reaction time as well as the temperature had also been investigated in detail. The optimal reaction conditions of alkylation have been achieved, and the reaction results were discussed. Based on the optimal reaction conditions, a series of monoalkylmethylnaphthalene intermediates, hexyl-, octyl-, decyl-, dodecyl-, tetra-decyl-methyl-naphthalenes had been prepared.

Kurzfassung

Eine Reihe von hochreinen monoalkylierten Methylnaphtalin-Intermediärverbindungen wurde durch Alkylierung von β-Methylnaphtalin mit n-Bromalkanen verschiedener Kettenlänge gewonnen. Zur Bestimmung und Quantifizierung wurden die Gaschromatographie und Gaschromatographie-Massenspektrometrie als geeignete Methoden eingesetzt. Die Reaktionsbedingungen wurden optimiert. Der Einfluß der Katalysatordosierung, des molaren Verhältnisses von β-Methylnaphtalin zu n-Bromalkan, des Lösungsmittels zu β-Methylnaphtalin, der Reaktionszeit und der Reaktionstemperatur wurde eingehend untersucht. Optimierte Reaktionsbedingungen der Alkylierung wurden gefunden und deren Ergebnisse diskutiert. Mit Hilfe der optimierten Reaktionsbedingungen konnte eine Serie von monoalkylierten Methylnaphtalin-Intermediärverbindungen, Hexyl-, Octyl-, Decyl-, Dodecyl-, Tetradecylmethylnaphtalin dargestellt werden.


Correspondence to Dr. Zhao Zhongkui State Key Laboratory of Fine Chemicals, Dalian University of Technology, 158 Zhongshan Road, Dalian, 116012, P.R. China, Tel.: 86-4 11-8 99 38 78, Fax: 86-4 11-3 68 32 29, E-mail: ,

Zhao Zhongkui was born in 1977. Now he is a PhD candidate at Dalian University of Technology. His main field of research is the synthesis and physical chemistry of surfactants. He has published fifteen papers.

Prof. Li Zongshi was born in 1936. He obtained a BS degree from Dalian University of Technology in 1960. Since then he has been working in the department of fine chemicals at Dalian University of Technology. His focus is on synthesis of surfactants and their applications.

Qiao Weihong was born in 1968. She obtained an MSc from Dalian University of Technology in1994 and a Ph D from the same university in 2000. Since 1994, she has been teaching and working in Dalian University of Technology. Her main field of research is the synthesis and physicial chemistry of surfactants.

Prof. Cheng Lubo was born in 1933, he obtained a BS from Dalian University of Technology in 1955. Since then he has been working in the department of fine chemicals at Dalian University of Technology. His focus is on synthesis of surfactants, dyes and their applications.


References

1. YuJiayong, SongWanchao, LiZhipinget al.: Fundamental Research and Progress in Chemical Complex Oil-displacing System. Beijing. Chinese Petroleum Chemical Press. (2002) 279300.Search in Google Scholar

2. CuiZhenggang and YinFushan: Microemulsion Technology and Application. Chinese Light Industry Press. (1992).Search in Google Scholar

3. LiuCheng: Application of Surfactants. Beijing, Beijing University press. (1992).Search in Google Scholar

4. WangXing, XuLongya, WangQingxiaet al.: Petroleum Chemical Industry26 (1997) 267272.Search in Google Scholar

5. WangErren, ZhangJinchang and LiChengyue: Modern Chemical Industry22(2) (2002) 1114.Search in Google Scholar

6. Taiseki, K. and Hirohisa, K.: Chlorinaftd Petroleum VI. Synthesis of detergents from Chlorinated kerosine. J. chem. sec. Japan., Ind. Chem. sect.58 (1955) 2325.Search in Google Scholar

7. Zhao, Z. K., Qiao, W. H., LiH. M.et al.: A study on the long-chain alkylation of β-methylnaphthalene with olefins. Journal of Dalian University of Technology (in Chinese)44(1) (2004) 3943.Search in Google Scholar

8. Cheng, L. B.: Synthesis and Application of Fine Chemicals. Dalian: Dalian University of Technology Press (2002) 912.Search in Google Scholar

9. Yao, M. Z., Cheg, L. B. and Wang, J. R.: Synthesis Principle of Fine Chemicals. Beijing: Chinese Petrifaction Press (1992) 303309.Search in Google Scholar

10. Zhao, Z. K., Qiao, W. H., Wang, X. N.et al.: Study on the Long-chain Alkylation of β-Methylnaphthalene by Gas Chromatography/Mass Spectrometry. Chinese Journal of Analytical Chemistry31 (11) (2003) 13001306.Search in Google Scholar

11. Liu, G. Q. and Yu, Y. L.: Technique of Chromatographic Column. Beijing: Chemical Industry Press (2001) 3698.Search in Google Scholar

12. Zhao, Z. K., Qiao, W. H., Wang, X. N.et al.: Analysis of Long-chain Alkylation products of β-Methylnaphthalene by Capillary Gas Chromatography – Mass Spectrometry. Journal of Instrumental Analysis (in Chinese)22(6) (2003) 7477.Search in Google Scholar

13. Gao, K. Y.: Analysis of Fine Chemicals. Beijing: Chemical Industry Press (2002) 99125.Search in Google Scholar

Received: 2003-11-18
Published Online: 2013-05-01
Published in Print: 2004-04-01

© 2004, Carl Hanser Publisher, Munich

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