Full Text:   <1526>

CLC number: TQ426.91; TQ655

On-line Access: 

Received: 2004-10-24

Revision Accepted: 2005-01-08

Crosschecked: 0000-00-00

Cited: 2

Clicked: 4388

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
1. Reference List
Open peer comments

Journal of Zhejiang University SCIENCE B 2005 Vol.6 No.5 P.373~377

10.1631/jzus.2005.B0373


Synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on active carbon


Author(s):  YANG Shui-jin, DU Xin-xian, HE Lan, SUN Ju-tang

Affiliation(s):  Department of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, China; more

Corresponding email(s):   yangshuijin@163.com

Key Words:  Tungstosilicic acid, Aceta, Ketal, Active carbon, Catalysis


YANG Shui-jin, DU Xin-xian, HE Lan, SUN Ju-tang. Synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on active carbon[J]. Journal of Zhejiang University Science B, 2005, 6(12): 373~377.

@article{title="Synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on active carbon",
author="YANG Shui-jin, DU Xin-xian, HE Lan, SUN Ju-tang",
journal="Journal of Zhejiang University Science B",
volume="6",
number="5",
pages="373~377",
year="2005",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2005.B0373"
}

%0 Journal Article
%T Synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on active carbon
%A YANG Shui-jin
%A DU Xin-xian
%A HE Lan
%A SUN Ju-tang
%J Journal of Zhejiang University SCIENCE B
%V 6
%N 5
%P 373~377
%@ 1673-1581
%D 2005
%I Zhejiang University Press & Springer

TY - JOUR
T1 - Synthesis of acetals and ketals catalyzed by tungstosilicic acid supported on active carbon
A1 - YANG Shui-jin
A1 - DU Xin-xian
A1 - HE Lan
A1 - SUN Ju-tang
J0 - Journal of Zhejiang University Science B
VL - 6
IS - 5
SP - 373
EP - 377
%@ 1673-1581
Y1 - 2005
PB - Zhejiang University Press & Springer
ER -


Abstract: 
Catalytic activity of activated carbon supported tungstosilicic acid in synthesizing 2-methyl-2-ethoxycarbonylmethyl-1,3-dioxolane, 2,4-dimethyl-2-ethoxycarbonylmethyl-1,3-dioxolane, cyclohexanone ethylene ketal, cyclohexanone 1,2-propanediol ketal, butanone ethylene ketal, butanone 1,2-propanediol ketal, 2-phenyl-1,3-dioxolane, 4-methyl-2-phenyl-1,3-dioxolane, 2-propyl-1,3-dioxolane, 4-methyl-2-propyl-1,3-dioxolane was reported. It has been demonstrated that activated carbon supported tungstosilicic acid is an excellent catalyst. Various factors involved in these reactions were investigated. The optimum conditions found were: molar ratio of aldehyde/ketone to glycol is 1/1.5, mass ratio of the catalyst used to the reactants is 1.0%, and reaction time is 1.0 h. Under these conditions, the yield of 2-methyl-2-ethoxycarbonylmethyl-1,3-dioxolane is 61.5%, of 2,4-dimethyl-2-ethoxycarbonylmethyl-1,3-dioxolane is 69.1%, of cyclohexanone ethylene ketal is 74.6%, of cyclohexanone 1,2-propanediol ketal is 80.1%, of butanone ethylene ketal is 69.5%, of butanone 1,2-propanediol ketal is 78.5%, of 2-phenyl-1,3-dioxolane is 56.7%, of 4-methyl-2-phenyl-1,3-dioxolane is 86.2%, of 2-propyl-1,3-dioxolane is 87.5%, of 4-methyl-2-propyl-1,3-dioxolane is 87.9%.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1] Dhrubojyoti, D.L., Dipak, P., Jagir, S.S., 1999. Cadmium iodide catalyzed and efficient synthesis of acetals under microwave irradiations. Chemistry Letters, 332(8):1283-1284.

[2] Hanzlik, R.P., Leinwetter, M., 1978. Reactions of epoxides and carbonyl compounds catalyzed by anhydrous copper sulfate. J. Org. Chem., 43(3):438-440.

[3] Hu, C.W., Hashimota, M., Okuhara, T., Misono, M., 1993. Catalysis by heteropoly compounds ((II. Reactions of esters and esterification catalyzed by heteropolyacids in a homogeneous liquid phase-effects of the central atom of heteropolyanions having tungsten as the addenda atom. J. Catal., 143(2):437-448.

[4] Kozhevnikov, I.V., 1998. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions. Chem. Rev., 98:171-198.

[5] Li, S.W., Fan, R.L., 1981. Handbook of Practice Organic Chemistry. Science and Technology Press, Shanghai, p.319 (in Chinese).

[6] Li, Y.Z., Huang, H.M., Jin, H., Xu, Y.Q., 1989. Aldol condensation of cyclohexanone and synthesis of acetal or ketals. Acta Scientiarum Naturaliun Universitatis Jilinensis, 2:113-116 (in Chinese).

[7] Li, T.S., Li, S.H., Li, J.T., Li, H.Z., Wu, X.X., 1996. Efficient and conveninent procedures for the formation and cleavage of steroid acetals catalyzed by montmorillonite K 10. Chinese Chemical Letters, 7(11):975-978.

[8] Mizuno, N., Misono, M., 1998. Heterogeneous catalysis. Chem. Rev., 98:199-217.

[9] Wang, C.D., Qian, W.Y., 1993. Study of catalytic synthesis of acetals and ketals with molecular sieve. Chemical World, 1:20-22 (in Chinese).

[10] Wang, C.D., Yang, X.H., Qian, W.Y., 1992a. Synthesis of acetals and ketals with solid superacid catalyst  Fine Chemicals, 9(3):4-7 (in Chinese).

[11] Wang, C.D., Niu, Y.Q., Lu, J., 1992b. Acetalation and ketal formation catalyzed by stannous oxide. Journal of Yangzhou Institute of Technology, 4(1):40-43 (in Chinese).

[12] Wang, E.B., Hu, C.W., Xu, L., 1998. Polyhydric Chemist Introduction. Chemical Industry Press, Beijing, 48:194 (in Chinese).

[13] Yang, S.J., Yu, X.Q., Liang, Y.G., Sun, J.T., 2003a. Synthesis of ethyl acetoacetate ethylene ketal catalyzed by using TiSiW12O40/TiO2. Journal of Molecular Catalysis, 17(1):61-64 (in Chinese).

[14] Yang, S.J., Chen, L.C., Sun, J.T., 2003b. Catalytic synthesis of butyric esters with TiSiW12O40/TiO2. Rare Metals, 22(1):75-77.

[15] Yu, S.X., Peng, H.Y., 1994. Catalytic synthesis of acetals and ketals with FeCl3(6H2O. Modern Chemicals, 12:29-30 (in Chinese).

[16] Zhang, J.F., Chen, T., Zhang, D.X., Shen, L., 1995. Catalytic synthesis of acetals and ketals with heteropolyacid. Flavour Fragrance Cosmetics, 4:25-27 (in Chinese).

Open peer comments: Debate/Discuss/Question/Opinion

<1>

Prof.M.Gholizadeh@Mashhad University<mostafa_gholizadeh@yahoo.com>

2010-05-31 20:10:24

Dear Prof.
Hi
I am a professor in organic chemistry at chm.Dept. of Mashhad university of IRAN.We have need to the following abow references(No:1,9,10,11,15,16)for our research.I am looking forward hearing you soon.
The Best Regards:
Mostafa Gholizadeh

Please provide your name, email address and a comment





Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou 310027, China
Tel: +86-571-87952276/87952783; E-mail: jzus@zju.edu.cn
Copyright © 2000 - Journal of Zhejiang University-SCIENCE