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A green route to 1,2-cyclohexanediol via the hydrolysis of cyclohexene oxide catalyzed by water

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Abstract

Effective hydrolysis of cyclohexene oxide (CHO) was conducted by heating in water between 100 and 140 °C without another catalyst. It provided 100 % purity and 100 % yield of trans-1,2-cyclohexanediol (1,2-CHD) with five times of H2O to CHO at 120 °C for 6 h. These intermediates of polyether polyols could be totally decomposed to 1,2-CHD (monomer) by hot water under the same condition. The improved process eliminates the purification and markedly reduces the cost of 1,2-CHD in the follow-up industrial production. The main factors, such as reaction temperature, time, and water volume, were investigated. It was proposed that water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis of CHO and polymers.

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Notes

  1. A large scale experiment under optimized reaction conditions was carried out in a mechanical stirring stainless autoclave of 250 mL. CHO (1 mol, 98.0 g) and distilled water (5 mol, 90.0 mL) were mixed and the resulting suspension was stirred at 900 rpm and at a temperature of 120 °C ±1 for 6 h. After completion, the mixture was concentrated under reduced pressure to give 113.2 g solid product. The separated yield was 97.6 %, mp 101.5–102.3 °C.

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Acknowledgments

We acknowledge China National Funds for Distinguished Young Scientists (21106030) and Hebei Postdoctoral Sustentation Fund for the financial support. We also thank Dr. Tianyong Zhang from Tianjin University for useful comments and improving the English during the preparation of this manuscript.

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Authors and Affiliations

  1. Institute of Green Chemical Technology, Hebei University of Technology, Tianjin, 300130, China

    Qiusheng Yang, Xue Yang, Yanji Wang, Haiou Wang & Qingyan Cheng

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  1. Qiusheng Yang
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  2. Xue Yang
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  3. Yanji Wang
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  4. Haiou Wang
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  5. Qingyan Cheng
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Correspondence to Yanji Wang.

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Yang, Q., Yang, X., Wang, Y. et al. A green route to 1,2-cyclohexanediol via the hydrolysis of cyclohexene oxide catalyzed by water. Res Chem Intermed 38, 2277–2284 (2012). https://doi.org/10.1007/s11164-012-0544-7

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