Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

doi:10.1016/j.cjche.2020.04.013

Chinese Journal of Chemical Engineering ›› 2020, Vol. 28 ›› Issue (10): 2542-2548.DOI: 10.1016/j.cjche.2020.04.013

• Catalysis, Kinetics and Reaction Engineering • Previous Articles Next Articles

Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

Wenjuan Yan¹, Wenxiang Zhang¹, Qi Xia¹, Shuaishuai Wang¹, Shuxia Zhang¹, Jian Shen², Xin Jin¹

1 State Key Laboratory of Heavy Oil Processing, Center for Chemical Engineering Experimental Teaching, China University of Petroleum, Qingdao 266580, China;
2 College of Environment and Resources, Xiangtan University, Xiangtan 411105, China

Received:2019-12-10 Revised:2020-04-11 Online:2020-12-03 Published:2020-10-28
Contact: Xin Jin
Supported by:
This work was supported by the National Natural Science Foundation (21706290), Natural Science Foundation of Shandong Province (ZR2017MB004, ZR2017BB007), Postdoctoral Research Funding of Shandong Province (201703016), Fundamental Research Funding of Qingdao (17-1-1-67-jch, 17-1-1-80-jch), Qingdao Postdoctoral Research Funding (BY20170210), “the Fundamental Research Funds for the Central Universities” (18CX02145A, 17CX02017A), new faculty start-up funding from China University of Petroleum (YJ201601058) and China Postdoctoral Science Foundation (2017M612374).

Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

Wenjuan Yan¹, Wenxiang Zhang¹, Qi Xia¹, Shuaishuai Wang¹, Shuxia Zhang¹, Jian Shen², Xin Jin¹

1 State Key Laboratory of Heavy Oil Processing, Center for Chemical Engineering Experimental Teaching, China University of Petroleum, Qingdao 266580, China;
2 College of Environment and Resources, Xiangtan University, Xiangtan 411105, China

通讯作者: Xin Jin
基金资助:
This work was supported by the National Natural Science Foundation (21706290), Natural Science Foundation of Shandong Province (ZR2017MB004, ZR2017BB007), Postdoctoral Research Funding of Shandong Province (201703016), Fundamental Research Funding of Qingdao (17-1-1-67-jch, 17-1-1-80-jch), Qingdao Postdoctoral Research Funding (BY20170210), “the Fundamental Research Funds for the Central Universities” (18CX02145A, 17CX02017A), new faculty start-up funding from China University of Petroleum (YJ201601058) and China Postdoctoral Science Foundation (2017M612374).

Abstract

Abstract: Adipic acid is a dicarboxylic acid of great industrial importance, mainly used in the production of nylon-6,6 and polyurethane. The use of nitric acid as an oxidant in the industrial production of adipic acid poses significant carbon footprint to the environment. Clean adipic acid synthesis methods using a heterogeneous catalyst with H₂O₂ as oxidant and water as solvent have potential advantages of low catalyst cost, easy synthesis and recovery, cleanness and environmental protection. In this work, hexagonal mesoporous silicate materials were synthesized by a sol-gel method and evaluated for cyclohexanol/cyclohexanone oxidation to adipic acid. The physical and chemical properties of Fe-HMS were characterized by XRD, HR-TEM, BET and UV-Vis. The experimental results showed that Fe-HMS materials show pore sizes ranging from 2-3 nm. W- and Mo-based polyoxometalates were also evaluated and compared to the Fe-based HMS catalysts. To improve the adipic acid yield, the influence of the transition metal as well as the effect of metal loading, reaction temperature and catalyst amount on the catalytic performances of Fe-HMS have been investigated in details. When Si/Fe atomic ratio = 100, Fe-HMS catalyst shows the highest activity, with a cyclohexanone conversion of 92.3% and adipic acid selectivity of 29.4%. The reaction pathway of cyclohexanone oxidation was further proposed based on experimental data.

Key words: Oxidation, Adipic acid, Hexagonal mesoporous silicates, hydrogen peroxide

摘要： Adipic acid is a dicarboxylic acid of great industrial importance, mainly used in the production of nylon-6,6 and polyurethane. The use of nitric acid as an oxidant in the industrial production of adipic acid poses significant carbon footprint to the environment. Clean adipic acid synthesis methods using a heterogeneous catalyst with H₂O₂ as oxidant and water as solvent have potential advantages of low catalyst cost, easy synthesis and recovery, cleanness and environmental protection. In this work, hexagonal mesoporous silicate materials were synthesized by a sol-gel method and evaluated for cyclohexanol/cyclohexanone oxidation to adipic acid. The physical and chemical properties of Fe-HMS were characterized by XRD, HR-TEM, BET and UV-Vis. The experimental results showed that Fe-HMS materials show pore sizes ranging from 2-3 nm. W- and Mo-based polyoxometalates were also evaluated and compared to the Fe-based HMS catalysts. To improve the adipic acid yield, the influence of the transition metal as well as the effect of metal loading, reaction temperature and catalyst amount on the catalytic performances of Fe-HMS have been investigated in details. When Si/Fe atomic ratio = 100, Fe-HMS catalyst shows the highest activity, with a cyclohexanone conversion of 92.3% and adipic acid selectivity of 29.4%. The reaction pathway of cyclohexanone oxidation was further proposed based on experimental data.

关键词: Oxidation, Adipic acid, Hexagonal mesoporous silicates, hydrogen peroxide

Wenjuan Yan, Wenxiang Zhang, Qi Xia, Shuaishuai Wang, Shuxia Zhang, Jian Shen, Xin Jin. Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid[J]. Chinese Journal of Chemical Engineering, 2020, 28(10): 2542-2548.

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Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

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