Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen

Chin.J.Chem.Eng. ›› 2012, Vol. 20 ›› Issue (2): 262-266.

Previous Articles Next Articles

Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen

SHE Yuanbin, WANG Weijie, LI Guojun

Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100124, China

Received:2011-03-07 Revised:2011-12-18 Online:2012-05-02 Published:2012-04-28
Supported by:
Supported by the Key Project of National Natural Science Foundation of China (21036009, 20776003);the Key Project of Natural Science Foundation of Beijing (2061001);the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of the Beijing Municipality (PHR 200907105, PHR 201107104)

Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen

佘远斌, 王维洁, 李国君

Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100124, China

通讯作者: SHE Yuanbin
基金资助:
Supported by the Key Project of National Natural Science Foundation of China (21036009, 20776003);the Key Project of Natural Science Foundation of Beijing (2061001);the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of the Beijing Municipality (PHR 200907105, PHR 201107104)

Abstract

Abstract: The two novel green oxidation processes of p/o-cresols to p/o-hydroxybenzaldehydes catalyzed by metalloporphyrins in the presence of molecular oxygen were developed in this work.Among the metalloporphyrins with different central ions and substituents studied,T(p-NO₂)PPCoCl and T(p-OCH₃)PPFeCl presented the highest activities for p-cresol and o-cresol oxidation reactions respectively.The molar ratio of sodium hydroxide to cresols and different reaction parameters including reaction temperature,reaction time and reaction pressure have been investigated,and 69.8%/50.4% conversions of p/o-cresol and 86.6%/26.6% selectivities for p/o-hydroxybenzaldehydes were reached under optimized conditions.

Key words: metalloporphyrin, p/o-cresol, p/o-hydroxybenzaldehyde, biomimetic catalytic oxidation, oxygen

摘要： The two novel green oxidation processes of p/o-cresols to p/o-hydroxybenzaldehydes catalyzed by metalloporphyrins in the presence of molecular oxygen were developed in this work.Among the metalloporphyrins with different central ions and substituents studied,T(p-NO₂)PPCoCl and T(p-OCH₃)PPFeCl presented the highest activities for p-cresol and o-cresol oxidation reactions respectively.The molar ratio of sodium hydroxide to cresols and different reaction parameters including reaction temperature,reaction time and reaction pressure have been investigated,and 69.8%/50.4% conversions of p/o-cresol and 86.6%/26.6% selectivities for p/o-hydroxybenzaldehydes were reached under optimized conditions.

关键词: metalloporphyrin, p/o-cresol, p/o-hydroxybenzaldehyde, biomimetic catalytic oxidation, oxygen

SHE Yuanbin, WANG Weijie, LI Guojun. Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen[J]. Chin.J.Chem.Eng., 2012, 20(2): 262-266.

佘远斌, 王维洁, 李国君. Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen[J]. Chinese Journal of Chemical Engineering, 2012, 20(2): 262-266.

References

1 Smith,W.E.,(Dow Chemical Corporation),“Reimer-Tiemann aldehyde synthesis process”,US Pat.,4324922(1982).
2 Thoer,A.,Denis,G.,“The Reimer-Tiemann reaction in slightly hydrated solid-liquid medium:A new method for the synthesis of formyl and diformyl phenols”,Synth.Commun.,18,2095-2101(1988).
3 Neumann,R.,Sasson,Y.,“Increased para selectivity in the Reimer-Tiemann reaction by use of polyethylene glycol as complexing agent”,Synthesis,7,569-571(1986).
4 Sparfel,D.,Baranne-Lafont,J.,Nguyen,K.C.,Capdevielle,P., Maumy,M.,“Catalytic-oxidation of 2-hydroxymethyl phenols by MⁿCl_n/M⁰/O₂(M=Cu,Fe)”,Tetrahedron,46,793-802(1990).
5 Formanek,K.,“o-Hydroxybenzaldehydes”,Eur.Pat.,EP 77279 A1 (1983).
6 Qiao,Y.H.,Teng,J.J.,“The synthesis of o-hydroxybenzaldehyde by oxidating o-cresol with oxygen”,Mao Ming Xue Bao,15,26-29 (2005).(in Chinese)
7 She,Y.B.,Wang,L.Z.,Song,X.F.,Zhang,Y.H.,Chen,Y.X.,“Synthesis and QSAR of metal porphyrin biomimetic catalysts and their application in oxidation of hydrocarbons”,Fine Chemicals,22,401-408(2005).(in Chinese)
8 Poltowicz,J.,Haber,J.,“The oxyfunctionalization of cycloalkanes with dioxygen catalyzed by soluble and supported metalloporphyrins”,J.Mol.Catal.,220,43-51(2004).
9 Meunier,B.,“Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage”,Chem.Rev.,92(6),1411-1456(1992).
10 Groves,J.T.,Bonchio,M.,Carofiglio,T.,Shalyaev,K.,“Rapid catalytic oxygenation of hydrocarbons by ruthenium pentafluorophenylporphyrin complexes:Evidence for the involvement of a Ru(III)intermediate”,J.Am.Chem.Soc.,118,8961-8963(1996).
11 She,Y.B.,Fan,L.L.,Zhang,Y.H.,Song,X.F.,“Novel technology for green synthesis of p-nitrobenzaldehyde with metalloporphyrins as biomimetic catalysts”,J.Chem.Ind.Eng.(China),55(12),2032-2037(2004).(in Chinese)
12 Wang,L.Z.,She,Y.B.,Zhong,R.G.,Ji,H.B.,Zhang,Y.H.,Song,X.F., “A green process for oxidation of p-nitrotoluene catalyzed by metalloporphyrins under mild conditions”,Org.Process Res.Dev.,10(4),757-761(2006).
13 Bottomley,L.A.,Kadish,K.M.,“Counterion and solvent effects on the electrode-reactions of iron porphyrins”,Inorg.Chem.,20(5),1348-1357(1981).
14 Liu,Y.M.,Liu,S.T.,Zhu,K.Z,Ye,X.K.,Wu,Y.,“Catalysis of hydrotalcite-like compounds in liquid phase oxidation:(II)Oxidation of p-cresol to p-hydroxybenzaldehyde”,Appl.Catal.A Gen.,169,127-135(1998).

[1]	Bin Lin, Wenyao Chen, Nan Song, Zhihua Zhang, Qianhong Wang, Wei Du, Xinggui Zhou, Xuezhi Duan. Mechanistic insights into propylene oxidation to acrolein over gold catalysts [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 39-49.
[2]	Xinyu Yang, Zezhi Chen, Huijuan Gong. Coking of Pt/γ-Al₂O₃ catalyst in landfill gas deoxygen and its effects on catalytic performance [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 224-232.
[3]	Libing Yu, Qiuyan Huang, Jing Wu, Erhong Song, Beibei Xiao. Spatial-five coordination promotes the high efficiency of CoN₄ moiety in graphene-based bilayer for oxygen reduction electrocatalysis: A density functional theory study [J]. Chinese Journal of Chemical Engineering, 2023, 54(2): 106-113.
[4]	Xueqing Chen, Weiqun Gao, Yan Sun, Xiaoyan Dong. Multiple effects of polydopamine nanoparticles on Cu²⁺-mediated Alzheimer's β-amyloid aggregation [J]. Chinese Journal of Chemical Engineering, 2023, 54(2): 144-152.
[5]	Wenjuan Yan, Puhua Sun, Chen Luo, Xingfan Xia, Zhifei Liu, Yuming Zhao, Shuxia Zhang, Liang Sun, Feng Du. PtCo-based nanocatalyst for oxygen reduction reaction: Recent highlights on synthesis strategy and catalytic mechanism [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 101-123.
[6]	Xinhai Zhou, Dawei Zhou, Xinhui Bao, Yang Zhang, Jie Zhou, Fengxue Xin, Wenming Zhang, Xiujuan Qian, Weiliang Dong, Min Jiang, Katrin Ochsenreither. Production of palmitoleic acid by oleaginous yeast Scheffersomyces segobiensis DSM 27193 using systematic dissolved oxygen regulation strategy [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 324-331.
[7]	Hongbo Song, Wei Wang, Jiachen Sun, Xianhui Wang, Xianhua Zhang, Sai Chen, Chunlei Pei, Zhi-Jian Zhao. Chemical looping oxidative propane dehydrogenation controlled by oxygen bulk diffusion over FeVO₄ oxygen carrier pellets [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 409-420.
[8]	Ting He, Songhong Yu, Jinhui He, Dejian Chen, Jie Li, Hongjun Hu, Xingrui Zhong, Yawei Wang, Zhaohui Wang, Zhaoliang Cui. Membranes for extracorporeal membrane oxygenator (ECMO): History, preparation, modification and mass transfer [J]. Chinese Journal of Chemical Engineering, 2022, 49(9): 46-75.
[9]	Juan Xu, Ping Zhu, Islam H. El Azab, Ben Bin Xu, Zhanhu Guo, Ashraf Y. Elnaggar, Gaber A.M. Mersal, Xiangyi Liu, Yunfei Zhi, Zhiping Lin, Hassan Algadi, Shaoyun Shan. An efficient bifunctional Ni-Nb₂O₅ nanocatalysts for the hydrodeoxygenation of anisole [J]. Chinese Journal of Chemical Engineering, 2022, 49(9): 187-197.
[10]	Wei Hong, Xinran Shen, Jian Wang, Xin Feng, Wenjing Zhang, Jing Li, Zidong Wei. High-loading Pt-alloy catalysts for boosted oxygen reduction reaction performance [J]. Chinese Journal of Chemical Engineering, 2022, 48(8): 30-35.
[11]	Xian-Tai Zhou, Ling-Ling Wang, Yang Li, Hong-Bing Ji. Liquid-phase epoxidation of propylene with molecular oxygen by chloride manganese meso-tetraphenylporphyrins [J]. Chinese Journal of Chemical Engineering, 2022, 48(8): 61-65.
[12]	Zhouxin Chang, Feng Yu, Zhisong Liu, Zijun Wang, Jiangbing Li, Bin Dai, Jinli Zhang. Ni-Al mixed metal oxide with rich oxygen vacancies: CO methanation performance and density functional theory study [J]. Chinese Journal of Chemical Engineering, 2022, 46(6): 73-83.
[13]	Wei Zhou, Xiaoxiao Meng, Liang Xie, Junfeng Li, Yani Ding, Yanlin Su, Jihui Gao, Guangbo Zhao. Simultaneous utilization of electro-generated O₂ and H₂ for H₂O₂ production: An upgrade of the Pd-catalytic electro-Fenton process for pollutants degradation [J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 363-368.
[14]	Baowen Wang, Zhongyuan Cai, Heyu Li, Yanchen Liang, Tao Jiang, Ning Ding, Haibo Zhao. Reaction characteristics investigation of CeO₂-enhanced CaSO₄ oxygen carrier with lignite [J]. Chinese Journal of Chemical Engineering, 2022, 42(2): 319-328.
[15]	Shusheng Li, Rui Kuang, Xiangzheng Kong, Xiaoli Zhu, Xubao Jiang. Immobilization of cobalt oxide nanoparticles on porous nitrogen-doped carbon as electrocatalyst for oxygen evolution [J]. Chinese Journal of Chemical Engineering, 2022, 52(12): 10-18.

Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen

Oxidation of p/o-Cresols to p/o-Hydroxybenzaldehydes Catalyzed by Metalloporphyrins with Molecular Oxygen

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments