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

Chinese Journal of Chemical Engineering ›› 2012, Vol. 20 ›› Issue (2): 262-266.

• CATALYSIS, KINETICS AND REACTION ENGINEERING • 上一篇下一篇

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

收稿日期:2011-03-07 修回日期:2011-12-18 出版日期:2012-04-28 发布日期:2012-05-02
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)

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:2012-04-28 Published:2012-05-02
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)

摘要/Abstract

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

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

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.

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.

参考文献

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).

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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

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