Thermodynamic analysis of o-hydroxytoluene catalytic oxidation to prepare o-hydroxybenzaldehyde

doi:10.3969/j.issn.0438-1157.2013.10.005

CIESC Journal ›› 2013, Vol. 64 ›› Issue (10): 3520-3526.DOI: 10.3969/j.issn.0438-1157.2013.10.005

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Thermodynamic analysis of o-hydroxytoluene catalytic oxidation to prepare o-hydroxybenzaldehyde

WANG Weijie¹, SHE Yuanbin^1,2, FENG Yingqi¹, YANG Liu¹

1. Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100124, China;
2. Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission & Ministry of Education, South-Central University for Nationalities, Wuhan 430074, Hubei, China

Received:2013-03-25 Revised:2013-05-26 Online:2013-10-05 Published:2013-10-05
Supported by:
supported by the National Natural Science Foundation of China(21036009,21276006,21076004)and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality(PHR201107104).

催化氧化邻羟基甲苯制备邻羟基苯甲醛的热力学分析

王维洁¹, 佘远斌^1,2, 冯瑛琪¹, 杨柳¹

1. 北京工业大学绿色化学与精细化工研究所, 北京 100124;
2. 中南民族大学化学与材料科学学院催化材料科学国家民委-教育部共建暨湖北省重点实验室, 湖北武汉 430074

通讯作者: 佘远斌
作者简介:王维洁(1983-),女,博士研究生。
基金资助:
国家自然科学基金项目(21036009,21276006,21076004);北京市人才强教绿色化工创新团队计划项目(PHR201107104)

Abstract

Abstract: Catalytic oxidation of o-hydroxytoluene(ONT)is the main process to synthesize o-hydroxybenzaldehyde(OHBA),but the key problem is how to improve selectivity and yield of target product.In order to make more effective use of resources,the thermodynamic properties of o-hydroxytoluene oxidation were analyzed.The basic thermodynamic data of the reaction products were estimated through several group-contribution methods.According to the basic thermodynamic principles,the relationships between reaction temperature and reaction enthalpy change,reaction Gibbs free energy change,and reaction equilibrium constant were established.The calculation results were as follows:R₁:Δ_rH₂₉₈^Θ＝-158.36 kJ·mol^-1,Δ_rG₂₉₈^Θ＝-170.93 kJ·mol^-1; R₂:Δ_rH₂₉₈^Θ＝-214.53 kJ·mol^-1,Δ_rG₂₉₈^Θ＝-163.56 kJ·mol^-1; R₃,Δ_rH₂₉₈^Θ＝-259.35 kJ·mol^-1,Δ_rG₂₉₈^Θ＝-260.27 kJ·mol^-1.In the researched reaction temperature range,all the reaction steps were exothermic reactions and could proceed spontaneously,and a higher reaction temperature went against the reaction procedure.The thermodynamic analysis results provided the basic data for research on improving selectivity of target product,and could guide optimizing reaction conditions and commercialization.

Key words: o-hydroxytoluene, o-hydroxybenzaldehyde, catalytic oxidation;group-contribution method, thermodynamics

关键词: 邻羟基甲苯, 邻羟基苯甲醛, 催化氧化, 基团贡献法, 热力学

CLC Number:

O642.4

WANG Weijie, SHE Yuanbin, FENG Yingqi, YANG Liu. Thermodynamic analysis of o-hydroxytoluene catalytic oxidation to prepare o-hydroxybenzaldehyde[J]. CIESC Journal, 2013, 64(10): 3520-3526.

王维洁, 佘远斌, 冯瑛琪, 杨柳. 催化氧化邻羟基甲苯制备邻羟基苯甲醛的热力学分析[J]. 化工学报, 2013, 64(10): 3520-3526.

References 21

[1]	Jahnke K,Podschune B.Acid-base catalytic mechanism of dihydropyrimidinase from pH studies[J].Biochemistry,1993,32:5160-5165
[2]	Liu Cuiying(柳翠英),Ge Weiying(葛蔚颖),Qian Jun(钱俊),Li Zhong(李忠),Yu Aihua(于爱华).Synthesis and biological activity studies of halogenated salicylaldehyde N4-thiosemicarbazone derivatives[J].Chemical Reagents(化学试剂),2003,25(3):160-162
[3]	Mazza M,Montanari L,Pavanetto F.Phytotoxicity of hydrazones of aromatic aldehydes[J].Farmaco-edizione Scientifica,1976,31(5):334-344
[4]	Jiang Senming(江森明),Gong Qisun(龚启孙),Yao Wei(姚巍),Peng Weili(彭伟立).Study on the synthesis of the herbicide of pyrimidinyloxybenzylamine derivatives[J].Zhejiang Chemical Industry(浙江化工),2005,36(10):11-15
[5]	Dang Yuanlin(党元林),Bao Xiaoyu(包晓玉),Zhu Xinde(祝心德),Wang Chenggang(王成刚).Synthesis,characterization and antifungal activity of salicylaldehyde O,O-dimethyl phosphoramidothioic and their complexes of Cu(Ⅱ),Ni(Ⅱ)and Zn(Ⅱ)[J].Chemical Research and Application(化学研究与应用),2002,14(4):430-432
[6]	Popescu F.Zinc electroplating baths[P]:US,3778359. 1973
[7]	Yao Hongliang(姚宏亮),Li Fangshi(李方实).Applications and synthesis of salicylaldehyde[J].Jiangsu Chemical Industry(江苏化工),2007,35(3):17-19
[8]	Schnatterer A,Fiege H,Neumann K H.Method for the production of o-hydroxy benzaldehyde[P]:EP,451650.1991-10-01
[9]	Karel F.o-Hydroxybenzaldehydes[P]:JP,58072536. 1983
[10]	Wang F,Xu J,Liao S J.One-step heterogeneously catalytic oxidation of o-cresol by oxygen to salicylaldehyde[J].Chemical Communication,2002,6:626-627
[11]	Wang Feng(王峰),Xu Jie(徐杰).Catalyst for directly selective oxidation of o-cresol[P]:CN,1475307A.2004-02-18
[12]	Qiao Yanhui(乔艳辉),Teng Junjiang(滕俊江).The synthesis of o-hydroxybenzaldehyde by oxidating o-cresol with oxygen[J].Journal of Guandong College Petrochemical Technology(茂名学院学报),2005,15(4):26-29
[13]	Hou Chaopeng(侯朝鹏),Xia Guofu(夏国富),Li Mingfeng(李明丰),Nie Hong(聂红),Li Dadong(李大东).Thermodynamics of hydrogen sulfide poisoning and feasibility of sulfur tolerance on F-T synthesis catalyst[J].CIESC Journal(化工学报),2011,62(3):598-603
[14]	She Y B,Wang W J,Li G J.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
[15]	Yaws C L.Chemical Properties Handbook [M].New York:McGraw-Hill,1999
[16]	Poling B E,Prausntz J M,O' Connell J P.The Properties of Gases and Liquids [M].5th ed.New York:McGraw-Hill,2000
[17]	Zhang Jilon(张继龙),Zhao Zhitong(赵志仝),Qiao Yan(乔燕),Lin Hao(林昊),Pang Xianyong(庞先勇),Bai Qirong(白启荣),Li Ruifeng(李瑞丰).Thermodynamic analysis on preparation of methyl oleate via transesterification by group-contribution method[J].CIESC Journal(化工学报),2012,63(6):1684-1690
[18]	Wang Linlin(王琳琳),Chen Jianyun(陈建云),Liang Jiezhen(梁杰珍),Chen Xiaopeng(陈小鹏),Chen Yuanping(陈远萍),Tang Kaiwei(唐开韦).Thermodynamic analysis for esterification of abietic acid with methanol by group-contribution method[J].CIESC Journal(化工学报),2013,64(6):1900-1906
[19]	Zhao Guoliang(赵国良),Jin Changde(靳长德).Thermodynamic Data of Estimate Organic(有机物热力学数据的估算)[M].Beijing:Higher Education Press,1983
[20]	Physical Chemistry Department of the Tianjin University. Physical Chemistry(物理化学)[M].Beijing:Higher Education Press,2005
[21]	Wang Chenye(王晨晔),Li Huiquan(李会泉),Cao Yan(曹妍),Liu Haitao(柳海涛),Hou Xinjuan(侯新娟),Zhang Yi(张懿).Thermodynamic analysis on synthesis of 4,4-methylenedianiline by reaction of aniline and formaldehyde[J].CIESC Journal(化工学报),2012,63(8):2348-2355

Thermodynamic analysis of o-hydroxytoluene catalytic oxidation to prepare o-hydroxybenzaldehyde

催化氧化邻羟基甲苯制备邻羟基苯甲醛的热力学分析

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