乙二醇催化氧化反应研究进展
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摘要
乙二醇属于最简单的二元醇,其化学性质活泼,可发生酯化、醚化、氧化、缩合、脱水等反应。针对乙二醇在近年来行情低迷,产能过剩的状况,重点论述了以乙二醇为主要原料可进行的氧化反应转化,包括化学氧化法、电化学氧化法和生物催化氧化法。详细分析了酶催化和静息细胞催化等生物法转化乙二醇合成乙醇醛、乙醇酸、乙二醛等的相关研究报道,指出了生物催化氧化法相较于传统化学氧化无可比拟的优点,并对以乙二醇为原料合成精细化学品进行了展望。
Ethylene glycol is the simplest diol.Its properties are active and can be easily esterified,etherified,oxidized,condensed,dehydrated and so on.In recent years,the production of ethylene glycol has become overcapacity and the price pressure is more serious.This paper was focused on the oxidative transformation of ethylene glycol as the main raw material,including chemical oxidation,electrochemical oxidation and biocatalytic oxidation.The research reported about the synthesis of glycolaldehyde,glycolic acid and glyoxal from ethylene glycol using biological methods such as enzyme catalysis and resting cell catalysis were also analyzed and summarized,and pointed out the advantages of biocatalytic oxidation compared to traditional chemical oxidation.Finally,prospects for the synthesis of fine chemicals from ethylene glycol are presented as well.
Ethylene glycol is the simplest diol.Its properties are active and can be easily esterified,etherified,oxidized,condensed,dehydrated and so on.In recent years,the production of ethylene glycol has become overcapacity and the price pressure is more serious.This paper was focused on the oxidative transformation of ethylene glycol as the main raw material,including chemical oxidation,electrochemical oxidation and biocatalytic oxidation.The research reported about the synthesis of glycolaldehyde,glycolic acid and glyoxal from ethylene glycol using biological methods such as enzyme catalysis and resting cell catalysis were also analyzed and summarized,and pointed out the advantages of biocatalytic oxidation compared to traditional chemical oxidation.Finally,prospects for the synthesis of fine chemicals from ethylene glycol are presented as well.
引文
[1]炎俊梁,王筠.乙二醇生产工艺流程研究进展[J].浙江化工,2018,49(1):11-12.
[2]第八届煤制乙二醇技术经济研讨会2017[EB/OL].http://expo.chemall.com.cn/zl.asp?meetid=1381.
[3]国内煤制乙二醇产业遍地开花[EB/OL].http://www.cwestc.com/newshtml/2017-4-14/455281.shtml.
[4]王家铭.山西权昇实业建设年产120万吨煤制乙二醇项目[J].四川化工,2016,19(5):15.
[5]山西20万吨煤制乙二醇工艺包合同签约[EB/OL].http://www.cnki.com.cn/Article/CJFDTotal-JXHY2016 01024.htm.
[6]山西40万t/a煤制乙二醇项目月底试车[EB/OL].http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=mtjgyzhly201606016.
[7]安学琴.煤制乙二醇生产技术现状及产业化进展[J].山西化工,2011,31(4):24-26.
[8]孙玉净,于春梅.我国煤制乙二醇产业化现状与前景[J].化学工业,2012,(1):49-52.
[9]煤制乙二醇:项目开工及投产动态[EB/OL].http://www.cnki.com.cn/Article/CJFDTotal-MHGZ201204003.htm.
[10]XIE S J,SHEN Z B,DENG J,et al.Visible light-driven C—H activation and C—C coupling of methanol into ethylene glycol[J].Nat.Commun.,2018,9:1 181.
[11]XIE S J,SHEN Z B,ZHANG H M,et al.Photocatalytic coupling of formaldehyde to ethylene glycol and glycolaldehyde over bismuth vanadate with controllable facets and cocatalysts[J].Catal.Sci.Technol.,2017,7(4):923-933.
[12]辛坤,李青松,贾冰,等.甲醛合成乙醇醛研究及其应用进展[J].天然气化工,2016,41(5):88-94.
[13]高雪莉.乙醇酸的合成工艺研究[D].天津:河北工业大学,2014.
[14]TURAN-ERTAS T,GUROL M D.Oxidation of diethylene glycol with ozone and modified Fenton processes[J].Chemosphere,2002,47(3):293-301.
[15]BERNDT H,PITSCH I,EVERT S,et al.Oxygen adsorption on Au/Al2O3,catalysts and relation to the catalytic oxidation of ethylene glycol to glycolic acid[J].Appl.Catal.A:Gen.,2003,244(1):169-179.
[16]GHAMMAMY S,KHORSANDTABAR S,MOGHIMI A,et al.Oxidation of some organic diols with trialkylammonium fluorochromates (Ⅵ),R3NH[CrO3F](R=CH3,C2H5,C3H7 and C4H9) at room temperature and under microwave condition[J].J.Mex.Chem.Soc.,2009,53(2):41-43.
[17]MEENA A K,DAIYA A,SHARMA A,et al.Oxidation of some vicinal and non-vicinal diols by tetrakis (pyridine) silver dichromate:a kinetic and mechanistic study[J].J.Indlan.Chem.Soc.,2011,88(12):1 887-1 893.
[18]MAMONTOV G V,KNYAZEV A S,PAUKSHTIS E A,et al.Adsorption and conversion of ethylene glycol on the surface of Ag-containing catalyst modified with phosphate[J].Kinet.Catal.,2013,54(6):735-743.
[19]JALALI H M.Simulation of degradation of the organic contaminants ethylene glycol and phenol by iron nanoparticles using the kinetic Monte Carlo method[J].Rsc Adv.,2014,4(62):32 928-32 933.
[20]KE Y H,QIN X X,LIU C L,et al.Oxidative esterification of ethylene glycol in methanol to form methyl glycolate over supported Au catalysts[J].Catal.Sci.Technol.,2014,4(9):3 141-3 150.
[21]MANSOOR S S,SHAFI S S.Correlation analysis of reactivity in the oxidation of some organic diols by tripropylammonium fluorochromate in non-aqueous media[J].Arab.J.Chem.,2016,9:602-609.
[22]WANG L Q,MENG H,SHEN P K,et al.In situ FT-IR spectroelectrochemical study on the mechanism of ethylene glycol electrocatalytic oxidation at a Pd electrode[J].Phys.Chem.Chem.Phys.,2011,13(7):2 667-2 673.
[23]MATSUMOTO T,SADAKIYO M,MEI L O,et al.CO2-Free power generation on an iron group nanoalloy catalyst via selective oxidation of ethylene glycol to oxalic acid in alkaline media[J].Sci.Rep.,2014,4(1):5 620.
[24]CHAUHAN N L,DAMEERA V,CHOWDHURY A,et al.Electrochemical oxidation of ethylene glycol in a channel flow reactor[J].Catal.Today,2018,309:126-132.
[25]DELEY J,KERSTERS K.Oxidation of aliphatic giycols by acetic acid bacteria[J].Bacteriol.Rev.,1964,28(28):164-180.
[26]BROWN A J.Further notes on the chemical action of Bacterium aceti[J].J.Chem.Soc.Trans.,1887,51:638-643.
[27]VISSER′T H.Biochemische onderzoekingen over het geslacht Acetobacter[D].Delft:Delft University of Technical,1925.
[28]GASTON L W,STADTMAN E R.Fermentation of ethylene glycol by Clostridium glycolicum.sp.n[J].J.Bacteriol.,1963,85(2):356-362.
[29]UWAJIMA T,AKITA H,ITO K,et al.Formation and purification of a new enzyme,glycerol oxidase and stoichiometry of the enzyme reaction[J].Agric.Bioi.Chem.,1980,44(2):399-406.
[30]WIEGANT W M,DE BONT J A M.A new route for ethylene glycol metabolism in Mycobacterium E44[J].Microbiology,1980,120(2):325-331.
[31]BORONAT A,CABALLERO E,AGUILAR J.Experimental evolution of a metabolic pathway for ethylene glycol utilization by Escherichia coli.[J].J.Bacteriol.,1983,153(1):134-139.
[32]CHILD J,WILLETTS A.Microbial metabolism of aliphatic glycols.Bacterial metabolism of ethylene glycol[J].BBA-Gen.Subjects,1978,538(2):316-327.
[33]GONZALEZ C F,TABER W A,ZELTOUN M A.Biodegradation of ethylene glycol by a salt-requiringbacterium[J].Appl.Microbiol.,1972,24(6):911-919.
[34]STOUTHAMER A H,VAN BOOM J H,BASTIAANSE A J.Metabolism of C2 compounds in Acetobacter aceti[J].Anton.Eeuw.Int.J.G.,1963,29(1):393-406.
[35]ISOBE K,NISHISE H.Enzymatic production of glyoxal from ethylene glycol using alcohol oxidase from Methanol Yeast[J].Biosci.Biotech.Biochem.,1994,58(1):170-173.
[36]ISOBE K,NISHISE H.A new enzymatic method for glycolaldehyde production from ethylene glycol[J].J.Mol.Catal.B:Enzym.,1995,1(1):37-43.
[37]UKEDA H,ISHII T,SAWAMURA M,et al.Glycolaldehyde production from ethylene glycol with immobilized alcohol oxidase and catalase[J].Biosci.Biotech.Biochem.,1998,62(8):1 589-1 591.
[38]KATAOKA M,SASAKI M,HIDALGO A R G D,et al.Glycolic acid production using ethylene glycol-oxidizing microorganisms[J].Biosci.Biotech.Biochem.,2001,65(10):2 265-2 270.
[39]NAKAMIYA K,HASHIMOTO S,ITO H,et al.Degradation of 1,4-dioxane and cyclic ethers by an isolated fungus[J].Appl.Environ.Microbiol.,2005,71(3):1 254-1 258.
[40]WEI G D,YANG X,ZHOU W,et al.Adsorptive bioconversion of ethylene glycol to glycolic acid by Gluconobacter oxydans DSM 2003[J].Biochem.Eng.J.,2009,47(1/3):127-131.
[41]MüCKSCHEL B,SIMON O,KLEBENSBERGER J,et al.Ethylene glycol metabolism by Pseudomonas putida[J].Appl.Environ.Microbiol.,2012,78(24):8 531-8 539.
[42]FRANDEN M A,JAYAKODY L,LI W J,et al.Engineering Pseudomonas putida KT2440 for efficient ethylene glycol utilization[J].Metab.Eng.,2018,48:197-207.
[43]魏胜华,孟娜,郑长龙,等.发酵法转化乙二醇制备乙醇酸[J].化工进展,2012,31(2):397-401.
[44]魏胜华,王卫军,孟娜,等.氧化葡萄糖酸杆菌静息细胞转化乙二醇制备乙醇酸[J].食品与发酵工业,2014,40(5):27-31.
[45]HUA X,CAO R,ZHOU X,et al.One-step continuous/semi-continuous whole-cell catalysis production of glycolic acid by a combining bioprocess with in-situ cell recycling and electrodialysis[J].Bioresour.Technol.,2019,273:515-520.
[46]GAO X X,MA Z F,YANG L M,et al.Enhanced bioconversion of ethylene glycol to glycolic acid by a newly isolated Burkholderia sp.EG13[J].Appl.Biochem.Biotechnol.,2014,174(4):1 572-1 580.
[47]ZHANG X X,ZHANG B Q,LIN J P,et al.Oxidation of ethylene glycol to glycolaldehyde using a highly selective alcohol dehydrogenase from Gluconobacter oxydans[J].J.Mol.Catal.B:Enzym.,2015,112:69-75.
[48]DRENT E.Process for the preparation of glycol aldehyde:US 4 414 421[P].1983-11-08.
[49]KITAGAWA S,YOKOI T,GAZETTE M.Production of glycol aldehyde:Japan 8 669 740[P].1986-04-10.
[50]HONDA T,TERADA K.Production of glycol aldehyde:Japan 8 745 548[P].1987-02-27.
[51]顾亚云,陈建华.静息细胞转化制备 6-脱氧-6-氨基(N-羟乙基)-α-L-呋喃山梨糖的研究[J].化学与生物工程,2013,30(7):47-50.
[2]第八届煤制乙二醇技术经济研讨会2017[EB/OL].http://expo.chemall.com.cn/zl.asp?meetid=1381.
[3]国内煤制乙二醇产业遍地开花[EB/OL].http://www.cwestc.com/newshtml/2017-4-14/455281.shtml.
[4]王家铭.山西权昇实业建设年产120万吨煤制乙二醇项目[J].四川化工,2016,19(5):15.
[5]山西20万吨煤制乙二醇工艺包合同签约[EB/OL].http://www.cnki.com.cn/Article/CJFDTotal-JXHY2016 01024.htm.
[6]山西40万t/a煤制乙二醇项目月底试车[EB/OL].http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=mtjgyzhly201606016.
[7]安学琴.煤制乙二醇生产技术现状及产业化进展[J].山西化工,2011,31(4):24-26.
[8]孙玉净,于春梅.我国煤制乙二醇产业化现状与前景[J].化学工业,2012,(1):49-52.
[9]煤制乙二醇:项目开工及投产动态[EB/OL].http://www.cnki.com.cn/Article/CJFDTotal-MHGZ201204003.htm.
[10]XIE S J,SHEN Z B,DENG J,et al.Visible light-driven C—H activation and C—C coupling of methanol into ethylene glycol[J].Nat.Commun.,2018,9:1 181.
[11]XIE S J,SHEN Z B,ZHANG H M,et al.Photocatalytic coupling of formaldehyde to ethylene glycol and glycolaldehyde over bismuth vanadate with controllable facets and cocatalysts[J].Catal.Sci.Technol.,2017,7(4):923-933.
[12]辛坤,李青松,贾冰,等.甲醛合成乙醇醛研究及其应用进展[J].天然气化工,2016,41(5):88-94.
[13]高雪莉.乙醇酸的合成工艺研究[D].天津:河北工业大学,2014.
[14]TURAN-ERTAS T,GUROL M D.Oxidation of diethylene glycol with ozone and modified Fenton processes[J].Chemosphere,2002,47(3):293-301.
[15]BERNDT H,PITSCH I,EVERT S,et al.Oxygen adsorption on Au/Al2O3,catalysts and relation to the catalytic oxidation of ethylene glycol to glycolic acid[J].Appl.Catal.A:Gen.,2003,244(1):169-179.
[16]GHAMMAMY S,KHORSANDTABAR S,MOGHIMI A,et al.Oxidation of some organic diols with trialkylammonium fluorochromates (Ⅵ),R3NH[CrO3F](R=CH3,C2H5,C3H7 and C4H9) at room temperature and under microwave condition[J].J.Mex.Chem.Soc.,2009,53(2):41-43.
[17]MEENA A K,DAIYA A,SHARMA A,et al.Oxidation of some vicinal and non-vicinal diols by tetrakis (pyridine) silver dichromate:a kinetic and mechanistic study[J].J.Indlan.Chem.Soc.,2011,88(12):1 887-1 893.
[18]MAMONTOV G V,KNYAZEV A S,PAUKSHTIS E A,et al.Adsorption and conversion of ethylene glycol on the surface of Ag-containing catalyst modified with phosphate[J].Kinet.Catal.,2013,54(6):735-743.
[19]JALALI H M.Simulation of degradation of the organic contaminants ethylene glycol and phenol by iron nanoparticles using the kinetic Monte Carlo method[J].Rsc Adv.,2014,4(62):32 928-32 933.
[20]KE Y H,QIN X X,LIU C L,et al.Oxidative esterification of ethylene glycol in methanol to form methyl glycolate over supported Au catalysts[J].Catal.Sci.Technol.,2014,4(9):3 141-3 150.
[21]MANSOOR S S,SHAFI S S.Correlation analysis of reactivity in the oxidation of some organic diols by tripropylammonium fluorochromate in non-aqueous media[J].Arab.J.Chem.,2016,9:602-609.
[22]WANG L Q,MENG H,SHEN P K,et al.In situ FT-IR spectroelectrochemical study on the mechanism of ethylene glycol electrocatalytic oxidation at a Pd electrode[J].Phys.Chem.Chem.Phys.,2011,13(7):2 667-2 673.
[23]MATSUMOTO T,SADAKIYO M,MEI L O,et al.CO2-Free power generation on an iron group nanoalloy catalyst via selective oxidation of ethylene glycol to oxalic acid in alkaline media[J].Sci.Rep.,2014,4(1):5 620.
[24]CHAUHAN N L,DAMEERA V,CHOWDHURY A,et al.Electrochemical oxidation of ethylene glycol in a channel flow reactor[J].Catal.Today,2018,309:126-132.
[25]DELEY J,KERSTERS K.Oxidation of aliphatic giycols by acetic acid bacteria[J].Bacteriol.Rev.,1964,28(28):164-180.
[26]BROWN A J.Further notes on the chemical action of Bacterium aceti[J].J.Chem.Soc.Trans.,1887,51:638-643.
[27]VISSER′T H.Biochemische onderzoekingen over het geslacht Acetobacter[D].Delft:Delft University of Technical,1925.
[28]GASTON L W,STADTMAN E R.Fermentation of ethylene glycol by Clostridium glycolicum.sp.n[J].J.Bacteriol.,1963,85(2):356-362.
[29]UWAJIMA T,AKITA H,ITO K,et al.Formation and purification of a new enzyme,glycerol oxidase and stoichiometry of the enzyme reaction[J].Agric.Bioi.Chem.,1980,44(2):399-406.
[30]WIEGANT W M,DE BONT J A M.A new route for ethylene glycol metabolism in Mycobacterium E44[J].Microbiology,1980,120(2):325-331.
[31]BORONAT A,CABALLERO E,AGUILAR J.Experimental evolution of a metabolic pathway for ethylene glycol utilization by Escherichia coli.[J].J.Bacteriol.,1983,153(1):134-139.
[32]CHILD J,WILLETTS A.Microbial metabolism of aliphatic glycols.Bacterial metabolism of ethylene glycol[J].BBA-Gen.Subjects,1978,538(2):316-327.
[33]GONZALEZ C F,TABER W A,ZELTOUN M A.Biodegradation of ethylene glycol by a salt-requiringbacterium[J].Appl.Microbiol.,1972,24(6):911-919.
[34]STOUTHAMER A H,VAN BOOM J H,BASTIAANSE A J.Metabolism of C2 compounds in Acetobacter aceti[J].Anton.Eeuw.Int.J.G.,1963,29(1):393-406.
[35]ISOBE K,NISHISE H.Enzymatic production of glyoxal from ethylene glycol using alcohol oxidase from Methanol Yeast[J].Biosci.Biotech.Biochem.,1994,58(1):170-173.
[36]ISOBE K,NISHISE H.A new enzymatic method for glycolaldehyde production from ethylene glycol[J].J.Mol.Catal.B:Enzym.,1995,1(1):37-43.
[37]UKEDA H,ISHII T,SAWAMURA M,et al.Glycolaldehyde production from ethylene glycol with immobilized alcohol oxidase and catalase[J].Biosci.Biotech.Biochem.,1998,62(8):1 589-1 591.
[38]KATAOKA M,SASAKI M,HIDALGO A R G D,et al.Glycolic acid production using ethylene glycol-oxidizing microorganisms[J].Biosci.Biotech.Biochem.,2001,65(10):2 265-2 270.
[39]NAKAMIYA K,HASHIMOTO S,ITO H,et al.Degradation of 1,4-dioxane and cyclic ethers by an isolated fungus[J].Appl.Environ.Microbiol.,2005,71(3):1 254-1 258.
[40]WEI G D,YANG X,ZHOU W,et al.Adsorptive bioconversion of ethylene glycol to glycolic acid by Gluconobacter oxydans DSM 2003[J].Biochem.Eng.J.,2009,47(1/3):127-131.
[41]MüCKSCHEL B,SIMON O,KLEBENSBERGER J,et al.Ethylene glycol metabolism by Pseudomonas putida[J].Appl.Environ.Microbiol.,2012,78(24):8 531-8 539.
[42]FRANDEN M A,JAYAKODY L,LI W J,et al.Engineering Pseudomonas putida KT2440 for efficient ethylene glycol utilization[J].Metab.Eng.,2018,48:197-207.
[43]魏胜华,孟娜,郑长龙,等.发酵法转化乙二醇制备乙醇酸[J].化工进展,2012,31(2):397-401.
[44]魏胜华,王卫军,孟娜,等.氧化葡萄糖酸杆菌静息细胞转化乙二醇制备乙醇酸[J].食品与发酵工业,2014,40(5):27-31.
[45]HUA X,CAO R,ZHOU X,et al.One-step continuous/semi-continuous whole-cell catalysis production of glycolic acid by a combining bioprocess with in-situ cell recycling and electrodialysis[J].Bioresour.Technol.,2019,273:515-520.
[46]GAO X X,MA Z F,YANG L M,et al.Enhanced bioconversion of ethylene glycol to glycolic acid by a newly isolated Burkholderia sp.EG13[J].Appl.Biochem.Biotechnol.,2014,174(4):1 572-1 580.
[47]ZHANG X X,ZHANG B Q,LIN J P,et al.Oxidation of ethylene glycol to glycolaldehyde using a highly selective alcohol dehydrogenase from Gluconobacter oxydans[J].J.Mol.Catal.B:Enzym.,2015,112:69-75.
[48]DRENT E.Process for the preparation of glycol aldehyde:US 4 414 421[P].1983-11-08.
[49]KITAGAWA S,YOKOI T,GAZETTE M.Production of glycol aldehyde:Japan 8 669 740[P].1986-04-10.
[50]HONDA T,TERADA K.Production of glycol aldehyde:Japan 8 745 548[P].1987-02-27.
[51]顾亚云,陈建华.静息细胞转化制备 6-脱氧-6-氨基(N-羟乙基)-α-L-呋喃山梨糖的研究[J].化学与生物工程,2013,30(7):47-50.