Synthesis of Adipic Acid from Cyclohexanol by Electrochemical Oxidation Using Cr_2O_7~(2-)/Cr~(3+) as Indirect Oxidant

Authors

Zhen-hai LIANG, Institute of Clean Technique for Chemical Engineering of Taiyuan University of Technology,Taiyuan 030024,Shanxi,China;
Yu-qing CUI, Institute of Clean Technique for Chemical Engineering of Taiyuan University of Technology,Taiyuan 030024,Shanxi,China;
Hong-yan SUN, Institute of Clean Technique for Chemical Engineering of Taiyuan University of Technology,Taiyuan 030024,Shanxi,China;

Abstract

Adipic acid was synthesized by electro-oxidation of cyclohexanol taking Cr2O72-/Cr3+ as indirect oxidant.The best technological conditions were optimized by orthogonal experiment.The optimum condition are as follows: the temperature is 35℃,ratio of crude material is n(cyclohexanol)∶n(Cr2O72-)=0.4∶1 and concentration of H2SO4 is 4 mol·L-1.Under these conditions,the yield of adipic acid can reach 70.29%.Moreover,The effects of concentration of Ag2SO4,(NH4)2SO4,H2SO4and current density on the formation of Cr2O72-were also explored.The rate of Cr3+ conversion can reach 82.52%.

Keywords

indirect electro-oxidation, cyclohexanol, adipic acid, Cr2O72-/Cr3+

DOI Link

https://doi.org/10.61558/2993-074X.1860

Publication Date

2008-02-28

Online Available Date

2008-02-28

Revised Date

2008-02-28

Received Date

2008-02-28

Recommended Citation

Zhen-hai LIANG, Yu-qing CUI, Hong-yan SUN. Synthesis of Adipic Acid from Cyclohexanol by Electrochemical Oxidation Using Cr_2O_7~(2-)/Cr~(3+) as Indirect Oxidant[J]. Journal of Electrochemistry, 2008 , 14(1): 40-45.
DOI: 10.61558/2993-074X.1860
Available at: https://jelectrochem.xmu.edu.cn/journal/vol14/iss1/9

References

[1]Xu K X(徐克勋).Handbook of fine organic chemicalraw materials and intermidiates[M].Beijing:ChemicalIndustry Press,1998.260-262.
[2]Fujitani T,Nakaza M.Production of carboxylic acid:JP,63093746[P].1988.
[3]Chavan S A,Srinivas D,Ratnasamy P.Oxidation of cy-clohexane,cyclohexanone,and cyclohexanol to adipicacid by a non-HNO3route over Co/Mn cluster comple-xes[J].Journal of Catalysis,2002,212(1):39-45.
[4]Sato K,Aoki M,Noyori R.A“green”route to adipicacid:direct oxidation of cyclohexenes with 30 percenthydrogen peroxide[J].Science,1998,281(5383):1646-1647.
[5]Jiang Heng,Gong Hong,Yang Zhong-hua,et al.Cleansynthesis of adipic acid by direct oxidation of cyclohex-ene in the absence of phase transfer agents[J].Reac-tion Kinetics and Catalysis Letters,2002,75(2):315-321.
[6]Thomas Stuart M,Nagarajan Vasantha,Cheng Qiong.Biological method for the production of adipic acid andintermediates:US,6794165[P].2004.
[7]Lyalin B V,Petrosyan V A.Electrosynthesis of adipicacid by undivided cell[J].Russian Chemical Bulletin,2004,53(3):688-692.
[8]Jin Shi-xiong(金世雄),Wang Lan(王岚),Sun Feng(孙丰).Electrocatalytic effect of oxygen by anodic ev-lution Ag(Ⅰ)Co(Ⅱ)and Ni(Ⅱ)ions[J].Acta Physi-co-chemica Sinica(in Chinese),1995,11(7):654-658.
[9]Li Ke-chang(李克昌),Zhang Heng-bin(张恒彬),CaoXue-jing(曹学静),et al.Effect of different electrodematerials and addition of different metal ions on Cr3+anode oxidation[J].Chemical Journal In Chinese Uni-versities(in Chinese),2004,25(8):1533-1536.
[10]Jiang Lin-cai,Pletcher D.The catalysis of the anodicoxidation of chromium(III)to dichromate by silver(I)in the aqueous sulphuric acid[J].Journal of Electroa-nalytical Chemistry,1983,152(1~2):157-162.
[11]Schultze J W,Vetter K J.The influence of the tunnelprobability on the anodic oxygen evolution and otherredox reactions at oxide covered platinum electrodes[J].Electrochimica Acta,1973,18(11):889-896.
[12]Gu Deng-ping(顾登平),Jia Zhen-bin(贾振斌).Pro-gress on organic electrosynthesis[M].Beijing:ChinaPetrochemical Press,2001.234-235.
[13]Wang Ya-qiong(王雅琼),Zhou Tao-lin(周涛林),Xu Wen-lin(许文林).Effects of operating conditionson instantaneous current efficiency in the electrochemi-cal oxidation process of Cr3+to Cr2O72-[J].Journalof Chemical Engineering of Chinese Universities(inChinese),2005,19(6):824-828.
[14]Danilov F I,Velichenko A B.Electrocatalytic activityof anodes in reference to Cr(III)oxidation reaction[J].Electrochimica Acta,1993,38(2~3):437-440.
[15]De Souza,Claudio E,Machado Sergio AS,et al.Elec-trochemical oxidation of chromium(Ⅲ)on Pb/PbO2[J].Quim Nova,1993,16(5):426-430.
[16]Wang Lan(王岚),He Ying-sheng(何迎胜),Jin Shi-xiong(金世雄).Effect of temperature on the progressof anodic formation of Cr2O72-[J].Acta ScientiarumNaturalium Universitatis Nankaiensis(in Chinese),2000,33(3):93-95.