The oxidation of para-xylene to terephthalic acid has been commercialised as the AMOCO process (Co/Mn/Br) that uses a homogeneous catalyst of cobalt and manganese together with a corrosive bromide compound as a promoter. This process is conducted in acidic medium at a high tempera-ture (175-225 °C). Concerns over environmental and safety issues have driven studies to find mild-er oxidation reactions of para-xylene. This review discussed past and current progress in the oxida-tion of para-xylene process. The discussion concentrates on the approach of green chemistry in-cluding (1) using heterogeneous catalysts with promising high selectivity and mild reaction condi-tion, (2) application of carbon dioxide as a co-oxidant, and (3) application of alternative promoters. The optimisation of para-xylene oxidation was also outlined.
参考文献
[1] | Li M;Niu F;Zuo X;Metelski P D Busch D H Subramaniam B .[J].Chemical engineering science,2013,104:93. |
[2] | Partenheimer W .[J].Catalysis Today,1995,23:69. |
[3] | Wang L J;Cheng Y W;Wang Q B;Li X .[J].Front Chem Eng China,2007,1:317. |
[4] | Giacomo C;Silber P .[J].Ber Deutsch Chem Ges,1912,45:38. |
[5] | Xiao Y;Zhang X Y;Wang Q B;Tan Z Guo C C Deng W Liu Z G Zhang H F .[J].Chinese Chemical Letters,2011,22:135. |
[6] | Stephens H N .[J].Journal of the American Chemical Society,1926,48:2920. |
[7] | Scheirs J;Long T E.Modern Polyesters:Chemistry and Technology of Polyesters and Copolyesters[M].Chichester:John Wiley and Sons,2013:67. |
[8] | Raghavendrachar P;Ramachandran S .[J].Industrial and Engineering Chemistry Research,1992,31:453. |
[9] | Saffer A;Barker R S .[P].GB Patent 807091,1959. |
[10] | Whinfield J R;Dickson J T .[P].GB Patent 578079,1946. |
[11] | Saffer A;Barker R S .[P].US Patent 2833816,1958. |
[12] | Saffer A;Barker R S .[P].US Patent 3089906,1963. |
[13] | Landau R;Saffer A .[J].Chemical Engineering Progress,1968,64:20. |
[14] | Ghiaci M;Mostajeran M;Gil A .[J].Industrial and Engineering Chemistry Research,2012,51:15821. |
[15] | Tomás, R.A.F.;Bordado, J.C.M.;Gomes, J.F.P. .P-xylene oxidation to terephthalic acid: A literature review oriented toward process optimization and development[J].Chemical Reviews,2013(10):7421-7469. |
[16] | Li K T;Li S W .[J].Applied Catalysis A:General,2008,340:271. |
[17] | Evans S;Lindsay Smith J R .[J].Journal of the Chemical Society Perkin Transactions,2000,2:1541. |
[18] | Shaabani A;Rahmati A .[J].CATALYSIS COMMUNICATIONS,2008,9:1692. |
[19] | Gupta M;Paul S;Gupta R;Loupy A .[J].Tetrahedron Letters,2005,46:4957. |
[20] | Poling B E;Prausnitz J M;O’Connell J P.The Properties of Gases and Liquids[M].New York:McGraw-Hill,2001:28. |
[21] | Savage P E .[J].Journal of Supercritical Fluids,2009,47:407. |
[22] | Dunn J B;Savage P E .[J].Industrial and Engineering Chemistry Research,2002,41:4460. |
[23] | Osada M;Savage P E .[J].AICHE Journal,2009,55:710. |
[24] | Garcia-Verdugo E;Venardou E;Thomas W B;Whiston K Parten-heimer W Hamley P A Poliakoff M .[J].Advanced Synthesis and Catalysis,2004,346:307. |
[25] | Garcia-Verdugo E;Fraga-Dubreuil J;Hamley PA;Thomas WB;Whiston K;Poliakoff M .Simultaneous continuous partial oxidation of mixed xylenes in supercritical water[J].Green chemistry,2005(5):294-300. |
[26] | Fraga-Dubreuil J;Poliakoff M .[J].Pure and Applied Chemistry,2006,78:1971. |
[27] | Hamley P A;Ilkenhans T;Webster J M;Garcia-Verdugo E Venar-dou E Clarke M J Auerbach R Thomas W B Whiston K Poliakoff M .[J].Green Chemistry,2002,4:235. |
[28] | Chavan S A;Srinivas D;Ratnasamy P .[J].Journal of Catalysis,2001,204:409. |
[29] | Sabater M J;Corma A;Domenech A;Forn’es V,Garcia H.[J].Chemistry Communications,1997:1285. |
[30] | Hutchings G J.[J].Chemistry Communications,1999:301. |
[31] | Falcon H;Campos-Martin J M;Al-Zahrani S M;Fierro J L G .[J].CATALYSIS COMMUNICATIONS,2010,12:5. |
[32] | Hermans I;Peeters J;Jacobs P A .[J].Topics in Catalysis,2008,50:124. |
[33] | Frank C E .[J].CHEMICAL REVIEWS,1950,46:155. |
[34] | Russell G A .[J].Journal of Chemical Education,1959,36:111. |
[35] | Mayo F R .[J].Accounts of Chemical Research,1968,1:193. |
[36] | Ichikawa Y;Yamashita G;Tokashiki M;Yamaji T .[J].Industrial and Engineering Chemistry,1970,62(04):38. |
[37] | Fan JW;Zhang RY .Atmospheric oxidation mechanism of p-xylene: A density functional theory study[J].The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory,2006(24):7728-7737. |
[38] | Guo Z;Liu B;Zhang Q H;Deng W P Wang Y Yang Y H .[J].CHEMICAL SOCIETY REVIEWS,2014,43:3480. |
[39] | Hronec M;Hrabe Z .[J].Industrial and Engineering Chemistry:Product Research and Development,1986,25:257. |
[40] | Jacob C R;Varkey S P;Ratnasamy P .[J].Applied Catalysis A:General,1999,182:91. |
[41] | Tibbitt J M;Gong W H;Schammel W P;Hepfer R P,Adamian V,Brugge S P,Metelski P D,Zhou C X .[P].WO Patent 133976 A2,2007. |
[42] | Kesavan L;Tiruvalam R;Ab Rahim M H;bin Saiman M I Enache D I Jenkins R L Dimitratos N Lopez-Sanchez J A Taylor S H Knight D W Kiely C J Hutching S G J .[J].SCIENCE,2011,331:195. |
[43] | Ab Rahim M H;Forde M M;Jenkins R L;Hammond C He Q Dimi-tratos N Lopez-Sanchez J A Carley A F Taylor S H Willock D J Murphy D M Kiely C J Hutching S G J .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2013,52:1280. |
[44] | Ab Rahim M H;Forde M M;Hammond C;Jenkins R L Dimitratos N Lopez-Sanchez J A Carley A F Taylor S H Willock D J Hutchings G J .[J].Topics in Catalysis,2013,56:1843. |
[45] | Deori K;Gupta D;Saha B;Awasthi S K Deka S .[J].J Mater Chem A,2013,1:7091. |
[46] | Qin Z Z;Su T M;Jiang Y X;Ji H B Qin W G .[J].CHEMICAL ENGINEERING JOURNAL,2014,242:414. |
[47] | Liu H L;Li Y W;Jiang H F;Vargas C Luque R .[J].Chemistry Communications,2012,48:8431. |
[48] | Della Pina C;Falletta E;Rossi M .[J].CHEMICAL SOCIETY REVIEWS,2012,41:350. |
[49] | Khan N A;Kennedy E M;Dlugogorski B Z;Adesina A A Stockenhuber M .[J].CATALYSIS COMMUNICATIONS,2014,53:42. |
[50] | Impeng S;Khongpracha P;Warakulwit C;Jansang B Sirijaraensre J Ehara M Limtrakul J .[J].RSC Adv,2014,4:12572. |
[51] | Liu H L;Chen G Z;Jiang H F;Li Y W Luque R .[J].ChemSusChem,2012,5:1892. |
[52] | Sheehan R J.Terephthalic Acid,Dimethyl Terephthalate,and Isophthalic Acid[M].Wiley-VCH,2002:156. |
[53] | Shigeyasu M;Kusano N .[P].US Patent 4160108,1979. |
[54] | Seko M;Miyake T;Takeuchi H;Tanouchi M .[P].US Patent 4230882A,1980. |
[55] | Scott L S;Sommers R W .[P].US Patent 158738,1979. |
[56] | Kahsar K R;Schwartz D K;Medlin J W .[J].Journal of the American Chemical Society,2014,136:520. |
[57] | Bramucci M G;McCutchen C M;Nagarajan V;Thomas S M.[J].Google Patents,2002 |
[58] | Bramucci M G;McCutchen C M;Nagarajan V;Thomas S M .[P].US Pa-tent 0170836,2003. |
[59] | Robert R;Ratnasamy P .[J].Journal of Molecular Catalysis A:Chemical,1995,100:93. |
[60] | M?ki-Arvela P;Kumar N;Nasir A;Salmi T Murzin D U .[J].Industrial and Engineering Chemistry Research,2005,44:9376. |
[61] | Marimuthu A;Zhang J W;Linic S .[J].SCIENCE,2013,339:1590. |
[62] | Lee I;Delbecq F;Morales R;Albiter M A Zaera F .[J].NATURE MATERIALS,2009,8:132. |
[63] | Wang Y;Zhang S J;Zhao Y X;Lin M .[J].Journal of Molecular Catalysis A:Chemical,2014,385:1. |
[64] | Yoo J S;Jhung S H;Lee K H;Park Y S .[J].Applied Catalysis A:General,2002,223:239. |
[65] | Zuo X B;Niu F H;Snavely K;Subramaniam B Busch D H .[J].Green Chemistry,2010,12:260. |
[66] | Zuo XB;Subramaniam B;Busch DH .Liquid-phase oxidation of toluene and p-toluic acid under mild conditions: Synergistic effects of cobalt, zirconium, ketones, and carbon dioxide[J].Industrial & Engineering Chemistry Research,2008(3):546-552. |
[67] | Park S E;Yoo J S .[J].Studies in surface science and catalysis,2004,153:303. |
[68] | Jhung S H;Park Y S;Lee K H;Chae J H,Yoo J S .[P].WO Patent 037407Al,2000. |
[69] | Raju G;Reddy B M;Park S E .[J].INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEO,2012,51:1315. |
[70] | Ali A M;Emanuelsson E A C;Patterson D A .[J].Applied Catalysis B:Environmental,2010,97:168. |
[71] | Wang S B;Zhu Z H .[J].Energy and Fuels,2004,18:1126. |
[72] | Yan N;Fu X Z;Chuang K T;Luo J L .[J].Journal of Power Sources,2014,254:48. |
[73] | Ma Z;Zaera F.Encyclopedia of Inorganic and Bioinorganic Chem-istry[M].Hoboken,New Jersey:John Wiley and Sons,2014:418. |
[74] | Pakhare D;Spivey J.[J].CHEMICAL SOCIETY REVIEWS,2014 |
[75] | Ansari M B;Park S E .[J].Energy Environ Sci,2012,5:9419. |
[76] | Brill W F .[J].Industrial and Engineering Chemistry,1960,52:837. |
[77] | Tashiro Y;Iwahama T;Sakaguchi;Ishii Y .[J].Advanced Synthesis and Catalysis,2001,343:220. |
[78] | Coseri, S .Phthalimide-N-oxyl (PINO) Radical, a Powerful Catalytic Agent: Its Generation and Versatility Towards Various Organic Substrates[J].Catalysis Reviews. Science and Engineering,2009(2):218-292. |
[79] | Xu H F;Tang R R;Gong N H;Liu C H Zhou Y P .[J].Progr Chem,2007,19:1736. |
[80] | Saha B;Koshino N;Espenson J H .[J].Journal of Physical Chemistry A,2004,108:425. |
[81] | Cheng YW;Li X;Wang LJ;Wang QB .Optimum ratio of Co/Mn in the liquid-phase catalytic oxidation of p-xylene to terephthalic acid[J].Industrial & Engineering Chemistry Research,2006(12):4156-4162. |
[82] | Cao N;Chang E;Kaufman M.Senior Design Report[M].University of Pennsylvania,2011 |
[83] | Zhang Y;Feng J;Lyu Z;Li X .[J].Modern Res Catal,2014,3:19. |
[84] | Horst A;Holmstrand H;Andersson P;Thornton B F Wishkerman A Keppler F Gustafsson O .[J].Geochimica et Cosmochimica Acta,2014,125:186. |
[85] | Schammel W P;Huggins B J;Kulzick M A;Nubel P O,Rabatic B M,Zhou C X,Adamian V A,Gong W H,Metelski P D,Miller J T .[P].US Pa-tent 8624055,2014. |
[86] | Masuno M N;Smith P B;Hucul D A;Dumitrascu A,Brune K,Smith R L,Bissell J,Foster M .[P].US Patent 0245316 A1,2013. |
[87] | Pacheco J J;Davis M E.[J].Proceedings of the National Academy of Sciences(USA),2014:345. |
[88] | Han I S;Kim M;Han C .[J].Theor Appl Chem Eng,2002,8:2989. |
[89] | Han I S;Kim M;Lee C H;Cha W Ham B K Jeong J H Lee H Chung C B Han C .[J].Korean Journal of Chemical Engineering,2003,20:977. |
[90] | Liu R L;Su H Y;Mu S J;Jia T Chen W Q Chu J .[J].Chinese Journal of Chemical Engineering,2004,12:234. |
[91] | Zhan Y;Su H Y;Liu R L;Chu J .[J].Chinese Journal of Chemical Engineering,2005,13:642. |
[92] | He H;Du W L;Qian F;Zhong W M .[J].Industrial and Engineering Chemistry Research,2010,49:5683. |
[93] | Makareviciene V;Skorupskaite V;Levisauskas D;Andruleviciute V Kazancev K .[J].INTERNATIONAL JOURNAL OF GREEN ENERGY,2014,11:527. |
[94] | Rasouli F;Aber S;Salari D;Khataee A R .[J].Applied Clay Seience,2014,87:228. |
[95] | Salman J M .[J].Arabian J Chem,2014,7:101. |
[96] | Roosta M;Ghaedi M;Daneshfar A;Darafarin S Sahraei R Purkait M K .[J].Ultrasonics Sonochemistry,2014,21:1441. |
[97] | Torrades F;García-Monta?o J .[J].Dyes and Pigments,2014,100:184. |
[98] | Wang S;Liu H P;Zhang Y;Yu J Yuan W .[J].Appl Mechanics Mater,2014,464:77. |
[99] | Pasma S A;Daik R;Maskat M Y;Hassan O .[J].Int J Polym Sci,2013,10:1. |
[100] | K?rbahti B K;Rauf M A .[J].CHEMICAL ENGINEERING JOURNAL,2008,136:25. |
[101] | Jeganathan P M;Venkatachalam S;Karichappan T;Ramasamy S .[J].Preparative Biochem Biotechnol,2014,44:56. |
[102] | Sharif K M;Rahman M M;Azmir J;Mohamed A Jahurul M H A Sahena F Zaidul I S M .[J].Journal of Food Engineering,2014,124:105. |
[103] | Grilc M;Likozar B;Levec J .[J].Applied Catalysis B:Environmental,2014,150-151:275. |
[104] | Mujtaba A;Ali M;Kohli K .[J].Chemical Engineering Research and Design,2014,92:156. |
- 下载量()
- 访问量()
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%