可再生生物质资源的开发与利用能够缓解化石燃料产生的温室气体对环境的负面影响.在生物质燃料制备过程中联产高附加值化学品能大幅提高生物质炼制的经济性.愈创木酚是常见的木质纤维素快速热解产物.本文研究了低温液相氧化愈创木酚制备马来酸,并重点考察了催化剂添加量、pH值、反应时间和反应温度等反应条件的影响.研究发现,在钛硅沸石-过氧化氢碱溶液氧化反应体系中(80°C, pH=13.3),20-30 mol%的愈创木酚可以选择性转化为马来酸.同时初步探讨了愈创木酚氧化开环转化为马来酸的反应机理.
To mitigate the negative environmental impact of greenhouse gas (GHG) emission originated from the use of fossil fuels, the chemical world is switching to utilize renewable biomass resources. Co-producing value-added chemicals is important for an integrated biorefinery to improve eco-nomics of biofuels. Lignin derived compounds, e.g. guaiacol, are common by-products of fast pyroly-sis of lignocellulosic biomass. In this paper, the feasibility of low-temperature selective oxidation of guaiacol to value-added dicarboxylic acids, e.g. maleic acid, was investigated using titanium sili-calite/hydrogen peroxide (TS-1/H2O2) reaction system. Under the reaction conditions (80 °C and the initial pH=13.3), the molar yields of maleic acid from guaiacol were approximately 20%-30%. The effects of catalyst amount, initial pH values, reaction time, and temperature on the yields of maleic acid were investigated. A possible reaction mechanism of TS-1 catalyzed aromatic ring opening was proposed.
参考文献
[1] | U.S.Billion-Ton Update:Biomass Supply for a Bioenergy and Bioproducts Industry[M].,2011 |
[2] | Bridgwater A V;Meier D;Radlein D .[J].Organic Geochemistry,1999,30:1479. |
[3] | Pattiya A;Titiloye J O;Bridgwater A V .[J].FUEL,2010,89:244. |
[4] | Nowakowski D J;Bridgwater A V;Elliott D C;Meier D de Wild P .[J].Journal of Analytical and Applied Pyrolysis,2010,88:53. |
[5] | Bridgwater A V;Peacocke G V C .[J].RENEWABLE & SUSTAINABLE ENERGY REVIEWS,2000,4:1. |
[6] | Vispute T P;Zhang H Y;Sanna A;Xiao R Huber G W .[J].SCIENCE,2010,330:1222. |
[7] | Carlson T R;Tompsett G A;Conner W C;Huber G W .[J].Topics in Catalysis,2009,52:241. |
[8] | Bridgwater, A. V..Review of fast pyrolysis of biomass and product upgrading. (Special Issue: Overcoming barriers to bioenergy: outcomes of the Bioenergy Network of Excellence 2003-2009.)[J].Biomass & Bioenergy,2012:68-94. |
[9] | Zhang Q;Chang J;Wang T J;Xu Y .[J].Energy Convers Manag,2007,48:87. |
[10] | de Miguel Mercader F;Groeneveld M J;Kersten S R A;Geantet C Toussaint G Way N W J Schaverien C J Hogendoorn K J A .[J].Energy Environ Sci,2011,4:985. |
[11] | Crossley S;Faria J;Shen M;Resasco D E .[J].SCIENCE,2010,327:68. |
[12] | Zakzeski, J.;Bruijnincx, P.C.A.;Jongerius, A.L.;Weckhuysen, B.M. .The catalytic valorization of lignin for the production of renewable chemicals[J].Chemical Reviews,2010(6):3552-3599. |
[13] | Furimsky E. .Catalytic hydrodeoxygenation [Review][J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2000(2):147-190. |
[14] | Zhao C;Kou Y;Lemonidou A A;Li X Lercher J A .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2009,121:4047. |
[15] | Gutierrez A;Kaila R K;Honkela M L;Slioor R Krause A O I .[J].Catalysis Today,2009,147:239. |
[16] | Bykova M V;Ermakov D Yu;Kaichev V V;Bulavchenko O A Saraev A A Lebedev M Y Yakovlev V А .[J].Applied Catalysis B:Environmental,2012,113-114:296. |
[17] | Jongerius A L;Jastrzebski R;Bruijnincx P C A;Weckhuysen B M .[J].Journal of Catalysis,2012,285:315. |
[18] | Ruiz P E;Frederick B G;De Sisto W J;Austin R N Radovic L R Leiva K García R Escalona N Wheeler M C .[J].CATALYSIS COMMUNICATIONS,2012,27:44. |
[19] | Ghampson I T;Sepúlveda C;Garcia R;Radovic L R Fierro J L G DeSisto W J Escalona N .[J].Applied Catalysis A:General,2012,439-440:111. |
[20] | Zhang X H;Wang T J;Ma L L;Zhang Q Yu Y X Liu Q Y .[J].CATALYSIS COMMUNICATIONS,2013,33:15. |
[21] | Zhao H Y;Li D;Bui P;Oyama S T .[J].Applied Catalysis A:General,2011,391:305. |
[22] | Bui V N;Laurenti D;Delichère P;Geantet C .[J].Applied Catalysis B:Environmental,2011,101:246. |
[23] | Lee C R;Yoon J S;Suh Y-W;Choi J-W Ha J-M Suh D J Park Y-K .[J].CATALYSIS COMMUNICATIONS,2012,17:54. |
[24] | Wu S-K;Lai P-C;Lin Y-C;Wan H-P Lee H-T Chang Y-H .[J].ACS Sustain Chem Eng,2013,1:349. |
[25] | Ghampson I T;Sepúlveda C;Garcia R;García Fierro J L Escalona N DeSisto W J .[J].Applied Catalysis A:General,2012,435-436:51. |
[26] | Nimmanwudipong T;Runnebaum R C;Block D E;Gates B C .[J].Energy and Fuels,2011,25:3417. |
[27] | Bui V N;Laurenti D;Afanasiev P;Geantet C .[J].Applied Catalysis B:Environmental,2011,101:239. |
[28] | Deutsch K L;Shanks B H .[J].Applied Catalysis A:General,2012,447-448:144. |
[29] | Olcese R;Bettahar M M;Malaman B;Ghanbaja J Tibavizco L Petitjean D Dufour A .[J].Applied Catalysis B:Environmental,2013,129:528. |
[30] | Olcese R N;Bettahar M;Petitjean D;Malaman B Giovanella F Dufour A .[J].Applied Catalysis B:Environmental,2012,115-116:63. |
[31] | Nimmanwudipong T;Runnebaum R C;Block D E;Gates B C .[J].Catalysis Letters,2011,141:779. |
[32] | Sasaki M;Goto M;Mater J .[J].Cycles Waste Manag,2011,13:68. |
[33] | Kanetake T;Sasaki M;Goto M .[J].Chemical Engineering & Technology,2007,30:1113. |
[34] | Suzuki H;Cao J;Jin F;Kishita A;Enomoto H;Moriya T .Wet oxidation of lignin model compounds and acetic acid production[J].Journal of Materials Science,2006(5):1591-1597. |
[35] | Devlin H R;Harris I J .[J].INDUSTRIAL & ENGINEERING CHEMISTRY FUNDAMENTALS,1984,23:387. |
[36] | Santos A;Yustos P;Quintanilla A;Ruiz G Garcia-Ochoa F .[J].Applied Catalysis B:Environmental,2005,61:323. |
[37] | Santos A;Yustos P;Quintanilla A;García-Ochoa F Casas J A Rodríguez J J .[J].Environmental Science and Technology,2004,38:133. |
[38] | Santos A.;Yustos P.;Quintanilla A.;Rodriguez S.;Garcia-Ochoa F. .Route of the catalytic oxidation of phenol in aqueous phase[J].Applied Catalysis, B. Environmental: An International Journal Devoted to Catalytic Science and Its Applications,2002(2):97-113. |
[39] | Wu Z C;Zhou M H .[J].Environmental Science and Technology,2001,35:2698. |
[40] | Zazo J A;Casas J A;Molina C B;Quintanilla A Rodriguez J J .[J].Environmental Science and Technology,2007,41:7164. |
[41] | Felthouse T R;Burnett J C;Mitchell S F;Mummey M J.[J].Van Nostrand’s Encycl Chem,2005:1. |
[42] | Lin H F;Strull J;Liu Y;Karmiol Z Plank K Miller G Guo Z H Yang L S .[J].Energy Environ Sci,2012,5:9773. |
[43] | Thangaraj A;Sivasanker S.[J].Journal of the Chemical Society Chemical Communications,1992:123. |
[44] | Blanco-Brieva G;Capel-Sanchez M C;de Frutos M P;Padilla-Polo A Campos-Martin J M Fierro J L G .[J].Industrial and Engineering Chemistry Research,2008,47:8011. |
[45] | Clerici M G .[J].Topics in Catalysis,2001,15:257. |
[46] | Klemm, E;Dietzsch, E;Schwarz, T;Kruppa, T;de Oliveira, AL;Becker, F;Markowz, G;Schirrmeister, S;Schutte, R;Caspary, KJ .Direct gas-phase epoxidation of propene with hydrogen peroxide on TS-1 zeolite in a microstructured reactor[J].Industrial & Engineering Chemistry Research,2008(6):2086-2090. |
[47] | Beziat J-C;Besson M;Gallezot P;Durecu S .[J].Journal of Catalysis,1999,182:129. |
[48] | Oliviero L;Barbier J Jr;Duprez D;Wahyu H Ponton J W Metcalfe I S Mantzavinos D .[J].Applied Catalysis B:Environmental,2001,35:1. |
[49] | Hamoudi S.;Sayari A.;Larachi F. .Wet oxidation of phenolic solutions over heterogeneous catalysts: Degradation profile and catalyst behavior[J].Journal of Catalysis,1998(2):247-258. |
[50] | Akolekar D B;Bhargava S K;Shirgoankar I;Prasad J .[J].Applied Catalysis A:General,2002,236:255. |
[51] | Gomes H T;Figueiredo J L;Faria J L .[J].Applied Catalysis B:Environmental,2000,27:L217. |
[52] | Beziat J C;Besson M;Gallezot P;Durecu S .[J].Industrial and Engineering Chemistry Research,1999,38:1310. |
[53] | Pintar A.;Gallezot P.;Besson M. .Catalytic wet air oxidation of Kraft bleaching plant effluents in the presence of titania and zirconia supported ruthenium[J].Applied Catalysis, B. Environmental: An International Journal Devoted to Catalytic Science and Its Applications,2001(1/2):123-139. |
[54] | Imamura S .[J].Industrial and Engineering Chemistry Research,1999,38:1743. |
[55] | Bhargava S;Jani H;Tardio J;Akolekar D Hoang M .[J].Industrial and Engineering Chemistry Research,2007,46:8652. |
[56] | Luck F .[J].Catalysis Today,1999,53:81. |
[57] | Doerge D R;Divi R L;Churchwell M I .[J].Analytical Biochemistry,1997,250:10. |
[58] | Taurog A;Dorris M L;Guziec F S Jr .[J].Analytical Biochemistry,1992,205:271. |
[59] | Mijangos F;Varona F;Villota N .Changes in solution color during phenol oxidation by Fenton reagent[J].Environmental Science & Technology: ES&T,2006(17):5538-5543. |
[60] | Regeimbal J;Gleiter S;Trumpower B L;Yu C-A Diwakar M Ballou D P Bardwell J C A .[J].Proceedings of the National Academy of Sciences(USA),2003,100:13779. |
[61] | Bonino F;Damin A;Ricchiardi G;Ricci M Spano G D'Aloisio R Zecchina A Lamberti C Prestipino C Bordiga S .[J].Journal of Physical Chemistry B,2004,108:3573. |
[62] | Chaudhari K;Srinivas D;Ratnasamy P .[J].Journal of Catalysis,2001,203:25. |
[63] | Shetti VN.;Manikandan P.;Srinivas D.;Ratnasamy P. .Reactive oxygen species in epoxidation reactions over titanosilicate molecular sieves[J].Journal of Catalysis,2003(1/2):461-467. |
[64] | Srinivas D.;Manikandan P.;Laha SC.;Kumar R.;Ratnasamy P. .Reactive oxo-titanium species in titanosilicate molecular sieves: EPR investigations and structure-activity correlations[J].Journal of Catalysis,2003(1):160-171. |
[65] | Wang L L;Xiong G;Su J;Li P Guo H C .[J].J Phys Chem C,2012,116:9122. |
[66] | Gleeson D;Sankar G;Catlow C R A;Thomas J M Spano G Bordiga S Zecchina A Lamberti C .[J].Physical Chemistry Chemical Physics,2000,2:4812. |
[67] | Zhao Q.;Wang Y.;Lin LW.;Gang L.;Guo XW.;Wang XS.;Bao XH. .Studies on superoxide O-2(-) species on the interaction of TS-1 zeolite with H2O2[J].Journal of molecular catalysis, A. Chemical,2000(1/2):265-268. |
[68] | Shetti V N;Srinivas D;Ratnasamy P .[J].Journal of Molecular Catalysis A:Chemical,2004,210:171. |
- 下载量()
- 访问量()
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%