Advances in the Research and Development of Acrylic Acid Production from Biomass

Abstract

Abstract: The shortage of petroleum has resulted in worldwide efforts to produce chemicals from renewable resources. Among these attempts, the possibility of producing acrylic acid from biomass has caught the eye of many researchers. Converting the carbohydrates first to lactic acid by fermentation and then dehydrating lactic acid to acrylic acid is hitherto the most effective way for producing acrylic acid from biomass. While the lactic acid fer-mentation has been commercialized since longer times, the dehydration process of lactic acid is still under devel-opment because of its low yield. Further efforts should be made before this process became economically feasible. Because of the existence of acrylic acid pathways in some microorganisms, strain improvement and metabolic en-gineering provides also a possibility to produce acrylic acid directly from biomass by fermentation.

Key words: renewable resource, acrylic acid, biomass, lactic acid

摘要： The shortage of petroleum has resulted in worldwide efforts to produce chemicals from renewable resources. Among these attempts, the possibility of producing acrylic acid from biomass has caught the eye of many researchers. Converting the carbohydrates first to lactic acid by fermentation and then dehydrating lactic acid to acrylic acid is hitherto the most effective way for producing acrylic acid from biomass. While the lactic acid fer-mentation has been commercialized since longer times, the dehydration process of lactic acid is still under devel-opment because of its low yield. Further efforts should be made before this process became economically feasible. Because of the existence of acrylic acid pathways in some microorganisms, strain improvement and metabolic en-gineering provides also a possibility to produce acrylic acid directly from biomass by fermentation.

关键词: renewable resource;acrylic acid;biomass;lactic acid

XUXiaobo, LINJianping, CENPeilin. Advances in the Research and Development of Acrylic Acid Production from Biomass
[J]. .

许晓波, 林建平, 岑沛霖. 从生物量生产丙烯酸的研究和开发进展[J]. CIESC Journal.

References

1    Wheals, A.E., Basso, L.C., Alves, D.M.G., Amorim, H.V., “Fuel ethanol after 25 years”, Trends Biotechnol., 17(12), 482—487(1999).
2    Wang, C.Y., Zhao, Y.M., “Synthesis of biodegradable material polylactic acid”, Chem. Ind. Eng. Progr., 22(7), 678—680(2003). (in Chinese)
3    Jin, L.G., Ni, R.Q., “Study on polylactic acid fibers”, Synth. Fiber, 32(2), 25—27(2003). (in Chinese)
4    Hong, Z.L., The Machining of the Organic Chemical Material, Chemical Industry Press, Beijing, 363—400(1997). (in Chinese)
5    Yan, R.X., Water-Soluble Macromolecule, Chemical Industry Press, Beijing, 196—222(1998). (in Chinese)
6    Falbe, J., Rebitz, M., Römpp, H., Römpp Chemie Lexikon, Thieme, Stuttgart (1995).
7    Buchta, K., “Lactic acid”, In: Biotechnology, Dellweg, H., ed., Verlag Chemie, Weinheim, Federal Republic of Germany, 3, 409—417(1983).
8    Du, J.X., Cao, N.J., “Production of L-lactic acid by Rhizopus oryzae in a bubble column fermenter”, Appl. Biochem. Biotechnol., 70-72, 323—329(1998).
9    Li, X.M., Lin, J.P., Liu, M.E., Cen, P.L., “Repeated-batch and continuous production of L-lactic acid by Rhizopus oryzae immobilized in calcium alginate beads: Perform-ance and kinetic model”, Chin. J. Chem. Eng., 6(4),  330—339(1998).
10    Luo, J., Xia, L.M., Lin, J.P., Cen, P.L., “Kinetics of si-multaneous saccharification and lactic acid fermentation processes”, Biotechnol. Progr., 13(6), 762—767(1997).
11    Chauhan, R.P., Woodley, J.M., “Increasing the produc-tivity of bioconversion processes”, Chemtech., 27, 26—39(1997).
12    Lu, Y.H., Lin, J.P., Li, S.Z., Li, X.M., Yao, S., Cen P.L., “Extractive L-lactic acid fermentation with immobilized Rhizopus oryzae in a three-phase fluidized bed”, Chin. J. Biotechnol., 13(3), 169—176(1997).
13    Kailas, L.W., Bert, M.H., Geert, F.V., Vishwas, G.P., “Re-active extraction of lactic acid using alamine 336 MIBK: Equilibria and kinetics”, J. Biotechnol., 97(1), 59—68(2002).
14    Jarvinen, M., Myllykoski, L., Keiski, R., Sohlo, J., “Separation of lactic acid from fermented broth by reac-tive extraction”, Bioseparation, 9(3), 163—166(2000).
15    Kahya, E., Bayraktar, E., Mehmetoğlu, ü., “Optimization of process parameter for reactive lactic acid extraction”, Turk. J. Chem., 25, 223—230(2001).
16    Tik, N., Bayraktar, E., Mehmetoglue, U., “In-situ reac-tive extraction of lactic acid from fermentation media”, J. Chem. Tech. Biotech., 76, 764—768(2001).
17    Lin, J.P., Chen, B., Wu, J.P., Cen, P.L., “L-lactic acid fermentation in a rotating disc contactor with simultane-ous product separation by ion exchange”, Chin. J. Chem. Eng., 5(1), 49—55(1997).
18    Chol, J.I., Hong, W.H., “Recovery of lactic acid by batch distillation with chemical reactions using ion exchange resin”, J. Chem. Eng. Jpn., 32, 184—189(1999).
19    Cao, X.J., Yun, H.S., Koo, Y.M., “Recovery of L(+)-lactic acid by anion exchange resin Amberlite IRA-400”, Biochem. Eng. J., 11, 189—196(2002).
20    Tong, W.Y., Fu, X.Y., Lee, S.M., Yu, J., Liu, J.W., Wei, D.Z., Koo, Y.M., “Purification of L(+)-lactic acid from fermentation broth with paper sludge as a cellulosic feedstock using weak anion exchanger Amberlite IRA-92”, Biochem. Eng. J., 18, 89—96(2004).
21    Li, X.M., Lin, J.P., Liu, M.E., “L-lactic acid production using immobilized Rhizopus oryzae in a three-phase flu-idized-bed with simultaneous product separation by electrodialysis”, Bioproc. Eng., 20, 231—237(1999).
22    Timmer, J.K.M., Kromkamp, J., Robbertsen, T., “Lactic acid separation from fermentation broth by reverse os-mosis and nanofiltration”, J. Membr. Sci., 92, 185—197(1994).
23    Madzingaidzo, L., Danner, H., Braun, R., “Process de-velopment and optimization of lactic acid purification using electrodialysis”, J. Biotechnol., 96, 223—239(2002).
24    Tejayadi, S., Cheryan, M., “Lactic acid from cheese whey permeate. Productivity and economics of a con-tinuous membrane bioreactor”, Appl. Microbiol. Bio-technol., 43 (2), 242—248(1995).
25    Vishal, S., Nikki, G., Datta, M., “Lactic acid fermentation in cell-recycle membrane bioreactor”, Appl. Biochem. Biotechnol., 128(2), 171—184(2006).
26    Siebold, M., Frieling, P., Joppien, R., Rindfleisch, D., Schügerl, K., Röper, H., “Comparison of the production of lactic acid by three different lactobacilli and its recov-ery by extraction and electrodialysis”, Proc. Biochem., 30(1), 81—95(1995).
27    Hano, T., Matsumoto, M., Uenoyama, S., Ohtake, T., Kawano, Y., Miura, S., “Separation of lactic acid from fermented broth by solvent extraction”, Bioseparation, 3, 321—326(1993).
28    Roukas, T., Kotzekidou, P., “Lactic acid production from deproteinized whey by mixed cultures of free and coim-mobilized Lactobacillus casei and Lactococcus lactis cells using fedbatch culture”, Enzyme Microb. Technol., 22, 199—204(1998).
29    Bai, D.M., Wei, Q., Yan, Z.H., Zhao, X.M., Li, X.G., Xu, S.M., “Fed-batch fermentation of Lactobacillus lactis for hyper-production of L-lactic acid”, Biotechnol. Let., 25, 1833—1835(2003).
30    Wasewar, K.L., Heesink, A.B.M., Versteeg, G.F., Pan-garkar, V.G., “Equilibria and kinetics for reactive extrac-tion of lactic acid using Alamine 336 in decanol”, J. Chem. Tech. Biotechnol., 77, 168(2002).
31    Kascak, S., Kominek, J., Roehr, M., “Lactic acid”, Bio-technol. Bioeng., 28, 269—282(1986).
32    Sanz, M.T., Murga, R., Beltran, S., Cabezas, J.L., “Ki-netic study for the reactive system of lactic acid esterifi-cation with methanol: Methyl lactate hydrolysis reac-tion”, J. Ind. Eng. Chem., 43 (9), 2049—2053(2004).
33    Wei, T.Y., Tong, Z.F., “Water separation of esterification by azeotropic rectification with partial condensation”, Chin. J. Proc. Eng., 4(4), 300—304(2004).
34    Ohara, H., Ito, M., Sawa, S., “Process for producing lac-tide and process for producing polylactic acid from fer-mented lactic acid employed as starting material”, U. S. Pat., 6569989 (2003).
35    Wang, Q.H., Sun, X.H., Ma,R., “Study on synthesis of polylactide from kitchen garbage”, J. Chin. Sci. Bull., 50(13), 1315—1319(2005).
36    Ma, L., Zhang, Y., Yang, J.C., “Purification of lactic acid by heterogeneous catalytic distillation using ion-exchange resins”, Chin. J. Chem. Eng., 13(1), 24—31(2005).
37    Zhang, M., Ma, L., Yang, J.C., Xu, Y.M., “Non-equilibrium stage static simulation of lactic acid purification reactive distillation process”, J. Chem. Ind. Eng. (China), 56(6), 1031—1034(2005). (in Chinese)
38    Roux-de Balmann, H., Bailly, M., Lutin, F., Aimar, P., “Modelling of the conversation of weak organic acids by bipolar membrane electrodialysis”, Desalination, 149, 399—404(2002).
39    Carrère, H., Blaszkow, F., “Comparison of operating modes for clarifying lactic acid fermentation broths by batch cross-flow microfiltration”, Proc. Biochem., 36, 751—756(2001).
40    Carrère, H., Blaszkow, F., Balmann, H.R., “Modelling of the clarification of lactic acid fermentation broths by cross-flow microfiltration”, J. Membr. Sci., 186, 219—230(2001).
41    Wadley, D.C., Man, S.T., Dennis, J.M., “Lactic acid con-version to 2,3-pentanedione and acrylic acid over sil-ica-supported sodium nitrate: Reaction optimization and identification of sodium lactate as the active catalyst”, J. Catal., 165, 162—171(1997).
42    Gunter, G.C., Jackson, J.E., Miller, D.J., “Formation of 2,3-pentanedione from lactic acid over supported phos-phate catalysts”, J. Catal., 148, 252—260(1994).
43    Walkup, P.C., Rohrmann, C.A., Hallen, R.T., Eakin, D.E., “Production of esters of lactic acid, esters of acrylic acid, lactic acid, and acrylic acid”, U. S. Pat., 5252473 (1993).
44    Adkins, H., Billica, H.R., “The hydrogenation of esters to alcohols at 25—150℃”, J. Am. Chem. Soc., 70, 3121 (1948).
45    Lunt, J., “Large-scale production, properties, and com-mercial applications of polylactic acid polymers”, Polym. Degrad. Stab., 59, 145—152(1998).
46    Holmen, R.E., “Acrylates by catalytic dehyddration of lactic acid and acrylates”, U. S. Pat., 2859240 (1958).
47    Sawicki, R.A., “Catalyst for dehydration of lactic acid to acrylic acid”, U. S. Pat., 4729978 (1988).
48    Paparizos, C., Dolhyj, S., Shaw, W.G., “Catalytic conver-sion of lactic acid and ammonium lactate to acrylic acid”, U. S. Pat., 4786756 (1988).
49    Mok, W., Antal, M.J., “Formation of acrylic acid from lactic acid in supercritical water”, J. Org. Chem., 54, 4596—4602 (1989).
50    Perry, J.M., Carl, T.L., “Conversion of lactic acid to acrylic acid in supercritical water”, Ind. Eng. Chem. Res., 32, 2608—2613(1993).
51    Burns, R., Jones, D.T., Ritchie P.D., “Studies in pyrolysis part I. The pyrolysis of derivatives of al-pha-acetoxypropionic acid and related substances”, J. Chem. Soc., 400—406(1935).
52    Smith, L.T., Fisher, C.H., Ratchford, W.P. , “Pyrolysis of lactic acid derivatives”, Ind. Eng. Chem., 34, 473—479(1942).
53    Fisher, C.H., Ratchford, W.P., “Methyl acrylate produc-tion”, Ind. Eng. Chem., 36, 229—334(1944).
54    Ratchford, W.P., Fisher, C.H., “Methyl acrylate by pyro-lysis of methyl acetoxypropionate”, Ind. Eng. Chem., 37, 382—387(1945).
55    Lilga, M.A., Werpy, T.A., Holladay, J.E., “Methods of forming alpha, beta-unsaturated acids and esters”, U. S. Pat. Appl., 0110974 (2004).
56    Werpy, T.A., Lilga, M.A., “Ester compounds and their use in forming acrylates”, U. S. Pat., 6545175 (2003).
57    Michael, A.L., Todd, A.W., Johnathan, E.H., “Methods of forming alpha, beta-unsaturated acids and esters”, U. S. Pat., 6992209 (2006).
58    Nagasawa, T., Nakamura, T., Yamada, H., “Production of acrylic acid and methacrylic acid using Rhodococcus rhodochrous Jl nitrilase”, Appl. Microbiol. Biotechnol., 34, 322—324(1990).
59    Narayanasamy, K., Shukla, S., Parekh, L.J., “Utilization of acrylonitrile by bacteria isolated from petrochemical waste waters”, Indian J. Exp. Biol., 28, 968—971(1990).
60    Nawaz, M.S., Franklin, W., Cerniglia, C.E., “Degrada-tion of acrylamide by immobilized cells of a Pseudomo-nas sp. and Xant homonas maltophilia”, Can. J. Micro-biol., 39, 207—212(1993).
61    Nawaz, M.S., Franklin, W., Cerniglia, C.E., “Degrada-tion of aliphatic amide mixture by immobilized and nonimmobilized cells of Pseudomonas sp.”, Environ. Sci. Technol., 28, 1106—1109(1994).
62    Gartner, D.H., Braun, R., “Biotechnological production of acrylic acid from biomass”, Appl. Biochem. Biotech-nol. Progr., 70(2), 887—894(1998).
63    Dalal, R.K., Akedo, M., Cooney, C.L., Sinskey, A.J., “ A microbial route to acrylic acid production”, Biosources Dig., 2 (2), 89—97(1980).
64    Sanseverino, J., Montenecourt, B.S., Sands, J.A., “De-tection of acrylic aicd formation in Megasphaera els-denii in the presence of 3-butynoic acid”, Appl. Micro-biol. Biotechnol., 30, 239—242(1989).
65    O’Brien, D.J., Panzer, C.C., Eisele, W.P., “Biological production of acrylic acid from cheese whey by resting cells of Clostridium propionicum”, Biotechnol. Progr., 6, 237—242(1990).
66    Cameron, D.C., Suthers, P.F., “Production of 3-hydroxypropanoic acid in recombinant organisms”, World Pat. WO, 0116346 (2001).
67    Buckel, W., Selmer, T., Selofonova, O.V., Gokarn, R.R., Gort, S.J., Jessen, H., “3-Hydroxypropanoic acid and other organic compounds”, World Pat. WO, 0242418 (2002).
68    Gokam, R.R., Gort, S.J., Liao, H.H., Jessen, H.J., Selo-fonova, O.V., “Alanine-2,3-aminomutase”, World Pat. WO, 03062173 (2003).
69    Ishii, M., Chuakrut, S., Arai, H., Igarashi, Y., “Occur-rence, biochemistry and possible biotechnological appli-cation of the 3-hydroxypropionate cycle”, Appl. Micro-biol. Biotechnol., 64, 605—610(2004).
70    Straathof, A.J.J., Sie, S., Franco, T.T., Wielen, L.A.M., “Feasibility of acrylic acid production by fermentation”, Appl. Microbiol. Biotechnol., 67, 727—734(2005).

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Advances in the Research and Development of Acrylic Acid Production from Biomass

从生物量生产丙烯酸的研究和开发进展

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