长链脂肪族二元酸的合成及其在缩聚反应中的应用
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摘要
长链脂肪族二元酸一般是指含有10个或以上碳原子的饱和直链二元酸,其两端带有羧基官能团,可用于合成香料、特种尼龙工程塑料、热熔胶、涂料、增塑剂、高级润滑油等众多化工产品;由于其链段中含有长烷烃链段,具有优于短链二元酸的性质,使得相应的合成材料具有优越的性能,因此广泛应用于化工、轻工、国防、汽车工业、工程材料等领域;同时,还可用于开发新的聚合物产品。长链脂肪族二元酸在自然界中不单独存在,目前工业上主要通过化学合成法和生物发酵法生产。本文主要对长链脂肪族二元酸的合成方法进行综述,包括传统有机合成、生物技术转化、烯烃复分解、异构化-氢氧羰基化及聚乙烯端基功能化等,并简要概述长链脂肪族二元酸在缩聚反应(聚酯和聚酰胺)中的应用。最后,对合成方法待解决的问题进行了总结,并对未来发展方向进行了展望。
Long-chain aliphatic dicarboxylic acids generally refer to the saturated straight-chain dicarboxylic acids containing ten or more carbon atoms. Due to the existence of carboxyl functional groups in each terminal, they are usually applied to synthesize perfumes, special nylon engineering plastics, hot melt adhesives, coatings, plasticizers, senior lubricants and many other chemical products. In addition, they have better properties than short-chain dicarboxylic acids because of their long methylene sequences, which makes the corresponding composite materials have superior performance and be widely used in chemical industry, light industry, national defense, automobile industry, engineering materials and other fields. Besides, they could be also used to develop new polymer products. Long-chain aliphatic dicarboxylic acids do not exist alone in nature. At present, they have been synthesized mainly via chemical synthesis and biological fermentation in industry. In this review, the synthetic methods of long-chain aliphatic dicarboxylic acids are summarized, including traditional organic synthesis, biotechnology conversion, olefin metathesis, isomerization hydroxycarbonylation and functionalization of polyethylene. The application of long-chain aliphatic dicarboxylic acids in the polycondensation(mainly of polyesters and polyamides) is also briefly introduced. Finally, the problems remaining to be solved in the synthesis and the further advances are prospected.
Long-chain aliphatic dicarboxylic acids generally refer to the saturated straight-chain dicarboxylic acids containing ten or more carbon atoms. Due to the existence of carboxyl functional groups in each terminal, they are usually applied to synthesize perfumes, special nylon engineering plastics, hot melt adhesives, coatings, plasticizers, senior lubricants and many other chemical products. In addition, they have better properties than short-chain dicarboxylic acids because of their long methylene sequences, which makes the corresponding composite materials have superior performance and be widely used in chemical industry, light industry, national defense, automobile industry, engineering materials and other fields. Besides, they could be also used to develop new polymer products. Long-chain aliphatic dicarboxylic acids do not exist alone in nature. At present, they have been synthesized mainly via chemical synthesis and biological fermentation in industry. In this review, the synthetic methods of long-chain aliphatic dicarboxylic acids are summarized, including traditional organic synthesis, biotechnology conversion, olefin metathesis, isomerization hydroxycarbonylation and functionalization of polyethylene. The application of long-chain aliphatic dicarboxylic acids in the polycondensation(mainly of polyesters and polyamides) is also briefly introduced. Finally, the problems remaining to be solved in the synthesis and the further advances are prospected.
引文
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[73] Quinzler D, Mecking S. Angew. Chem. Int. Ed., 2010, 49: 4306.
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[2] Kroha K. Inform, 2004, 15: 568.
[3] Mecking S. Angew. Chem. Int. Ed., 2004, 43: 1078.
[4] Stempfle F, Quinzler D, Heckler I, Mecking S. Macromolecules, 2011, 44: 4159.
[5] Chuit P, Hausser J. Helv. Chim. Acta, 1929, 12: 850.
[6] Kreuchunas A. J. Am. Chem. Soc., 1953, 75: 3339.
[7] Hünig S, Lücke E, Brenninger W. Docosanedioic Acid. Org. Synth., 1973, 5: 533.
[8] Hunig S, Lucke E. Chem. Ber. Recl., 1959, 92: 652.
[9] Hunig S, Lendle W. Chem. Ber. Recl., 1960, 93: 913.
[10] Hunig S, Buysch H J. Chem. Ber. Recl., 1967, 100: 4010.
[11] Hunig S, Buysch H J. Chem. Ber. Recl., 1967, 100: 4017.
[12] Brooke G M, Burnett S, Mohammed S, Proctor D, Whiting M C. J. Chem. Soc. Perkin Trans., 1996, 1: 1635.
[13] Genas M. Angew. Chem. Int. Ed., 1962, 74: 535.
[14] Naughton F C. J. Am. Oil Chem. Soc., 1974, 51: 65.
[15] Brown A C, Goebel C G, Oehlschlaeger H F, Rolfes R P. US 2813113A, 1957.
[16] Zibek S, Huf S, Wagner W, Hirth T, Rupp S. Chem. Ing. Tech., 2009, 81: 1797.
[17] Schorken U, Kempers P. Eur. J. Lipid Sci. Technol., 2009, 111: 627.
[18] Abghari A, Madzak C, Chen S. Ferment., 2017, 3: 40.
[19] Sathesh-Prabu C, Lee S K. J. Agric. Food Chem., 2015, 37: 8199.
[20] Lee H, Sugiharto Y E C, Lee S, Park G, Han C, Jang H, Jeon W, Park H, Ahn J, Kang K, Lee H. Appl. Microbiol. Biotechnol., 2017, 16: 6333.
[21] Huf S, Krugener S, Hirth T, Rupp S, Zibek S. Eur. J. Lipid Sci. Technol., 2011, 113: 548.
[22] Picataggio S, Deanda K, Mielenz J. Mol. Cell. Biol., 1991, 11: 4333.
[23] Eschenfeldt W H, Zhang Y Y, Samaha H, Stols L, Eirich L D, Wilson C R, Donnelly M I. Appl. Environ. Microbiol., 2003, 69: 5992.
[24] Cao Z, Gao H, Liu M, Jiao P. Biotechnol. J., 2006, 1: 68.
[25] Schrewe M, Magnusson A O, Willrodt C, Buhler B, Schmid A. Adv. Synth. Catal., 2011, 353: 3485.
[26] Julsing M K, Schrewe M, Cornelissen S, Hermann I, Schmid A, Buhler B. Appl. Environ. Microbiol., 2012, 78: 5724.
[27] Lu W H, Ness J E, Xie W C, Zhang X Y, Liu F, Cai J L, Minshull J, Gross R A. J. Am. Chem. Soc., 2010, 132: 15451.
[28] Malca S H, Scheps D, Kuhnel L, Venegas-Venegas E, Seifert A, Nestl B M, Hauer B. Chem. Commun., 2012, 48: 5115.
[29] Scheps D, Malca S H, Richter S M, Marisch K, Nestl B M, Hauer B. Microb. Biotechnol., 2013, 6: 694.
[30] Schrewe M, Ladkau N, Buhler B, Schmid A. Adv. Synth. Catal., 2013, 355: 1693.
[31] Song J W, Jeon E Y, Song D H, Jang H Y, Bornscheuer U T, Oh D K, Park J B. Angew. Chem. Int. Ed., 2013, 52: 2534.
[32] Werner N, Dreyer M, Wagner W, Papon N, Rupp S, Zibek S. Biotechnol. Lett., 2017, 3: 429.
[33] 陈远童(Chen Y T). 微生物学通报(Microbiology China), 2000, 27: 309.
[34] van Dam P B, Boelhouwer C, Mittelmeijer M C. J. Chem. Soc. Chem. Commun., 1972, 1221.
[35] Vandam P B, Mittelmeijer M C, Boelhouwer C. J. Am. Oil Chem. Soc., 1974, 51: 389.
[36] Verkuijlen E, Kapteijn F, Mol J C, Boelhouwer C. J. Chem. Soc. Chem. Commun., 1977, 198.
[37] Schwab P, France M B, Ziller J W, Grubbs R H. Angew. Chem. Int. Ed., 1995, 34: 2039.
[38] Schwab P, Grubbs R H, Ziller J W. J. Am. Chem. Soc., 1996, 118: 100.
[39] Vougioukalakis G C, Grubbs R H. Chem. Rev., 2010, 110: 1746.
[40] Scholl M, Ding S, Lee C W, Grubbs R H. Org. Lett., 1999, 1: 953.
[41] Garber S B, Kingsbury J S, Gray B L, Hoveyda A H. J. Am. Chem. Soc., 2000, 122: 8168.
[42] Grubbs R H, Nguyen S T. US 5728917A, 1998.
[43] Vilela C, Silvestre A J D, Meier M A R. Macromol. Chem. Phys., 2012, 213: 2220.
[44] Ngo H L, Jones K, Foglia T A. J. Am. Oil Chem. Soc., 2006, 83: 629.
[45] Ngo H L, Foglia T A. J. Am. Oil Chem. Soc., 2007, 84: 777.
[46] Schmidt B. Eur. J. Org. Chem., 2004, 1865.
[47] Schmidt B. J. Mol. Catal. A: Chem., 2006, 254: 53.
[48] Dinger M B, Mol J C. Organometallics, 2003, 22: 1089.
[49] Dinger M B, Mol J C. Eur. J. Inorg. Chem., 2003, 2827.
[50] Hong S H, Day M W, Grubbs R H. J. Am. Chem. Soc., 2004, 126: 7414.
[51] Djigoue G B, Meier M A R. Appl. Catal. A: Gen., 2009, 368: 158.
[52] Hong S H, Sanders D P, Lee C W, Grubbs R H. J. Am. Chem. Soc., 2005, 127: 17160.
[53] Meyer W H, McConnell A E, Forman G S, Dwyer C L, Kirk M M, Ngidi E L, Blignaut A, Saku D, Slawin A M Z. Inorg. Chim. Acta, 2006, 359: 2910.
[54] Gimeno N, Formentin P, Steinke J H G, Vilar R. Eur. J. Org. Chem., 2007, 918.
[55] Trzaskowski J, Quinzler D, Bahrle C, Mecking S. Macromol. Rapid Commun., 2011, 32: 1352.
[56] Fang H, Zhao C, Kong Q, Zou Z, Chen N. Energy, 2016, 116, 177.
[57] Zhao C, Fang H, Chen S. Biotechnol. Biofuels, 2017, 10: 202.
[58] Goldbach V, Falivene L, Caporaso L, Cavallo L, Mecking S. ACS Catal., 2016, 6: 8229.
[59] Reed S F. J. Polym. Sci. Part A: Polym. Chem., 1971, 9: 2147.
[60] Kanakavel M. Makromol. Chem. Macromol. Chem. Phys., 1987, 188: 845.
[61] Schnecko H, Degler G, Dongowski H, Caspary R, Angerer G, Ng T S. Angew. Makromol. Chem., 1978, 70: 9.
[62] Xu J T, Dimonie V L, Sudol E D, Elaasser M S. J. Polym. Sci. Part A: Polym. Chem., 1995, 33: 1353.
[63] German I, Kelhifi W, Norsic S, Boisson C, D’Agosto F. Angew. Chem. Int. Ed., 2013, 52: 3438.
[64] Norsic S, Thomas C, D’Agosto F, Boisson C. Angew. Chem. Int. Ed., 2015, 54: 4631.
[65] Pitet L M, Zhang J, Hillmyer M A. Dalton Trans., 2013, 42: 9079.
[66] Bielawski C W, Grubbs R H. Prog. Polym. Sci., 2007, 32: 1.
[67] Tasdelen M A, Kahveci M U, Yagci Y. Prog. Polym. Sci., 2011, 36: 455.
[68] 冯雨晨(Feng Y C), 介素云(Jie S Y), 李伯耿(Li B G). 化学进展(Progress in Chemistry), 2015, 27: 1074.
[69] Pitet L M, Hillmyer M A. Macromolecules, 2011, 44: 2378.
[70] Carothers W H. Trans. Faraday Soc., 1936, 32: 0039.
[71] Stempfle F, Ortmann P, Mecking S. Macromol. Rapid Commun., 2013, 34: 47.
[72] Mutlu H, Hofsass R, Montenegro R E, Meier M A R. RSC Adv., 2013, 3: 4927.
[73] Quinzler D, Mecking S. Angew. Chem. Int. Ed., 2010, 49: 4306.
[74] Roesle P, Stempfle F, Hess S K, Zimmerer J, Bartulos C R, Lepetit B, Eckert A, Kroth P G, Mecking S. Angew. Chem. Int. Ed., 2014, 53: 6800.
[75] Korshak W V, Vinogradova S V. Bull. Acad. Sci. USSR Div. Chem. Sci., 1953, 2: 995.
[76] Fuller C S, Frosch C J. J. Am. Chem. Soc., 1939, 61: 2575.
[77] Bunn C W. J. Polym. Sci., 1955, 16: 323.
[78] Rickert S E, Baer E, Wittmann J C, Kovacs A J. J. Polym. Sci., Polym. Phys. Ed., 1978, 16: 895.
[79] Jimenez-Rodriguez C, Eastham G R, Cole-Hamilton D J. Inorg. Chem. Commun., 2005, 8: 878.
[80] Okumura S, Iwai M, Tominaga Y. Agric. Biol. Chem., 1984, 48: 2805.
[81] Mahapatro A, Kumar A, Kalra B, Gross R A. Macromolecules, 2004, 37: 35.
[82] Uyama H, Inada K, Kobayashi S. Chem. Lett., 1998, 1285.
[83] Kobayashi S, Uyama H, Suda S, Namekawa S. Chem. Lett., 1997, 105.
[84] Kobayashi S, Uyama H, Namekawa S. Polym. Degrad. Stabil., 1998, 59: 195.
[85] Biggs B S, Frosch C J, Erickson R H. Ind. Eng. Chem., 1946, 38: 1016.
[86] Aharoni S M. n-Nylons: Their Synthesis, Structure and Properties. Wiley-VCH: Weinheim, 1997.
[87] Bennett C, Mathias L J. J. Polym. Sci. Part A: Polym. Chem., 2005, 43: 936.
[88] Bennett C, Zeng J, Kumar S, Mathias L J. J. Appl. Polym. Sci., 2006, 99: 2062.
[89] Nataniel T, Heinrich D. US 7163996B2, 2007.
[90] Nataniel T, Heinrich D. US 8119251B2, 2012.
[91] Gavenois J, Mathew A K. US 0052384, 2013.
[92] Coffman D D, Berchet G J, Peterson W R, Spanagel E W. J. Polym. Sci., 1947, 2: 306.
[93] Cui X W, Li W H, Yan D Y, Yuan C M, di Silvestro G. J. Appl. Polym. Sci., 2005, 98: 1565.
[94] Huang Y, Li W H, Yan D Y. Polym. Bull., 2002, 49: 111.
[95] Ehrenstein M, Dellsperger S, Kocher C, Stutzmann N, Weder C, Smith P. Polymer, 2000, 41: 3531.
[96] Ehrenstein M, Smith P, Weder C. Macromol. Chem. Phys., 2003, 204: 1599.
[97] Saotome K, Komoto H. J. Polym. Sci. Part A: Polym. Chem., 1966, 4: 1463.
[98] Bennett C, Kaya E, Sikes A M, Jarrett W L, Mathias L J. J. Polym. Sci. Part A: Polym. Chem., 2009, 47: 4409.