Abstract
Poly(trimethylene terephthalate) (PTT) fibers, as a new type of polyester, are characterized by much better resilience and stress/recovery properties than poly(ethylene terephthalate) (PET) and poly(butylene terephthalate) (PBT). PPT chains are much more angularly structured than PET and PBT chains and such chains can be stretched by up to 15% with a reversible recovery (Ward et al. 1976).These properties make PTT highly suitable for uses in fiber, carpet, textile, film, and engineering thermoplastics applications. 1,3-Propanediol (PDO), as one of the polyester raw materials for PTT, has also attracted interest.
In the 1990s three technical processes for the production of PDO were developed. The first process used acrolein, and was developed by Degussa-Hüls; this technology was sold to DuPont in 1997. The second was developed by Shell with ethylene oxide as the substrate. These two processes are all classic chemical processes. Recently, the biological process of PDO production with glycerol or glucose as raw materials in one or two steps has been considered as a competitor to the traditional petrochemical routes. It has advantages such as mild reaction conditions, good selectivity of product, environmental friendliness, and use of a renewable feedstock. With the development of biotechnology, especially gene manipulation technology, microbial PDO has prospects for the production of PTT.
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References
Arntz D, Haas T, Muller A, Wiegand N (1991) Kinetische untersuchung zur hydratisierung von acrolein. Chem Ing Tech 63:733–735
Abbad Andaloussi S, Manginot Durr C, Amine J, Petitdemange E, Petitdemange H (1995) Isolation and characterization of Clostridium butyricum DSM 5431 mutants with increased resistance to PDO and altered production of acids. Appl Environ Microbiol 61:4413–4417
Abbad Andaloussi S, Guedon E, Spiesser E (1996) Glycerol dehydratase activity: the limiting step for PDO production by Clostridium butyricum. Lett Appl Microbiol 22:311–314
Adkesson DM, Alsop AW, Ames TT, Chu LA, Disney JM, Dravis BC, Fitzgibbon P, Gaddy JM, Gallagher FG, Lehnhardt WF, Lievense JC, Luyben ML, Seapan M, Trotter RE, Wenndt GM, Yu EK (2005) Purification of biologically-produced 1,3-propanediol. US Patent 20,050,069,997
Ahrens K, Menzel K, Zeng AP (1998) Kinetic, dynamic, and pathway studies of glycerol metabolism by Klebsiella pneumoniae in anaerobic continuous culture: Ш Enzymes and fluxes of glycerol dissimilation and PDO formation. Biotechnol Bioeng 59:544–552
Ames TT (2002) Process for the isolation of PDO from fermentation broth. US Patent 6,361,983 B1
Barbirato F, Camarasa-Claret C, Grivet JP, Bories A (1995) Glycerol fermentation by a new PDO producing microorganism: Enterobacter agglomerans. Appl Microbiol Biotechnol 43:786–793
Barbirato F, Himmi HE, Conte T, Bories A (1998) PDO production by fermentation: an interesting way to valorize glycerin from the ester and ethanol industries. Ind Crops Prod 7:281–289
Biebl H, Marten S (1995) Fermentation of glycerol to 1,3-propanediol: use of cosubstrates. Appl Microbiol Biotechnol 44:15–19
Biebl H, Menzel K, Zeng AP (1999) Microbial production of 1,3-propanediol. Appl Microbiol Biotechnol 52:289–297
Boenigk R, Bowien S, Gottschalk G (1993) Fermentation of glycerol to PDO in continuous cultures of Citrobacter freundii. Appl Microbiol Biotechnol 38:453–457
Cameron DC, Altaras NE, Hoffman ML (1998) Metabolic engineering of propanediol pathways. Biotechnol Progr 14(116):125
Carr PL, Jakeways R, Klein JL, Ward IM (1997) Tensile drawing, morphology, and mechanical properties of poly(butylene terephthalate). J Polym Sci Part B Polym Phys 35:2465–2481
Chen X, Xiu ZL, Wang JF, Zhang DJ, Xu P (2003) Stoichiometric analysis and experimental investigation of glycerol bioconversion to PDO by Klebsiella pneumoniae under microaerobic conditions. Enzyme Microb Technol 33:386–394
Cheng KK, Liu DH, Sun Y, Liu WB (2004) PDO production by Klebsiella pneumoniae under different aeration strategies. Biotechnol Lett 26:911–915
Cho M-H, Joen SI, Pyo S-H, Mun S, Kim J-H (2006) A novel separation and purification process for 1,3-propanediol. Process Biochem 41(3):739–744
Daniel R, Gottschalk G (1992) Growth temperature-dependent activity of glycerol dehydratase in Escherichia coli expressing the Citrobacter freundii regulon. FEMS Microbiol Lett 100:281–286
Daubert TE, Danner RP (1989) Physical and thermodynamic properties of pure chemicals: data Compilation. Taylor & Francis, Washington
Dupeuble JC (2001) Technologies for the PBT, PTT and PET supply chain. Chem Fibers Int 51(1):43–44
Forage RG, Lin ECC (1982) dha systems mediating aerobic and anaerobic dissimilation of glycerol in Klebsiella pneumoniae NCIB 418. J Bacteriol 151:591–599
Forsberg CW (1987) Production of 1,3-propanediol from glycerol by Clostridium acetobutylicum and other Clostridium species. Appl Environ Microbiol 53:639–643
Gong Y, Tong Y, Wang XL, Liu DH (2004) The possibility of the desalination of actual PDO fermentation broth by electrodialysis. Desalination 161:169–178
Günzel B, Yonsel S, Deckwer WD (1991) Fermentative production of PDO from glycerol by Clostridium butyricum up to a scale of 2m3. Appl Microbiol Biotechnol 36(289):295
Liu HJ, Zhang DJ, Xu YH, Mu Y, Sun YQ, Xiu ZL (2007) Microbial production of PDO from glycerol by Klebsiella pneumoniae under micro-aerobic conditions up to a pilot scale. Biotechnol Lett 29:1281–1285
Hao J, Liu HJ, Liu DH (2005) Novel route of reactive extraction to recover PDO from a dilute aqueous solution. Ind Eng Chem Res 44:4380–4385
Hao J, Xu F, Liu H, Liu DH (2006) Downstream processing of 1,3-propanediol fermentation broth. J Chem Technol Biotechnol 81:102–108
Haynie SL, Wagner LW (1996) Converting L-sorbose to 2-keto-L-gulonic acid by fermentation|from carbon substrates using mixed culture of glycerol-producing and diol-producing organisms. E I du Pont de Nemours & Co WO 9635799-A
Hu JL, Lu J, Zhu Y (2008) New developments in elastic fibers. Polym Rev 48(2):275–301
Huang H, Gong CS, Tsao GT (2002) Production of PDO by Klebsiella pneumonia. Appl Microbiol Biotechnol 99:687–698
Kurian JV (2005) A new polymer platform for the future—Sorona from corn derived 1,3-propanediol. J Polym Environ 13(2):159–167
Kathiervelu S (2002) Polytrimethylene terephthalate (PTT) fibres. Synth Fibres 31(4):11–12
Koch JP, Hayashi S, Lin ECC (1964) The control of the dissimilation of glycerol and L-a-glycerolphosphate in Escherichia coli. J Biol Chem 239:3106–3108
Laffend LA, Nagarajan V, Nakamura CE (1997) Bioconversion of a fermentable carbon source to PDO by a single microorganism. US Patent 5,686,276
Malaoui H, Marczak R (2001) Influence of glucose on glycerol metabolism by wild-type and mutant strains of Clostridium butyricum E5 grown in chemostat culture. Appl Microbiol Biotechnol 55:226–233
Malinowski JJ (1999) Evaluation of liquid extraction potentials for downstream separation of 1,3-propanediol. Biotechnol Tech 13:127–130
Malinowski JJ (2000) Reactive extraction for downstream separation of 1,3-propanediol. Biotechnol Progr 16:76–79
Malshe VC, Mandlecha MVK (2000) Production of butane 1,3-diol, propane 1,3-diol and other diols and polyols. Patent WO/2000/056688
Menzel K, Zeng AP, Deckwer WD (1997) High concentration and productivity of PDO from continuous fermentation of glycerol by Klebsiella pneumoniae. Enzyme Microbiol Technol 20(82):86
Nakamura CE, Whited GM (2003) Metabolic engineering for the microbial production of 1,3-propanediol. Curr Opin Biotechnol 14:454–459
Papanikolaou S, Ruiz-Sanchez P, Pariset B, Blanchard F, Fick M (2000) High production of PDO from industrial glycerol by a newly isolated Clostridium butyricum strain. J Biotechnol 77:191–208
Roturier JM, Fouache C, Berghmans E (2002) Process for the purification of PDO from a fermentation medium. US Patent 6,428,992
Ruch FE, Lin ECC (1975) Independent constitutive expression of the aerobic and anaerobic pathways of glycerol catabolism in Klebsiella aerogenes. J Bacterol 124:348–362
Sanz MT, Blanco B, Beltran S, Cabezas JI (2001) Vapor liquid equilibria of binary and ternary systems with water, 1,3-propanediol, and glycerol. J Chem Eng Data 46:635–639
Schutz H, Radler F (1984) Anaerobic reduction of glycerol to PDO by Lactobacillus brevis and Lactobacillus buchneri. Syst Appl Microbiol 5:169–178
Seyfried M, Daniel R, Gottschalk G (1996) Cloning, sequencing and overexpression of the genes encoding Coenzyme B12-dependent glycerol dehydratase of Citrobacter freundii. J Bacteriol 178:5793–5796
Slaugh LH, Powell, JB, Forschner TC, Semple TC, Weider PR (1995) Process for preparing 1,3-propanediol. US Patent 5,463,346
Slaugh LH, Weider PR, Powell, JB (2001) Process for preparing alkanediols. US Patent 6,180,838
Sprenger GA, Hammer GA, Johnson EA, Lin ECC (1989) Anaerobic growth of Escherichia coli on glycerol by importing genes of the dha regulon from Klebsiella pneumoniae. J Gen Microbiol 135:1255–1262
Tobimatsu T, Azuma M, Matsubara H, Tskatori H, Niida T, Nishimoto K, Satoh H, Hayashi R, Toraya T (1996) Cloning, sequencing, and high level expression of the genes encoding adenosylcobalamin-dependent glycerol-dehydratase of Klebsiella pneumoniae. J Biol Chem 271:22352–22357
Tong IT, Liao HH, Cameron DC (1991) PDO production by Escherichia coli expresing genes from the Klebsiella pneumoniae dha regulon. Appl Environ Microbiol 57:3541–3546
Wang JF, Xiu ZL, Liu HJ, Fan SD (2001) Study on microaerobic conversion of glycerin to PDO by Klebsiella pneumoniae. Mod Chem Ind 21(5):28–31
Wang K, Martin CH, Scott JD (2003) Conversion of glycerol to PDO via selective dehydroxylation. Ind Eng Chem Res 42:2813–2923
Ward IM, Wilding MA, Brody H (1976) Mechanical-Properties and structure of poly(meta-methylene terephthalate) Fibers. J. Poly. Sci., Pol. Phy. 14:263–274
Wilkins AE, Lowe DJ (2004) Product removal process for use in a biofermentation system. US Patent 6,812,000
Xu YZ, Liu HJ, Du W, Sun Y, Ou XJ, Liu DH (2009) Integrated production for biodiesel and 1,3-propanediol with lipase-catalyzed transesterification and fermentation. Biotechnol Lett 31(9):1335–1341
Yonenaga A (2000) PTT fibre—a new textile mass product. Int Text Bull 46(5):35–36
Yuan GZ, Tian J, Xu LG, Tang P, Cui DB, Xu GW (2006) Fermentative production of PDO from glycerol by Aspergillus. Food Ferment Ind 32(1):49–52
Zeng AP, Bieb H (2002) Bulk chemicals from biotechnology: the case of PDO production and the new trends. Adv Biochem Eng Biotechnol 74:239–259
Zeng AP, Ross A, Biebl H, Tag C, Gunzel B, Deckw WD (1994) Multiple product inhibition and growth modeling of Clostridium butyricum and Klebsiella pneumoniae in glycerol fermentation. Biotechnol Bioeng 44:902–911
Zheng ZM, Cheng KK, Hu QL, Liu HJ, Guo NN, Liu DH (2008) Effect of culture conditions on 3-hydroxypropionaldehyde detoxification in PDO fermentation by Klebsiella pneumoniae. Biochem Eng J 39:305–310
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Liu, H., Ou, X., Zhou, S., Liu, D. (2010). Microbial 1,3-Propanediol, Its Copolymerization with Terephthalate, and Applications. In: Chen, GQ. (eds) Plastics from Bacteria. Microbiology Monographs, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-03287-5_16
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DOI: https://doi.org/10.1007/978-3-642-03287-5_16
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