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Poly(3-Hydroxybutyrate) from Carbon Monoxide

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Synthetic Biodegradable Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 245))

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Abbreviations

β-BL:

β-Butyrolactone

γ-BL:

γ-Butyrolactone

3-HB:

3-Hydroxybutyrate

3-HV:

3-Hydroxyvaleriate

AACS:

Acetoacetyl-CoA synthetase

ADP:

Adenosine diphosphate

AMP:

Adenosine monophosphate

ATP:

Adenosine triphosphate

ATR:

Attenuated total reflection

Bdh1:

3-Hydroxybutyric acid dehydrogenase

BDI:

2-[(2,6-Dialkylphenyl)amido]-4-[(2,6-dialkylphenyl)imino]-2-pentene

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphtyl

DFT:

Density functional theory

DSC:

Differential scanning calorimetry

ee:

Enantiomeric excess

FAD:

Flavin adenine dinucleotide (oxidized species)

FADH2 :

Flavin adenine dinucleotide (reduced species)

HDPE:

High density poly(ethylene)

HPPO:

Hydrogen peroxide to propylene oxide

LA:

Lewis acid

LDPE:

Low density poly(ethylene)

M n :

Number-average molecular weight

M w :

Weight-average molecular weight

NAD+ :

Nicotinamide adenine dinucleotide (oxidized species)

NADH:

Nicotinamide adenine dinucleotide (reduced species)

NMR:

Nuclear magnetic resonance

PBS:

Poly(butylene succinate)

PC:

Poly(carbonate)

PD:

Polydispersity

PE:

Poly(ethylene)

PET:

Poly(ethyleneterephtalate)

PHA:

Poly(3-hydroxyalkanoate)

PhaZ:

Poly(3-hydroxybutyrate) depolymerase

PhaZc:

Hydroxybutyrate-dimer hydrolase

PHB:

Poly(3-hydroxybutyrate)

PhbA:

β-Ketothiolase

PhbB:

Acetoacetyl-CoA reductase

PhbC:

Poly(3-hydroxybutyrate) synthase

PLA:

Poly(lactic acid)

PO:

Propylene oxide

PP:

Poly(propylene)

PS:

Polystyrene

ROP:

Ring opening polymerization

THF:

Tetrahydrofuran

TIBAO:

Tetraisobutyldialuminoxane

References

  1. Lendlein A (1999) Chemie in Unserer Zeit 33:279

    CAS  Google Scholar 

  2. Van der Walle GAM, De Koning GJM, Weusthuis RA, Eggink G (2001) Adv Biochem Eng Biotechnol 71:263

    Google Scholar 

  3. Breulmann M, Künkel A, Philipp S, Reimer V, Siegenthaler KO, Skupin G, Yamamoto M (2009) Polymers, Biodegradable. In: Ullmann's encyclopedia of industrial chemistry Wiley-VCH, Weinheim, doi:10.1002/14356007.n21_n01

    Google Scholar 

  4. Scandola M, Ceccorulli G, Doi Y (1990) Int J Biol Macromol 12:112

    CAS  Google Scholar 

  5. Scandola M, Ceccorulli G, Pizzoli M (1989) Makromol Chem Rapid Commun 10:47

    CAS  Google Scholar 

  6. Holmes P (1988) Biologically produced (R)-3-hydroxyalkanoate polymers and copolymers. Elsevier, London

    Google Scholar 

  7. Doi Y (1990) Microbial polyesters. VCH-Publishers, New York

    Google Scholar 

  8. Wallen LL, Rohwedder WK (1974) Environ Sci Technol 8:576

    CAS  Google Scholar 

  9. Abe H, Matsubara I, Doi Y, Hori Y, Yamaguchi A (1994) Macromolecules 27:6018

    CAS  Google Scholar 

  10. Tanahashi N, Doi Y (1991) Macromolecules 24:5732

    CAS  Google Scholar 

  11. Kricheldorf HR, Eggerstedt S (1997) Macromolecules 30:5693

    CAS  Google Scholar 

  12. Ajellal N, Bouyahyi M, Amgoune A, Thomas CM, Bondon A, Pillin I, Grohens Y, Carpentier J-F (2009) Macromolecules 42:987

    CAS  Google Scholar 

  13. Zintl M, Molnar F, Urban T, Bernhart V, Preishuber-Pflügl P, Rieger B (2008) Angew Chem Int Ed Engl 47:3458

    CAS  Google Scholar 

  14. Tsuji H, Okumura A (2009) Macromolecules 42:7263

    CAS  Google Scholar 

  15. Fukushima K, Kimura Y (2006) Polym Int 55:626

    CAS  Google Scholar 

  16. Timmins MR, Lenz RW, Hocking PJ, Marchessault RH, Fuller RC (1996) Macromol Chem Phys 197:1193

    CAS  Google Scholar 

  17. Doi Y, Segawa A, Kunioka M (1990) Int J Biol Macromol 12:106

    CAS  Google Scholar 

  18. Hakkarainen M (2002) Adv Polym Sci 157:113

    CAS  Google Scholar 

  19. Luzier WD (1992) Proc Natl Acad Sci USA 89:839

    CAS  Google Scholar 

  20. Nakayama K, Saito T, Fukui T, Shirakura T, Tomita K (1985) Biochim Biophys Acta 827:63

    CAS  Google Scholar 

  21. Tanio T, Fukui T, Shirakura T, Saito T, Tomita K, Kaiho T, Masamune S (1982) Eur J Biochem 124:71

    CAS  Google Scholar 

  22. Brucato CL, Wong SS (1991) Biochim Biophys Acta 290:497

    CAS  Google Scholar 

  23. Kumagai Y, Kanesawa Y, Doi Y (1992) Makromolekulare Chemie 193:53

    CAS  Google Scholar 

  24. Jaimes C, Dobreva-Schue R, Giani-Beaune O, Schue F, Amass W, Amass A (1999) Polym Int 48:23

    CAS  Google Scholar 

  25. Kemnitzer JE, MacCarthy SP, Gross RA (1992) Macromolecules 25:5927

    CAS  Google Scholar 

  26. Hocking J, Marchessault RH, Timmins MR, Scherer TM, Lenz RW, Fuller RC (1994) Macromol Rapid Commun 15:447

    CAS  Google Scholar 

  27. Jesudason JJ, Marchessault RH, Saito T (1993) J Environ Polym Degrad 1:89

    CAS  Google Scholar 

  28. Schue F, Jaimes C, Dobreva-Schue R, Giani-Beaune O, Amass W, Amass A (2000) Polym Int 49:965

    CAS  Google Scholar 

  29. Arcana M, Giani-Beaune O, Schue F, Schue R, Amass W, Amass A (2002) Polym Int 51:859

    CAS  Google Scholar 

  30. Wu B, Lenz RW (1998) Macromolecules 31:3473

    CAS  Google Scholar 

  31. Abe H, Doi Y, Hori Y, Hagiwara T (1997) Polymer 39:59

    Google Scholar 

  32. Hmamouchi M, Lavallee C, Prud'homme RE, Leborgne A, Spassky N (1989) Macromolecules 22:130

    CAS  Google Scholar 

  33. Bloembergen S, Holden DA, Bluhm TL, Hamer GK, Marchessault RH (1989) Macromolecules 22:1656

    CAS  Google Scholar 

  34. Rieth LR, Moore DR, Lobkovsky EB, Coates GW (2002) J Am Chem Soc 124:15239

    CAS  Google Scholar 

  35. de Koning G (1995) Can J Microbiol 41:303

    Google Scholar 

  36. Holmes PA (1985) Phys Technol 16:32

    CAS  Google Scholar 

  37. Schmitt EE, Polistina RA (1967) US Patent Application US1963-320543

    Google Scholar 

  38. Wynne F (1994) In: Marten J (ed) Kunststoffe und nachwachsende Rohstoffe. Landwirtschaftsverlag, Münster-Hiltrup, p 42

    Google Scholar 

  39. Mantelatto PE, Duzzi AM, Sato T, Durao NAS, Nonato RV, Rocchiccioli C, Kesserlingh SM (2005) Patent Application WO2005052175

    Google Scholar 

  40. Berger E, Ramsay BA, Ramsay JA, Chavarie C, Braunegg G (1989) Biotechnol Tech 3:227

    CAS  Google Scholar 

  41. Müller R, Schumann D (2001) Neues chemisch-enzymatisches Aufschlussverfahren (CEA) zur effektiven und schonenden Gewinnung von Biopolymeren aus Biomasse. Umweltforschungszentrum (UFZ), Leipzig-Halle. http://www.ufz.de/data/Cea914.pdf

  42. Niamsiri N, Bergkvist M, Delamarre SC, Cady NC, Coates GW, Ober CK, Batt CA (2007) Colloids Surf B 60:68

    CAS  Google Scholar 

  43. Siegmund F, Veit D, Gries T (2009) Chemie in Unserer Zeit 43:152

    CAS  Google Scholar 

  44. Allmendinger M, Eberhardt R, Luinstra GA, Rieger B (2003) Macromol Chem Phys 204:564

    CAS  Google Scholar 

  45. Seliger H (2005) The ideal mix for turning biosynthetics into competitive products. Bio-Pro, Baden-Würthenberg. http://www.bio-pro.de/biopolymere/artikelliste_biopolymere/index.html?lang=en&artikelid=/artikel/02194/index.html

  46. Braunegg G, Lefebvre G, Genser KF (1998) J Biotechnol 65:127

    CAS  Google Scholar 

  47. European Bioplastics (2008) Bioplastics – frequently asked questions. European Bioplastics, Berlin. http://www.european-bioplastics.org/index.php?id=191

  48. Shen L, Haufe J, Patel MK (2009) Product overview and market projection of emerging bio-based plastics (PRO-BIP 2009). EPNOE, Paris. http://www.epnoe.eu/content/download/7670/109501/file/PROBIP2009%20Final%20June%202009.pdf

  49. Noda I, Lindsey SB, Caraway D (eds) (2010) Nodax™ class PHA copolymers: their properties and applications. In: Microbiology monographs, vol 14. Springer, Heidelberg, pp 237–255

    Google Scholar 

  50. Jin M (2007) Biodegradable plastic PHA and their application. Paper presented at international conference on green materials and green olympics, 27–28 October 2007, Beijing

    Google Scholar 

  51. Chen G-Q (2008) Recent biodegradable plastics development in China. Dept of Biological Sciences and Biotechnology, Beijing

    Google Scholar 

  52. Schneller A (2006) Polymere aus nachwachsenden Rohstoffen – Technische und ökonomische Herausforderungen. BASF SE, Ludwigshafen

    Google Scholar 

  53. Yazdani SS, Gonzalez R (2007) Curr Opin Biotechnol 18:213

    CAS  Google Scholar 

  54. Plotkin JS, Coleman HJ, Coker A, Denye M (2009) Green propylene: process technology (including bioethanol, biobutanol, biodiesel, biomass, and vegetable oil routes) production costs, and regional supply/demand forecasts (PERP07/08S11). Nexant, San Francisco. http://www.chemsystems.com/reports/search/docs/abstracts/0708S11_abs.pdf

  55. Kahlich D, Wiechern U, Lindner J (2002) Propylene oxide. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_239

  56. Fey J, Dean M (2009) New BASF and Dow HPPO plant in Antwerp completes start-up phase. BASF SE, DOW Chemical Company, Ludwigshafen. http://www.dow.com/news/corporate/2009/20090305a.htm

  57. Tullo A (2004) Dow, BASF to build propylene oxide. Chem Eng News 82(36):15

    Google Scholar 

  58. Heck RF, Breslow DS (1961) J Am Chem Soc 83:4022

    CAS  Google Scholar 

  59. Heck RF (1963) J Am Chem Soc 85:1460

    CAS  Google Scholar 

  60. Drent E, Kragtwijk E (1994) Patent Application: EP1993201844

    Google Scholar 

  61. Lee JT, Thomas PJ, Alper H (2001) J Org Chem 66:5424

    CAS  Google Scholar 

  62. Allmendinger M (2004) PhD Thesis. Multi-Site Catalysis - Novel Strategies to Biodegradable Polyesters from Epoxides/CO and Macrocyclic Complexes as Enzyme Models. Universität Ulm, Ulm

    Google Scholar 

  63. Allmendinger M, Eberhardt R, Luinstra G, Rieger B (2002) J Am Chem Soc 124:5646

    CAS  Google Scholar 

  64. Allmendinger M, Zintl M, Eberhardt R, Luinstra GA, Molnar F, Rieger B (2004) J Organomet Chem 689:971

    CAS  Google Scholar 

  65. Allmendinger M, Molnar F, Zintl M, Luinstra GA, Preishuber-Pfluegl P, Rieger B (2005) Chem –Eur J 11:5327

    CAS  Google Scholar 

  66. Bergman RG (1980) Acc Chem Res 13:113

    CAS  Google Scholar 

  67. Wender I, Pino P (eds) (1977) Organic synthesis via metal carbonyls, vol 2. Wiley, New York

    Google Scholar 

  68. Marchessault RH, Okamura K, Su CJ (1970) Macromolecules 3:735

    CAS  Google Scholar 

  69. Lee JT, Alper H (2004) Macromolecules 37:2417

    CAS  Google Scholar 

  70. Loefgren A, Albertsson A-C, Dubois P, Jerome R (1995) J Macromol Sci, Rev Macromol Chem Phys C35:379

    CAS  Google Scholar 

  71. Coulembier O, Dubois P (2009) In: Dubois P, Coulembier O, Raquez J-M (eds) Handbook of ring-opening polymerization. Wiley, Weinheim, p 227

    Google Scholar 

  72. Ajellal N, Thomas CM, Carpentier J-F (2009) J Polym Sci Part A Polym Chem 47:3177

    CAS  Google Scholar 

  73. Carpentier J-F, Helou M, Guillaume S, Razavi A (2010) Patent Application WO153:62758

    Google Scholar 

  74. Jaimes C, Arcana M, Brethon A, Mathieu A, Schue F, Desimone JM (1998) Eur Polym J 34:175

    CAS  Google Scholar 

  75. Takeichi T, Hieda Y, Takayama Y (1988) Polym J (Tokyo) 20:159

    CAS  Google Scholar 

  76. Asano S, Aida T, Inoue S (1985) Macromolecules 18:2057

    CAS  Google Scholar 

  77. Spassky N, Pluta C, Simic V, Thiam M, Wisniewski M (1998) Macromol Symp 128:39

    CAS  Google Scholar 

  78. Le Borgne A, Spassky N (1989) Polymer 30:2312

    Google Scholar 

  79. Guillaume C, Carpentier J-F, Guillaume SM (2009) Polymer 50:5909

    CAS  Google Scholar 

  80. Kemnitzer JE, McCarthy SP, Gross RA (1993) Macromolecules 26:1221

    CAS  Google Scholar 

  81. Kemnitzer JE, McCarthy SP, Gross RA (1993) Macromolecules 26:6143

    CAS  Google Scholar 

  82. Arcana M, Giani-Beaune O, Schue F, Amass W, Amass A (2000) Polym Int 49:1348

    CAS  Google Scholar 

  83. Jedlinski Z, Kowalczuk M, Kurcok P, Adamus G, Matuszowicz A, Sikorska W, Gross RA, Xu J, Lenz RW (1996) Macromolecules 29:3773

    CAS  Google Scholar 

  84. Kricheldorf HR, Lee S-R, Scharnagl N (1994) Macromolecules 27:3139

    CAS  Google Scholar 

  85. Hori Y, Suzuki M, Yamaguchi A, Nishishita T (1993) Macromolecules 26:5533

    CAS  Google Scholar 

  86. Hori Y, Hagiwara T (1999) Int J Biol Macromol 25:237

    CAS  Google Scholar 

  87. Carpentier J-F (2010) Macromol Rapid Commun 31:1696

    CAS  Google Scholar 

  88. Le Borgne A, Pluta C, Spassky N (1994) Macromol Rapid Commun 15:955

    Google Scholar 

  89. Amgoune A, Thomas CM, Ilinca S, Roisnel T, Carpentier J-F (2006) Angew Chem Int Ed Engl 45:2782

    CAS  Google Scholar 

  90. Grunova E, Kirillov E, Roisnel T, Carpentier J-F (2010) Dalton Trans 39:6739

    CAS  Google Scholar 

  91. Ajellal N, Lyubov DM, Sinenkov MA, Fukin GK, Cherkasov AV, Thomas CM, Carpentier J-F, Trifonov AA (2008) Chem Eur J 14:5440

    CAS  Google Scholar 

  92. Chamberlain BM, Cheng M, Moore DR, Ovitt TM, Lobkovsky EB, Coates GW (2001) J Am Chem Soc 123:3229

    CAS  Google Scholar 

  93. Ajellal N, Durieux G, Delevoye L, Tricot G, Dujardin C, Thomas CM, Gauvin RM (2010) Chem Commun 46:1032

    CAS  Google Scholar 

  94. Reichardt R, Vagin S, Reithmeier R, Ott AK, Rieger B (2010) Macromolecules 43:9311

    CAS  Google Scholar 

  95. Luinstra GA, Haas GR, Molnar F, Bernhart V, Eberhardt R, Rieger B (2005) Chem – Eur J 11:6298

    CAS  Google Scholar 

  96. Darensbourg DJ (2007) Chem Rev 107:2388

    CAS  Google Scholar 

  97. Luinstra GA (2008) Polym Rev 48:192

    CAS  Google Scholar 

  98. Klaus S, Lehenmeier MW, Anderson CE, Rieger B (2011) Coord Chem Rev 255:1460–1479

    Google Scholar 

  99. Hansen KB, Leighton JL, Jacobsen EN (1996) J Am Chem Soc 118:10924

    CAS  Google Scholar 

  100. Jacobsen EN, Tokunaga M, Larrow JF (2000) Patent Application WO200009463

    Google Scholar 

  101. Yoon TP, Jacobsen EN (2003) Science 299:1691

    CAS  Google Scholar 

  102. Vagin SI, Reichardt R, Klaus S, Rieger B (2010) J Am Chem Soc 132:14367

    CAS  Google Scholar 

  103. Zintl M (2010) PhD Thesis. Stereoselektive Herstellung von Poly(hydroxybutyrat): Teilisotaktische Polymere durch gezieltes Katalysatordesign. University Ulm, Ulm

    Google Scholar 

  104. Nakano K, Kamada T, Nozaki K (2006) Angew Chem Int Ed 45:7274

    CAS  Google Scholar 

  105. Ren W-M, Zhang X, Liu Y, Li J-F, Wang H, Lu X-B (2010) Macromolecules 43:1396

    CAS  Google Scholar 

  106. Sujith S, Min JK, Seong JE, Na SJ, Lee BY (2008) Angew Chem Int Ed 47:7306

    CAS  Google Scholar 

  107. Kricheldorf HR, Berl M, Scharnagl N (1988) Macromolecules 21:286

    CAS  Google Scholar 

  108. Shelton JR, Agostini DE, Lando JB (1971) J Polym Sci A-1 Polym Chem 9:2789

    CAS  Google Scholar 

  109. Seebach D, Roggo S, Zimmermann J (1987) In: Bartmann W, Sharpless KB (eds) Stereochemistry of organic and bioorganic transformations: Proceedings 17th Workshop Conference Hoechst, October 1986. VCH, Weinheim, p 85

    Google Scholar 

  110. Capozzi G, Roelens S, Talami S (1993) J Org Chem 58:7932

    CAS  Google Scholar 

  111. Klabunovskii EI, Sheldon RA (1997) Cattech 1:153 and references cited in

    CAS  Google Scholar 

  112. Vollhardt KPC, Schore NE (2000) Organische Chemie. Wiley-VCH, Weinheim

    Google Scholar 

  113. Church TL, Getzler YDYL, Byrne CM, Coates GW (2007) Chem Commun 657

    Google Scholar 

  114. Getzler YDYL, Mahadevan V, Lobkovsky EB, Coates GW (2002) J Am Chem Soc 124:1174

    CAS  Google Scholar 

  115. Kramer JW, Lobkovsky EB, Coates GW (2006) Org Lett 8:3709

    CAS  Google Scholar 

  116. Getzler YDYL, Mahadevan V, Lobkovsky EB, Coates GW (2004) Pure Appl Chem 76:557

    CAS  Google Scholar 

  117. Mahadevan V, Getzler YDYL, Coates GW (2002) Angew Chem Int Ed Engl 41:2781

    CAS  Google Scholar 

  118. Allmendinger M, Eberhardt R, Luinstra GA, Molnar F, Rieger B (2003) Z Anorg Allg Chem 629:1347

    CAS  Google Scholar 

  119. Kagan HB, Fiaud JC (1988) Topics Stereochem 18:249

    CAS  Google Scholar 

  120. Eliel EL, Wilen SH, Mander LN (1994) Stereochemisty of organic compounds. Wiley, New York

    Google Scholar 

  121. Martinez LE, Leighton JL, Carsten DH, Jacobsen EN (1995) J Am Chem Soc 117:5897

    CAS  Google Scholar 

  122. Larrow JF, Schaus SE, Jacobsen EN (1996) J Am Chem Soc 118:7420

    CAS  Google Scholar 

  123. Schaus SE, Jacobsen EN (1996) Tetrahedron Lett 37:7937

    CAS  Google Scholar 

  124. Schaus SE, Larrow JF, Jacobsen EN (1997) J Org Chem 62:4197

    CAS  Google Scholar 

  125. Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN (1997) Science 277:936

    CAS  Google Scholar 

  126. Schaus SE, Jacobsen EN (2000) Org Lett 2:1001

    CAS  Google Scholar 

  127. Jacobsen EN (2000) Acc Chem Res 33:421

    CAS  Google Scholar 

  128. Brandes BD, Jacobsen EN (2001) Synlett 1013

    Google Scholar 

  129. Li Z, Fernandez M, Jacobsen EN (1999) Org Lett 1:1611

    CAS  Google Scholar 

  130. Urban T (2007) PhD Thesis. Neue chirale Katalysatorsysteme zur Synthese von enantiomerenangereichertem beta-Butyrolacton aus Propylenoxid und CO. Universität Ulm, Ulm

    Google Scholar 

  131. Woelfle H, Kopacka H, Wurst K, Preishuber-Pfluegl P, Bildstein B (2009) J Organomet Chem 694:2493

    CAS  Google Scholar 

  132. Dunn EW, Coates GW (2010) J Am Chem Soc 132:11412

    CAS  Google Scholar 

  133. Reimer V, Kuenkel A, Philipp S (2008) Kunststoffe 98:32

    CAS  Google Scholar 

  134. Zhang Y, Gross RA, Lenz RW (1990) Macromolecules 23:3206–3212

    Google Scholar 

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Acknowledgement

Special thanks to Urs J. Haenggi (Biomer) for information about biotechnological PHB synthesis and literature on stereocomplex formation of poly(lactide). We are also grateful to Dr. Carly Anderson and Dr. Sergei Vagin for their help with this article, as well as Benedikt Simon Soller and Simon Meister for their extensive help with the literature research.

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Reichardt, R., Rieger, B. (2011). Poly(3-Hydroxybutyrate) from Carbon Monoxide. In: Rieger, B., Künkel, A., Coates, G., Reichardt, R., Dinjus, E., Zevaco, T. (eds) Synthetic Biodegradable Polymers. Advances in Polymer Science, vol 245. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2011_127

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