Recent developments in catalytic activation of renewable resources for polymer synthesis

Topics in Organometallic Chemistry

Volumn 39, Issue , 2012, Pages 175-224

  Buchard, Antoine ^a   Bakewell, Clare M ^a   Weiner, Jonathan ^a   Williams, Charlotte K ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Carbon dioxide and epoxides copolymerization; Group 13 metal catalysts; Group 3 metal catalysts; Lactide polymerization; Polycarbonate; Polylactide

Indexed keywords

EID: 84863210752     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-28288-1_5     Document Type: Review

References (172)

1. Ragauskas AJ, Williams CK, Davison BH, Britovsek G, Cairney J, Eckert CA, Frederick WJ Jr, Hallett JP, Leak DJ, Liotta CL, Mielenz JR, Murphy R, Templer R, Tschaplinski T (2006) Science 311:484-489
2. Blaker JJ, Lee K-Y, Bismarck A (2011) J Biobased Mater Bioenergy 5:1-16
3. Gandini A (2008) Macromolecules 41:9491-9504
4. Coates GW, Hillmyer MA (2009) Macromolecules 42:7987-7989
5. Gandini A (2010) Polym Chem 1:245-251
6. Gandini A (2011) Green Chem 13:1061-1083
7. Gross RA, Kalra B (2002) Science 297:803-807
8. Williams CK, Hillmyer MA (2008) Polym Rev 48:1-10
9. Avella M, Martuscelli E, Raimo M (2000) J Mater Sci 35:523-545
10. Drumright RE, Gruber PR, Henton DE (2000) Adv Mater 12:1841-1846
11. Amass W, Amass A, Tighe B (1998) Polym Int 47:89-144
12. Inkinen S, Hakkarainen M, Albertsson A-C, Södergård A (2011) Biomacromolecules 12:523-532
13. Williams CK (2007) Chem Soc Rev 36:1573-1580
14. Lindblad M, Liu Y, Albertsson A-C, Ranucci E, Karlsson S (2002) Polymers from renewable resources. In: Degradable aliphatic polyesters, vol. 157. Springer, Berlin, pp 139-161
15. Biermann U, Bornscheuer U, Meier MAR, Metzger JO, Schäfer HJ (2011) Angew Chem Int Ed 50:3854-3871
16. Xia Y, Larock RC (2010) Green Chem 12:1893-1909
17. Auras R, Harte B, Selke S (2004) Macromol Biosci 4:835-864
18. Inoue S, Koinuma H, Tsuruta T (1969) J Polym Sci B Polym Lett 7:287-292
19. Platel RH, Hodgson LM, Williams CK (2008) Polym Rev 48:11-63
20. Duda A Penczek S (2001) Thermodynamics, kinetics, and mechanisms of cyclic esters polymerization. In: Polymers from renewable resources, vol 764. American Chemical Society, pp 160-198
21. Ovitt TM, Coates GW (2002) J Am Chem Soc 124:1316-1326
22. Barakat I, Dubois P, Jérôme R, Teyssié P (1993) J Polym Sci A Polym Chem 31:505-514
23. Ropson N, Dubois P, Jerome R, Teyssie P (1995) Macromolecules 28:7589-7598
24. Spassky N, Simic V, Montaudo MS, Hubert-Pfalzgraf LG (2000) Macromol Chem Phys 201:2432-2440
25. Coudane J, Ustariz-Peyret C, Schwach G, Vert M (1997) J Polym Sci A Polym Chem 35:1651-1658
26. Brochu S, Prudhomme RE, Barakat I, Jerome R (1995) Macromolecules 28:5230-5239
27. Stevels WM, Ankoné MJK, Dijkstra PJ, Feijen J (1996) Macromolecules 29:6132-6138
28. McClain SJF, Ford TM, Drysdale NE (1992) Polym Prep: 463-464
29. Stevels WM, Ankoné MJK, Dijkstra PJ, Feijen J (1996) Macromolecules 29:3332-3333
30. Ovitt TM, Coates GW (1999) J Am Chem Soc 121:4072-4073
31. Ma H, Spaniol TP, Okuda J (2006) Angew Chem Int Ed 45:7818-7821
32. Ma H, Spaniol TP, Okuda J (2003) Dalton Trans: 4770-4780
33. Grunova E, Kirillov E, Roisnel T, Carpentier J-Fo (2008) Organometallics 27:5691-5698
34. Ajellal N, Lyubov DM, SinenkovMA, Fukin GK, Cherkasov AV, Thomas CM, Carpentier J-F, Trifonov AA (2008) Chem Eur J 14:5440-5448
35. Aubrecht KB, Chang K, Hillmyer MA, Tolman WB (2001) J Polym Sci A Polym Chem 39:284-293
36. Hodgson LM, Platel RH, White AJP, Williams CK (2008) Macromolecules 41:8603-8607
37. Alaaeddine A, Amgoune A, Thomas CM, Dagorne S, Bellemin-Laponnaz S, Carpentier J-F (2006) Eur J Inorg Chem: 3652-3658
38. Amgoune A, Thomas CM, Roisnel T, Carpentier J-F (2006) Chem Eur J 12:169-179
39. Buffet J-C, Okuda J (2011) Dalton Trans 40:7748-7754
40. Ma H, Spaniol TP, Okuda J (2008) Inorg Chem 47:3328-3339
41. Chmura AJ, Davidson MG, Frankis CJ, Jones MD, Lunn MD (2008) Chem Commun: 1293-1295
42. Mahrova TV, Fukin GK, Cherkasov AV, Trifonov AA, Ajellal N, J-Fo C (2009) Inorg Chem 48:4258-4266
43. Bouyahyi M, Ajellal N, Kirillov E, Thomas CM, Carpentier J-F (2011) Chem Eur J 17: 1872-1883
44. Blake MP, Schwarz AD, Mountford P (2011) Organometallics 30:1202-1214
45. Clark L, Cushion MG, Dyer HE, Schwarz AD, Duchateau R, Mountford P (2010) Chem Commun 46:273-275
46. Dyer HE, Huijser S, Susperregui N, Bonnet F, Schwarz AD, Duchateau R, Maron L, Mountford P (2010) Organometallics 29:3602-3621
47. Bonnet F, Cowley AR, Mountford P (2005) Inorg Chem 44:9046-9055
48. Dyer HE, Huijser S, Schwarz AD, Wang C, Duchateau R, Mountford P (2008) Dalton Trans: 32-35
49. Arnold PL, Buffet JC, Blaudeck R, Sujecki S, Wilson C (2009) Chem Eur J 15:8241-8250
50. Arnold PL, Buffet JC, Blaudeck RP, Sujecki S, Blake AJ, Wilson C (2008) Angew Chem Int Ed 47:6033-6036
51. Gregson CKA, Gibson VC, Long NJ, Marshall EL, Oxford PJ, White AJP (2006) J Am Chem Soc 128:7410-7411
52. Broderick EM, Diaconescu PL (2009) Inorg Chem 48:4701-4706
53. Broderick EM, Thuy-Boun PS, Guo N, Vogel CS, Sutter Jr, Miller JT, Meyer K, Diaconescu PL (2011) Inorg Chem 50:2870-2877
54. Platel RH, White AJP, Williams CK (2009) Chem Commun: 4115-4117
55. Platel RH, Hodgson LM, White AJP, Williams CK (2007) Organometallics 26:4955-4963
56. Platel RH, White AJP, Williams CK (2008) Inorg Chem 47:6840-6849
57. Kricheldorf HR, Berl M, Scharnagl N (1988) Macromolecules 21:286-293
58. Kowalski A, Duda A, Penczek S (1998) Macromolecules 31:2114-2122
59. Spassky N, Wisniewski M, Pluta C, Le Borgne A (1996) Macromol Chem Phys 197:2627-2637
60. Chisholm MH, Patmore NJ, Zhou Z (2005) Chem Commun: 127-129
61. Darensbourg DJ, Karroonnirun O, Wilson SJ (2011) Inorg Chem 50:6775-6787
62. Dijkstra PJ, Du H, Feijen J (2011) Polym Chem 2:520-527
63. Darensbourg DJ, Karroonnirun O (2010) Organometallics 29:5627-5634
64. Bouyahyi M, Grunova E, Marquet N, Kirillov E, Thomas CM, Roisnel T, Carpentier J-F (2008) Organometallics 27:5815-5825
65. Peckermann I, Kapelski A, Spaniol TP, Okuda J (2009) Inorg Chem 48:5526-5534
66. Loh T-P, Chua G-L (2006) Chem Commun: 2739-2749
67. Shen Z-L, Ji S-J, Loh T-P (2008) Tetrahedron 64:8159-8163
68. Douglas AF, Patrick BO, Mehrkhodavandi P (2008) Angewandte Chemie 120:2322-2325
69. Pietrangelo A, Knight SC, Gupta AK, Yao LJ, Hillmyer MA, Tolman WB (2010) J Am Chem Soc 132:11649-11657
70. Pietrangelo A, Hillmyer MA, Tolman WB (2009) Chem Commun: 2736-2737
71. Buffet J-C, Okuda J, Arnold PL (2010) Inorg Chem 49:419-426
72. Horeglad P, Kruk P, Pécaut J (2010) Organometallics 29:3729-3734
73. Williams CK, Breyfogle LE, Choi SK, Nam W, Young VG, Hillmyer MA, Tolman WB (2003) J Am Chem Soc 125:11350-11359
74. Lian B, Ma H, Spaniol TP, Okuda J (2009) Dalton Trans: 9033-9042
75. Clark L, Cushion MG, Dyer HE, Schwarz AD, Duchateau R, Mountford P (2010) Chem Commun (Camb) 46:273-275
76. Chisholm MH, Navarro-Llobet D, Gallucci J (2001) Inorg Chem 40:6506-6508
77. Aresta M (2010) Carbon Dioxide as Chemical Feedstock. Wiley-VCH, Weinheim
78. Mikkelsen M, Jorgensen M, Krebs FC (2010) Energ Environ Sci 3:43-81
79. MacDowell N, Florin N, Buchard A, Hallett J, Galindo A, Jackson G, Adjiman CS, Williams CK, Shah N, Fennell P (2010) Energ Environ Sci 3:1645-1669
80. Zhang Y, Chan JYG (2010) Energ Environ Sci 3:408-417
81. Riduan SN, Zhang Y (2010) Dalton Trans 39:3347-3357
82. Sakakura T, Choi J-C, Yasuda H (2007) Chem Rev 107:2365-2387
83. Aresta M, Dibenedetto A (2007) Dalton Trans: 2975-2992
84. Arakawa H, Aresta M, Armor JN, Barteau MA, Beckman EJ, Bell AT, Bercaw JE, Creutz C, Dinjus E, Dixon DA, Domen K, DuBois DL, Eckert J, Fujita E, Gibson DH, Goddard WA, Goodman DW, Keller J, Kubas GJ, Kung HH, Lyons JE, Manzer LE, Marks TJ, Morokuma K, Nicholas KM, Periana R, Que L, Rostrup-Nielson J, Sachtler WMH, Schmidt LD, Sen A, Somorjai GA, Stair PC, Stults BR, Tumas W (2001) Chem Rev 101:953-996
85. Sakakura T, Kohno K (2009) Chem Commun: 1312-1330
86. Soga K, Chiang W-Y, Ikeda S (1974) J Polymer Sci Polymer Chem Ed 12:121-131
87. Kuran W (1998) Prog Polym Sci 23:919-992
88. Ihata O, Kayaki Y, Ikariya T (2005) Macromolecules 38:6429-6434
89. Kember MR, Buchard A, Williams CK (2011) Chem Commun 47:141-163
90. Darensbourg DJ (2010) Inorg Chem 49:10765-10780
91. Darensbourg DJ (2007) Chem Rev 107:2388-2410
92. Sugimoto H, Inoue S (2004) J Polym Sci A Polym Chem 42:5561-5573
93. Nozaki K (2004) Pure Appl Chem 76:541-546
94. Darensbourg DJ, Mackiewicz RM, Phelps AL, Billodeaux DR (2004) Acc Chem Res 37:836-844
95. Coates GW, Moore DR (2004) Angew Chem Int Ed 43:6618-6639
96. Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155-174
97. Luinstra GA (2008) Polym Rev 48:192-219
98. Klaus S, Lehenmeier MW, Anderson CE, Rieger B (2011) Coord Chem Rev 255:1460-1479
99. Staples CA, Dome PB, Klecka GM, Oblock ST, Harris LR (1998) Chemosphere 36:2149-2173
100. Hengstler JG, Foth H, Gebel T, Kramer PJ, Lilienblum W, Schweinfurth H, Vãlkel W, Wollin KM, Gundert-Remy U (2011) Crit Rev Toxicol 41: 263-291
101. www.novomer.com and www.empowermaterials.com Accessed 21 Jul 2011.
102. Moore DR, Cheng M, Lobkovsky EB, Coates GW (2003) J Am Chem Soc 125:11911-11924
103. Luinstra GA, Haas GR, Molnar F, Bernhart V, Eberhardt R, Rieger B (2005) Chem Eur J 11:6298-6314
104. Sugimoto H, Ohtsuka H, Inoue S (2005) J Polym Sci A Polym Chem 43:4172-4186
105. Chatterjee C, Chisholm MH (2011) Inorg Chem 50:4481-4492
106. Inoue S (2000) J Polym Sci A Polym Chem 38:2861-2871
107. Kim JG, Cowman CD, LaPointe AM, Wiesner U, Coates GW (2011) Macromolecules 44:1110-1113
108. Yoo J, Na SJ, Park HC, Cyriac A, Lee BY (2010) Dalton Trans 39:2622-2630
109. Aida T, Inoue S (1982) Macromolecules 15:682-684
110. Takeda N, Inoue S (1978) Makromol Chem Macromol Chem Phys 179:1377-1381
111. Darensbourg DJ, Holtcamp MW (1995) Macromolecules 28:7577-7579
112. Darensbourg DJ, Holtcamp MW, Struck GE, Zimmer MS, Niezgoda SA, Rainey P, Robertson JB, Draper JD, Reibenspies JH (1998) J Am Chem Soc 121:107-116
113. Darensbourg DJ, Wildeson JR, Yarbrough JC, Reibenspies JH (2000) J Am Chem Soc 122:12487-12496
114. Kuran W (1991) Appl Organomet Chem 5:191-194
115. Kuran W, Listos T (1992) Macromol Chem Phys 193:945-956
116. Kuran W, Listos T (1994) Macromol Chem Phys 195:1011-1015
117. Cheng M, Lobkovsky EB, Coates GW (1998) J Am Chem Soc 120:11018-11019
118. Cheng M, Darling NA, Lobkovsky EB, Coates GW (2000) Chem Commun: 2007-2008
119. Cheng M, Moore DR, Reczek JJ, Chamberlain BM, Lobkovsky EB, Coates GW (2001) J Am Chem Soc 123:8738-8749
120. Moore DR, Cheng M, Lobkovsky EB, Coates GW (2002) Angew Chem Int Ed 41:2599-2602
121. Allen SD, Moore DR, Lobkovsky EB, Coates GW (2002) J Am Chem Soc 124:14284-14285
122. Jacobsen EN, Tokunaga M, Larrow JF (2000) PCT Int Appl WO 2000009463
123. Darensbourg DJ, Yarbrough JC (2002) J Am Chem Soc 124:6335-6342
124. Darensbourg DJ, Mackiewicz RM (2005) J Am Chem Soc 127:14026-14038
125. Darensbourg DJ, Mackiewicz RM, Billodeaux DR (2005) Organometallics 24:144-148
126. Darensbourg DJ, Mackiewicz RM, Phelps AL, Billodeaux DR (2004) Accounts Chem Res 37:836-844
127. Darensbourg DJ, Mackiewicz RM, Rodgers JL, Fang CC, Billodeaux DR, Reibenspies JH (2004) Inorg Chem 43:6024-6034
128. Darensbourg DJ, Mackiewicz RM, Rodgers JL, Phelps AL (2004) Inorg Chem 43:1831-1833
129. Darensbourg DJ, Rodgers JL, Mackiewicz RM, Phelps AL (2004) Catal Today 98:485-492
130. Darensbourg DJ, Bottarelli P, Andreatta JR (2007) Macromolecules 40:7727-7729
131. Darensbourg DJ, Moncada AI, Choi W, Reibenspies JH (2008) J Am Chem Soc 130:6523-6533
132. Eberhardt R, Allmendinger M, Rieger B (2003) Macromol Rapid Commun 24:194-196
133. Darensbourg DJ, Phelps AL (2005) Inorg Chem 44:4622-4629
134. Nakano K, Nakamura M, Nozaki K (2009) Macromolecules 42:6972-6980
135. Rao D-Y, Li B, Zhang R, Wang H, Lu X-B (2009) Inorg Chem 48:2830-2836
136. Qin Z, Thomas CM, Lee S, Coates GW (2003) Angew Chem Int Ed 42:5484-5487
137. Darensbourg DJ, Billodeaux DR (2005) Inorg Chem 44:1433-1442
138. Nozaki K, Nakano K, Hiyama T (1999) J Am Chem Soc 121:11008-11009
139. Pilz MF, Limberg C, Lazarov BB, Hultzsch KC, Ziemer B (2007) Organometallics 26:3668-3676
140. Piesik DFJ, Range S, Harder S (2008) Organometallics 27:6178-6187
141. Xiao YL, Wang Z, Ding KL (2005) Chem Eur J 11:3668-3678
142. Bok T, Yun H, Lee BY (2006) Inorg Chem 45:4228-4237
143. Cui D, Nishiura M, Hou Z (2005) Macromolecules 38:4089-4095
144. Cui D, Nishiura M, Tardif O, Hou Z (2008) Organometallics 27:2428-2435
145. Kember MR, Knight PD, Reung PTR, Williams CK (2009) Angew Chem Int Ed 48: 931-933
146. Kember MR, White AJP, Williams CK (2010) Macromolecules 43:2291-2298
147. Buchard A, Kember MR, Sandeman KG, Williams CK (2011) Chem Commun 47: 212-214
148. Nakano K, Hiyama T, Nozaki K (2005) Chem Commun: 1871-1873
149. Allen SD, Moore DR, Lobkovsky EB, Coates GW (2003) J Organomet Chem 683:137-148
150. Xiao YL, Wang Z, Ding KL (2006) Macromolecules 39:128-137
151. Chen X, Shen Z, Zhang Y (1991) Macromolecules 24:5305-5308
152. Kember MR, White AJP, Williams CK (2009) Inorg Chem 48:9535-9542
153. Nikitinskii AV, Bochkarev LN, Khorshev SY, Bochkarev MN (2004) Russ J Gen Chem 74:1197-1200
154. Dengler JE, Lehenmeier MW, Klaus S, Anderson CE, Herdtweck E, Rieger B (2011) Eur J Inorg Chem 2011:336-343
155. Cohen CT, Chu T, Coates GW (2005) J Am Chem Soc 127:10869-10878
156. Nakano K, Kamada T, Nozaki K (2006) Angew Chem Int Ed 45:7274-7277
157. Noh EK, Na SJ, Sujith S, Kim SW, Lee BY (2007) J Am Chem Soc 129:8082-8083
158. Sujith S, Min JK, Seong JE, Na SJ, Lee BY (2008) Angew Chem Int Ed 47:7306-7309
159. Ren W-M, Liu Z-W, Wen Y-Q, Zhang R, Lu X-B (2009) J Am Chem Soc 131:11509-11518
160. Nakano K, Hashimoto S, Nozaki K (2010) Chem Sci: 369-373
161. Lu X-B, Wang Y (2004) Angew Chem Int Ed 43:3574-3577
162. Lu XB, Shi L, Wang YM, Zhang R, Zhang YJ, Peng XJ, Zhang ZC, Li B (2006) J Am Chem Soc 128:1664-1674
163. Darensbourg DJ, Yarbrough JC, Ortiz C, Fang CC (2003) J Am Chem Soc 125:7586-7591
164. Jacobsen EN (2000) Acc Chem Res 33:421-431
165. Nielsen LPC, Stevenson CP, Blackmond DG, Jacobsen EN (2004) J Am Chem Soc 126:1360-1362
166. Na SJ, Sujith S, Cyriac A, Kim BE, Yoo J, Kang YK, Han SJ, Lee C, Lee BY (2009) Inorg Chem 48:10455-10465
167. Li B, Zhang R, Lu X-B (2007) Macromolecules 40:2303-2307
168. Wu G-P, Wei S-H, Lu X-B, Ren W-M, Darensbourg DJ (2010) Macromolecules 43:9202-9204
169. Ren W-M, Zhang X, Liu Y, Li J-F, Wang H, Lu X-B (2010) Macromolecules 43:1396-1402
170. Konsler RG, Karl Jr, Jacobsen EN (1998) J Am Chem Soc 120:10780-10781
171. Cohen CT, Coates GW (2006) J Polym Sci A Polym Chem 44:5182-5191
172. Vagin SI, Reichardt R, Klaus S, Rieger B (2010) J Am Chem Soc 132:14367-14369