Abstract
The development of sustainable routes to fine chemicals, liquid fuels, and polymeric materials from natural resources has attracted significant attention from academia, industry, the general public, and governments owing to dwindling fossil resources, surging energy demand, global warming concerns, and other environmental problems. Cellulosic material, such as grasses, trees, corn stover, or wheat straw, is the most abundant nonfood renewable biomass resources on earth. Such annually renewable material can potentially meet our future needs with a low carbon footprint if it can be efficiently converted into fuels, value added chemicals, or polymeric materials. This chapter focuses on various renewable monomers derived directly from cellulose or cellulose platforms and corresponding sustainable polymers or copolymers produced therefrom. Recent advances related to the polymerization processes and the properties of novel biomass-derived polymers are also reviewed and discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- β MMBL:
-
β-Methyl-α-methylene-γ-butyrolactone
- γ MMBL:
-
γ-Methyl-α-methylene-γ-butyrolactone
- ATRP:
-
Atom transfer radical polymerization
- nBA:
-
n-Butyl acrylate
- BM:
-
Bismaleimide
- CGC:
-
Me2Si(η 5-(Me4C5)(tBuN)
- CL:
-
Caprolactone
- CLP:
-
Classical Lewis pair
- Cp:
-
η 5-Cyclopentadienyl
- DA:
-
Diels–Alder
- DIOP:
-
Diisooctyl phthalate
- DMAP:
-
4-Dimethylaminopyridine
- DMF:
-
N,N-Dimethylformamide
- DOE:
-
Department of energy
- EBDMI:
-
C2H4(η 5-4,7-dimethylindenyl)2
- EBI:
-
C2H4(η 5-indenyl)2
- FLP:
-
Frustrated Lewis pair
- Flu:
-
η 5- or η 3-Fluorenyl
- FA:
-
Furfuryl alcohol
- FMA:
-
Furfuryl methacrylate
- GHG:
-
Greenhouse gas
- GPC:
-
Gel permeation chromatography
- GTP:
-
Group transfer polymerization
- HMF:
-
5-Hydroxymethylfurfural
- ItBu:
-
1,3-Di-tert-butylimidazol-2-ylidene
- ICD:
-
β-Isocupreidine
- ICD:
-
β-Isocupreidine
- IMes:
-
1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene
- it:
-
Isotactic (mm)
- LA:
-
Lactic acid or lactide
- LPP:
-
Lewis pair polymerization
- MBL:
-
α-Methylene-γ-butyrolactone
- MEP:
-
1,8-Bis(maleimido)-1-ethylpropane
- MIMA:
-
Maleimide methacrylate
- MMA:
-
Methyl methacrylate
- M n (M w):
-
Number (weight) average molecular weight
- MW:
-
Molecular weight
- MWD:
-
Molecular weight distribution
- NHC:
-
N-Heterocyclic carbene
- OSA:
-
Oligo(isosorbide adipate)
- OSS:
-
Oligo(isosorbide suberate)
- PASA:
-
Poly(aspartic acid)
- PDI:
-
Polydispersity index
- PET:
-
Poly(ethylene terephthalate)
- PFS:
-
Poly(2,5-furandimethylene succinate)
- PGA:
-
Poly(glutamic acid)
- PHBHV:
-
Bis-hydroxylated poly(3-hydroxybutyrate-co-3-hydroxyvalerate) oligomers
- PHUs:
-
Polyhydroxyurethanes
- PLA:
-
Polylactide
- PMMA:
-
Poly(methyl methacrylate)
- PP:
-
Polypropylene
- REM:
-
Rare earth metal
- ROP:
-
Ring-opening polymerization
- RSKA:
-
Trialkylsilyl methyl dimethylketene acetal
- RT:
-
Room temperature
- st:
-
Syndiotactic (rr)
- SA:
-
Succinic acid
- SDH:
-
Isosorbide dihexanoate
- SEM:
-
Scanning electron microscopy
- T g :
-
Glass transition temperature
- THF:
-
Tetrahydrofuran
- TOF:
-
Turnover frequency
- TPT:
-
1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene
References
IEA (2007) World energy outlook world energy outlook. International Energy Agency, Paris
Rass-Hansen J, Falsig H, Jorgensen B, Christensen CH (2007) J Chem Technol Biotechnol 82:329–333
Olah GA, Goeppert A, Prakash GKS (2006) Beyond oil and gas: the methanol economy. Wiley-VCH, Weinheim. ISBN 3-527-31275-7
Weisz PB (2004) Phys Today 57:47–52
IPCC (2007) Climate change 2007: the physical science basis. In: Solomon S, Qin D, Manning M, Chen Z, Marquis M, Averyt KB et al (eds) Contribution of working group 1 to the fourth assessment report of the intergovernmental panel on climate change. Cambridge University Press, Cambridge/New York
Morschbacker A (2009) Polym Rev 49:79–84
Dusselier M, Van Wouwe P, Dewaele A, Makshina E, Sels BF (2013) Energy Environ Sci 6:1415–1442
Jin F, Enomoto H (2011) Energy Environ Sci 4:382–397
Corma A, Iborra S, Velty A (2007) Chem Rev 107:2411–2502
Drumright RE, Gruber PR, Henton DE (2000) Adv Mater 12:1841–1846
Vink ETH, Rábago KR, Glassner DA, Gruber PR (2003) Polym Degrad Stab 80:403–419
Datta R, Henry M (2006) J Chem Technol Biotechnol 81:1119–1129
Fan Y, Zhou C, Zhu X (2009) Catal Rev Sci Eng 51:293–324
Bozell JJ, Petersen GR (2010) Green Chem 12:539–554
MäKi-Arvela P, Simakova IL, Salmi T, Murzin DY (2014) Chem Rev 114(3):1909–1971
Auras R, Lim LT, Selke SEM, Tsuji H (2010) Poly(lactic acid) – synthesis structures, properties, processing, and applications. Wiley, Hoboken
Inkinen S, Hakkarainen M, Albertsson AC, Södergard A (2011) Biomacromolecules 12:523–532
Takasu A, Narukawa Y, Hirabayashi T (2006) J Polym Sci Pol Chem 44:5247–5253
Kim KW, Woo SI (2002) Macromol Chem Phys 203:2245–2250
Kamber NE, Jeong W, Waymouth RM, Pratt RC, Lohmeijer BGG, Hedrick JL (2007) Chem Rev 107:5813–5840
Hayashi Y, Sasaki Y (2005) Chem Commun 2716–2718
Janssen KPF, Paul JS, Sels BF, Jacobs PA (2007) Stud Surf Sci Catal 170B:1222–1227
Roman-Leshkov Y, Moliner M, Labinger JA, Davis ME (2010) Angew Chem Int Ed 49:8954–8957
Pescarmona P, Janssen KPF, Delaet C, Stroobants C, Houthoofd K, Philippaerts A, Jonghe CD, Paul JS, Jacobsand PA, Sels BF (2010) Green Chem 12:1083–1089
Taarning E, Saravanamurugan S, Holm MS, Xiong JM, West RM, Christensen CH (2009) ChemSusChem 2:625–627
West RM, Holm MS, Saravanamurugan S, Xiong JM, Beversdorf Z, Taarning E, Christensen CH (2010) J Catal 269:122–130
Rasrendra CB, Fachri BA, Makertihartha GBN, Adisasmito S, Heeres HJ (2011) ChemSusChem 4:768–777
Wang J, Masui Y, Onaka M (2011) Appl Catal B 107:135–139
de Clippel F, Dusselier M, Rompaey RV, Vanelderen P, Dijkmans J, Makshina E, Giebeler L, Oswald S, Baron GV, Denayer JFM, Pescarmona PP, Jacobs PA, Sels BF (2012) J Am Chem Soc 134:10089–10101
Holm MS, Saravanamurugan S, Taarning E (2010) Science 328:602–605
Rasrendra CB, Makertihartha IGBN, Adisasmito S, Heeres HJ (2010) Top Catal 53:1241–1247
Onda A, Ochi T, Kajiyoshi K, Yanagisawa K (2008) Catal Commun 9:1050–1053
Onda A, Ochi T, Kajiyoshi K, Yanagisawa K (2008) Appl Catal A 343:49–54
Zeng W, Cheng DG, Chen F, Zhan X (2009) Catal Lett 133:221–226
Epane G, Laguerre JC, Wadouachi A, Marek D (2010) Green Chem 12:502–506
Holm MS, Pagan-Torres YJ, Saravanamurugan S, Riisager A, Dumesic JA, Taarning E (2012) Green Chem 14:702–706
Roman-Leshkov Y, Davis ME (2011) ACS Catal 1:1566–1580
Lobo RF (2010) ChemSusChem 3:1237–1240
Yan X, Jin F, Tohji K, Moriya T, Enomoto H (2007) J Mater Sci 42:9995–9999
Liu Z, Li W, Pan C, Chen P, Lou H, Zheng X (2011) Catal Commun 15:82–87
Yan XY, Jin FM, Tohji K, Kishita A, Enomoto H (2010) AIChE J 56:2727–2733
Barros dos Santors J, Lins da Silva F, Altino FMRS, Moneira da Silva T, Meneghetti MR, Meneghetti SMP (2013) Catal Sci Technol 3:673–678
Wang FW, Huo ZB, Wang YQ, Jin FM (2011) Res Chem Intermediat 37:487–492
Zhang S, Jin F, Hu J, Huo Z (2011) Bioresour Technol 102:1998–2003
Sanchez C, Eguees I, Garcia A, Llano-Ponte R, Labidi J (2012) Chem Eng J 181:655–660
Wang FF, Liu CL, Dong WS (2013) Green Chem 15:2091–2095
Stere C, Iovu M, Boborodea A, Vasilescu DS, Fazakas-Anca IS (1998) Polym Adv Technol 9:322–325
Bhaw-Luximon A, Jhurry D, Spassky N, Pensec S, Belleney J (2001) Polymer 42:9651–9656
McGuinness DS, Marshall EL, Gibson VC, Steed JW (2003) J Polym Sci Pol Chem 41:3798–3803
Csihony S, Beaudette TT, Sentman AC, Nyce GW, Waymouth RM, Hedrick JL (2004) Adv Synth Catal 346:1081–1086
Barskaya IG, Lyudvig YB, Shifrina RR, Izyumnikov AL (1983) Vysokomol Soedin Ser A 25:1283–1288
Emig N, Nguyen H, Krautscheid H, Reau R, Cazaux JB, Bertrand G (1998) Organometallics 17:3599–3608
Bourissou D, Martin-Vaca B, Dumitrescu A, Graullier M, Lacombe F (2005) Macromolecules 38:9993–9998
Basko M, Kubisa P (2006) J Polym Sci Pol Chem 44:7071–7081
Pratt RC, Lohmeijer BGG, Long DA, Waymouth RM, Hedrick JL (2006) J Am Chem Soc 128:4556–4557
Chuma A, Horn HW, Swope WC, Pratt RC, Zhang L, Lohmeijer BGG, Wade CG, Waymouth RM, Hedrick JL, Rice JE (2008) J Am Chem Soc 130:6749–6754
Becker JM, Tempelaar S, Stanford MJ, Pounder RJ, Covington JA, Dove AP (2010) Chem Eur J 16:6099–6105
Dechy-Cabaret O, Martin-Vaca B, Bourissou D (2004) Chem Rev 104:6147–6176
Platel RH, Hodgson LM, Williams CK (2008) Polym Rev 48:11–63
Wheaton CA, Hayes PG, Ireland BJ (2009) Dalton Trans 4832–4846
Wu J, Yu TL, Chen CT, Lin CC (2006) Coord Chem Rev 250:602–626
Mehta R, Kumar V, Bhunia H, Upadhyay SN (2005) J Macromol Sci C Polym Rev 45:325–349
Kricheldorf HR (2001) Chemosphere 43:49–54
Dijkstra PJ, Dum H, Feijen J (2011) Polym Chem 2:520–527
Stanford MJ, Dove AP (2010) Chem Soc Rev 39:486–494
Thomas CM (2010) Chem Soc Rev 39:165–173
Dove AP, Gibson VC, Marshall EL, Rzepa HS, White AJP, Williams DJ (2006) J Am Chem Soc 128:9834–9843
Williams CK, Breyfogle LE, Choi SK, Nam W, Young VG, Hillmyer MA, Tolman WB (2003) J Am Chem Soc 125:11350–11359
Chamberlain BM, Cheng M, Moore DR, Ovitt TM, Lobkovsky EB, Coates GW (2001) J Am Chem Soc 123:3229–3238
Ejfler J, Szafert S, Mierzwicki K, Jerzykiewicz LB, Sobota P (2008) Dalton Trans 6556–6562
Wu JC, Huang BH, Hsueh ML, Lai SL, Lin CC (2005) Polymer 46:9784–9792
Jones MD, Davidson MG, Keir CG, Hughes LM, Mahon MF, Apperley DC (2009) Eur J Inorg Chem 635–642
Zhong ZY, Dijkstra PJ, Feijen J (2002) Angew Chem Int Ed 41:4510–4513
Zhong ZY, Dijkstra PJ, Feijen J (2003) J Am Chem Soc 125:11291–11298
Ma H, Spaniol TP, Okuda J (2008) Inorg Chem 47:3328–3339
Ma H, Spaniol TP, Okuda J (2006) Angew Chem Int Ed 45:7818–7821
Peckermann I, Kapelski A, Spaniol TP, Okuda J (2009) Inorg Chem 48:5526–5534
Lian B, Ma H, Spaniol TP, Okuda J (2009) Dalton Trans 9033–9042
Amgoune A, Thomas CM, Ilinca S, Roisnel T, Carpentier JF (2006) Angew Chem Int Ed 45:2782–2784
Abdel-Fattah TM, Pinnavaia TJ (1996) Chem Commun 665–666
Tschan MJL, Brulé E, Haquette P, Thomas CM (2012) Polym Chem 3:836–851
Spassky N, Wisniewski M, Pluta C, LeBorgne A (1996) Macromol Chem Phys 197:2627–2637
Ovitt TM, Coates GW (2000) J Polym Sci Pol Chem 38:4686–4692
Ovitt TM, Coates GW (2002) J Am Chem Soc 124:1316–1326
Tang Z, Chen X, Pang X, Yang Y, Zhang X, Jing X (2004) Biomacromolecules 5:965–970
Tang Z, Chen X, Yang Y, Pang X, Sun J, Zhang X, Jing X (2004) J Polym Sci Pol Chem 42:5974–5982
Ishii R, Nomura N, Kondo T (2004) Polym J 36:261–264
Nomura N, Ishii R, Yamamoto Y, Kondo T (2007) Chem Eur J 13:4433–4451
Bakewell C, Cao T, Long N, Le Goff XF, Auffrant A, Wiliams CK (2012) J Am Chem Soc 134:20577–20580
Nederberg F, Connor EF, Moller M, Glauser T, Hedrick JL (2001) AIChE J 40:2712–2715
Zhang L, Nederberg F, Messman JM, Pratt RC, Hedrick JL, Wade CG (2007) J Am Chem Soc 129:12610–12611
Miyake GM, Chen EY-X (2011) Macromolecules 44:4116–4124
Ovitt TM, Coates GW (1999) J Am Chem Soc 121:4072–4073
Amgoune A, Thomas CM, Roisnel T, Carpentier JF (2006) Chem Eur J 12:169–179
Amgoune A, Thomas CM, Carpentier JF (2007) Macromol Rapid Commun 28:693–697
Hormnirun P, Marshall EL, Gibson VC, White AJP, Williams DJ (2004) J Am Chem Soc 126:2688–2689
Cai CX, Amgoune A, Lehmann CW, Carpentier JF (2004) Chem Commun 330–331
Liu X, Shang X, Tang T, Hu N, Pei F, Cui D, Chen X, Jing X (2007) Organometallics 26:2747–2757
Pietrangelo A, Hillmyer MA, Tolman WB (2009) Chem Commun 2736–2737
Dove AP, Li H, Pratt RC, Lohmeijer BGG, Culkin DA, Waymouth RM, Hedrich JL (2006) Chem Commun 2881–2883
Win DT (2005) Au J T 8:185–190
Thananatthanachon T, Rauchfuss TB (2010) ChemSusChem 3:1139–1141
Thananatthanachon T, Rauchfuss TB (2010) Angew Chem Int Ed 49:6616–6618
Werpy T, Petersen G (2004) In: U.S. Department of Energy (DOE) report: DOE/GO-102004-1992 (ed) Top value added chemicals from biomass, vol I
Jacoby M (2009) C&EN July 6:26–28
Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) Green Chem 13:754–793
Gandini A (2010) Polym Chem 1:245–251
Gandini A (1977) Adv Polym Sci 25:47–96
Gandini A (1990) ACS Sym Ser 433:195–208
Gandini A, Belgacem MN (1997) Prog Polym Sci 22:1203–1379
Moreau C, Belgacem MN, Gandini A (2004) Top Catal 27:11–30
Gandini A (2008) Macromolecules 41:9491–9504
Gandini A, Belgacem MN (2008) Furan derivatives and furan chemistry at the service of macromolecular materials. Elsevier, Amsterdam, pp 115–152
Kawashima D, Aihara T, Kobayashi Y, Kyotani T, Tomita A (2000) Chem Mater 12:3397–3401
Yao J, Wang H, Liu J, Chan KY, Zhang L, Xu N (2005) Carbon 43:1709–1715
Zarbin AJG, Bertholdo R, Oliveira MAFC (2002) Carbon 40:2413–2422
Wang H, Yao J (2006) Ind Eng Chem Res 45:6393–6404
Yi B, Rajagopalan R, Foley HC, Kim UJ, Liu X, Ecklund PC (2006) J Am Chem Soc 128:11307–11313
Hirasaki T, Meguro T, Wakihara T, Tatami J, Komeya K (2007) J Mater Sci 42:7604–7606
Cesano F, Scarano D, Bertarione S, Bonino F, Damin A, Bordiga S, Prestipino C, Lamberti C, Zecchina A (2008) J Photochem Photobiol A 196:143–153
Bertarione S, Bonino F, Cesano F, Jain S, Zanetti M, Scarano D, Zecchina A (2009) J Phys Chem B 113:10571–10574
Tondi G, Pizzi A, Pasch H, Celzard A, Rode K (2008) Eur Polym J 44:2938–2943
Tondi G, Pizzi A, Pasch H, Celzard A (2008) Polym Degrad Stab 93:968–975
Pizzi A, Tondi G, Pasch H, Celzard A (2008) J Appl Polym Sci 110:1451–1456
Yao J, Wang H (2007) Ind Eng Chem Res 46:6264–6268
Zhai Y, Tu B, Zhao D (2009) J Mater Chem 19:131–140
Grund S, Kempe P, Baumann G, Seifert A, Spange S (2007) Angew Chem Int Ed 46:628–632
Spange S, Grund S (2009) Adv Mater 21:2111–2116
Pranger L, Tannenbaum R (2008) Macromolecules 41:8682–8687
Tong X, Ma Y, Li Y (2010) Appl Catal Gen 385:1–13
Gallezot P (2012) Chem Soc Rev 41:1538–1558
Gandini A (2013) Prog Polym Sci 38:1–29
Liu Y, Chuo T (2013) Polym Chem 4:2194–2205
Syrett JA, Becer CR, Haddleton DM (2010) Polym Chem 1:978–987
Bergman SD, Wudl F (2008) J Mater Chem 18:41–62
Craven JM (1969) US Pat., 3,435,003
Stevens M, Jenkins A (1979) J Polym Sci 17:3675–3685
Kuster BFM (1990) Starch Stärke 42:314–321
Chujo Y, Sada K, Saegusa T (1990) Macromolecules 23:2636–2641
Imai Y, Itoh H, Naka K, Chujo Y (2000) Macromolecules 33:4343–4346
Canary SA, Stevens MP (1992) J Polym Sci Polym Chem 30:1755–1760
Laita H, Boufi S, Gandini A (1997) Eur Polym J 33:1203–1211
Gheneim R, Perez-Berumen C, Gandini A (2002) Macromolecules 35:7246–7253
Goiti E, Huglin MB, Rego JM (2001) Polymer 42:10187–10193
Goiti E, Huglin MB, Rego JM (2003) Macromol Rapid Commun 24:692–696
Goiti E, Huglin MB, Rego JM (2004) Eur Polym J 40:219–226
Goiti E, Huglin MB, Rego JM (2004) Eur Polym J 40:1451–1460
Tesoro GC, Sastri VR (1986) Ind Eng Chem Prod Res Dev 25:444–448
He X, Sastri VR, Tesoro GC (1989) Makromol Chem Rapid Commun 9:191–194
O’Dell R (1990). Ph.D. Thesis, Lancaster University, UK
Kuramoto N, Hayashi K, Nagai K (1994) J Polym Sci Polym Chem 30:2501–2504
Diakoumakos CD, Mikroyannidis JA (1992) J Polym Sci Polym Chem 30:2559–2563
Diakoumakos CD, Mikroyannidis JA (1994) Eur Polym J 30:465–472
Goussé C, Gandini A (1999) Polym Int 48:723–731
Gandini A, Coelho D, Silvestre AJ (2008) Eur Polym J 44:4029–4036
Chen X, Dam MA, Ono K, Mal A, Shen H, Nutt SR, Sheran K, Wudl F (2002) Science 295:1698–1702
Chen X, Wudl F, Mal AK, Shen H, Nutt SR (2003) Macromolecules 36:1802–1807
Kavitha AA, Singha NK (2007) J Polym Sci Pol Chem 45:4441–4449
Kavitha AA, Singha NK (2009) ACS Appl Mater Interfaces 1:1427–1436
He J, Zhang Y, Chen EYX (2013) J Polym Sci Pol Chem 51:2793–2803
Kötteritzsch J, Stumpf S, Hoeppener S, Vitz J, Hager MD, Schubert US (2013) Macromol Chem Phys 214:1636–1649
Zeng C, Seino H, Ren J, Hatanaka K, Yoshie N (2013) Macromolecules 46:1794–1802
Zeng C, Seino H, Ren J, Hatanaka K, Yoshie N (2013) Polymer 54:5351–5357
Franc G, Kakkar AK (2009) Chem Eur J 15:5630–5639
Bauer RE, Grimsdale AC, Müllen K (2005) Top Curr Chem 245:253–286
Bernhardt S, Baumgarten M, Müllen K (2006) Eur J Org Chem 11:2523–2529
Kim C, Kim H, Park K (2003) J Organomet Chem 667:96–102
Kim C, Kim H, Park K (2004) J Polym Sci Part A 42:2155–2161
Kim C, Lim KI, Song CG (2005) J Organomet Chem 690:3278–3285
McElhanon JR, Wheeler DR (2001) Org Lett 3:2681–2683
Szalai ML, McGrath DV, Wheeler DR, Zifer T, McElhanon JR (2007) Macromolecules 40:818–823
Sullivan PA, Olbricht BC, Akelaitis AJP, Mistry AA, Liao Y, Dalton LR (2007) J Mater Chem 17:2899–2903
Kose MM, Yesilbag G, Sanyal A (2008) Org Lett 10:2353–2356
Vieyres A, Lam T, Gillet R, Franc G, Castonguay A, Kakkar A (2010) Chem Commun 46:1875–1877
Costanzo PJ, Demaree JD, Beyer FL (2006) Langmuir 22:10251–10257
Costanzo PJ, Beyer FL (2007) Chem Mater 19:6168–6173
Aumsuzan N, Urban MW (2009) Polymer 50:33–36
Shi M, Wosnick JH, Ho K, Keating A, Shoihet MS (2007) Angew Chem Int Ed 46:6126–6131
Polaske NW, McGrath DV, McElhanon JR (2010) Macromolecules 43:1270–1276
Polaske NW, McGrath DV, McElhanon JR (2011) Macromolecules 44:3203–3210
Manzer LE (2006) Feedstocks for the future. ACS Sym Ser 921:40–51
Fitzpatrick SW (2006) Feedstocks for the future. ACS Sym Ser 921:271–287
Hayes DJ, Fitzpatick S, Hayes MHB, Ross JRH (2006) In: Kamm B, Gruber P, Kamm M (eds) Biorefineries-industrial processes and products. Wiley-VCH, Weinheim
Girisuta B, Janssen LPBM, Heeres HJ (2006) Chem Eng Res Des 84:339–349
Manzer LE (2004) Appl Catal A Gen 272:249–256
Sauer M, Porro D, Mattanovich D, Branduardi P (2008) Trends Biotechnol 26:100–108
Rossum MWPCV, Alberda M, Plas LHWVD (1998) Phytochemistry 49:723–729
Hoffman HMR, Rabe J (1985) Angew Chem Int Ed 24:94–110
Yokota K, Hirabayashi T (1992) (Iwata Kagaku Kogyo KK, Japan) J.P. Pat. 04049288 A
Pittman CU, Lee JH (2003) J Polym Sci Pol Chem 41:1759–1777
Hu Y, Wang X, Chen Y, Caporaso L, Cavallo L, Chen EYX (2013) Organometallics 32:1459–1465
Geilen FMA, Engendahl B, Harwardt A, Marquardt W, Klankermayer J, Leitner W (2010) Angew Chem Int Ed 49:5510–5514
Hu Y, Miyake GM, Wang B, Cui D, Chen EYX (2012) Chem Eur J 18:3345–3354
Agarwal S, Jin Q, Maji S (2012) ACS Sym Ser 1105:197–212
Mullin R (2004) Sustainable specialties. Chem Eng News 82(45):29–37
Akkapeddi MK (1979) Polymer 20:1215–1216
Stansbury JW, Antonucci JM (1992) Dent Mater 8:270–273
Akkapeddi MK (1979) Macromolecules 12:546–551
Kimura Y, Nakamura S (2009) JP,046,560 A
Pickett JE, Ye Q (2007) U.S. Patent 2007/0,122,625
Brandenburg CJ (2004) (to E. I. du Pont de Nemours and Company) WO 2004/069,926 A1
Miyake GM, Newton SE, Mariott WR, Chen EYX (2010) Dalton Trans 39:6710–6718
Chen X, Caporaso L, Cavallo L, Chen EYX (2012) J Am Chem Soc 134:7278–7281
Mosnáček J, Yoon JA, Juhari A, Koynov K, Matyjaszewski K (2009) Polymer 50:2087–2094
Mosnáček J, Matyjaszewski K (2008) Macromolecules 41:5509–5511
Ueda M, Takahashi M, Imai Y, Pittman CU Jr (1982) J Polym Sci Polym Chem Ed 20:2819–2828
Gridnev AA, Ittel SD (2000) (to E. I. du Pont de Nemours and Company) WO 00/35,960 A2
Sogah DY, Hertler WR, Webster OW, Cohen GM (1987) Macromolecules 20:1473–1488
Van den Brink M, Smulders W, van Herk AM, German AL (1999) J Polym Sci Pol Chem 37:3804–3816
Koinuma H, Sato K, Hirai H (1982) Makromol Chem Rapid Commun 3:311–315
Lee C, Hall HK Jr (1989) Macromolecules 22:21–25
Trumbo DL (1991) Polym Bull 26:271–275
Brandenburg CJ (2005) (to E. I. du Pont de Nemours and Company) U.S. Pat. 6,841,627 B2
Qi G, Nolan M, Schork FJ, Jones CW (2008) J Polym Sci Pol Chem 46:5929–5944
Suenaga J, Sutherlin DM, Stille JK (1984) Macromolecules 17:2913–2916
Cockburn RA, McKenna TFL, Hutchinson RA (2010) Macromol Chem Phys 211:501–509
Cockburn RA, Siegmann R, Payne KA, Beuermann S, McKenna TFL, Hutchinson RA (2011) Biomacromolecules 12:2319–2326
Hu Y, Xu X, Zhang Y, Chen Y, Chen EYX (2010) Macromolecules 43:9328–9336
Gowda RR, Chen EYX (2013) Dalton Trans 42:9263–9273
Miyake GM, Zhang Y, Chen EYX (2010) Macromolecules 43:4902–4908
Zhang Y, Gustafson LO, Chen EYX (2011) J Am Chem Soc 133:13674–13684
Hu Y, Gustafson LO, Zhu H, Chen EYX (2011) J Polym Sci Pol Chem 49:2008–2017
Zhang Y, Chen EYX (2012) Angew Chem Int Ed 51:2465–2469
Zhang Y, Schmitt M, Falivene L, Caporaso L, Cavallo LI, Chen EYX (2013) J Am Chem Soc 135:19725–19742
Zhang Y, Miyake GM, Chen EYX (2010) Angew Chem Int Ed 49:10158–10162
Zhang Y, Miyake GM, John MG, Falivene L, Caporaso L, Cavallo L, Chen EYX (2012) Dalton Trans 41:9119–9134
Brandenburg CJ (2003) (to E. I. du Pont de Nemours and Company) WO 03/048220 A2
Brandenburg CJ, Manzer LE, Subramanian P (2005) (to E. I. du Pont de Nemours and Company) WO 2005/028,529 A2
Ohrbom WH (2008) (to BASF Corporation) U.S. Pat. 2008/0,293,901 A1
Sakashita K (2007) (to Mitsubishi Rayon Co., Ltd) E.P. Pat. 1,834,968 A1
Chen EYX (2009) Chem Rev 109:5157–5214
Gowda RR, Chen EYX (2013) Encycl Polym Sci Technol, in press
Evans WJ, Grate JW, Choi HW, Bloom I, Hunter WE, Atwood JL (1985) J Am Chem Soc 107:941–946
Schuetz SA, Day VW, Sommer RD, Rheingold AL, Belot JA (2001) Inorg Chem 40:5292–5295
Xu X, Chen Y, Sun J (2009) Chem Eur J 15:846–850
Xu X, Chen Y, Feng J, Zou G, Sun J (2010) Organometallics 29:549–553
Wang B, Cui D, Lv K (2008) Macromolecules 41:1983–1988
Fedushikin IL, Dechert S, Schumann H (2001) Angew Chem Int Ed 40:561–563
Li Y, Ward EG, Reddy SS, Collins S (1997) Macromolecules 30:1875–1883
Ning Y, Zhu H, Chen EYX (2007) J Organomet Chem 692:4535–4544
Yang X, Stern CL, Marks TJ (1994) J Am Chem Soc 116:10015–10031
Rodriguez-Delgado A, Mariott WR, Chen EYX (2004) Macromolecules 37:3092–3100
Zhang Y, Ning Y, Caporaso L, Cavallo L, Chen EYX (2010) J Am Chem Soc 132:2695–2709
Rodriguez-Delgado A, Chen EYX (2005) Macromolecules 38:2587–2594
Bolig AD, Chen EYX (2004) J Am Chem Soc 126:4897–4906
Zhang Y, Chen EYX (2008) Macromolecules 41:36–42
Zhang Y, Chen EYX (2008) Macromolecules 41:6353–6360
Webster OW (2004) Adv Polym Sci 167:1–34
Webster OW, Hertler WR, Sogah DY, Farnham WB, RajanBabu TV (1983) J Am Chem Soc 105:5706–5708
Ryan SJ, Candish L, Lupton DW (2013) Chem Soc Rev 42:4906–4917
Grossmann A, Enders D (2012) Angew Chem Int Ed 51:314–325
Bugaut X, Glorius F (2012) Chem Soc Rev 41:3511–3522
Biju AT, Kuhl N, Glorius F (2011) Acc Chem Res 44:1182–1195
Dröge T, Glorius F (2010) Angew Chem Int Ed 50:6940–6952
Chiang PC, Bode JW (2010) In: RSC catalysis series. Royal Society of Chemistry, Cambridge, pp 399–435
Moore JL, Rovis T (2009) Top Curr Chem 291:77–144
Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122–3172
Nair V, Vellalath S, Babu BP (2008) Chem Soc Rev 37:2691–2698
Marion N, Díez-González S, Nolan SP (2007) Angew Chem Int Ed 46:2988–3000
Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606–5655
Bourissou D, Guerret O, Gabbaï FP, Bertrand G (2000) Chem Rev 100:39–91
Nyce GW, Glauser T, Connor EF, Möck A, Waymouth RM, Hedrick JL (2003) J Am Chem Soc 125:3046–3056
Connor EF, Nyce GW, Myers M, Möck A, Hedrick JL (2002) J Am Chem Soc 124:914–915
Nederberg F, Connor EF, Möller M, Glauser T, Hedrick JL (2001) Angew Chem Int Ed 40:2712–2715
Brown HA, Waymouth RM (2013) Acc Chem Res 46:2585–2596
Fèvre M, Pinaud J, Gnanou Y, Vignolle J, Taton D (2013) Chem Soc Rev 42:2142–2172
Kiesewetter MK, Shin EJ, Hedrick JL, Waymouth RM (2010) Macromolecules 43:2093–2107
Jeong W, Shin EJ, Culkin DA, Hedrick JL, Waymouth RM (2009) J Am Chem Soc 131:4884–4891
Culkin DA, Jeong W, Csihony S, Gomez ED, Balsara NP, Hedrick JL, Waymouth RM (2007) Angew Chem Int Ed 46:2627–2630
Dove AP, Li H, Pratt RC, Lohmeijer BGG, Culkin DA, Waymouth RM, Hedrick JL (2006) Chem Commun 2881–2883
Coulembier O, Dove AP, Pratt RC, Sentman AC, Culkin DA, Mespouille L, Dubois P, Waymouth RM, Hedrick JL (2005) Angew Chem Int Ed 44:4964–4968
Csihony S, Culkin DA, Sentman AC, Dove AP, Waymouth RM, Hedrick JL (2005) J Am Chem Soc 127:9079–9084
Shin EJ, Brown HA, Gonzalez S, Jeong W, Hedrick JL, Waymouth RM (2011) Angew Chem Int Ed 50:6388–6391
Sen TK, Sau SC, Mukherjee A, Modak A, Mandal SK, Koley D (2011) Chem Commun 47:11972–11974
Kamber NE, Jeong W, Gonzalez S, Hedrick JL, Waymouth RM (2009) Macromolecules 42:1634–1639
Jeong W, Hedrick JL, Waymouth RM (2007) J Am Chem Soc 129:8414–8415
Raynaud J, Absalon C, Gnanou Y, Taton D (2010) Macromolecules 43:2814–2823
Raynaud J, Ottou WN, Gnanou Y, Taton D (2010) Chem Commun 46:3203–3205
Raynaud J, Absalon C, Gnanou Y, Taton D (2009) J Am Chem Soc 131:3201–3209
Nederberg F, Lohmeijer BGG, Leibfarth F, Pratt RC, Choi J, Dove AP, Waymouth RM, Hedrick JL (2007) Biomacromolecules 8:153–160
Rodriguez M, Marrot S, Kato T, Stérin S, Fleury E, Baceiredo A (2007) J Organomet Chem 692:705–708
Lohmeijer BGG, Dubois G, Leibfarth F, Pratt RC, Nederberg F, Nelson A, Waymouth RM, Wade C, Hedrick JL (2006) Org Lett 8:4683–4686
Guo L, Lahasky SH, Ghale K, Zhang D (2012) J Am Chem Soc 134:9163–9171
Guo L, Zhang D (2009) J Am Chem Soc 131:18072–18074
Coutelier O, El Ezzi M, Destarac M, Bonnette F, Kato T, Baceiredo A, Sivasankarapillai G, Gnanou Y, Taton D (2012) Polym Chem 3:605–608
Pinaud J, Vijayakrishna K, Taton D, Gnanou Y (2009) Macromolecules 42:4932–4936
Nyce GW, Lamboy JA, Connor EF, Waymouth RM, Hedrick JL (2002) Org Lett 4:3587–3590
McCahill JSJ, Welch GC, Stephan DW (2007) Angew Chem Int Ed 46:4968–4971
Chase PA, Welch GC, Jurca T, Stephan DW (2007) Angew Chem Int Ed 46:8050–8053
Welch GC, Stephan DW (2007) J Am Chem Soc 129:1880–1881
Spies P, Erker G, Kehr G, Bergander K, Frohlich R, Grimme S, Stephan DW (2007) Chem Commun 5072–5074
Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Science 314:1124–1126
Erker G, Stephan DW (2013) Frustrated Lewis pairs I—uncovering and understanding. Topics in current chemistry 332
Erker G, Stephan DW (2013) Frustrated Lewis pairs II-expanding the scope. Top Curr Chem 334
Stephan DW, Erker G (2010) Angew Chem Int Ed 49:46–76
Chen EYX (2013) Top Curr Chem 334:239–260
Vogel R (2000) Ullmann’s encyclopedia of industrial chemistry. Wiley, on line
Hill K, Rhode O (1999) Fett/Lipid 101:25–33
Corma A, Hamid SBA, Iborra S, Velty A (2008) ChemSuSChem 1:85–90
Gallezot P, Cérino P, Blanc B, Flèche G, Fuertes P (1994) J Catal 146:93–102
van Gorpa K, Boermana E, Cavenaghib CV, Berben PH (1999) Catal Today 52:349–361
Gallezot P, Nicolaus N, Flèche G, Fuertes P, Perrard A (1998) J Catal 180:51–55
Van de Vyver S, Geboers J, Jacobs PA, Sels BF (2011) ChemCatChem 3:82–94
Fléche G, Huchette M (1986) Starch/Staerke 38:26–30
Kurszewska M, Skorupowa E, Madaj J, Konitz A, Wojnowski W, Wisniewski A (2002) Carbohydr Res 337:1261–1268
Xia J, Yu D, Hu Y, Zou B, Sun P, Li H, Huang H (2011) Catal Commun 12:544–547
Xi J, Zhang Y, Ding D, Xia Q, Wang J, Liu X, Lu G, Wang Y (2014) Appl Catal Gen 469:108–115
Fenouillot F, Rousseau A, Colomines G, Saint-Loup R, Pascault JP (2010) Prog Polym Sci 35:578–622
Yin B, Hakkarainen M (2011) J Appl Polym Sci 119:2400–2407
Rivera-Armenta JL, Heinze TH, Mendoza-Martínez AM (2004) Eur Polym J 40:2803–2812
Park HS, Gong MS, Knowles JC (2013) J Mater Sci Mater Med 24:281–294
Lorenzini C, Renard E, Bensemhoun J, Babinot J, Versace DL, Langlois V (2013) React Funct Polym 73:1656–1661
Karol MH, Kramarik JA (1996) Toxicol Lett 89:139–146
Besse V, Auvergne R, Carlotti S, Boutevin G, Otazaghine B, Caillol S, Pascault JP, Boutevin B (2013) React Funct Polym 73:588–594
Kricheldorf H, Weidner SM (2013) Eur Poly J 49:2293–2302
Kricheldorf H, Weidner SM (2013) Macromol Chem Phys 214:726–733
Williams CL, Chang CC, Do P, Nikbin N, Caratzoulas S, Vlachos DG, Lobo RF, Fan W, Dauenhauer PJ (2012) ACS Catal 2:935–939
Shiramizu M, Toste MFD (2012) Chem Eur J 17:12452–12457
Colonna M, Berti C, Fiorini M, Binassi F, Mazzacurati M, Vanini M, Kuranam S (2012) Presented at the ACS meeting “Polycondensation 2012”, San Francisco, September 2012
Werpy T, Petersen G (2004) Top value added chemicals from biomass, vol 1. U.S. Department of Energy, Oak Ridge
Fumagalli C (1997) Kirk–Othmer encyclopedia of chemical technology, vol 22, 4th edn. Wiley, New York, p 1074
Luo L, Voet EVD, Huppes G (2010) Bioresour Technol 101:5023–5032
Pipper G, Koch EM (1990) US Patent 5,030,709
Gaymans RJ, Venkatraman VS, Schuijer J (1984) J Polym Sci Polym Chem Ed 22:1373–1382
Carothers WH (1938). US Patent 2,130,948
Katsarava RD, Kharadze DP, Aualkhuili LM (1986) Makromol Chem 187:2053–2062
Bechthold I, Bretz K, Kabasci S, Kopitzky R, Springer A (2008) Chem Eng Technol 31:647–654
Coffman DD, Berchet GJ, Peterson WR, Spanagel EW (1947) J Polym Sci 2:306–313
Katsarava RD, Katsarava RD, Kharadze DP, Bendiashvili TM, Urman YG, Slonim IY, Alekseeva SG, Cefelin P, Janout V (1988) Acta Polym 39:523–533
Katsarava RD (2003) Macromol Sym 199:419–429
Wang Q, Shao Z, Yu T (1996) Polym Bull 36:659–665
Habeych DI, Eggink G, Boeriu CG (2011) Biocatal Biotransfor 29:299–310
Decker C, Moussa K, Bendaikha T (1991) J Polym Sci Pol Chem 29:739–747
Allen NS, Edge M, Mahammadian M, Jones K (1993) Polym Degrad Stab 41:191–196
Luda MP, Tauriello R, Camino G (2000) Eur Coat J 74:76–79
Hult A, Raanby B (1984) Polym Degrad Stab 8:75–87
Garaleh M, Yashiro T, Kricheldorf HR, Simon P, Chatti S (2010) Macromol Chem Phys 211:1206–1214
Chatti S, Weidner SM, Fildier A, Kricheldorf HR (2013) J Polym Sci Pol Chem 51:2464–2471
Shih IL, Van YT (2001) Bioresour Technol 79:207–225
Li C, Yu DF, Newman A, Cabra FL, Stephens C, Hunter NR, Milas L, Wallace S (1998) Cancer Res 58:2404–2409
Gross RA, Kalra B (2002) Science 297:803–807
Hasson D, Shemer H, Sher A (2011) Ind Eng Chem Res 50:7601–7607
Low KC, Wheeler AP, Koskan LP (1996) Adv Chem ACS 248:99–111
Zahuriaan-Mehr MJ, Pourjavadi A, Salimi H, Kurdtabar M (2009) Polym Adv Technol 20:655–671
Willke KD (2001) Appl Microbiol Biotechnol 56:289–295
Kiely DE, Chen L, Lin TH (1994) Polymers from agricultural coproducts. ACS Sym Ser 575:149–158
Kiely DE, Chen L, Lin TH (1994) J Am Chem Soc 116:571–578
Acknowledgments
This work was supported by the 1,000 Talents Young program and National Natural Science Foundation of China (NSFC) program (grant #21374040 to Y. Zhang) and by the US Department of Energy-Office of Basic Energy Sciences, grant DE-FG02-10ER16193 (to E. Y.-X. Chen).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Zhang, Y., Chen, E.YX. (2014). Polymerization of Nonfood Biomass-Derived Monomers to Sustainable Polymers. In: Nicholas, K. (eds) Selective Catalysis for Renewable Feedstocks and Chemicals. Topics in Current Chemistry, vol 353. Springer, Cham. https://doi.org/10.1007/128_2014_539
Download citation
DOI: https://doi.org/10.1007/128_2014_539
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-08653-8
Online ISBN: 978-3-319-08654-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)