End-of-Life Treatment of Poly(Vinyl Chloride) and Chlorinated Polyethylene by Dehydrochlorination in Ionic Liquids

There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination...

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Vydané v:	ChemSusChem Ročník 7; číslo 2; s. 610 - 617
Hlavní autori:	Glas, Daan, Hulsbosch, Joris, Dubois, Philippe, Binnemans, Koen, De Vos, Dirk E.
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	Weinheim WILEY-VCH Verlag 01.02.2014 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Predmet:	chlorine environmental chemistry Halogenation Imidazoles - chemistry ionic liquids Ionic Liquids - chemistry Kinetics Polyethylene - chemistry polymers Polyvinyl Chloride - chemistry waste prevention ionic liquids polymers waste prevention chlorine environmental chemistry
ISSN:	1864-5631, 1864-564X, 1864-564X
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Abstract	There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen‐bond‐accepting ability (β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P4444][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm3) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P4444][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by 13C cross‐polarization magic‐angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda–Grubbs second‐generation catalyst to yield α,ω‐dienes such as 1,5‐hexadiene and 1,6‐heptadiene. Easy as PVC: Thermally stable phosphonium ionic liquids (ILs) are the solvent and catalyst for the dehydrochlorination of polymers such as poly(vinyl chloride) (PVC). The true dissolution of PVC by ILs can facilitate the complete HCl elimination from the polymer chains. The dehydrochlorinated materials are characterized in detail and some of them are successfully depolymerized in a catalytic reverse acyclic diene metathesis (ADMET) process.
AbstractList	There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen‐bond‐accepting ability (β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P4444][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm3) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P4444][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by 13C cross‐polarization magic‐angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda–Grubbs second‐generation catalyst to yield α,ω‐dienes such as 1,5‐hexadiene and 1,6‐heptadiene. Easy as PVC: Thermally stable phosphonium ionic liquids (ILs) are the solvent and catalyst for the dehydrochlorination of polymers such as poly(vinyl chloride) (PVC). The true dissolution of PVC by ILs can facilitate the complete HCl elimination from the polymer chains. The dehydrochlorinated materials are characterized in detail and some of them are successfully depolymerized in a catalytic reverse acyclic diene metathesis (ADMET) process. There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen‐bond‐accepting ability ( β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P 4444 ][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm 3 ) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P 4444 ][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by 13 C cross‐polarization magic‐angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda–Grubbs second‐generation catalyst to yield α,ω‐dienes such as 1,5‐hexadiene and 1,6‐heptadiene. There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen-bond-accepting ability (β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P4444 ][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm(3) ) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P4444 ][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by (13) C cross-polarization magic-angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda-Grubbs second-generation catalyst to yield α,ω-dienes such as 1,5-hexadiene and 1,6-heptadiene.There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen-bond-accepting ability (β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P4444 ][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm(3) ) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P4444 ][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by (13) C cross-polarization magic-angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda-Grubbs second-generation catalyst to yield α,ω-dienes such as 1,5-hexadiene and 1,6-heptadiene. There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen-bond-accepting ability ([beta] value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80°C. PVC is dehydrochlorinated up to 98% after 60min in tetrabutylphosphonium chloride ([P4444][Cl]) at 180°C. PVC pieces stabilized by calcium stearate (4mm3) are dehydrochlorinated more slowly; conversions of 85 and 96% are reached after 1 and 8h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3g stabilized PVC in 0.5g IL, can be applied with only a minor loss of conversion. [P4444][Cl] proved to be stable during several consecutive reactions; after each run more than 99% of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by 13Ccross-polarization magic-angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda-Grubbs second-generation catalyst to yield [alpha],[omega]-dienes such as 1,5-hexadiene and 1,6-heptadiene. [PUBLICATION ABSTRACT] There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to dehydrochlorinate and/or dissolve the chlorinated polymers poly(vinyl chloride) (PVC) and chlorinated polyethylene (CPE). The dehydrochlorination activity of an IL depends mainly on its anion and is related to the high hydrogen-bond-accepting ability (β value) of the anion. Different phosphonium ILs successfully dissolve and dehydrochlorinate PVC and CPE at temperatures from 80 °C. PVC is dehydrochlorinated up to 98 % after 60 min in tetrabutylphosphonium chloride ([P4444 ][Cl]) at 180 °C. PVC pieces stabilized by calcium stearate (4 mm(3) ) are dehydrochlorinated more slowly; conversions of 85 and 96 % are reached after 1 and 8 h, respectively. Smaller pieces are dehydrochlorinated faster. High loadings, for example, 0.3 g stabilized PVC in 0.5 g IL, can be applied with only a minor loss of conversion. [P4444 ][Cl] proved to be stable during several consecutive reactions; after each run more than 99 % of the IL can be recovered. The structure of the dehydrochlorinated PVC was studied by (13) C cross-polarization magic-angle spinning NMR and FTIR spectroscopy; the removal of Cl and the formation of double bonds were confirmed. Carefully dehydrochlorinated CPE was processed further by acyclic diene metathesis depolymerization with ethylene and the Hoveyda-Grubbs second-generation catalyst to yield α,ω-dienes such as 1,5-hexadiene and 1,6-heptadiene.
Author	De Vos, Dirk E. Glas, Daan Dubois, Philippe Binnemans, Koen Hulsbosch, Joris
Author_xml	– sequence: 1 givenname: Daan surname: Glas fullname: Glas, Daan organization: Centre for Surface Chemistry and Catalysis, Department of Microbial and Molecular Systems, KU Leuven, Kasteelpark Arenberg 23, box 2461, 3001 Leuven (Belgium) – sequence: 2 givenname: Joris surname: Hulsbosch fullname: Hulsbosch, Joris organization: Centre for Surface Chemistry and Catalysis, Department of Microbial and Molecular Systems, KU Leuven, Kasteelpark Arenberg 23, box 2461, 3001 Leuven (Belgium) – sequence: 3 givenname: Philippe surname: Dubois fullname: Dubois, Philippe organization: Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers, University of Mons, Place du Parc 23, 7000 Mons (Belgium) – sequence: 4 givenname: Koen surname: Binnemans fullname: Binnemans, Koen organization: Division for Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, box 2404, 3001 Leuven (Belgium) – sequence: 5 givenname: Dirk E. surname: De Vos fullname: De Vos, Dirk E. email: dirk.devos@biw.kuleuven.be organization: Centre for Surface Chemistry and Catalysis, Department of Microbial and Molecular Systems, KU Leuven, Kasteelpark Arenberg 23, box 2461, 3001 Leuven (Belgium)
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Keywords	ionic liquids polymers waste prevention chlorine environmental chemistry
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References_xml	– reference: D. Braun, Prog. Polym. Sci. 2002, 27, 2171-2195. – reference: S. M. D. Prestes, S. D. Mancini, A. Rodolfo, R. C. Keiroglo, Waste Manage. Res. 2012, 30, 115-121. – reference: L. G. Parks, J. S. Ostby, C. R. Lambright, B. D. Abbott, G. R. Klinefelter, N. J. Barlow, L. E. Gray, Toxicol. Sci. 2000, 58, 339-349. – reference: P. van der Gryp, S. Marx, H. C. M. Vosloo, J. Mol. Catal. A 2012, 355, 85-95. – reference: C. J. Bradaric, A. Downard, C. Kennedy, A. J. Robertson, Y. H. Zhou, Green Chem. 2003, 5, 143-152. – reference: G. Grause, A. Buekens, Y. Sakata, A. Okuwaki, T. Yoshioka, J. Mater. Cycles Waste Manage. 2011, 13, 265-282. – reference: M. A. Tlenkopatchev, A. Barcenas, S. Fomine, Macromol. Theory Simul. 2001, 10, 729-735. – reference: J. P. Guthrie, Can. J. Chem. 1978, 56, 2342-2354. – reference: R. Miranda, J. Yang, C. Roy, C. Vasile, Polym. Degrad. Stab. 1999, 64, 127-144. – reference: D. Braun, J. Vinyl Addit. 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Snippet	There is an urgent need for green technologies to remove halogens from halogenated polymers at the end of their lifetime. Ionic liquids (ILs) were used to...
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SubjectTerms	chlorine environmental chemistry Halogenation Imidazoles - chemistry ionic liquids Ionic Liquids - chemistry Kinetics Polyethylene - chemistry polymers Polyvinyl Chloride - chemistry waste prevention
Title	End-of-Life Treatment of Poly(Vinyl Chloride) and Chlorinated Polyethylene by Dehydrochlorination in Ionic Liquids
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