a.Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
b.Jiangsu Key Laboratory for Micro and Nano Heat Fluid Flow Technology and Energy Application, School of Physical Science and Technology, Suzhou University of Science and Technology, Suzhou 215009, China
wangsheng@suda.edu.cn (S.W.)
tuyingfeng@suda.edu.cn (Y.F.T.)
Scan for full text
Chemical Recycling of Poly(ethylene furanoate) into Value-added Poly(ethylene-
Jing Li, Sheng Wang, Huan-Jun Lu, et al. Chemical Recycling of Poly(ethylene furanoate) into Value-added Poly(ethylene-
Chemical Recycling of Poly(ethylene furanoate) into Value-added Poly(ethylene-
Jing Li, Sheng Wang, Huan-Jun Lu, et al. Chemical Recycling of Poly(ethylene furanoate) into Value-added Poly(ethylene-
We provide here a novel value-added method for the chemical recycling of bio-based poly(ethylene furanoate) (PEF) to high-performance poly(ethylene-co-isosorbide furanoate) (PEIF) copolyesters by the combination of cyclodepolymerization method with cascade polycondensation-coupling ring-opening polymerization (PROP). The prepared sustainable PEIF fibers show excellent thermal and mechanical properties with bio-degradability.
We present here a novel strategy for the chemical recycling of bio-based poly(ethylene furanoate)s (PEF) to value-added high-performance bio-based poly(ethylene-,co,-isosorbide furanoate) (PEIF) copolyesters by the combination of cyclodepolymerization method with rapid cascade polycondensation-coupling ring-opening polymerization (PROP). The solution cyclodepolymerization of commercially available PEF affords cyclic oligo(ethylene 2,5-furandicarboxylate)s (COEFs), and the effects of reaction conditions on the yield of COEFs were studied. PEIF copolyesters with different isosorbide (IS) contents were synthesized ,via, the cascade PROP of COEFs with IS, which show significant enhanced glass transition temperature. By melt spinning, PEIF fibers with different orientation factors were prepared, with excellent thermal stability and mechanical performance. The obtained PEIF fibers can lift a weight ~25000 times higher than its weight. The PEIF fibers are stable under ambient conditions but are biodegradable following the “surface erosion” mechanism. These sustainable value-added biodegradable PEIF fibers offer a solution to the environmentally friendly fibers.
Bio-basedChemical recyclingFiberPROPSustainable
Rahimi,A.;García,J.M.Chemicalrecyclingofwasteplasticsfornewmaterialsproduction.Nat. Rev. Chem.2017,1,0046..
Getzler,Y.;Mathers,R.T.Sustainablepolymers:ourevolvingunderstanding.Acc. Chem. Res.2022,55,1869−1878..
Haque,F.M.;Ishibashi,J.S.A.;Lidston,C.A.L.;Shao,H.;Bates,F.S.;Chang,A.B.;Coates,G.W.;Cramer,C.J.;Dauenhauer,P.J.;Dichtel,W.R.;Ellison,C.J.;Gormong,E.A.;Hamachi,L.S.;Hoye,T.R.;Jin,M.;Kalow,J.A.;Kim,H.J.;Kumar,G.;LaSalle,C.J.;Liffland,S.;Lipinski,B.M.;Pang,Y.;Parveen,R.;Peng,X.;Popowski,Y.;Prebihalo,E.A.;Reddi,Y.;Reineke,T.M.;Sheppard,D.T.;Swartz,J.L.;Tolman,W.B.;Vlaisavljevich,B.;Wissinger,J.;Xu,S.;Hillmyer,M.A.Definingthemacromoleculesoftomorrowthroughsynergisticsustainablepolymerresearch.Chem. Rev.2022,122,6322−6373..
Tang,X.;Chen,E.Y.X.Towardinfinitelyrecyclableplasticsderivedfromrenewablecyclicesters.Chem2019,5,284−312..
Halonen,N.;Pálvölgyi,P.S.;Bassani,A.;Fiorentini,C.;Nair,R.;Spigno,G.;Kordas,K.Bio-basedsmartmaterialsforfoodpackagingandsensors—areview.Front. Mater.2020,7,82..
Cywar,R.M.;Rorrer,N.A.;Hoyt,C.B.;Beckham,G.T.;Chen,E.Y.X.Bio-basedpolymerswithperformance-advantagedproperties.Nat. Rev. Mater.2021,7,83−103..
Hong,K.;Sun,Q.;Zhang,X.;Fan,L.;Wu,T.;Du,J.;Zhu,Y.Fullybio-basedhigh-performancethermosetswithclosed-looprecyclability.ACS Sustainable Chem. Eng.2022,10,1036−1046..
Rosenboom,J.G.;Hohl,D.K.;Fleckenstein,P.;Storti,G.;Morbidelli,M.Bottle-gradepolyethylenefuranoatefromring-openingpolymerisationofcyclicoligomers.Nat. Commun.2018,9,2701..
Loos,K.;Zhang,R.;Pereira,I.;Agostinho,B.;Hu,H.;Maniar,D.;Sbirrazzuoli,N.;Silvestre,A.J.D.;Guigo,N.;Sousa,A.F.AperspectiveonPEFsynthesis,properties,andend-life.Front. Chem.2020,8,585..
Fei,X.;Wang,J.;Zhang,X.;Jia,Z.;Jiang,Y.;Liu,X.Recentprogressonbio-basedpolyestersderivedfrom2,5-furandicarbonxylicacid(FDCA).Polymers2022,14,625..
Burgess,S.K.;Kriegel,R.M.;Koros,W.J.Carbondioxidesorptionandtransportinamorphouspoly(ethylenefuranoate).Macromolecules2015,48,2184−2193..
Araujo,C.F.;Nolasco,M.M.;Ribeiro-Claro,P.J.A.;Rudić,S.;Silvestre,A.J.D.;Vaz,P.D.;Sousa,A.F.InsidePEF:chainconformationanddynamicsincrystallineandamorphousdomains.Macromolecules2018,51,3515−3526..
vanBerkel,J.G.;Guigo,N.;Visser,H.A.;Sbirrazzuoli,N.Chainstructureandmolecularweightdependentmechanicsofpoly(ethylene2,5-furandicarboxylate)comparedtopoly(ethyleneterephthalate).Macromolecules2018,51,8539−8549..
Takarada,W.;Sugimoto,K.;Nakajima,H.;Visser,H.A.;Gruter,G.M.;Kikutani,T.Melt-spunfibersfrombio-basedpolyester-fiberstructuredevelopmentinhigh-speedmeltspinningofpoly(ethylene2,5-furandicarboxylate)(PEF).Materials2021,14,1174..
Hohnemann,T.;Steinmann,M.;Schindler,S.;Hoss,M.;Konig,S.;Ota,A.;Dauner,M.;Buchmeiser,M.R.Poly(ethylenefuranoate)alongitslife-cyclefromapolycondensationapproachtohigh-performanceyarnanditsrecyclate.Materials2021,14,1044..
Hong,S.;Min,K.D.;Nam,B.U.;Park,O.O.Highmolecularweightbiofuran-basedco-polyestersforfoodpackagingapplications:synthesis,characterizationandsolid-statepolymerization.Green Chem.2016,18,5142−5150..
Saxon,D.J.;Nasiri,M.;Mandal,M.;Maduskar,S.;Dauenhauer,P.J.;Cramer,C.J.;LaPointe,A.M.;Reineke,T.M.Architecturalcontrolofisosorbide-basedpolyethersviaring-openingpolymerization.J. Am. Chem. Soc.2019,141,5107−5111..
Qian,W.;Liu,L.;Zhang,Z.;Su,Q.;Zhao,W.;Cheng,W.;Dong,L.;Yang,Z.;Bai,R.;Xu,F.;Zhang,Y.;Zhang,S.Synthesisofbioderivedpolycarbonateswithadjustablemolecularweightscatalyzedbyphenolic-derivedionicliquids.Green Chem.2020,22,2488−2497..
Weinland,D.H.;vanPutten,R.J.;Gruter,G.-J.M.Evaluatingthecommercialapplicationpotentialofpolyesterswith1,4:3,6-dianhydrohexitols(isosorbide,isomannideandisoidide)byreviewingthesyntheticchallengesinstepgrowthpolymerization.Eur. Polym. J.2022,164,110964..
Zhou,C.;Wei,Z.;Yu,Y.;Wang,Y.;Li,Y.Biobasedcopolyestersfromrenewableresources:synthesisandcrystallizationkineticsofpoly(propylenesebacate-co-isosorbidesebacate).RSC Adv.2015,5,68688−68699..
Nguyen,H.T.H.;Qi,P.;Rostagno,M.;Feteha,A.;Miller,S.A.Thequestforhighglasstransitiontemperaturebioplastics.J. Mater. Chem. A2018,6,9298−9331..
Ouyang,Q.;Liu,J.;Li,C.;Zheng,L.;Xiao,Y.;Wu,S.;Zhang,B.Afacilemethodtosynthesizebio-basedandbiodegradablecopolymersfromfurandicarboxylicacidandisosorbidewithhighmolecularweightsandexcellentthermalandmechanicalproperties.Polym. Chem.2019,10,5594−5601..
Chen,J.;Wu,J.;Qi,J.;Wang,H.Systematicstudyofthermaland(bio)degradablepropertiesofsemiaromaticcopolyestersbasedonnaturallyoccurringisosorbide.ACS Sustainable Chem. Eng.2018,7,1061−1071..
Weinland,D.H.;vanderMaas,K.;Wang,Y.;BottegaPergher,B.;vanPutten,R.J.;Wang,B.;Gruter,G.M.Overcomingthelowreactivityofbiobased,secondarydiolsinpolyestersynthesis.Nat. Commun.2022,13,7370..
Noordover,B.A.J.;Staalduinen,V.G.v.;Duchateau,R.;Koning,C.E.;Benthem,v.;Mak,M.;Heise,A.;Frissen,A.E.;Haveren,J.V.Co-andterpolyestersbasedonisosorbideandsuccinicacidforcoatingapplications: synthesisandcharacterization.Biomacromolecules2006,7,3406−3416..
Wu,J.;Thiyagarajan,S.;FonsecaGuerra,C.;Eduard,P.;Lutz,M.;Noordover,B.A.J.;Koning,C.E.;vanEs,D.S.Isohexidedinitriles:aversatilefamilyofrenewableplatformchemicals.ChemSusChem2017,10,3202−3211..
Xie,H.;Lu,H.;Zhang,Z.;Li,X.;Yang,X.;Tu,Y.Effectofblocknumberandweightfractiononthestructureandpropertiesofpoly(butyleneterephthalate)-block-poly(tetramethyleneoxide)multiblockcopolymers.Macromolecules2021,54,2703−2710..
Tu,Y.Cascadepolymerization.Acta Polymerica Sinica(inChinese)2019,50,1146−1155..
Huan,J.;Li,J.;Lan,Y.;Wang,S.;Li,X.;Yang,X.;Lu,H.;Tu,Y.Effectofoligo(ethyleneglycol)lengthonpropertiesofpoly(oligoethyleneglycolterephthalate)sandtheircyclicoligomers.Polymer2022,260,125369..
Li,H.;Yan,X.;Huan,J.;Wang,S.;Li,X.;Wang,Y.;Tu,Y.;Li,Z.Anefficientcyclo-depolymerizationrouteforthechemicalrecyclingofpoly(ethyleneadipate).Polym. Chem.2023,14,1019−1026..
Wang,W.;Wu,F.;Lu,H.;Li,X.;Yang,X.;Tu,Y.Acascadepolymerizationmethodforthepropertymodificationofpoly(butyleneterephthalate)bytheincorporationofisosorbide.ACS Appl. Polym. Mater.2019,1,2313−2321..
Li,J.;Wang,S.;Lu,H.;Tu,Y.;Wan,X.;Li,X.;Tu,Y.;Li,C.Y.Helicalcrystalsinaliphaticcopolyesters:Fromchiralamplificationtomechanicalpropertyenhancement.ACS Macro Lett.2023,12,369−375..
Xiao,Y.;He,C.;Yang,Z.F.;Chen,E.Q.;Lu,H.J.;Li,X.H.;Tu,Y.F.Theshacklingeffectincyclicazobenzeneliquidcrystal.Chinese J. Polym. Sci.2022,40,584−592..
Hubbard,P.;Brittain,W.J.;WilliamJ.Simonsick,J.;CharlesW.Ross,I.Synthesisandring-openingpolymerizationofpoly(alkylene2,6-naphthalenedicarboxylate)cyclicoligomers.Macromolecules1996,29,8304−8307..
Fukushima,K.;Coulembier,O.;Lecuyer,J.M.;Almegren,H.A.;Alabdulrahman,A.M.;Alsewailem,F.D.;McNeil,M.A.;Dubois,P.;Waymouth,R.M.;Horn,H.W.;Rice,J.E.;Hedrick,J.L.Organocatalyticdepolymerizationofpoly(ethyleneterephthalate).J. Polym. Sci. Part A: Polym. Chem.2011,49,1273−1281..
Hodge,P.Entropicallydrivenring-openingpolymerizationofstrainlessorganicmacrocycles.Chem. Rev.2014,114,2278−2312..
Tian,G.Q.;Yang,Z.H.;Zhang,W.;Chen,S.C.;Chen,L.;Wu,G.;Wang,Y.Z.Integrationofupcyclingandclosed-looprecyclingthroughalternativecyclization-depolymerization.Green Chem.2022,24,4490−4497..
Yang,R.;Xu,G.;Dong,B.;Hou,H.;Wang,Q.A“PolymertoPolymer”chemicalrecyclingofPLAplasticsbythe“DE-REPolymerization”strategy.Macromolecules2022,55,1726−1735..
Xu,G.;Wang,Q.Chemicallyrecyclablepolymermaterials:polymerizationanddepolymerizationcycles.Green Chem.2022,24,2321−2346..
Li,X.L.;Clarke,R.W.;Jiang,J.Y.;Xu,T.Q.;Chen,E.Y.Acircularpolyesterplatformbasedonsimplegem-disubstitutedvalerolactones.Nat. Chem.2023,15,278−285..
Brunelle,D.J.;Bradt,J.E.;Serth-Guzzo,J.;Takekoshi,T.;Evans,T.L.;Pearce,E.J.;Wilson,P.R.Semicrystallinepolymersviaring-openingpolymerization:Preparationandpolymerizationofalkylenephthalatecyclicoligomers.Macromolecules1998,31,4782−4790..
Pfister,D.;Storti,G.;Tancini,F.;Costa,L.I.;Morbidelli,M.Synthesisandring-openingpolymerizationofcyclicbutylene2,5-furandicarboxylate.Macromol. Chem. Phys.2015,216,2141−2146..
CarlosMorales-Huerta,J.;MartínezdeIlarduya,A.;Muñoz-Guerra,S.Poly(alkylene2,5-furandicarboxylate)s(PEFandPBF)byringopeningpolymerization.Polymer2016,87,148−158..
Papageorgiou,G.Z.;Papageorgiou,D.G.;Tsanaktsis,V.;Bikiaris,D.N.Synthesisofthebio-basedpolyesterpoly(propylene2,5-furandicarboxylate).Comparisonofthermalbehaviorandsolidstatestructurewithitsterephthalateandnaphthalatehomologues.Polymer2015,62,28−38..
Gan,Z.;Qu,S.;Li,S.;Tan,T.;Yang,J.FacilesynthesisofPET-basedpoly(etherester)swithstrikingphysicalandmechanicalproperties.React. Funct. Polym.2021,164,104936..
Zhu,J.;Cai,J.;Xie,W.;Chen,P.-H.;Gazzano,M.;Scandola,M.;Gross,R.A.Poly(butylene2,5-furandicarboxylate),abiobasedalternativetoPBT:synthesis,physicalproperties,andcrystalstructure.Macromolecules2013,46,796−804..
Knoop,R.J.I.;Vogelzang,W.;vanHaveren,J.;vanEs,D.S.Highmolecularweightpoly(ethylene-2,5-furanoate);criticalaspectsinsynthesisandmechanicalpropertydetermination.J. Polym. Sci., Part A: Polym. Chem.2013,51,4191−4199..
Burkersroda,F.v.;Schedl,L.;Gopferich,A.Whydegradablepolymersundergosurfaceerosionorbulkerosion.Biomaterials2002,23,4221−4231..
Herzog,K.;Müller,R.J.;Deckwer,W.D.Mechanismandkineticsoftheenzymatichydrolysisofpolyesternanoparticlesbylipases.Polym. Degrad. Stabil.2006,91,2486−2498..
0
浏览量
4
Downloads
0
CSCD
关联资源
相关文章
相关作者
相关机构