The synthesis of a hydrocarbon-soluble organolithium anionic initiator. A gas-liquid chromatography study of the efficiency of the reaction of s- butyllithium with p-divinylbenzene

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dc.contributor.authorSanderson R.D.
dc.contributor.authorCosta G.
dc.contributor.authorSummers G.J.
dc.contributor.authorSummers C.A.
dc.date.accessioned2011-05-15T16:02:18Z
dc.date.available2011-05-15T16:02:18Z
dc.date.issued1999
dc.description.abstractThe extent of conversion of the reaction between sec-butyllithium and p- divinylbenzene was evaluated by quantitative gas-liquid chromatography. The reaction of stoichiometric amounts of ultra-high purity sec-butyllithium with pure p-divinylbenzene at 0°C produces an anionic initiator, 1,4-bis(1- lithio-3-methylpentyl)benzene, 2, in essentially quantitative yields, with low concentrations of monofunctional impurities. Upon the addition of 10 mol% excess of triethylamine to sec-butyllithium, the reaction of sec-butyllithium with p-divinylbenzene at 0°C yielded a homogeneous product with composition of 96% difunctionality and 4% monofunctionality, with the total disappearance of p-divinylbenzene as observed by GLC. The high purity 1,4-bis(1-lithio-3- methylpentyl)benzene initiator, 2, is an effective initiator for 1,3- butadiene polymerizations in hydrocarbon solvents and allows the synthesis of polybutadienes with microstructures ranging from 13% to 16% 1,2-vinyl content, as observed by 1H NMR analysis.The extent of conversion of the reaction between sec-butyllithium and p-divinylbenzene was evaluated by quantitative gas-liquid chromatography. The reaction of stoichiometric amounts of ultra-high purity sec-butyllithium with pure p-divinylbenzene at 0 °C produces an anionic initiator, 1,4-bis(1-lithio-3-methylpentyl)benzene, 2, in essentially quantitative yields, with low concentrations of monofunctional impurities. Upon the addition of 10 mol% excess of triethylamine to sec-butyllithium, the reaction of sec-butyllithium with p-divinylbenzene at 0 °C yielded a homogeneous product with composition of 96% difunctionality and 4% monofunctionality, with the total disappearance of p-divinylbenzene as observed by GLC. The high purity 1,4-bis(1-lithio-3-methylpentyl)benzene initiator, 2, is an effective initiator for 1,3-butadiene polymerizations in hydrocarbon solvents and allows the synthesis of polybutadienes with microstructures ranging from 13% to 16% 1,2-vinyl content, as observed by 1H NMR analysis.
dc.description.versionArticle
dc.identifier.citationPolymer
dc.identifier.citation40
dc.identifier.citation19
dc.identifier.issn323861
dc.identifier.other10.1016/S0032-3861(98)00762-9
dc.identifier.urihttp://hdl.handle.net/10019.1/12408
dc.subjectAmines
dc.subjectAnionic polymerization
dc.subjectBenzene
dc.subjectGas chromatography
dc.subjectLithium compounds
dc.subjectMicrostructure
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectOrganic solvents
dc.subjectOrganometallics
dc.subjectPolybutadienes
dc.subjectStoichiometry
dc.subjectSynthesis (chemical)
dc.subjectButyllithium
dc.subjectDivinylbenzene
dc.subjectGas-liquid chromatography
dc.subjectInitiators (chemical)
dc.subject1,3 butadiene
dc.subjectbenzene derivative
dc.subjecthydrocarbon
dc.subjectorganolithium compound
dc.subjecttriethylamine
dc.subjectarticle
dc.subjectchemical reaction
dc.subjectgas liquid chromatography
dc.subjectpolymerization
dc.subjectproton nuclear magnetic resonance
dc.subjectpurification
dc.subjectreaction analysis
dc.subjectsynthesis
dc.titleThe synthesis of a hydrocarbon-soluble organolithium anionic initiator. A gas-liquid chromatography study of the efficiency of the reaction of s- butyllithium with p-divinylbenzene
dc.typeArticle
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