EP1480930A1 - Production de composes aromatiques a substitution alpha-chloroisopropyle - Google Patents

Production de composes aromatiques a substitution alpha-chloroisopropyle

Info

Publication number
EP1480930A1
EP1480930A1 EP03706566A EP03706566A EP1480930A1 EP 1480930 A1 EP1480930 A1 EP 1480930A1 EP 03706566 A EP03706566 A EP 03706566A EP 03706566 A EP03706566 A EP 03706566A EP 1480930 A1 EP1480930 A1 EP 1480930A1
Authority
EP
European Patent Office
Prior art keywords
chloroisopropyl
substituted aromatics
production
substituted
aromatics
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03706566A
Other languages
German (de)
English (en)
Inventor
Gabriele Lang
Stefan HÜFFER
Arno Lange
Hans Peter Rath
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1480930A1 publication Critical patent/EP1480930A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings

Definitions

  • the present invention relates to a process for the preparation of ⁇ -chloroisopropyl-substituted aromatics.
  • Aromatics substituted by ⁇ -chloroisopropyl such as m- or p-dicumyl-10 chloride or 1,3,5-tricumyl chloride, serve as Inifer molecules for the production of linear or star-shaped telechelic polyisobutenes.
  • a complex is formed with 2 or 3 carbocationic or cationogenic centers that can attach isobutene molecules.
  • the carbocation 15 tert-butyl termini of the linear or star-shaped polyisobutenes obtained can be converted into olefinic or other functional groups, cf. e.g. EP-A 0 713 883.
  • the invention has for its object to provide a method with which ⁇ -chloro-isopropyl-substituted aromatics can be obtained in high yield and with simple work-up.
  • this object is achieved by a process for the preparation of ⁇ -chloroisopropyl-substituted aromatics of the formula I.
  • n is an integer from 2 to 4, by treating isopropenyl-substituted aromatics of the formula II
  • ⁇ -chloroisopropyl-substituted aromatics can be obtained in almost quantitative yield. This is highly surprising, since the person skilled in the art would have expected the occurrence of undesirable side reactions or the cationic polymerization of the isopropenyl-substituted aromatics (cf. 0. Nuyken et al., Loc. Cit.) In a reaction in the absence of a solvent. The success of the method according to the invention is presumably due to the fact that, in the absence of a solvent, in particular a polar solvent, carbocations, from which undesirable side reactions or polymerizations can start, are not stable.
  • the process according to the invention can be carried out in a simple manner by passing hydrogen chloride gas through the isopropenyl-substituted aromatic or by reacting it in a pressure vessel. This makes use of the fact that both the starting material and the product of the process according to the invention are liquid at the reaction temperature and the use of a solvent is not necessary.
  • the processing is usually limited to the removal of excess hydrogen chloride gas from the product, e.g. by stripping with an inert gas such as nitrogen. Losses of yield through processing steps are avoided.
  • the process according to the invention is preferably carried out at a temperature of -10 to + 50 ° C, in particular 0 to 15 ° C, and a pressure of 1 to 10 bar. It can be carried out batchwise or continuously.
  • the reaction can optionally be accelerated by using Lewis or Brönstedt acid catalysts.
  • Suitable catalysts are Lewis acids, such as aluminum trichloride, aluminum tribromide, boron trifluoride, boron trifluoride alcoholate, boron trifluoride etherate, titanium tetrachloride, tin tetrachloride, ethyl aluminum dichloride, iron trichloride, antimony pentachloride or antimony pentafluoride; Brönstedt acids, such as sulfuric acid, phosphoric acid, Trifluoromethanesulfonic acid and the like.
  • Organic protonic acids can also be present in polymer-bound form, for example as an ion exchange resin.
  • n is preferably 2 or 3.
  • Preferred isopropenyl-substituted aromatics are 1,3,5-triisopropenylbenzene, 1,4-diisopropenylbenzene and 1,3-diisopropenylbenzene, the latter being particularly preferred.
  • the benzene nucleus can carry further substituents which do not impair the reaction according to the invention, in particular C 1 -C 4 -alkyl radicals such as methyl, ethyl or t-butyl. Mixtures of various isopropenyl-substituted aromatics can also be used as starting materials for the process according to the invention.
  • the isopropenyl-substituted aromatics used as starting materials are known and e.g. by dehydration of ⁇ -hydroxyl-substituted aromatics (cf. DE-A 1 618 449), Wittig reaction on acetylbenzenes (cf. JP Kennedy et al., Polym. Bull. 1981, 4, 67-74) or dehydration from isopropylbenzenes (see JP-2001026558 and JP-2000327596).
  • the ⁇ -chloroisopropyl-substituted aromatics obtained by the process according to the invention can be used in a manner known per se for the production of homopolymers of isobutene or copolymers of isobutene with vinyl aromatics by living cationic polymerization.
  • a manner known per se for the production of homopolymers of isobutene or copolymers of isobutene with vinyl aromatics by living cationic polymerization.
  • EP-A 0713 883, DE-A 199 37 562 or DE-A 100 61 715 e.g. refer to EP-A 0713 883, DE-A 199 37 562 or DE-A 100 61 715.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés aromatiques à substitution α-chloroisopropyle qui sont obtenus, avec un rendement élevé, par traitement de composés aromatiques à substitution isopropényle avec du gaz chlorhydrique en l'absence de solvant. Les composés aromatiques à substitution α-chloroisopropyle selon l'invention servent d'initiateurs pour la polymérisation cationique d'isobutène.
EP03706566A 2002-02-25 2003-02-24 Production de composes aromatiques a substitution alpha-chloroisopropyle Withdrawn EP1480930A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10207963 2002-02-25
DE10207963A DE10207963A1 (de) 2002-02-25 2002-02-25 Herstellung von alpha-Chlorisopropyl-substituierten Aromaten
PCT/EP2003/001877 WO2003070674A1 (fr) 2002-02-25 2003-02-24 Production de composes aromatiques a substitution $g(a)-chloroisopropyle

Publications (1)

Publication Number Publication Date
EP1480930A1 true EP1480930A1 (fr) 2004-12-01

Family

ID=27674935

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03706566A Withdrawn EP1480930A1 (fr) 2002-02-25 2003-02-24 Production de composes aromatiques a substitution alpha-chloroisopropyle

Country Status (8)

Country Link
US (1) US7109387B2 (fr)
EP (1) EP1480930A1 (fr)
JP (1) JP4093366B2 (fr)
KR (1) KR20040094708A (fr)
CN (1) CN1250497C (fr)
AU (1) AU2003208754A1 (fr)
DE (1) DE10207963A1 (fr)
WO (1) WO2003070674A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007018109A1 (fr) * 2005-08-08 2007-02-15 Kaneka Corporation Procédé pour la production d'un composé aromatique chloré
AU2014212854B2 (en) 2013-01-28 2017-10-12 Henkel IP & Holding GmbH Synthesis of functional polyisobutylene-containing oligomers and polymers
JP6529961B2 (ja) * 2013-05-10 2019-06-12 ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング 官能性ポリイソブチレン含有オリゴマーおよびポリマー

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3024291A (en) * 1960-08-24 1962-03-06 Dow Chemical Co Method of making alpha-haloethyl vinylbenzenes
US4241222A (en) * 1979-09-13 1980-12-23 Pennwalt Corporation Process for the preparation of cumyl peroxides
US4767885A (en) * 1984-08-06 1988-08-30 University Of Akron Sterically hindered binifers telechelic polymers made therefrom
SU1286586A1 (ru) * 1985-09-27 1987-01-30 МГУ им.М.В.Ломоносова Способ получени смеси о-и п-изомеров ди ( @ -хлорэтил) бензола
EP0564979B1 (fr) * 1992-04-10 1996-08-28 Hoechst Aktiengesellschaft Procédé pour la fabrication de dixylylpropane
EP0713883B2 (fr) 1994-06-09 2008-10-29 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Procede de production d'un polymere d'isobutene

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03070674A1 *

Also Published As

Publication number Publication date
KR20040094708A (ko) 2004-11-10
CN1250497C (zh) 2006-04-12
JP2005517730A (ja) 2005-06-16
US20050171392A1 (en) 2005-08-04
WO2003070674A1 (fr) 2003-08-28
US7109387B2 (en) 2006-09-19
DE10207963A1 (de) 2003-09-04
JP4093366B2 (ja) 2008-06-04
AU2003208754A1 (en) 2003-09-09
CN1639093A (zh) 2005-07-13

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