WO1991008182A1 - Ameliorations relatives a la reduction de composes organiques halogenes - Google Patents

Ameliorations relatives a la reduction de composes organiques halogenes Download PDF

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Publication number
WO1991008182A1
WO1991008182A1 PCT/GB1990/001904 GB9001904W WO9108182A1 WO 1991008182 A1 WO1991008182 A1 WO 1991008182A1 GB 9001904 W GB9001904 W GB 9001904W WO 9108182 A1 WO9108182 A1 WO 9108182A1
Authority
WO
WIPO (PCT)
Prior art keywords
process according
reduction
cyclic hydrocarbon
organic compounds
relating
Prior art date
Application number
PCT/GB1990/001904
Other languages
English (en)
Inventor
John Parry Davey
David Edward Cozens
Original Assignee
Rhone-Poulenc Chemicals Limited
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 Rhone-Poulenc Chemicals Limited filed Critical Rhone-Poulenc Chemicals Limited
Publication of WO1991008182A1 publication Critical patent/WO1991008182A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation

Definitions

  • This invention relates to the reduction of halogenated organic compounds, and more specifically to the reduction of halogenated aliphatic compounds containing chlorine and fluorine substituents such as chloro-fluoro- methanes, -ethanes or propanes.
  • this invention provides a process for the reduction of a halogenated aliphatic group containing compound wherein the compound is reacted with a cyclic compound, which is capable of being converted to an aromatic compound by dehydrogenation, in the liquid phase and in the presence of a hydrogenation catalyst.
  • the process of the invention is preferably applied to halogenated aliphatic compounds and, especially, chlorofluoro-ethanes or chlorofluorohydro-ethanes.
  • the preferred cyclic compound which does, in effect, behave as a hydrogen-donor, is a cycloalkane or cycloalkene, or an alkyl substituted cycloalkane (or cycloalkene) , typically decalin, tetralin, cyclohexane, cyclohexene, or limonene.
  • the preferred hydrogenation catalyst is a group VIII metal, in general a noble metal/precious metal- which can either be used on an inert support e.g. carbon or alumina or in solution as a metal/organic complex. Palladium is the preferred catalyst.
  • the reaction to which this invention is most applicable is the replacement of a chlorine atom by hydrogen in a chlorofluoroethane, such as l,l-dichloro-1,2,2,2,- tetrafluoroethane (CC1 2 F.CF 3 ) or in a hydrochlorofluoroethane such as 1-chloro-l,2,2,2,-tetrafluoroethane (CHC1F.CF 3 ) .
  • the hydrogen-donor will be oxidised in the course of the reaction and may be reduced back to its original state in a separate stage.
  • the reaction can be carried out at moderate temperatures (e.g. 200°-300°C) and at moderate pressures (e.g. 200 to 750 psig) , so that the reaction occurs principally in the liquid phase, rather than in the gas phase.
  • Example 1 The process described in Example 1 was repeated using other hydrogen donor solvents, but with the same substrate, CHCIF.CF 3 .
  • the conditions used, and the results obtained, are given in the following Examples.

Landscapes

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

Abstract

Procédé de réduction d'un composé aliphatique halogéné, consistant à le faire réagir avec un hydrocarbure cyclique pouvant être transformé en un composé aromatique par déshydrogénation, dans la phase liquide, en présence d'un catalyseur d'hydrogénation en métal du groupe VIII.
PCT/GB1990/001904 1989-12-06 1990-12-06 Ameliorations relatives a la reduction de composes organiques halogenes WO1991008182A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898927580A GB8927580D0 (en) 1989-12-06 1989-12-06 Improvements in or relating to the reduction of halogenated organic compounds
GB8927580.4 1989-12-06

Publications (1)

Publication Number Publication Date
WO1991008182A1 true WO1991008182A1 (fr) 1991-06-13

Family

ID=10667512

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1990/001904 WO1991008182A1 (fr) 1989-12-06 1990-12-06 Ameliorations relatives a la reduction de composes organiques halogenes

Country Status (2)

Country Link
GB (2) GB8927580D0 (fr)
WO (1) WO1991008182A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199066A1 (fr) * 1985-03-20 1986-10-29 BASF Aktiengesellschaft Procédé de déshalogénation réductive de composés halogénés
EP0253410A1 (fr) * 1986-07-18 1988-01-20 AUSIMONT S.p.A. Procédé pour la préparation de fluoroéthylènes et de chlorofluoroéthylènes contenant de hydrogène à partir de chlorofluoroéthanes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1578933A (en) * 1977-05-24 1980-11-12 Ici Ltd Manufacture of halogenated hydrocarbons
IT1221776B (it) * 1988-01-15 1990-07-12 Ausimont Spa Processo per la preparazione di 1,2 difluoroetano e di 1,1,2 trifluoroetano
US4996379A (en) * 1988-05-30 1991-02-26 Central Glass Company, Limited Method of preparing 1,1,1,2-tetrafluoroethane from 1,1-dichloro-1,2,2,2-tetrafluoroethane
DE68912657T2 (de) * 1988-06-21 1994-09-01 Asahi Glass Co Ltd Verfahren zur Herstellung von 1,1,1,2-Tetrafluorethan.
GB2228505B (en) * 1989-01-18 1992-07-08 Nat Oilwell A hanger

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199066A1 (fr) * 1985-03-20 1986-10-29 BASF Aktiengesellschaft Procédé de déshalogénation réductive de composés halogénés
EP0253410A1 (fr) * 1986-07-18 1988-01-20 AUSIMONT S.p.A. Procédé pour la préparation de fluoroéthylènes et de chlorofluoroéthylènes contenant de hydrogène à partir de chlorofluoroéthanes

Also Published As

Publication number Publication date
GB2243606A (en) 1991-11-06
GB9026574D0 (en) 1991-01-23
GB8927580D0 (en) 1990-02-07

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