WO2012055754A3 - Method for the production of 1-methylcyclopentane derivatives - Google Patents

Method for the production of 1-methylcyclopentane derivatives Download PDF

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Publication number
WO2012055754A3
WO2012055754A3 PCT/EP2011/068328 EP2011068328W WO2012055754A3 WO 2012055754 A3 WO2012055754 A3 WO 2012055754A3 EP 2011068328 W EP2011068328 W EP 2011068328W WO 2012055754 A3 WO2012055754 A3 WO 2012055754A3
Authority
WO
WIPO (PCT)
Prior art keywords
methylcyclopentene
production
methylcyclopentane
derivatives
reaction
Prior art date
Application number
PCT/EP2011/068328
Other languages
German (de)
French (fr)
Other versions
WO2012055754A2 (en
Inventor
Andreas Lanver
Klaus Ebel
Rainer Klopsch
Werner Bertleff
Richard Dehn
Joaquim Henrique Teles
Helmut Kronemayer
Marcus Georg Schrems
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 WO2012055754A2 publication Critical patent/WO2012055754A2/en
Publication of WO2012055754A3 publication Critical patent/WO2012055754A3/en

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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
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/29—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of carbon atoms in a ring while maintaining the number of rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency

Landscapes

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

Abstract

The invention relates to a method for the production of 1-methylcyclopentene by the thermal reaction of cyclohexanol or cyclohexene or mixtures of both compounds to 1-methylcyclopentene, characterized in that the obtained byproducts 3-methylcyclopentene and 4-methylcyclopentene (double bond isomers of 1-methylcyclopentene) are fed back to the reaction.
PCT/EP2011/068328 2010-10-25 2011-10-20 Method for the production of 1-methylcyclopentane derivatives WO2012055754A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10188692 2010-10-25
EP10188692.7 2010-10-25

Publications (2)

Publication Number Publication Date
WO2012055754A2 WO2012055754A2 (en) 2012-05-03
WO2012055754A3 true WO2012055754A3 (en) 2012-08-30

Family

ID=45509416

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/068328 WO2012055754A2 (en) 2010-10-25 2011-10-20 Method for the production of 1-methylcyclopentane derivatives

Country Status (1)

Country Link
WO (1) WO2012055754A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8993819B2 (en) 2011-07-12 2015-03-31 Basf Se Process for preparing cycloheptene
US9193862B2 (en) 2012-02-22 2015-11-24 Basf Se Blends for composite materials

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2333903A (en) * 1939-06-05 1943-11-09 Universal Oil Prod Co Treatment of hydrocarbons
US2485966A (en) * 1947-09-29 1949-10-25 Shell Dev Methylcyclopentene production
US4661639A (en) * 1984-05-25 1987-04-28 Asahi Kasei Kogyo Kabushiki Kaisha Process for producing cyclic alcohol
US5498802A (en) * 1995-02-28 1996-03-12 Hoechst Celanese Corporation Process for preparing omega-halo-ketones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2333903A (en) * 1939-06-05 1943-11-09 Universal Oil Prod Co Treatment of hydrocarbons
US2485966A (en) * 1947-09-29 1949-10-25 Shell Dev Methylcyclopentene production
US4661639A (en) * 1984-05-25 1987-04-28 Asahi Kasei Kogyo Kabushiki Kaisha Process for producing cyclic alcohol
US5498802A (en) * 1995-02-28 1996-03-12 Hoechst Celanese Corporation Process for preparing omega-halo-ketones

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; STRUCKMANN, LIISA K.: "Equilibrium and kinetic studies on etherification: reactions of C5 and C6 alkenes with methanol and ethanol", XP002677916, retrieved from STN Database accession no. 1997:389754 *
GARSON A. LUTZ ET AL: "Studies in the Methylcyclopentane Series. I. Preparation and Reactions of Methylcyclopentyl Monochlorides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 70, no. 12, 19 December 1948 (1948-12-19), pages 4135 - 4138, XP055029990, ISSN: 0002-7863, DOI: 10.1021/ja01192a047 *
HOMER ADKINS ET AL: "Isomerization of Cyclohexenes to Cyclopentenes: Oxidation of These Alkenes to Glycols and Acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 70, no. 12, 19 December 1948 (1948-12-19), pages 4041 - 4045, XP055029571, ISSN: 0002-7863, DOI: 10.1021/ja01192a021 *
PATRICK MAGNOUX ET AL: "Formation de coke, desactivation et regeneration des zeolithes. IV - Transfert d'hydrogène et formation de coke au cours de la transformation du cyclohexene sur une zeolithe USHY. Influence de la temperature de reaction", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, SOCIETE FRANCAISE DE CHIMIE. PARIS, FRANCE, no. 5, 1 January 1987 (1987-01-01), pages 810 - 814, XP009160175, ISSN: 0037-8968 *
STRUCKMANN, LIISA K.: "Equilibrium and kinetic studies on etherification: reactions of C5 and C6 alkenes with methanol and ethanol", ACTA POLYTECHNICA SCANDINAVICA, CHEMICAL TECHNOLOGY SERIES , 246, 43 PP. CODEN: APSCF4, 1997 *

Also Published As

Publication number Publication date
WO2012055754A2 (en) 2012-05-03

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