GB1345203A - Synthesis of thiophenes - Google Patents

Synthesis of thiophenes

Info

Publication number
GB1345203A
GB1345203A GB1345203DA GB1345203A GB 1345203 A GB1345203 A GB 1345203A GB 1345203D A GB1345203D A GB 1345203DA GB 1345203 A GB1345203 A GB 1345203A
Authority
GB
United Kingdom
Prior art keywords
thiophene
methyl
ethyl
thiophenes
pentan
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.)
Expired
Application number
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.)
MIDLAND YORKSHIRE HOLDINGS Ltd
Original Assignee
MIDLAND YORKSHIRE HOLDINGS Ltd
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 MIDLAND YORKSHIRE HOLDINGS Ltd filed Critical MIDLAND YORKSHIRE HOLDINGS Ltd
Publication of GB1345203A publication Critical patent/GB1345203A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C07D333/10—Thiophene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

1345203 Thiophenes MIDLAND-YORKSHIRE HOLDINGS Ltd 10 May 1972 [27 May 1971] 17574/71 Heading C2C Thiophenes are produced by reacting a compound containing at least 4 carbon atoms in a chain linked by single or double bonds and in which two of the carbon atoms may form part of an aromatic or heterocyclic ring system with carbon disulphide in the vapour phase at a temperature above 350‹ C. and in the presence of an oxidation, dehydrogenation or dehydration catalyst. Particularly preferred catalysts are those of chromia or alumina, manganese oxide or molybdenum oxide preferably promoted with potassium or sodium. The starting material may be, for example, a hydrocarbon, an alcohol, an aldehyde or a ketone. Examples describe the conversion of (a) 3-methylbutan-1- ol to 3-methyl thiophene, (b) n-butanol to thiophene; (c) pentan-1-ol to 2-methyl thiophene; (d) 2-methyl butene-1 to 3-methyl thiophene; (e) 1,4-butane diol to tetrahydrothiophene; (f) pentan-2-ol to 2-methyl thiophene; (g) 2-ethyl butan-1-ol to 3-ethyl thiophene; (h) hexan-1-ol to 2,5-dimethyl thiophene; (j) heptan-1-ol to a mixture of 2-methyl-5-ethyl thiophene and 2-n-propyl thiophene; (k) octan-1-ol to 2-nbutyl thiophene and 2-methyl-5-propyl thiophene; (1) 3-methyl-butan-1-ol to 3-methyl thiophene; (m) isoprene to 3-methyl thiophene; (n) sec-butyl-benzene to 3-phenyl thiophene; (p) methyl isobutyl ketone to 2,4-dimethyl thiophene; (q) n-pentane to 2-methyl thiophene; (r) 3-methylbutanol to 3-methyl thiophene; (s) crotonaldehyde to thiophene and (t) ethyl benzene to benzo-[b]-thiophene.
GB1345203D 1971-05-27 1971-05-27 Synthesis of thiophenes Expired GB1345203A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1757471 1971-05-27

Publications (1)

Publication Number Publication Date
GB1345203A true GB1345203A (en) 1974-01-30

Family

ID=10097578

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1345203D Expired GB1345203A (en) 1971-05-27 1971-05-27 Synthesis of thiophenes

Country Status (11)

Country Link
JP (1) JPS5212194B1 (en)
BE (1) BE783936A (en)
CH (1) CH543529A (en)
DE (1) DE2225443C3 (en)
ES (1) ES403184A1 (en)
FR (1) FR2139177B1 (en)
GB (1) GB1345203A (en)
HU (1) HU169359B (en)
IT (1) IT958049B (en)
NL (1) NL169740C (en)
SE (1) SE387948B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783541A (en) * 1984-09-13 1988-11-08 Hoechst Aktiengesellschaft Process for isomerizing alkylthiophenes
EP0751139A1 (en) * 1995-06-28 1997-01-02 Shell Internationale Researchmaatschappij B.V. Thiophene synthesis
EP0751138A1 (en) * 1995-06-28 1997-01-02 Shell Internationale Researchmaatschappij B.V. Thiophene synthesis

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783541A (en) * 1984-09-13 1988-11-08 Hoechst Aktiengesellschaft Process for isomerizing alkylthiophenes
EP0751139A1 (en) * 1995-06-28 1997-01-02 Shell Internationale Researchmaatschappij B.V. Thiophene synthesis
EP0751138A1 (en) * 1995-06-28 1997-01-02 Shell Internationale Researchmaatschappij B.V. Thiophene synthesis

Also Published As

Publication number Publication date
FR2139177B1 (en) 1973-07-13
DE2225443B2 (en) 1979-03-08
BE783936A (en) 1972-11-27
IT958049B (en) 1973-10-20
NL7207194A (en) 1972-11-29
DE2225443C3 (en) 1979-10-31
SE387948B (en) 1976-09-20
JPS5212194B1 (en) 1977-04-05
NL169740B (en) 1982-03-16
DE2225443A1 (en) 1973-01-11
FR2139177A1 (en) 1973-01-05
HU169359B (en) 1976-11-28
NL169740C (en) 1982-08-16
ES403184A1 (en) 1975-05-16
CH543529A (en) 1973-10-31

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Legal Events

Date Code Title Description
PS Patent sealed
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee