GB928320A - Alkylation of aromatic compounds - Google Patents

Alkylation of aromatic compounds

Info

Publication number
GB928320A
GB928320A GB3396161A GB3396161A GB928320A GB 928320 A GB928320 A GB 928320A GB 3396161 A GB3396161 A GB 3396161A GB 3396161 A GB3396161 A GB 3396161A GB 928320 A GB928320 A GB 928320A
Authority
GB
United Kingdom
Prior art keywords
sulphonyl
methyl
aromatic compound
sulphonyl chloride
chloride
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
GB3396161A
Inventor
Ernest Bryson Mccall
Ryland James Roberts
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.)
Monsanto Chemicals Ltd
Original Assignee
Monsanto Chemicals 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 Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
Priority to DE1961M0050784 priority Critical patent/DE1176143B/en
Publication of GB928320A publication Critical patent/GB928320A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/868—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains sulfur as hetero-atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • 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
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • 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
    • C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/42—Platinum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/72—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides

Landscapes

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

Abstract

Alkyl, including substituted alkyl and cycloalkyl, groups are introduced into an aromatic compound by reacting the latter with a compound containing linked to an aliphatic carbon atom a sulphonyl halide group, a sulphonic acid group or a salt, e.g. ammonium salt, of the latter which decomposes at reaction temperature. The aromatic compound may contain condensed benzene rings and either the aromatic compound or alkalating agent may contain as substituents alkyl or aryl groups. Specified alkylating agents are methyl and ethyl sulphonyl chloride, methyl sulphonyl bromide, methyl sulphonic acid, ammonium methyl sulphonate, benzyl sulphonyl chloride and cyclohexyl sulphonyl bromide. The reaction is effected at 125 DEG -300 DEG C. in the liquid phase in the presence of a solvent, e.g. hexachlorobenzene, if desired, for 2-30 hours using a molar ratio or aromatic compound to alkylating agent of 1-25:1. An example describes the preparation of (1) hexyldiphenyls from diphenyl and n-hexyl sulphonyl chloride.ALSO:Alkyl, including substituted alkyl and cycloalkyl, groups are introduced into an aromatic (carbocyclic or heterocyclic) compound by reacting the latter with a compound containing linked to an aliphatic carbon atom a sulphonyl halide group, a sulphonic acid group or a salt, e.g. ammonium salt, of the latter which decomposes at reaction temperature. The aromatic compound may be carbocyclic or heterocyclic, e.g. containing a furan, thiophene or pyridine ring possibly with one or more condensed benzene rings and either the aromatic compound or alkylating agent may contain as substituents alkyl, aryl, halogen, carboxylic ester, alkoxy or aryloxy groups. Specified alkylating agents are methyl and ethyl sulphonyl chloride, methyl sulphonyl bromide, monochloro-methyl, monofluoromethyl and trichloromethyl sulphonyl chloride, methyl sulphonic acid, ammonium methyl sulphonate, benzyl sulphonyl chloride, cyclohexyl sulphonyl bromide and pentafluoroethyl sulphonyl chloride. The reaction is effected at 125-300 DEG C. in the liquid phase in the presence of a solvent, e.g. hexachlorobenzene, if desired, for 2-30 hours using a molar ratio of aromatic compound to alkylating agent of 1-25:1. The examples describe the preparations of (1) hexyldiphenyls from diphenyl and n-hexyl sulphonyl chloride, (2) trichloromethyldiphenyl which may be hydrolysed to p-phenylbenzoic acid, from diphenyl and trichloromethyl sulphonyl chloride and (3) benzyldibenzothiophenes from dibenzothiophene and benzylsulphonyl chloride.
GB3396161A 1960-11-09 1960-11-09 Alkylation of aromatic compounds Expired GB928320A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1961M0050784 DE1176143B (en) 1960-11-09 1961-11-06 Process for the nucleus alkylation of aromatic or heteroaromatic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1962B0067625 DE1241428B (en) 1962-06-09 1962-06-09 Process for the chloromethylation of aromatic compounds

Publications (1)

Publication Number Publication Date
GB928320A true GB928320A (en) 1963-06-12

Family

ID=6975592

Family Applications (5)

Application Number Title Priority Date Filing Date
GB3396161A Expired GB928320A (en) 1960-11-09 1960-11-09 Alkylation of aromatic compounds
GB3842860A Expired GB919088A (en) 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds
GB85561A Expired GB929093A (en) 1962-06-09 1961-01-09 Process for arylation of aromatic compounds
GB3628761A Expired GB959605A (en) 1961-10-10 1961-10-10 Process for the arylation of aromatic compounds
GB2284963A Expired GB986040A (en) 1962-06-09 1963-06-07 Improvements in the chloromethylation of aromatic compounds

Family Applications After (4)

Application Number Title Priority Date Filing Date
GB3842860A Expired GB919088A (en) 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds
GB85561A Expired GB929093A (en) 1962-06-09 1961-01-09 Process for arylation of aromatic compounds
GB3628761A Expired GB959605A (en) 1961-10-10 1961-10-10 Process for the arylation of aromatic compounds
GB2284963A Expired GB986040A (en) 1962-06-09 1963-06-07 Improvements in the chloromethylation of aromatic compounds

Country Status (2)

Country Link
DE (2) DE1241428B (en)
GB (5) GB928320A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084194B1 (en) * 1982-01-14 1986-04-30 MERCK PATENT GmbH Liquid crystal mixtures
US4978811A (en) * 1988-04-01 1990-12-18 The Dow Chemical Company Process for hydrolysis of ortho-aromatic di-aryl ethers
US6531609B2 (en) * 2000-04-14 2003-03-11 Hoffmann-La Roche Inc. Process for the preparation of thiazolidinedione derivatives

Also Published As

Publication number Publication date
DE1241428B (en) 1967-06-01
GB929093A (en) 1963-06-19
GB919088A (en) 1963-02-20
DE1249278B (en) 1967-09-07
GB959605A (en) 1964-06-03
GB986040A (en) 1965-03-17

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