GB929093A - Process for arylation of aromatic compounds - Google Patents

Process for arylation of aromatic compounds

Info

Publication number
GB929093A
GB929093A GB85561A GB85561A GB929093A GB 929093 A GB929093 A GB 929093A GB 85561 A GB85561 A GB 85561A GB 85561 A GB85561 A GB 85561A GB 929093 A GB929093 A GB 929093A
Authority
GB
United Kingdom
Prior art keywords
group
acetanilide
diphenyl
amyl nitrite
ethyl
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
GB85561A
Inventor
Ernest Bryson Mccall
Edward John Blackman
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
Publication of GB929093A publication Critical patent/GB929093A/en
Expired legal-status Critical Current

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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

Aromatic hydrocarbons are arylated by reaction with an N-acylated primary aromatic amine at an elevated temperature in the presence of a nitrosating agent preferably in the range of 40 DEG to 100 DEG C. The nitrosating agent may be an alkyl nitrite, e.g. ethyl or amyl nitrite, an oxide of nitrogen such as nitrogen trioxide (nitrous fumes which can for instance be generated in situ) or dinitrogen tetroxide, or a nitrosyl halide such as nitrosyl chloride. Specified primary aromatic amines are acetanilide, acet-p-toluidide, N-isobutyryl-b -naphthylamine, N,N1-diacetyl-p-phenylene-diamine and N,N1-diacetyl-benzidine. Specified aromatic hydrocarbons are benzene, naphthalene, indene, anthracene, diphenyl and terphenyls which may contain a substituent, e.g. a methyl, ethyl, octyl or cyclohexyl group. A diluent may be present. The aromatic hydrocarbon is generally in excess, e.g. the mol ratio to arylating agent is above 2:1. In examples acetanilide is reacted with diphenyl to give a mixture of terphenyls in the presence of amyl nitrite, "nitrous fumes", dinitrogen tetroxide and nitrosyl chloride and diphenyl is obtained by reacting benzene with acetanilide in the presence of amyl nitrite.ALSO:The invention comprises a process for the arylation of aromatic compounds in which the compound is reacted with an N-acylated primary aromatic amine at an elevated temperature in the presence of a nitrosating agent preferably in the range of 60 to 100 DEG C. The nitrosating agent may be an alkyl nitrite, e.g. ethyl or amyl nitrite, an oxide of nitrogen such as nitrogen trioxide (nitrous fumes which can for instance be generated in situ) or dinitrogen tetroxide, or a nitrosyl halide such as nitrosyl chloride. Specified primary aromatic amines are acetanilide, acet-p-toluidine, N-n-propionyl-p-phenetidine, N-isobutyrylb -naphthylamine, N,N1-diacetyl-p-phenylene-diamine. N,N1-diacetylbenzidine and 3-acetylaminopyridine. The aromatic compounds may contain more than one ring or type of ring and may contain a substituent, e.g. an aliphatic group, for instance an alkyl group, such as a methyl, ethyl or octyl group, a cycloalkyl group, such as a cyclohexyl group, or an alkoxy group, such as methoxy, ethoxy or butoxy; a halogen atom, for example chlorine or bromine; or a carboxylic ester group, for example an ethoxycarbonyl group. Many examples of aromatic compounds are given. In an example amyl nitrite was added over a period of about 1/4 hour to a solution of acetanilide in molten diphenyl at a temperature of 85 DEG C. The solution was stirred and maintained at 85 DEG and 90 DEG C. for 5 hours. Fractional distillation of the product gave unchanged diphenyl and a mixture of terphenyls which solidified to a wax-like material on cooling. In another example p-chloracetanilide and amyl nitrite were dissolved in benzene and refluxed to give p-chlordiphenyl. Other examples are given.
GB85561A 1962-06-09 1961-01-09 Process for arylation of aromatic compounds Expired GB929093A (en)

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
GB929093A true GB929093A (en) 1963-06-19

Family

ID=6975592

Family Applications (5)

Application Number Title Priority Date Filing Date
GB3842860A Expired GB919088A (en) 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds
GB3396161A Expired GB928320A (en) 1960-11-09 1960-11-09 Alkylation 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 Before (2)

Application Number Title Priority Date Filing Date
GB3842860A Expired GB919088A (en) 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds
GB3396161A Expired GB928320A (en) 1960-11-09 1960-11-09 Alkylation of aromatic compounds

Family Applications After (2)

Application Number Title Priority Date Filing Date
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) GB919088A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3270906D1 (en) * 1982-01-14 1986-06-05 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
GB959605A (en) 1964-06-03
DE1241428B (en) 1967-06-01
GB919088A (en) 1963-02-20
GB986040A (en) 1965-03-17
DE1249278B (en) 1967-09-07
GB928320A (en) 1963-06-12

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