GB1098236A - Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups - Google Patents

Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups

Info

Publication number
GB1098236A
GB1098236A GB5187165A GB5187165A GB1098236A GB 1098236 A GB1098236 A GB 1098236A GB 5187165 A GB5187165 A GB 5187165A GB 5187165 A GB5187165 A GB 5187165A GB 1098236 A GB1098236 A GB 1098236A
Authority
GB
United Kingdom
Prior art keywords
groups
yield
sulphur dioxide
hydrogenation
catalyst
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
GB5187165A
Inventor
Jeffrey Richards
Peter John Richardson
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB5187165A priority Critical patent/GB1098236A/en
Priority to BE690846D priority patent/BE690846A/xx
Priority to FR86500A priority patent/FR1503385A/en
Publication of GB1098236A publication Critical patent/GB1098236A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • 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
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • 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
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel

Landscapes

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

Abstract

The catalytic hydrogenation of aromatic hydrocarbons containing olefinic or acetylenic groups is effected in the presence of sulphur dioxide, whereby the tendency of the aromatic nucleus to undergo hydrogenation is reduced. The sulphur dioxide may be added as a gas or in solution. The catalyst may be a known hydrogenation catalyst, a number of which are specified, and may be supported on a carrier. An example is given of the production of ethylbenzene from styrene.ALSO:The catalytic hydrogenation of aromatic compounds containing one or more reducible groups is effected in the presence of sulphur dioxide, whereby the tendency of the aromatic nucleus to undergo hydrogenation is reduced. Specified reducible groups are nitro, nitroso and azo groups, which yield amino groups, alkenylimino and cyclo-alkenylimino groups, which yield alkylamino and cycloalkylamino groups, carbonyl groups, which yield carbinol groups, and olefinic and acetylenic groups, which yield the corresponding saturated compounds (see Division C5). The reducible group may be present initially in the compound to be reduced or it may be formed in situ, as in the reductive alkylation of primary aromatic amines in the presence of ketones. The sulphur dioxide may be added as a gas or in solution. The catalyst may be a known hydrogenation catalyst, some of which are specified, and may be supported on a carrier. Examples are given in which (1) p-aminodiphenylamine and acetone yield p-isopropylaminodiphenylamine, (2) p - aminodiphenylamine and cyclohexanone yield N-cyclohexyl - N1 - phenyl - p - phenylene diamine and (3) nitrobenzene yields aniline, sulphur dioxide and a hydrogenation catalyst being present in each case.
GB5187165A 1965-12-07 1965-12-07 Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups Expired GB1098236A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB5187165A GB1098236A (en) 1965-12-07 1965-12-07 Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups
BE690846D BE690846A (en) 1965-12-07 1966-12-07
FR86500A FR1503385A (en) 1965-12-07 1966-12-07 Catalytic reduction process for organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5187165A GB1098236A (en) 1965-12-07 1965-12-07 Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups

Publications (1)

Publication Number Publication Date
GB1098236A true GB1098236A (en) 1968-01-10

Family

ID=10461711

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5187165A Expired GB1098236A (en) 1965-12-07 1965-12-07 Improvements in the catalytic hydrogenation of aromatic compounds containing reducible groups

Country Status (1)

Country Link
GB (1) GB1098236A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023131140A1 (en) * 2022-01-04 2023-07-13 圣奥化学科技有限公司 N-(3,5,5-trimethylcyclohexyl)-n'-phenyl p-phenylenediamine, and synthesis method therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023131140A1 (en) * 2022-01-04 2023-07-13 圣奥化学科技有限公司 N-(3,5,5-trimethylcyclohexyl)-n'-phenyl p-phenylenediamine, and synthesis method therefor

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