GB685079A - Improvements in or relating to the dealkylation of aromatic compounds - Google Patents

Improvements in or relating to the dealkylation of aromatic compounds

Info

Publication number
GB685079A
GB685079A GB16945/50A GB1694550A GB685079A GB 685079 A GB685079 A GB 685079A GB 16945/50 A GB16945/50 A GB 16945/50A GB 1694550 A GB1694550 A GB 1694550A GB 685079 A GB685079 A GB 685079A
Authority
GB
United Kingdom
Prior art keywords
compounds
catalyst
naphthalene
aromatic
alicyclic
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
GB16945/50A
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
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 Standard Oil Development Co filed Critical Standard Oil Development Co
Publication of GB685079A publication Critical patent/GB685079A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/367Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/08Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
    • C07C4/12Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
    • C07C4/14Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
    • C07C4/20Hydrogen being formed in situ, e.g. from steam
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/321Catalytic processes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/18Carbon
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Simultaneous dealkylation of an alkylated aromatic compound and dehydrogenation of an alicyclic hydrocarbon are effected by contacting the compounds, in the vapour phase, at 250-650 DEG , especially 500-600 DEG C., in the presence of a cracking catalyst, preferably activated carbon. Hydrogen from the alicyclic hydrocarbon combines with the alkyl group to form a paraffin. The products should be removed as formed. The alicyclic hydrocarbons generally have 5 or more alicyclic carbons and are more saturated than the compounds being dealkylated. Examples are cyclopentane, cyclotetralin, hydrindene, and compounds having unsaturation in the ring or side chain. Naphthenes give aromatics or cyclo-olefins. The alkylated aromatic compounds may be benzenoid p or polycyclic hydrocarbons, e.g. diphenyl naphthalene, anthracene or phenanthrene derivatives. The carbon used as catalyst may be from vegetable, petroleum or like sources or from pure organic compounds, and activated with steam or other inert gas. Metallic oxides or salts may be present. A molar ratio of naphthalene to aromatic compound of about 1 : 1-3 is employed. The partial pressure of hydrogen should be less than about 150 p.s.i. Total feed rates are normally 0.1-10 liquid vols./vol./hour. Fixed or moving catalyst bed or fluidized operation may be employed. Examples relate to the reaction of cyclohexane, cyclopentane, their methyl derivatives, or naphthenic naphthas, with toluene, ethyl benzene, methyl naphthalene, xylenes, C9 aromatic fraction, aromatic kerosene extracts or m, p-cresols, with activated bituminous or coconut charcoal or iron oxide-pumice as catalyst.
GB16945/50A 1949-07-26 1950-07-06 Improvements in or relating to the dealkylation of aromatic compounds Expired GB685079A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US685079XA 1949-07-26 1949-07-26

Publications (1)

Publication Number Publication Date
GB685079A true GB685079A (en) 1952-12-31

Family

ID=22083022

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16945/50A Expired GB685079A (en) 1949-07-26 1950-07-06 Improvements in or relating to the dealkylation of aromatic compounds

Country Status (1)

Country Link
GB (1) GB685079A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3102151A (en) * 1958-06-13 1963-08-27 American Cyanamid Co Process for the dealkylation of alkyl naphthalene
US3517076A (en) * 1966-02-14 1970-06-23 Monsanto Co Thermal hydrodealkylation of alkyl aromatic hydrocarbons

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3102151A (en) * 1958-06-13 1963-08-27 American Cyanamid Co Process for the dealkylation of alkyl naphthalene
US3517076A (en) * 1966-02-14 1970-06-23 Monsanto Co Thermal hydrodealkylation of alkyl aromatic hydrocarbons

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