GB860839A - Improvements relating to the production of alkyl aryl compounds - Google Patents

Improvements relating to the production of alkyl aryl compounds

Info

Publication number
GB860839A
GB860839A GB3897758A GB3897758A GB860839A GB 860839 A GB860839 A GB 860839A GB 3897758 A GB3897758 A GB 3897758A GB 3897758 A GB3897758 A GB 3897758A GB 860839 A GB860839 A GB 860839A
Authority
GB
United Kingdom
Prior art keywords
vol
hydrogenation
product
alumina
alkyl aryl
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
GB3897758A
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.)
FREDERICK WILLIAM BERTRAM PORT
JOHN GILBERT HALE
BP PLC
Original Assignee
FREDERICK WILLIAM BERTRAM PORT
JOHN GILBERT HALE
BP PLC
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
Priority to BE585292D priority Critical patent/BE585292A/xx
Priority to NL245989D priority patent/NL245989A/xx
Application filed by FREDERICK WILLIAM BERTRAM PORT, JOHN GILBERT HALE, BP PLC filed Critical FREDERICK WILLIAM BERTRAM PORT
Priority to GB3897758A priority patent/GB860839A/en
Publication of GB860839A publication Critical patent/GB860839A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • 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
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
    • C07C5/41—Catalytic processes
    • C07C5/412—Catalytic processes with metal oxides or metal sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • 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
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/26—Chromium
    • 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
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel
    • 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
    • C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
    • C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/85—Chromium, molybdenum or tungsten
    • C07C2523/88—Molybdenum
    • C07C2523/882—Molybdenum and cobalt
    • 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
    • C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
    • C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/85—Chromium, molybdenum or tungsten
    • C07C2523/888—Tungsten
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/04—Sulfides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Alkyl aryl hydrocarbons are formed by catalytic dehydrocyclization of straight-chain paraffins or olefins containing 14 to 26 carbon atoms per molecule at 370-580 DEG C. and thereafter selectively hydrogenating olefinic double bonds in the alkyl aryl hydrocarbons without substantial hydrogenation of the aromatic nuclei: the product may be sulphonated. The feed may be obtained by urea adduction or solvent extraction of a gas oil. Hydrodesulphurization may precede or follow this separation or may be combined with the dehydrocyclization or with the selective hydrogenation. Desulphurization may be effected over cobalt and molybdenum oxides on alumina at 100-1000 p.s.i.g., 500-900 DEG F., 1-10 vol./vol./hr. and 500-800 SCF hydrogen per barrel. Dehydrocyclization catalysts are cobalt and molybdenum oxides on alumina, nickel on alumina or a chromia-alumina catalyst promoted with a rare earth, bismuth, boron, germanium, nickel, manganese, iron, or beryllium, together with potassium, or a spinel, suitable conditions being up to 50 p.s.i.g., and 0.1-1 vol./vol./hr. with or without added or recycle hydrogen. Hydrogenation may be effected over nickel, platinum, palladium, or cobalt and molybdenum oxides on alumina or tungsten and nickel oxides or sulphides at 100-1000 p.s.i.g., 100-480 DEG C., 0.5-8 vol./vol./hr., and 500-8000 SCF hydrogen per barrel. Preferably the product is distilled either before or after the selective hydrogenation to obtain a heart cut boiling in the range 260-410 DEG C. and after hydrogenation is solvent extracted, non-aromatics being recycled, e.g. with diethylene glycol, furfural or sulphur dioxide-benzole, or aromatics are separated by adsorption on silica gel. The product may be sulphonated and neutralized and after drying may be mixed with sodium phosphates, sodium silicate and carboxymethyl cellulose.ALSO:Detergent compositions containing sodium phosphates, sodium sulphate, sodium silicate and carboxymethylcellulose also contain alkylaryl sulphonates prepared by the sulphonation of alkyl aryl hydrocarbons which are formed by catalytically dehydrocyclization of straight-chain paraffins or olefins containing 14-26 carbon atoms per molecule followed by selective hydrogenation of olefinic bonds without hydrogenation of the aromatic nuclei in the alkyl aryl hydrocarbons (see Group IV (b)). The starting material may be obtained from a gas oil which is desulphurized before or after separating the straight-chain paraffins or olefines. After aromatization and selective hydrogenation, the product is distilled to separate a cut boiling in the range 260-410 DEG C., aromatics separated out by solvent extraction with diethylene glycol, furfural, or sulphur dioxide/benzole, the resulting product sulphonated, and the sulphonated product neutralized with caustic soda.
GB3897758A 1958-12-03 1958-12-03 Improvements relating to the production of alkyl aryl compounds Expired GB860839A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE585292D BE585292A (en) 1958-12-03
NL245989D NL245989A (en) 1958-12-03
GB3897758A GB860839A (en) 1958-12-03 1958-12-03 Improvements relating to the production of alkyl aryl compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3897758A GB860839A (en) 1958-12-03 1958-12-03 Improvements relating to the production of alkyl aryl compounds

Publications (1)

Publication Number Publication Date
GB860839A true GB860839A (en) 1961-02-08

Family

ID=10406864

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3897758A Expired GB860839A (en) 1958-12-03 1958-12-03 Improvements relating to the production of alkyl aryl compounds

Country Status (3)

Country Link
BE (1) BE585292A (en)
GB (1) GB860839A (en)
NL (1) NL245989A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100506381C (en) * 2006-11-02 2009-07-01 中国石油化工股份有限公司 Macropore capacity ultra-fine nickel catalyst for selective hydrogenation
CN100506379C (en) * 2006-11-02 2009-07-01 中国石油化工股份有限公司 Macropore capacity sulfur-containing nickel catalyst for selective hydrogenation
CN101191078B (en) * 2006-11-21 2011-07-13 中国石油化工股份有限公司 Nickel catalyst with composite pore structure used for selective hydrogenation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100506381C (en) * 2006-11-02 2009-07-01 中国石油化工股份有限公司 Macropore capacity ultra-fine nickel catalyst for selective hydrogenation
CN100506379C (en) * 2006-11-02 2009-07-01 中国石油化工股份有限公司 Macropore capacity sulfur-containing nickel catalyst for selective hydrogenation
CN101191078B (en) * 2006-11-21 2011-07-13 中国石油化工股份有限公司 Nickel catalyst with composite pore structure used for selective hydrogenation

Also Published As

Publication number Publication date
NL245989A (en)
BE585292A (en)

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