GB990744A - Process for producing an alkylaryl compound suitable for the preparation of biologically soft detergent - Google Patents

Process for producing an alkylaryl compound suitable for the preparation of biologically soft detergent

Info

Publication number
GB990744A
GB990744A GB46225/61A GB4622561A GB990744A GB 990744 A GB990744 A GB 990744A GB 46225/61 A GB46225/61 A GB 46225/61A GB 4622561 A GB4622561 A GB 4622561A GB 990744 A GB990744 A GB 990744A
Authority
GB
United Kingdom
Prior art keywords
alkyl group
phenol
detergents
alkyl
followed
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
GB46225/61A
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.)
Universal Oil Products Co
Original Assignee
Universal Oil Products 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 Universal Oil Products Co filed Critical Universal Oil Products Co
Publication of GB990744A publication Critical patent/GB990744A/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
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
    • 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
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3332—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
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C07C2523/04—Alkali metals
    • 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
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • 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
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126—Aluminium chloride

Landscapes

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

Abstract

Alkylbenzenes or alkyl phenols, suitable for the production of detergents, are obtained by separating from a paraffinic fraction boiling in the range 125-250 DEG C. a fraction containing at least 95% normal paraffins, converting the normal paraffins to 1-olefins or to 1-halogen compounds and with such compounds alkylating benzene, toluene, xylene, ethylbenzene, methylethylbenzene or phenol so as to introduce one alkyl group and obtain an alkylbenzene or alkyl phenol having a relatively straight-chain C9-C15 alkyl group (see Division C5). Biodegradable detergents are obtained from the alkylbenzenes by sulphonation followed by neutralization with sodium hydroxide or by nitration followed by reduction to the monoamino compound which is condensed with ethylene oxide or propylene oxide to a polyoxyalkylated detergent product containing 10-15 oxyalkylene units. Alkylphenols are directly oxyalkylated with ethylene oxide or propylene oxide to introduce 6-15 oxyalkyl units. In an example a composition is formed from 60% wt. of sodium secondary alkyl benzene sulphonate and 40% sodium sulphate, the secondary alkyl group being introduced by a n-olefin product obtained by dehydrogenation of a C11-C15 normal paraffin mixture separated from a kerosene.ALSO:Alkyl benzenes or phenols, suitable for the production of detergents, are obtained by separating from a paraffinic fraction boiling in the range 125-250 DEG C. a fraction containing at least 95% normal paraffins by a molecular sieve, urea or thiourea separation, converting the normal paraffins to 1-olefins or to 1-halogen compounds and with such compounds alkylating benzene, toluene, xylene, ethylbenzene, methylethylbenzene or phenol introducing one alkyl group to obtain an alkylbenzene or phenol having a relatively straight chain C9-C15 alkyl group. The paraffinic feed may be a straight run petroleum, Fischer-Tropsch product, hydrogenated ethylene polymer or hydrogenated fatty acid. Dehydrogenation to the olefin is effected in the presence of a non-isomerizing catalyst, e.g. a Group VIA metal oxide on a non-acidic carrier, preferably chromia on alumina with added alkali metal oxide. Halogenation is effected with chlorine or bromine at 10-50 DEG C. Subsequent alkylation is also conventional using an acidic or Friedel-Crafts catalyst. Biodegradable detergents are obtained from the alkybenzenes by sulphonation followed by neutralization with sodium hydroxide or alternatively by nitration followed by reduction to the mono-amino compound which is condensed with ethylene oxide or propylene oxide to a polyoxyalkylenated detergent product containing 10-15 oxyalkylene units. Alkylphenols are directly oxyalkylenated with ethylene oxide or propylene oxide to introduce 6-15 oxyalkylene units. In an example a composition is formed from 60% wt. of sodium secondary alkyl benzene sulphonate and 40% sodium sulphate, the secondary alkyl group being introduced by a n-olefin product obtained by dehydrogenation of a C11-C15 normal paraffin mixture separated from a kerosene.
GB46225/61A 1960-12-30 1961-12-27 Process for producing an alkylaryl compound suitable for the preparation of biologically soft detergent Expired GB990744A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US7957660A 1960-12-30 1960-12-30

Publications (1)

Publication Number Publication Date
GB990744A true GB990744A (en) 1965-04-28

Family

ID=22151422

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46225/61A Expired GB990744A (en) 1960-12-30 1961-12-27 Process for producing an alkylaryl compound suitable for the preparation of biologically soft detergent

Country Status (2)

Country Link
GB (1) GB990744A (en)
OA (1) OA00530A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5196574A (en) * 1991-12-23 1993-03-23 Uop Detergent alkylation process using a fluorided silica-alumina
WO2001002325A1 (en) * 1999-07-06 2001-01-11 Sasol Technology (Pty) Ltd. Alkylbenzenes derived from fischer-tropsch hydrocarbons and their use in drilling fluids
WO2004058921A1 (en) * 2002-12-30 2004-07-15 Shell Internationale Research Maatschappij B.V. A process for the preparation of detergents
WO2004074407A1 (en) * 2003-02-20 2004-09-02 Shell Internationale Research Maatschappij B.V. A process for the preparation of detergent compounds
US7465846B2 (en) 2003-03-10 2008-12-16 Sasol Technology (Proprietary) Limited Extraction of oxygenates from a hydrocarbon stream
US7737312B2 (en) 2003-03-10 2010-06-15 Sasol Technology (Proprietary) Limited Production of linear alkyl benzene
US7863492B2 (en) 2003-03-10 2011-01-04 Sasol Technology (Proprietary) Limited Production of linear alkyl benzene

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5196574A (en) * 1991-12-23 1993-03-23 Uop Detergent alkylation process using a fluorided silica-alumina
WO2001002325A1 (en) * 1999-07-06 2001-01-11 Sasol Technology (Pty) Ltd. Alkylbenzenes derived from fischer-tropsch hydrocarbons and their use in drilling fluids
WO2004058921A1 (en) * 2002-12-30 2004-07-15 Shell Internationale Research Maatschappij B.V. A process for the preparation of detergents
AU2003303461B2 (en) * 2002-12-30 2007-07-26 Shell Internationale Research Maatschappij B.V. A process for the preparation of detergents
US7282474B2 (en) 2002-12-30 2007-10-16 Shell Oil Company Process for the preparation of detergents
CN100358980C (en) * 2002-12-30 2008-01-02 国际壳牌研究有限公司 A process for the preparation of detergents
WO2004074407A1 (en) * 2003-02-20 2004-09-02 Shell Internationale Research Maatschappij B.V. A process for the preparation of detergent compounds
US7674940B2 (en) 2003-02-20 2010-03-09 Shell Oil Company Process for the preparation of detergent compounds
US7465846B2 (en) 2003-03-10 2008-12-16 Sasol Technology (Proprietary) Limited Extraction of oxygenates from a hydrocarbon stream
US7737312B2 (en) 2003-03-10 2010-06-15 Sasol Technology (Proprietary) Limited Production of linear alkyl benzene
US7863492B2 (en) 2003-03-10 2011-01-04 Sasol Technology (Proprietary) Limited Production of linear alkyl benzene

Also Published As

Publication number Publication date
OA00530A (en) 1966-07-15

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