GB936882A - The preparation of a biodegradable detergent - Google Patents

The preparation of a biodegradable detergent

Info

Publication number
GB936882A
GB936882A GB27234/61A GB2723461A GB936882A GB 936882 A GB936882 A GB 936882A GB 27234/61 A GB27234/61 A GB 27234/61A GB 2723461 A GB2723461 A GB 2723461A GB 936882 A GB936882 A GB 936882A
Authority
GB
United Kingdom
Prior art keywords
chain
aromatic hydrocarbon
aluminium
predominantly straight
alkyl
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
GB27234/61A
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB936882A publication Critical patent/GB936882A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • 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
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
    • 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
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/68—Catalytic processes with halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
    • C07C309/31—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups by alkyl groups containing at least three carbon atoms
    • 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
    • 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
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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

Hydrocarbons of formula <FORM:0936882/III/1> wherein Ar is an aromatic hydrocarbon group of which the nucleus is directly linked to the quaternary carbon atom, R is predominantly straight-chain C3-6 alkyl and R1 is predominantly straight-chain C5-8 alkyl, are produced by dimerizing in presence of an aluminium alkyl catalyst one or more C5-8 predominantly straight-chain alpha-olefins containing on their non-ethylenic carbon atoms on the average less than 0,5 equivalent side-chain methyl groups and alkylating an aromatic hydrocarbon (e.g. benzene or toluene) with the dimers. The C5-8 olefin feed stocks may be obtained from (a) low severity steam cracking of wax, petrolatum or a paraffinic gas oil, (b) liquid phase thermal cracking of a paraffinic feed stock at 800 DEG -1000 DEG F., (c) high conversion steam cracking of gas oils at 1250 DEG -1500 DEG F. or (d) an ethylene growth process in presence of aluminium alkyls. The preferred catalyst for dimerization is an aluminium trialkyl (e.g. triisobutyl) but a dialkyl aluminium chloride is also mentioned; additional catalysts such as nickel, cobalt, palladium and platinum may be used, particularly where it is desired to isomerise internally double bonded olefins in the feed stock. Preferred catalysts for the alkylation step are AlCl3, HF, BF3, AlBr3, polyphosphoric acid, H2SO4 and aluminium chloride hydrocarbon complexes. In the example, dimerization of hexene-1 with Al(n-hexyl)3 gave a C12 olefin containing 82% 2-n-butyl-octene-1, which was used to alkylate benzene in presence of AlCl3 to give the corresponding dodecylbenzene. Specification 770,310 is referred to.ALSO:The invention comprises biodegradable detergent compounds of formula <FORM:0936882/IV(a)/1> wherein Ar is an aromatic hydrocarbon group of which the nucleus is directly linked to the quaternary carbon atom, R is a predominantly straight-chain C3-6 alkyl group, R1 is a predominantly straight-chain C5-8 alkyl group and X is a nuclear-attached sulphonic acid group or water soluble salt thereof. The extent of branching R and R1 is such that on the average less than 1,0 (preferably less than 0,6) equivalent methyl groups, in addition to the two terminal methyl groups, is present. Such compounds are produced by dimerising in presence of an aluminium alkyl catalyst one or more C5-8 predominantly straight-chain alpha-olefins containing on their non-ethylenic carbon atoms on the average less than 0,5 equivalent side-chain methyl groups, alkylating an aromatic hydrocarbon with dimers and sulphonating the alkylated aromatic hydrocarbon. The preferred product is the sodium sulphonate of 2-phenyl-2-n-butyloctane. Specification 770,310 is referred to.
GB27234/61A 1960-09-23 1961-07-27 The preparation of a biodegradable detergent Expired GB936882A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US57885A US3238249A (en) 1960-09-23 1960-09-23 Alkylbenzene sulfonate production via n-olefin dimerization

Publications (1)

Publication Number Publication Date
GB936882A true GB936882A (en) 1963-09-18

Family

ID=22013337

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27234/61A Expired GB936882A (en) 1960-09-23 1961-07-27 The preparation of a biodegradable detergent

Country Status (3)

Country Link
US (1) US3238249A (en)
BE (2) BE616990A (en)
GB (1) GB936882A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999005243A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Detergent compositions containing mixtures of crystallinity-disrupted surfactants
WO1999005242A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Improved alkylbenzenesulfonate surfactants
WO1999005244A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Improved alkyl aryl sulfonate surfactants
US6303556B1 (en) 1999-01-20 2001-10-16 The Procter & Gamble Company Hard surface cleaning compositions comprising modified alkybenzene sulfonates
US6342473B1 (en) 1999-01-20 2002-01-29 The Procter & Gamble Company Hard surface cleaning compositions comprising modified alkylbenzene sulfonates
US6525233B1 (en) 1997-08-08 2003-02-25 The Procter & Gamble Company Process for preparing a modified alkylaryl
US6566319B1 (en) 1997-07-21 2003-05-20 The Procter & Gamble Company Cleaning products comprising improved alkylarylsulfonate surfactants prepared via vinylidene olefins and processes for preparation thereof
US6602840B1 (en) 1997-07-21 2003-08-05 The Procter & Gamble Company Processes for making alkylbenzenesulfonate surfactants and products thereof

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE632800A (en) * 1962-06-01
GB1031691A (en) * 1963-01-31 1966-06-02 Montedison Spa Process for the dimerization of olefins
GB1078572A (en) * 1964-01-17 1967-08-09 British Hydrocarbon Chem Ltd Improvements relating to the production of detergent alkylate
GB1022959A (en) * 1964-02-25 1966-03-16 British Hydrocarbon Chem Ltd Improvements relating to the production of olefines
US3410925A (en) * 1964-05-14 1968-11-12 Continental Oil Co Dimerization of c3 to c18 olefins
US3538175A (en) * 1968-12-11 1970-11-03 Universal Oil Prod Co Hf alkyation process
KR100418820B1 (en) 1998-10-20 2004-02-18 더 프록터 앤드 갬블 캄파니 Laundry detergents comprising modified alkylbenzene sulfonates
WO2000023548A1 (en) 1998-10-20 2000-04-27 The Procter & Gamble Company Laundry detergents comprising modified alkylbenzene sulfonates
US6774099B1 (en) 1999-01-20 2004-08-10 The Procter & Gamble Company Dishwashing detergent compositions containing mixtures or crystallinity-disrupted surfactants
JP2002535442A (en) 1999-01-20 2002-10-22 ザ、プロクター、エンド、ギャンブル、カンパニー Dishwashing composition comprising an alkylbenzene sulfonate surfactant
US7202205B1 (en) 1999-09-01 2007-04-10 Daniel Stedman Connor Processes for making surfactants via adsorptive separation and products thereof
US20040176655A1 (en) * 2003-02-05 2004-09-09 Ayoub Paul Marie Methods of preparing branched alkyl aromatic hydrocarbons
ATE374737T1 (en) * 2003-02-05 2007-10-15 Shell Int Research METHOD FOR PRODUCING BRANCHED ALKYLAROMATIC HYDROCARBONS USING A PROCESS STREAM FROM A DIMERIZATION UNIT
US7335802B2 (en) * 2003-10-15 2008-02-26 Shell Oil Company Methods of preparing branched aliphatic alcohols

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB539281A (en) * 1939-03-04 1941-09-03 Colgate Palmolive Peet Co Improvements in or relating to the preparation of aliphatic substituted aromatic sulphonic acids and salts thereof
US2622113A (en) * 1948-03-31 1952-12-16 Universal Oil Prod Co Production of long chain olefinic hydrocarbons by polymerization
GB742642A (en) * 1950-06-21 1955-12-30 Ziegler Karl Dimerization of mono-olefins
US2612531A (en) * 1950-12-06 1952-09-30 Standard Oil Dev Co Polymerization of olefins and the alkylation of polymer
US2897156A (en) * 1951-09-14 1959-07-28 California Research Corp Manufacture of alkyl benzene sulfonate detergents
US2781410A (en) * 1953-04-04 1957-02-12 Ziegler Polymerization of ethylene in the presence of an aluminum trialkyl catalyst
BE529128A (en) * 1953-05-29
GB775384A (en) * 1953-11-20 1957-05-22 Ziegler Karl Process for the dimerisation of olefins or olefinic mixtures
US2813917A (en) * 1954-07-06 1957-11-19 Continental Oil Co Preparation of alkaryl sulfonates
US2984691A (en) * 1954-09-30 1961-05-16 Standard Oil Co Telomerization process
US2871254A (en) * 1955-10-20 1959-01-27 Shell Dev Olefins from cat-cracked cycle oil
DE1142166B (en) * 1959-05-30 1963-01-10 Schering Ag Process for the production of biodegradable alkylarylsulfonates
US3009972A (en) * 1959-09-25 1961-11-21 Monsanto Chemicals Dimerization of olefins

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999005243A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Detergent compositions containing mixtures of crystallinity-disrupted surfactants
WO1999005242A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Improved alkylbenzenesulfonate surfactants
WO1999005244A1 (en) * 1997-07-21 1999-02-04 The Procter & Gamble Company Improved alkyl aryl sulfonate surfactants
US6274540B1 (en) 1997-07-21 2001-08-14 The Procter & Gamble Company Detergent compositions containing mixtures of crystallinity-disrupted surfactants
AU738353B2 (en) * 1997-07-21 2001-09-13 Procter & Gamble Company, The Improved alkyl aryl sulfonate surfactants
US6566319B1 (en) 1997-07-21 2003-05-20 The Procter & Gamble Company Cleaning products comprising improved alkylarylsulfonate surfactants prepared via vinylidene olefins and processes for preparation thereof
US6593285B1 (en) 1997-07-21 2003-07-15 The Procter & Gamble Company Alkylbenzenesulfonate surfactants
US6602840B1 (en) 1997-07-21 2003-08-05 The Procter & Gamble Company Processes for making alkylbenzenesulfonate surfactants and products thereof
CZ299604B6 (en) * 1997-07-21 2008-09-17 The Procter & Gamble Company Alkylarylsulfonate surfactant system and hand dishwashing composition containing thereof
US6525233B1 (en) 1997-08-08 2003-02-25 The Procter & Gamble Company Process for preparing a modified alkylaryl
US6303556B1 (en) 1999-01-20 2001-10-16 The Procter & Gamble Company Hard surface cleaning compositions comprising modified alkybenzene sulfonates
US6342473B1 (en) 1999-01-20 2002-01-29 The Procter & Gamble Company Hard surface cleaning compositions comprising modified alkylbenzene sulfonates

Also Published As

Publication number Publication date
BE616990A (en)
BE616998A (en)
US3238249A (en) 1966-03-01

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