GB961903A - Aliphatic hydrocarbons and their production - Google Patents

Aliphatic hydrocarbons and their production

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Publication number
GB961903A
GB961903A GB29383/62A GB2938362A GB961903A GB 961903 A GB961903 A GB 961903A GB 29383/62 A GB29383/62 A GB 29383/62A GB 2938362 A GB2938362 A GB 2938362A GB 961903 A GB961903 A GB 961903A
Authority
GB
United Kingdom
Prior art keywords
methyl
formula
mixture
dimerizing
dodecene
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
GB29383/62A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical 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 Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB961903A publication Critical patent/GB961903A/en
Expired legal-status Critical Current

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    • 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
    • C07C2/02—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
    • C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
    • C07C2/22—Metal halides; Complexes thereof with organic compounds
    • 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
    • C07C9/00—Aliphatic saturated hydrocarbons
    • C07C9/22—Aliphatic saturated hydrocarbons with more than fifteen carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2525/00—Catalysts of the Raney type
    • C07C2525/02—Raney nickel
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    • 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
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    • C07C2527/126—Aluminium chloride
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    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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    • C10M2205/024—Propene
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    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/32—Light or X-ray resistance
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/13—Aircraft turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/17—Electric or magnetic purposes for electric contacts
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    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/38—Conveyors or chain belts
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    • C10N2040/42—Flashing oils or marking oils
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    • C10N2040/44—Super vacuum or supercritical use
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

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

Abstract

Long chain paraffins stated to be new compounds having the formula <FORM:0961903/C4-C5/1> in which each R is the same or different branched or straight chain alkyl group having 2-22 carbon atoms are produced by dimerizing an alpha-olefin or mixture of alpha-olefins having the formula R-CH=CH2 in the presence of a Ziegler catalyst of the formula M(R1)x or a complex thereof in which M is aluminium, gallium, indium or beryllium of valency X and each R1 is hydrogen or an alkyl or aromatic group containing up to 22 carbon atoms, dimerizing the dimer thus formed in the presence of a Friedel-Crafts or acid catalyst and catalytically hydrogenating the product, e.g. in the presence of Raney nickel, to obtain a saturated hydrocarbon of the above formula. The products have high thermal stability and low pour point and are useful as fuels, lubricants, grease bases, hydraulic fluids and coolants. The examples describe the production of (1) 11,13-di-n-octyl-13-methyl tricosane from decene-1; (2) 9,11-di-n-hexyl-11-methyl nonadecane from octene-1; (3) 7,9-di-n-butyl-9-methyl pentadecane from hexene-1; (4) 13,15-di-n-decyl-15-methyl heptacosane from dodecene-1 and (5) a C40-C48 mixture from a mixture of decene-1 and dodecene-1.
GB29383/62A 1961-08-03 1962-07-31 Aliphatic hydrocarbons and their production Expired GB961903A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2409299A1 (en) * 1977-11-22 1979-06-15 Uniroyal Inc HEAT TRANSFER FLUID SYSTEMS
EP0004425A1 (en) * 1978-03-09 1979-10-03 Uniroyal, Inc. A method of insulating and transporting heat from the components of a transformer by means of a fluid and transformer impregnated with a fluid
WO1998020053A1 (en) * 1996-11-04 1998-05-14 Basf Aktiengesellschaft Polyolefins and their functionalized derivatives
WO2006120925A1 (en) 2005-05-12 2006-11-16 Idemitsu Kosan Co., Ltd. Process for producing saturated aliphatic hydrocarbon compound, and lubricant composition
WO2021015172A1 (en) 2019-07-25 2021-01-28 出光興産株式会社 Saturated aliphatic hydrocarbon compound composition, lubricant composition, and method for producing saturated aliphatic hydrocarbon compound composition

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* Cited by examiner, † Cited by third party
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US3876722A (en) * 1968-09-16 1975-04-08 Exxon Research Engineering Co Copolymer of c' 3 'to c' 8 'alpha-olefin and c' 22 'to c' 40 'alpha-olefin
US3666827A (en) * 1969-11-14 1972-05-30 Monsanto Co Quaternary substituted hydrocarbons
US3742082A (en) * 1971-11-18 1973-06-26 Mobil Oil Corp Dimerization of olefins with boron trifluoride
US3957664A (en) * 1972-07-24 1976-05-18 Gulf Research & Development Company Lubricant and hydraulic fluid compositions
US3907922A (en) * 1972-07-24 1975-09-23 Gulf Research Development Co Process for dimerizing vinylidene compounds
US3876720A (en) * 1972-07-24 1975-04-08 Gulf Research Development Co Internal olefin
JPS5715566B2 (en) * 1973-07-06 1982-03-31
US3912617A (en) * 1974-02-14 1975-10-14 Sun Oil Co Pennsylvania Blended refrigeration oil composition
JPS53142541A (en) * 1977-05-19 1978-12-12 Lion Corp Cosmetic base
US4973788A (en) * 1989-05-05 1990-11-27 Ethyl Corporation Vinylidene dimer process
US5284988A (en) * 1991-10-07 1994-02-08 Ethyl Corporation Preparation of synthetic oils from vinylidene olefins and alpha-olefins
US5498815A (en) * 1991-12-13 1996-03-12 Albemarle Corporation Preparation of synthetic oils from vinylidene olefins and alpha-olefins
US5728907A (en) * 1995-10-27 1998-03-17 Pennzoil Products Company Tetraalkylmethanes as synthetic lubricants
US6824671B2 (en) * 2001-05-17 2004-11-30 Exxonmobil Chemical Patents Inc. Low noack volatility poly α-olefins
DE10145619A1 (en) * 2001-09-15 2003-04-10 Basf Ag Process for the trimerization of alpha olefins
US6869917B2 (en) * 2002-08-16 2005-03-22 Exxonmobil Chemical Patents Inc. Functional fluid lubricant using low Noack volatility base stock fluids
GB0320684D0 (en) * 2003-09-03 2003-10-01 Bp Chem Int Ltd Process
US7700684B2 (en) * 2004-12-09 2010-04-20 Afton Chemical Corporation Graft functionalized olefin polymer dispersant and uses thereof
EP2256181B1 (en) * 2005-01-07 2016-06-01 Nippon Oil Corporation Lubricant base oil and lubricant composition for an internal combustion engine and lubricant composition for a driving force transmitting device
WO2007011462A1 (en) 2005-07-19 2007-01-25 Exxonmobil Chemical Patents Inc. Lubricants from mixed alpha-olefin feeds
JP5016809B2 (en) * 2005-11-09 2012-09-05 出光興産株式会社 Method for producing vinylidene compound oligomer
US8865959B2 (en) * 2008-03-18 2014-10-21 Exxonmobil Chemical Patents Inc. Process for synthetic lubricant production

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2409299A1 (en) * 1977-11-22 1979-06-15 Uniroyal Inc HEAT TRANSFER FLUID SYSTEMS
EP0004425A1 (en) * 1978-03-09 1979-10-03 Uniroyal, Inc. A method of insulating and transporting heat from the components of a transformer by means of a fluid and transformer impregnated with a fluid
WO1998020053A1 (en) * 1996-11-04 1998-05-14 Basf Aktiengesellschaft Polyolefins and their functionalized derivatives
US6133209A (en) * 1996-11-04 2000-10-17 Basf Aktiengesellschaft Polyolefins and their functionalized derivatives
AU747797B2 (en) * 1996-11-04 2002-05-23 Basf Aktiengesellschaft Polyolefins and their functionalized derivatives
WO2006120925A1 (en) 2005-05-12 2006-11-16 Idemitsu Kosan Co., Ltd. Process for producing saturated aliphatic hydrocarbon compound, and lubricant composition
US8373011B2 (en) 2005-05-12 2013-02-12 Idemitsu Kosan Co., Ltd. Process for producing saturated aliphatic hydrocarbon compound, and lubricant composition
WO2021015172A1 (en) 2019-07-25 2021-01-28 出光興産株式会社 Saturated aliphatic hydrocarbon compound composition, lubricant composition, and method for producing saturated aliphatic hydrocarbon compound composition

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