Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/02—Well-defined hydrocarbons
  • C10M105/04—Well-defined hydrocarbons aliphatic
• • 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
  • C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
  • C07C2/34—Metal-hydrocarbon complexes
• • 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
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
  • C08F10/14—Monomers containing five or more carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
  • C08F110/14—Monomers containing five or more carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
  • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
• • 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
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
  • C07C2531/22—Organic complexes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F4/00—Polymerisation catalysts
  • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
  • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
  • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
  • C08F4/62—Refractory metals or compounds thereof
  • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
  • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
  • C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F4/00—Polymerisation catalysts
  • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
  • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
  • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
  • C08F4/62—Refractory metals or compounds thereof
  • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
  • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
  • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F4/00—Polymerisation catalysts
  • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
  • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
  • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
  • C08F4/62—Refractory metals or compounds thereof
  • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
  • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
  • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
  • C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
  • C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/02—Well-defined aliphatic compounds
  • C10M2203/0206—Well-defined aliphatic compounds used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/022—Ethene
  • C10M2205/0225—Ethene used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • 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
  • C10M2205/0285—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 used as base material
• • 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
  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
  • C10N2020/02—Viscosity; Viscosity index
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/54—Fuel economy
• • 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
  • C10N2040/25—Internal-combustion engines

Definitions

• the invention relates to a low viscosity oil comprising more than 50% by weight of 9-methyl-1-octyl-henicosane and a lubricating composition comprising this base oil and optionally another base oil or an additive.
• This oil according to the invention has a kinematic viscosity at 100 ° C., measured according to the ASTM D445 standard, ranging from 3 to 4 mm 2 .s -1 .
• the invention also relates to such a low viscosity oil prepared according to a particular method using a metallocene catalyst and the use of this oil as a high performance lubricant for lubrication in the fields of engines, gears, braking , hydraulic fluids, refrigerants, greases.
• PAO polyalphaolefins
• PAOs are synthesized from different olefinic monomers, in particular from C 6 -C 14 monomers, by acid catalysis or in the presence of a metallocene catalyst.
• Methods for the preparation of PAO by metallocene catalysis are generally known, which generally result in products of high viscosity whose kinematic viscosity at 100 ° C., measured according to ASTM D445, ranges from 40 to 150 mm 2 .s -1 ( grades 40 to 150.
• the need for high-performance lubricants is increasing, in particular because of conditions of use, the severity of which is increasing, for example due to very high temperatures or mechanical stresses.
• Drainage spacing and reduced size of lubrication systems also increase the need for high performance lubricants.
• Energy efficiency and in particular the improvement of the Fuel Eco (FE) of lubricants or the reduction of the fuel consumption of engines, in particular of vehicle engines, are increasingly important objectives and lead to the increasing use of high performance lubricants.
• FE Fuel Eco
• High performance lubricants must therefore have improved properties, in particular as regards kinematic viscosity, viscosity index, volatility, dynamic viscosity or cold pour point.
• Thermal stability and oxidation resistance are also properties to be improved for high performance lubricants.
• the processes for preparing PAO should also make it possible to recycle all or part of the secondary products resulting from the oligomerization reactions.
• PAO preparation processes should also be able to control the molecular weight as well as the polydispersity index and the distribution of PAOs formed.
• the improvement of the characterization techniques of the different products formed during the synthesis of PAO is also to be sought, in particular during the qualitative or quantitative analysis of the products formed.
• WO-2013/055480 discloses the preparation of PAOs useful as vehicle engine lubricants. This document describes a lubricating composition comprising such an oil associated with another base oil and a viscosity index improving additive. However, this patent application does not disclose 9-methyl-1-octyl-henicosane, nor its particular properties.
• EP-1,950,278 discloses a motor lubricant composition comprising in particular a saturated oligomer of olefins obtained by metallocene catalysis.
• this patent application does not disclose 9-methyl-1-octyl-henicosane, nor its particular properties.
• WO-2007/01973 describes the catalytic preparation of PAO.
• This patent application describes the use of non-bridged metallocene catalysts. This document does not describe the preparation of 9-methyl-1-octyl-henicosane, nor its particular properties.
• WO-2007/01 1459 discloses PAOs obtained from the polymerization of C 5 -C 2 4-olefins. This patent application does not disclose 9-methyl-1-octyl-henicosane or its particular properties.
• WO-02/14384 discloses a process for the polymerization of olefins by metallocene catalysis. The process described uses only fluoro-cyclopentadienyl catalysts. This document does not describe the preparation of 9-methyl-1-octyl-henicosane.
• WO-89/12662 discloses a liquid lubricant composition based on hydrocarbons C 30 - C 300 where the ratio of methyl / methylene groups is less than 0.19. This document does not disclose a proportion greater than 50% by weight of 9-methyl-1-octylheneicosane in an oil.
• EP-283922 relates to a mixture comprising a polysiloxane and a hydrogenated PAO.
• the disclosed Synfluid 4 cS product does not include more than 50% by weight of 9-methyl-1-octylheneicosane in an oil. There is therefore a need for high performance lubricants to provide a solution to all or part of the problems of the lubricants of the state of the art.
• the invention provides an oil of kinematic viscosity at 100 ° C, measured according to ASTM D445, ranging from 3 to 4 mm 2 .s -1 , comprising more than 50% by weight of 1-decene trimer of formula I)
• the oil according to the invention has a particularly advantageous kinematic viscosity ranging from 3 to 4 mm 2 ⁇ s -1, more advantageously the kinematic viscosity of the oil according to the invention ranges from 3.2 to 3.8. mm 2 .s “1 .
• the kinematic viscosity of the oil according to the invention is 3.4 mm 2 . s “1 , 3.5 mm 2. s " 1 or 3.6 mm 2 . s "1 .
• the oil according to the invention has a viscosity index greater than 120 or between 120 and 140 or between 125 and 135.
• the viscosity number of the oil according to the invention is greater than or equal to 130.
• the viscosity number is calculated according to the ASTM D2270 standard.
• the oil according to the invention has a volatility measured according to ASTM D6375 less than 10.8% by weight.
• the volatility of the oil according to the invention is less than 10.5% by weight.
• the oil according to the invention has a dynamic viscosity (CCS) at -35 ° C., measured according to ASTM D5293, of less than 900 mPa.s.
• the dynamic viscosity of the oil according to the invention is less than 800 mPa.s.
• the dynamic viscosity of the oil according to the invention is measured on a rotating dynamic viscometer (CCS cold cranking simulator).
• the oil according to the invention has an average molecular weight ranging from 300 to 1000 g / mol, preferably from 350 to 450 g / mol. In general, according to the invention, the average molecular weight is calculated according to the ASTM D2502 standard.
• the oil according to the invention has a pour point less than or equal to -50 ° C, preferably less than or equal to -55 or -57 ° C.
• the pour point is measured according to the EN ISO 3016 standard.
• the invention provides a combination oil.
• the invention provides an oil combining these properties (a) and (b); (a) and (c); (a) and (d); (b) and (c); (b) and (d); (c) and (d); (a), (b) and (c); (a), (b) and (d); (a), (c) and (d); (b), (c) and (d).
• the invention provides a combination oil
• the invention provides an oil combining these properties (a) and (b); (a) and (c); (a) and (d); (b) and (c); (b) and (d); (c) and (d); (a), (b) and (c); (a), (b) and (d); (a), (c) and (d); (b), (c) and (d).
• the oil according to the invention comprises at least 65% by weight of 1-decene trimer of formula (I) or at least 70% by weight of 1-decene trimer of formula (I). More advantageously, the oil according to the invention comprises at least 80% by weight of 1-decene trimer of formula (I) or at least 90% by weight of 1-decene trimer of formula (I).
• the oil according to the invention comprises from 50 to 99% by weight of 1-decene trimer of formula (I). More preferably, the oil according to the invention comprises from 60 to 90% by weight of 1-decene trimer of formula (I). Even more preferably, the oil according to the invention comprises from 70 to 90% by weight of 1-decene trimer of formula (I).
• the oil according to the invention comprises from 60 to 95% by weight, from 60 to 80% by weight, from 70 to 95% by weight, from 70 to 80% by weight, from 75 to 95% by weight by weight or from 75 to 80% by weight of 1-decene trimer of formula (I).
• the oil according to the invention may comprise other oligomers derived from the oligomerization of 1-decene.
• the oil according to the invention may comprise at least one other saturated oligomer of 1-decene.
• this other saturated oligomer of 1-decene may be chosen from the other saturated trimers of 1-decene. It may also be selected from a broader group of saturated oligomers including 1-decene dimers, other 1-decene trimers, 1-decene tetramers, 1-decene pentamers.
• the oil according to the invention may also comprise at least one other saturated oligomer of 1-decene selected from 9-methyl-nonadecane and 9-methyl-1, 13-dioctyl-tricosane.
• the oil according to the invention may also comprise other oligomers of 1-decene which are larger in size.
• the oil according to the invention comprises
• the oil according to the invention comprises
• ⁇ from 0.1 to 20% by weight of at least one saturated tetramer of 1-decene, for example 9-methyl-1 1, 13-dioctyl-tricosane;
• ⁇ from 0.1 to 1, 5% by weight of at least one saturated pentamer of 1-decene.
• the oil according to the invention has the essential characteristic of comprising more than 50% by weight of 9-methyl-1-octyl-henicosane.
• the oil according to the invention comprising more than 50% by weight of 9-methyl-1-octyl-henicosane is prepared according to a process comprising
• trimers fraction comprising more than 50% by weight trimer of 1-decene of formula (I)
• the oligomerization of 1-decene is carried out in the presence of a metallocene catalyst which is a racemic compound of formula (II)
• M represents a transition metal selected from titanium, zirconium, hafnium, and vanadium or represents zirconium;
• Q 1 and Q 2 substituted or unsubstituted, independently represent a tetrahydroindenyl cyclic group or Q 1 and Q 2 independently represent a tetrahydroindenyl cyclic group and are bonded to form a polycyclic structure;
• o L represents a Ci-C 20 alkyl group divalent bridging Q 1 and Q 2 or L represents a group selected from methylene (-CH 2 -), ethylene (- CH 2 -CH 2 -), methylmethylene (-CH (CH 3 ) -), 1-methyl-ethylene (-CH (CH 3 ) -CH 2 -), n-propylene (-CH 2 -CH 2 -CH 2 -), 2-methylpropylene (-CH 2 -CH (CH) 3 ) -CH 2 -), 3-methylpropylene (-CH 2 -CH 2 -CH (CH 3 ) -), n-butylene (-CH 2 -CH 2 -CH 2 -), 2-methylbutylene ( -CH 2 -CH (CH 3 ) -CH 2 -), 2-methylbutylene ( -CH 2 -CH (CH 3 ) -CH 2 -), 2-methylbutylene ( -CH 2 -CH (CH 3 ) -CH 2 -
• R 1 and R 2 substituted or unsubstituted, independently represent an atom or group selected from hydrogen, halogen (such as Cl and I), alkyl (such as Me, Et, nPr, iPr), alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, silylalkyl, silylalkenyls, silylalkynyls, germylalkyl, germylalkenyl, germylalkylalkyl, germylalkenyl, germylalkylalky
• the metallocene catalyst is a racemic compound of formula (II) in which M represents zirconium;
• Q 1 and Q 2 substituted or unsubstituted, independently represent a tetrahydroindenyl cyclic group
• L represents a group chosen from methylene (-CH 2 -), ethylene (-CH 2 -CH 2 -), methylmethylene (-CH (CH 3 ) -), 1-methyl-ethylene (-CH (CH 3 ) - CH 2 -), n-propylene (-CH 2 -CH 2 -CH 2 -), 2-methylpropylene (- CH 2 -CH (CH 3) -CH 2 -), 3-methylpropylene (-CH 2 -CH 2 -CH (CH 3 ) -), n-butylene (-CH 2 -CH 2 -CH 2 -CH 2 -), 2-methylbutylene (-CH 2 -CH (CH 3 ) -CH 2 -CH 2 -), 4-methylbutylene (-CH 2 -CH 2 -CH 2 -CH (CH 3 ) -), pentylene and its isomers, hexylene and isomers thereof, heptylene and isomers thereof, octylene and iso
• the metallocene catalyst is selected from rac-ethylene bis (tetrahydroindenyl) zirconium dimethyl and rac-ethylene bis (tetrahydroindenyl) zirconium dichloride, in particular rac-ethylene bis (tetrahydroindenyl) zirconium dimethyl.
• the catalyst is used in an activated form for the oligomerization of 1-decene.
• the process according to the invention uses an activator compound during the oligomerization of 1-decene.
• the activator compound is chosen from an alumoxane, an ionic activator and their mixtures.
• the alumoxane is an oligomeric compound comprising residues of formula -Al (R) -0- wherein R independently represents a C 20 alkyl group, cyclic or linear.
• R independently represents a C 20 alkyl group, cyclic or linear.
• the alumoxane is chosen from methylalumoxane, modified methylalumoxane, ethylalumoxane, isobutylalumoxane and mixtures thereof.
• the alumoxane is used in an alumoxane / catalyst molar ratio ranging from 1 to 10,000, preferably from 10 to 3,000 and more preferably from 100 to 1,500.
• the activator compound is an ionic activator.
• the ionic activator may be chosen from dimethylanilinium tetrakis- (perfluorophenyl) borate (DMAB), triphenylcarbonium tetrakis- (perfluorophenyl) borate, dimethylanilinium tetrakis- (perfluorophenyl) aluminate and mixtures thereof. More preferably, the ionic activator is dimethylanilinium tetrakis- (perfluorophenyl) borate (DMAB).
• the ionic activator is used in an ionic activator / catalyst molar ratio ranging from 0.5 to 4, preferably from 0.8 to 1, 2.
• the process according to the invention uses an activator compound. It may also be advantageous to use a coactivator compound, in particular when using an ionic activator.
• the coactivator compound is a trialkylaluminium derivative. More preferably, the co-activator compound is selected from tri-ethyl aluminum (TEAL), tri-iso-butyl aluminum (TIBAL), tri-methyl aluminum (TMA), tri-n-octyl aluminum and methyl-methyl ethyl aluminum (MMEAL).
• TEAL tri-ethyl aluminum
• TIBAL tri-iso-butyl aluminum
• TMA tri-methyl aluminum
• MMEAL methyl-methyl ethyl aluminum
• tri-iso-butyl aluminum (TIBAL) is used in the form of a dispersion that can range from 10 to 60% by weight.
• the coactivator compound is used in a co-activator / catalyst compound molar ratio ranging from 10 to 1,000, preferably from 20 to 200.
• the metallocene catalyst and the activator compound are brought into contact at a pressure of 1 bar and at a temperature of 20 ° C.
• the oligomerization of 1-decene is carried out in a time ranging from 2 to 300 min.
• the duration of the oligomerization is from 5 to 180 min, in particular from 30 to 140 min.
• the oligomerization of 1-decene is carried out in the presence of hydrogen (H 2 ) at a partial pressure ranging from 0.1 to 20 bar.
• the hydrogen partial pressure (H 2 ) ranges from 1 to 6 bar.
• the oligomerization is carried out in a mass ratio hydrogen / 1-decene greater than 100 ppm or less than 600 ppm. Preferably, this ratio is between 100 and 600 ppm.
• the oligomerization of 1-decene is carried out at a temperature ranging from 50 to 200 ° C, preferably from 70 to 160 ° C. More Preferably, the temperature during the oligomerization of 1-decene ranges from 80 to 150 ° C and even more preferably from 90 to 140 ° C or from 100 to 130 ° C.
• the oligomerization of 1-decene can be carried out in 1-decene, which then serves as a support for the reaction.
• the reaction is then advantageously carried out in the absence of a solvent.
• the oligomerization of 1-decene can also be carried out in a solvent.
• the solvent may be chosen from a linear or branched hydrocarbon, a cyclic or non-cyclic hydrocarbon, an alkylated aromatic compound and mixtures thereof.
• a solvent selected from butanes, pentanes, hexanes, heptanes, octanes, cyclopentane, cyclohexane, methylcyclopentane, methylcyclohexane, methylcycloheptane, toluene, xylene and mixtures thereof.
• the process according to the invention implements the catalytic hydrogenation of the oligomerization products.
• the catalytic hydrogenation of the oligomerization products is carried out in the presence of hydrogen (H 2 ) and a hydrogenation catalyst.
• the hydrogenation catalyst is chosen from a palladium derivative, a supported palladium derivative, a palladium derivative supported on alumina (for example on gamma-alumina), a nickel derivative, a supported nickel derivative, a nickel derivative supported on kieselguhr, a platinum derivative, a supported platinum derivative, a cobalt-molybdenum derivative, a supported cobalt-molybdenum derivative.
• the hydrogenation catalyst comprises palladium.
• a particularly preferred hydrogenation catalyst comprises palladium supported on alumina (for example on gamma-alumina).
• the hydrogen pressure (H 2 ) during the catalytic hydrogenation of the oligomerization products ranges from 5 to 50 bar, more preferably from 10 to 40 bar, in particular from 15 to 25 bar.
• the process according to the invention comprises separation by distillation at reduced pressure of the trimeric fraction comprising more than 50% by weight of 1-decene trimer of formula (I).
• the separation by distillation is carried out under reduced pressure.
• the separation by distillation is carried out according to ASTM D2892 or ASTM D5236.
• the separation is carried out in two stages, by distillation according to ASTM D2892 and then by distillation according to ASTM D5236.
• the initial boiling point (IBP) is less than 370 ° C., preferably less than 375 ° C.
• the partial pressure is advantageously less than 0.67 mBar (0.5 mmHg).
• the initial boiling point (IBP or initial boiling point) is between 360 and 485 ° C, preferably between 370 and 480 ° C or between 370 and 480 ° C. 470 ° C. More preferably, the initial boiling point is between 375 and 465 ° C when carrying out the distillation separation according to ASTM D5236.
• the partial pressure is advantageously less than 0.67 mBar (0.5 mmHg).
• the separation by distillation according to ASTM D5236 makes it possible to separate the fraction of trimers comprising more than 50% by weight of 1-decene trimer of formula (I).
• This fraction of trimers comprises more than 50% by weight of 1-decene trimer of formula (I).
• the method according to the invention may advantageously comprise other steps.
• the process according to the invention can also combine all or part of the following steps: the prior preparation of 1-decene by catalytic oligomerization of ethylene; ⁇ deactivating the catalyst after oligomerization of 1-decene or after the catalytic hydrogenation of the oligomerization product;
• trimer fraction comprising more than 50% by weight trimer of 1-decene of formula (I) in the presence of hydrogen
• the prior preparation of 1-decene by catalytic oligomerization of ethylene is known as such. It can be particularly advantageous in combination with the other steps of the process according to the invention.
• This prior preparation of 1-decene by catalytic oligomerization of ethylene makes it possible in particular to use more abundant sources of starting substrate.
• the process according to the invention may comprise the deactivation of the catalyst.
• the deactivation of the oligomerization catalyst can be carried out after the oligomerization of 1-decene or after the catalytic hydrogenation of the oligomerization products.
• the deactivation of the oligomerization catalyst is carried out after the oligomerization of 1-decene and before the catalytic hydrogenation of the oligomerization products.
• the deactivation of the catalyst is carried out by the action of air or water or by means of at least one alcohol or a solution of deactivating agent.
• the deactivation of the catalyst is carried out using at least one alcohol, for example isopropanol.
• the process according to the invention may also comprise the recycling of the dimer fraction of 1-decene which is separated by distillation at reduced pressure and then the oligomerization of this fraction of 1-decene dimers. decene recycled with 1-decene.
• this recycled 1-decene dimer fraction comprises 9-methyl-nonadecane.
• the oligomerization of this dimeric fraction of the recycled 1-decene can then be carried out in the presence of hydrogen (H 2 ), a metallocene catalyst and an activator compound or in the presence of hydrogen (H 2 ), a metallocene catalyst, an activator compound and a coactivator compound.
• the oligomerization of this dimeric fraction of the recycled 1-decene can be carried out in the oligomerization reactor of 1-decene or in one or more separate reactors. In a preferred manner, it is carried out in the oligomerization reactor of 1-decene and under the same conditions as this oligomerization of 1-decene.
• the recycling and oligomerization of this dimer fraction of 1-decene recycled with 1-decene improves the overall yield of the preparation process according to the invention and thus produce a larger amount of oil according to the invention comprising more than 50% by weight of 9-methyl-1 1-octyl-henicosane.
• the process according to the invention may comprise a final step of hydrogenation of the trimeric fraction comprising more than 50% by weight of 1-decene trimer of formula (I). This final hydrogenation is carried out in the presence of hydrogen (H 2 ) and a hydrogenation catalyst.
• the hydrogenation catalyst is chosen from a palladium derivative, a supported palladium derivative, a palladium derivative supported on alumina (for example on gamma-alumina), a nickel derivative, a supported nickel derivative, a nickel derivative supported on kieselguhr, a platinum derivative, a supported platinum derivative, a cobalt-molybdenum derivative, a supported cobalt-molybdenum derivative. More preferably, the hydrogenation catalyst comprises palladium. A particularly preferred catalyst comprises palladium supported on alumina (for example on gamma-alumina).
• the hydrogenation catalyst is advantageously identical to the hydrogenation catalyst used during the hydrogenation according to the oligomerization of 1-decene.
• the hydrogen pressure (H 2 ) ranges from 5 to 50 bar or from 10 to 40 bar, preferably from 15 to 25 bar.
• the duration of the hydrogenation is between 2 and 600 min, preferably between 30 and 300 min.
• the temperature ranges from 50 to 200 ° C or from 60 to 150 ° C.
• the temperature is 70 to 140 ° C or 80 to 120 ° C.
• the oil according to the invention is prepared according to a process for which the oligomerization of 1-decene is carried out in a time ranging from 2 to 300 min or from 5 to 180 min or from 30 to 140 min; or
• the oligomerization is conducted in the presence of hydrogen (H 2) in a weight ratio hydrogen / 1-decene greater than 100 ppm or less than 600 ppm or between
• ⁇ the oligomerization of 1-decene is conducted at a temperature ranging from 50 to 200 ° C or from 70 to 160 ° C or from 80 to 150 ° C or from 90 to 140 ° C or 100 to 130 ° C; or
• the metallocene catalyst is a racemic compound of formula (II)
• M represents a transition metal selected from titanium, zirconium, hafnium, and vanadium or represents zirconium;
• Q 1 and Q 2 substituted or unsubstituted, independently represent a tetrahydroindenyl cyclic group or Q 1 and Q 2 independently represent a tetrahydroindenyl cyclic group and are bonded to form a polycyclic structure;
• L represents a divalent BrC 20 -alkyl bridging group Q 1 and
• Q 2 or L represents a group selected from methylene (-CH 2 -), ethylene (-CH 2 -CH 2 -), methylmethylene (-CH (CH 3 ) -), 1-methyl-ethylene (-CH (CH 3 ) -CH 2 -), n-propylene (-CH 2 -CH 2 -CH 2 -), 2-methylpropylene (-CH 2 -CH (CH 3) -CH 2 -), 3-methylpropylene (-CH 2 - CH 2 -CH (CH 3 ) -), n-butylene (-CH 2 -CH 2 -CH 2 -CH 2 -), 2-methylbutylene
• R 1 and R 2 substituted or unsubstituted, independently represent an atom or a group chosen from hydrogen, halogens (such as Cl and I), alkyl (such as Me, Et, nPr, iPr), alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, silylalkyl, silylalkenyls, silylalkynyls
• the metallocene catalyst is selected from rac-ethylene bis (tetrahydroindenyl) zirconium dimethyl and rac-ethylene bis (tetrahydroindenyl) zirconium dichloride; or the oligomerization of 1-decene is carried out in a solvent selected from a linear or branched hydrocarbon, a cyclic or non-cyclic hydrocarbon, an alkylated aromatic compound and mixtures thereof or in a solvent selected from butanes, pentanes, hexanes, heptanes, octanes, cyclopentane, cyclohexane, methylcyclopentane, methylcyclohexane, methylcycloheptane, toluene, xylene and mixtures thereof; or
• the activator compound is chosen from an ionic activator and an oligomeric compound comprising residues of formula -AI (R) -O- in which R independently represents a linear or cyclic CC 2 o alkyl group; or the activator compound is selected from methylalumoxane, modified methylalumoxane, ethylalumoxane, isobutylalumoxane and mixtures thereof; or the activator compound is selected from dimethylanilinium tetrakis (perfluorophenyl) borate (DMAB), triphenylcarbonium tetrakis (perfluorophenyl) borate, dimethylanilinium tetrakis (perfluorophenyl) aluminate and mixtures thereof; or
• the co-activator compound is a trialkylaluminium derivative or a compound chosen from tri-ethyl aluminum (TEAL), tri-iso-butyl aluminum (TIBAL), tri-methyl aluminum (TMA), tri-n-octyl aluminum and methyl-methyl aluminum-ethyl (MMEAL); or
• the deactivation of the catalyst is carried out by the action of air or water or by means of at least one alcohol or a solution of deactivating agent; or the hydrogen pressure (H 2 ) during the catalytic hydrogenation of the oligomerization products is 5 to 50 bar or 10 to 40 bar or 15 to 25 bar; or the hydrogenation catalyst is selected from a palladium derivative, a supported palladium derivative, a palladium derivative supported on alumina (for example on gamma-alumina), a nickel derivative, a supported nickel derivative, a derivative of nickel supported on kieselguhr, a platinum derivative, a supported platinum derivative, a cobalt-molybdenum derivative, a supported cobalt-molybdenum derivative; or
• ⁇ the pressure of hydrogen (H 2) in the final hydrogenation of the major fraction by weight of trimer 1-decene of formula (I) is from 5 to 50 bar or 10 to 40 bar or 15 to 25 bar; or
• ⁇ the length of the hydrogenation in the final hydrogenation is between 2 and 600 minutes or between 30 and 300 min; or
• the final hydrogenation is carried out at a temperature ranging from 50 to 200 ° C or from 60 to 150 ° C or from 70 to 140 ° C or from 80 to 120 ° C; or
• the hydrogenation catalyst during the final hydrogenation of the trimeric fraction comprising more than 50% by weight of 1-decene trimer of formula (I), is chosen from a palladium derivative, a supported palladium derivative; , a palladium derivative supported on alumina (for example on gamma-alumina), a nickel derivative, a supported nickel derivative, a nickel derivative supported on kieselguhr, a platinum derivative, a supported platinum derivative, a cobalt derivative molybdenum, a supported cobalt-molybdenum derivative.
• the oil according to the invention is prepared according to a process combining all of these characteristics.
• the oil according to the invention is prepared according to a process for which
• the oligomerization of 1-decene is made of a weight ratio hydrogen / 1 - decene between 100 and 600 ppm;
• ⁇ the oligomerization of 1-decene is conducted at a temperature ranging from 100 to 130 ° C;
• the metallocene catalyst is selected from rac-ethylene bis (tetrahydroindenyl) zirconium dimethyl and rac-ethylene bis (tetrahydroindenyl) zirconium dichloride;
• the oligomerization of 1-decene is carried out in a solvent chosen from butanes, pentanes, hexanes, heptanes, octanes, cyclopentane, cyclohexane, methylcyclopentane, methylcyclohexane, methylcycloheptane, toluene, xylene and their mixtures;
• the activator compound is selected from an ionic activator selected from dimethylanilinium tetrakis (perfluorophenyl) borate, triphenylcarbonium tetrakis (perfluorophenyl) borate, dimethylanilinium tetrakis (perfluorophenyl) aluminate and mixtures thereof;
• the co-activator is a compound selected from tri-ethyl aluminum (TEAL), tri-iso-butyl aluminum (TIBAL), tri-methyl aluminum (TMA), tri-n-octyl aluminum and methyl-methyl-ethyl aluminum (MMEAL);
• ⁇ the catalyst deactivation is carried out by means of at least one alcohol
• ⁇ the pressure of hydrogen (H 2) upon catalytic hydrogenation of the oligomerization product is from 15 to 25 bar;
• the hydrogenation catalyst is a derivative of palladium supported on alumina (eg gamma-alumina);
• ⁇ the pressure of hydrogen (H 2) in the final hydrogenation of the major fraction by weight of trimer 1-decene of formula (I) is from 15 to 25 bar;
• ⁇ the length of the hydrogenation in the final hydrogenation is between 30 and 300 min;
• the final hydrogenation is carried out at a temperature ranging from 80 to 120 ° C;
• the hydrogenation catalyst, in the final hydrogenation of the fraction of trimers comprising more than 50% by weight trimer of 1-decene of formula (I) is a derivative of palladium supported on alumina (eg gamma - alumina).
• the oil according to the invention is prepared according to a process also comprising
• a final step of hydrogenation of the trimer fraction comprising more than 50% by weight trimer of 1-decene of formula (I) in the presence of hydrogen (H 2) and a catalyst chosen from a catalyst hydrogenation and a hydrogenation catalyst comprising palladium supported on alumina (for example on gamma-alumina).
• the invention also relates to the use as base oil or lubricating base oil of an oil according to the invention. This use therefore relates to a low viscosity oil comprising more than 50% by weight of 9-methyl-1-octyl-henicosane.
• the invention also relates to the use of an oil according to the invention for improving the Fuel Eco (FE) of a lubricant. It also relates to its use to reduce the fuel consumption of an engine or to reduce the fuel consumption of a vehicle engine.
• FE Fuel Eco
• the invention also relates to a lubricant composition
• a lubricant composition comprising an oil according to the invention.
• This lubricating composition therefore comprises a low viscosity oil comprising more than 50% by weight of 9-methyl-1-octyl-henicosane.
• the composition according to the invention comprises at least 10% by weight or at least 20% by weight of an oil according to the invention. Also advantageously, the composition according to the invention comprises at least 30, 40, 50 or 60% by weight of an oil according to the invention.
• composition according to the invention comprises an oil according to the invention and at least one other base oil. It may also comprise an oil according to the invention and at least one additive or an oil according to the invention, at least one other base oil and at least one additive.
• the lubricant composition according to the invention may comprise an oil according to the invention as defined by its advantageous, particular or preferred characteristics as well as by its preparation process.
• the composition according to the invention may comprise an oil chosen from a Group III oil, a Group IV oil.
• the lubricant composition according to the invention is particularly advantageous for use as a high performance lubricant for lubrication in the fields of motors, gears, braking, hydraulic fluids, refrigerants, greases.
• the invention also relates to the use of a lubricant composition according to the invention for improving the Fuel Eco (FE) of a lubricant. It also concerns its use to reduce the fuel consumption of an engine or to reduce the fuel consumption of a vehicle engine.
• FE Fuel Eco
• An autoclave reactor equipped with an agitator, a temperature control system and inlets for introducing nitrogen, hydrogen and 1-decene was used.
• 1-Decene (a product of TCI or the company Acros) is used at a purity higher than 94%. It is purified on 3 A and 13 X molecular sieves (Sigma-Aldrich company). Before use, the molecular sieves used are pre-dried at 200 ° C. for 16 hours. The products are characterized by 1 H NMR and two-dimensional gas phase chromatography (GCxGC).
• the samples of PAO were diluted in the deuterated chloroform and the NMR spectra were carried out with 300 K on Bruker spectrometers 400 MHz: 1 H, 13 C, HMQC (heteronuclear multiple quantum coherence) and HMBC (multiple heteronuclear bond coherence).
• the two-dimensional chromatography is implemented in continuous mode by means of two apolar and polar columns.
• the entire effluent from the first column is separated in the second dimension.
• the separation of the compounds is governed by the volatility on the first column and by specific interactions ( ⁇ - ⁇ type, dipolar interactions, etc.) on the second dimension.
• the samples are usually diluted twice in heptane.
• the chromatographic conditions were optimized to elute the PAOs prepared according to the invention.
• the samples were analyzed in GCxGC with cryogenic modulation (liquid nitrogen), programming of the first oven from 45 ° C (5 min) to 320 ° C (20 min) with a ramp of 3 ° C / min, a programming of the secondary oven from 60 ° C (5 min) up to 330 ° C (20 min) with a ramp of 3 ° C / min and columns used according to the following operating conditions:
• o 1 st dimension HP1, 25 m, ID 0.32 mm, film thickness: 0,17 ⁇ ;
• o 2nd dimension BPX-50, 1, 5m, 0.1 mm ID, film thickness: 0.1 ⁇ ;
• o injector split 100: 1, volume injected: 0.1 ⁇ ; o detector: FID, 320 ° C;
• o temperature of the hot jet 320 ° C;
• An 8L autoclave reactor is used. Before use, the reactor is dried at 130 ° C with a nitrogen flow for one hour and then cooled to 110 ° C. Then, it is filled with 3500 ml of 1-decene under a stream of nitrogen. The temperature of the reactor is maintained at 110 ° C. and hydrogen (H 2 ) is introduced at a ratio m / m H 2 /1-decene of 414 ppm.
• the catalyst is rac-ethylene bis (tetrahydroindenyl) zirconium dimethyl activated with dimethylanilinium tetrakis (perfluorophenyl) borate (DMAB) in a molar ratio B / Zr of 1.75.
• DMAB dimethylanilinium tetrakis (perfluorophenyl) borate
• B / Zr dimethylanilinium tetrakis (perfluorophenyl) borate
• TiBAI Triisobutyl aluminum
• the oligomerization begins at the time of introduction of the activated catalyst in a concentration of 17 ⁇ relative to the oligomerization solution.
• the hydrogenation of the reaction products is then carried out using a palladium catalyst supported on alumina (5 g of palladium on gamma-alumina at 5% w / w relative to the alumina - Alfa Aesar product) and the hydrogen (H 2 ) at 20 bar, at a temperature of 100 ° C, for 240 min.
• a palladium catalyst supported on alumina 5 g of palladium on gamma-alumina at 5% w / w relative to the alumina - Alfa Aesar product
• H 2 hydrogen
• the oligomerization products and the trimeric fraction comprising more than 50% by weight of 9-methyl-1-octyl-henicosane are then separated by distillation at reduced pressure (0.67 mBar or 0.5 mmHg) in two stages. according to ASTM D2892 and then according to ASTM D5236: (1) by means of a column with 15 theoretical plates whose maximum temperature is 375 ° C then (2) by means of a column with 2 theoretical plates whose The temperature of the vapors at the top of the column ranges from 375 to 445 ° C.
• Distillation according to ASTM D2892 makes it possible to separate products whose boiling point is below 375 ° C.
• Distillation according to ASTM D5236 makes it possible to isolate products whose boiling point ranges from 375 to 445 ° C.
• the oil according to the invention obtained has a content of 9-methyl-1-octyl-henicosane equal to 71.4%.
• This oil according to the invention comprising more than 50% by weight of 9-methyl-1-octyl-henicosane has a kinematic viscosity at 100 ° C., measured according to the ASTM standard. D445, of 3.448 mm 2 .s "1.
• the viscosity index of this oil is 130.
• Its volatility measured according to the ASTM D6375 standard is 10.3% by weight and its dynamic viscosity (CCS) at -35 ° C. C, measured according to ASTM D5293, is 780 mPa.s.
• Its average molecular weight is 372 g / mol.
• the characteristics of the oil according to the invention make it possible to obtain excellent lubricating, rheological and oxidation resistance properties as well as Fuel Eco.
• the oligomerization products and the trimeric fraction comprising more than 50% by weight of 9-methyl-1-octyl-henicosane are then separated by distillation at reduced pressure (0.67 mBar or 0.5 mmHg) in two stages. according to ASTM D2892 and then according to ASTM D5236: (1) by means of a column with 15 theoretical plates whose maximum temperature is 375 ° C then (2) by means of a column with 2 theoretical plates whose The temperature of the vapors at the top of the column is from 445 to 465 ° C.
• Distillation according to ASTM D2892 makes it possible to separate products whose boiling point is below 375 ° C.
• Distillation according to ASTM D5236 makes it possible to isolate products whose boiling point ranges from 445 to 465 ° C.
• the oil according to the invention obtained has a content of 9-methyl-1-octyl-henicosane equal to 65.7%.
• This oil according to the invention comprising more than 50% by weight of 9-methyl-1-octyl-henicosane has a kinematic viscosity at 100 ° C., measured according to the ASTM D445 standard, of 3,640 mm 2 ⁇ s -1 .
• the viscosity index of this oil is 132.
• Its volatility measured according to the ASTM D6375 standard is 9.1% by weight and its dynamic viscosity (CCS) at -35 ° C., measured according to the ASTM D5293 standard, is 890.degree. mPa.s.
• Its average molecular weight is 383 g / mol, again the characteristics of this oil according to the invention make it possible to obtain excellent lubricating, rheological and oxidation resistance properties, as well as of Fuel Eco. .
• Example 3 The procedure is identical to Example 1 to prepare a first oil fraction according to the invention. The procedure is identical to Example 2 to prepare a second oil fraction according to the invention. The two fractions are then pooled.
• the final hydrogenation is carried out using a palladium catalyst (0.5% w / w relative to H 2 ) supported on alumina (5 g of palladium on gamma-alumina at 5% w / w). alumina - Alfa Aesar product) and hydrogen (H 2 ) at 20 bar, at a temperature of 90 ° C, for 240 min.
• the oil according to the invention obtained has a content of 9-methyl-1-octyl-henicosane equal to 74.7%.
• This oil according to the invention comprising more than 50% by weight of 9-methyl-1-octyl-henicosane has a kinematic viscosity at 100 ° C., measured according to ASTM D445 standard, of 3.569 mm 2 ⁇ s -1 .
• the viscosity index of this oil is 130. Its volatility measured according to the ASTM D6375 standard is 10.3% by weight and its dynamic viscosity (CCS) at -35 ° C., measured according to the ASTM D5293 standard, is 720. mPa.s. Its average molecular weight is 378 g / mol.
• the characteristics of the oil according to the invention make it possible to obtain excellent lubricating, rheological and oxidation resistance properties as well as Fuel Eco.
• This reference PAO oil has a kinematic viscosity at 100 ° C as measured according to ASTM D445 of 3,671 mm 2. s "1. Its viscosity index is 1 18. Its volatility measured according to ASTM D6375 was 14.3 mass% and its dynamic viscosity (CCS) at -35 ° C, measured according to ASTM D5293 standard is 1,100 mPa.s. Its average molecular weight is 374 g / mol.
• kinematic viscosity at 100 ° C. measured according to the ASTM D445 standard, from 3.5 to 3.9 mm 2 .s -1 , volatility measured according to the ASTM D5800 lower standard. at 17% by weight.
• the process according to the invention thus makes it possible to prepare an oil whose properties are equivalent to or better than commercial PAO oils, in particular the viscosity index or the dynamic viscosity, which are much better for the oils according to the invention.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• General Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Lubricants (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=51610231

Family Applications (1)

Country Status (11)

Families Citing this family (14)

Family Cites Families (23)

• 2014
  • 2014-05-30 FR FR1454919A patent/FR3021664B1/fr not_active Expired - Fee Related
• 2015
  • 2015-05-29 EP EP15726134.8A patent/EP3149122A1/fr not_active Withdrawn
  • 2015-05-29 US US15/313,605 patent/US20170183594A1/en not_active Abandoned
  • 2015-05-29 MX MX2016015518A patent/MX2016015518A/es unknown
  • 2015-05-29 MA MA039911A patent/MA39911A/fr unknown
  • 2015-05-29 JP JP2017514972A patent/JP2017519097A/ja active Pending
  • 2015-05-29 CN CN201580027644.2A patent/CN106414680A/zh active Pending
  • 2015-05-29 KR KR1020167033618A patent/KR20170010778A/ko unknown
  • 2015-05-29 WO PCT/EP2015/061971 patent/WO2015181358A1/fr active Application Filing
  • 2015-05-29 CA CA2950123A patent/CA2950123A1/fr not_active Abandoned
• 2016
  • 2016-11-24 ZA ZA2016/08165A patent/ZA201608165B/en unknown

Also Published As

Similar Documents

Legal Events