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WO2001016260A1 - Polycetones oligomeres - Google Patents

Polycetones oligomeres Download PDF

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Publication number
WO2001016260A1
WO2001016260A1 PCT/GB2000/003235 GB0003235W WO0116260A1 WO 2001016260 A1 WO2001016260 A1 WO 2001016260A1 GB 0003235 W GB0003235 W GB 0003235W WO 0116260 A1 WO0116260 A1 WO 0116260A1
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WO
WIPO (PCT)
Prior art keywords
oligomenc
ketone
lubricant composition
composition according
group
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.)
Ceased
Application number
PCT/GB2000/003235
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English (en)
Inventor
Stephen Boyde
Paul Alexander Cameron
Graham Ronald Eastham
Robert Paul Tooze
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to AU67103/00A priority Critical patent/AU6710300A/en
Publication of WO2001016260A1 publication Critical patent/WO2001016260A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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Definitions

  • This invention relates to oligomenc polyketones and in particular to the use of fluid oligome ⁇ c polyketones as lubricants
  • oligomenc polyketones used in the invention can be prepared by carbonylation of alkenes by reaction with carbon monoxide This process is known and useful products of the reaction include ketone polymers and carboxylic acids or esters However, it is believed that the use of oligomenc products of this process as lubricant compositions, as described in this invention, is novel
  • the invention comprises a lubricant composition
  • a lubricant composition comprising an oligomenc polyketone which is a fluid and which is obtainable by reacting an alkene containing from 4 to 20 carbon atoms with carbon monoxide
  • the oligomenc polyketone used in the lubricant composition of the invention is fluid, by which is taken to mean that the material will flow at room temperature More specifically, a material which has a viscosity of less than 0 1 m 2 s 1 at 20° C is generally considered to be a fluid
  • these compounds are oligomers which contain repeat units having the following structures
  • the oligomer will have a preponderance of repea ⁇ ng units of type (b) or (c) [ketone repeat units] and repeat units of type (a) [alkane repeat units] may be absent
  • the average number of repeat units [type (a) plus type (b) plus type (c)] in the oligomers of the invention is in the range 3 to 10 and more preferably is in the range 3 to 8
  • R-CH-CH 2 which is present in all of the repeating units is derived from the alkene which can be used to prepare the oligomers used in the invention and this alkene may be linear or branched
  • R is an alkyl group containing from 2 to 18 carbon atoms
  • the lubricant compositions of the invention comprise oligomenc ketones and those of particular use have a viscosity at 40 ° C in the range 2 to 1000 mm 2 s
  • the flash point of oligomers used in the invention is preferably higher than 120 ° C and more preferably higher than 200° C
  • the lubricant compositions preferably have a pour point less than 0 ° C and more preferably less than -20 ° C when determined by ASTM D97
  • a further desirable property of the oligomers used in the invention is a viscosity index as defined by ASTM D2270-93 of at least 50 and preferably at least 100
  • Another aspect of the invention comprises the use in a lubricating composition of an oligomenc polyketone which is a fluid and which is obtainable by reacting an alkene containing from 4 to 20 carbon atoms with carbon monoxide
  • the invention comprises a method of providing lubrication comprising using in a lubricating composition an oligomenc polyketone which is a fluid and which is obtainable by reacting an alkene containing from 4 to 20 carbon atoms with carbon monoxide
  • the oligomenc polyketone may be used as either a major component, i e greater than 75%, or a minor component, i e less than 25%, in the lubricating composition
  • a convenient method for the production of the oligomenc polyketones used in the invention is the reaction of a suitable alkene with carbon monoxide in the presence of a catalyst which is obtainable by combining a metal of one of Groups 8 to 1 1 or a compound thereof and a bidentate ligand which is a compound of a Group 15 or Group 16 element
  • Suitable metals of Groups 8 to 11 include cobalt, nickel, palladium, rhodium, platinum, copper, silver and gold Particularly preferred are platinum or palladium
  • Suitable compounds of such metals of Groups 8 to 11 include salts of such metals with, or compounds comprising, weakly co-ordinated anions derived from the following acids nitric acid, sulphuric acid, lower alkanoic (up to C 12 ) acids such as acetic acid and propionic acid, sulphonic acids such as methane sulphonic acid, chlorosulphonic acid, fluorosulphonic acid, tnfluoromethane
  • E 1 and E 2 are, independently, an element of Group 15 or Group 16 and R 1 to R 4 are, independently, substituted or unsubstituted aliphatic, cycloaliphatic, aromatic or heterocyclic groups or one or both of the entities R 1 -E 1 -R 2 and R 3 -E -R 4 represent a substituted or unsubstituted cyclic group with at least 5 ring atoms
  • the bivalent organic bridging group X is suitably an alkylene group, which may be branched, or a carbon chain interrupted by a hetero atom, such as an oxygen atom, or an, optionally substituted, aryl moiety to which the Group 15 or 16 atoms, E 1 and E 2 are linked on available adjacent carbon atoms
  • X is a linear alkylene group, it preferably contains 1 to 4 carbon atoms
  • Particularly suitable alkylene groups include the 1 ,3-propylene, 2,2'-d ⁇ ethyl-1 ,3-propylene, 2,4-butylene, 2,2'-d ⁇ benzyl-1 ,3-propylene, 2-methyl-2'-benzyl- 1 ,3-propylene and 1 ,2-ethylene groups
  • synthesis of some suitable diphenylphosphino substituted bidentate ligands is described by Bianchini et al in Macromolecules 1999, 32, 4183-4193
  • bridging groups include ortho-xylyl, 2,3-d ⁇ methylnaphthyl and 3,4-d ⁇ methylnaphthyl
  • bidentate ligands having substituted aryl backbones are b ⁇ s(d ⁇ phenylphosph ⁇ no)-o-xylene (also known as 1 ,2-b ⁇ s(d ⁇ phenylphosph ⁇ omethyl)benzene and b ⁇ s(4,8,d ⁇ methyl-2-phosphab ⁇ cyclo- [3,3,1]nonyl)-o-xylene (also known as limphos)
  • the bridging group X contains an aryl moiety, e g a phenyl group, this may optionally be substituted
  • Substituents may be organic groups, e g alkyl, particularly C , to C frustrating, aryl, alkoxy, carbalkoxy, halo, nitro, t
  • E 1 and E 2 are, independently, an element of Group 15 or Group 16 but, preferably E 1 and E 2 are the same element
  • E 1 and E 2 are phosphorus, nitrogen, arsenic, antimony or sulphur and especially preferred ligands are those in which both E 1 and E 2 are phosphorus or nitrogen
  • R 1 to R 4 are aliphatic groups, they may be branched or linear and preferably they contain up to 20 carbon atoms More preferably, they contain up to 10 carbon atoms and suitable groups include methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tertiary butyl, neopentyl, adamantyl and cyclohexyl groups
  • R 1 -E 1 -R 2 and/or R 3 -E 2 -R 4 represent cyclic groups
  • these groups contain at least 5 ring atoms and preferably from 6 to 9 ring atoms
  • Preferred cyclic groups are those in which R 1 with R 2 and/or R 3 with R 4 represent 1 ,4-cyclohexylene, 1 ,4-cycloheptylene, 1 ,3-cycloheptylene, 1 ,2-cyclooctylene, 1 ,3-cyclooctylene, 1 ,4-cyclooctyle ⁇ e, 1 ,5-cyclo- octylene, 2-methyl-1 ,5-cyclooctylene, 2,6-d ⁇ methyl-l ,4-cyclooctylene, 2,6-d ⁇ methyl- 1 ,5-cyclooctylene, 4-v ⁇ nylcyclohexene, norbornene, 5-methylene-2-norbornene,
  • R 1 to R" are aromatic groups they preferably contain not more than 18 carbon atoms, and particularly 6 to 14 carbon atoms.
  • suitable groups are substituted or unsubstituted naphthyl groups and, preferably, substituted or unsubstituted phenyl groups Suitable substituents are halogen atoms and alkyl, aryl, alkoxy, carboxy, carboalkoxy, acyl, trihalogenomethyl, cyano, dialkylami ⁇ o, sulphonyl alkyl and alkanoyloxy groups
  • R 1 to R are heterocyclic groups they preferably contain not more than 18 carbon atoms, and particularly 6 to 14 carbon atoms
  • suitable groups are pyrrole and substituted pyrroles, furan, 2-methylfuran, thiophene, pyndine and substituted py ⁇ dines and bipyndine
  • bidentate ligands include b ⁇ s(d ⁇ phenyl-phosph ⁇ no)-o-xylene (also known as 1 ,2-b ⁇ s(d ⁇ phenylphosph ⁇ nomethyl)benzene), b ⁇ s(4,8,d ⁇ methyl-2-phosphab ⁇ - cyclo[3,3,1]nonyl)-o-xylene (also known as limphos), 1 ,3-b ⁇ s(d ⁇ phenylphosph ⁇ no)propane and 1 ,3-b ⁇ s(d ⁇ phenylphosph ⁇ no)-2,2'-d ⁇ ethylpropane
  • the amount of bidentate ligand used can vary within wide limits
  • the bidentate ligand is present in an amount such that the ratio of the number of moles of the bidentate ligand present to the number of moles of the metal of Groups 8 to 11 present is from 1 1 to 1 50, e g 1 1 to 1 10 and particularly from 1 1 to 1 5
  • carbon monoxide and alkene are mixed in the presence of the catalyst
  • Gases other than carbon monoxide and which are inert in the reaction may also be present
  • gases include hydrogen, nitrogen, carbon dioxide and the noble gases such as argon
  • the catalyst is preformed before mixing with other ingredients of the reaction mixture
  • a solution of the ligand in, for example, an aromatic hydrocarbon is mixed with a solution of the metal compound in the same solvent at a temperature below about 60 ° C
  • Suitable solvents include benzene, toluene, isomers of xylene, mesitylene dichloromethane and tetrahydrofuran Frequently, some of the catalyst will precipitate out as the reaction proceeds but the yield can often be improved by evaporating the solvent
  • the isolated solid catalyst is then washed and dried before use
  • the process for preparing oligomers of the invention is preferably carried out at a temperature from 60 to 120° C, and particularly from 90 to 100° C
  • the process is conducted under a total pressure of from 1 x 10 5 N m 2 to 100 x 10 5 N m 2 and in particular from 5 x 10 5 N m 2 to 50 x 10 5 N m 2
  • the catalyst system may be used homogeneously or heterogeneously
  • the catalyst system is used homogeneously
  • the catalyst system is preferably in the liquid phase of the reaction mixture which may be formed by one or more of the reactants or by the use of a suitable solvent
  • Suitable solvents include one or more aprotic solvents such as ethers, e g diethyl ether, dimethyl ether, dimethyl ether of diethylene glycol, anisole and diphenyl ether, aromatic compounds, including halo variants of such compounds, e g benzene, toluene, ethyl benzene, o-xyiene, m-xylene, p-xylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, and p-dichlorobenzene alkanes, including halo variants of such compounds, e g hexane, heptane, 2,2 3-tr ⁇ methylpentane, methylene chloride and carbon tetrachlonde, nitriles, e g benzonitnle and acetonitnle, esters, e g methyl benzoate,
  • the amount of catalyst used can be varied quite widely, but, typically, is in the range 1 part catalyst to from 2000 to 5000 parts define by weight
  • Typical oxidants include 1 ,4-qu ⁇ non ⁇ c compounds such as 1 ,4-benzoqu ⁇ none or 1 ,4-naphthaqu ⁇ none and nitro compounds such as nitrobenzene or nitrofluoroborate (NOBF 4 )
  • the amount of oxidant present is usually sufficient to provide a molar ratio of metal to oxidant in the range 1 1 to 1 ⁇ 10 and, preferably, in the range 1 1 to 1 5
  • the reaction conditions can be arranged so that the desired oligomenc ketone is produced as a separate phase from the remaining reactants, thus leading to a more easily isolated product
  • the oligomenc ketones may optionally be further subjected to catalytic hydrogenatio ⁇ in order to remove any residual olefinic unsaturation present in the materials as produced and thereby increase the stability of the resulting materials
  • catalytic hydrogenation processes are well known and are described in standard reference texts such as Ullmann's Encyclopaedia of Industrial Chemistry, Volume A13, p 487, Hydrogenation and dehydrogenation (P N Rylander)
  • the lubricating compositions of the invention are suitable for use in mechanical devices, principally acting as lubricants but also capable of performing as functional fluids for example as heat transfer fluids or hydraulic fluids They are useful in internal combustion engines in gear mechanisms in hydraulic systems and in other mechanical devices such as air compressors or gas compressors for refrigeration They are also useful as lubricants in industrial processes including metal working, textile manufacture etc
  • the oligomenc ketones may be used alone or mixed with other materials commonly used as lubricants or functional fluids, such as mineral oils or synthetic oils such as hydrocarbons (e g poly alphaolefins, poly( ⁇ sobutylenes) or alkylbenzenes), esters including phosphate esters or polyalkylene oxides
  • the oligomenc ketones may be used as modifying components with such other materials in levels ranging from 1 to 10% of the lubricant composition
  • the lubricant compositions of the invention are frequently formulated with conventional additives such as oxidation inhibitors, metal or copper deactivators
  • Example 2 The compound was prepared in an analogous fashion to Example 1 , except using a filtered solution of pallad ⁇ um(ll) acetate (0 96 g, 4 27 mmo ⁇ ) in toluene (120 cm 3 ) and dppp', as prepared in Example 2 (2 00 g 4 27 mmol) in toluene (50 cm 3 ) The product was isolated as a pale orange powder Yield 2 10 g, 71 %
  • oligomer from Example 7 was mixed with test materials including solvent neutral mineral oils and a standard additive package available as Lub ⁇ zol 9828A used in automotive engine crankcase lubricant formulations The mixed samples were then examined after 2 hours and again after 24 hours to check that the components were fully miscible, i e that they had formed a single liquid phase Results are given below in Table 2
  • test fluid was prepared by adding 1 % of a standard antioxidant, Irganox L06 available from Ciba Geigy, to the oligomer from Example 7
  • Test pieces of standard elastomenc materials were immersed in portions of the test fluid, and stored at 1 10° C for 7 days The weight of the test pieces was measured at the beginning and end of the test, and the difference determined as a measure of the swelling tendency of the test fluid towards these materials Results are given below in Table 3
  • test fluid is expected to be compatible with standard elastomenc materials

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Abstract

La présente invention concerne une composition lubrifiante comprenant une cétone oligomère fluide obtenue par réaction d'un alcène, comprenant de 4 à 20 atomes de carbone, avec du monoxyde de carbone en présence d'un catalyseur obtenu par combinaison d'un métal de transition, ou d'un composé de métal de transition, et d'un ligand bidenté.
PCT/GB2000/003235 1999-09-01 2000-08-22 Polycetones oligomeres Ceased WO2001016260A1 (fr)

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AU67103/00A AU6710300A (en) 1999-09-01 2000-08-22 Oligomeric polyketones

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GB9920516.3 1999-09-01
GBGB9920516.3A GB9920516D0 (en) 1999-09-01 1999-09-01 Oligomeric polyketones

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002014248A3 (fr) * 2000-08-14 2002-07-04 Sasol Tech Pty Ltd Production de produits oxygenes
WO2002006416A3 (fr) * 2000-07-18 2002-08-29 Exxonmobil Res & Eng Co Utilisation de polymeres a base de monoxyde de carbone comme additifs adhesifs et fluides
WO2003068786A1 (fr) * 2002-02-13 2003-08-21 Cytec Technology Corp Composes de phosphine
US8207364B2 (en) 2009-05-26 2012-06-26 Johnson Matthey Public Limited Company Process for preparing a complex
CN109715767A (zh) * 2016-07-22 2019-05-03 路博润公司 用于完全配制的润滑组合物的脂族四面体硼酸盐化合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2289895A (en) * 1994-05-31 1995-12-06 Shell Int Research Preparation of copolymers of carbon monoxide and an alpha-olefin having more than 10 carbon atoms
WO1995032998A1 (fr) * 1994-05-31 1995-12-07 Shell Internationale Research Maatschappij B.V. PREPARATION DE COPOLYMERES DE MONOXYDE DE CARBONE ET D'UNE αOLEFINE ALIPHATIQUE

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2289895A (en) * 1994-05-31 1995-12-06 Shell Int Research Preparation of copolymers of carbon monoxide and an alpha-olefin having more than 10 carbon atoms
WO1995032998A1 (fr) * 1994-05-31 1995-12-07 Shell Internationale Research Maatschappij B.V. PREPARATION DE COPOLYMERES DE MONOXYDE DE CARBONE ET D'UNE αOLEFINE ALIPHATIQUE

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002006416A3 (fr) * 2000-07-18 2002-08-29 Exxonmobil Res & Eng Co Utilisation de polymeres a base de monoxyde de carbone comme additifs adhesifs et fluides
US6573226B2 (en) 2000-07-18 2003-06-03 Exxonmobil Research And Engineering Company Use of carbon monoxide containing polymers as, adhesive additives, and fluids
WO2002014248A3 (fr) * 2000-08-14 2002-07-04 Sasol Tech Pty Ltd Production de produits oxygenes
US6717018B2 (en) 2000-08-14 2004-04-06 Sasol Technology (Proprietary) Limited Production of oxygenated products
WO2003068786A1 (fr) * 2002-02-13 2003-08-21 Cytec Technology Corp Composes de phosphine
US8207364B2 (en) 2009-05-26 2012-06-26 Johnson Matthey Public Limited Company Process for preparing a complex
CN109715767A (zh) * 2016-07-22 2019-05-03 路博润公司 用于完全配制的润滑组合物的脂族四面体硼酸盐化合物
CN109715767B (zh) * 2016-07-22 2022-01-21 路博润公司 用于完全配制的润滑组合物的脂族四面体硼酸盐化合物

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