EP1152050A1 - Synthetisches Öl mit hohem Viskositätsindex und mit niedrigem Fliesspunkt - Google Patents

Synthetisches Öl mit hohem Viskositätsindex und mit niedrigem Fliesspunkt Download PDF

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Publication number
EP1152050A1
EP1152050A1 EP01400978A EP01400978A EP1152050A1 EP 1152050 A1 EP1152050 A1 EP 1152050A1 EP 01400978 A EP01400978 A EP 01400978A EP 01400978 A EP01400978 A EP 01400978A EP 1152050 A1 EP1152050 A1 EP 1152050A1
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EP
European Patent Office
Prior art keywords
oil
oil base
additive according
carbon atoms
synthetic
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.)
Granted
Application number
EP01400978A
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English (en)
French (fr)
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EP1152050B1 (de
Inventor
Patrick Briot
Léon Lew
Serge Gauthier
Alain Forestiere
Eric Benazzi
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IFP Energies Nouvelles IFPEN
Industrias Veneco CA
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IFP Energies Nouvelles IFPEN
Industrias Veneco CA
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    • 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
    • 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
    • C10M105/06—Well-defined hydrocarbons aromatic
    • 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
    • C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
    • C10M127/04—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon well-defined aromatic

Definitions

  • the present invention relates to a synthetic oil or a synthetic oil base having high viscosity indices and more particularly viscosity indices greater than 100, very low pour points, and very low Noack volatility.
  • the synthetic oil which is the subject of the present invention contains dialkylbenzenes, that is to say a nucleus benzene of which 2 hydrogen atoms have been substituted by aliphatic chains, and / or partially or fully hydrogenated dialkylbenzenes (dialkylcyclohexadiene, dialkylcyclohexene, dialkylcylclohexane).
  • dialkylbenzenes according to the invention can be represented according to general formula I:
  • Dialkylbenzenes are compounds whose characteristics have been widely described.
  • US Patent 3,478,113 teaches the properties of a synthetic oil of the same general formula I.
  • R1 has between 6 and 15 carbon atoms and R2 between 14 and 24 carbon atoms.
  • the sum of the aliphatic carbon number must be between 20 and 30 carbon atoms.
  • the product can be substituted for ortho or para.
  • European patent EP 168534 describes the properties of synthetic oils with the same formula generic I.
  • R1 has between 2 and 4 carbon atoms and R2 between 14 and 18 atoms carbon.
  • These oils have in total between 23 and 28 carbon atoms which corresponds to between 17 and 22 aliphatic carbon atoms. The authors reveal good physical properties of these oils when one of the two alkyl chains is much shorter than the other.
  • R1 and R2 contain between 6 and 18 carbon atoms.
  • the product is characterized by the presence of the phenyl group on carbon 2 of the aliphatic chain with a rate higher than 20% on one of the R1 or R2 groups and lower than 20% on the other.
  • the present invention relates to a synthetic oil composed in whole or in part of dialkylbenzenes and / or of dialkylbenzenes partially or totally hydrogenated.
  • the synthetic oil according to the invention can also be used as an oil base or oil base additive and comprises at least one dialkylbenzene and / or at least one partially or fully hydrogenated dialkylbenzene, corresponds to a general chemical formula: R1-A-R2, in which R1 and R2 represent alkyl groups and A is a benzene and / or cyclohexane and / or cyclohexene and / or cyclohexadienic ring and is characterized in that it contains between 1 and 20% by weight of ortho isomers, and in that that at least one of the alkyl groups is predominantly attached to group A by carbon 2 of the aliphatic chain.
  • the two alkyl groups are predominantly attached to group A by carbon 2 of the aliphatic chain.
  • the term predominantly means that at least 50% of at least one of the alkyl groups is attached to group A by carbon 2 of the aliphatic chain and usually at least 80%, often at least 95% and most often practically 100%.
  • oils according to the present invention have viscosity indices much higher than those which have could be described in the prior art as well as very low pour points.
  • the physical properties of the oils described by the formula I depend on the proportions of the ortho compound. Strong viscosity indices and Noak volatilities very low were found when the oil synthesized according to the invention included partially or fully hydrogenated dialkylbenzenes in proportions of between 1 and 20% by weight of ortho isomers and preferably between 3 and 15% by weight.
  • the oil includes a benzene and / or cyclohexane and / or cyclohexene and / or cyclohexadienic ring having 2 substituents made up of aliphatic chains in meta position in proportions between 1 and 50% and preferably between 3 and 50% by weight.
  • the oil includes a benzene and / or cyclohexane and / or cyclohexene and / or cyclohexadienic ring having 2 substituents consisting of aliphatic chains in the para position in proportions between 10 and 95% and between 40 and 95% by weight even more preferably.
  • the sum of Isomers present in the oil is 100%.
  • the three isomers are present in synthetic oil.
  • compositions of the synthetic oils according to the present invention can be obtained by adjusting the proportion of isomers by simply adding the ortho and / or meta and / or para isomers or indifferently by all the synthesis techniques known to those skilled in the art.
  • Dialkylabenzenes can for example be prepared by alkylation of benzene with olefins.
  • benzene and pure alpha-olefins with chain length were used varies between 6 and 20 carbon atoms and preferably between 8 and 20 atoms.
  • olefins are mixed with benzene in a benzene to olefin molar ratio of about 0.1: 1 approximately 10: 1 Preferably, a ratio of between 0.2: 1 and 6: 1 and more will be used between 0.5: 1 and 3: 1.
  • Example 1 synthesis of symmetrical DABs (C14-C14).
  • Benzene and tetradecene-1 are mixed in a benzene to olefin molar ratio of 1.5 moles / mole.
  • This charge is sent to a reactor containing a catalyst comprising 80% of Mordenite type zeolite and 20% alumina.
  • the reactor pressure is 6 Mpa.
  • Speed hourly volume volume of charge on the volume of catalyst and per hour is 1 liter / liter / hour.
  • the temperature of the catalyst is maintained at 180 ° C.
  • the reaction products contain unconverted benzene, monoalkylbenzenes and dialkylbenzenes. These dialkylbenzenes are separated from other products by distillation.
  • NMR spectra of hydrogen and carbon 13 allow according to well known techniques skilled in the art, to determine the structural characteristics of the oils synthesized.
  • NMR spectra of hydrogen and carbon 13 allow according to well known techniques skilled in the art, to determine the structural characteristics of the oils synthesized.
  • the 1 H NMR spectrum of hydrogen teaches that at least one of the alkyl groups is predominantly attached to the benzene group by carbon 2 of the aliphatic chain.
  • the 13 C NMR spectra also makes it possible, according to techniques well known to those skilled in the art, to know the proportion of each of the ortho / meta / para isomers obtained by the synthesis process employed.
  • Figure 2 shows the chromatograms obtained by gas chromatography of the dialkylated product symmetrical C14-C14 obtained.
  • Example 2 synthesis of asymmetric DABs (C10-C14) .
  • the benzene is mixed with decene-1 with a benzene to olefin molar ratio of 1.5 moles / mole.
  • the operating conditions are the same as those of Example 1. This charge after alkylation allows C10 monoalkylbenzene to be obtained which are separated by distillation.
  • FIG. 2 shows the spectrograms obtained by gas chromatography of the dialkylated product asymmetric C10-C14 obtained.
  • Table 1 presents the characteristics of the so-called symmetrical dialkylbenzenes, that is to say comprising two aliphatic chains comprising the same number of carbon.
  • Table 2 presents the characteristics of so-called asymmetric dialkylbenzenes, that is to say comprising two aliphatic chains not having the same number of carbon.
  • Symmetrical ATMs C10-C10 C12-C12 C14-C14 C16-C16 C18-C18 C20-C20 Total number of aliphatic carbon atoms 20 24 28 32 36
  • Kinematic viscosity at 40 ° C in centistoke (cSt) 13.8 21.16 29.7 42.43 60.30 83.74 Kinematic viscosity at 100 ° C (cSt) 3,228 4.524 5.855 7.40 9.37 12.31
  • Figure 3 shows the evolution of the pour point as a function of the total number of atoms. carbon.
  • asymmetric dialkylbenzenes one of the alkyl groups linked to benzene group containing 10 carbon atoms, the other containing between 10 and 18 carbon atoms carbon.
  • Figure 4 shows according to the invention the change in viscosity at 40 ° C as a function of the total number carbon atoms.
  • FIG. 5 shows the evolution of the viscosity index as a function of the total number of atoms of carbon.
  • Table 3 presents a comparison of the characteristics of a C12-C12 dialkylbenzene according to the present invention and of the composition described in US Pat. No. 3,173,965 (example D / D ').
  • the 2 products were prepared with the same reagents according to the procedure according to the invention and that described in US Pat. No. 3,173,965 leading essentially to the exclusive formation of isomers in para.
  • composition according to the invention containing a mixture of ortho, meta, para isomers has a better viscosity index and a higher kinematic viscosity than the composition obtained according to the procedure described in US Patent 3,173,965.
  • the oils obtained according to the present invention have, as mentioned above, a Noack volatility much lower than that of the best lubricating base currently on the market.
  • Table 4 presents a comparison of 3 oils with very close kinematic viscosities (same class). Two of these lubricating bases are the subject of the present invention and the third is an oil obtained by polymerization of olefins and commonly called Poly-Alpha-Olefin 6 (or PAO 6).
  • This monoalkylbenzene was separated by distillation and mixed with an octene cut obtained by dimerization of butene according to the process developed by the applicant known as dimersol.
  • This octene cut is characterized by the fact that it is branched.
  • the dialkylbenzene obtained C8R-C16 was compared to that obtained with an octene-1 (linear), ie C8-C16. The results obtained are presented in Table 5.
  • the oils according to the invention can advantageously be hydrogenated according to any known technique of the skilled person.
  • the dialkylbenzenes are then transformed at least in part into dialkylcyclohexadiene and / or dialkylcyclohexene and / or dialkylcyclohexane. This transformation allows, while retaining the cold properties (pour point), to significantly improve the viscosity index.
  • oils were hydrogenated in a batch reactor with stirring under pressure 60 bars of hydrogen.
  • the catalyst contains 0.6% by weight of palladium deposited on alumina.
  • the temperature is 250 ° C and the reaction time 16 hours.
  • Table 6 shows 2 examples obtained with the preceding oils.
  • the benzene dialkyls were prepared by alkylation with HF and AlCl 3 .
  • the different ortho-meta-para isomers obtained are separated on a molecular sieve.
  • the 3 pure isomers are then mixed again so as to obtain ortho-meta-para isomeric proportions identical to those obtained by a dialkylation reaction of benzene when the mordenite is used as catalyst.
  • the properties obtained are substantially identical (Table 7).

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP01400978A 2000-05-02 2001-04-17 Synthetisches Öl mit hohem Viskositätsindex und mit niedrigem Fliesspunkt Expired - Lifetime EP1152050B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0005676 2000-05-02
FR0005676A FR2808533B1 (fr) 2000-05-02 2000-05-02 Huile synthetique a haut indice de viscosite et faible point d'ecoulement

Publications (2)

Publication Number Publication Date
EP1152050A1 true EP1152050A1 (de) 2001-11-07
EP1152050B1 EP1152050B1 (de) 2010-10-27

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Country Status (8)

Country Link
US (1) US6491809B1 (de)
EP (1) EP1152050B1 (de)
KR (1) KR100778728B1 (de)
AR (1) AR040919A1 (de)
BR (1) BR0101657B1 (de)
DE (1) DE60143330D1 (de)
ES (1) ES2352672T3 (de)
FR (1) FR2808533B1 (de)

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ATE302258T1 (de) * 2001-02-13 2005-09-15 Shell Int Research Schmierölzusammensetzung
CA2478195C (en) * 2002-03-06 2011-08-30 Exxonmobil Chemical Patents Inc. Improved hydrocarbon fluids
US9051419B2 (en) * 2002-06-14 2015-06-09 Richard H. Hall Polymer
US20050121360A1 (en) * 2003-12-08 2005-06-09 The Lubrizol Corporation Traction fluids by coupling of cyclic hydrocarbon monomers with olefins
US7244867B2 (en) * 2004-04-16 2007-07-17 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US20080275284A1 (en) 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8173851B2 (en) * 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20060100469A1 (en) 2004-04-16 2006-05-11 Waycuilis John J Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US7510674B2 (en) * 2004-12-01 2009-03-31 Chevron U.S.A. Inc. Dielectric fluids and processes for making same
WO2007066347A1 (en) * 2005-12-09 2007-06-14 Council Of Scientific & Industrial Research A composition of insulating fluid and process for the preparation thereof
US8329966B2 (en) * 2006-10-25 2012-12-11 Formosan Union Chemical Corp. Slightly branched dialkyl benzenes and related compositions
US8222467B2 (en) * 2007-02-12 2012-07-17 Exxonmobil Chemical Patents Inc. Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein
US20080300157A1 (en) * 2007-03-30 2008-12-04 Wu Margaret M Lubricating oil compositions having improved low temperature properties
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US7592295B1 (en) 2008-10-10 2009-09-22 Amyris Biotechnologies, Inc. Farnesene dimers and/or farnesane dimers and compositions thereof
US7691792B1 (en) 2009-09-21 2010-04-06 Amyris Biotechnologies, Inc. Lubricant compositions
US9074143B2 (en) * 2009-12-11 2015-07-07 Uop Llc Process for producing hydrocarbon fuel
US8193401B2 (en) * 2009-12-11 2012-06-05 Uop Llc Composition of hydrocarbon fuel
US8133446B2 (en) * 2009-12-11 2012-03-13 Uop Llc Apparatus for producing hydrocarbon fuel
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9068134B2 (en) 2011-12-02 2015-06-30 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
US9150812B2 (en) 2012-03-22 2015-10-06 Exxonmobil Research And Engineering Company Antioxidant combination and synthetic base oils containing the same
US9315756B2 (en) 2012-04-06 2016-04-19 Exxonmobil Research And Engineering Company Bio-feeds based hybrid group V base stocks and method of production thereof
EP2864456B1 (de) 2012-06-21 2018-10-31 Shell International Research Maatschappij B.V. Schmierölzusammensetzungen enthaltend schwere fischer-tropsch basisöle und alkyliertes aromaten basisöl
US20140187457A1 (en) 2013-01-03 2014-07-03 Exxonmobil Research And Engineering Company Lubricating compositions having improved shear stability
US20140274838A1 (en) * 2013-03-15 2014-09-18 Exxonmobil Research And Engineering Company Method for improving thermal-oxidative stability and elastomer compatibility
BR102013032982A2 (pt) * 2013-12-20 2015-09-08 Whirlpool Sa óleo, composição lubrificante com lubricidade melhorada e coeficiente de desempenho aumentado, usos e máquina de refrigeração

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US3478113A (en) * 1965-09-07 1969-11-11 Bray Oil Co Hydrocarbon hydraulic oil
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US3478113A (en) * 1965-09-07 1969-11-11 Bray Oil Co Hydrocarbon hydraulic oil
GB1253190A (de) * 1970-04-16 1971-11-10
GB1467366A (en) * 1973-11-26 1977-03-16 Continental Oil Co Preparation of synthetic hydrocarbon lubricants
US4148834A (en) * 1975-04-09 1979-04-10 Continental Oil Company Preparation of synthetic hydrocarbon lubricants
EP0168534A2 (de) * 1984-04-27 1986-01-22 Exxon Research And Engineering Company Dialkylaromate und hydrogenierte Dialkylaromate in synthetischen Schmierölen und speziellen Ölen

Also Published As

Publication number Publication date
US6491809B1 (en) 2002-12-10
BR0101657B1 (pt) 2011-04-05
FR2808533A1 (fr) 2001-11-09
ES2352672T3 (es) 2011-02-22
DE60143330D1 (de) 2010-12-09
FR2808533B1 (fr) 2002-08-16
AR040919A1 (es) 2005-04-27
EP1152050B1 (de) 2010-10-27
KR100778728B1 (ko) 2007-11-27
BR0101657A (pt) 2001-12-18
KR20010111453A (ko) 2001-12-19

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