EP1152050B1 - Huile synthétique à haut indice de viscosite et faible point d'écoulement - Google Patents

Huile synthétique à haut indice de viscosite et faible point d'écoulement Download PDF

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Publication number
EP1152050B1
EP1152050B1 EP01400978A EP01400978A EP1152050B1 EP 1152050 B1 EP1152050 B1 EP 1152050B1 EP 01400978 A EP01400978 A EP 01400978A EP 01400978 A EP01400978 A EP 01400978A EP 1152050 B1 EP1152050 B1 EP 1152050B1
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EP
European Patent Office
Prior art keywords
oil
oil base
carbon atoms
isomers
synthetic oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP01400978A
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German (de)
English (en)
French (fr)
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EP1152050A1 (fr
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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Publication of EP1152050B1 publication Critical patent/EP1152050B1/fr
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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 subject of the present invention is 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 benzene ring of which 2 hydrogen atoms have been substituted with aliphatic chains, and / or partially or completely hydrogenated dialkylbenzenes (dialkylcyclohexadiene, dialkylcyclohexene, dialkylcylclohexane).
  • dialkylbenzenes according to the invention can be represented according to the general formula I:
  • Dialkylbenzenes are compounds whose characteristics have been widely described.
  • the patent US 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 may be substituted in ortho or para.
  • the European patent EP 168534 describes the properties of synthetic oils of the same generic formula I.
  • R1 has between 2 and 4 carbon atoms and R2 between 14 and 18 carbon atoms.
  • 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 comprise between 6 and 18 carbon atoms.
  • the product is characterized by the presence of the phenyl group on the carbon 2 of the aliphatic chain with a level greater than 20% on one of the groups R1 or R2 and less than 20% on the other.
  • the present invention relates to a synthetic oil composed in whole or in part of dialkylbenzenes and / or dialkylbenzenes partially or totally hydrogenated.
  • the synthetic oil according to the invention can also be used as oil base or oil base additive and comprises at least one dialkylbenzene and / or at least one partially or totally 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 at least one of the alkyl groups is attached predominantly to the group A by the carbon 2 of the aliphatic chain.
  • the two alkyl groups are predominantly attached to the group A by the 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 the group A by the carbon 2 of the aliphatic chain and usually at least 80%, often at least 95%, and most often almost 100%.
  • oils according to the present invention have viscosity indices much higher than those which could be described in the prior art as well as very low pour points.
  • the physical properties of the oils described by formula I depend on the proportions of the ortho compound.
  • High viscosity indices and very low Noak volatilities have been found when the oil synthesized according to the invention comprises dialkylbenzenes partially or totally hydrogenated in proportions of between 1 and 20% by weight of ortho isomers and preferably between 3 and 15% weight
  • the oil comprises a benzene and / or cyclohexane and / or cyclohexene and / or cyclohexadienic ring having 2 substituents consisting of aliphatic chains in the meta position in proportions of between 1 and 50% and preferably between 3 and 50% by weight.
  • the oil comprises 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 of between 10 and 95% and between 40 and 95% by weight, more preferably.
  • the sum of the isomers present in the oil is equal to 100%.
  • the three isomers are present in the synthetic oil.
  • compositions of the synthetic oils according to the present invention can be obtained by adjusting the proportion of the isomers by simple addition of the ortho and / or meta and / or para isomers or by any other synthesis technique known to those skilled in the art. .
  • the dialkylabenzenes may for example be prepared by alkylation of benzene with olefins. For this reaction, benzene and pure alpha-olefins whose chain length varies between 6 and 20 carbon atoms and preferably between 8 and 20 atoms have been used.
  • olefins are mixed with benzene in a benzene to olefin molar ratio of from about 0.1: 1 to about 10: 1.
  • a ratio of 0.2: 1 to 6: 1 will be used and even more preferably 0, 5: 1 and 3: 1.
  • Benzene and tetradecene-1 are mixed in a benzene to olefin molar ratio of 1.5 mol / mol.
  • This feedstock is sent to a reactor containing a catalyst comprising 80% of Mordenite type zeolite and 20% of alumina.
  • the reactor pressure is 6 MPa.
  • the hourly volume velocity (volume of charge on the catalyst volume and per hour) is 1 liter / liter / hour.
  • the catalyst temperature is maintained at 180 ° C.
  • the reaction products contain unconverted benzene, monoalkylbenzenes and dialkylbenzenes. These dialkylbenzenes are separated from the other products by distillation.
  • the 1 H NMR spectrum of hydrogen teaches that at least one of the alkyl groups is attached predominantly to the benzene group by the carbon 2 of the aliphatic chain.
  • the 13 C NMR spectra also make 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 method used.
  • the figure 2 shows the chromatograms obtained by gas chromatography of the dialkyl symmetrical product C14-C14 obtained.
  • the benzene is mixed with decene-1 with a benzene to olefin molar ratio of 1.5 mol / mol.
  • the operating conditions are the same as those of Example 1. This charge after alkylation makes it possible to obtain C10 monoalkylbenzene which are separated by distillation.
  • the figure 2 shows spectrograms obtained by gas chromatography of the C10-C14 asymmetric dialkylated product obtained.
  • Tables 1 and 2 show the characteristics of so-called symmetrical dialkylbenzenes that is to say having two aliphatic chains having the same number of carbon.
  • Table 2 shows the characteristics of the so-called asymmetrical dialkylbenzenes that is to say having two aliphatic chains not having the same number of carbon.
  • the figure 3 shows the evolution of the pour point as a function of the total number of carbon atoms.
  • asymmetric dialkylbenzenes one of the alkyl groups bound to the benzene group containing 10 carbon atoms, the other containing between 10 and 18 carbon atoms
  • the figure 4 according to the invention, the evolution of the viscosity at 40 ° C as a function of the total number of carbon atoms.
  • the figure 5 shows the evolution of the viscosity index as a function of the total number of carbon atoms.
  • Table 3 presents a comparison of the characteristics of a C12-C12 dialkylbenzene according to the present invention and of the composition described in the patent.
  • US 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 the patent. US 3,173,965 essentially leading 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 the patent.
  • the oils obtained according to the present invention have, as previously mentioned, a much lower Noack volatility than that of the best lubricating base currently on the market.
  • Table 4 presents a comparison of 3 very close kinematic viscosity oils (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 octene cut is characterized in that it is branched.
  • the dialkylbenzene obtained C8R-C16 was compared with that obtained with an octene-1 (linear) or C8-C16. The results obtained are shown in Table 5.
  • the oils according to the invention can be advantageously hydrogenated according to any technique known to those skilled in the art.
  • the dialkylbenzenes are then converted at least in part to dialkylcyclohexadiene and / or dialkylcyclohexene and / or dialkylcyclohexane. This transformation makes it possible, while retaining the cold properties (pour point), to significantly improve the viscosity index.
  • oils were hydrogenated in a stirred batch reactor under a hydrogen pressure of 60 bar.
  • the catalyst contains 0.6% by weight of palladium deposited on alumina.
  • the temperature is 250 ° C and the reaction time is 16 hours.
  • Table 6 shows 2 examples obtained with the preceding oils.
  • Table 6 C10-C16 C10-C16 hydrogen C10-C18 C10-C18 hydrogen Viscosity at 40 ° C (cSt) 27.17 28.28 30.92 28.61 Viscosity at 100 ° C (cSt) 5,368 5,304 5.874 5,838 Viscosity index 136 139 136 139 Pour point (° C) - 33 - 33 - 21 - 21
  • the dialkyl benzenes were prepared by alkylation with HF and AlCl 3 .
  • the different ortho-meta-para isomers obtained are separated on molecular sieves.
  • 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 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 Huile synthétique à haut indice de viscosite et faible point d'écoulement Expired - Lifetime EP1152050B1 (fr)

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 EP1152050A1 (fr) 2001-11-07
EP1152050B1 true EP1152050B1 (fr) 2010-10-27

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EP01400978A Expired - Lifetime EP1152050B1 (fr) 2000-05-02 2001-04-17 Huile synthétique à haut indice de viscosite et faible point d'écoulement

Country Status (8)

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

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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
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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
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US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
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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
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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
EP1152050A1 (fr) 2001-11-07
KR100778728B1 (ko) 2007-11-27
BR0101657A (pt) 2001-12-18
KR20010111453A (ko) 2001-12-19

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