EP2138556A1 - Composition de stabilisateur et d'additif pour moteurs à combustion - Google Patents

Composition de stabilisateur et d'additif pour moteurs à combustion Download PDF

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Publication number
EP2138556A1
EP2138556A1 EP09008342A EP09008342A EP2138556A1 EP 2138556 A1 EP2138556 A1 EP 2138556A1 EP 09008342 A EP09008342 A EP 09008342A EP 09008342 A EP09008342 A EP 09008342A EP 2138556 A1 EP2138556 A1 EP 2138556A1
Authority
EP
European Patent Office
Prior art keywords
component
oil
fatty acid
amount
carbodiimide
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
EP09008342A
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German (de)
English (en)
Other versions
EP2138556B1 (fr
Inventor
Volker Dr. Schäfer
Otto Heinrich Botz
Original Assignee
Natoil AG
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Publication date
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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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/042—Epoxides
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/2805—Esters 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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

Definitions

  • the invention relates to an additive composition for stabilizing crude oil, at least partially refined oil or synthetic esters, an additive composition containing this stabilizer and their use as lubricants in internal combustion engines and the stabilized crude oil, at least partially refined oil or synthetic ester itself.
  • polyesters-based plastics are subject to hydrolytic degradation due to aging processes. During the aging of these ester-group-containing plastics, carboxyl groups are released which accelerate the degradation of the plastics autocatalytically.
  • Anti-hydrolysis agents of various kinds are added as additives in order to intercept the autocatalytic free acid and render it ineffective.
  • the property of the NCN group of the carbodiimide is exploited, preferably to react with the carboxyl group to form acylated ureas.
  • carbodiimides as hydrolysis protection leads to good results, but is also associated with disadvantages. These include the toxicity of such compounds and the relatively high cost associated with the use of carbodiimides.
  • This hydrolysis protection agent is composed of epoxidized natural oils or fatty acid esters of unsaturated fatty acids and at least one epoxidized fatty acid glyceride, supplemented by bis [-2,6-diisopropylphenyl] carbodiimide.
  • Suitable natural oils include vegetable oils such as rapeseed oil, linseed oil, soybean oil and sunflower oil. In addition, as a natural oil and fish oil can be used.
  • the hydrolysis protection agent has a correspondingly markedly reduced carbodiimide content.
  • Vegetable oils themselves as they have become known as part of the said hydrolysis protection agent, are more and more used as environmentally friendly, biodegradable fluids in industrial applications.
  • this desirable use of vegetable oils in practice does not always succeed quite smoothly, because their property profile still has disadvantages for the particular application, so they must be modified.
  • suitable for hydraulic purposes lubricating oil u. a. containing at least one, already mentioned vegetable triglyceride oil, the selected pour point depressant, a metal deactivator performance additive and at least one aminophenol.
  • the present invention was based on the object of providing novel lubricant uses and, in addition, expanding the field of use of technical fluids based on plants.
  • the inventively proposed stabilizer is suitable for use in internal combustion engines.
  • the component A which is composed at least of the subcomponents a1 and a2, serves to bind the free acid which forms or basically exists in the case of the natural oils.
  • the autocatalysis can be effectively prevented. It has been found that the component A forms a depot, which can adequately buffer further acid.
  • the further component B serves as an antioxidant and thus additionally stabilizes the oil or the synthetic ester.
  • Component A may have as a further constituent a carbodiimide as component a3.
  • this carbodiimide is a bis [-2,6-diisopropylphenyl] carbodiimide.
  • the invention is not limited to the use of this particular carbodiimide.
  • Other carbodiimides can also be used.
  • Another industrially used carbodiimide in this connection is exemplified by poly (2,4,6-triisopropylbenzene-1,3-carbodiimide).
  • the stabilizers used according to the invention can particularly preferably also be used as an entire additive system. Then they contain a natural, preferably a vegetable oil having an oleic acid content of at least 80%, preferably at least 85%, more preferably of at least 90% as further component C.
  • a vegetable oil preferably sunflower seed oil can be used.
  • a lubricant is obtained, which shows very good lubricating properties, especially in the automotive sector and can significantly reduce the wear on the injection pump and in the engine.
  • component A has an overall epoxide content of at least 1.5% by weight. having. With this epoxy content, substantially complete capture of formed free acid can be ensured.
  • the natural oil as such or as the basis for the fatty acid ester according to (component a1) and / or the fatty acid glyceride according to (component a1) is preferably selected from rapeseed oil or rapeseed oil, linseed oil, soybean oil, sunflower seed oil or fish oil and mixtures thereof.
  • the epoxidized fatty acid esters are formed from the fatty acids mainly contained in the oils.
  • the oleic acid, stearic acid, palmitic acid, linoleic acid and ⁇ -linolenic acid are exemplary and not restrictive. In principle, however, the entire range of natural oils and thus not only the range of vegetable oils is available for the selection of the oil and thus according to the fatty acid esters and the fatty acid glyceride.
  • Advantageous stabilizer and additive systems are obtained when the (component a1) in an amount of 90 to 10 wt .-%, the (component a2) in an amount of 9.9 to 60 wt .-% and the (component a3 ) optionally in an amount of 0.1-30% by weight.
  • the component a3 and thus the carbodiimide component can also be omitted.
  • an excellent stabilizing effect results when components A and B together in an amount of 5 to 20% by weight, preferably 5 to 15% by weight, more preferably 5 to 10% by weight. are included.
  • the stabilizing efficiency is excellent when the component A is contained in an amount of 5 to 70% by weight, preferably 10 to 50% by weight, more preferably 30% - 40 wt .-%, component B in an amount of 5-70 wt .-%, preferably 10-50 wt .-%, particularly preferably from 30 to 40 wt .-% and component C in an amount of 5-50 %
  • component A is contained in an amount of 5 to 70% by weight, preferably 10 to 50% by weight, more preferably 30% - 40 wt .-%
  • component B in an amount of 5-70 wt .-%, preferably 10-50 wt .-%, particularly preferably from 30 to 40 wt .-% and component C in an amount of 5-50 %
  • component C in an amount of 5-50 %
  • preferably 10-40 wt .-%, particularly preferably from 10 to 30 wt .-% is contained in the additive system, wherein the weight percentages are based on the additive system, as it
  • the invention also relates to a stabilizing additive composition in the form of an additive system which comprises an epoxidized natural oil and / or a fatty acid ester as partial component a1 and at least one epoxidized natural fatty acid glyceride as partial component a2, which together form component A, and wherein, in addition, a hindered phenol is contained as component B.
  • Component A of the additive composition according to the invention may additionally comprise a carbodiimide as component a3, which is preferably, but not necessarily, a bis [-2,6-diisopropylphenyl] carbodiimide.
  • the additive composition according to the invention may additionally comprise a natural, preferably a vegetable oil with an oleic acid content of at least 80%, preferably at least 85%, particularly preferably at least 90%, as component C.
  • this oil is a sunflower oil.
  • inventive additive composition is to be seen in its suitability as a lubricant for internal combustion engines.
  • the invention further relates to a crude oil, an at least partially refined oil or a synthetic ester, which have a stabilizer of the type mentioned or an additive system having a composition and properties, as explained in more detail above with respect to the inventive use and the additive system.
  • Component A of the stabilizer according to the invention contains, for the purposes of the experiments carried out here, the three components a1 in the form of an epoxidized fatty acid ester, a2 in the form of an epoxidized natural fatty acid glyceride and a3 in the form of bis [-2,6-diisopropylphenyl] carbodiimide.
  • the preparation of the composite component A can be carried out as in the DE-B-103 49 168 described in more detail.
  • component A a product obtainable in the above-mentioned manner but commercially available under the name LUBIO Hystab 9 from Shufer Additivsysteme GmbH, Ludwigshafen, was used.
  • component B a sterically hindered phenol which is likewise commercially available under the name LUBIO AO 17 from Shufer Additivsysteme GmbH, Ludwigshafen, was used.
  • Component C is preferably a sunflower seed oil having an oleic acid content of about 90.92%.
  • an unrefined sunflower seed oil "90 plus” from Dr. Ing. Frische GmbH, available through T + T Oleochemie GmbH, Germany.
  • composition of the stabilizer or additive system used is a composition of the stabilizer or additive system used:
  • component A The sub-components of component A are generally mixed together by stirring at elevated temperature of about 50-70 ° C over a period of about 3 h and acting as an antioxidant component B is added after stirring and briefly mixed with the component A. Components A and B are then also added to component C by stirring.
  • test medium and the catalyst are filled together in a glass, which is introduced into the rotating container (so-called "rotary bomb") and this is then closed.
  • rotary bomb rotating container
  • the test medium is aged at the specified, constant speed and temperature for a fixed period of time as indicated above under test duration.
  • test parameters are the same as indicated under I. in the aging resistance test.
  • performance of the test procedure is the same as stated under I.
  • Acid value fresh oil in mg KOH / g oil Acid value used oil in mg KOH / g oil Change d. Acid number in% Trial 1 0.1 0.18 + 80 Trial 2 0.07 0.08 + 1 Trial 3 0.06 0.07 +/- 0 Kin. Viscous. [40 ° C] fresh oil in cstokes Kin. Viscous. [40 ° C] waste oil in cstokes Kin. Viscous. [40 ° C] in% Trial 1 29.61 29.61 +/- 0 Trial 2 29.29 29.48 +/- 0 Trial 3 29,45 29.12 +/- 0
  • Acid value fresh oil in mg KOH / g oil Acid value used oil in mg KOH / g oil Change d. Acid number in% Trial 3 0.08 0.28 + 250 Trial 4 0.06 0.10 + 17 Trial 5 0.04 0.04 +/- 0 Kin. Viscous. [40 ° C] fresh oil in cstokes Kin. Viscous. [40 ° C] waste oil in cstokes Kin. Viscous. [40 ° C] in% Trial 3 21.68 23.78 + 10 Trial 4 22.17 22,49 +/- 0 Trial 5 22.65 22.46 +/- 0
  • the change in the acid number represents the hydrolytic stability of a tribosystem.
  • High acid numbers can lead to decomposition of the oil by autocatalysis, whose cleavage products in turn lead to corrosion, deteriorated Elastomerver joskeit etc.
  • the classic oil-based SAE 10W40 motor oil is hydrolytically most stable, but shows an increase in acid number of 80% after aging due to decomposition. By adding the additive system, the acid number is gradually reduced before and after aging.
  • the FAME-added motor oil shows in the non-additive state, especially after aging, a drastic increase in acid number by 250%.
  • the unadditiere motor oil naturally shows a relatively high acid number, which increases even after aging up to 45%.
  • the acid number is reduced in fresh oil. After aging, little or no change in the acid number is observed.
  • the change in viscosity represents the thermal and oxidative stability of a tribosystem. High viscosity changes lead to increased pressures, poorer lubricating properties, etc. Responsible for this are polymerization and decomposition processes.
  • inventive additive system causes a significant improvement in hydrolytic, thermal and oxidative stability both in pure and contaminated with FAME engine oil and vegetable oil in the engine.
EP09008342.9A 2008-06-26 2009-06-25 Composition de stabilisateur et d'additif pour moteurs à combustion Active EP2138556B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH01004/08A CH703950B1 (de) 2008-06-26 2008-06-26 Stabilisator- und Additivzusammensetzung für Verbrennungsmotoren.

Publications (2)

Publication Number Publication Date
EP2138556A1 true EP2138556A1 (fr) 2009-12-30
EP2138556B1 EP2138556B1 (fr) 2014-02-19

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EP (1) EP2138556B1 (fr)
CH (1) CH703950B1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014180833A1 (fr) * 2013-05-07 2014-11-13 Rhein Chemie Rheinau Gmbh Procédé de préparation de formulations huileuses au moyen de carbodiimides définis
EP3053992A1 (fr) * 2015-02-09 2016-08-10 LANXESS Deutschland GmbH Biodiesel

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0992571A1 (fr) * 1998-10-09 2000-04-12 Exxon Research And Engineering Company Huiles lubrifiantes ayant une stabilité améliorée à l'oxydation
DE10349168A1 (de) 2003-10-22 2005-06-16 Schäfer, Volker, Dr. Verwendung und Herstellung von neuen Hydrolyseschutzmitteln
JP2007131825A (ja) * 2005-10-14 2007-05-31 Japan Energy Corp 潤滑油組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0992571A1 (fr) * 1998-10-09 2000-04-12 Exxon Research And Engineering Company Huiles lubrifiantes ayant une stabilité améliorée à l'oxydation
DE10349168A1 (de) 2003-10-22 2005-06-16 Schäfer, Volker, Dr. Verwendung und Herstellung von neuen Hydrolyseschutzmitteln
JP2007131825A (ja) * 2005-10-14 2007-05-31 Japan Energy Corp 潤滑油組成物

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE CHEMABS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2007, FISZER ET AL: "Oxidative stability of products of chemical modification of vegetable oils", XP002550840, Database accession no. 2007:0663862 *
DATABASE WPI Week 200744, Derwent World Patents Index; AN 2007-453005, XP002550841 *
FISZER ET AL: "Oxidative stability of products of chemical modification of vegetable oils", CHEMIK, vol. 58, no. 6, 2005, pages 351 - 354, XP009124288 *
PEREZ AT AL: "Use of pressurized differential scanning calometry (PDSC) to evaluate effectiveness of additives in vegatable oil lubricants", PROCEEDINGS OF ASME ICES03, vol. 40, 2003, pages 197 - 206, XP002550839 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014180833A1 (fr) * 2013-05-07 2014-11-13 Rhein Chemie Rheinau Gmbh Procédé de préparation de formulations huileuses au moyen de carbodiimides définis
US9464256B2 (en) * 2013-05-07 2016-10-11 Rhein Chemie Rheinau Gmbh Methods for producing oil formulations by means of certain carbodiimides
EP3053992A1 (fr) * 2015-02-09 2016-08-10 LANXESS Deutschland GmbH Biodiesel

Also Published As

Publication number Publication date
CH703950B1 (de) 2012-04-30
EP2138556B1 (fr) 2014-02-19

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