EP0162890B1 - Hydroxy-polyätherpolyamine als additive zur steuerung des niederschlags - Google Patents

Hydroxy-polyätherpolyamine als additive zur steuerung des niederschlags Download PDF

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Publication number
EP0162890B1
EP0162890B1 EP84904244A EP84904244A EP0162890B1 EP 0162890 B1 EP0162890 B1 EP 0162890B1 EP 84904244 A EP84904244 A EP 84904244A EP 84904244 A EP84904244 A EP 84904244A EP 0162890 B1 EP0162890 B1 EP 0162890B1
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Prior art keywords
additive
fuel
hydrogen
independently
weight
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EP84904244A
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English (en)
French (fr)
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EP0162890A1 (de
EP0162890A4 (de
Inventor
Curtis B. Campbell
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Chevron USA Inc
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Chevron Research and Technology Co
Chevron Research Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • 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
    • C10N2040/251—Alcohol fueled engines
    • 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
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention is directed to hydroxy polyether polyamines, to fuel compositions and lubricating oil compositions containing these compounds and to their use as either fuel additives or detergent or dispersancy additives in lubricating oils.
  • Deposits adversely affect the operation of the vehicle. For example, deposits on the carburettor throttle body and venturies increase the fuel to air ratio of the gas mixture to the combustion chamber thereby increasing the amount of unburned hydrocarbon and carbon monoxide discharged from the chamber. The high fuel-air ratio also reduces the gas mileage obtainable from the vehicle.
  • each engine when new, requires a certain minimum octane fuel in order to operate satisfactorily without pinging and/or knocking. As the engine is operated on any gasoline, this minimum octane increases and, in most cases, if the engine is operated in the same fuel for a prolonged period, will reach an equilibrium. This is apparently caused by an amount of deposits in the combustion chamber. Equilibrium is typically reached after 5000 to 15000 miles of automobile operation.
  • the ORI problem is compounded by the fact that the most common method for increasing the octane rating of unleaded gasoline is to increase its aromatic content. This, however, eventually causes an even greater increase in the octane requirement. Moreover, some of presently used nitrogen-containing compounds used as deposit-control additives and their mineral oil or polymer carriers may also significantly contribute to ORI in engines using unleaded fuels.
  • the second complicating factor relates to oil solubility of the fuel additives.
  • Fuel additives due to their higher boiling point over gasoline itself, tend to accumulate on surfaces in the combustion chamber. This accumulation of the additive eventually finds its way into the lubricating oil via a "blow-by" process. In some cases this process may be of no concern as the fuel additives will be inert and compatible in the oil.
  • the additive is incompatible in the lubricating oil a serious problem develops as the accumulation of the additive results in an emulsion-like sludge which is detrimental to efficient operation. Therefore, it is particularly desirable that the gasoline additive be oil compatible.
  • the present invention also relates to lubricating oil compositions containing hydroxy polyether polyamines which contribute dispersancy and detergency to the compositions.
  • Lubricating oil compositions particularly for use in internal combustion engines, have long performed many functions other than simply lubricating moving parts. Modern-day, highly compounded lubricating oil compositions provide anti-wear, anti-oxidant, extreme-pressure and anti-rust protection in addition to maintaining the cleanliness of the engine by detergency and dispersancy. Many lubricating oil additives are well known for accomplishing these functions. For maintaining engine cleanliness, a well-known class of ashless detergents which have been found to be particularly useful are polyoxyalkylene carbamates.
  • Polyether amine-type fuel additives for deposit control and lubricating oil dispersancy are well-known but have traditionally been surfactant-type molecules having a large, non-polar hydrophobic end or "tail", for instance, a hydrocarbyl capped polyether moiety, and a polar, hydrophilic amine or polyamine end. Examples of these type of compositions may be found in U.S. Patent No. 4,247,301; U.S. Patent No. 4,160,648; and EP-A-0100665. In U.S. Patent No.
  • thermally stable distillate fuels which have been stabilized by means of an additive which is an oxyalkylation product formed by reacting certain polyamines with certain epoxides in an excess amount so that all the nitrogen atoms of the polyamine reactant will be attached to an oxyalkylene group derived from the epoxide reactant.
  • additives are provided which, when added to fuels or used as fuel concentrates, are effective in cleaning and maintaining the cleanliness of engine intake systems and when added at from 0.01 to 10 weight percent to lubricating oil, are effective in providing dispersancy and detergency to the oil.
  • the additives consist of certain fuel and lubricating oil soluble hydroxy polyoxyalkylene amines or polyamines. These additives have the following general formula: wherein:
  • compositions may be either mono or polyamines, but polyamines are preferred.
  • the additive compounds have molecular weights in the range from 500 to 2000, preferably from 700 to 1200.
  • the hydrophobic portion of a polyether polyamine fuel additive may contain an "uncapped" hydroxyl group, provided that the polyether is a co-polymer and that the portion of the co-polymer having the hydroxyl group has more carbon atoms per unit than the other portion of the block co-polymer.
  • a preferred compound is composed of a block co-polymer in which the hydroxyl-containing portion is composed of poly(butylene glycol) and the other portion is composed of poly(ethylene glycol).
  • R' has at least 2 carbon atoms, and R", R'" and R'" are H.
  • the compositions are selected to provide solubility in fuel compositions and deposit control activity without contributing to octane requirement increase (ORI).
  • the desired concentration of the additive will vary according to fuel type and quality and the presence or absence of other additives, etc. Generally, however, the concentration will be from 250 parts per million (ppm) by weight to 5000 ppm by weight. The preferred concentration is from 300 ppm to 2000 ppm.
  • the additive compositions may be used as concentrates, and could be used as additives to fuels subsequent to their preparation.
  • the weight percent of these additives will usually range from 0.3 to 50 weight percent.
  • the concentrate would ordinarily comprise an inert stable oleophilic organic solvent and the carrier of said solvent boiling in the range of from 150° to 400°F (65.5 to 204.4°C) and the concentrate would preferably contain from about 10 to 50 weight percent of the additive compound.
  • the specific compositions are selected to provide solubility in lubricating oil compositions with dispersant activity, without contributing to deposit formation in the lubricating oil composition.
  • the addition to the oil of from 0.01 to 10 weight percent of an additive of this invention is effective in providing dispersancy and detergency to the oil.
  • oils which find use in this invention are oils of lubricating viscosity derived from petroleum or synthetic sources. Oils of lubricating viscosity normally have viscosities in the range of 35 to 50,000 Saybolt Universal Seconds (SUS) at 37.6°C and more usually from about 50 to 10,000 SUS at 37.6°C.
  • base oils are naphthenic bases, paraffin base and mixed base mineral oils, synthetic oils; for example, alkylene polymers, such as the polymers of propylene, butylene, etc., and mixtures thereof.
  • oils besides the subject additives are such additives as dispersant/detergents, rust inhibitors, antioxidants, oiliness agents, foam inhibitors, viscosity index improvers, pour point depressants, etc.
  • these other additives will be present in amounts of from about 0.5 to 15 weight percent of the total composition.
  • each of the additives will be present in the range from about 0.01 to 5 weight percent of the total composition.
  • additive compositions may be used as lubricating oil concentrates, and could be used as additive to lubricating oils subsequent to their preparation.
  • weight percent of these additives will usually range from about 10 to 90 weight percent.
  • the additive compounds can be prepared by a variety of known processes.
  • an appropriate hydroxy-substituted amine containing both the desired amino moiety and the appropriate hydroxy-terminated alkyl moiety, is first reacted to form an alkali alkoxide salt which is then reacted with an appropriate alkylene oxide or other oxylating agent.
  • the resulting polyether amine is then reacted with a second epoxyalkane having the desired R' or R" brand alkyl groups, at least one of which has more than 2 carbon atoms.
  • a block co-polymer is produced having a hydroxyl group near the end of the second polyether moiety.
  • a halohydroxyalkylene preferably chlorohydroxyalkylene is first reacted at the hydroxy terminus with an appropriate alkylene oxide.
  • the halo group is then reacted with an amine or polyamine, preferably in excess to yield the hydroxy poly(oxyalkylene) amines or polyamines of this invention.
  • suitable halohydroxyalkylenes include 2-chloroethanol, 2-chloropropanol, and the like.
  • the resulting slurry was heated to approx. 90°C and 100 ml (1.16 moles) of distilled 1,2-epoxybutane was added over 30 minutes. After this addition, the reaction was stirred with heating for 30 minutes and then cooled to room temperature and stirred for 16 hours.
  • the reaction was quenched by adding approx. 200 ml of t-butanol and stirring 30 minutes, followed by approx. 50 ml of water.
  • the reaction was diluted with 300 ml ether and extracted with two 100 ml portions of water.
  • a Waukesha CFR single-cylinder engine is used. The run is carried out for 15 hours, at the end of which time the intake valve is removed, washed with hexane and weighed. The previously determined weight of the clean valve is subtracted from the weight of the valve. The difference between the two weights is the weight of the deposit with a lesser amount of deposit measured connoting a superior additive.
  • the operating conditions of the test are as follows: water jacket temperature 100°C; manifold vacuum of 29.5 cm Hg, intake mixture temperature of 50.2°C; air-fuel ratio of 12; ignition spark timing of 40° BTC; engine speed is 1800 rpm; and the crankcase oil is a commercial 30 W oil.
  • the amount of carbonaceous deposit in milligrams on the intake valves is measured and reported in the following Table I.

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

Claims (9)

1. Treibstoff- und schmieröllösliches Additiv für eine Bekämpfung von Ablagerungen in Motoren, wobei dieses Additiv ein Hydroxypolyetheramin oder -polyamin ist, in welchem der Polyetheranteil ein Copolymeres ist und der Teil des Copolymeren mit der Hydroxygruppe mehr Kohlenstoffatome pro Einheit enthält als der andere Teil des Copolymeren, und wobei das Additiv durch die allgemeine Formel
Figure imgb0007
wiedergegeben wird, worin R' und R" unabhängig voneinander Wasserstoff oder Alkylgruppen mit 1 bis 4 Kohlenstoffatomen sind, wenigstens einer der Substituenten
R' und R" wenigstens zwei Kohlenstoffatome aufweist,
R"' und R'" unabhängig voneinander Wasserstoff oder Methyl sind, R" und Rvi unabhängig voneinander Wasserstoff oder
Figure imgb0008
sind, wobei
z eine ganze Zahl von 1 bis 5 ist, und
x und y unabhängig voneinander ganze Zahlen von 1 bis 30 sind, und wobei das Additiv ein Molekulargewicht im Bereich von 500 bis 2000 besitzt.
2. Additiv nach Anspruch 1, wobei das Molekulargewicht im Bereich von 700 bis 1200 liegt.
3. Additiv nach Anspruch 1, wobei R' Ethyl ist, R" Wasserstoff ist, R"' und R'" Wasserstoff sind, R" und Rvi Wasserstoff sind und x einen durchschnittlichen Wert von 9 besitzt und y 2 ist.
4. Treibstoffzubereitung aus einer größeren Menge eines Kohlenwasserstofftreibstoffs, der im Benzinbereich siedet, und einem kleineren Teil eines Additivs gemäß einem der Ansprüche 1 bis 3.
5. Triebstoffzusammensetzung nach Anspruch 4, wobei die Konzentration des Additivs in dem Treibstoff 250 Teile pro Million bis 5000 Teile pro Million, bezogen auf das Gewicht, beträgt.
6. Treibstoffzusammensetzung nach Anspruch 5, wobei diese Konzentration 300 ppm, bezogen auf das Gewicht, bis 2000 ppm, bezogen auf das Gewicht, beträgt.
7. Konzentrat aus einem inerten stabilen oleophilen organischen Lösungsmittel, das im Bereich von 65,5° bis 204,4°C siedet, und 0,3 bis 50 Gew.-% eines Additivs gemäß einem der Ansprüche 1 bis 3.
8. Schmierölzubreitung aus einer größeren Menge eines Öls mit Schmierviskosität und einer kleineren Menge eines Additivs gemäß einem der Ansprüche 1 bis 3.
9. Schmierölzubreitung nach Anspruch 8, wobei der kleinere Anteil des Additivs 0,01 bis 10 Gew.-% der gesamten Zubereitung ausmacht.
EP84904244A 1983-10-31 1984-10-30 Hydroxy-polyätherpolyamine als additive zur steuerung des niederschlags Expired EP0162890B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US54755983A 1983-10-31 1983-10-31
US54755883A 1983-10-31 1983-10-31
US547558 1983-10-31
US547559 1983-10-31

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EP0162890A1 EP0162890A1 (de) 1985-12-04
EP0162890A4 EP0162890A4 (de) 1986-08-21
EP0162890B1 true EP0162890B1 (de) 1989-08-23

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WO (1) WO1985001956A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4684373A (en) * 1986-07-31 1987-08-04 Wynn Oil Company Gasoline additive composition
US4857073A (en) * 1987-08-27 1989-08-15 Wynn Oil Company Diesel fuel additive
DE3826608A1 (de) * 1988-08-05 1990-02-08 Basf Ag Polyetheramine oder polyetheraminderivate enthaltende kraftstoffe fuer ottomotoren
EP0524783A1 (de) * 1991-07-23 1993-01-27 Oceanfloor Limited Verwendung von Schmierölzusammensetzungen
JP3802244B2 (ja) * 1998-10-02 2006-07-26 三洋化成工業株式会社 燃料油用清浄剤及び燃料油組成物
FR2802207B1 (fr) 1999-12-08 2002-01-18 Inst Francais Du Petrole Derives de l'isosorbide utilisables dans des compositions detergentes pour carburants de type essence
JP2010510469A (ja) 2006-11-17 2010-04-02 サマーヒル バイオマス システムズ インコーポレイテッド 粉末燃料、粉末燃料のディスパージョン、および粉末燃料関連の燃焼装置

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231619A (en) * 1959-12-18 1966-01-25 Jefferson Chem Co Inc Basic primary amino polyether compositions
US3030197A (en) * 1960-11-22 1962-04-17 Petrolite Corp Thermally stable distillate fuels
US4251670A (en) * 1977-09-26 1981-02-17 Texaco Inc. Glycol polyether-acrylic acid-amine reaction product for fuel and mineral oils
US4247301A (en) * 1978-06-19 1981-01-27 Chevron Research Company Deposit control and dispersant additives

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WO1985001956A1 (en) 1985-05-09
EP0162890A1 (de) 1985-12-04
EP0162890A4 (de) 1986-08-21
DE3479515D1 (en) 1989-09-28

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