WO1994009092A1 - Additifs pour carburants de moteurs a allumage par etincelle et carburants qui les contiennent - Google Patents

Additifs pour carburants de moteurs a allumage par etincelle et carburants qui les contiennent Download PDF

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Publication number
WO1994009092A1
WO1994009092A1 PCT/DE1993/000944 DE9300944W WO9409092A1 WO 1994009092 A1 WO1994009092 A1 WO 1994009092A1 DE 9300944 W DE9300944 W DE 9300944W WO 9409092 A1 WO9409092 A1 WO 9409092A1
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WO
WIPO (PCT)
Prior art keywords
product
fuel
carbon atoms
additives
mol
Prior art date
Application number
PCT/DE1993/000944
Other languages
German (de)
English (en)
Inventor
Winfried Thielebeule
Peter Finmans
Original Assignee
RWE-DEA Aktiengesellschaft für Mineraloel und Chemie
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 RWE-DEA Aktiengesellschaft für Mineraloel und Chemie filed Critical RWE-DEA Aktiengesellschaft für Mineraloel und Chemie
Priority to AU51062/93A priority Critical patent/AU5106293A/en
Publication of WO1994009092A1 publication Critical patent/WO1994009092A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal

Definitions

  • the invention relates to fuel additives for Otto engines with excellent detergent behavior, which reduce or prevent the formation of deposits in the engines.
  • hydrocarbon fuels When burned in Otto engines, hydrocarbon fuels tend to deposit combustion residues on those parts of the engine that have a low operating temperature. This is particularly the case with components of the intake system, e.g. the intake valves, the case and can hinder the flow of inflowing fuel / air mixtures. Furthermore, fuel residues preferentially deposit on parts of the cylinder head. The deposits can change the ignition behavior of the compressed fuel mixture in such a way that serious engine damage is caused by so-called early ignition. Heavy occupancy of the inlet valves leads to changed control times, leaks and, as a result, lower efficiencies, which result in higher fuel consumption. Therefore additives are used, also called detergents, which reduce the formation of deposits.
  • alkenyl succinic acids Various derivatives of alkenyl succinic acids are known for this use. Alkali and alkaline earth salts show the desired properties, but lead to the formation of combustion residues that contain ash and can therefore no longer be accepted for ecological reasons. This disadvantage is avoided by metal ion-free derivatives. Alkenyl succinic acids, anhydrides and half amides lead to improvements (EP-A1-393 769). State of the art are also mono-alkenylsuccinimides of the general formula
  • substituents X and Y are important here, since these are largely responsible for the polarity of the molecule and thus for the surface-active property of the additives. Furthermore, the solubility in mineral oils or fuels is significantly influenced by the substituents. If substituents X with less than 50 carbon atoms are used, the solubility in hydrocarbons is restricted. In addition to its importance for the polarity, the substituent Y serves as a carrier material for nitrogen functions, since these obviously have a significant influence on the surface-active ones
  • the anchoring of the olefin to maleic anhydride in the production of the alkenylsuccinimides is often carried out in Alder's' ⁇ -Reactibn under the aspect of a side reaction desired in later reaction stages in the form of an amination using a chlorinated raw material. This process is because of but no longer accept the expected exposure of the detergent to halogen. See current procedures propose to use non-halogenated precursors for the preparation of the alkenyl succinic acid or anhydride and to use the nitrogen content of the molecule completely via the amine component to form amides or imides.
  • the formation of the substituent X uses olefins in the range Ci2 ⁇ C200.
  • the amine component is anchored to form an acid amide or acid imide function and consists of polyalkylene amines, see WO 90/03359 or US Pat. No. 4,098,585.
  • N- (partly also 0) -containing heterocyclic systems are also used to fix groups with high polarity and high nitrogen content as imides (US Pat. No. 4,548,724, US Pat. No. 4,460,381).
  • the present invention is based on the object.
  • additives which contain one or more alkenylsuccinic acid bisimides of the general formula
  • R ⁇ and R2 can be the same or different and mean a polybutenyl radical on average with 48 to 60 carbon atoms,
  • R3 and R4 are the same and represent alkylene with 2 to 3 carbon atoms and n represents a natural number from 3 to 5.
  • the fuel additives according to the invention are preferably those bisimides of the general formula
  • and R2 is a polybutenyl radical on average with 48 to 60 carbon atoms and in particular on average with about 54 carbon atoms, R3 and R are alkylene with 2 carbon atoms and, n is the number 3.
  • the substituent (s) R 1 and / or R 2 preferably have a polybutylene radical with an average molar mass of 700 to 800 g / mol and in particular about 760 g / mol.
  • the invention furthermore relates to fuels which contain such additives, the nitrogen concentration of the additive addition preferably being set to a value of 3 to 6 ppm.
  • the additive concentration in the fuel is in particular 100 to 210 ppm.
  • the product obtained in this way shows in the IR spectrum the bands typical of acid imides with ⁇ at 1708 cm -1 and X2 at 1450 cm -1 and x-
  • Product 2 1574 g of alkenyl succinic anhydride, as prepared above from MA and polybutene with an average molar mass of approx. 760 g / mol, were reacted with 324 g of pentaethylene hexamine (PEHA) in the presence of 400 g of toluene with the discharge of water. The mixture was then heated to 200 ° C. as described for product 1 and finally stripped at 200 ° C. and 2000 Pa in order to drive off solvents. The product obtained shows the characteristic band order with x- j in the IR spectrum
  • the nitrogen content is approximately 2.4%
  • Example 1 A fuel mixed with products 1-13, in accordance with Euro Super according to DIN 51 607, was used in a Daimler-Benz engine (MBM / 02 E, 2.3 1) according to DKA 6/90 a 40- hourly test run that simulates difficult driving conditions in city traffic.
  • the test was used to check the formation of deposits on the intake system, in particular the intake valves (keep clean test).
  • the deposits were assessed by means of a gravimetric determination and a visual assessment of the deposits on the rear sides of the inlet valve disks, each given as an average.
  • each inlet valve is divided into sectors, the condition of which is assessed separately and rated with a value on a scale of 0-10, the value 10 indicating a valve free of deposits.
  • the average over the sectors of all intake valves results in the so-called rating.
  • Example 1 A fuel mixed with bis- [polybutenylsuccinic acid] imides was tested according to Example 1 in 60-hour test runs for the formation of deposits on inlet valves.
  • the procedure for evaluating the results corresponds to example 1.
  • the results are listed in the following table:
  • product 13 is by far the best derivative of the series of tests. Compared to the second best derivative, better results are obtained with a dosage reduced by more than 35%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne des bis-(acide alcénylsuccinique)imides utilisés comme additifs pour des carburants de moteurs à allumage par étincelle, qui ont un comportement dispersant supérieur et qui réduisent ou empêchent la formation de dépôts dans les moteurs. L'invention concerne en outre des carburants qui contiennent ces additifs.
PCT/DE1993/000944 1992-10-09 1993-10-05 Additifs pour carburants de moteurs a allumage par etincelle et carburants qui les contiennent WO1994009092A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU51062/93A AU5106293A (en) 1992-10-09 1993-10-05 Fuel additives for spark ignition engines and fuels containing them

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4234032A DE4234032A1 (de) 1992-10-09 1992-10-09 Kraftstoff-Additive für Otto-Motoren und Kraftstoffe, die diese enthalten
DEP4234032.2 1992-10-09

Publications (1)

Publication Number Publication Date
WO1994009092A1 true WO1994009092A1 (fr) 1994-04-28

Family

ID=6470045

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1993/000944 WO1994009092A1 (fr) 1992-10-09 1993-10-05 Additifs pour carburants de moteurs a allumage par etincelle et carburants qui les contiennent

Country Status (3)

Country Link
AU (1) AU5106293A (fr)
DE (1) DE4234032A1 (fr)
WO (1) WO1994009092A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5792729A (en) * 1996-08-20 1998-08-11 Chevron Chemical Corporation Dispersant terpolymers
CA2437945A1 (fr) * 2001-02-14 2002-12-27 The Lubrizol Corporation Composition d'additifs pour carburants, composition de carburants et procede associe

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271295A (en) * 1965-02-23 1966-09-06 Betz Laboratories Process of heat transfer
US3401118A (en) * 1967-09-15 1968-09-10 Chevron Res Preparation of mixed alkenyl succinimides
GB1162436A (en) * 1967-03-18 1969-08-27 Orobis Ltd Ashless Dispersants
EP0271937A2 (fr) * 1986-11-28 1988-06-22 Shell Internationale Researchmaatschappij B.V. Composition lubrifiante
EP0376578A1 (fr) * 1988-12-30 1990-07-04 Mobil Oil Corporation Additifs de polyalkylene succinimide pour le contrôle de dépôt, et compositions de combustible les contenant
EP0441014A1 (fr) * 1990-02-06 1991-08-14 Ethyl Petroleum Additives Limited Compositions de contrôle des dépôts dans le système d'admission
EP0460957A2 (fr) * 1990-06-07 1991-12-11 Tonen Corporation Composition d'additifs pour essence
EP0482253A1 (fr) * 1990-10-23 1992-04-29 Ethyl Petroleum Additives Limited Compositions de combustible bonnes pour l'environnement, et additifs pour
WO1993020170A1 (fr) * 1992-04-03 1993-10-14 The Associated Octel Company Limited Compositions detersives polyvalentes pour essence

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1019751A (en) * 1973-03-30 1977-10-25 Mobil Oil Corporation Liquid hydrocarbon compositions containing straight chain polyalkenylsuccinimides
US5114435A (en) * 1988-12-30 1992-05-19 Mobil Oil Corporation Polyalkylene succinimide deposit control additives and fuel compositions containing same

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271295A (en) * 1965-02-23 1966-09-06 Betz Laboratories Process of heat transfer
GB1162436A (en) * 1967-03-18 1969-08-27 Orobis Ltd Ashless Dispersants
US3401118A (en) * 1967-09-15 1968-09-10 Chevron Res Preparation of mixed alkenyl succinimides
EP0271937A2 (fr) * 1986-11-28 1988-06-22 Shell Internationale Researchmaatschappij B.V. Composition lubrifiante
EP0376578A1 (fr) * 1988-12-30 1990-07-04 Mobil Oil Corporation Additifs de polyalkylene succinimide pour le contrôle de dépôt, et compositions de combustible les contenant
EP0441014A1 (fr) * 1990-02-06 1991-08-14 Ethyl Petroleum Additives Limited Compositions de contrôle des dépôts dans le système d'admission
EP0460957A2 (fr) * 1990-06-07 1991-12-11 Tonen Corporation Composition d'additifs pour essence
EP0482253A1 (fr) * 1990-10-23 1992-04-29 Ethyl Petroleum Additives Limited Compositions de combustible bonnes pour l'environnement, et additifs pour
WO1993020170A1 (fr) * 1992-04-03 1993-10-14 The Associated Octel Company Limited Compositions detersives polyvalentes pour essence

Also Published As

Publication number Publication date
AU5106293A (en) 1994-05-09
DE4234032A1 (de) 1994-04-14

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