EP0356726B1 - Compositions d'essence contenant des esters d'acides polycarboxyliques et d'alcools à chaîne longue - Google Patents
Compositions d'essence contenant des esters d'acides polycarboxyliques et d'alcools à chaîne longue Download PDFInfo
- Publication number
- EP0356726B1 EP0356726B1 EP89114039A EP89114039A EP0356726B1 EP 0356726 B1 EP0356726 B1 EP 0356726B1 EP 89114039 A EP89114039 A EP 89114039A EP 89114039 A EP89114039 A EP 89114039A EP 0356726 B1 EP0356726 B1 EP 0356726B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fuel
- ester
- alcohol
- esters
- acid
- 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
Links
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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
Definitions
- the invention relates to fuels for internal combustion engines with improved properties containing esters of aromatic di-, tri- or tetracarboxylic acids and long-chain alcohols.
- the invention relates to fuel compositions for gasoline engines.
- additive packages are added to gasoline in amounts of up to 2500 mg / kg. These generally consist of detergents, corrosion inhibitors, oxidation inhibitors, anti-icing agents, carrier oils and solvents.
- Carrier oils primarily have the task of preventing the so-called valve plugging and ensuring a better distribution of the detergents.
- polyethers and esters as carrier oils are said to reduce the increase in the octane requirement of engines as the number of operating hours increases.
- esters as a gasoline additive has long been known. Their use as a gasoline additive is e.g. described in DE-OS 21 29 461. The esters mentioned there are, as expressly mentioned in the patent specification mentioned, thermally unstable.
- DE 23 16 535 trimellitic acid dodecyl ester and GB 1 217 468 contain esters of e.g. C12-C15 alcohols which have been prepared by oxosynthesis. In both cases predominantly unbranched alcohols should be used.
- thermally stable esters with a high molecular weight and based on branched alcohols are excellent carrier oils, which can save up to 30% of the usual detergents without the gasoline quality, ie the purifying effect in the intake and mixture formation system, worsened.
- the invention relates to fuel compositions which have a low content, 0.005 to 0.2% by weight, based on the composition of esters of aromatic di-, tri- and tetracarboxylic acids with long-chain aliphatic, only carbon, hydrogen and oxygen-containing alcohols, which by Hydroformylation of branched olefins have been produced, the total carbon number of the esters being at least 36 carbon atoms and the molecular weight being 550 to 1500, preferably 600 to 1200.
- esters to be used are prepared in a manner known per se by esterification or transesterification processes, the carboxyl groups being essentially completely esterified.
- Aromatic di-, tri- or tetracarboxylic acids are o-phthalic acid, isophthalic acid, terephthalic acid, trimesic acid, trimellitic acid and pyromellitic acid. Of these, o-phthalic acid is preferred.
- aliphatic ether alcohols each having an ether and hydroxyl group and having at least 17 carbon atoms, which can be isolated, for example, from the distillation residues of the oxo alcohols C8, C9, C10, C13 and C13 / C15 and which is believed to be can be characterized by the following general formula: where 7, 8, 9, 12 and 12 to 14 means.
- Fuels for internal combustion engines are organic, mostly hydrocarbon-containing liquids that are suitable for the operation of Otto, Wankel and diesel engines.
- hydrocarbons are also from coal Hydrogenation, alcohols of various origins and compositions and ethers such as methyl tertiary butyl ether contained therein. The admissible mixtures are mostly nationally defined worldwide.
- esters to be used according to the invention are generally the fuels together with detergents, such as amides of oleic acid, ethylenediaminetetraacetic acid according to EP-A-6527 or polyisobutenyl succinic acid, and in particular polybutenamines prepared from polybutene alcohol with NH3, aminoethylethanolamine, dimethylaminopropylamine, triethylene tetramine, or tetraethylene they are described in US-A-3,756,793, DE-A-21 25 039, EP 244 616, to which reference is hereby made, corrosion inhibitors, i.e.
- esters to be used according to the invention with polybutenamines is preferred, the ratio of the esters to the polybutenamines generally being 1: 2 to 3: 1.
- a carrier oil combination with polyethers or mineral oil is also possible; this enables a reduction in the ester content in relation to the polybutenamines or amides.
- 1150 g oxo oil from the cobalt-catalyzed production of iso-decanol with an OH number of 154, an acid number of 0.76, a saponification number of 36 and a CO number of 1.8 and with a predominant content of alcohols at 20 ° C -Atoms, are heated under reflux with 208 g phthalic anhydride, 0.2 g tetrabutyl orthotitanate and 150 g toluene on a water separator for 36 h. 28 g of water separate out and the acid number drops to 2.
- 1043 g of an ester mixture are obtained, which is characterized as follows:
- the following table shows the effect of known carrier oils and the esters to be used according to the invention in combination with known detergents in gasoline for internal combustion engines.
- the amounts of esters listed in the table were added unleaded premium petrol (RON 95; DIN 51607) and test bench tests were carried out with a 1.2 l Opel Kadett engine in accordance with CEC-F-O2-T-79.
- the reference oil RL 51 was used as engine oil.
- the table shows an increasing effect on the inlet valves of the 1.2 liter Opel Kadett with the molecular weight of the ester.
- Experiments 2 to 4 of the table show a gradual reduction in the intake valve deposits compared to operating with fuel without additives (experiment 1).
- a Solvent Neutral 500 with a viscosity of 17 mm2 / s at 100 ° C was used.
- a polypropylene glycol with a viscosity of 100 mm2 / s at 40 ° C was used.
- Experiments 4 to 8 are esters of high purity, ie OH number less than 1, acid number less than 0.1 and ash less than 1 mg / kg.
- the C25 phthalate was with an alcohol prepared, which was obtained by hydroformylation of a hexa-isobutene from the production of reactive polyisobutene according to DE-AS 27 02 604.
- the viscosity of this ester is 31 mm2 / s at 100 ° C.
- the recommended dosage of the commercial polybutenamine for formulations with mineral oil is 350 mg / kg.
- the esters according to the invention enable savings of about 30% in polymeric detergents. Results with other higher viscosity detergents are comparable.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Detergent Compositions (AREA)
Claims (14)
Cn+1H2n+3 - O - Cn+2H2n+4OH
dans laquelle n est mis pour 7, 8, 9, 12 et 12 à 14, et. les restes hydrocarbonés sont ramifiés.
Cn+1H2n+3 - O - Cn+2H2n+4OH
dans laquelle n est mis pour 7, 8, 9, 12 et 12 à 14, et les restes hydrocarbonés sont ramifiés.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3826797 | 1988-08-06 | ||
| DE3826797A DE3826797A1 (de) | 1988-08-06 | 1988-08-06 | Kraftstoffzusammensetzungen, die polycarbonsaeureester langkettiger alkohole enthalten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0356726A2 EP0356726A2 (fr) | 1990-03-07 |
| EP0356726A3 EP0356726A3 (en) | 1990-03-28 |
| EP0356726B1 true EP0356726B1 (fr) | 1992-05-13 |
Family
ID=6360387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89114039A Expired - Lifetime EP0356726B1 (fr) | 1988-08-06 | 1989-07-29 | Compositions d'essence contenant des esters d'acides polycarboxyliques et d'alcools à chaîne longue |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0356726B1 (fr) |
| DE (2) | DE3826797A1 (fr) |
| ES (1) | ES2030945T3 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0398100A1 (fr) * | 1989-05-19 | 1990-11-22 | BASF Aktiengesellschaft | Compositions de combustible contenant des produits d'alkoxylation |
| US5405419A (en) * | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool |
| US5405418A (en) * | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and an aromatic ester |
| EP0704519A1 (fr) | 1994-09-28 | 1996-04-03 | Basf Aktiengesellschaft | Mélange d'amines, polymères d'hydrocarbures et solvants huileux, convenant comme additif pour combustibles et lubrifiants |
| US5674950A (en) * | 1994-03-07 | 1997-10-07 | Exxon Chemical Patents Inc. | Polymers having terminal hydroxyl aldehyde, or alkylamino substitutents and derivatives thereof |
| US5691422A (en) * | 1994-03-07 | 1997-11-25 | Exxon Chemical Patents Inc. | Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof |
| US6267791B1 (en) | 1993-03-20 | 2001-07-31 | Basf Aktiengesellschaft | Mixtures suitable as fuel additives |
| US6660050B1 (en) | 2002-05-23 | 2003-12-09 | Chevron U.S.A. Inc. | Method for controlling deposits in the fuel reformer of a fuel cell system |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0781794B1 (fr) | 1995-12-19 | 2000-05-17 | Chevron Chemical Company LLC | Alkylphényl polyoxyalkylène amines à très longues chaínes, et compositions de combustible les contenant |
| US5637119A (en) | 1995-12-29 | 1997-06-10 | Chevron Chemical Company | Substituted aromatic polyalkyl ethers and fuel compositions containing the same |
| US5599359A (en) | 1995-12-29 | 1997-02-04 | Chevron Chemical Company | Polyalkylphenyl and polyalkyloxycarbonylphenyl hydroxybenzoates and fuel compositions containing the same |
| US5628803A (en) | 1995-12-29 | 1997-05-13 | Chevron Chemical Company | Polyalkylphenyl and polyalkyloxycarbonylphenyl amino and nitro benzoates and fuel compositions containing the same |
| US7824454B2 (en) | 2004-08-17 | 2010-11-02 | Chevron Oronite Company Llc | Fuel composition for rectifying fuel gauge sending unit problems |
| RU2487922C2 (ru) * | 2007-11-28 | 2013-07-20 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Бензиновые композиции |
| US8552122B2 (en) | 2009-03-31 | 2013-10-08 | The University Of Southern Mississippi | Amine-terminated telechelic polymers and precursors thereto and methods for their preparation |
| US8394898B2 (en) | 2009-07-31 | 2013-03-12 | The University Of Southern Mississippi | In situ formation of hydroxy chain end functional polyolefins |
| WO2011032857A2 (fr) | 2009-09-15 | 2011-03-24 | Basf Se | Utilisation de dérivés de composés aromatiques en tant que marqueurs pour des liquides |
| NZ768126A (en) | 2018-03-23 | 2025-07-25 | Chevron Usa Inc | Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines |
| MY205195A (en) | 2018-10-04 | 2024-10-07 | Chevron Usa Inc | Hydride donors as an additive for reducing low speed pre-ignition events |
| US11142715B2 (en) | 2018-11-07 | 2021-10-12 | Chevron U.S.A. Inc. | Amino alkanediols and carboxylate salts as additives for improving fuel efficiency |
| MY209110A (en) | 2018-11-15 | 2025-06-22 | Chevron Usa Inc | Composition and method for preventing or reducing low speed pre-ignition in spark-ignited internal combustion engines |
| CN113227332B (zh) | 2018-11-15 | 2024-01-12 | 雪佛龙奥伦耐有限责任公司 | 用于防止或降低火花点燃式内燃机的低速早燃的组合物和方法 |
| CN114341321A (zh) | 2019-09-10 | 2022-04-12 | 雪佛龙奥伦耐有限责任公司 | 通过燃料添加剂减少燃烧发动机的摩擦 |
| KR102861162B1 (ko) | 2020-07-07 | 2025-09-18 | 셰브런 오로나이트 컴퍼니 엘엘씨 | 인젝터 노즐 오손을 완화하고 미립자 배출물을 감소시키기 위한 연료 첨가제 |
| MY208247A (en) | 2020-09-17 | 2025-04-29 | Chevron Usa Inc | Aryloxy alkylamines as fuel additives for reducing injector fouling in direct injection spark ignition gasoline engines |
| AU2022249975A1 (en) | 2021-03-31 | 2023-10-05 | Chevron Oronite Company Llc | Fuel additives for reducing low speed pre-ignition events |
| JP2024511825A (ja) | 2021-03-31 | 2024-03-15 | シェブロン・オロナイト・カンパニー・エルエルシー | 低速でのプレイグニッション事象を軽減するための組成物 |
| MX2024004111A (es) | 2021-10-14 | 2024-04-19 | Chevron Usa Inc | Aditivos de combustible de poliamida. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL277036A (fr) * | 1961-04-12 | |||
| GB1217468A (en) * | 1969-04-18 | 1970-12-31 | Shell Int Research | Ester mixtures |
| GB1346765A (en) * | 1970-06-16 | 1974-02-13 | Shell Int Research | Fuel compositions |
| GB2081299B (en) * | 1980-07-29 | 1984-01-18 | Exxon Research Engineering Co | Two-stroke fuel-lubricant composition |
| DE3700363A1 (de) * | 1987-01-08 | 1988-07-21 | Basf Ag | Kraft- oder schmierstoffzusammensetzung und verwendung von polybutyl- oder polyisobutylderivaten in denselben |
-
1988
- 1988-08-06 DE DE3826797A patent/DE3826797A1/de not_active Withdrawn
-
1989
- 1989-07-29 DE DE8989114039T patent/DE58901397D1/de not_active Expired - Lifetime
- 1989-07-29 EP EP89114039A patent/EP0356726B1/fr not_active Expired - Lifetime
- 1989-07-29 ES ES198989114039T patent/ES2030945T3/es not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Römpps Chemie-Lexikon; Achte, neubearbeitete und erweiterte Auflage;Franckh'sche Verlagshandlung Stuttgart, Seiten 4507, 4508 u. 2101, 2102 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0398100A1 (fr) * | 1989-05-19 | 1990-11-22 | BASF Aktiengesellschaft | Compositions de combustible contenant des produits d'alkoxylation |
| US5123932A (en) * | 1989-05-19 | 1992-06-23 | Basf Aktiengesellschaft | Motor fuel compositions containing alkoxylation products |
| US6267791B1 (en) | 1993-03-20 | 2001-07-31 | Basf Aktiengesellschaft | Mixtures suitable as fuel additives |
| US5674950A (en) * | 1994-03-07 | 1997-10-07 | Exxon Chemical Patents Inc. | Polymers having terminal hydroxyl aldehyde, or alkylamino substitutents and derivatives thereof |
| US5691422A (en) * | 1994-03-07 | 1997-11-25 | Exxon Chemical Patents Inc. | Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof |
| US5777041A (en) * | 1994-03-07 | 1998-07-07 | Exxon Chemical Patents Inc | Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof |
| US5919869A (en) * | 1994-03-07 | 1999-07-06 | Exxon Chemical Patents, Inc. | Polymers having terminal hydroxyl, aldehyde, or alkylamino substituents and derivatives thereof |
| US5405419A (en) * | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool |
| US5405418A (en) * | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and an aromatic ester |
| EP0704519A1 (fr) | 1994-09-28 | 1996-04-03 | Basf Aktiengesellschaft | Mélange d'amines, polymères d'hydrocarbures et solvants huileux, convenant comme additif pour combustibles et lubrifiants |
| US6579329B1 (en) | 1994-09-28 | 2003-06-17 | Basf Ag | Mixture suitable as a fuel additive and lubricant additive and comprising amines, hydrocarbon polymers and carrier oils |
| US6660050B1 (en) | 2002-05-23 | 2003-12-09 | Chevron U.S.A. Inc. | Method for controlling deposits in the fuel reformer of a fuel cell system |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0356726A2 (fr) | 1990-03-07 |
| DE58901397D1 (de) | 1992-06-17 |
| DE3826797A1 (de) | 1990-02-08 |
| ES2030945T3 (es) | 1992-11-16 |
| EP0356726A3 (en) | 1990-03-28 |
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