EP0608149A1 - Additifs pour combustibles - Google Patents
Additifs pour combustibles Download PDFInfo
- Publication number
- EP0608149A1 EP0608149A1 EP94300481A EP94300481A EP0608149A1 EP 0608149 A1 EP0608149 A1 EP 0608149A1 EP 94300481 A EP94300481 A EP 94300481A EP 94300481 A EP94300481 A EP 94300481A EP 0608149 A1 EP0608149 A1 EP 0608149A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- alcohol
- carbon atoms
- ester
- fuel 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.)
- Withdrawn
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, 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
Definitions
- This invention relates to additives for reducing fuel consumption in compression-ignition (or diesel) engines.
- esters as additives for diesel engine fuel.
- US-A-2,527,889 describes polyhydroxy alcohol esters as primary anti-corrosion additives in diesel engine fuel
- GB-A-1,505,302 describes ester combinations including, for example, glycerol monoesters and glycerol diesters as diesel fuel additives, the combinations being described as leading to advantages including less wear of the fuel-injection equipment, piston rings and cylinder liners.
- neither document describes use ofthe esters for reducing fuel consumption.
- EP-A-0227 218 describes a method of reducing fuel consumption in an automotive internal combustion engine which comprises operating said engine on a gasoline hydrocarbon fuel, especially an unleaded fuel, containing an effective fuel reducing amount of a selected additive which is an hydroxyl-containing ester of a monocarboxylic acid and a glycol ortrihydric alcohol, said esteradditive having at least one free hydroxyl group.
- a first aspect of the invention is the use of an ester as an additive in a liquid hydrocarbon compression-ignition fuel oil for reducing consumption of the fuel oil operated in a compression-ignition engine, the ester being an ester of a carboxylic acid and an alcohol wherein the acid has from 2 to 50 carbon atoms and the alcohol has one or more carbon atoms.
- a second aspect of the invention is a method of reducing fuel consumption of a compression-ignition engine operated on a liquid hydrocarbon compression-ignition fuel oil, which method comprises operating the engine on a liquid hydrocarbon compression-ignition fuel oil containing , as an additive, a minor proportion of an ester as defined in the first aspect, sufficient to reduce said fuel consumption.
- the acid from which the ester is derived may be a mono or polycarboxylic acid such as aliphatic, saturated or unsaturated, straight or branched chain, mono and dicarboxylic acids being preferred.
- the acid may be generalised in the formula where x represents an integer and is 1 or more such as 1 to 4, and R' represents a hydrocarbyl group having from 2 to 50 carbon atoms and which is mono or polyvalent corresponding to the value of x, the - COOH groups, when more than one is present, optionally being substituent on different carbon atoms from one another.
- 'Hydrocarbyl means a group containing carbon and hydrogen which group is connected to the rest of the molecule via a carbon atom. It may be straight or branched chain which chain may be interrupted by one or more hetero atoms such as O, S, N or P, may be saturated or unsaturated, may be aliphatic or alicyclic or aromatic including heterocyclic, or may be substituted or unsubstituted.
- the hydrocarbyl group is an alkyl group or an alkenyl group having 10 (e.g. 12) to 30 carbon atoms, i.e. the acid is saturated or unsaturated.
- the alkenyl group may have one or more double bonds, such as 1, 2 or 3.
- saturated carboxylic acids are those with 10 to 22 carbon atoms such as capric, lauric, myristic, palmitic, and behenic acids and examples of unsaturated carboxylic acids are those with 10 to 22 carbon atoms such as oleic, elaidic, palmitoleic, petroselic, riconoleic, eleostearic, linoleic, linolenic, eicosanoic, galoleic, erucic and hypogeic acids.
- the acid is polycarboxylic, having for example from 2 to 4 carboxy groups
- the hydrocarbyl group is preferably a substituted or unsubstituted polymethylene.
- the alcohol from which the ester is derived may be a mono or polyhydroxy alcohol such as a trihydroxy alcohol.
- the alcohol may be generalised in the formula where y represents an integer and is 1 or more and R 2 represents a hydrocarbyl group having 1 or more carbon atoms such as up to 10 carbon atoms, and which is mono or polyvalent corresponding to the value of y the -OH groups, when more than one is present, optionally being substituent on different carbon atoms from one another.
- the hydrocarbyl group is preferably an alkyl group or a substituted or unsubstituted polymethylene group.
- monohydric alcohols are lower alkyl alcohols having from 1 to 6 carbon atoms such as methyl, ethyl, propyl and butyl alcohols.
- polyhydric alcohols are aliphatic, saturated or unsaturated, straight chain or branched alcohols having 2 to 10, preferably 2 to 6, more preferably 2 to 4, hydroxy groups, and having 2 to 90, preferably 2 to 30, more preferably 2 to 12, most preferably 2 to 5, carbon atoms in the molecule.
- the polyhydric alcohol may be a glycol or diol, or a trihydric alcohol such as glycerol.
- the esters may be used alone or as mixtures of one or more esters.
- esters examples include lower alkyl esters, such as methyl esters, of the above exemplified saturated or unsaturated monocarboxylic acids. Such esters may, for example, be obtained by saponification and esterification of natural fats and oils of plant or animal origin or by their transesterification with lower aliphatic alcohols.
- esters of polyhydric alcohols that may be used are those where all of the hydroxy groups are esterified, those where not all of the hydroxy groups are esterified, and mixtures thereof.
- Specific examples are esters prepared from trihydric alcohols are one or more of the above-mentioned saturated or unsaturated carboxylic acids, such as glycerol monoesters and glycerol diesters, e.g. glycerol monooleate, glycerol dioleate and glycerol monostearate.
- Such polyhydric esters may be prepared by esterification as described in the art and/or may be commercially available.
- This invention is preferably applicable to middle distillate fuel oils which generally boil within the range of about 100°C to about 500°C, e.g. about 150°C to about400°C.
- the fuel oil can comprise atmospheric distillate or vacuum distillate, or cracked gas oil or a blend in any proportion of straight run and thermally and/or catalytically cracked distillates, or may be a vegetable oi I or a derivative thereof such as an ester made by saponification and re-esterification or by transesterification.
- the most common petroleum distillates are kerosene, jet fuels, diesel fuels, heating oils and heavy fuel oils.
- the heating oil may be a straight atmospheric distillate, or it may contain amounts, e.g. up to 35% by weight of vacuum gas oil or of cracked gas oils or of both.
- the concentration of the additive of the invention in the fuel oil may be up to 250,000 ppm such as 1 to 2000 ppm (active ingredient) by weight perweight of fuel, preferably 5 or 10 to 500 or 1000 ppm, more preferably 5 or 10 to 200 or 500 ppm.
- the additive may be incorporated into bulk fuel oil by methods known in the art.
- the additive may be so incorporated in the form of a concentrate comprising an admixture of the additive and a liquid carrier medium compatible with the fuel oil, the additive being dispersed in the liquid medium.
- Such concentrates preferably contain from 3 to 75 wt%, more preferably 3 to 60 wt%, most preferably 10 to 50 wt% of the additive, preferably in solution in the oil.
- carrier liquid are organic solvents including normal paraffins, isoparaffins, naphthenics, aromatics and alcohols. The carrier liquid must of course be selected having regard to its compatibility with the additive and with the fuel.
- the fuel oil has one or more of a sulphur concentration of 0.2% by weight or less.
- the sulphur concentration is 0.05% by weight or less, such as 0.01% by weight or less.
- the art describes methods for reducing the sulphur concentration of hydrocarbon distillate fuels, such methods including for example solvent extraction, sulphuric acid treatment, and hydrodesulphurisation.
- the additives of the invention may be used singly or as mixtures of more than one additive. They may also be used in combination with one or more co-additives such as known in the art, for example the following: detergents, antioxidants (to avoid fuel degradation), corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, lubricity additives, and middle distillate cold flow improvers.
- co-additives such as known in the art, for example the following: detergents, antioxidants (to avoid fuel degradation), corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, lubricity additives, and middle distillate cold flow improvers.
- A An ester obtained by reacting a C36 dimer acid with ethylene glycol and 'neutralising' acid groups with methanol.
- the fuel consumption using treated fuel is better than, ie. lower than, that using untreated fuel.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939301119A GB9301119D0 (en) | 1993-01-21 | 1993-01-21 | Fuel composition |
GB9301119 | 1993-01-21 | ||
GB9322857 | 1993-11-05 | ||
GB939322857A GB9322857D0 (en) | 1993-11-05 | 1993-11-05 | Fuel additives |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0608149A1 true EP0608149A1 (fr) | 1994-07-27 |
Family
ID=26302321
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94300481A Withdrawn EP0608149A1 (fr) | 1993-01-21 | 1994-01-21 | Additifs pour combustibles |
Country Status (1)
Country | Link |
---|---|
EP (1) | EP0608149A1 (fr) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
US5632785A (en) * | 1995-12-01 | 1997-05-27 | Exxon Research & Engineering Company | Fuel economy additives |
US5855628A (en) * | 1995-04-24 | 1999-01-05 | Kao Corporation | Gas oil compositions and gas oil additives |
US5891203A (en) * | 1998-01-20 | 1999-04-06 | Ethyl Corporation | Fuel lubricity from blends of a diethanolamine derivative and biodiesel |
US5993498A (en) * | 1996-09-13 | 1999-11-30 | Exxon Research And Engineering Co. | Polyol ester distillate fuels additive |
US6001141A (en) * | 1996-11-12 | 1999-12-14 | Ethyl Petroleum Additives, Ltd. | Fuel additive |
US6429324B1 (en) | 1997-12-13 | 2002-08-06 | Cognis Deutschland And Gmbh | Method for producing alkoxylated dimer fatty acids |
US6498268B1 (en) | 1997-08-25 | 2002-12-24 | Cognis Deutschland Gmbh | Method for producing alkylene glycol esters with limited homologue distribution |
US6534453B2 (en) | 2001-05-11 | 2003-03-18 | Exxonmobil Research And Engineering Company | Light oil composition |
US6743266B2 (en) | 2000-03-31 | 2004-06-01 | Texaco, Inc. | Fuel additive composition for improving delivery of friction modifier |
US6835217B1 (en) | 2000-09-20 | 2004-12-28 | Texaco, Inc. | Fuel composition containing friction modifier |
BG64828B1 (bg) * | 2001-04-04 | 2006-05-31 | "Векта" Оод | Метод за получаване на горивна смес от дизелово гориво |
EP0807155B2 (fr) † | 1995-02-02 | 2006-08-30 | ExxonMobil Chemical Patents Inc. | Compositions d'additifs de fuel oil |
WO2015059063A3 (fr) * | 2013-10-24 | 2015-08-13 | Basf Se | Utilisation d'un ester complexe pour réduire la consommation de carburant |
US9951288B2 (en) | 2013-10-24 | 2018-04-24 | Basf Se | Use of an alkoxylated polytetrahydrofuran to reduce fuel consumption |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1060877A (fr) * | 1952-05-14 | 1954-04-07 | Standard Oil Dev Co | Composition de fuel oil |
FR1405551A (fr) * | 1963-07-16 | 1965-07-09 | Exxon Research Engineering Co | Additifs anti-usure destinés à améliorer l'onctuosité d'hydrocarbures liquides |
US3900297A (en) * | 1971-06-07 | 1975-08-19 | James Michaels | Fuel for engines |
FR2272162A1 (fr) * | 1974-05-22 | 1975-12-19 | Autol Ag | |
EP0012292A1 (fr) * | 1978-12-16 | 1980-06-25 | Bayer Ag | Carburants et huiles combustibles, procédé pour leur préparation et leur utilisation |
FR2520376A1 (fr) * | 1982-01-22 | 1983-07-29 | Barclay John Rawson | Additif pour carburants et combustibles liquides hydrocarbones |
EP0227218A1 (fr) * | 1985-12-23 | 1987-07-01 | Exxon Research And Engineering Company | Méthodes d'amélioration de l'économie de fuel dans un moteur à combustion interne |
US4920691A (en) * | 1989-05-22 | 1990-05-01 | Fainman Morton Z | Fuel additive |
-
1994
- 1994-01-21 EP EP94300481A patent/EP0608149A1/fr not_active Withdrawn
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1060877A (fr) * | 1952-05-14 | 1954-04-07 | Standard Oil Dev Co | Composition de fuel oil |
FR1405551A (fr) * | 1963-07-16 | 1965-07-09 | Exxon Research Engineering Co | Additifs anti-usure destinés à améliorer l'onctuosité d'hydrocarbures liquides |
US3900297A (en) * | 1971-06-07 | 1975-08-19 | James Michaels | Fuel for engines |
FR2272162A1 (fr) * | 1974-05-22 | 1975-12-19 | Autol Ag | |
EP0012292A1 (fr) * | 1978-12-16 | 1980-06-25 | Bayer Ag | Carburants et huiles combustibles, procédé pour leur préparation et leur utilisation |
FR2520376A1 (fr) * | 1982-01-22 | 1983-07-29 | Barclay John Rawson | Additif pour carburants et combustibles liquides hydrocarbones |
EP0227218A1 (fr) * | 1985-12-23 | 1987-07-01 | Exxon Research And Engineering Company | Méthodes d'amélioration de l'économie de fuel dans un moteur à combustion interne |
US4920691A (en) * | 1989-05-22 | 1990-05-01 | Fainman Morton Z | Fuel additive |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0807155B2 (fr) † | 1995-02-02 | 2006-08-30 | ExxonMobil Chemical Patents Inc. | Compositions d'additifs de fuel oil |
US5855628A (en) * | 1995-04-24 | 1999-01-05 | Kao Corporation | Gas oil compositions and gas oil additives |
US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
US5632785A (en) * | 1995-12-01 | 1997-05-27 | Exxon Research & Engineering Company | Fuel economy additives |
US5993498A (en) * | 1996-09-13 | 1999-11-30 | Exxon Research And Engineering Co. | Polyol ester distillate fuels additive |
US6001141A (en) * | 1996-11-12 | 1999-12-14 | Ethyl Petroleum Additives, Ltd. | Fuel additive |
US6498268B1 (en) | 1997-08-25 | 2002-12-24 | Cognis Deutschland Gmbh | Method for producing alkylene glycol esters with limited homologue distribution |
US6429324B1 (en) | 1997-12-13 | 2002-08-06 | Cognis Deutschland And Gmbh | Method for producing alkoxylated dimer fatty acids |
US5891203A (en) * | 1998-01-20 | 1999-04-06 | Ethyl Corporation | Fuel lubricity from blends of a diethanolamine derivative and biodiesel |
US6743266B2 (en) | 2000-03-31 | 2004-06-01 | Texaco, Inc. | Fuel additive composition for improving delivery of friction modifier |
US6835217B1 (en) | 2000-09-20 | 2004-12-28 | Texaco, Inc. | Fuel composition containing friction modifier |
BG64828B1 (bg) * | 2001-04-04 | 2006-05-31 | "Векта" Оод | Метод за получаване на горивна смес от дизелово гориво |
US6534453B2 (en) | 2001-05-11 | 2003-03-18 | Exxonmobil Research And Engineering Company | Light oil composition |
WO2015059063A3 (fr) * | 2013-10-24 | 2015-08-13 | Basf Se | Utilisation d'un ester complexe pour réduire la consommation de carburant |
US9951288B2 (en) | 2013-10-24 | 2018-04-24 | Basf Se | Use of an alkoxylated polytetrahydrofuran to reduce fuel consumption |
US10030206B2 (en) | 2013-10-24 | 2018-07-24 | Basf Se | Use of a complex ester to reduce fuel consumption |
RU2673817C2 (ru) * | 2013-10-24 | 2018-11-30 | Басф Се | Использование смешанного сложного эфира для снижения расхода топлива |
US10465138B2 (en) | 2013-10-24 | 2019-11-05 | Basf Se | Use of a complex ester to reduce fuel consumption |
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Legal Events
Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 19940208 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: CAPROTTI, RINALDO Inventor name: BOVINGTON, CHARLES HERBERT |
|
17Q | First examination report despatched |
Effective date: 19961023 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
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18D | Application deemed to be withdrawn |
Effective date: 19970506 |