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WO2007070360A2 - Compositions favorisant l’onctuosite et procedes d’amelioration de l’onctuosite de combustibles hydrocarbones - Google Patents

Compositions favorisant l’onctuosite et procedes d’amelioration de l’onctuosite de combustibles hydrocarbones Download PDF

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Publication number
WO2007070360A2
WO2007070360A2 PCT/US2006/046804 US2006046804W WO2007070360A2 WO 2007070360 A2 WO2007070360 A2 WO 2007070360A2 US 2006046804 W US2006046804 W US 2006046804W WO 2007070360 A2 WO2007070360 A2 WO 2007070360A2
Authority
WO
WIPO (PCT)
Prior art keywords
polyalkenylsuccinimide
lubricity
fuel additive
lubricity enhancing
enhancing fuel
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.)
Ceased
Application number
PCT/US2006/046804
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English (en)
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WO2007070360A3 (fr
Inventor
Jr. C. Edward Baxter
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Envirofuels LLC
Original Assignee
Envirofuels LLC
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 Envirofuels LLC filed Critical Envirofuels LLC
Publication of WO2007070360A2 publication Critical patent/WO2007070360A2/fr
Publication of WO2007070360A3 publication Critical patent/WO2007070360A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 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
    • C10L1/22—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 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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine

Definitions

  • the present invention relates to additive compositions for enhancing the lubricity of hydrocarbon fuels in which the natural lubricity has been diminished due to treatment of the fuel to reduce sulfur and aromatic components for improved emissions.
  • Hydrocarbon distillates and residuals used as fuel can typically contain up to 5,000 ppm sulfur.
  • the sulfur oxidizes during the combustion process to form SO 2 and SO 3 which, in addition to be emitted as acid gas, can also form sulfates.
  • the sulfates then become part of the diesel engines particulate emissions. Therefore, reducing sulfur can reduce particulate emissions.
  • Sulfur reductions in fuel have been mandated in many parts of the world including the U.S. and in the European Union. The result will be sulfur levels phased down to less than 15 ppm with eventual reductions to less than 5 ppm.
  • lubricity improver additives to impart acceptable lubricating properties back to the fuel.
  • Various injector and injector pump tests and several laboratory tests have been developed to measure the lubricity of diesel fuels.
  • ASTM D 6079 High Frequency Reciprocating Rig (“HFRR”) test is the most widely used and accepted.
  • Esters of long chain fatty acids have »also been disclosed as fuel lubricity additives.
  • the acid group of these molecules has been blocked by the esterification reaction and, thus, is not available for interaction with the other fuel and lubricant additives.
  • the lubricity imparting function of the fatty acid has been reduced.
  • Amides of long chain fatty acids disclosed as fuel lubricity additives have the advantage of reduced affinity to react with other fuel and lubricant additives but, like the esterification reaction described above, amination can also result in loss or reduction of the lubricity function of the fatty acid.
  • Esters and amides of fatty acids are disclosed in U.S. Patent Nos. 3,273,981 (to Furey) 4,204,481 (to Malec), 4,729,769 (to Schlicht, et al.).
  • Alkoxyamides are disclosed in U.S. Patent No. 4,427,562 (to Horodysky, et al.).
  • U.S. Patent 6,296,677 (to Ribeaud, et al.) describes the reaction of various oils with active hydrogen compounds and carboxylic acids. These compounds are claimed to reduce wear in the fuel system of diesel engines operating on fuels with reduced sulfur and aromatic content.
  • U.S. Patent No. 6,793,696 (to Krull, et al.) discloses low sulfur diesel fuel oil compositions containing salts of fatty acids with short chain oil soluble amines.
  • 6,835,217 discloses fuel compositions comprising a major amount of hydrocarbon fuel containing at least one alcohol and substantially free from MTBE, and a friction modifying amount of a friction reducing agent prepared by the reaction of at least one natural or synthetic oil with at least one alkanolamine.
  • U.S. Patent No. 6,872,230 discloses reaction products of alkylated polyarnines with various ureas or isocyanates and derivatives thereof.
  • polyalkenylsuccinimides Another group of compounds used in lubricating oils are polyalkenylsuccinimides.
  • Polyalkenylsuccinimides are well known and are used extensively as dispersants in lubricating oils. These dispersants function by surfactant action to hold polar dirt and sludge compounds into the oil matrix so they can be removed by filtration.
  • the polyalkenylsuccinimide dispersants have a relatively high molecular weight hydrocarbon tail to provide oil solubility. The molecular weight is generally in the range from about 1 ,000 to 2,000 daltons.
  • polyalkyleneamines Another class of compounds commonly known as polyalkyleneamines function very well as fuel detergents and are effective at cleaning intake valve deposits ("IVD") without contributing to combustion chamber deposits (“CCD”). Thus, polyalkyleneamines generally are utilized as fuel additives.
  • low molecular weight polyalkenylsuccinimides and derivatives i.e., having molecular weights lower than 1,000 daltons but usually 350-750 daltons are used in fuel as stabilizers because the higher nitrogen content prevents fuel degradation during storage. These low molecular weight polyalkenylsuccinimides do not provide any lubricity enhancement of fuels.
  • lubricity enhancing fuel additive or process for forming lubricity enhancing fuel additives that: provide reduction in sulfur emissions; provide increased lubricity of fuels, and in particular, diesel fuels; and include a high molecular weight polyalkenylsuccinimide. Therefore, the art has sought lubricity enhancing fuel additives and processes for forming lubricity enhancing fuel additives that: provide reduction in sulfur emissions; provide increased lubricity of fuels, and in particular, diesel fuels; and include a high molecular weight polyalkenylsuccinimide.
  • a lubricity enhancing fuel additive is needed that removes one or more of the negative characteristics associated with current fuel lubricity technologies.
  • the lubricity enhancing fuel additives disclosed herein advantageously resist the process of readily hydrolyzing or degrading to species that can interact with the other additives, used in either the fuel or engine lubricant, and furthermore advantageously resist contributing to undesirable emissions or generation of undesirable emissions and therefore should advantageously be low in sulfur and low in aromatic content and not contain heavy metals.
  • lubricity enhancing fuel additives comprising a polyalkenylsuccinimide of higher molecular weights improve the lubricity of fuels.
  • Such polyalkenylsucinimides are not typically used in fuel.
  • a low aromatic paraffinic base oil and a low aromatic petroleum distillate are included with the polyalkenylsuccinimide of the lubricity enhancing fuel additives to improve lubricity of hydrocarbon fuels.
  • the polyalkenylsuccinim.de component preferably is a mixture of a mono- polyalkenylsuceinimide and a di-polyalkenylsuccin ⁇ mide.
  • composition of the current invention can be added to fuels of poor lubricity, such as middle distillate fuels that have been treated to reduce sulfur and aromatics including, gasoline, diesel fuel, kerosene, fuel oils and heavy fuel oils.
  • This new invention also comprises methods of increasing fuel lubricity by treatment of the fuel with die lubricity enhancing fuel additives disclosed herein.
  • the fuel may contain, in addition to the lubricity enhancing fuel additives disclosed herein, other additives commonly added as minor constituents to the fuel such as cold flow improvers, antifoam additives, cetane improvers, combustion improvers and the like. These other components can be added individually or as part of a complete multifunctional package.
  • a lubricity enhancing fuel additive comprising a polyalkenylsuceinimide having a molecular weight greater than 2,000 daltons wherein the lubricity enhancing fuel additive increases the lubricity of a hydrocarbon fuel by at least i0 percent using the High Frequency Rotating Rig test described in ASTM D 6079.
  • a further feature of the lubricity enhancing fuel additive is that the polyalkenylsuceinimide can comprise a mono-polyalkenylsuccinimide.
  • Another feature of the lubricity enhancing fuel additive is that the polyalkenylsuceinimide can comprise a di- polyalkenylsuccinimide.
  • An additional feature of the lubricity enhancing fuel additive is that the polyalkenyl ⁇ uccinimide can comprise a mono-polyalkenylsuccinimide and a di- polyalkenylsuccinimide.
  • the mono-polyalk ⁇ nylsuccinimide and the di-polyalkenylsuccinimide can be present in a ratio of 3 to 1.
  • a further feature of the lubricity enhancing fuel additive is that the mono- polyalkenylsuccinimide and the di-polyalkenylsuccinimide can be present in a ratio of 1 to 3.
  • Another feature of the lubricity enhancing fuel additive is that the mono- polyalkenylsuccinimide and the di-polyalkenylsuccinimide can be present in a ratio of 1 to 1.
  • the lubricity enhancing fuel additive can further comprise a low aromatic paraffinic base oil having a molecular weight in the range from 250 to 650 daltons and preferably in the range from 350 to 450 daltons. Further, aromatic portion of the paraffinic base oil is preferably less than 5% and more preferably less than 1%. Still another feature of the lubricity enhancing fuel additive is that the weight proportion of the low aromatic paraffinic base oil can be in the range from 50 to 90 weight percent of the lubricity enhancing fuel additive. A further feature of the lubricity enhancing fuel additive is that the weight proportion of the low aromatic paraffinic base oil can be in the range from.
  • the lubricity enhancing fuel additive can further comprise a low aromatic petroleum distillate having a molecular weight in the range from 250 to 650 daltons and preferably in the range from 350 to 450 daltons. Further, aromatic portion of the petroleum distillate is preferably less than 5% and more preferably less than 1%.
  • the weight proportion of the low aromatic petroleum distillate can be in the range from 5 to 50 weight percent of the lubricity enhancing fuel additive.
  • the weight proportion of the low aromatic petroleum distillate can be in the range from 15 to 40 weight percent of the lubricity enhancing fuel additive.
  • the weight proportion of the low aromatic petroleum distillate can be in the range from 20 to 25 weight percent of the lubricity enhancing fuel additive.
  • one or more of the foregoing advantages can also be achieved through a process for forming a lubricity enhancing fuel additive.
  • the process can comprise the steps of: forming a first polyalkenylsuccinimide having a molecular weight greater than 2,000 daltons and combining at room temperature the first polyalkenylsuccinimide with a low aromatic parraff ⁇ nic base oil and a low aromatic petroleum distillate to form the lubricity enhancing fuel additive, wherein the low aromatic parraffinic base oil is present in the lubricity enhancing fuel additive in a range from 50 to 90 weight percent and the low aromatic petroleum distillate is present in the lubricity enhancing fuel additive in a range from 5 to 50 weight percent, wherein the lubricity of the fuel is increased at least 10 percent using the High Frequency Rotating Rig test described in ASTM D 6079.
  • a further feature of the process for forming an lubricity enhancing fuel additive is that a second polyalkenylsuccinimide can be combined with the first polyalkenylsuccinimide, the low aromatic parraffinic base oil, and the low aromatic petroleum distillate to form the lubricity enhancing fuel additive.
  • Another feature of the process for forming an lubricity enhancing fuel additive is that the first polyalkenylsuccinimide and the second polyalkenylsuccinimide can be combined in a ratio of 3 to 1.
  • An additional feature of the process for forming an lubricity enhancing fuel additive is that the first polyalkenylsuccinimide and the second polyalkenylsuccinimide can be combined in a ratio of 1 to 3.
  • Still another feature of the process for forming an lubricity enhancing fuel additive is that the first polyalkenylsuccinimide and the second polyalkenylsuccinimide can be combined in a ratio of 1 to 1.
  • a further feature of the process for forming an lubricity enhancing fuel additive is that the first polyalkenylsuccinimide can comprise a mono- polyalkenylsuccinimide and the second polyalkenylsuccinimide can comprise a di- polyalkenylsuccinimide.
  • the lubricity enhancing fuel additive contains only a polyalkenylsuccinimide, a low aromatic paraffinic base oil, and a low aromatic petroleum distillate.
  • the lubricity enhancing fuel additive includes a polyalkenylsuccinimide, a low aromatic paraffmic base oil, and a low aromatic petroltjum distillate, a dispersant, a solvent, and other non-functional elements from the formation of the polyalkenylsuccinimide.
  • the polyalkenylsuccinimide can include one or both of mono-polyalkenylsuccinimide or di- polyalkenylsuccmimide.
  • the lubricity enhancing fuel additives and processes for forming lubricity enhancing fuel additives have the advantages of: providing reduction in sulfur emissions; providing an increase in the lubricity of fuels, and in particular, diesel fuels; and including a high molecular weight polyalkenylsuccinimide.
  • Fuels may be treated with the composition of the current invention at weight proportions of 1 to 10,000 ppm, preferably between 5 and 5,000 ppm and most preferably between 800 and 1 ,600 ppm to impart improved lubricity characteristics to the fuel.
  • the mono-polyalkenylsuccinimide can be represented by the general structure (I):
  • R is a polyisobutenyl group and may be from 150 to 3,000 molecular weight, preferably from 500 to 1,200 molecular weight and most preferably from 800 to 1,200 molecular weight
  • y can be an integer from 0 to 10 and preferably from 2-10 and most preferably from 2-5.
  • the di-polyalkenylsuccinimide can be represented by the general structure (II): where R is a polyisobutenyl group and may be from 300 to 3,000 molecular weight, preferably from 1,200 to 2,800 molecular weight and most preferably from 2,200 to 2,800 molecular weight; y can be an integer from 0 to 10 and preferably from 2-10 and most preferably from 2-5.
  • the weight ratio of polyalke ⁇ ylsuccinirnide of structure I to structure II can range from 99:1 to 1:99, preferably from 75:25 to 25:75 and most preferably 50:50.
  • the weigjit proportion of the low aromatic paraffinic base oil can range from 50 to 90%, preferably from 50 to 85%, and most preferably from 60 to 80%.
  • the weight proportion of the low aromatic petroleum distillate can range from 5 to 50%, preferably from 15 to 40% and most preferably from 20 to 25%.
  • the weight proportion the polyalkenylsuccinimide of Structure I and Structure II combined can range from 1 to 10%, preferably from 2 to 8% and most preferably from 4 to 8%.
  • the total base number is a specification and is preferably at least 1 mg KOH/gram and most preferably greater than 3 mg KOH/gram.
  • the low aromatic paraffinic base oil can be an API Group II, III or IV base oil or white oil or mixtures thereof.
  • the aromatic content can be less than 5 ppm, preferably less than 2 ppm and most preferably less than 1 ppm.
  • the paraffinic content can be greater than 80%, more preferably greater than 85% and most preferably greater than 90%.
  • the sulfur content may be less than 300 ppm, preferably less than 200 ppm and most preferably less than 100 ppm.
  • the low aromatic light petroleum distillate may have a boiling point of less than 300 0 C, preferably less 250 0 C and most preferably less than 225 0 C and a flash point greater than 50 0 C, preferably greater than 55 0 C and most preferably greater than 60 0 C.
  • the aromatic content may be less 5 ppm, preferably less than 2 ppm and most preferably less than 1 ppm.
  • the sulfur content may be less 5 ppm, preferably less than 2 ppm and most preferably less than 1 ppm.
  • a reaction mixture containing 98 grams (1.0 mole) of maleic anhydride and 950 grams (1.0 mole) of TPC 595 (highly reactive polyisobutylene of 950 molecular weight, available from Texas Petrochemicals) was heated at 240 0 C for 6 to S hours. The mixture was then vacuum stripped to remove un-reacted maleic anhydride and cooled to less than 80 0 C.
  • This intermediate polyalkylenesuccinic anhydride (“PIBSA”) was light yellow in color, free of char with a saponification number of 118 and a residual maleic anhydride content of less 0.1%.
  • the PIBSA was mixed with 100 milliliters of toluene.
  • TEPA triethylenepentamine
  • PIBSI polyalkenylsuccinimide
  • Example II Di-Polyalkenylsuccinimide (II)
  • TPC 5230 highly reactive polyisobutylene of 2,300 molecular weight, available from Texas Petrochemicals
  • 98 grams (1.0 mole) of maleie anhydride was reacted at 240 0 C for 4 hours and the reaction continued at 260 0 C for an additional 4 hours.
  • the PIBSA intermediate was dark yellow in color and had a saponification number of 77 and a residual maleie anhydride content of less than 0.1%.
  • PIBSI polyalkenylsuccinimide
  • a composition capable of imparting lubricity to fuels was prepared by mixing 244 grams of Motiva Star 4 base oil, 78 grams of Ashland Solvent 142, 10 grams of mono- polyalkenylsuccinimide from Example I and 10 grams of di-polyalkenylsuccinimide from Example II. The mixture was stirred at room temperature (19-25°C) until a clear light yellow solution with a nitrogen value of 870 ppm was obtained. The TBN was 3.45. Improvement of Fuel Lubricity
  • HFRR High Frequency Rotating Rig
  • the fuel lubricity composition of the current invention reduced the wear scar by 18 %, clearly demonstrating a substantial improvement in fuel lubricity.

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

Abstract

L’invention concerne des compositions d’additif pour combustibles destinées à améliorer l’onctuosité de combustibles hydrocarbonés dont l’onctuosité naturelle a été diminuée par des traitements du combustible afin de réduire la teneur en composés soufrés et aromatiques dans le but d’améliorer les émissions. Les compositions d’additif pour combustibles comprennent de préférence (1) un polyalcénylsuccinimide de masse moléculaire élevée ; (2) une huile de base paraffinique aromatique de faible masse moléculaire ; et (3) un distillat de pétrole aromatique de faible masse moléculaire destinés à conférer une onctuosité améliorée aux combustibles hydrocarbonés.
PCT/US2006/046804 2005-12-09 2006-12-08 Compositions favorisant l’onctuosite et procedes d’amelioration de l’onctuosite de combustibles hydrocarbones Ceased WO2007070360A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74923105P 2005-12-09 2005-12-09
US60/749,231 2005-12-09

Publications (2)

Publication Number Publication Date
WO2007070360A2 true WO2007070360A2 (fr) 2007-06-21
WO2007070360A3 WO2007070360A3 (fr) 2007-08-02

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PCT/US2006/046804 Ceased WO2007070360A2 (fr) 2005-12-09 2006-12-08 Compositions favorisant l’onctuosite et procedes d’amelioration de l’onctuosite de combustibles hydrocarbones

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AR (1) AR058299A1 (fr)
PE (1) PE20070926A1 (fr)
UY (1) UY29994A1 (fr)
WO (1) WO2007070360A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1970430A3 (fr) * 2007-03-09 2009-10-21 Afton Chemical Corporation Composition de carburant contenant un succinimide substitué d'hydrocarbyle
US8690968B2 (en) 2008-04-04 2014-04-08 Afton Chemical Corporation Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine
CN104838255A (zh) * 2012-11-15 2015-08-12 弗兰霍菲尔运输应用研究公司 碳纤维材料纤维方向的测量和对象碳纤维复合结构方式的制造

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ231731A (en) * 1988-12-30 1991-03-26 Mobil Oil Corp Additive for fuels of internal combustion engines comprising a polyalkylene succinimide
GB9502041D0 (en) * 1995-02-02 1995-03-22 Exxon Chemical Patents Inc Additives and fuel oil compositions
JP2001316361A (ja) * 2000-05-01 2001-11-13 Ethyl Corp スクシンイミド−酸化合物およびそれの誘導体
GB0204241D0 (en) * 2002-02-22 2002-04-10 Ass Octel Compound

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1970430A3 (fr) * 2007-03-09 2009-10-21 Afton Chemical Corporation Composition de carburant contenant un succinimide substitué d'hydrocarbyle
US9011556B2 (en) 2007-03-09 2015-04-21 Afton Chemical Corporation Fuel composition containing a hydrocarbyl-substituted succinimide
US8690968B2 (en) 2008-04-04 2014-04-08 Afton Chemical Corporation Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine
CN104838255A (zh) * 2012-11-15 2015-08-12 弗兰霍菲尔运输应用研究公司 碳纤维材料纤维方向的测量和对象碳纤维复合结构方式的制造

Also Published As

Publication number Publication date
PE20070926A1 (es) 2007-09-24
WO2007070360A3 (fr) 2007-08-02
AR058299A1 (es) 2008-01-30
UY29994A1 (es) 2007-07-31

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