EP2611892A2 - Funktionalisierte maleinierte fettsäuren als nichtsaure fluidzusatzstoffe - Google Patents

Funktionalisierte maleinierte fettsäuren als nichtsaure fluidzusatzstoffe

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Publication number
EP2611892A2
EP2611892A2 EP11822341.1A EP11822341A EP2611892A2 EP 2611892 A2 EP2611892 A2 EP 2611892A2 EP 11822341 A EP11822341 A EP 11822341A EP 2611892 A2 EP2611892 A2 EP 2611892A2
Authority
EP
European Patent Office
Prior art keywords
fatty acid
group
acid
unsaturated
mixtures
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Withdrawn
Application number
EP11822341.1A
Other languages
English (en)
French (fr)
Inventor
Jianzhong Yang
Paul J. Biggerstaff
Jerry J. Weers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Baker Hughes Holdings LLC
Original Assignee
Baker Hughes Inc
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 Baker Hughes Inc filed Critical Baker Hughes Inc
Publication of EP2611892A2 publication Critical patent/EP2611892A2/de
Withdrawn legal-status Critical Current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
    • 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
    • C10L1/18—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 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
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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
    • C10L1/222—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 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
    • C10L10/04—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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/72—Esters of polycarboxylic acids
    • 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
    • C10M133/16—Amides; Imides
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free 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
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
    • 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
    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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

Definitions

  • the present invention relates to methods and compositions for improving the properties of various fluids, and more particularly relates, in one non-limiting embodiment, to methods and compositions for hydrocarbon fuel lubricity additives made from maleic anhydride and fatty acids.
  • the fatty acids, fatty acid ammonium salts and fatty acid amides either have to be greatly diluted or kept in heated storage vessels and added via heated pipework.
  • a method of improving the lubricity of a hydrocarbon fuel involves adding to the hydrocarbon fuel an effective amount of functionalized maleated fatty acid that is an ester, imide and/or amide to improve the lubricity thereof.
  • the functionalized maleated fatty acid is made by a process including reacting an unsaturated fatty acid with an unsaturated compound selected from the group consisting of an unsaturated anhydride, a maleimide, and mixtures thereof.
  • the unsaturated compound may be substituted with a linear or branched alkyl group. This first step gives a maleated fatty acid.
  • the maleated fatty acid is reacted with a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof.
  • a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof.
  • the functionalized maleated fatty acid may optionally have one of the structures (I) through (IX) shown below.
  • the functional- ized maleated fatty acid may also improve the lubricity of a lubricant, e.g. a motor oil; a transmission fluid, e.g. in an automotive automatic transmission, and in an alcohol, e.g. in methanol and/or ethanol when used as a fuel. Further, it is expected that the functionalized maleated fatty acid may also reduce the corrosivity of these fluids with respect to metals that they come into contact with, as well as to reduce the corrosivity of hydrocarbon fuels.
  • a lubricant e.g. a motor oil
  • a transmission fluid e.g. in an automotive automatic transmission
  • an alcohol e.g. in methanol and/or ethanol
  • functionalized maleated fatty acids which may be esters, imides and/or amides, may improve the properties of certain fluids; for instance they may improve the lubricity and the corrosivity of fuels and lubricants, such as hydrocarbon and/or alcohol fuels and lubricants.
  • Maleated fatty acids are produced through the reaction of unsaturated fatty acids, such as oleic acid or linoleic acid with maleic anhydride.
  • the resulting maleated fatty acids may be further functionalized with a polyol, e.g. ethylene glycol, glycerol and the like, to make a non-acidic triester; with an alkanolamine to make an imide/amide hybrid; and with an alkanolamine and polyols to make an imide/ester hybrid.
  • the triester, or amide/ester hybrid are more readily made by alkoxylation with alkanolamine, ethylene oxide (EO) and/or propylene oxide (PO).
  • the functionalized maleated fatty acid may have a structure of a formula selected from the group (I) through (IX) consisting of:
  • R 2 is a direct bond or hydrocarbyl group having 1 to 1 0 carbons with one or more double bonds
  • R 3 is - (CH 2 CH 2 0) n -, or -(CH 2 CH(CH 3 )0) n -, or combinations thereof,
  • R 4 is -(CH 2 CH 2 0) n H, -(CH 2 CH(CH 3 )0) n H, -CH 2 CHOHCH 2 OH, or
  • n is an integer from 1 to 1 0, alternatively from 1 to 5.
  • the functionalized maleated fatty acids herein in one useful, non- limiting embodiment may be essentially non-acidic, due to all of the carboxylic acid groups being reacted or functionalized, with a multifunctional reactant.
  • the acid number of the functionalized maleated fatty acids is less than 1 0, in another non-limiting embodiment the acid number is less than 5; alternatively it is less than 3. Because these materials are essentially non-acidic or have very low acidity, their ability to contribute to deposit formation tendency of the fluid (e.g. fuel) to which they are added is greatly reduced, and as noted, in some contexts may serve as corrosion inhibitors.
  • the unsaturated fatty acid used to make the additives described herein may have a weight average molecular weight between about 300 to about 5000 and may be selected from the group consisting of monomeric, dimeric, trimeric crosslinked unsaturated fatty acids, unsaturated fatty acids having from 2 to 30 carbon atoms and mixtures thereof. Specific examples include, but are not necessarily limited to oleic acid, linoleic acid, a-linolenic acid, C1 0 to C40 unsaturated synthetic dimer fatty acids, unsaturated fatty acids having from 2 to 30 carbon atoms, such as those obtained from the olefin metathesis of fatty acids, arachidonic acid, and mixtures thereof.
  • the unsaturated compound that is initially reacted with the unsaturated fatty acid is an unsaturated anhydride, such as maleic anhydride or phthalic anhydride; a maleimide, such as maleimide itself or other maleimide, or mixtures thereof.
  • unsaturated anhydride such as maleic anhydride or phthalic anhydride
  • maleimide such as maleimide itself or other maleimide, or mixtures thereof.
  • reactants may be substituted with a linear or branched alkyl group, in one embodiment a lower alkyl group, which is defined herein as having from 1 to 4 carbon atoms.
  • the molar ratio of unsaturated fatty acid to unsaturated compound ranges from about 1 :50 independently to about 50: 1 in one non-limiting embodiment, in another aspect from about 1 :1 0 independently to about 10:1 , alternatively from about 1 :2 independently to about 2:1 or in another non-restrictive version from about 1 .1 :1 independently to about 1 :1 .1 or equimolar.
  • independently it is meant than any of the lower thresholds may be combined with any of the upper thresholds.
  • the multifunctional reactants that are reacted with the maleated fatty acid include, but are not necessarily limited to, polyols, alkanolamines, alkylene oxides and mixtures thereof.
  • Suitable polyols include, but are not necessarily limited to glycol, e.g. ethylene glycol and other glycols for instance propylene glycol; glycerol; alkyl phenols; alkyoxylated alkyl phenol; linear or branched alkyl alcohols; each of which may have from 2 to 30 carbon atoms and mixtures thereof.
  • Suitable alkanolamines include, but are not necessarily limited to, ethanolamine, propanolamine, diethanolamine, n-alkylethanolamine, isopropanol amine, diisopropanol amine, 3-amino-1 ,2-propanediol and mixtures thereof.
  • Suitable alkylene oxides include, but are not necessarily limited to, ethylene oxide, propylene oxide, butylene oxide and mixtures thereof.
  • the molar ratio of maleated fatty acid to multifunctional reactant ranges from about 1 :20 to about 20:1 may range from about 1 :20 independently to about 20:1 ; alternatively from about 10:1 independently to about 1 :10.
  • the reactions to make the functionalized maleated fatty acids proceed well without special considerations and are known to those skilled in the art. In general, they may proceed at a temperature range between about 160 to about 260 °C and a pressure range between about 1 to about 10 atm (0.1 to 1 MPa) in the presence of common phenol based antioxidants such as 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, 2,5-di-tert-butylhydro- quinone, polyisobutylene phenol, tocopherol (Vitamin E family) and the like and mixtures thereof.
  • Lewis acid catalysts may be used to improve the reaction rate, but no catalysts are generally used.
  • distillate fuels include, but are not necessarily limited to diesel fuel, kerosene, gasoline middle distillate fuel, and the like. They may also be used in heavy fuel oil. It will be appreciated that distillate fuels include blends of conventional hydrocarbons meant by these terms with oxygenates, e.g. alcohols, such as methanol, ethanol, and other additives or blending components presently used in these distillate fuels, or that may be used in the future.
  • oxygenates e.g. alcohols, such as methanol, ethanol, and other additives or blending components presently used in these distillate fuels, or that may be used in the future.
  • the methods and compositions herein relate to low sulfur fuels, which are defined as having a sulfur content of 0.2% by weight or less, and in another non-limiting embodiment as having a sulfur content of about 0.0015 wt.% or less - such as the so-called "ultra low sulfur" fuels.
  • hydrocarbon fuels herein include, but are not necessarily limited to, diesel and kerosene, and in one non-restrictive version, ultra low sulfur diesel (ULSD) fuels. However, they also may be used for fuels having sulfur contents higher than this.
  • ULSD ultra low sulfur diesel
  • the functionalized maleated fatty acids described herein may also be used as corrosivity improvers for the fuels described above, for instance when these fuels come into contact with metal, particularly, but not limited to, iron alloys, particularly the various commonly used steel alloys.
  • the functionalized maleated fatty acids may function as corrosion inhibitors or lubricity enhancers in other fluids including, but not necessarily limited to, lubricants, such as motor oil, transmission fluids, cutting fluids, and the like.
  • the lubricity additive in the total fuel should at least be an amount to improve the lubricity of the fuel as compared to an identical fuel absent the additive.
  • the amount of additive may range from about 25 independently to about 3000 ppm, and in an alternate embodiment, the lower threshold may be about 25 ppm and the upper threshold may independently be about 200 ppm and in one non-limiting embodiment from about 50 independently to about 150 ppm.
  • the amount of additive should be that effective to reduce the corrosivity of the fluid as compared to an identical fuel absent the additive. In one non-limiting embodiment, the amount may range from about 1 independently to about 1 00 ppm, alternatively from about 1 independently to about 1 0 ppm.
  • optional components may be added independently to the fluids being treated.
  • these may include, but are not necessarily limited to, detergents, pour point depressants, cetane improvers, dehazers, cold operability additives (e.g. cold flow improvers), conductivity improvers, other corrosion inhibitors, stability additives, demulsifiers, biocides, dyes, and mixtures thereof.
  • water is explicitly absent from the inventive composition.
  • maleated fatty acid In a typical reaction, oleic acid (1 00 g) and maleic anhydride (25 g) were charged into a 250 ml 3-neck flask under nitrogen. The mixture was heated sequentially up to 240 °C for 30 hrs until the reaction was completed. The reaction was monitored by FT- infrared spectroscopy (FT-I R) as is known to those skilled in the art. The final product was diluted by aromatic solvent to a concentration of 90% active and marked as Example 1 .
  • FT-I R FT- infrared spectroscopy
  • Example 1 material Above is a representative structure of Example 1 material.
  • Oleic acid (100.1 g) and maleic anhydride (25.3 g) were mixed in a 3-neck flask. The mixture was heated sequentially up to 240 °C until the reaction is completed as monitored by FT-I R. The reaction mixture was first cooled to room temperature, and then ethanolamine (38.0 g) was added drop- wise while stirring. After the addition was completed, the reaction temperature was first set at 80 °C, and then raised to 180 °C sequentially in 2 hours. The reaction process was monitored by FT-IR and acid number analysis. A second batch of ethanolamine (6.0 g) was added after 8 hrs reaction time. The reaction was stopped when the acid number is below 3. The final product was diluted with aromatic solvent to a concentration of 80% active and marked as Example 2.
  • Linoleic and oleic acid mixture (100.0 g) and maleic anhydride (25.0 g) were mixed in a 3-neck flask. The mixture was heated sequentially up to 240 °C until the reaction is completed as monitored by FT-IR. The reaction mixture was first cooled to room temperature, and then ethanolamine (15.6 g) was added dropwise while stirring. After the addition was completed, the reaction temperature was first set at 70 °C, and then raised to 1 20 °C sequentially in 4 hours. The reaction process was monitored by FT-I R. Ethylene glycol (22.1 g) was added after the amines are consumed. The temperature was raised to 185 °C and water was removed as a by-product via a Dean-Stark trap. After the acid number reached 20, a second batch of ethylene glycol (4.6 g) was added to drive the acid number further down. The reaction was stopped when the acid number was below 5. The final product was diluted with aromatic solvent to a concentration of 90% active and marked as Example 3.
  • Example 5 Above is a representative structure of Example 4.
  • Example 5
  • the present invention may suitably comprise, consist or consist essentially of the elements disclosed and may be practiced in the absence of an element not disclosed.
  • the method may consist essentially of or consist of reacting an unsaturated fatty acid with an unsaturated compound selected from the group consisting of an unsaturated anhydride, a maleimide, and mixtures thereof where the unsaturated compound may be substituted with a linear or branched alkyl group, which reacting gives a maleated fatty acid.
  • the method may optionally additionally consist essentially of or consist of reacting the maleated fatty acid with a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof to give a functionalized maleated fatty acid that has an acid number less than 10, where the reactants are as described in the claims.
  • a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof to give a functionalized maleated fatty acid that has an acid number less than 10, where the reactants are as described in the claims.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP11822341.1A 2010-09-01 2011-08-16 Funktionalisierte maleinierte fettsäuren als nichtsaure fluidzusatzstoffe Withdrawn EP2611892A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/873,475 US20120053101A1 (en) 2010-09-01 2010-09-01 Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives
PCT/US2011/047928 WO2012030524A2 (en) 2010-09-01 2011-08-16 Functionalized maleated fatty acids as non acidic fluid additives

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EP2611892A2 true EP2611892A2 (de) 2013-07-10

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US (1) US20120053101A1 (de)
EP (1) EP2611892A2 (de)
WO (1) WO2012030524A2 (de)

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CN103664841B (zh) * 2013-11-29 2015-07-08 山东艾孚特科技有限公司 一种马来酸酐接枝植物油酸的制备方法
US9663726B2 (en) * 2014-02-10 2017-05-30 Baker Hughes Incorporated Fluid compositions and methods for using cross-linked phenolic resins
EP3720920B1 (de) 2017-12-08 2024-01-24 Baker Hughes Holdings LLC Auf ionischer flüssigkeit basierende asphalteninhibitoren für bohrlöcher und verfahren zur verwendung davon
EA202091413A1 (ru) 2018-07-11 2020-09-24 Бейкер Хьюз Холдингз Ллк Скважинные ингибиторы асфальтенов на основе ионной жидкости и способы их применения
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