WO2013078631A1 - Agent anti-usure de combustible hydrocarboné et son procédé d'utilisation - Google Patents

Agent anti-usure de combustible hydrocarboné et son procédé d'utilisation Download PDF

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Publication number
WO2013078631A1
WO2013078631A1 PCT/CN2011/083194 CN2011083194W WO2013078631A1 WO 2013078631 A1 WO2013078631 A1 WO 2013078631A1 CN 2011083194 W CN2011083194 W CN 2011083194W WO 2013078631 A1 WO2013078631 A1 WO 2013078631A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
antiwear agent
chain fatty
short
acid amide
Prior art date
Application number
PCT/CN2011/083194
Other languages
English (en)
Chinese (zh)
Inventor
熊靓
Original Assignee
Xiong Liang
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 Xiong Liang filed Critical Xiong Liang
Priority to PCT/CN2011/083194 priority Critical patent/WO2013078631A1/fr
Priority to CN201180075206.5A priority patent/CN104024387A/zh
Publication of WO2013078631A1 publication Critical patent/WO2013078631A1/fr

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
    • C10L1/22—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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear

Definitions

  • Hydrocarbon fuel antiwear agent and using method thereof
  • the present invention relates to an antiwear agent suitable for use in a hydrocarbon fuel and a method of using the same, which is particularly suitable for use in gasoline and diesel for internal combustion engines, and can effectively improve stability and low temperature during storage of an antiwear agent.
  • Detergents have been widely used as additives in gasoline and diesel to prevent surface deposition of the oil system and improve the surface finish and service life of the engine, especially in low-sulfur fuels with poor lubricity, to improve the lubricity of the oil. Required, otherwise the service life of the grease pump will be greatly affected.
  • the removal of sulfur does not affect the lubricating properties of the fuel itself.
  • the lubricants naturally carried in the fuels such as aromatic organic compounds, carboxylic acids and lipids are also different. Removal of the degree.
  • US Pat. No. 4,729,769 describes a gasoline carburetor detergent used as a gasoline component, which is a fatty acid composed of 6-20 carbon atoms (such as coconut oil) and single or two.
  • ⁇ a product obtained by reacting a mono-, di-hydroxy hydrocarbyl amine, or a diethnol amine, but the gasoline added with the detergent needs to be added with an anti-icing agent when used in winter. .
  • Additives that add lubricity are various types of fatty acids, fatty esters, amine and amide organics, and mixtures thereof. As previously studied, it has been found that saturated, haplotype or diploid linear fatty acids containing from 12 to 54 carbon atoms can be used as additives to enhance the lubricating properties of hydrocarbon fuels.
  • linear fatty acids used as anti-wear agents or lubricant improvers are mostly natural products extracted from animals or plants, such as oleic acid, linoleic acid, stearic acid, tall. Tail oil fatty acid, linolenic acid, palmitic acid, coco fatty acid, and ricinoleic acid, but a few are synthetic products.
  • an anti-wear agent extracted from a fuel is disclosed in the international patent WO 01/72930 A2, which may also be combined with some polyetheramines (polyisobutene amines, Mannich bases and succinimides, etc.). use.
  • Fatty acid esters, unsaturated dimerization are mentioned in the references of the patents (US Pat No.
  • U.S. Patent No. 5,858,029 discloses an antiwear agent for fuels and lubricating oils comprising hydroxyamides which are the reaction products of primary etheramine and hydrocarboxylic acid.
  • the reported anti-wear agent active ingredients are fatty acid formamides (US Pat No 4,789,493, 4,808,196,4, 867,752), fatty acids.
  • Fatty acid amides (US Pat No.
  • Some lubricating additives currently used such as fatty acids, fatty acid amines or fatty acid amides, generally have a relatively large molecular weight, which solidifies at low temperatures, and sometimes even at room temperature, solidification occurs during the placement, and the solidified crystals are precipitated from the solution, thereby Causes trouble in operation.
  • Dilution with an organic solvent can increase the crystallization temperature, which is called a cloud point or a cloud point, but this can only partially solve the problem because some components are still crystallized after dilution, and the solvent is also possible. It is colloidized and cured.
  • a large molecular weight fatty acid, a fatty acid amine or a fatty acid amide when used as a lubricating additive, it must be diluted in a large amount or stored in a heated container or added through a heating tube.
  • US Pat. No. 7,867, 295 B2 discloses that a branched carboxylic acid having 6 to 14 carbons can be used as a lubricant improver for hydrocarbon fuels (diesel, kerosene, gasoline, etc.), typical banding
  • the carboxylic acids of the chain are isostearic acid, neodecanoic acid, isophthalic acid, neodecanoic acid and isodecanoic acid, etc. They may be saturated or unsaturated, and they may be saturated with other linear chains. Saturated carboxylic acids, as well as mono-, di- and tricarboxylic acids, etc.
  • Typical linear carboxylic acids are oleic acid, linoleic acid, stearic acid, tall oil Tall oil fatty acid, linolenic acid, palmitic acid, coco fatty acid, and ricinoleic Acid) and so on.
  • the cloud point of the mixture can be lowered by 3-6.
  • wear scar diameter can be reduced by 5-10%, however, these branched carboxylic acids are low in nature, complex in synthesis, and generally costly.
  • some of the lubricating additives currently used such as fatty acids, fatty acid amines or fatty acid amides, generally have a relatively large molecular weight, solidify at low temperatures, and solidify even at room temperature, and the solidified crystals are precipitated from the solution. This causes trouble in operation. Dilution with an organic solvent can only partially solve the problem because some components are still crystallized after dilution, and the solvent may be colloidalized and cured. Moreover, most organic solvents are not effective in reducing linear carboxylic acid antiwear agents. Therefore, when fatty acids, fatty acid amines or fatty acid amides are used as antiwear additives, they must be diluted or stored in heated containers.
  • the application of the present invention is to solve the above problems of the anti-wear agent used in the current hydrocarbon fuel, and to provide an anti-wear agent which can improve the low-temperature stability and flowability of the existing anti-wear agent.
  • New antiwear agents for performance and methods of use are provided.
  • the antiwear agent comprises a short chain fatty acid amide and a linear fatty acid, wherein the short chain fatty acid amide has the following formula compound of: Wherein R1, R2, and R3 are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and the total number of carbon atoms contained in R1, R2, and R3 is ⁇ 10.
  • the mass ratio of the short-chain fatty acid amide to the linear fatty acid is 1:100-10:1, preferably 1:50-2:1, more preferably 1:20-1: 1 , the best is 1: 10 ⁇ 1: 4.
  • the short-chain fatty acid amide comprises dimethylformamide (DMF) or N, N, N, N'-dimethylacetamide (DMAC).
  • the linear fatty acid includes a natural or artificially synthesized fatty acid having 3 to 60 carbon atoms or a mixture of one or more thereof, preferably a long-chain fatty acid having 10 to 60 carbon atoms. Or a mixture of one or more thereof; including oleic acid, linoleic acid, stearic acid, tall oil fatty acid, linolenic acid, palm Oil (palitic acid), coco fatty acid, ricinoleic acid, coconut oil, etc., and various synthetic fatty acids or a mixture of one or more thereof.
  • the ratio of the mixture of the short-chain fatty acid amide and the linear fatty acid varies depending on the type of the short-chain fatty acid amide and the linear fatty acid selected, and generally the pour point and the cloud point decrease with the short chain.
  • the proportion of the fatty acid amide increases and the specific addition amount can be determined by the test depending on the temperature of the use region. If the lowest temperature in the area is -5 °C, different amounts of short-chain fatty acid amide can be added to the linear fatty acid, and the cloud point and pour point are measured.
  • the cloud point refers to the liquid sample such as oil and varnish under standard conditions.
  • Pour point is the lowest temperature at which the cooled sample can flow under the specified test conditions, and is one of the parameters reflecting the low temperature fluidity of the oil. The lower the pour point, the better the low temperature fluidity of the oil; until the cloud point and pour point are higher than -5 °C.
  • Another object of the present application is to provide an anti-wear agent for use in a hydrocarbon-based fuel.
  • the application includes adding the anti-wear agent into a hydrocarbon fuel (including gasoline and diesel), effectively improving the stability during storage of the linear fatty acid anti-wear agent and the operability at low temperatures, reducing the engine
  • the surface of the oil pump and the nozzle is deposited and worn to improve the use of hydrocarbon fuels such as gasoline and diesel.
  • the anti-wear agent described in the present application includes, in addition to short-chain fatty acid amides and linear fatty acids, other hydrocarbon fuel additives, including detergents, antiknock agents, combustion catalysts, and cetane number improvement.
  • Agent pour point depressant, low temperature fluidity improver, anti-clouding agent, corrosion inhibitor, fungicide, antioxidant, stabilizer, fixative, demulsifier, copper corrosion inhibitor, conductivity additive, dyeing Or tracer (dye / marker), etc.
  • the anti-wear agent described in the application of the invention can improve the stability and fluidity of the existing long-chain fatty acid anti-wear agent under low temperature conditions, further improve the lubrication or drag reduction performance, and increase the operation convenience of the anti-wear agent. Compared with other similar methods, the degree and efficiency of use are relatively low, and the effect is good. In cold regions, especially in remote areas, when the pipeline heating is difficult to achieve, the anti-wear agent has a practical value of 4 ⁇ .
  • the cloud point and the pour point are greatly reduced after adding different proportions of dimercaptophthalamide (DMF) in tall oil.
  • DMF dimercaptophthalamide
  • the magnitude of the decrease varies with the amount of DMF added.
  • the cloud point and the pour point gradually decrease as the amount of DMF added increases.
  • Add 10% DMF ie DMF as a percentage of the mixture of short-chain fatty acid amide and linear fatty acid
  • cloud point and pour point of tall oil and DMF mixture measure of cloud point is ASTM D2500, pour point
  • the measurement method is ASTM D97, which is a common technical means in the field, and will not be described here.
  • the Tall oil without DMF is reduced by 3 °C. If 20% DMF is added, the cloud point and pour point are lowered respectively. 8 ! And 9 °C. Changes in cloud point and pour point after adding DMF to tall oil fatty acid FA-2
  • Example 2 As shown in Table 2, the addition of DMF to another tall oil fatty acid having a different origin also significantly reduced the cloud point and pour point of tall oil. Adding 20% DMF to tall oil, the cloud point and pour point of the mixture were reduced by 9 °C compared to the absence of DMF. Table-2 Changes in cloud point and pour point after adding DMF to tall oil fatty acid FA-2.
  • Example 5 After adding different amounts of DMF to palm oil, cocoa fatty acid and coconut oil, the pour point was significantly reduced. See Table-5: Table-5 Adding different amounts to palm oil, cocoa fatty acid and coconut oil respectively Effect of DMF on its pour point
  • Example 6 After adding different amounts of DMAC to palm oil, cocoa fatty acid and coconut oil, the pour point was significantly reduced, as shown in Table-6: Table-6. Different amounts were added to palm oil, cocoa fatty acid and coconut oil. Effect of DMAC on its pour point
  • Example 7 In the application of an antiwear agent, the method using a mixture of a short chain fatty acid amide and a linear fatty acid did not reduce the abrasion resistance of the method using a linear fatty acid alone.
  • the measurement method of diesel abrasion resistance is ASTM D6079 (Standard Test Method for Evaluating Lubricity of Diesel Fuels by the High - Frequency Reciprocating Rig (HFRR)), and the anti-wear agent A of Table-7 is 100% octadecadiene.
  • Acid, anti-wear agent B is 80% octadecadienoic acid + 20% DMAC.
  • Diesel lubricity (measuring method of wear scar diameter ASTM D6079, unit ⁇ ) Daqing 0 # diesel Antiwear agent
  • Antiwear agent C is 100% tall oil fatty acid
  • antiwear agent D is 80% tall oil fatty acid + 20% DMF.
  • Diesel lubricity (measurement method for wear scar diameter ASTM D6Q79, unit ⁇ )

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne un agent anti-usure de combustible hydrocarboné. Les constituants principaux de l'agent anti-usure comprennent un amide d'acide gras à chaîne courte et un acide gras à chaîne linéaire. L'amide d'acide gras à chaîne courte est un composé de formule générale (I), R1, R2 et R3 étant des atomes d'hydrogène ou des alkyles comprenant chacun 1 à 10 atomes de carbone, et le nombre total d'atomes de carbone compris dans R1, R2 et R3 étant inférieur ou égal à 10. Le rapport massique entre l'amide d'acide gras à chaîne courte et l'acide gras à chaîne linéaire est de 1:100 à 10:1. L'amide d'acide gras à chaîne courte comprend le diméthylformamide ou le Ν, Ν'-diméthylacétamide. L'acide gras à chaîne linéaire comprend un acide gras naturel ou synthétique comprenant 3 à 60 atomes de carbone ou un mélange comprenant plus d'un type de l'acide gras naturel ou synthétique. En comparaison de l'agent anti-usure à base d'acide gras à chaîne longue existant, l'agent anti-usure de la présente invention permet d'améliorer la stabilité et la fluidité à une température basse, améliore également les performances de lubrification ou de réduction des traînées, et augmente le degré de commodité opérationnelle et les performances d'utilisation, et présente un faible coût, un bon effet et des perspectives d'application larges.
PCT/CN2011/083194 2011-11-30 2011-11-30 Agent anti-usure de combustible hydrocarboné et son procédé d'utilisation WO2013078631A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2011/083194 WO2013078631A1 (fr) 2011-11-30 2011-11-30 Agent anti-usure de combustible hydrocarboné et son procédé d'utilisation
CN201180075206.5A CN104024387A (zh) 2011-11-30 2011-11-30 一种碳氢燃料抗磨剂及其使用方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2011/083194 WO2013078631A1 (fr) 2011-11-30 2011-11-30 Agent anti-usure de combustible hydrocarboné et son procédé d'utilisation

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WO2013078631A1 true WO2013078631A1 (fr) 2013-06-06

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107033976A (zh) * 2016-12-16 2017-08-11 安阳市宇泰化工有限公司 一种低凝点高效柴油抗磨剂及其制备方法
CN110938479A (zh) * 2019-12-16 2020-03-31 兰州石化职业技术学院 一种石油化工助剂及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001115178A (ja) * 1999-10-14 2001-04-24 Tonengeneral Sekiyu Kk トラクションドライブ流体用低温流動性向上剤、トラクションドライブ流体組成物及び該低温流動性向上剤の製造方法
CN101668839A (zh) * 2007-04-24 2010-03-10 英菲诺姆国际有限公司 改进润滑油组合物中的高碱性清净剂与其它添加剂的相容性的方法
CN101974361A (zh) * 2010-08-20 2011-02-16 泰安天健应用技术推广中心 一种多功能纳米复合材料抗磨剂
CN102061199A (zh) * 2010-12-26 2011-05-18 西安市尚华科技开发有限责任公司 一种清洁柴油

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001115178A (ja) * 1999-10-14 2001-04-24 Tonengeneral Sekiyu Kk トラクションドライブ流体用低温流動性向上剤、トラクションドライブ流体組成物及び該低温流動性向上剤の製造方法
CN101668839A (zh) * 2007-04-24 2010-03-10 英菲诺姆国际有限公司 改进润滑油组合物中的高碱性清净剂与其它添加剂的相容性的方法
CN101974361A (zh) * 2010-08-20 2011-02-16 泰安天健应用技术推广中心 一种多功能纳米复合材料抗磨剂
CN102061199A (zh) * 2010-12-26 2011-05-18 西安市尚华科技开发有限责任公司 一种清洁柴油

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107033976A (zh) * 2016-12-16 2017-08-11 安阳市宇泰化工有限公司 一种低凝点高效柴油抗磨剂及其制备方法
CN110938479A (zh) * 2019-12-16 2020-03-31 兰州石化职业技术学院 一种石油化工助剂及其制备方法

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