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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/14—Esterification
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/28—Condensation with aldehydes or ketones
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
  • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
  • C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2810/00—Chemical modification of a polymer
  • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
• • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
• • 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
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups

Definitions

• This invention relates to jet combustion fuels that are stable at relatively high temperatures. It is more particularly concerned with jet combustion fuels adapted for use in high temperature jet engines and with novel additive compositions therefor.
• Another object of this invention is to provide stable jet combustion fuels. Another object is to provide a means for stabilizing jet combustion fuels against thermal degradation. A further object is to provide jet combustion fuels having a greatly reduced tendency to foul heat exchange tubes and to plug injection nozzles. A specific object is to provide jet combustion fuels containing an additive composition of certain esters and certain metal deactivating compounds. A more specific object is to provide jet combustion fuels containing the reaction product of certain partial esters with polyamines and hydroxyarornatic aldehyde. Other objects and advan tages of this invention will become apparent to those skilled in the art from the following detailed description.
• the present invention provides an additive composition
• an additive composition comprising the reaction product obtained by l) esterifying a 1:1 molar copolymer of a l-olefin, having between about 2 carbon atoms and about carbon atoms per molecule, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of a primary or secondary aliphatic alcohol containing between about 4 carbon atoms and about 20 carbon atoms per molecule to produce a mixed monoand di-ester product; (2) reacting said ester prodnot with between about 0.25 mole and about 0.50 mole of a polyarnine of the formula H N(R-NI-l) -H, wherein R is ethylene or propylene and n is 1 or 2, and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product; and a jet combustion fuel containing between about 0.001 percent and about one percent, by weight, of the
• the mixed monoand di-ester product used in the reaction products of this invention is the mixed monoand di-aliphatic ester of certain olefin-maleic anhydride heteropolymers.
• the heteropolymer is produced by copolymerizing equimolar amounts of a l-olefin and maleic acid anhydride.
• the l-olefin reactant should contain between about 2 carbon atoms and about 20 carbon atoms per molecule.
• the reactants are heated together, either in bulk, or in the presence of a suitable solvent, such as benzene, toluene, xylene, dioxane, or carbon tetrachloride, at temperatures varying between about C. and about 175 C.
• the copolyrnerization is carried out in the presence of a peroxide catalyst, such as benzoyl peroxide.
• a peroxide catalyst such as benzoyl peroxide.
• the amount of peroxide used is between about one percent and about 5 percent, by weight of the reactants.
• the time required to complete the eop-olyrnerization varies between about one hour and about 10 hours.
• the mixed monoand di-aliphatic ester is made by esterifying the heteropolymer with a primary or secondary aliphatic alcohol containing between about 4 carbon atoms and about 20 carbon atoms per molecule.
• the branched-chain alkyl alcohols are particularly preferred.
• Non-limiting examples of the esterifying alcohols are butanol; Z-methyl-propanol; 2,2-dimethyl-propanol; amyl alcohol; isoamyl alcohol; hexanol; hexenol; 3-methylpentanol; Z-ethylhexanol; isodecanol; decanol; dodecanol; iso-tridecanol; hexadecanol; hexadecenol; octadecanol; octadecenol; and eicosanol.
• the esters utilizable herein must be a mixed monoand dialiphatic ester. Accordingly, the alcohol reactant is reacted with the olefin-maleic anhydride in amounts of between about l.5 moles and about 1.75 moles per mole of olefin-maleic anhydride copolymer.
• the ester can be made by any of the known methods for preparing esters of earboxylic acids.
• the mixed esters of l-olefin-rnaleic anhydride copolymers can be prepared by heating at -200 C., from 1 to 10 hours, one mole of l-olefin-maleic anhydride copolymer with l.5l.75 moles of alcohol with the elimination of 0.5-0.75 mole of water.
• the esterification is suitably carried out in the presence of a catalyst, such as p-toluene sulfonic acid monohydrate or sulfuric acid.
• the amount of p-toluene sulfonic acid monohydrate or sulfuric acid used is from 0.1 percent to 5 percent by weight or" the reactants.
• various techniques of esterification such as azeotropic distillation. or removal of water by the use of applied vacuum. It is to be understood that the particular method used to prepare the mixed ester component is of little importance to the additive compositions of this invention or to the jet combustion fuels containing them.
• the mixed monoand (ii-aliphatic ester component is then further reacted with, per mole of mixed ester, be tween about 0.25 mole and about 0.5 mole of a polyreactant as hereinafter defined and between about 0.25 mole and about 0.5 mole of salicylaldehyde.
• the polyarnine reactant has the formula H N(,RNH) H, wherein R is ethylene or propylene and n is 1 or 2.
• R is ethylene or propylene and n is 1 or 2.
• the polyamine reactant are ethylenediamine, propylenediamine, diethylenetriamine and dipropylenetriamine.
• the reaction between the copolymer ester, polyamine reactant, and salicylaldehyde is a condensation reacti n accompanied by the formation of water of reaction.
• the reaction is suitably carried out at temperatures varying between about 90 C. and about C. and for a period of time varying between about one hour and about 5 hours, or untii water of condensation ceases to form.
• various techniques of esterification are equally applicable to the reaction with amine and salicylaldehyde.
• water can be removed by azeotropic distillation.
• the hydrocarbon jet fuels that are improved in accordance with this invention are hydrocarbon fractions having an initial boiling point of at least about 100 F. and an end boiling point as high as about 750 F. These fuels can be made up of straight-run distillate fractions, catalytically or thermally cracked (including hydrocracked) distillate fractions, or mixtures of straight-run fuel oil, naphtha, etc. with cracked distillate stocks, alkylate, and the like.
• the principal properties that charac terize the jet fuels is their boiling range. Each fuel will have a boiling range which falls within the aforespecified range.
• Specifications that define typical specific fuels are MIL-F-5616, MIMI-5624B, MIL-F25656, MIL- F-2524A, MIL-F25576A, MIL-F25558B, and MIL- J-5161E.
• the amount of additive composition, i.e., reaction product aforedescribed, that is added to the jet combustion fuels will vary between about 0.001 percent and about one percent, by weight of the fuel, and preferably be tween about 0.01 percent and about 0.02 percent.
• the concentration of additive composition will vary between about 5.0 pounds per thousand barrels of fuel and about 2000 pounds per thousand barrels of fuel. Preferably, the concentration will vary between about 25 pounds per thousand barrels of fuel and about 50 pounds per thousand barrels of fuel.
• Olefin A is a mixture containing about 8.2 weight percent l-hexene, about 7 weight percent l-decene, about 48 weight percent l-dodecene, about 17.5 weight percent l-tetradecene, about 8.8 weight percent l-hexadecene, and about 10.5 weight percent 1- octadecene.
• Olefin B is a mixture containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene.
• Alcohol C is a mixture of normal aliphatic, monohydric alcohols containing about 2.8 weight percent decanol, about 61 weight percent dodecanol, about 21 weight percent tetradecanol, about 11 weight percent hexadecanol, an dabout 2.2 weight percent octadecanol.
• Example 1 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 161 C., then dropped. The mixture was stirred at 150155 C. for 4 hours to complete copolymerization. To the copolymer was added, at room temperature with stirring, 65 grams (0.875 mole) of nbutyl alcohol, 6 grams (2.6%) of p-toluene sulfonic acid monhydrate and 200 cc. of benzene.
• the mixture was refluxed at 105 C. for 8 hours and 150 C. for 2 hours to form a mixture of mono-ester and di-ester.
• the amount of water collected during the esterification was 7 cc., theory 6.75 cc.
• the ester mixture was diluted with 200 cc. of benzene and water-washed until the water layer was neutral.
• To the water-washed ester mixture was added at room temperature with stirring 15.25 grams (0.125 mole) of salicylaldehyde and 7.5 grams (0.125 mole) of ethylenediamine.
• the mixture was refluxed at C. for 2 hours and 150155 C. for 2 hours.
• the amount of water collected during the reflux was 4.5 cc., theory 4.5 cc.
• the reaction product was diluted with 200 cc. of benzene, water-washed and topped to 165 C. under a pressure of 1 mm. of mercury.
• Example 2 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at C. The reaction was exothermic, and the temperature rose rapidly to 178 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete copolymerization. The copolymer was diluted with 200 cc. of toluene.
• Example 3 A mixture of grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned oil at 100 C. The reaction was exothermic, and the temperature rose rapidly to 178 C., then dropped. The mixture was stirred at 155 C. for 4 hours to complete copolymerization. The copolymer was diluted with 250 cc. of xylene. To the copolymer was added at room temperature 138 grams (0.875 mole) of isodecyl alcohol and 6.04 grams (2%) of p-toluene sulfonic acid monohydrate.
• the mixture was refluxed at 150 C. for 4 hours and 175 C. for 2 hours to form a mixture of mono-ester and di-ester.
• the amount of water collected during the esterification was 7 cc., theory 6.75 cc.
• the ester mixture was diluted with 150 cc. of benzene and water-washed until the water layer was neutral.
• To the water-washed ester mixture was added at room temperature with stirring 15.25 grams (0.125 mole) of salicylaldehyde and 7.5 grams (0.125 mole) of ethylenediamine.
• the mixture was refluxed at 95 C. for 3 hours and 150- C. for 2 hours.
• the amount of water collected during the reaction was 5 cc., theory 4.5 cc.
• the reaction product was diluted with 300 cc. of benzene, waterwashed and topped to 150 C. under a pressure of 1.5 mm. of mercury.
• Example 4 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 154 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete copolymerization. The copolymer was diluted with 100 cc. of xylene.
• Example 5 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 1.65 grams (1%) of benzoyl peroxide and 30 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 156 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete copolymerization. The copolymer was diluted with 150 cc. of toluene. To the copolymer was added at room temperature 175 grams (0.875 mole) of alcohol C and 5.5 grams (1.5%) of p-toluene sulfonic acid monohydrate.
• the mixture was refluxed at 130150 C. for 3 hours to form a mixture of mono-ester and (ii-ester.
• the amount of water collected during the reflux was 7 cc., theory 6.75 cc.
• the ester mixture was diluted with 100* cc. of benzene.
• To the ester mixture was added gradually at room temperature with stirring 7.5 grams (0.125 mole) of ethylenediamine and 15.25 grams (0.125 mole) of salicylaldehyde.
• the mixture was refluxed at 102 C. for 2 hours and 150 C. for 3 hours.
• the reaction product was diluted with 500 cc. of benzene, water-washed and topped to 160 C. under a pressure of 1.5 mm. of mercury.
• Example 6 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. or" xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 150 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete copolymerization. The copolymer was diluted with 100 cc. of xylene.
• Example 7 A mixture of 70 grams (0.5 mole) of l-decene, 49 grams (0.5 mole) of maleic anhydride, 1.19 grams (1%) of benzoyl peroxide and 25 cc. of xylene was gradually heated with stirring. Heat was turned off at C. The reaction was exothermic, and the temperature rose rapidly to 152 C., then dropped. The mixture was stirred at C. for 3 hours to complete copolymerization. The copolymer was diluted with 100 cc. of xylene. To the copolymer was added at room temperature with stirring 175 grams (0.875 mole) of isotridecyl alcohol and 2.94 grams (1% of p-toluene sulfonic acid monohydrate.
• the mixture was gradually heated to 175 C., and held at 175 C. for 3 hours to complete the formation of a mixture of mono-ester and di-ester.
• the amount of water collected during the esterification was 6 cc., theory 6.75 cc.
• the ester mixture was diluted with 100 cc. of benzene.
• To the ester mixture was added at room temperature with stirring 15.25 grams (0.125 mole) of salicylaldehyde and 7.5 grams (0.125 mole) of ethylenediamine.
• the mixture was gradually heated to 150 C., and the temperature was held at 150 C. until water stopped coming over (about 2 hours).
• the amount of water collected during the reaction was 4.5 cc., theory 4.5 cc.
• the reaction product was diluted with 100 grams of xylene and was filtered through I-iiflo clay.
• Example 8 A mixture of 84 grams (0.5 mole) of l-dodecene, 49 grams (0.5 mole) of maleic anhydride, 2.66 grams (2%) of benzoyl peroxide and 25 cc. of xylene was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 155 C., then dropped. The mixture was stirred at 150-155 C. for 3 hours to complete copolymerization. The copolymer was diluted with 250 cc. of xylene.
• Example 9 A mixture of 127 grams (0.5 mole- ⁇ -12 rams excess) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 1.64 grams (1% of benzoyl peroxide and 50 cc. of xylene as diluent was stirred at 75-80 C. for 6 hours to complete copolymerization. The copolymer was diluted with 100 cc. of xylene. To the copolymer was added at room temperature with stirring 150 grams (0.75 moie) of isotridecyl alcohol and 3.14 grams (1%) of p-toluene sulfonic acid monohydrate. The mixture was refluxed at 150 C. for 4 hours and 175 C.
• the amount of water collected during the esteriflcation was 4.5 cc., theory 4.5 cc.
• the ester mixture was diluted with 100 cc. of xylene and 150 cc. of benzene. T o the ester mixture was added at room temperature with stirring 16.75 grams (0.125 mole]-1.5 grams excess) of salicylaldehyde and 7.5 grams (0.125 mole) of ethylenediamine. The mixture was refluxed at 8595 C. for 2 hours and 148 C. for 2 hours. The amount of water collected during the reflux was 5 cc., theory 4.5 cc.
• the product contained 22% xylene and was fluid at room temperature.
• Example 10 A mixture of 99 grams (0.5 mole+9 grams excess) of olefin A, 49 grams (0.5 mole) of maleic anhydride, 1.39 grams (1%) of benzoyl peroxide and 50 cc. of xylene was gradually heated with stirring. Heat was turned oil? at 100 C. The reaction was exothermic, and the temperature rose rapidly to 149 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete copolymer-ization. The copolymer was diluted with 100 cc. of xylene and 50 cc. of benzene.
• Example 11 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 175 C., then dropped. The mixture was stirred at 150* C. for 4 hours to complete copolymerization. The copolymer was diluted with 100 cc. of xylene and 50 cc. of benzene.
• Example 12 A mixture of 115 grams (0.5 mole) of olefin B, 49 grams (0.5 mole) of maleic anhydride, 2.5 grams (1.5%) of benzoyl peroxide and 25 cc. of xylene as diluent was gradually heated with stirring. Heat was turned off at 100 C. The reaction was exothermic, and the temperature rose rapidly to 166 C., then dropped. The mixture was stirred at 150 C. for 4 hours to complete compolymerization. The copolymer was diluted with 100 cc. of xylene.
• the test method used for determining the thermal stability characteristics of aviation turbine fuels is a method developed by the Coordinating Research Council which was published in CRC Report Investigation of Thermal Stability of Aviation Turbine Fuels With CFR Fuel Coker (CRC Project CFA2-54), July 1957. The method is set forth in detail in Appendix XV of the ASTM Standards on Petroleum Products and Lubricants, November 1957, commencing at page 1059.
• This method provides a means for measuring the high temperature stability of aviation turbine fuels, using an apparatus known as the CPR Fuel Coker, which subjects the test fuel to temperatures and conditions similar to those occurring in some aviation turbine engines.
• Fuel is pumped, at a rate of about 6 pounds per hour, through a preheater section which simulates the hot fuel line sections of the engine as typified by an engine fuel-oil cooler. It then passes through a heated filter section which represents the nozzle area or small fuel passages of the hot section of the en gine where fuel degradation products may become trapped.
• a precision sintered stainless steel filter in the heated filter section traps fuel degradation products formed during the test. The extent of the build-up is noted as an increased pressure drop across the test filter and, in combination with the deposit condition of the preheater, is used as an assessment of the fuels high-temperature stability.
• the filter temperature was 500 F. and the preheater tube temperature was 400 F.
• the base hydrocarbon jet combustion fuel used herein was a straight-run petroleum fraction boiling between about 325 F. and about 525 F. A portion of this base fuel, uninhibited was subjected to the Fuel Coker Test. Then, other portions of the base fuel were blended with the reaction products of the foregoing examples, and each blend so obtained was subjected to the Fuel Coker Test. Pertinent blend data and test results are set forth in the following table:
• Fuel-l-Example 1 50 0.0 300 Code 0. Fuel+Example 2 30 0. 0 300 Code 1. Fuel-l-Example 3 r 30 0.0 300 Code 0. Fuel+Example 4 50 0.0 300 Code 0. Fuel+Example 5- 10 0. 0 300 Code 0. Fuel+Example 6- l0 0. 0 300 Code 0. Fuel-l-Example 7 30 0.0 300 Code 0. Fue1+Example 8 5 0. 0 300 Code 0. Fuel-l-Example 9- -r 50 0.0 300 Code 0. Fuel+Example 10-- 30 0.0 300 Code 1. Fuel-i-Example 11 50 0.0 300 Code 3. Fue1+Examp1e l2 50 0.0 300 Code 3.
• reaction products of this invention are effective jet fuel stabilizers. Some, however, are more effective than others, in that they are effective at lower concentrations.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of a l-ole'fin, having between about 2 carbon atoms and about 20 carbon atoms per molecule, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of an aliphatic alcohol containing between about 4 carbon atoms and about 20 carbon atoms per molecule to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of a polyamine of the formula H N(--R-NH),,H, wherein R is selected from the group consisting of ethylene and propylene and n varies between 1 and 2, and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by -(1) esterifying a 1:1 molar copolymer of a l-oleiin mixture, containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadccene, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of butanol to produce a mixed monoand diester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer of Z-ethylhexanol to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mOle salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by '(1) esterifying a 1:1 molar copolymer of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent 1dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene, and maleic acid anhydride with about 1.75 moles, per mole of said copolymer, of isotridecanol to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of a mixture of normal aliphatic alcohols containing about 2.8 weight percent decanol, about 61 weight percent dodecanol, about 21 weight percent tetradecanol, about 11 weight percent hexadecanol, and about 2.2 weight percent octadecanol to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylene
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent 1-dodec-ene, about 20 weight percent l-tetradecene, about 10.5 weight percent lhexadecene, and about 0.5 weight percent l-octadecene, and maleic acid anhydride with between about 1:5 moles and about 1.75 moles, per mole of said copolymer, of octadecenol to produce a mixed rnonoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester prodnot.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of decene-l and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of isotridecanol to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylene diamine and between about 0.25 mole and about 0.50 rnole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of dodecene-1 and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of isotridecanol to produce a mixed mono and di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1: 1 molar copolymer of a l-olefin mixture, containing about 3 weight percent 1- decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene, and maleic acid anhydride with about 1.5 moles, per mole of said copolymer, of isotridecanol to produce a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1:1 molar copolymer of a 1olefin mixture, containing about 8.2 weight percent l-hexene, about 7 weight percent l-decene, about 48 weight percent 1-dodecene, about 17.5 weight percent 1- tetradecene, about 8.8 weight percent l-hexadecene, and about 10.5 weight percent l-octadecene, and maleic acid anhydride with between about 1.5 moles and about 1.75 moles, per mole of said copolymer, of isodecanol to pro prise a mixed monoand di-ester product; (2) reacting said ester product with between about 0.25 mole and about 0.50 mole of ethylenediamine and between about 0.25 mole and about 0.50 mole salicyl aldehyde, per mole of said ester product.
• An additive composition comprising the reaction product obtained by (1) esterifying a 1.1 molar copolymer of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent product obtained by (1) esterifying a 1:1 molar copolymer 10 of a l-olefin mixture, containing about 3 weight percent l-decene, about 66 weight percent l-dodecene, about 20 weight percent l-tetradecene, about 10.5 weight percent l-hexadecene, and about 0.5 weight percent l-octadecene,
• ester product with between about 0.25 mole and about 0.50 mole of diethylenetriamine and be tween about 0.25 mole and about 0.50 mole salicylaldehyde, per mole of said ester product.

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  • BE BE599357D patent/BE599357A/xx unknown
• 1961
  • 1961-12-07 US US157822A patent/US3115483A/en not_active Expired - Lifetime

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