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
  • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular 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, 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
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
• • 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
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
• • 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
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
• • 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
  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
• • 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
  • C10L1/234—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, 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
  • C10L1/234—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)
  • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and 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, 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
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
  • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
  • C10L1/2475—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds

Definitions

• This disclosure relates to an additive composition comprising at least one antistatic agent and at least one strong acid.
• the additive composition can be combined/blended/admixed with a middle distillate fuel to form a fuel composition.
• Methods of making and using the additive and fuel compositions are also disclosed. Also disclosed are methods of improving and/or prolonging the ability of an additive composition to impart effective conductivity to a fuel.
• Certain middle distillate fuel compositions are capable of generating static electricity, particularly when moving rapidly, such as when the fuel is being dispensed into a tanker or other bulk container or vessel. While diesel fuels are not very volatile, the tankers used to transport diesel fuels are also used to transport gasoline, kerosene and other more volatile and flammable liquids. Even after the more volatile fuel is dispensed from the tanker, the vapors may still be present and pose a risk of fire or explosion from a spark generated by the discharge of static electricity from the fuel composition.
• conductivity improver improves the conductivity of the fuel, thus permitting any static charge built up during high volume transport of the fuel to safely dissipate without generating a spark.
• Conductivity improvers are also known as antistatic agents.
• the Stadis® brand of antistatic agents contain sulfur.
• Sulfur-containing antistatic agents present a problem when used with additive concentrates that contain basic nitrogen. Specifically, the ability to deliver conductivity improvement by a sulfur-containing antistatic agent dissipates very rapidly when used in additive concentrates containing basic nitrogen because of a reaction between the two materials. This is disadvantageous because it prevents pre-blending of these antistatic agents into additive concentrates that contain basic nitrogen.
• a typical fuel additive concentrate may include nitrogen-containing compounds, such as dispersants, detergents, cold flow improvers, lubricity improvers, corrosion inhibitors, stabilizers, and the like.
• nitrogen-containing compounds such as dispersants, detergents, cold flow improvers, lubricity improvers, corrosion inhibitors, stabilizers, and the like.
• compositions and methods to address the build-up and discharge of static electricity in middle distillate fuel compositions.
• a multifunctional diesel fuel additive package that when stored does not lose the ability to deliver conductivity to the fuel.
• an additive composition comprising at least one antistatic agent; and a strong acid, wherein the at least one antistatic agent and the strong acid are present in the additive composition in a weight ratio of from about 1:0.05 to about 1:1.
• a pre-blended additive composition comprising at least one antistatic agent; and a strong acid, wherein the at least one antistatic agent and the strong acid are present in the additive composition in a weight ratio of from about 1:0.05 to about 1:1.
• a method of improving the conductivity in a fuel comprising combining, with the fuel, a strong acid with a composition comprising an antistatic agent and a basic, nitrogen-containing component; wherein the strong acid is combined in an amount sufficient to neutralize at least a portion of the basic nitrogen in the component.
• less than all of the basic nitrogen needs to be neutralized to stabilize deliverable conductivity.
• only about 40%-70% of the basic nitrogen needs to be neutralized by the use of additional strong acid.
• the amount of basic nitrogen to be neutralized can vary and may be impacted by both steric availability and basicity leading in one embodiment to less than 40% of the basic nitrogen reacting with the antistatic agent.
• the present disclosure relates to an additive composition
• an additive composition comprising at least one antistatic agent; and a strong acid, wherein the at least one antistatic agent and the strong acid are present in a weight ratio of from about 1:0.05 to about 1:1.
• the additive composition can be combined/mixed/blended with a middle distillate fuel to form a fuel composition.
• the strong acid can, in one embodiment, be combined/mixed/blended with the antistatic agent in an amount sufficient to neutralize at least a portion (40-70%) or all of the basic nitrogen.
• improved conductivity is used to indicate that the ability of the additive package to provide conductivity to the fuel does not decline by more than about 50% from an initial measure with the conductivity additive alone. This measure is taken within 3 hours of storing the additive composition at 90°C. For example, in one embodiment the conductivity effect does not decline by more than about 30% within that 3 hour period at 90°C. As a further example, the conductivity measure declines by no more than about 30% for a period of at least 7 hours at 90°C. In some aspects, the conductivity measure can still be at least about 50% of its initial measure after 10 hours 90°C following the preparation of the additive composition. Thus another embodiment herein provides prolonged conductivity performance of the additive package.
• a method of prolonging the conductivity performance of an additive composition comprising combining a strong acid with a composition comprising an antistatic agent, wherein the composition comprises a basic, nitrogen-containing component; and wherein the antistatic agent and the strong acid are combined in a weight ratio of about 1:0.05 to 1:1.0
• Useful basic, nitrogen-containing components such as dispersants, are known to those skilled in the art, but can include for example hydrocarbyl-substituted succinimides, polyetheramines, and Mannich base reaction products.
• conductivity benefit is used to indicate that the conductivity imparted by the additive composition is sufficient to provide a conductivity of the fuel of at least about 25 pS/m at the time and temperature of delivery of the fuel. All examples herein are well above this value, when measured at room temperature.
• the present compositions can be particularly suited for middle distillate fuel compositions.
• Middle distillate fuel compositions include, but are not limited to, jet fuels, diesel fuels, and kerosene.
• the fuel is a low-sulfur fuel having less than about 500 ppm sulfur, for example less than about 350 ppm of sulfur.
• the fuel can be an ultra-low sulfur diesel fuel or ultra-low sulfur kerosene.
• Ultra-low sulfur fuels can be generally considered to have no more than about 30 ppm of sulfur, for example no more than about 15 ppm of sulfur, and as a further example no more than about 10 ppm of sulfur.
• diesel fuel is generally considered to be a generic term encompassing diesel, biodiesel, biodiesel-derived fuel, synthetic diesel and mixtures thereof. All disclosures herein to parts per million "ppm" are by mass unless otherwise indicated.
• jet fuels although these are conventionally not regarded as "low-sulfur” or “ultra-low sulfur” fuels because their sulfur levels can be comparatively quite high. Nevertheless, jet fuels may also benefit from the conductivity improvement of the present embodiments regardless of their sulfur content.
• the antistatic agent for use in the disclosed compositions can in one embodiment comprise, based on total weight, from about 5 to 25 percent of a polysulfone, from about 5 to 25 percent of a polymeric polyamine, from about 5 to 30 percent of oil-soluble sulfonic acid, and from about 20 to 85 percent of solvent.
• the polysulfone copolymers often designated as olefin-sulfur dioxide copolymer, olefin polysulfones, or poly(olefin sulfone) can be or comprise, for example, linear polymers wherein the structure is considered to be that of alternating copolymers of the olefins and sulfur dioxide, having a one-to-one molar ratio of the comonomers with the olefins in head to tail arrangement.
• the polysulfones used herein are readily prepared by the methods known in the art (cf. Encyclopedia of Polymer Science and Technology Vol. 9, Interscience Publishers, page 460 et seq .).
• the polyamine component of the antistatic agent disclosed herein can be or comprise, for example, a polymeric reaction product of epichlorohydrin with an aliphatic primary monoamine or N-aliphatic hydrocarbyl alkylene diamine.
• the polymeric reaction products can be prepared by heating an amine with epichlorohydrin in the molar proportions of from 1:1-1.5 in the temperature range of about 50°C to about 100° C. Generally, with aliphatic monoamines the molar ratio can be about 1:1.
• the initial reaction product is believed to be an addition product.
• the aminochlorohydrin upon reaction with an inorganic base can then form an aminoepoxide.
• the aminoepoxide which can contain a reactive epoxide group and a reactive amino-hydrogen, can undergo polymerization to provide a polymeric material containing several amino groups.
• the ratio of epichlorohydrin to amine and the reaction temperature used are such that the polymeric reaction product can contain from 2 to 20 recurring units derived from the aminoepoxide.
• the amount of strong acid incorporated in the additive composition can be an equivalent amount, that is, a sufficient amount of strong acid to, in one embodiment, neutralize at least a portion of or all the basic nitrogen, such as a dispersant, although lesser or greater than the equivalent amount can be used.
• an amount of the strong acid sufficient to neutralize a portion of the basic nitrogen can be used effectively to achieve the improved antistatic performance of the additive package.
• the antistatic agent and the strong acid can, in one embodiment, be present in a weight ratio of about 1:0.05 to about 1:1 depending upon the amount of basic nitrogen present in the additive composition.
• compositions and methods of the present embodiments can provide conductivity to a fuel of at least 25 pS/m at the time and temperature of delivery.
• This conductivity is sufficient to meet the proposed new ASTM standard for conductivity in diesel fuels (ASTM D975 and amendments and appendices thereto) measured according to any appropriate test procedure, including but not limited to ASTM D2622 and ASTM D4951.
• ASTM D975 ASTM standard for conductivity in diesel fuels
• ASTM D4951 ASTM D2622 and ASTM D4951.
• This level of conductivity can be obtained and sustained for extended periods of time by the present embodiments.
• the disclosed fuel composition can exhibit improved conductivity as compared to a fuel composition devoid of the additive composition.
• the disclosed fuel composition can exhibit prolonged conductivity as compared to a fuel composition devoid of the additive composition.
• the fuel compositions of the present disclosure can contain supplemental additives in addition to the antistatic agent described above.
• the supplemental additives include, but are not limited to, dispersants/detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, additional antistatic agents, drag reducing agents, demulsifiers, dehazers, anti-icing additives, antiknock additives, cold flow improver, anti-valve-seat recession additives, lubricity additives and combustion improvers.
• the additives used in formulating the fuels of the present disclosure can be blended into the base fuel individually or in various sub-combinations. However, it is recommended to blend all of the components concurrently using an additive concentrate as this takes advantage of the mutual compatibility afforded by the combination of ingredients when in the form of an additive concentrate. Also use of a concentrate reduces blending time and lessens the possibility of blending errors.
• at least two components, such as the antistatic agent and the strong acid can be pre-blended.
• a method of prolonging the conductivity effect of an additive package in a fuel comprising: combining, with the fuel, an additive package comprising a strong acid and an antistatic agent, wherein the additive package comprises a basic, nitrogen-containing component; and wherein the antistatic agent and the strong acid are combined in a weight ratio of from about 1:0.05 to about 1:1.
• Examples 1-4 were prepared as blends of HiTEC® 4130WM, Stadis® 425 and Witconic TM 1298 Hard Acid.
• HiTEC® 4130WM is a multifunctional diesel fuel additive that contains a polyisobutylene succinimide, a cold flow improver, an ester lubricity additive, a demulsifier, a corrosion inhibitor and solvents and is available from Afton Chemical Corporation.
• HiTEC® 4130WM typically contains 0.032% nitrogen.
• Stadis® 425 is a sulfur-containing antistatic additive and is available from Innospec Fuel Specialties, LLC.
• Witconic TM 1298 Hard Acid is predominantly dodecylbenzene sulfonic acid (DBSA) and is available from Akzo Nobel Surface Chemistry, LLC.
• DBSA dodecylbenzene sulfonic acid
• the sample formulations were sealed in glass vials and placed in an oven set to 90°C for 16 hours. No fuel was present for the aging. This accelerated aging period is thought to be equivalent to about three (3) months storage at 20°C. After allowing the samples to cool at the end of the aging period, each was evaluated for its effect on improving the conductivity of an ultra-low sulfur diesel (ULSD) fuel (obtained from the Citgo pipeline terminal in Richmond, VA) at 22°C. The results are shown in Table 1.
• the test ULSD fuel had a measured conductivity of 0 picosiemens per meter (pS/m) without antistatic additive and 504 pS/m when treated with 5 ppm of Stadis® 425 by itself.
• a base multifunctional diesel fuel additive (“MFDA”) composition is shown in Table 2.
• the ester lubricity additive is an ethylene glycol diester of dimer acid.
• the cold flow improver is HiTEC® 4566 fuel additive (available from Afton Chemical Corporation), containing ethylene vinyl acetate copolymer and a nitrogen-containing wax anti-settling component to improve the low temperature filterability of the finished fuel.
• the cold flow improver contains 0.026 % nitrogen.
• the conductivity improver (antistatic agent) is Stadis® 425 and the solvent is Aromatic 100 fluid supplied by ExxonMobil Chemical. Table 2.
• Example 5-8 This base formulation was then mixed with varying amounts of Witconic TM 1298 (DBSA) and the resulting blends (Examples 5-8) were added to an ULSD fuel (obtained from ExxonMobil Corporation) at 450 ppm.
• DBSA Witconic TM 1298
• Example 5-8 the initial conductivity imparted to the fuel was measured immediately after blending the components (Column A). Additional blends were also stored at 90°C for 16 hours as described above. After aging, these blends were added to the ExxonMobil ULSD fuel and the fuel's conductivity was again measured (Column B), The results are shown in Table 3. Table 3.

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• Organic Chemistry (AREA)
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• 2007
  • 2007-09-25 US US11/860,664 patent/US20090077869A1/en not_active Abandoned
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