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
  • C10L1/222—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1608—Well defined compounds, e.g. hexane, benzene
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
• • 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
  • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• • 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
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
  • 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 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
  • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development

Definitions

• the present invention relates to the use of a composition for reducing the emissions of exhaust pollutants, in particular nitrogen oxides, from a combustion engine fitted for example with a motor vehicle, a ship, an aircraft or a generator.
• a combustion engine fitted for example with a motor vehicle, a ship, an aircraft or a generator.
• Liquid fuels and fuels are used in many fields, such as aeronautics, automobiles, marine vessels, and heating.
• a liquid fuel is a liquid compound capable of uniting with an oxidant (almost always the dioxygen of air) and capable of burning like LPG, FOD, heavy fuel oil and assimilated products; while a fuel is a fuel that feeds an internal combustion engine.
• a fuel or liquid fuel may be a mixture of several hundred hydrocarbons. These can be derived from the refining of crude oil of fossil origin or can be synthesized according to the Fischer-Tropsch process from fossil carbon (coal, gas) or biomass.
• the fuels are indeed in general mixtures of hydrocarbons: for gasoline, one can count about 20 to 30% of alkanes of formula CnH 2n + 2 , 5% of cycloalkanes, 30 to 45% of alkenes and at 45% aromatics Vegetable oils or fatty acid methyl esters (FAMEs) may be added to these compounds
• fuel be it gasoline, diesel, compressed natural gas (CNG or LNG) or LPG
• hydrocarbons can be simple small molecules such as methane, the main component of natural gas, or large complex molecules. During combustion, these molecules fragment. Ideally, they decompose completely in C0 2 and water vapor, but some escape unchanged or partially degraded in the form of hydrocarbons (HC) or carbon monoxide (CO).
• HC hydrocarbons
• CO carbon monoxide
• PM particulate matter
• PM consists mainly of soot particles with volatile hydrocarbons and some sulphate and metal residues from fuel and engine lubricants.
• the other main pollutant present in the exhaust gas results from the fact that the fuel is burned with air, which is composed of 80% nitrogen, not with pure oxygen. At high temperature, nitrogen forms nitrogen oxides (NO x ) in the combustion chamber. The more efficient the combustion, the higher the temperatures will be, resulting in higher emissions of NO x .
• gas oil naturally contains several components that increase emissions of particles and nitrogen oxides (NO x). This is sulfur and aromatic hydrocarbons (PAHs).
• NO x nitrogen oxides
• PAHs sulfur and aromatic hydrocarbons
• Euro emission standards are implemented on off-schedule dates for cars, light commercial vehicles, motorcycles and trucks.
• the standards differ between the different types of engines (spark ignition engines (petrol, LPG ...) or diesel engines) and vehicles, even in the selected units, compared to the distance traveled (for example g / km), except for heavy vehicles where they are related to the developed energy (eg g / kWh).
• the NEDC (New European Driving Cycle) driving cycle, set up in 1973, will be replaced in 2014 at the latest, under the Euro 6 standard, by the WLTC (Harmonized Worldwide Test Procedure for passenger cars and light commercial vehicles), designed to be as close as possible to actual operating conditions.
• the maximum nitrogen oxide emission standards are 80 mg / km for a diesel vehicle and 60 mg / km for a gasoline or LNG / LPG powered vehicle. These pollutant emissions are measured during a standard NEDC driving cycle that lasts 20 minutes. It includes a first phase of driving typified "city” followed by a faster driving phase typified "road”. The average speed during this cycle is 33 km / h.
• EGR Exhaust Gas Recirculation
• Automotive catalysts, traps and filters built into a properly designed engine system can virtually eliminate all pollutant emissions under most driving conditions. Catalysts generally need to reach an adequate operating temperature, but with modern systems this can be achieved in a few seconds.
• the object of the present invention is to propose a new additive composition which avoids, at least in part, the aforementioned drawbacks.
• the present invention relates to the use of an additive composition for reducing nitrogen oxide (NO x ) emissions, such as nitrous oxide emissions, emitted during the combustion of a fuel. or a fuel, for example by a combustion heat engine, said composition comprising, by weight, relative to the total weight of said composition, from 5 to 95% of a mixture of at least a first and a second fatty diamine, said diamines being different, and from 5 to 95% of at least one solvent.
• NO x nitrogen oxide
• FIG. 1 represents the diagram of the actual driving speeds of the 60NERV driving cycle in time (seconds) as a function of the speed in km / h produced for the experimental tests.
• the present invention relates to the use of an additive composition to reduce emissions of nitrogen oxides (NO x emitted during the combustion of a fuel or a fuel, example by a combustion engine, said composition comprising, by weight, relative to the total weight of said composition, from 5 to 95% of a mixture of at least a first and a second fatty diamine, said diamines being different, and from 5 to 95% of at least one solvent.
• an additive composition to reduce emissions of nitrogen oxides (NO x emitted during the combustion of a fuel or a fuel, example by a combustion engine
• said composition comprising, by weight, relative to the total weight of said composition, from 5 to 95% of a mixture of at least a first and a second fatty diamine, said diamines being different, and from 5 to 95% of at least one solvent.
• the Applicant has surprisingly discovered that the use of an additive composition as described above makes it possible to reduce nitrogen oxide emissions, such as nitrous oxide (N 2 0) in the chambers. combustion of a machine (such as a generator, a boiler) or a combustion vehicle, such as a motor vehicle.
• nitrogen oxide emissions such as nitrous oxide (N 2 0) in the chambers. combustion of a machine (such as a generator, a boiler) or a combustion vehicle, such as a motor vehicle.
• the nitrogen oxides NO x are emissions comprising nitrogen monoxide NO, nitrogen dioxide NO 2 , nitrous oxide nitrous oxide N 2 0, dinitrogen pentoxide N 2 0 5, the dinitrogen tetroxide N 2 0 4, and dinitrogen trioxide N 2 0 3 or a mixture thereof.
• the additive composition according to the invention is generally poured directly into the tank of the machine, the combustion vehicle or into the tank of a service station.
• an amount of 0.01 to 10%, preferably 0.01 to 8% and even more preferably 0.01 to 3% by weight. volume of the additive composition relative to the total volume of the tank, is suitable for reducing nitrogen oxide emissions.
• said first and second diamines that are suitable for the present invention are chosen from a diamine comprising at least one saturated or unsaturated fatty acid radical comprising from 4 to 20, preferably from 8 to 18, carbon atoms, such that decyl radical, stearyl, oleyl, ricinoleyl, linoleyl, lauryl, myristyl, capryl and palmityl or a mixture of C 4 -C 2 O alkyl chains, preferably C 8 -C 8 chains, such as coconut, tallow or coconut chains; (Alkyl radical derived from coconut fatty acid, tallow or coconut).
• the first diamine corresponds to the following formula I:
• n 1 and 8
• R 26 , R 27 , R 28 and R 29 are independently of each other: hydrogen, a linear or branched C 1 -C 4 alkyl radical, or a linear or branched C 4 -C 30 alkyl radical; , preferably C 8 -C 2 o, provided that at least one of R 26, R 27, R 28 and R 29 is a linear or branched alkyl radical C 4 -C 30, preferably C 8 -C 20 .
• R 26 , R 27 , R 28 and R 29 carries the linear or branched C 4 -C 30 , preferably linear, C 8 -C 20 alkyl radical.
• R 26 , R 27 , R 28 and R 29 are hydrogen.
• C 3 o is chosen from: a decyl, stearyl, oleyl, ricinoleyl, linoleyl, lauryl, myristyl, capryl and palmityl radical or alkyl radical derived from coconut, tallow or coconut fatty acid (mixture of C 4 alkyl chains) -C 20, preferably C 8 -C 8).
• the first diamine is chosen from N-octyl-1,3-propylene diamine, N-decyl-1,3-propylene diamine, N-dodecyl-1,3-propylene diamine, N-tetradecyl-1,3-propylene diamine, N-octodecyl-1,3-propylene diamine, N-oleyl-1,3 propylene diamine, and N-alkyl 1,3 propylene diamine, the alkyl radical of which is derived from a coconut, tallow or coconut fatty acid, or a mixture thereof.
• N-oleyl-1,3-propylene diamine compound corresponds to the CAS number
• the first diamine is present in the additive composition at a content by weight, based on the total weight of the composition of 1 to 35%, preferably 8 to 22% and even more preferably 12 to 17%.
• the second diamine is a polyethoxylated alkyl diamine.
• a polyethoxylated alkyl diamine or a mixture of several polyethoxylated alkyl diamines suitable for the present invention is preferably a compound of formula II below:
• R is a C 3 -C 2 alkyl radical
• the alkyl radical has a molecular weight between 220 and 515 g / mol.
• the polyethoxylated alkyl diamine is at least one compound chosen from: N, N ', N'-tris (2-hydroxyethyl) -N-tallow-1, 3 propylene diamine; N, N ', N'-polyoxyethylene (25) -N-tallow-1,3 propylene diamine; N, N ', N'-polyoxyethylene (20) -N-tallow-1,3-propylene diamine; N, N ', N'-polyoxyethylene (15) -N-tallow-1, 3 propylene diamine; N, N ', N'-polyoxyethylene (12) -N-tallow-1,3-propylene diamine N, N', N'-polyoxyethylene (10) -N-tallow-1,3-propylene diamine, N, N ', N'-polyoxyethylene (7) -N-tallow-1,3-propylene diamine and N, N ', N'-polyoxyethylene (3) -
• the polyethoxylated alkyl diamine is at least one selected from: N, N ', N'-polyoxyethylene (25) -N-tallow-1,3 propylene diamine; N, N ', N'-polyoxyethylene (10) -N-tallow-1,3-propylene diamine, and N, ⁇ ', ⁇ '-polyoxyethylene (7) -N-tallow-1,3 propylene diamine, or one of their mixtures.
• the 7 mole compound of ethylene oxide (N, N ', N'-polyoxyethylene (7) -N-tallow-1, 3 propylene diamine) is preferred. It is liquid at ambient (25 ° C) and comprises about 3% C i4, 30% of C 6, 40% of C 5, 26% of C i8 and 1% of C 2 o It is known as a wetting, dispersing and emulsifying agent.
• the DINORAMOX ® S7 product of the company CECA Arkema GROUP is particularly suitable for the present composition.
• the second diamine is present in the additive composition at a content by weight, based on the total weight of the composition of 4 to 90%, preferably 55 to 85% and even more preferably 60 to 78%.
• the solvent that is suitable for the present invention is chosen from isopropylbenzene, gasoline, fuel oil, and kerosene, or a mixture thereof, preferably the solvent is chosen from isopropylbenzene and / or gasoline.
• the solvent suitable for the present invention is isopropylbenzene (CAS No. 98-82-8).
• the solvent is present in the additive composition at a content by weight, based on the total weight of the composition of 5 to 95%, preferably 7 to 25% and even more preferably 12 to 19%.
• the additive composition comprises, by weight, relative to the total weight of the emulsion:
• the emissions of nitrogen oxide emitted by a combustion engine operating with a fuel additive of the composition according to the invention are reduced by about 15% compared to a combustion engine in which the fuel does not contain the additive composition according to the invention as demonstrated in the experimental section below.
• the additive composition of the invention may be prepared according to the method described below.
• This process comprises the following steps:
• the reheating step i) is carried out at a temperature between 30 ° C and 50 ° C, preferably between 35 ° C and 45 ° C, and even more preferably at 40 ° C.
• stirring is between 20 rpm and 50 rpm during reheating i).
• reheating and stirring take place at least for 5 days.
• the solvent is isopropylbenzene, so that the emulsifying composition from step ii) is still liquid at temperatures between 0 ° C and 20 ° C.
• the present invention also relates to a method for reducing the nitrogen oxide emissions emitted by a combustion engine, said method comprising a step of adding to a fuel an additive composition comprising, by weight, with respect to total weight of said composition, from 5 to 95% of a mixture of at least a first and a second fatty diamine, said diamines being different, and from 5 to 95% of a solvent.
• Example 2 Composition of the Additive Composition According to the Invention Tested
• the additive composition comprises, by weight, relative to the total weight of the composition:
• the additive composition according to the invention has been prepared by:
• composition For the rest of the description, this composition will be called COMP 1.
• Example 2 Assessment of the influence of the additive composition of the invention on the emission of pollutants to the nitrogen oxide exhaust NO x (NO, N0 2 and N 2 0) was carried out on a Euro IV definition SCANIA heavy vehicle test vehicle, with a run of around 17000 km between the two configurations.
• Configuration B SCANIA R420 Euro IV operating with the same commercial type diesel oil additive 1/1000 with the additive composition according to the present invention (COMP 1), after a rolling of 17000 km.
• the test according to configuration B was carried out 15 minutes after the addition of the additive composition according to the invention in the gas oil.
• test program included:
• the measurements carried out concerned the emissions of regulated pollutants NO x and in particular NO + N0 2 and N 2 0, on a cycle of "60NERV" on the technical requirements laid down by Directives 72/306 / EEC and 2005/21 / EC .
• the analytical methods used are those imposed by the regulations in force, namely chemiluminescence analysis for NO x .
• the devices used are presented in ⁇ 2.2.1.
• the speed measurement is displayed on a digital indicator and is calculated from the distance and time indications.
• This driving guide allows the driver of the vehicle to follow the test cycle defined in Figure 1.
• the main information is:
• the gases were taken through a total flow dilution tunnel (POP sampling system).
• the nitrogen oxides NO x (NO + N0 2 and N 2 0) were on a TOPAZE 2010 analyzer (chemiluminescence type).
• the ambient air sample is analyzed on the same analyzer and on the same measurement ranges as those used for the sample of the diluted exhaust gas.
• Table 1 shows the NO x emissions (NO + N0 2 + N 2 0) on the "60NERV" cycle.
• Table 1 As illustrated in Table 1, the additive composition according to the invention makes it possible to reduce NO x oxide emissions emitted by a fuel oil fuel by 14.5% compared to a comparative diesel fuel not comprising the additive according to the invention.
• Table 2 shows N 2 O 2 nitroxide emissions on the "60 NERV" cycle.
• the additive composition according to the invention makes it possible to reduce the emissions of nitrogen oxides and in particular the nitrous oxide emissions, released into the atmosphere during of burning a fuel.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Combustion & Propulsion (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Solid Fuels And Fuel-Associated Substances (AREA)

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• 2014
  • 2014-02-05 EP EP14706893.6A patent/EP2954032A1/de not_active Withdrawn
  • 2014-02-05 WO PCT/FR2014/050219 patent/WO2014122399A1/fr not_active Ceased

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