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WO2015049184A1 - A methanol-based diesel fuel and the use of an ignition improver - Google Patents

A methanol-based diesel fuel and the use of an ignition improver Download PDF

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Publication number
WO2015049184A1
WO2015049184A1 PCT/EP2014/070719 EP2014070719W WO2015049184A1 WO 2015049184 A1 WO2015049184 A1 WO 2015049184A1 EP 2014070719 W EP2014070719 W EP 2014070719W WO 2015049184 A1 WO2015049184 A1 WO 2015049184A1
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Prior art keywords
methanol
fuel
ignition
fuel according
diesel fuel
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PCT/EP2014/070719
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French (fr)
Inventor
Anna Lif
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Nouryon Chemicals International BV
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Akzo Nobel Chemicals International BV
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - 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 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
    • C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane number
    • 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
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine

Definitions

  • the present invention relates to a methanol-based diesel fuel, comprising an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol.
  • Methanol is a candidate for use as an alternative fuel in internal combustion engines, such as diesel engines.
  • internal combustion engines such as diesel engines.
  • methanol a so-called ignition improver, i.e. an agent which serves to lower the ignition temperature of the fuel, is added to the methanol.
  • a diesel fuel in general is any liquid fuel suitable for use in diesel engines.
  • the ignition quality of a diesel fuel is expressed in terms of cetane number (CN).
  • the cetane number denotes the percentage by volume of cetane (hexadecane) in a combustible mixture containing cetane and 1 -methylnaphthalene, whose ignition delay match those of the diesel fuel being tested. Ignition delay is the time period between the start of injection and start of combustion (ignition) of the fuel. The higher the cetane number, the shorter is the ignition delay.
  • the cetane number of pure methanol is too low to enable it to be used as a diesel fuel, but the addition of an ignition improver will result in a mixture having a higher cetane number.
  • US 4,298,352 relates to a diesel fuel based on methanol and containing an additive for improving cetane number comprising a methanol-soluble polyoxyalkylene compound containing in total from 4 to 400 units derived from alkylene oxide.
  • US 5,659,335 relates to alcoholic fuel mixtures for operation of diesel engines, comprising an ignition improver based on nitrocellulose and a polyether with at least three ethylene oxide units.
  • an ignition improver based on nitrocellulose and a polyether with at least three ethylene oxide units.
  • a methanol soluble alkylene oxide adduct of glycerol is an excellent ignition improver for a methanol-based diesel fuel.
  • the present invention relates to a methanol-based diesel fuel comprising an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol.
  • the alkylene oxide is preferably selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
  • the alkylene oxide adduct is optionally end-capped, e.g. by a CrC 4 -alkyl group.
  • the alkoxylated glycerol may have the formula
  • Z -(CH 2 CH(CH 3 )0) m i(CH 2 CH 2 0) n (CH 2 CH(CH 3 )0) m2 T, where T is H or a C C 4 alkyl group, ml and m2 is independently a number 0-4, preferably ml and/or m2 is 0, and n is a number from 2, preferably from 5, more preferably from 6, to 20 preferably to 15, more preferably to 10; and preferably the sum of all n is 10-30, more preferably 15 to 25.
  • the present invention relates to the use of the above-defined methanol-soluble alkylene oxide adduct of glycerol according to formula (I), as an ignition improver for a methanol-based diesel fuel.
  • the invention in a third aspect relates to a process for operating a diesel engine, which comprises running the engine on a methanol-based diesel fuel containing the above-defined methanol-soluble alkylene oxide adduct of glycerol according to formula (I).
  • alkoxylated products according to formula (I) may be made by processes well-known in the art, by reacting glycerol with ethylene oxide, or propylene oxide and ethylene oxide, in the presence of a suitable catalyst. If both propylene oxide and ethylene oxide are used, the alkoxides may be added as blocks in either order, or may be added randomly. The products obtained from reaction with only ethylene oxide are the most preferred.
  • methanol soluble is meant a solubility in methanol at 20 °C of at least 0.1 , preferably at least 0.5% by weight.
  • methanol-based fuel is meant a fuel containing at least 50, preferably at least 60, more preferably at least 70, even more preferably at least 80, still more preferably at least 85 and most preferably at least 90% by weight of methanol.
  • the fuel may also contain other alcohols, such as ethanol and butanol.
  • the methanol-based diesel fuel preferably comprises
  • the methanol-based diesel fuel may further contain minor amounts of other additives, for example lubricants, such as fatty amine ethoxylates, fatty acid esters and fatty acid amides, corrosion inhibitors, such as morpholine and imidazolines, and other common additives used in fuel compositions.
  • the fuel may contain minor amounts of water, but is preferably essentially anhydrous, containing less than 1 % by weight of water.
  • the fuel is further preferably free, or essentially free, from nitrocellulose.
  • the ignition delay was tested by use of an Advanced Fuel Ignition Delay Analyzer (AFIDA) from the company ASG, in Neusass, Germany.
  • the measurement conditions were a chamber temperature of 700 °C and a pressure of 20 bar.
  • the injection pressure was 1000 bar and the injection period 1200 s.
  • the high pressure pump generates the injection pressure, while the heating tube keeps the fuel at a constant temperature.
  • the atomized fuel ignites spontaneously and leads to a pressure increase in the combustion chamber.
  • the pressure variation high resolution curve is recorded by a dynamic pressure sensor.
  • the ignition delay values obtained are collected in Table 1 below.
  • Samples for test in the AFIDA equipment were prepared by blending ignition improver with methanol at the required concentrations.
  • the ignition improvers were easily dissolved in methanol at room temperature.
  • the ignition improvers according to the invention exhibited a much better effect than the comparison PEG 600, since a larger amount of the latter was needed to obtain about the same ignition delay as the former.
  • Another test was made according to the procedure above, except that the chamber temperature was 720 °C and the pressure 35 bar.

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

Abstract

The present invention relates to a methanol-based diesel fuel, comprising an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol.

Description

A METHANOL-BASED DIESEL FUEL AND THE USE OF AN IGNITION
IMPROVER
Technical Field of Invention
The present invention relates to a methanol-based diesel fuel, comprising an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol.
Technical Background of the Invention
Methanol is a candidate for use as an alternative fuel in internal combustion engines, such as diesel engines. However, because of the high ignition temperature of methanol, it is not possible to use pure methanol as a fuel in a conventional diesel engine. For these engines a so-called ignition improver, i.e. an agent which serves to lower the ignition temperature of the fuel, is added to the methanol.
A diesel fuel in general is any liquid fuel suitable for use in diesel engines. The ignition quality of a diesel fuel is expressed in terms of cetane number (CN). The cetane number denotes the percentage by volume of cetane (hexadecane) in a combustible mixture containing cetane and 1 -methylnaphthalene, whose ignition delay match those of the diesel fuel being tested. Ignition delay is the time period between the start of injection and start of combustion (ignition) of the fuel. The higher the cetane number, the shorter is the ignition delay. The cetane number of pure methanol is too low to enable it to be used as a diesel fuel, but the addition of an ignition improver will result in a mixture having a higher cetane number. Thus, for the mixture the ignition delay time will be shorter than it is for pure methanol. US 4,298,352 relates to a diesel fuel based on methanol and containing an additive for improving cetane number comprising a methanol-soluble polyoxyalkylene compound containing in total from 4 to 400 units derived from alkylene oxide.
US 5,659,335 relates to alcoholic fuel mixtures for operation of diesel engines, comprising an ignition improver based on nitrocellulose and a polyether with at least three ethylene oxide units. However, there is still a need in the art for ignition improvers with increased efficacy, for example such which further shortens the ignition delay time and/or can be used in lower concentrations. Summary of the Invention
It is an object of the present invention to provide an ignition improver for use in a methanol-based diesel fuel, which at least partly meets the need in the art. Now it has surprisingly been found that a methanol soluble alkylene oxide adduct of glycerol is an excellent ignition improver for a methanol-based diesel fuel.
Detailed Description of the Invention
In a first aspect, the present invention relates to a methanol-based diesel fuel comprising an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol. The alkylene oxide is preferably selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof. The alkylene oxide adduct is optionally end-capped, e.g. by a CrC4-alkyl group.
The alkoxylated glycerol may have the formula
Figure imgf000003_0001
where Z= -(CH2CH(CH3)0)mi(CH2CH20)n (CH2CH(CH3)0)m2T, where T is H or a C C4 alkyl group, ml and m2 is independently a number 0-4, preferably ml and/or m2 is 0, and n is a number from 2, preferably from 5, more preferably from 6, to 20 preferably to 15, more preferably to 10; and preferably the sum of all n is 10-30, more preferably 15 to 25.
In a second aspect, the present invention relates to the use of the above-defined methanol-soluble alkylene oxide adduct of glycerol according to formula (I), as an ignition improver for a methanol-based diesel fuel.
In a third aspect the invention relates to a process for operating a diesel engine, which comprises running the engine on a methanol-based diesel fuel containing the above-defined methanol-soluble alkylene oxide adduct of glycerol according to formula (I).
The above-mentioned alkoxylated products according to formula (I) may be made by processes well-known in the art, by reacting glycerol with ethylene oxide, or propylene oxide and ethylene oxide, in the presence of a suitable catalyst. If both propylene oxide and ethylene oxide are used, the alkoxides may be added as blocks in either order, or may be added randomly. The products obtained from reaction with only ethylene oxide are the most preferred.
Within the context of the present invention the expression "methanol soluble" is meant a solubility in methanol at 20 °C of at least 0.1 , preferably at least 0.5% by weight. Within the context of the present invention the expression "methanol-based fuel" is meant a fuel containing at least 50, preferably at least 60, more preferably at least 70, even more preferably at least 80, still more preferably at least 85 and most preferably at least 90% by weight of methanol. The fuel may also contain other alcohols, such as ethanol and butanol.
The methanol-based diesel fuel preferably comprises
a) at least 50, preferably at least 60, more preferably at least 70, even more preferably at least 80, still more preferably at least 85 and most preferably at least 90% by weight, based on the total weight of the fuel, of methanol; and
b) 0.1 -10, preferably 0.5-10% by weight, based on the total weight of the fuel, of the methanol-soluble alkylene oxide adduct of glycerol according to formula (I). The methanol-based diesel fuel may further contain minor amounts of other additives, for example lubricants, such as fatty amine ethoxylates, fatty acid esters and fatty acid amides, corrosion inhibitors, such as morpholine and imidazolines, and other common additives used in fuel compositions. The fuel may contain minor amounts of water, but is preferably essentially anhydrous, containing less than 1 % by weight of water. The fuel is further preferably free, or essentially free, from nitrocellulose.
The present invention is further illustrated by the following examples.
EXAMPLES
Test of ignition delay
The ignition delay was tested by use of an Advanced Fuel Ignition Delay Analyzer (AFIDA) from the company ASG, in Neusass, Germany. The measurement conditions were a chamber temperature of 700 °C and a pressure of 20 bar. The injection pressure was 1000 bar and the injection period 1200 s. The high pressure pump generates the injection pressure, while the heating tube keeps the fuel at a constant temperature. The atomized fuel ignites spontaneously and leads to a pressure increase in the combustion chamber. The pressure variation high resolution curve is recorded by a dynamic pressure sensor. The ignition delay values obtained are collected in Table 1 below.
Sample preparation
Samples for test in the AFIDA equipment were prepared by blending ignition improver with methanol at the required concentrations. The ignition improvers were easily dissolved in methanol at room temperature.
Table 1
Figure imgf000005_0001
The ignition improvers according to the invention exhibited a much better effect than the comparison PEG 600, since a larger amount of the latter was needed to obtain about the same ignition delay as the former. Another test was made according to the procedure above, except that the chamber temperature was 720 °C and the pressure 35 bar.
Table 2
Figure imgf000006_0001
1TMP = trimethylol propane

Claims

A methanol-based diesel fuel comprising at least 50% by weight, based on the total weight of the fuel, of methanol, and an ignition improver that is a methanol soluble alkylene oxide adduct of glycerol.
2. A fuel according to claim 1 , where the alkylene oxide is selected from the group consisting of ethylene oxide and propylene oxide and mixtures thereof.
3. A fuel according to claim 1 or 2, where the ignition improver has the formula
Figure imgf000007_0001
where Z= -(CH2CH(CH3)0)mi(CH2CH20)n(CH2CH(CH3)0)m2T, where T is H or a C1-C4 alkyl group, ml and m2 is independently a number 0-4 and n is a number 2-20.
4. A fuel according to claim 3, wherein n is a number 5-15.
5. A fuel according to claim 3, wherein the sum of all n is 10-30.
6. A fuel according to claim 3, wherein the sum of all n is 15-25.
7. A fuel according to any one of the claims 1 -6, comprising
a) at least 50% by weight, based on the total weight of the fuel, of methanol b) 0.1 -10% by weight, based on the total weight of the fuel, of the methanol- soluble alkylene oxide adduct of glycerol.
8. A fuel according to any one of the preceding claims, further comprising at least one lubricant and at least one corrosion inhibitor.
9. A fuel according any one of the preceding claims, being essentially
anhydrous.
10. A fuel according to any one of the preceding claims, being essentially free from nitrocellulose.
1 1 . Use of a methanol soluble alkylene oxide adduct glycerol as an ignition improver for a methanol-based diesel fuel.
12. Use according to claim 1 1 , where the alkoxylated polyol has formula (I) as defined in any one of the claims 3 to 6.
13. A method for operating a diesel engine, which comprises running the engine on a methanol-based diesel fuel according to any one of the claims 1 to 10.
PCT/EP2014/070719 2013-10-01 2014-09-29 A methanol-based diesel fuel and the use of an ignition improver Ceased WO2015049184A1 (en)

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EP13186883.8 2013-10-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112920864A (en) * 2021-02-07 2021-06-08 深圳蓝诺清洁能源科技有限公司 Alcohol-based liquid fuel and preparation method thereof
WO2021250210A1 (en) 2020-06-10 2021-12-16 Sasol Chemicals Gmbh Aqueous composition comprising water-soluble glycerin-based polyalkylene glycols and use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298352A (en) 1977-11-29 1981-11-03 Berol Kemi Ab Diesel fuel comprising methanol and a methanol-soluble polyoxyalkylene compound
US4659335A (en) * 1984-03-31 1987-04-21 Bayer Aktiengesellschaft Ignition improvers for fuel mixtures
WO1995005437A1 (en) * 1993-08-19 1995-02-23 Akzo Nobel Surface Chemistry Ab An ethanol fuel and the use of an ignition improver
US5659335A (en) 1994-11-14 1997-08-19 Lucent Technologies Inc. Computing interface system

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298352A (en) 1977-11-29 1981-11-03 Berol Kemi Ab Diesel fuel comprising methanol and a methanol-soluble polyoxyalkylene compound
US4659335A (en) * 1984-03-31 1987-04-21 Bayer Aktiengesellschaft Ignition improvers for fuel mixtures
WO1995005437A1 (en) * 1993-08-19 1995-02-23 Akzo Nobel Surface Chemistry Ab An ethanol fuel and the use of an ignition improver
US5659335A (en) 1994-11-14 1997-08-19 Lucent Technologies Inc. Computing interface system

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021250210A1 (en) 2020-06-10 2021-12-16 Sasol Chemicals Gmbh Aqueous composition comprising water-soluble glycerin-based polyalkylene glycols and use thereof
JP2023528951A (en) * 2020-06-10 2023-07-06 サソール ケミカルズ ゲーエムベーハー Water-soluble composition containing water-soluble glycerin-based polyalkylene glycol and use of the composition
US20230235244A1 (en) * 2020-06-10 2023-07-27 Sasol Chemicals Gmbh Aqueous Composition Comprising Water-Soluble Glycerin-Based Polyalkylene Glycols and Use Thereof
US12049600B2 (en) 2020-06-10 2024-07-30 Sasol Chemicals Gmbh Aqueous composition comprising water-soluble glycerin-based polyalkylene glycols and use thereof
CN112920864A (en) * 2021-02-07 2021-06-08 深圳蓝诺清洁能源科技有限公司 Alcohol-based liquid fuel and preparation method thereof

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