US20040088909A1 - Fuel compositions with diethyl succinate and method of use thereof - Google Patents

Fuel compositions with diethyl succinate and method of use thereof Download PDF

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Publication number
US20040088909A1
US20040088909A1 US10/292,123 US29212302A US2004088909A1 US 20040088909 A1 US20040088909 A1 US 20040088909A1 US 29212302 A US29212302 A US 29212302A US 2004088909 A1 US2004088909 A1 US 2004088909A1
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fuel
diethyl succinate
diesel
composition
percent
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US10/292,123
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Kris Berglund
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/02Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/02Use of additives to fuels or fires for particular purposes for reducing smoke development

Definitions

  • the present invention relates to fuel compositions containing diethyl succinate as a primary additive to oxygenate the fuel and reduce particulate emissions.
  • the present invention relates to diesel fuel compositions.
  • Diesel fuels are a significant contribution to pollution. This is shown by U.S. News & World Report for Nov. 4, 2002, page 63. The problem then is to reduce the particulates from diesel fuels.
  • Methanol and ethanol are excellent gasoline additives, but are not miscible with diesel fuel and emulsifiers and ignition improvers need to be added which increase the cost. Methanol is also both more toxic and corrosive than ethanol. Rapeseed methylesters (biodiesel) are of significant interest because they are non-toxic and with small engine modifications they can be used in existing diesel motors.
  • DME dimethyl ether
  • Natural gas can on a long-term perspective be a cost effective alternative to diesel, but natural gas is a fossil fuel and therefore not a renewable resource based alternative.
  • the present invention relates to a composition which comprises: a liquid hydrocarbon fuel; and between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source for the fuel.
  • the fuel is preferably diesel fuel; however, it could be gasoline or other alternative hydrocarbon fuels.
  • the diethyl succinate is preferably 5 to 10 percent by weight of the fuel.
  • the fuel is preferably substantially free of contaminants which cause pollution.
  • the composition preferably contains only the diethyl succinate as the additive.
  • the present invention also relates to a method for increasing combustion in an internal combustion engine of a fuel to water and carbon dioxide, and reducing particulates from the combustion, which comprises: providing a composition which comprises: a liquid hydrocarbon as the fuel and between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source to run the engine so as to increase the combustion and reduce the particulates from the combustion.
  • the term “primary” is intended to mean more than 50% and preferably more than 80% of the oxgenation source for the fuel is diethyl succinate.
  • FIG. 1 is a distribution graph showing concentration of particles versus diameter without diethyl succinate.
  • FIG. 2 is a distribution graph showing concentration of particles versus diameter with 5 percent by weight diethyl succinate.
  • DES Diethyl succinate
  • MK 1 Diethyl succinate
  • FIG. 2 also shows the displacement in the particle size distribution by addition of DES to MK 1 , from accumulation (larger particle) mode to a significantly increased amount in nuclei (fine particles) mode).
  • the total concentrate of particles was 72.2 ( ⁇ g/m 3 ) with blending of 5% diethyl succinate in MK 1 with 1100 rpm and 10% of maximum load.

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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)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

Fuel compositions comprising primarily diethyl succinate as an oxygenation additive are described. The fuels can be diesel fuels which generate carbon based particulates in diesel engines. The result is reduced emissions of particulates from the diesel engines.

Description

    BACKGROUND OF THE INVENTION
  • (1) Field of the Invention [0001]
  • The present invention relates to fuel compositions containing diethyl succinate as a primary additive to oxygenate the fuel and reduce particulate emissions. In particular, the present invention relates to diesel fuel compositions. [0002]
  • (2) Description of Related Art [0003]
  • Diesel fuels are a significant contribution to pollution. This is shown by U.S. News & World Report for Nov. 4, 2002, page 63. The problem then is to reduce the particulates from diesel fuels. [0004]
  • In a number of studies the correlation between properties of diesel fuels and emission has been investigated. Most of current additive candidates are ethers, esters or alcohols, but even glycols, carbonates and acetates have been considered. In 1995 Kazushi Tsurutani et al (SAE Paper 952349) examined 11 different oxygenates demonstrated that oxygenates considerably reduce the amount of particles (PM), measured in g/k Wh, but that the effect on NOX was nonexistent or very small. The observed effect was more related to the total oxygen content in the fuel after the additive was combined with the fuel, rather than the structure of the molecule. Noboru Miyamoto et al (SAE Paper 962115 (1996)) showed that the reduction of smoke and particle emissions were proportional (linear) to the oxygen concentration in the fuel despite the additive. A general conclusion would be that all oxygenates reduce smoke and particle emission without influencing NOX, a certain reduction of total carbon (THC) and CO was also seen. [0005]
  • Matthew Stoner and Thomas Litzinger (SAE Paper 1999-01-1475 (1999)) conducted a test to see how structure and boiling point of maleated glycol ethers affects the emissions. They suspected a connection between molecular structure and the amount of the reduced particle amount. They found that both kinds of oxygenate reduce emission of NOX and soot, but the maleates seems more effective. The maleates also reduced emissions of NOX because a delay of SOC (Start of Combustion). No connection between boiling point and effects on the emission could be detected. In a later study it was shown again that the molecule structure has an influence on the reduction of soot emissions. It was also confirmed that the ignition delay increased slightly and hence the NOX emission was reduced. [0006]
  • Methanol and ethanol are excellent gasoline additives, but are not miscible with diesel fuel and emulsifiers and ignition improvers need to be added which increase the cost. Methanol is also both more toxic and corrosive than ethanol. Rapeseed methylesters (biodiesel) are of significant interest because they are non-toxic and with small engine modifications they can be used in existing diesel motors. [0007]
  • A number of alternative fuels that are advocated today have disadvantages because they are expensive. DME (dimethyl ether) has for example good emission properties, works well in a converted diesel motor and is easy to ignite and is a gas non-miscible with diesel fuel. [0008]
  • Natural gas can on a long-term perspective be a cost effective alternative to diesel, but natural gas is a fossil fuel and therefore not a renewable resource based alternative. [0009]
  • Relevant patents are U.S. Pat. Nos. 5,268,008 to Kanne; 5,752,989 to Henly et al; 6,458,173 B1 to Lin and U.S. Pat. No. 6,468,319 B1 to Yeh et al. The trend of the patent art is towards high molecular weight additives having a molecular weight greater than or equal to 200, presumably to obtain the necessary solubility and reduced volatility in diesel or other fuels. There is a need for a less expensive additive for internal combustion engines which is readily available and which in particular can be produced from “green” or natural source precursor compounds. To summarize, it can be concluded that there still is a need to find the optimal additive for internal combustion engine fuels. [0010]
  • OBJECTS
  • It is therefore an object of the present invention to provide novel internal combustion engine fuel compositions incorporating a low molecular weight additive which is miscible with the fuel. Further, it is an object of the present invention to provide compositions which are easily prepared, are economical and can be prepared from natural source precursor compounds. These and other objects will become increasingly apparent by reference to the following description and the drawings. [0011]
  • SUMMARY OF THE INVENTION
  • The present invention relates to a composition which comprises: a liquid hydrocarbon fuel; and between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source for the fuel. The fuel is preferably diesel fuel; however, it could be gasoline or other alternative hydrocarbon fuels. The diethyl succinate is preferably 5 to 10 percent by weight of the fuel. The fuel is preferably substantially free of contaminants which cause pollution. The composition preferably contains only the diethyl succinate as the additive. [0012]
  • The present invention also relates to a method for increasing combustion in an internal combustion engine of a fuel to water and carbon dioxide, and reducing particulates from the combustion, which comprises: providing a composition which comprises: a liquid hydrocarbon as the fuel and between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source to run the engine so as to increase the combustion and reduce the particulates from the combustion. [0013]
  • The term “primary” is intended to mean more than 50% and preferably more than 80% of the oxgenation source for the fuel is diethyl succinate. [0014]
  • BRIEF DESCRIPTION OF DRAWINGS
  • FIG. 1 is a distribution graph showing concentration of particles versus diameter without diethyl succinate. [0015]
  • FIG. 2 is a distribution graph showing concentration of particles versus diameter with 5 percent by weight diethyl succinate.[0016]
  • DESCRIPTION OF PREFERRED EMBODIMENTS
  • U.S. Pat. No. 6,468,319 B1 which is incorporated by reference contains a detailed description of the various oxygenation secondary additives which can be used with diethyl succinate as well as a discussion of the art of testing oxygenates. The other patents discussed previously are also incorporated by reference showing secondary oxygenation additives. [0017]
  • EXAMPLE 1
  • Diethyl succinate (DES) was tested as an additive in diesel fuel. DES fulfils properties that are required for an additive: renewable, non-toxic, inexpensive and miscible with diesel fuel. The tests were performed and show a 20% reduction of the particle emission, using 5% DES in MK [0018] 1, as shown by comparison of FIG. 1 with FIG. 2. FIG. 2 also shows the displacement in the particle size distribution by addition of DES to MK 1, from accumulation (larger particle) mode to a significantly increased amount in nuclei (fine particles) mode). In FIG. 1, the total concentrates particles 85.1 (μg/m3) in MK 1 with 1100 rpm and 10% of maximum load. In FIG. 2, the total concentrate of particles was 72.2 (μg/m3) with blending of 5% diethyl succinate in MK 1 with 1100 rpm and 10% of maximum load.
  • There are numerous published sources of diesel fuel compositions. One is shown at lubrizol.com/ReadyReference. The present invention can reduce particulates in any of the diesel fuels sold worldwide in the same manner as Example 1. [0019]
  • It is intended that the foregoing description be only illustrative of the present invention and that the present invention be limited only by the hereinafter appended claims. [0020]

Claims (10)

I claim:
1. A composition which comprises:
(a) a liquid hydrocarbon fuel; and
(b) between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source for the fuel.
2. The composition of claim 1 wherein the fuel is diesel fuel.
3. The composition of claim 1 wherein the diethyl succinate is 5 to 10 percent by weight of the fuel.
4. The composition of any one of claims 1, 2 or 3 wherein the fuel is substantially free of contaminants which cause pollution.
5. A method for increasing combustion of a fuel to water and carbon dioxide, and reducing particulates from the combustion, which comprises:
providing a composition which comprises a liquid hydrocarbon as the fuel and between 0.1 and 30 percent by weight of diethyl succinate as a primary organic oxygenation source to run the engine so as to increase the combustion and reduce the particulates from the combustion.
6. The method of claim 5 wherein the fuel is diesel fuel.
7. The method of claim 5 wherein the diesel fuel is 5 to 10 percent by weight of the fuel.
8. The method of any one of claims 5, 6 or 7 wherein the fuel is substantially free of contaminants which cause pollution.
9. The composition of any one of claims 1, 2 or 3 wherein the diethyl succinate is the sole organic oxygenation source for the fuel.
10. The method of any one of clams 5, 6 or 7 wherein the diethyl succinate is the sole organic oxygenation source for the fuel.
US10/292,123 2002-11-12 2002-11-12 Fuel compositions with diethyl succinate and method of use thereof Abandoned US20040088909A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008043086A2 (en) * 2006-10-06 2008-04-10 Diversified Natural Products, Inc. Fuel compositions and methods
US20090090048A1 (en) * 2007-10-05 2009-04-09 Board Of Trustees Of Michigan State University Fuel compositions with mono- or di- butyl succinate and method of use thereof
US20110203165A1 (en) * 2008-12-23 2011-08-25 Chevron U.S.A. Inc. Enhanced biodiesel fuel having improved low-temperature properties and methods of making same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879176A (en) * 1970-12-11 1975-04-22 Nippon Oil Co Ltd Liquefied petroleum gas compositions
US5268008A (en) * 1982-12-27 1993-12-07 Union Oil Company Of California Hydrocarbon fuel composition
US5752989A (en) * 1996-11-21 1998-05-19 Ethyl Corporation Diesel fuel and dispersant compositions and methods for making and using same
US20020023384A1 (en) * 2000-08-04 2002-02-28 Yoshiro Hamada Low pollution fuel
US6458173B1 (en) * 1998-12-04 2002-10-01 Infineum International Ltd. Fuel additive and fuel composition containing the same
US6468319B1 (en) * 1999-07-16 2002-10-22 Exxonmobil Research And Engineering Co. Diesel fuel containing ester to reduce emissions
US6468318B1 (en) * 2000-01-25 2002-10-22 Delphi Technologies, Inc. Case partition design for continuous plate strap batteries
US6783561B2 (en) * 2000-12-21 2004-08-31 The University Of Chicago Method to improve lubricity of low-sulfur diesel and gasoline fuels

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879176A (en) * 1970-12-11 1975-04-22 Nippon Oil Co Ltd Liquefied petroleum gas compositions
US5268008A (en) * 1982-12-27 1993-12-07 Union Oil Company Of California Hydrocarbon fuel composition
US5752989A (en) * 1996-11-21 1998-05-19 Ethyl Corporation Diesel fuel and dispersant compositions and methods for making and using same
US6458173B1 (en) * 1998-12-04 2002-10-01 Infineum International Ltd. Fuel additive and fuel composition containing the same
US6468319B1 (en) * 1999-07-16 2002-10-22 Exxonmobil Research And Engineering Co. Diesel fuel containing ester to reduce emissions
US6468318B1 (en) * 2000-01-25 2002-10-22 Delphi Technologies, Inc. Case partition design for continuous plate strap batteries
US20020023384A1 (en) * 2000-08-04 2002-02-28 Yoshiro Hamada Low pollution fuel
US6783561B2 (en) * 2000-12-21 2004-08-31 The University Of Chicago Method to improve lubricity of low-sulfur diesel and gasoline fuels

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008043086A2 (en) * 2006-10-06 2008-04-10 Diversified Natural Products, Inc. Fuel compositions and methods
WO2008043086A3 (en) * 2006-10-06 2008-06-12 Diversified Natural Products I Fuel compositions and methods
US20090090048A1 (en) * 2007-10-05 2009-04-09 Board Of Trustees Of Michigan State University Fuel compositions with mono- or di- butyl succinate and method of use thereof
US20110203165A1 (en) * 2008-12-23 2011-08-25 Chevron U.S.A. Inc. Enhanced biodiesel fuel having improved low-temperature properties and methods of making same
US8147567B2 (en) * 2008-12-23 2012-04-03 Chevron U.S.A. Inc. Enhanced biodiesel fuel having improved low-temperature properties and methods of making same

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