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US20110296744A1 - Ethyl Acetate As Fuel Or Fuel Additive - Google Patents

Ethyl Acetate As Fuel Or Fuel Additive Download PDF

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Publication number
US20110296744A1
US20110296744A1 US12/792,867 US79286710A US2011296744A1 US 20110296744 A1 US20110296744 A1 US 20110296744A1 US 79286710 A US79286710 A US 79286710A US 2011296744 A1 US2011296744 A1 US 2011296744A1
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US
United States
Prior art keywords
fuel
application
diesel
ethyl acetate
blend
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US12/792,867
Inventor
Ray Jones
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Lurgi Inc
Original Assignee
Lurgi PSI Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lurgi PSI Inc filed Critical Lurgi PSI Inc
Priority to US12/792,867 priority Critical patent/US20110296744A1/en
Assigned to LURGI PSI, INC. reassignment LURGI PSI, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JONES, RAY
Assigned to Lurgi, Inc. reassignment Lurgi, Inc. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: LURGI PSI, INC.
Publication of US20110296744A1 publication Critical patent/US20110296744A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/02Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00Technologies for the production of fuel of non-fossil origin
    • Y02E50/10Biofuels, e.g. bio-diesel

Definitions

  • Ethyl Acetate has considerable potential as an oxygenated fuel additive.
  • the molecule has four carbons and excellent fuel properties.
  • Ethyl acetate can be readily produced from “Renewable” resources by several processes.
  • Ethyl acetate has low toxicity, a pleasant odor, and is not hygroscopic, as is ethanol.
  • Ethanol is the recognized fuel blend additive for petroleum gasoline
  • biodiesel blends of methyl esters
  • the present invention is a fuel blend consisting of a hydrocarbon-containing fuel component; and ethyl acetate.
  • the hydrocarbon-containing fuel component may be selected from the group consisting of gasoline, diesel, bioethanol and biodiesel.
  • the invention declared here is the use of Ethyl Acetate as a fuel, or fuel additive for motors burning conventional petroleum gasoline or gasoline blends, and also the use of Ethyl Acetate as a blending agent for Biodiesel fuels or as a blending agent to lower the cloud point of Biodiesel blending stock.
  • Ethyl Acetate appears to avoid the problems of ethanol's hygroscopic nature, while still being a desirable fuel, or fuel additive.
  • Ethyl acetate is described by the formula CH 3 COOCH 2 CH 3 .
  • Ethyl acetate is also known as ethyl ethanoate, ethyl ester, acetic ester, and ester of ethanol.
  • Ethyl acetate is in frequent use as a solvent, used in paint systems and for cleaning purposes. It is even used in some brands of finger nail polish remover. It has a pleasant sweet odor. It is normally a liquid at normal ambient temperatures with a boiling point of 171 degrees Fahrenheit.
  • Ethyl Acetate is known to be relatively non-toxic. It has even been used as a solvent to decaffeinate coffee beans. Compared to ethanol it is recognized generally to be “non-hygroscopic” in nature, allowing very limited water to mix in with the compound. This latter characteristic is important.
  • Ethyl acetate can be produced by any of several process methods.
  • Ethyl Acetate can be formed by the acid catalyzed esterification of acetic acid with ethanol.
  • Ethyl Acetate can be formed by the direct dehydrogenation of ethanol over a copper catalyst at elevated temperatures, producing hydrogen as a by-product.
  • Ethyl Acetate has been reported to be formed by the direct esterification or interesterification of acetic acid, where the acetic acid was produced from a biomass fermentation process.
  • Ethyl acetate when produced by one such process from biomass was the intermediate product that was then hydrogenated to ethanol as the final fuel additive product. It would appear that ethyl acetate in this type process would be cheaper than the ethanol produced from the same process.
  • a fuel blend consisting of: a hydrocarbon-containing fuel component; and ethyl acetate.
  • the hydrocarbon-containing fuel component may be gasoline or diesel.
  • the hydrocarbon-containing fuel component may also be petroleum gas, natural gas, liquefied petroleum gas, or propane.
  • the hydrocarbon-containing fuel component may also be bioethanol or biodiesel.
  • the ethyl acetate may be added to mixtures of diesel fuel and biodiesel to reduce the cloud point to improve winter operation performance of said mixtures.
  • the ethyl acetate may be added to biodiesel and mixtures of biodiesel to reduce the cloud point to improve winter operation and performance of said biodiesel or mixtures thereof.
  • the ethyl acetate may be added to diesel fuel, or mixtures of biodiesel and diesel fuel, or directly to biodiesel or mixtures of biodiesel to adjust the viscosity of said fuel mixtures.
  • the fuel blends may be used for any fuel blends.
  • the fuel blends may be used for any fuel blends.
  • a marine application such as jet skis, outboard motors and inboard motors
  • a recreational application such as snowmobiles, mopeds, and motorcycles
  • a residential application such as lawnmowers, string trimmers, and chain saws
  • the hydrocarbon-containing fuel component may be gasoline, diesel, petroleum gas, natural gas, liquefied petroleum gas, propane, bioethanol or biodiesel, or any combination thereof.
  • the fuel blend may comprise least 5% ethyl acetate by volume.
  • the fuel blend may comprise at least 8% ethyl acetate by volume.
  • the fuel blend may comprise at least 10% ethyl acetate by volume.
  • the ethyl acetate may be a biomass intermediate product in the ethanol production process.
  • the ethyl acetate may be formed by the acid catalyzed esterification of acetic acid with ethanol.
  • the ethyl acetate may be formed by the direct esterification of acetic acid.
  • the ethyl acetate may be formed by the inter-esterification of acetic acid.
  • the ethyl acetate may be formed by the dehydrogenation of ethanol.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

A fuel blend consisting of a hydrocarbon-containing fuel component; and ethyl acetate is provided. The hydrocarbon-containing fuel component may be gasoline, diesel, bioethanol or biodiesel.

Description

    BACKGROUND
  • Ethyl Acetate has considerable potential as an oxygenated fuel additive. The molecule has four carbons and excellent fuel properties. Ethyl acetate can be readily produced from “Renewable” resources by several processes. Ethyl acetate has low toxicity, a pleasant odor, and is not hygroscopic, as is ethanol.
  • In the realm of alternative or renewable hydrocarbon fuels, or fuel additives, two stand out as the current state of the art recognized fuel blending additives. Ethanol is the recognized fuel blend additive for petroleum gasoline, and biodiesel (blends of methyl esters) is the recognized fuel blend additive for petroleum diesel motor fuel.
  • Recent efforts in the field of new fuel substitutes or fuel additives have focused upon butanol or “bio-butanol” as a desired new four carbon oxygenated fuel component. It was discovered, by the inventor that Ethyl Acetate also has four carbons, and is a double oxygenated compound (having two oxygen atoms within the formula), and has desirable fuel characteristics.
  • One of the recognized drawbacks of ethanol as a petroleum gasoline blend additive is its hygroscopic nature, or desire to attract water. This has been a reported problem with ethanol for two major reasons.
  • First, where ethanol blends are used for marine motor applications, such as fishing boats or pleasure craft, boat owners have reported issues with “wet” fuel due to the ethanol blend attracting water from the naturally moist environs of marine craft. These “wet” fuels have caused motor starting difficulties, sudden motor stops, and corroding of motor parts requiring extra and more frequent maintenance.
  • Second, the tendency for ethanol to become “wet” due to its hygroscopic nature, has been the reason that ethanol blend stock is NOT transported through the normal fuel pipeline system. The wet ethanol causes excessive corrosion of the fuel pipelines causing maintenance due to deterioration and contamination of petroleum fuels by transported through the same pipeline, from the corrosion products of the pipeline with wet ethanol. Ethanol would require a stainless steel (more costly pipeline) and a completely separate pipeline system (which is cost prohibitive).
  • SUMMARY
  • The present invention is a fuel blend consisting of a hydrocarbon-containing fuel component; and ethyl acetate. The hydrocarbon-containing fuel component may be selected from the group consisting of gasoline, diesel, bioethanol and biodiesel.
  • DESCRIPTION OF PREFERRED EMBODIMENTS
  • The invention declared here is the use of Ethyl Acetate as a fuel, or fuel additive for motors burning conventional petroleum gasoline or gasoline blends, and also the use of Ethyl Acetate as a blending agent for Biodiesel fuels or as a blending agent to lower the cloud point of Biodiesel blending stock.
  • Ethyl Acetate appears to avoid the problems of ethanol's hygroscopic nature, while still being a desirable fuel, or fuel additive. Ethyl acetate, is described by the formula CH3COOCH2CH3. Ethyl acetate is also known as ethyl ethanoate, ethyl ester, acetic ester, and ester of ethanol.
  • Ethyl acetate is in frequent use as a solvent, used in paint systems and for cleaning purposes. It is even used in some brands of finger nail polish remover. It has a pleasant sweet odor. It is normally a liquid at normal ambient temperatures with a boiling point of 171 degrees Fahrenheit.
  • It has a low flash point, at negative 4 degrees Centigrade (or 25 degrees Fahrenheit), which makes it easy to ignite. Its freezing point is negative 118 degrees Fahrenheit which makes it an acceptable fuel additive for winter conditions. The heat of combustion of ethyl acetate is higher than for ethanol, and likely makes up some of the difference in combustion energy lost by mixtures of ethanol in gasoline.
  • Ethyl Acetate is known to be relatively non-toxic. It has even been used as a solvent to decaffeinate coffee beans. Compared to ethanol it is recognized generally to be “non-hygroscopic” in nature, allowing very limited water to mix in with the compound. This latter characteristic is important.
  • Ethyl acetate can be produced by any of several process methods.
  • 1. Ethyl Acetate can be formed by the acid catalyzed esterification of acetic acid with ethanol.
  • 2. Ethyl Acetate can be formed by the direct dehydrogenation of ethanol over a copper catalyst at elevated temperatures, producing hydrogen as a by-product.
  • 3. Ethyl Acetate has been reported to be formed by the direct esterification or interesterification of acetic acid, where the acetic acid was produced from a biomass fermentation process.
  • Ethyl acetate when produced by one such process from biomass was the intermediate product that was then hydrogenated to ethanol as the final fuel additive product. It would appear that ethyl acetate in this type process would be cheaper than the ethanol produced from the same process.
  • In one embodiment of the present invention, a fuel blend is provided, consisting of: a hydrocarbon-containing fuel component; and ethyl acetate. The hydrocarbon-containing fuel component may be gasoline or diesel. The hydrocarbon-containing fuel component may also be petroleum gas, natural gas, liquefied petroleum gas, or propane. The hydrocarbon-containing fuel component may also be bioethanol or biodiesel.
  • In another embodiment of the present invention, the ethyl acetate may be added to mixtures of diesel fuel and biodiesel to reduce the cloud point to improve winter operation performance of said mixtures. The ethyl acetate may be added to biodiesel and mixtures of biodiesel to reduce the cloud point to improve winter operation and performance of said biodiesel or mixtures thereof. The ethyl acetate may be added to diesel fuel, or mixtures of biodiesel and diesel fuel, or directly to biodiesel or mixtures of biodiesel to adjust the viscosity of said fuel mixtures.
  • In various embodiments of the present invention, the fuel blends may be used for
  • over the road diesel motor transport vehicles,
  • private or commercial diesel passenger vehicles,
  • marine diesel engines,
  • diesel-electric train engines,
  • a marine application (such as jet skis, outboard motors and inboard motors),
  • a recreational application (such as snowmobiles, mopeds, and motorcycles)
  • a residential application (such as lawnmowers, string trimmers, and chain saws),
  • diesel powered construction equipment, or
  • portable or stationary diesel powered electric generators.
  • In another embodiment, the hydrocarbon-containing fuel component may be gasoline, diesel, petroleum gas, natural gas, liquefied petroleum gas, propane, bioethanol or biodiesel, or any combination thereof.
  • In another embodiment, the fuel blend may comprise least 5% ethyl acetate by volume. The fuel blend may comprise at least 8% ethyl acetate by volume. The fuel blend may comprise at least 10% ethyl acetate by volume.
  • In another embodiment, the ethyl acetate may be a biomass intermediate product in the ethanol production process. The ethyl acetate may be formed by the acid catalyzed esterification of acetic acid with ethanol. The ethyl acetate may be formed by the direct esterification of acetic acid. The ethyl acetate may be formed by the inter-esterification of acetic acid. The ethyl acetate may be formed by the dehydrogenation of ethanol.

Claims (39)

1. A fuel blend consisting of:
a hydrocarbon-containing fuel component; and
ethyl acetate.
2. The fuel blend of claim 1, wherein said hydrocarbon-containing fuel component is selected from the group consisting of gasoline and diesel.
3. The fuel blend of claim 1, wherein said hydrocarbon-containing fuel component is selected from the group consisting of petroleum gas, natural gas, liquefied petroleum gas, and propane.
4. The fuel blend of claim 1, wherein said hydrocarbon-containing fuel component is selected from the group consisting of bioethanol and biodiesel.
5. The fuel blend of claim 4 wherein ethyl acetate is added to mixtures of diesel fuel and biodiesel to reduce the cloud point to improve winter operation performance of said mixtures.
6. The fuel blend of claim 4 wherein ethyl acetate is added to biodiesel and mixtures of biodiesel to reduce the cloud point to improve winter operation and performance of said biodiesel or mixtures thereof.
7. The fuel blend of claim 4 wherein ethyl acetate is added to diesel fuel, or mixtures of biodiesel and diesel fuel, or directly to biodiesel or mixtures of biodiesel to adjust the viscosity of said fuel mixtures.
8. The fuel blends of claim 5 wherein the application is for over the road diesel motor transport vehicles.
9. The fuel blends of claim 6 wherein the application is for over the road diesel motor transport vehicles.
10. The fuel blends of claim 7 wherein the application is for over the road diesel motor transport vehicles.
11. The fuel blends of claim 5 wherein the application is for private or commercial diesel passenger vehicles.
12. The fuel blends of claim 6 wherein the application is for private or commercial diesel passenger vehicles.
13. The fuel blends of claim 7 wherein the application is for private or commercial diesel passenger vehicles.
14. The fuel blends of claim 5 wherein the application is for marine diesel engines.
15. The fuel blends of claim 6 wherein the application is for marine diesel engines.
16. The fuel blends of claim 7 wherein the application is for marine diesel engines.
17. The fuel blends of claim 5 wherein the application is for diesel-electric train engines.
18. The fuel blends of claim 6 wherein the application is for diesel-electric train engines.
19. The fuel blends of claim 7 wherein the application is for diesel-electric train engines.
20. The fuel blends of claim 5 wherein the application is for diesel powered construction equipment.
21. The fuel blends of claim 6 wherein the application is for diesel powered construction equipment.
22. The fuel blends of claim 7 wherein the application is for diesel powered construction equipment.
23. The fuel blends of claim 5 wherein the application is for portable or stationary diesel powered electric generators.
24. The fuel blends of claim 6 wherein the application is for portable or stationary diesel powered electric generators.
25. The fuel blends of claim 7 wherein the application is for portable or stationary diesel powered electric generators.
26. The fuel blend of claim 1, wherein said hydrocarbon-containing fuel component is selected from the group consisting of gasoline, diesel, petroleum gas, natural gas, liquefied petroleum gas, propane, bioethanol and biodiesel, or any combination thereof.
27. The fuel blend of claim 1, wherein said fuel blend comprises at least 5% ethyl acetate by volume.
28. The fuel blend of claim 1, wherein said fuel blend comprises at least 10% ethyl acetate by volume.
29. The fuel blend of claim 1, wherein said fuel blend is used in a marine application.
30. The fuel blend of claim 29, wherein said marine application is selected from the group consisting of jet skis, outboard motors and inboard motors.
31. The fuel blend of claim 1, wherein said fuel blend is used in a recreational application.
32. The fuel blend of claim 31, wherein said recreational application is selected from the group consisting of snowmobiles, mopeds, and motorcycles.
33. The fuel blend of claim 1, wherein said fuel blend is used in a residential application.
34. The fuel blend of claim 33, wherein said residential application is selected from the group consisting of lawnmowers, string trimmers, and chain saws.
35. The fuel blend of claim 1, wherein said ethyl acetate is a biomass intermediate product in the ethanol production process.
36. The fuel blend of claim 35, wherein said ethyl acetate is formed by the acid catalyzed esterification of acetic acid with ethanol.
37. The fuel blend of claim 35, wherein said ethyl acetate is formed by the direct esterification of acetic acid.
38. The fuel blend of claim 35, wherein said ethyl acetate is formed by the inter-esterification of acetic acid.
39. The fuel blend of claim 35 wherein said ethyl acetate is formed by the dehydrogenation of ethanol.
US12/792,867 2010-06-03 2010-06-03 Ethyl Acetate As Fuel Or Fuel Additive Abandoned US20110296744A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017214493A1 (en) * 2016-06-09 2017-12-14 Fueltek, Inc. Hygroscopic fuel blends and processes for producing same
CN115093887A (en) * 2022-07-29 2022-09-23 中国石油大学(华东) Preparation method of alcohol-based diesel fuel additive
US12338403B2 (en) 2021-08-31 2025-06-24 Swedish Biofuels Ab Method for producing motor fuel from ethanol

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1421879A (en) * 1919-11-12 1922-07-04 Us Ind Alcohol Co Engine fuel
US2228662A (en) * 1939-05-31 1941-01-14 Standard Oil Co Motor fuel
US2334006A (en) * 1939-05-31 1943-11-09 Standard Oil Co California Motor fuel
US3879176A (en) * 1970-12-11 1975-04-22 Nippon Oil Co Ltd Liquefied petroleum gas compositions
US5380346A (en) * 1992-06-12 1995-01-10 Fritz; James E. Fortified hydrocarbon and process for making and using the same
US6923839B2 (en) * 2001-06-26 2005-08-02 Cooper Cameron Fuel blend for an internal combustion engine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1421879A (en) * 1919-11-12 1922-07-04 Us Ind Alcohol Co Engine fuel
US2228662A (en) * 1939-05-31 1941-01-14 Standard Oil Co Motor fuel
US2334006A (en) * 1939-05-31 1943-11-09 Standard Oil Co California Motor fuel
US3879176A (en) * 1970-12-11 1975-04-22 Nippon Oil Co Ltd Liquefied petroleum gas compositions
US5380346A (en) * 1992-06-12 1995-01-10 Fritz; James E. Fortified hydrocarbon and process for making and using the same
US6923839B2 (en) * 2001-06-26 2005-08-02 Cooper Cameron Fuel blend for an internal combustion engine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Wood et al., Ethanol:Turning Up The Heat, 2009 www.odec.ca.projects/2010/dejoxm2/index.htm *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017214493A1 (en) * 2016-06-09 2017-12-14 Fueltek, Inc. Hygroscopic fuel blends and processes for producing same
US12338403B2 (en) 2021-08-31 2025-06-24 Swedish Biofuels Ab Method for producing motor fuel from ethanol
CN115093887A (en) * 2022-07-29 2022-09-23 中国石油大学(华东) Preparation method of alcohol-based diesel fuel additive

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AS Assignment

Owner name: LURGI PSI, INC., TENNESSEE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:JONES, RAY;REEL/FRAME:024477/0280

Effective date: 20100602

AS Assignment

Owner name: LURGI, INC., TENNESSEE

Free format text: CHANGE OF NAME;ASSIGNOR:LURGI PSI, INC.;REEL/FRAME:026836/0727

Effective date: 20061009

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE