WO2011011588A1 - Composition de carburant issue du biodiesel - Google Patents

Composition de carburant issue du biodiesel Download PDF

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Publication number
WO2011011588A1
WO2011011588A1 PCT/US2010/042880 US2010042880W WO2011011588A1 WO 2011011588 A1 WO2011011588 A1 WO 2011011588A1 US 2010042880 W US2010042880 W US 2010042880W WO 2011011588 A1 WO2011011588 A1 WO 2011011588A1
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Prior art keywords
fuel composition
oxygen
fuel
biodiesel
ester
Prior art date
Application number
PCT/US2010/042880
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English (en)
Inventor
Chandrashekhar H. Joshi
Original Assignee
Joshi Chandrashekhar H
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Filing date
Publication date
Application filed by Joshi Chandrashekhar H filed Critical Joshi Chandrashekhar H
Priority to CA2768862A priority Critical patent/CA2768862A1/fr
Publication of WO2011011588A1 publication Critical patent/WO2011011588A1/fr

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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, 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
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/50—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C10G2300/1018—Biomass of animal origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/304—Pour point, cloud point, cold flow properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/08—Jet fuel
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T50/00—Aeronautics or air transport
    • Y02T50/60—Efficient propulsion technologies, e.g. for aircraft
    • Y02T50/678—Aviation using fuels of non-fossil origin

Definitions

  • the present invention relates to a fuel composition and a method of producing the fuel composition.
  • the fuel composition can be useful in cold temperature environments and as aviation fuel.
  • Aviation fuel such as jet fuel
  • jet fuel is generally a specialized type of petroleum-based fuel used to power an aircraft and is generally of a higher quality than fuel used for ground transportation.
  • Aviation fuel is designed to remain liquid at cold temperatures as found in the upper atmosphere where aircraft fly.
  • Aviation fuels can include hydrocarbons, such as paraffins; olefins; naphthenes and aromatics; antioxidants; and metal deactivators.
  • Known aviation fuels include jet fuels, such as JP-5, JP 8, Jet A, Jet A-I, and Jet B.
  • Jet fuel has the highest volumetric energy density of liquid fuels, such as ethanol, butanol, bio-kerosene, and biodiesel.
  • the present invention provides a fuel composition including oil derived from a biological source and alcohol.
  • the fuel composition is at least substantially free of oxygen and oxygen-containing compounds.
  • the oil may be selected from the group of biological sources including vegetable oil, crop seed oil, animal oil, animal fat, and combinations thereof.
  • the alcohol may be selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, and mixtures thereof.
  • the fuel composition may be oxygen free.
  • the fuel composition may have a level of oxygen that is less than the level of oxygen in biodiesel.
  • the fuel composition may have a level of oxygen that is less than 2000 parts per million oxygen based on the fuel composition.
  • the fuel composition includes molecules and each of the molecules may have a carbon chain length of from 12 to 14 carbon atoms.
  • the fuel composition may be used for aviation fuel. In another embodiment, the fuel composition may be used for ground transportation fuel in a cold climate.
  • the fuel composition may include an alkane.
  • the fuel composition may further include a catalyst.
  • the catalyst may be selected from the group consisting of calcium hydroxide, potassium hydroxide and mixtures thereof.
  • the present invention provides a method for preparing a fuel composition.
  • the method includes reacting oil derived from a biological source and alcohol to produce an alkyl ester-containing product; and removing at least a portion of oxygen from the alkyl ester-containing product to produce a fuel composition which is at least substantially free of oxygen and oxygen-containing compounds.
  • the alkyl ester-containing product may include an alkyl ester selected from the group consisting of methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester and mixtures thereof.
  • the alkyl ester-containing product may include biodiesel.
  • the reacting step may be conducted in accordance with a transesterification reaction.
  • the removing step may be conducted in accordance with a nucleophilic acyl reaction.
  • the cloud point of the fuel composition may be lower than the cloud point of the alkyl ester-containing product.
  • the removing step may further include removing a portion of carbon atoms from the alkyl ester-containing product.
  • the fuel composition includes molecules and each of the molecules may have a carbon chain length of from 12 to 14 carbon atoms.
  • Figure 1 is a schematic showing a reaction process for reducing an ethyl ester to ethanol in accordance with an embodiment of the present invention.
  • Figure 2 is a schematic showing a process for chemoselectively reducing secondary and tertiary alcohols (e.g., 2-decanol) to alkanes (e.g., decane) in accordance with an embodiment of the present invention.
  • secondary and tertiary alcohols e.g., 2-decanol
  • alkanes e.g., decane
  • the present invention relates to a fuel composition and method thereof.
  • the fuel composition can be used in various applications.
  • the fuel composition can be employed as a cold weather fuel for use in ground transportation vehicles, such as trucks, automobiles, railroads, and the like, and as an aviation fuel for use in aircrafts, such as airplanes, helicopters, and the like.
  • the fuel composition of the present invention can be prepared based on biodiesel.
  • biodiesel can be produced and converted to a fuel composition that is suitable for use as cold weather ground transportation and aviation fuel.
  • Biodiesel is derived from plant oils, algae oils, and animal fats, and therefore, the present invention provides a fuel composition which is grown and produced using standard agricultural and chemical processing methods.
  • Biodiesel can be converted to a fuel composition including an alkane or a mixture of alkanes.
  • Biodiesel has various characteristics and properties that make it unattractive for use in cold weather environments and as aviation fuel. For example, biodiesel has an energy density that is lower than required for aviation fuel. Further, at low temperatures, certain molecules within biodiesel begin to agglomerate into solid particles causing the normally translucent biodiesel to appear cloudy. The highest temperature at which the biodiesel begins to agglomerate or cloud is called the cloud point.
  • the cloud point is an important characteristic of fuels used in internal combustion engines and jet engines because the presence of solid or agglomerated particles causes fuel pumps and injectors to clog rendering the engines inoperable.
  • the cloud point for some common biodiesel products are as follows: 0 0 C for canola; 1°C for soybean; -6 0 C for safflower; 1°C for sunflower; -2°C for rapeseed; 13°C for jatropha; and 15°C for palm.
  • the cloud points of various fossil fuels are as follows: 0 0 C for ULS diesel; -40 0 C for Jet A; -47°C for JP-8; and -40 0 C for ULS kerosene.
  • Aviation fuels have very low cloud points. For aviation fuels, the low cloud point is important because the fuel must remain liquid at high altitude where temperatures are well below zero. For ground transportation fuels, a low cloud point is important because the fuel must remain liquid in cold weather environments where ground vehicles are used.
  • the cloud point of fuel is a function of its chemical composition.
  • Most fossil fuels include numerous compounds in the form of linear or branched chains of carbon atoms with one or more oxygen and hydrogen atoms bound to each carbon atom.
  • a general composition of conventional aviation fuel is C m H n , where m is an integer from 12-14, and n is an integer from 20 to 30, and a general composition of conventional biodiesel is C j HkCO 2 CHs, where _, is an integer from 14 to 16, and k is an integer from 26 to 33.
  • Jet A and synthetic aviation fuel are both composed of alkanes, which are compounds of carbon and hydrogen only.
  • Biodiesel is a vegetable oil or animal fat-based diesel fuel composed of long- chain alkyl esters.
  • the differences between aviation fuels and biodiesel include (i) the size of the molecules (biodiesel molecules are larger and include more carbon atoms per molecule) and (ii) the presence of oxygen (biodiesel contains oxygen, whereas aviation fuel is at least substantially oxygen free).
  • the presence of the oxygen in the biodiesel molecule causes it to have a degree of polarity (an electrostatic charge separation). This polarity results in an attraction between oxygen in one molecule to hydrogen atoms bound in an adjacent molecule through van der Waal's forces. This attractive force among biodiesel molecules causes solidification at higher temperatures than a similar molecule without oxygen.
  • Table 1 shows a comparison of the solidification temperature for various alkanes, i.e., oxygen- free molecules, and corresponding alcohols, i.e., oxygen-containing molecules. As shown below, the alcohols have a single oxygen atom in addition to the corresponding alkane. The alcohol has a higher solidification point than the corresponding alkane. The presence of additional oxygen atoms would result in a greater difference in solidification points as compared to the alkane.
  • the reduction or removal of oxygen or oxygen-containing components from biodiesel can be accomplished by employing a variety of chemical or thermal processes that result in a hydrocarbon, e.g., alkane, having less or no oxygen.
  • the resulting hydrocarbon e.g., fuel
  • the process used for the reduction in or removal of oxygen from biodiesel can include the reaction of an ester group, e.g., alkyl ester, with other chemicals either catalytically or electrically. In addition to removing oxygen atoms from the ester group, this ester reaction may also remove carbon atoms such that the overall carbon chain length of the biodiesel molecule is reduced.
  • the fuel composition of the present invention is substantially free of oxygen and has a carbon chain length of from 12 to 14 carbon atoms.
  • This embodiment produces a fuel composition that is essentially comparable to aviation fuel (and compatible with aviation fuels to produce a mixture thereof) and can be used as a fuel for ground transportation vehicles in cold climates.
  • the produced fuel contains a reduced oxygen content and has a carbon chain length of 12-14 atoms.
  • the fuel composition of the present invention contains less than 2000 parts per million of oxygen based on the fuel composition.
  • Biodiesel can be produced by a variety of conventional processes that are known in the art.
  • Biodiesel is an oil-based diesel fuel, wherein the oil is obtained from a biological source, such as, but not limited to, a vegetable oil or animal fat.
  • Oils suitable for use in producing biodiesel can be oils obtained from a wide variety of biological sources.
  • Suitable oils from a biological source can include, but are not limited to, crop seed oils, vegetables oils, animal oils, animal fats, and combinations thereof.
  • the crop seed oils can be isolated from biological sources, such as, but not limited to, rapeseed oil, sunflower oil, mustard oil, canola oil, peanut oil, palm oil, coconut oil, soybean oil, and mixtures thereof.
  • suitable oils include, but are not limited to, waste vegetable oil; animal fats, including tallow, lard, yellow grease, chicken fat, by-products of the production of Omega-3 fatty acids from fish oil, and mixtures thereof; algae; oil from halophytes, such as salicornia bigelovii; and mixtures thereof.
  • the oil from a biological source can be distilled, separated, or at least partially purified to increase or decrease the content of a particular component of the oil, such as, but not limited to, triglycerides, diglycerides, monoglycerides, saturated fatty acids, unsaturated fatty acids, trilaurin, erucic acid, lauric acid, oleic acid, linoleic acid, linolenic acid, stearic acid, palmitic acid, and mixtures thereof.
  • a particular component of the oil such as, but not limited to, triglycerides, diglycerides, monoglycerides, saturated fatty acids, unsaturated fatty acids, trilaurin, erucic acid, lauric acid, oleic acid, linoleic acid, linolenic acid, stearic acid, palmitic acid, and mixtures thereof.
  • the oil from a biological source can be hydrocracked in accordance with conventional processes known in the art to yield smaller molecular weight species.
  • Biodiesel includes long-chain alkyl esters, such as, but not limited to, methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, and mixtures thereof.
  • Biodiesel can be prepared by a transesterification process, wherein lipids are chemically reacted with alcohol.
  • Suitable lipids include the oils derived from biological sources (such as, but not limited to, vegetable oils and animal fats) described herein.
  • Suitable alcohols include, but are not limited to, ethanol, methanol, propanol, isopropanol, butanol, and mixtures thereof.
  • the transesterification process can include the presence of catalyst.
  • the catalyst can be selected from a wide variety of materials known in the art to facilitate the reaction between lipids and alcohols. Suitable catalysts include, but are not limited to, calcium hydroxide, potassium hydroxide, and mixtures thereof.
  • the transesterification reaction can be carried out using a variety of conventional processes known in the art. Suitable processes include, but are not limited to, common batch processes, supercritical processes, and ultrasonic methods. In general, the transesterification reaction converts base oil in the vegetable or animal starting materials to the desired esters, e.g., alkyl esters, in the biodiesel product. The transesterification process can produce by-products.
  • free fatty acids present in the base oil are typically converted to soap and removed from the process or they are esterified using an acidic catalyst.
  • glycerol can be produced as a by-product of the transesterification process.
  • this crude glycerol is purified by employing a conventional purification process known in the art, such as, but not limited to, vacuum distillation.
  • the refined, purified glycerol then can be utilized directly or converted into other products.
  • biodiesel is made by reacting animal fat or vegetable oil with methanol by transesterification.
  • the process yields two products: (i) methyl esters, i.e., biodiesel, and (ii) glycerin, i.e., a by-product that can be used for the production of soap.
  • this process can be conducted on any scale, e.g., in a mason jar or in a large-scale production facility.
  • vegetable oil or animal fat reacts with ethanol or methanol or mixtures thereof, and a catalyst, such as calcium hydroxide or potassium hydroxide or a mixture thereof.
  • a catalyst such as calcium hydroxide or potassium hydroxide or a mixture thereof.
  • the initial oil or fat is relatively low in free fatty acids in order to reduce or prevent the formation of soap.
  • the reactants are mixed thoroughly for about an hour at room temperature or slightly-elevated temperature. In one embodiment, the temperature is from about 20 0 C to about 50 0 C. After about one hour of mixing, the solution is allowed to settle.
  • the heavy glycerin (glycerol) settles to the bottom of the solution and biodiesel is formed on top.
  • the glycerin is then separated by, for example, draining it from the bottom of a settling tank.
  • separation can be accomplished by using a centrifuge which is typically employed in large scale production of biodiesel to reduce the time needed to carry out the process.
  • the final steps in the process include washing and drying the biodiesel using conventional methods known in the art.
  • a fine mist of water is applied to the biodiesel to absorb any trace amounts of the catalyst remaining in the biodiesel. This is separated from the biodiesel, for example, in the same manner as the glycerin separation.
  • a subsequent bubbling of air through the biodiesel removes any remaining water to ensure a high purity biodiesel product for use in diesel engines.
  • a pretreatment of the free fatty acid can be conducted using conventional methods known in the art.
  • the vegetable oil or animal fat can be reacted with hydrochloric acid and methanol. This pretreatment converts the free fatty acids into biodiesel.
  • the remaining vegetable oil can be converted to biodiesel using the transesterification process described herein.
  • multiple reactions may be necessary to reduce or remove the oxygen and/or oxygen-containing compounds from biodiesel to produce a fuel having a low solidification temperature or cloud point for use in cold climates or as aviation fuel.
  • an ester such as an alkyl ester in biodiesel
  • LiAlH 4 lithium aluminum hydride
  • Figure 1 shows a four-step reaction process for reducing an ethyl ester (I) to ethanol (V).
  • the final step is a simple acid/base reaction. Protonation (H+) of the alkoxide oxygen creates the primary alcohol product (V) from the intermediate complex.
  • FIG. 2 shows a process for chemoselectively reducing secondary and tertiary alcohols to alkanes. This direct pathway shows selective reduction of the hydroxyl (OH) moiety without affecting other functional groups.
  • 2-decanol compound Ia
  • decane compound 2a
  • the reducing system in Figure 2 includes dissolving 2-decanol in a CH 2 ClCH 2 Cl solvent with hydrosilane and indium chloride (InCl 3 ) catalyst, at a temperature of about 80 0 C for about 4 hours.
  • the fuel composition of the present invention can provide at least one of the following benefits:
  • the cloud point of the fuel composition is less than the cloud point of the biodiesel.
  • the cloud point can be less than or equal to about -40 0 C.
  • the cloud point can be less than about -20 0 C.
  • Cold climate conditions can vary and in one embodiment, cold climate temperatures can be less than or equal to about 0 0 C.

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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)
  • Fats And Perfumes (AREA)

Abstract

La présente invention concerne une composition de carburant et son procédé de préparation. Ladite composition de carburant peut, en particulier, être utilisée en tant que carburant aviation et en tant que carburant pour les moyens de transport terrestres par temps froid. Cette composition de carburant comprend de l'huile d'origine biologique, telle que de l'huile végétale et/ou de la graisse animale. Ladite composition de carburant peut, en outre, être à base de biodiesel. De plus, la composition de carburant de la présente invention comprend, par rapport au biodiesel, une quantité réduite d'oxygène, voire pas d'oxygène du tout.
PCT/US2010/042880 2009-07-22 2010-07-22 Composition de carburant issue du biodiesel WO2011011588A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2768862A CA2768862A1 (fr) 2009-07-22 2010-07-22 Composition de carburant issue du biodiesel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22758309P 2009-07-22 2009-07-22
US61/227,583 2009-07-22

Publications (1)

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WO2011011588A1 true WO2011011588A1 (fr) 2011-01-27

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US (1) US20110016776A1 (fr)
CA (1) CA2768862A1 (fr)
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US9914880B2 (en) 2015-12-04 2018-03-13 Uop Llc Method of increasing the yield of aviation fuel from renewable feedstocks

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US9914880B2 (en) 2015-12-04 2018-03-13 Uop Llc Method of increasing the yield of aviation fuel from renewable feedstocks

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