WO2011037901A2 - Production de carburant à partir d'une charge contenant un triglycéride et/ou un alkyl ester d'acide gras - Google Patents

Production de carburant à partir d'une charge contenant un triglycéride et/ou un alkyl ester d'acide gras Download PDF

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Publication number
WO2011037901A2
WO2011037901A2 PCT/US2010/049614 US2010049614W WO2011037901A2 WO 2011037901 A2 WO2011037901 A2 WO 2011037901A2 US 2010049614 W US2010049614 W US 2010049614W WO 2011037901 A2 WO2011037901 A2 WO 2011037901A2
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WIPO (PCT)
Prior art keywords
feedstock
lipid material
fuel
fatty acid
triglyceride
Prior art date
Application number
PCT/US2010/049614
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English (en)
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WO2011037901A3 (fr
Inventor
Patrick L. Hanks
William J. Novak
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Exxonmobil Research And Engineering Company
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Publication date
Application filed by Exxonmobil Research And Engineering Company filed Critical Exxonmobil Research And Engineering Company
Priority to JP2012530965A priority Critical patent/JP2013506031A/ja
Priority to CN2010800420525A priority patent/CN102510893A/zh
Priority to EP10819319.4A priority patent/EP2480638A4/fr
Priority to CA2772939A priority patent/CA2772939A1/fr
Priority to AU2010298473A priority patent/AU2010298473A1/en
Priority to SG2012013165A priority patent/SG178874A1/en
Publication of WO2011037901A2 publication Critical patent/WO2011037901A2/fr
Publication of WO2011037901A3 publication Critical patent/WO2011037901A3/fr

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    • 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
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
    • 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
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
    • C10G3/46—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof in combination with chromium, molybdenum, tungsten metals or compounds thereof
    • 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
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
    • C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
    • 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
    • C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • 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
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
    • 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
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1051—Kerosene having a boiling range of about 180 - 230 °C
    • 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
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1055—Diesel having a boiling range of about 230 - 330 °C
    • 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
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1059—Gasoil having a boiling range of about 330 - 427 °C
    • 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
    • C10G2300/301—Boiling range
    • 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
    • C10G2400/02—Gasoline
    • 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
    • C10G2400/04—Diesel oil
    • 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
    • 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

Definitions

  • This invention relates to the production of a fuel composition from a feedstock that comprises lipid material and mineral oil. More particularly, this invention relates to the production of at least one transportation fuel composition from a feedstock that comprises mineral oil and lipid material selected from the group consisting of triglyceride, fatty acid alkyl ester and a combination thereof, wherein the production includes at least one hydrocracking step.
  • a standard approach for converting vegetable oils or other fatty acid derivatives into fuels such as diesel type fuels has been accomplished by a transesterification reaction.
  • This reaction involves contacting the vegetable oil with methanol in the presence of a catalyst, such as sodium hydroxide.
  • the product that is produced is a fatty acid methyl ester, and the product can be used directly as a diesel fuel or blend component for diesel fuel.
  • Publication No. 2009/0166256 discloses a process for the manufacture of diesel range hydrocarbons that are low in sulfur and that include up to 20% by weight of a biocomponent feedstock.
  • the process includes the use of a staged co-hydrotreating process for the manufacture of diesel range hydrocarbons from at least one biocomponent feedstock and at least one mineral hydrocarbon feedstock.
  • This invention provides processes for producing fuel, particularly transportation fuel, from biological material, e.g., lipid material.
  • the product includes one or more high quality transportation fuels such as gasoline, kerosene, jet fuel, and diesel fuel.
  • a method of producing transportation fuel includes producing or providing a feedstock containing lipid material and mineral oil.
  • the lipid material can be selected from the group consisting of triglycerides, fatty acid alkyl esters, and combinations thereof.
  • the feedstock can be hydrocracked to produce the transportation fuel.
  • a method of producing transportation fuel that includes a step of preparing or providing a feedstock containing mineral oil at a content of not greater than 99 wt % mineral oil, based on total weight of the feedstock, and a lipid material selected from the group consisting of triglycerides, fatty acid alkyl esters and combinations thereof.
  • the feedstock can have an initial boiling point of at least 100°C and/or a final boiling point of not greater than 500°C.
  • the feedstock can be hydrocracked to produce the transportation fuel.
  • This invention provides processes for producing one or more high quality fuels, particularly at least one transportation fuel, from feedstock that includes biological material, e.g., lipid or lipidic material.
  • the processes can be carried out without producing a significant amount of undesirable side reactions such as cracking, polymerization, and
  • aromatization which can be a consequence of large heats of reaction.
  • the invention provides for the production of product that is high in quality. Additionally, catalyst used in the process is not adversely affected to any significant extent.
  • the feedstock that is used in the invention comprises both lipid material and mineral oil.
  • mineral oil is meant a fossil/mineral fuel source, such as crude oil, and not the commercial organic product, such as sold under the CAS number 8020-83-5, e.g., by Aldrich.
  • the lipid material and mineral oil are mixed together prior to processing.
  • the lipid material and mineral oil are provided as separate streams into an appropriate processing unit or vessel.
  • lipid material as used according to the invention is a composition comprised of biological materials.
  • biological materials include vegetable fats/oils, animal fats/oils, fish oils, pyrolysis oils, and algae lipids/oils, as well as components of such materials.
  • the lipid material includes one or more type of lipid
  • Lipid compounds are typically biological compounds that are insoluble in water, but soluble in nonpolar (or fat) solvents.
  • Non-limiting examples of such solvents include alcohols, ethers, chloroform, alkyl acetates, benzene, and combinations thereof.
  • lipids include, but are not necessarily limited to, fatty acids, glycerol-derived lipids (including fats, oils and
  • phospholipids include ceramides, cerebrosides, gangliosides, and sphingomyelins), steroids and their derivatives, terpenes and their derivatives, fat-soluble vitamins, certain aromatic compounds, and long-chain alcohols and waxes.
  • lipids In living organisms, lipids generally serve as the basis for cell membranes and as a form of fuel storage. Lipids can also be found conjugated with proteins or carbohydrates, such as in the form of lipoproteins and lipopolysaccharides.
  • Examples of vegetable oils that can be used in accordance with this invention include, but are not limited to rapeseed (canola) oil, soybean oil, coconut oil, sunflower oil, palm oil, palm kernel oil, peanut oil, linseed oil, tall oil, corn oil, castor oil, jatropha oil, jojoba oil, olive oil, flaxseed oil, camelina oil, safflower oil, babassu oil, tallow oil and rice bran oil.
  • rapeseed canola
  • soybean oil soybean oil
  • coconut oil sunflower oil
  • palm oil palm kernel oil
  • peanut oil linseed oil
  • tall oil corn oil
  • castor oil jatropha oil
  • jojoba oil olive oil
  • flaxseed oil camelina oil
  • safflower oil camelina oil
  • babassu oil babassu oil
  • tallow oil and rice bran oil examples of vegetable oils that can be used in accordance with this invention.
  • Vegetable oils as referred to herein can also include processed vegetable oil material.
  • processed vegetable oil material include fatty acids and fatty acid alkyl esters.
  • Alkyl esters typically include Ci-C 5 alkyl esters. One or more of methyl, ethyl, and propyl esters are preferred.
  • animal fats examples include, but are not limited to, beef fat (tallow), hog fat (lard), turkey fat, fish fat/oil, and chicken fat.
  • the animal fats can be obtained from any suitable source including restaurants and meat production facilities.
  • Animal fats as referred to herein also include processed animal fat material.
  • processed animal fat material include fatty acids and fatty acid alkyl esters.
  • Alkyl esters typically include Ci-C 5 alkyl esters. One or more of methyl, ethyl, and propyl esters are preferred.
  • Algae oils or lipids are typically contained in algae in the form of membrane components, storage products, and metabolites. Certain algal strains, particularly microalgae such as diatoms and cyanobacteria, contain proportionally high levels of lipids. Algal sources for the algae oils can contain varying amounts, e.g., from 2 wt% to 40 wt% of lipids, based on total weight of the biomass itself.
  • Algal sources for algae oils include, but are not limited to, unicellular and multicellular algae. Examples of such algae include a rhodophyte, chlorophyte, heteronochphyte, tribophyte, glaucophyte, chlorarachniophyte, euglenoid, haptophyte, cryptomonad, dinoflagellum, phytoplankton, and the like, and combinations thereof. In one embodiment, algae can be of the classes Chlorophyceae and/or Haptophyta.
  • Neochloris oleoabundans Scenedesmus dimorphus, Euglena gracilis, Phaeodactylum tricornutum, Pleurochrysis carterae, Prymnesium parvum, Tetraselmis chui, and
  • the lipid material portion of the feedstock can be comprised of triglycerides, fatty acid alkyl esters, or preferably combinations thereof.
  • the feedstock can include at least 0.05 wt % lipid material, based on total weight of the feedstock provided for processing into fuel, preferably at least 0.5 wt%, for example at least 1 wt%, at least 2 wt%, or at least 4 wt%.
  • the feedstock can include not more than 40 wt% lipid material, based on total weight of the feedstock, preferably not more than 30 wt%, for example not more than 20 wt% or not more than 10 wt%.
  • the lipid material contains triglyceride.
  • Types of triglycerides can be determined according to their fatty acid constituents.
  • the fatty acid constituents can be readily determined using Gas Chromatography (GC) analysis. This analysis involves extracting the fat or oil, saponifying (hydrolyzing) the fat or oil, preparing an alkyl (e.g., methyl) ester of the saponified fat or oil, and determining the type of (methyl) ester using GC analysis.
  • a majority (i.e., greater than 50%) of the triglyceride present in the lipid material can be comprised of C 8 to C 22 fatty acid constituents, based on total triglyceride present in the lipid material.
  • a fatty acid or fatty acid ester molecule is specified as a "C xx " fatty acid, fatty acid constituent, or fatty acid ester, what is meant is that "xx" is the number of carbons on the carbon side of the carboxylate linkage, i.e., including the carboxylate carbon, whereas, in fatty acid esters, the ester carbons are not included in the "C xx " and are the carbons on the oxygen side of the carboxylate linkage, i.e., stopping at the carboxylate oxygen.
  • a triglyceride is a molecule having a structure identical to the reaction product of glycerol and three fatty acids.
  • a triglyceride is described herein as being comprised of fatty acids, it should be understood that the fatty acid component does not necessarily contain a carboxylic acid hydrogen.
  • a majority of the triglyceride present in the lipid material can preferably be comprised of Ci 0 to C 18 , for example C 12 to Ci8, fatty acid constituents, based on total triglyceride present in the lipid material.
  • the lipid material includes triglyceride, with at least 20 wt%, preferably at least 30 wt%, for example at least 40 wt%, of the triglyceride being comprised of lauric acid (C 12:0) constituents.
  • the lipid material includes triglyceride, with 40 wt% to 60 wt%, for example from 42 wt% to 58 wt% or from 44 wt% to 55 wt%, of the triglyceride being comprised of lauric acid constituents. Unless otherwise unambiguously specified, percentages expressed herein are percentages based on a number total of elements or constituents.
  • the lipid material includes triglyceride, with at least 2 wt%, preferably at least 5 wt%, for example at least 10 wt%, of the triglyceride being comprised of myristic acid (C 14:0) constituents. Additionally or alternately, the lipid material includes triglyceride, with 10 wt% to 28 wt%, for example 12 wt% to 26 wt% or 14 wt% to 24 wt%, of the triglyceride being comprised of myristic acid constituents.
  • the lipid material includes triglyceride, with at least 2 wt%, preferably at least 3 wt%, for example at least 5 wt%, of the triglyceride being comprised of palmitic acid (C 16:0) constituents. Additionally or alternately, the lipid material includes triglyceride, with 2 wt% to 12 wt%, for example 3 wt% to 10 wt% or 5 wt% to 8 wt%, of the triglyceride being comprised of palmitic acid constituents.
  • the lipid material includes triglyceride, with at least 0.5 wt%, preferably at least 1 wt%, for example at least 2 wt%, of the triglyceride being comprised of stearic acid (C 18:0) constituents. Additionally or alternately, the lipid material includes triglyceride, with 0.5 wt% to 60 wt%, for example 1 wt% to 55 wt% or 2 wt% to 50 wt%, of the triglyceride being comprised of stearic acid constituents.
  • the lipid material includes triglyceride, with at least 5 wt%, preferably at least 6 wt%, for example at least 7 wt%, of the triglyceride being comprised of oleic acid (C 18: 1) constituents. Additionally or alternately, the lipid material includes triglyceride, with 5 wt% to 30 wt%, for example 6 wt% to 25 wt% or 7 wt% to 20 wt%, of the triglyceride being comprised of oleic acid constituents.
  • the lipid material includes triglyceride, with at least 2 wt%, preferably at least 3 wt%, for example at least 4 wt%, of the triglyceride being comprised of erucic acid (C 22: 1) constituents. Additionally or alternately, the lipid material includes triglyceride, with 2 wt% to 70 wt%, for example 3 wt% to 65 wt% or 4 wt% to 60 wt% of the triglyceride being comprised of erucic acid constituents.
  • the lipid material comprises fatty acid alkyl ester.
  • the fatty acid alkyl ester comprises fatty acid methyl esters (FAME), fatty acid ethyl esters (FAEE), and/or fatty acid propyl esters.
  • the lipid material portion of the feedstock comprises fatty acid alkyl ester, and a majority of the fatty acid alkyl ester present in the lipid material is preferably FAME.
  • the lipid material portion of the feedstock can comprise at least 20 wt%, preferably at least 30 wt%, for example at least 40 wt% fatty acid alkyl ester, preferably FAME, based on total weight of the lipid material.
  • a majority of the fatty acid constituents of the fatty acid alkyl ester can be selected from the group consisting of caprylic acid (C 8:0), capric acid (C 10:0), lauric acid (C 12:0), myristic acid (C 14:0), palmitic acid (C 16:0), palmitoleic acid (C 16: 1), stearic acid (C 18:0), oleic acid (C 18: 1), linoleic acid (C 18:2), linolenic acid (C 18:3), erucic acid (C22: l), and
  • a majority of the fatty acid constituents of the FAME present in the lipid material portion can be selected from the group consisting of lauric acid (C 12:0), myristic acid (C 14:0), palmitic acid (C 16:0), palmitoleic acid (C 16: 1), stearic acid (C 18:0), oleic acid (C 18: 1), and combinations thereof, based on total amount of FAME present in the lipid material portion.
  • the feedstock provided according to this invention comprises a mineral oil.
  • mineral oils can include, but are not limited to, straight run (atmospheric) gas oils, vacuum gas oils, demetallized oils, coker distillates, cat cracker distillates, heavy naphthas (optionally but preferably at least partially denitrogenated and/or at least partially desulfurized), diesel boiling range distillate fraction (optionally but preferably at least partially denitrogenated and/or at least partially desulfurized), jet fuel boiling range distillate fraction (optionally but preferably at least partially denitrogenated and/or at least partially desulfurized), kerosene boiling range distillate fraction (optionally but preferably at least partially denitrogenated and/or at least partially desulfurized), and coal liquids.
  • the mineral oil that is included as a part of the feedstock can comprise any one of these example streams or any combination thereof that would be suitable for hydrocracking with the lipid material portion.
  • the feedstock does not contain any appreciable asphaltenes.
  • the mineral oil can be mixed with the lipid material portion and then hydrotreated to form a hydrotreated material.
  • the mineral oil can be hydrotreated to reduce the nitrogen and/or sulfur content before being mixed with the lipid material portion.
  • the mineral oil component can contain nitrogen-containing compounds (abbreviated as "nitrogen").
  • nitrogen nitrogen
  • the mineral oil can contain at least 5 wppm nitrogen, based on total weight of the mineral oil component.
  • the mineral oil will contain not greater than 1.0 wt% nitrogen, based on total weight of the mineral oil component. In general, at least a majority of the nitrogen will be in the form of
  • the mineral oil will typically contain sulfur-containing compounds (abbreviated as "sulfur” or “sulfur content”). Such compounds can typically be present in the mineral oil at a sulfur content greater than 500 wppm, or often greater than 0.1 wt%, based on total weight of the mineral oil. Preferably, the sulfur content of the mineral oil will not be greater than 6 wt%, preferably not greater than 4 wt%, based on total weight of the mineral oil.
  • the feedstock can include not greater than 99 wt% mineral oil, based on total weight of the feedstock.
  • the feedstock can include not greater than 98 wt%, for example not greater than 95 wt%, not greater than 90 wt%, not greater than 85 wt % mineral oil, or not greater than 80 wt%, based on total weight of the feedstock.
  • the feedstock can include at least 50 wt% mineral oil, based on total weight of the feedstock.
  • the feedstock can include at least 60 wt%, for example at least 70 wt%, at least 75 wt%, or at least 80 wt% mineral oil, based on total weight of the feedstock.
  • the feedstock that is hydrocracked can have an initial boiling point of at least 100°C, preferably at least 150°C, for example at least 180°C or at least 200°C.
  • the basic test method of determining the boiling points or ranges of such feedstock, as well as the fuel compositions produced according to this invention, can be by performing batch distillation according to ASTM D86-09el, Standard Test Method for Distillation of Petroleum Products at Atmospheric
  • the feedstock can have a final boiling point of not greater than 500°C, preferably not greater than 450°C, for example not greater than 400°C.
  • the process of the invention includes a step of hydrocracking the feedstock to produce the desired fuel product.
  • Hydrocracking refers to a process by which certain hydrocarbon molecules in a provided feedstock are broken into simpler molecules to produce a fuel product.
  • the fuel product can include one or more transportation fuels, such as gasoline, kerosene, jet fuel, and/or diesel, and these individual fuels can typically be separated into their component parts by fractionation.
  • the hydrocracking process can be carried out by contacting the feedstock, optionally but preferably with a hydrocracking catalyst, in the presence of hydrogen to form the product.
  • a hydrocracking catalyst for contacting the feedstock, optionally but preferably with a hydrocracking catalyst, in the presence of hydrogen to form the product.
  • the addition of hydrogen provides benefit to the cracking aspect of the process, in that the fuel product that is produced is typically more highly saturated, and can be further reduced in undesirable heteroatoms, such as nitrogen, oxygen, and sulfur, and can advantageously also be reduced in aromatic content and/or in unsaturations.
  • the hydrocracking catalyst used in the process of this invention can comprise an amorphous base or zeolite base and one or more Group VIII or Group VIB metal hydrogenation
  • the hydrocracking catalyst can comprise a crystalline zeolite cracking base upon which is deposited at least one Group VIII or Group VIB metal hydrogenating component.
  • Suitable Group VIII and Group VIB metals can include cobalt, nickel, iron, molybdenum, tungsten, and combinations thereof.
  • Suitable supports, additionally or alternately to zeolitic and/or amorphous bases, can include relatively high specific surface area metal oxides such as silica, silica- alumina, alumina, and titania.
  • While one preferred embodiment includes a catalyst comprising a Group VIB metal and a Group VIII metal (e.g., in oxide form, or preferably after the oxide form has been sulfidized under appropriate sulfidization conditions), optionally on a support, the catalyst may additionally or alternately contain additional components, such as other transition metals (e.g., Group V metals such as niobium), rare earth metals, organic ligands (e.g., as added or as precursors left over from oxidation and/or sulfidization steps), phosphorus compounds, boron compounds, fluorine-containing compounds, silicon-containing compounds, promoters, binders, fillers, or like agents, or combinations thereof.
  • the Groups referred to herein refer to Groups of the CAS Version as found in the Periodic Table of the Elements in Hawley's Condensed Chemical
  • the zeolite cracking bases which can be used as a component of the hydrocracking catalyst, can also be referred to as molecular sieves. These materials can be composed of silica, alumina and one or more exchangeable cations, such as sodium, magnesium, calcium, and one or more other metals such as transition and/or rare earth metals.
  • a large pore crystalline molecular sieve can be used.
  • the crystalline molecular sieve has a Constraint Index of less than 2, for example not more than 1. The method by which the Constraint Index is determined is fully described in U.S. Patent No. 4,016,218, which is incorporated herein by reference.
  • the hydrocracking catalyst can comprise a molecular sieve having a pore size of at least 7 angstroms, preferably at least 7.4 angstroms, for example at least 8 angstroms.
  • hydrocracking catalyst comprised of a molecular sieve having a pore size of not greater than 15 angstroms.
  • zeolite molecular sieves that can be used in the hydrocracking catalyst include, but are not limited to, Zeolite Beta, Zeolite X, Zeolite Y, faujasite, Ultrastable Y (USY), Dealuminized Y (Deal Y), Mordenite, ZSM-3, ZSM-4, ZSM-18, ZSM-20, and the like, and
  • the hydrocracking catalyst have at least some acidity.
  • the hydrocracking catalyst has an alpha value greater than 1 , more preferably greater than 5, for example greater than 10.
  • the alpha value is a measure of zeolite acidic functionality and an approximate indication of the catalytic cracking activity of a catalyst compared to a standard catalyst.
  • the alpha test is described in U.S. Patent No. 3,354,078 and in several articles in J.
  • Hydrocracking can be carried out under conditions effective for producing the desired fuel product.
  • the hydrocracking can be carried out at an average reaction temperature from 300°F (149°C) to 900°F (482°C), preferably from 550°F (289°C) to 800°F (427°C).
  • hydrocracking can also be carried out at an average reaction pressure from 400 psia (27 atm or 2.8 MPaa) to 3000 psia (200 atm or 21 MPaa), preferably from 500 psia (34 atm or 3.5 MPaa) to 2000 psia (140 atm or 14 MPaa).
  • the hydrogen containing treat gas rate in hydrocracking can range from 300 scf/bbl (53 Nm 3 /m 3 ) to 5000 scf/bbl (890 Nm 3 /m 3 ), for example from 2000 scf/bbl (360 NmV) to 4000 scf/bbl (710 Nm 3 /m 3 ).
  • Treat gas can be either pure hydrogen or a hydrogen-containing gas, which contains hydrogen in an amount at least sufficient for the intended reaction purpose(s), optionally in addition to one or more other gases (e.g., nitrogen, light hydrocarbons such as methane, and the like, and combinations thereof) that generally do not adversely interfere with or affect either the reactions or the products.
  • gases e.g., nitrogen, light hydrocarbons such as methane, and the like, and combinations thereof
  • the treat gas stream introduced into a reaction stage can preferably contain at least about 50 vol%, for example at least about 75 vol%, hydrogen.
  • V/V/Hr or Hr "1 ) volumes/volume/hour (V/V/Hr or Hr "1 ), will typically range from 0.1 to 10, preferably from 1 to 5.
  • reactors suitable for hydrocracking can include, but are not limited to, trickle bed, ebullating bed, moving bed, fluidized bed, and slurry reactors.
  • One or more fractions can be removed or recovered from the hydrocracked product as the fuel composition according to this invention.
  • the feedstock can be hydrocracked to produce the transportation fuel.
  • the transportation fuel can also be fractionated into at least one fractionated component, e.g., selected from the group consisting of gasoline, kerosene, jet fuel, diesel, and combinations thereof.
  • the process can be carried out to produce or recover a kerosene type or a gasoline type jet fuel.
  • the process can be carried out to produce or recover a kerosene type jet fuel having an ASTM D86 90% distillation point within the range from 250°C to 290°C, preferably from 260°C to 280°C.
  • the process can be carried out to produce or recover a gasoline type jet fuel having an ASTM D86 90% distillation point within the range from 200°C to 240°C, preferably from 210°C to 230°C.
  • the process can be carried out to produce or recover a kerosene type jet fuel having an ASTM D86 10% distillation point within the range from 150°C to 200°C, preferably from 160°C to 180°C.
  • the process can be carried out to produce or recover a gasoline type jet fuel having an ASTM D86 10% distillation point within the range from 110°C to 140°C, preferably from 120°C to 130°C.
  • the process can be carried out to produce or recover diesel fuel, e.g., having an ASTM D86 90% distillation point within the range from 260°C to 350°C, preferably from 280°C to 340°C.
  • the process can be carried out to produce or recover diesel fuel having an ASTM D86 10% distillation point within the range from 200°C to 240°C, preferably from 210°C to 230°C.
  • the present invention includes the following embodiments.
  • Embodiment 1 A method of producing transportation fuel, comprising: providing a feedstock containing lipid material and mineral oil, wherein the lipid material is selected from the group consisting of triglycerides, fatty acid alkyl esters, and combinations thereof; and hydrocracking the feedstock to produce the transportation fuel.
  • Embodiment 2 The method of embodiment 1 , wherein the mineral oil is comprised of straight run gas oils, vacuum gas oils, demetallized oils, coker distillates, cat cracker distillates, heavy naphthas, diesel boiling range distillate fraction, jet fuel boiling range distillate fraction, kerosene boiling range distillate fraction, coal liquids, or a combination thereof.
  • Embodiment 3 The method of embodiment 1 or embodiment 2, wherein the feedstock has an initial boiling point of at least 100°C, a final boiling point of not greater than 500°C, or both.
  • Embodiment 4 The method of any of the previous
  • the feedstock includes not greater than 99 wt% mineral oil, based on total weight of the feedstock.
  • Embodiment 6 The method of any of the previous
  • the lipid material portion of the feedstock includes triglyceride and a majority of the triglyceride present in the lipid material is comprised of C 8 to C 22 fatty acid constituents, based on total triglyceride present in the lipid material.
  • Embodiment 7 The method of any of the previous
  • the lipid material portion of the feedstock is comprised of at least 20 wt% fatty acid alkyl ester, based on total weight of the lipid material in the feedstock.
  • the transportation fuel is recovered as at least one fractionated component selected from the group consisting of gasoline, kerosene, jet fuel, and diesel.
  • Embodiment 9 The method of any of the previous

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Abstract

La présente invention concerne des procédés de production d'une composition de carburant d'une charge qui comprend une substance lipidique (par exemple, un biomatériau) et une huile minérale. Les procédés peuvent être réalisés sans produire de réactions secondaires significatives telles que le craquage, la polymérisation, et l'aromatisation, qui peuvent être une conséquence indésirable des grandes chaleurs de réaction. En résultat, l'invention concerne la production d'un produit d'une relativement grande qualité, et un catalyseur utilisé dans les procédés n'est pas affecté de manière néfaste à un degré significatif.
PCT/US2010/049614 2009-09-25 2010-09-21 Production de carburant à partir d'une charge contenant un triglycéride et/ou un alkyl ester d'acide gras WO2011037901A2 (fr)

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JP2012530965A JP2013506031A (ja) 2009-09-25 2010-09-21 トリグリセリドおよび／または脂肪酸アルキルエステルを含有する原料油からの燃料製造
CN2010800420525A CN102510893A (zh) 2009-09-25 2010-09-21 从含有甘油三酸酯和/或脂肪酸烷基酯的原料生产燃料
EP10819319.4A EP2480638A4 (fr) 2009-09-25 2010-09-21 Production de carburant à partir d'une charge contenant un triglycéride et/ou un alkyl ester d'acide gras
CA2772939A CA2772939A1 (fr) 2009-09-25 2010-09-21 Production de carburant a partir d'une charge contenant un triglyceride et/ou un alkyl ester d'acide gras
AU2010298473A AU2010298473A1 (en) 2009-09-25 2010-09-21 Fuel production from feedstock containing triglyceride and/or fatty acid alkyl ester
SG2012013165A SG178874A1 (en) 2009-09-25 2010-09-21 Fuel production from feedstock containing triglyceride and/or fatty acid alkyl ester

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SG178874A1 (en) 2012-04-27
CN102510893A (zh) 2012-06-20
EP2480638A2 (fr) 2012-08-01
EP2480638A4 (fr) 2013-07-03
CA2772939A1 (fr) 2011-03-31
JP2013506031A (ja) 2013-02-21
US20110072715A1 (en) 2011-03-31
WO2011037901A3 (fr) 2011-07-21
SG10201405735YA (en) 2014-11-27
AU2010298473A1 (en) 2012-04-19

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