WO2013073528A1 - 燃料油の製造方法 - Google Patents
燃料油の製造方法 Download PDFInfo
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- WO2013073528A1 WO2013073528A1 PCT/JP2012/079412 JP2012079412W WO2013073528A1 WO 2013073528 A1 WO2013073528 A1 WO 2013073528A1 JP 2012079412 W JP2012079412 W JP 2012079412W WO 2013073528 A1 WO2013073528 A1 WO 2013073528A1
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- fatty acid
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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
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
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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
-
- 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
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- 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
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- 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
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- 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
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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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
- C10L2200/0484—Vegetable or animal oils
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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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
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- 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
- the present invention relates to a method for producing fuel oil, particularly fuel oil useful as aircraft fuel oil, from fatty acid triglycerides.
- Biofuels produced from biomass-based raw materials include bioalcohol fuels obtained by direct fermentation of carbohydrates contained in sugarcane, corn, etc., or by fermentation of carbohydrates obtained by decomposing cellulose contained in thinned wood, etc.
- Biodiesel fuel (BDF) and the like using fatty acid methyl esters obtained by transesterification of animal and vegetable fats and oils as fuel oils are known.
- bioalcohol fuel made from sugarcane, corn, etc. has an impact on the stable supply of food, requires a lot of energy to remove water, and is difficult to apply to aviation fuel. There are challenges.
- Bioalcohol fuel using cellulose as a raw material has problems such as high production cost and difficulty in application to aviation fuel.
- biodiesel fuel is used by being added to or mixed with conventional petroleum-based fuels (see, for example, Patent Document 1), it is still insufficient as a complete alternative technology for petroleum-based raw materials, and by oxidation. There are also problems such as deterioration and low-temperature solidification. In addition, the high cost of production due to the treatment of by-produced glycerin and the cleaning of the product oil is an obstacle to popularization in the transportation industry where price competition is becoming increasingly intense. Furthermore, since the fatty acid group which comprises fats and oils has too many carbon numbers or it is linear, the subject that a sufficient octane number cannot be obtained as it is also exists.
- biohydrocracking which is obtained by a process of decomposing animal and vegetable oils in the presence of hydrogen gas or a catalyst using a vacuum gas oil hydrocracking apparatus or the like, and mainly contains a hydrocarbon compound.
- Fuel (BHF) has been proposed.
- reactions such as reduction of the carboxyl group, shortening of the hydrocarbon chain, isomerization of the straight chain alkyl group to the branched chain alkyl group, and the like consist of a hydrocarbon compound having a desired carbon number or branch A mixture is obtained (see, for example, Patent Documents 2 to 7).
- the present invention has been made in view of such circumstances, and while reducing the hydrogen pressure, a fuel oil or a raw material mainly composed of n-paraffin or isoparaffin from a raw material oil containing a fatty acid triglyceride or its raw material is inexpensive and has a high yield. It aims at providing the manufacturing method of the raw material oil which can be manufactured easily.
- [2] The method for producing fuel oil according to [1], wherein the hydrogen pressure is 1 MPa or less. [3] The method for producing fuel oil according to the above [1] or [2], wherein the metal element is nickel and / or cobalt. [4] The method for producing fuel oil according to [3], wherein the metal element is nickel and the group 6 element is molybdenum. [5] The method for producing fuel oil according to any one of [1] to [4], wherein the porous metal oxide support is ⁇ -alumina or a modified product thereof. [6] The raw material oil, hydrogen gas, and the catalyst, 6.
- n-paraffin and isoparaffin used as a raw material for fuel oil are obtained by hydrocracking fatty acid triglycerides contained in the raw oil under a hydrogen pressure of 2 MPa or less, preferably 1 MPa or less.
- Fuel oil containing the main component can be manufactured at low cost and in high yield. Therefore, high-grade fuel oil can be produced at low cost from carbon-neutral raw materials such as vegetable oils and fats. Therefore, it is possible to provide a powerful alternative to conventional fossil fuel-derived fuel oil, and as a result, present effective solutions for environmental problems such as depletion of fossil fuels and reduction of greenhouse gases typified by carbon dioxide. Is.
- porous metal oxide carrier there can be used alumina or a material containing a composite oxide such as silica containing alumina as a main component.
- alumina or modified alumina containing alumina as a main component is preferable.
- porous ⁇ -alumina ⁇ -Al 2 O 3
- ⁇ -alumina, ⁇ -alumina, amorphous alumina, and the like may be used.
- Alumina which is the main component of the carrier, is a method of heat-treating aluminum hydroxide obtained by neutralizing an aluminum salt with an alkali, a method of neutralizing or hydrolyzing an aluminum salt and an aluminate, or an aluminum amalgam or aluminum alcoholate. It may be produced by using any of the methods for hydrolyzing, and in addition to these methods, it may be produced using a commercially available alumina intermediate or boehmite powder as a precursor.
- the porous inorganic oxide carrier is silica (SiO 2 ), silica-alumina (SiO 2 / Al 2 O 3 ), boria (B 2 O 3 ), titania (TiO 2 ), magnesia (MgO).
- Activated carbon, diphosphorus pentoxide (P 2 O 5 ) or a composite oxide thereof may be included.
- the porous inorganic oxide support may contain zeolite as silica-alumina (SiO 2 / Al 2 O 3 ).
- Zeolite is a generic name for aluminosilicates with fine pores in the crystal. Specific examples include amysite (monoclinic), ammonium leucite, arsenite, barrel zeolite, berbergate, biquitite, bogsite.
- zeolite when used as the porous metal oxide support, its structure is not particularly limited, and may be, for example, Y-type zeolite, X-type zeolite, beta-type zeolite, ZSM-5 zeolite, etc. The mixture containing 2 or more of these may be sufficient.
- Group 9 or Group 10 of the periodic table means Group 9 or Group 10 of the long-period type (IUPAC format) periodic table, respectively.
- metal elements belonging to these groups are as follows. , Cobalt (Co), nickel (Ni), rhodium (Rh), palladium (Pd), iridium (Ir) and platinum (Pt). Of these metal elements, cobalt and nickel are preferable in terms of catalytic activity, cost, and the like, and nickel is particularly preferable.
- the catalyst contains one of these metals or any two or more of them in an arbitrary ratio, and these are supported on the surface of the porous metal oxide support in the form of metal.
- Group 6 of the periodic table means Group 6 of the long-period type (IUPAC format) periodic table, and specific examples of elements belonging to these groups (referred to as “Group 6 elements” in the present invention). These include chromium (Cr), molybdenum (Mo) and tungsten (W). Of these, molybdenum and tungsten are preferred, and molybdenum is particularly preferred.
- the catalyst contains one of these metals or any two or more of them in an arbitrary ratio, and these are supported on the surface of the porous metal oxide support in the form of an oxide.
- the metal element belonging to Group 9 or Group 10 of the periodic table has catalytic activity for the hydrocracking reaction of fatty acid triglycerides contained in the feedstock, and the oxide of the element belonging to Group 6 of the periodic table is It is thought that it contributes to imparting basicity to the catalyst and improving the dispersibility of the metal.
- the weight ratio of the Group 6 element to the metal element belonging to Group 9 or Group 10 of the periodic table does not exceed 1.0 in terms of metal. That is, when the weight of the metal element belonging to Group 9 or Group 10 of the periodic table is w 1 and the metal equivalent weight of the Group 6 element is w 2 , (w 2 / w 1 ) ⁇ 1.
- a preferable range of w 2 / w 1 is 0.05 or more and 1.0 or less, more preferably 0.1 or more and 0.7 or less, and further preferably 0.15 or more and 0.5 or less.
- the catalyst impregnates a porous metal oxide support with an aqueous solution containing a salt of a Group 6 element and an aqueous solution containing a salt of a metal belonging to Group 9 or Group 10 of the periodic table, and performs a hydrogen reduction treatment after firing. It is manufactured by.
- the salt used in the production of the catalyst is not particularly limited as long as it has water solubility, and includes inorganic acid salts such as nitrates, halide salts, sulfates and phosphates, and organic acid salts such as carboxylates. Can be used.
- a polyacid salt or a heteropolyacid salt which is available at a relatively low cost is preferably used.
- the salt of the Group 6 element and the salt of the metal belonging to Group 9 or Group 10 of the periodic table may be supported at the same time by impregnating an aqueous solution containing both, followed by firing and hydrogen reduction treatment.
- One of them may be impregnated, and after calcination and hydrogen reduction, the other may be impregnated to perform calcination and hydrogen reduction.
- the hydrogen reduction treatment may be performed after the impregnation and the firing are sequentially performed.
- any animal or vegetable oil containing fatty acid triglyceride as a main component can be used without particular limitation.
- the fatty acid group composition (carbon number and degree of unsaturation of fatty acid groups) of the fatty acid triglyceride contained in the feedstock oil affects the carbon number and content of each hydrocarbon compound constituting the resulting fuel oil.
- An appropriate raw material oil can be appropriately selected and used according to the performance and the number of carbons required for the fuel oil.
- fats and oils used as raw material oil include corn oil, soybean oil, sesame oil, rapeseed oil (canola oil), rice oil, cocoon oil, cocoon oil, safflower oil cocoon (safflower oil), palm kernel oil, coconut oil, cottonseed oil, Sunflower oil, camellia oil, olive oil, peanut oil, almond oil, avocado oil, hazelnut oil, walnut oil, grape seed oil, mustard oil, lettuce oil, cacao butter, palm oil, seaweeds and microalgae Vegetable oils such as fats and oils to be produced, animal oils such as fish oil, whale oil, shark oil, liver oil, lard (pig fat), het (beef tallow), chicken oil, rosin, sheep fat, horse fat, milk fat, butter Examples include fats and oils produced by bacteria.
- microalgae that can be used as a source of raw material oil
- examples of microalgae that can be used as a source of raw material oil include Botryococcus braunii, Chlorella, Aurantiochytrium, and the like.
- a raw material oil derived from microalgae mainly composed of fatty acid triglycerides having a saturated fatty acid group content of 8 to 14 carbon atoms in the fatty acid group composition of fatty acid triglycerides suitable for the production of aviation fuel oils For example, fats and oils derived from microalgae deposited under the deposit number FERM P-22090 can be mentioned.
- aviation fuels must be composed mainly of n-paraffins and isoparaffins having about 8 to 14 carbon atoms and have excellent low-temperature characteristics (clouding point, solidification temperature).
- a raw material oil for efficiently producing a fuel oil capable of satisfying such requirements the content of saturated fatty acid groups having 8 to 14 carbon atoms in the fatty acid group composition of the fatty acid triglyceride contained in the raw material oil is 40.
- a raw material oil containing fatty acid triglyceride as a main component in an amount of not less than wt% is preferable, and among these, an oil having a lauric acid group content of not less than 40 wt% is particularly preferable.
- specific examples of preferable raw material for aviation fuel include coconut oil collected from coconut seeds and palm kernel oil collected from oilseed seeds, algae, especially fine Examples include fats and oils collected from algae and the like.
- the free fatty acid in the raw oil is high, pretreatment to remove the free fatty acid may be performed if necessary.
- the free fatty acid is carbonized by hydrogenation. Since it is also possible to convert to hydrogen, raw material oil containing free fatty acid may be used as it is.
- a fuel oil can be efficiently obtained under a low hydrogen pressure of 2 MPa or less, preferably 1 MPa or less and a relatively low reaction temperature of 250 to 400 ° C. Since the hydrogen pressure can be lowered, there is no need to use a reaction vessel with high pressure resistance, and it is relatively less susceptible to hydrogen embrittlement in a metal reaction vessel. This makes it possible to produce fuel oil at low cost.
- the liquid space velocity (LHSV) during the reaction is, for example, 0.5 to 20 hr ⁇ 1
- the hydrogen / oil ratio is, for example, 50 to 4000 NL / L.
- the fuel oil thus obtained is mainly composed of n-paraffin having a carbon number substantially equal to the carbon number of the fatty acid group contained in the raw material oil.
- the isomerization treatment may be performed using any known catalyst such as a platinum catalyst or a solid acid catalyst.
- ⁇ -alumina or the like is used as the porous metal oxide support, it acts as a solid acid catalyst, so that isomerization proceeds at the same time, and formation of isoparaffin may be observed.
- the time required for the isomerization step necessary to improve the content of isoparaffin can be shortened, and in some cases, the isomerization step can be omitted. Therefore, especially when it is necessary to improve the content of isoparaffin, the production cost of fuel oil can be reduced.
- fuel oil can be obtained by adding an appropriate amount of additives such as antioxidants and antifreeze agents.
- additives such as antioxidants and antifreeze agents.
- coconut oil or oils and fats derived from microalgae are used as raw material oil, fuel oil that satisfies the requirements for aviation oil fuel defined in ASTM D 7566 and the like can be obtained.
- the main standards for aviation turbine fuel oils containing synthetic hydrocarbons as defined in ASTM D 7566 are: ⁇ Hydrocarbon oil: 99.5% or more ⁇ Cycloparaffin 15% or less ⁇ Paraffin hydrocarbon oil: 70% to 85% ⁇ Olefin hydrocarbon: 5% or less ⁇ Aromatic compound: 0.5% or less ⁇ Acidity: 0.10 mgKOH / g or less ⁇ Sulfur compound: 3 ppm or less
- Example 1 Preparation of Catalyst ⁇ 1> Preparation of ⁇ -Al 2 O 3 Support A 3900 cc aqueous solution of aluminum nitrate having a concentration of 2.67 mol / L was prepared and 3900 cc of an aqueous ammonia solution having a concentration of 14% by weight were prepared. Next, 20 L of pure water was put into a 30 L enamel container, heated to 70 ° C. while stirring, and further stirred, the above-mentioned aluminum nitrate aqueous solution 650 cc was added and stirred for 5 minutes (pH value: 2.
- the obtained ⁇ -alumina support has a surface area of 275 m 2 / g, a pore volume of 0.65 cc / g, an average pore diameter of 8.9 nm (89 mm), and an average pore diameter of ⁇ 3 nm (30 mm) with respect to the total pore volume. ) was 91%.
- the pore diameter distribution of the ⁇ -alumina support obtained by the above method was very small, and it was confirmed that it had a porous structure with uniform pore diameters.
- hydrocracking catalyst (1) Using the above porous inorganic oxide carrier, 97 cc of a nickel nitrate aqueous solution prepared to a concentration of 0.5 mol / L was impregnated with 100 g of the porous inorganic oxide carrier and allowed to stand in a sealed container for 12 hours. Thereafter, moisture was removed at room temperature with an evaporator and fired in an electric furnace at 200 ° C. for 3 hours in air to obtain each fired product in which nickel (Ni) was supported on a porous inorganic oxide carrier. . Next, each fired product was filled in a flow-type hydrogen reduction device, and hydrogen reduction was performed under conditions of 370 ° C. and 15 hours under a hydrogen stream to obtain a hydrocracking catalyst (1).
- hydrocracking catalyst (2) An aqueous solution obtained by dissolving 7.19 g of ammonium molybdate [(NH 4 ) 6 Mo 7 O 24 ⁇ 4H 2 O] in 65.92 cc of pure water with respect to 100 g of the hydrocracking catalyst (1) obtained above. After impregnating for 12 hours in an airtight container, moisture is removed at room temperature with an evaporator, and fired in an electric furnace at 200 ° C. in air for 3 hours. The hydrocracking was charged in a hydrogen-reducing apparatus, and was hydrogen-reduced in a hydrogen stream at 370 ° C.
- Catalyst (2) was prepared.
- the nickel supported amount (Ni supported amount) in terms of metal Ni is 22% by weight
- the molybdic acid (MoO 3 ) supported amount (MoO 3 supported amount) is 5% by weight.
- hydrocracking catalyst (3) A solution prepared by dissolving 100 g of the hydrocracking catalyst (1) obtained above and 4.72 g of ammonium tungstate [5 (NH 4 ) 2 ⁇ 12WO 3 ⁇ 5H 2 O] in an aminoethanol aqueous solution (65.92 cc) was obtained. After impregnating and allowing to stand for 12 hours in an airtight container, moisture is removed at room temperature with an evaporator, and fired in an electric furnace at 200 ° C. in air for 3 hours. Hydrogenation in which hydrogen reduction apparatus is charged and hydrogen reduction is performed under conditions of 370 ° C.
- a cracking catalyst (3) was prepared.
- the nickel supported amount (Ni supported amount) in terms of metallic Ni is 15% by weight
- the tungstic acid (WO 3 ) supported amount is 5% by weight.
- Example 2 Production of fuel oil using coconut oil as feedstock
- Hybrid coconut oil used as feedstock is lauric acid (12: 0) 45-52 wt%, myristic acid (14: 0) 15-22 wt% , Caprylic acid (8: 0) 6-10 wt%, capric acid (10: 0) 4-12 wt%, stearic acid (18: 0) 1-5 wt%, oleic acid (18: 1) 2-10 % By weight, and linoleic acid (18: 2) 1 to 3% by weight were included as the main constituent fatty acid groups (note that the numbers in parentheses indicate the number of carbons: number of double bonds. The percentages are weight%.
- the conversion is almost 100% even in this reaction, and as shown in FIG. 2, the product is mainly C 11 hydrocarbons, and almost all of them are normal paraffins. there were.
- the yield of the obtained liquid hydrocarbon the aviation fuel fraction yield indicating the ratio of the aviation fuel fraction (C 7 to C 16 ) in the liquid hydrocarbon, and the average carbon number of the aviation fuel fraction
- the calculated results are shown in the following Table 1.
- the liquid hydrocarbon yield was 94.6%, and the aviation fuel fraction yield was very high at 89.7%, which was obtained from oils and fats derived from microalgae. It was confirmed that almost the same result as that obtained when fatty acid triglyceride was used as a raw material oil was obtained. Further, all of the cloud point, acidity, and sulfur compound content rate satisfied the standard of ASTM D 7566.
- Hydrocracking was performed under the same conditions as in Example 2 above, using fatty acid triglycerides derived from fine algal fats and oils as a raw material oil.
- Table 3 shows the conversion, paraffin and olefin content, liquid hydrocarbon yield, aviation fuel fraction yield and aviation fuel fraction average carbon number.
- Table 4 shows the measurement results of the carbon number distribution in the fuel oil.
- Example 3 fatty acid triglyceride collected by culturing the microalgae deposited under the deposit number FERM P-22090 was used as the raw material oil, but two or more known plants (algae containing microalgae, For example, a fatty acid triglyceride mixture having a fatty acid group composition as shown in Table 2 is prepared by blending oils and fats (fatty acid triglycerides) derived from bacteria in any ratio, and used as a raw material oil May be.
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Abstract
Description
さらに、油脂を構成する脂肪酸基の炭素数が多すぎたり、直鎖状であるために、そのままでは十分なオクタン価が得られない等の課題も存在する。
特許文献5記載の輸送燃料の製造についても、水素化処理は約0.7~約14MPaという高い水素圧力を必要とする。
[1] 脂肪酸トリグリセリドを含む原料油と、水素ガスとを、水素圧力2MPa以下の条件下で、周期表の第9族または第10族に属する1または複数の金属元素および周期表の第6族に属する1または複数の第6族元素酸化物を多孔質金属酸化物担体上に担持させた触媒と接触させ、n-パラフィンおよびイソパラフィンの一方または双方を主成分とする燃料油を製造する工程を有し、前記触媒に含まれる前記第6族元素の前記金属元素に対する重量比が、金属換算で1.0を超えない燃料油の製造方法。
[2] 前記水素圧力が1MPa以下である上記[1]記載の燃料油の製造方法。
[3] 前記金属元素がニッケルおよび/またはコバルトである上記[1]または[2]記載の燃料油の製造方法。
[4] 前記金属元素がニッケルであり、前記第6族元素がモリブデンである上記[3]記載の燃料油の製造方法。
[5] 前記多孔質金属酸化物担体がγ-アルミナまたはその修飾物である上記[1]から[4]のいずれか1項記載の燃料油の製造方法。
[6] 前記原料油と、水素ガスと、前記触媒とを、
液空間速度0.5~20hr-1、反応温度250~400℃の条件下で接触させる上記[1]から[5]のいずれか1項記載の燃料油の製造方法。
[7] 前記原料油に含まれる脂肪酸トリグリセリドの脂肪酸基組成における炭素数8~14の飽和脂肪酸基の含有量が40重量%以上であることを特徴とする上記[1]から[6]のいずれか1項記載の燃料油の製造方法。
[8] 前記脂肪酸トリグリセリドの脂肪酸基組成におけるラウリン酸の含有量が40重量%以上である上記[7]記載の燃料油の製造方法。
[9] 前記原料油が植物または細菌類由来の油脂である上記[1]から[8]のいずれか1項記載の燃料油の製造方法。
[10] 前記植物由来の油脂が、2種類以上の植物に由来する油脂の混合物である上記[9]記載の燃料油の製造方法。
[11] 前記植物由来の油脂がココナッツ油もしくはパーム核油または両者の混合物である上記[9]または[10]記載の燃料油の製造方法。
[12] 前記植物由来の油脂が藻類由来の油脂であることを特徴とする上記[9]または[10]記載の燃料油の製造方法。
[13] 得られた前記燃料油を主成分とする燃料油が、ASTM D 7566に規定された航空油燃料の要件を満たしている上記[1]から[12]のいずれか1項記載の燃料油の製造方法。
本発明の燃料油の製造方法の実施に用いられる触媒(以下、「触媒」と略称する。)は、周期表の第9族または第10族に属する1または複数の金属元素および周期表の第6族に属する1または複数の第6族元素の酸化物を多孔質金属酸化物担体上に担持させたものである。
・炭化水素油:99.5%以上
・シクロパラフィン15%以下
・パラフィン系炭化水素油:70%~85%
・オレフィン系炭化水素:5%以下
・芳香族系化合物:0.5%以下
・酸度:0.10mgKOH/g以下
・硫黄化合物:3ppm以下
実施例1:触媒の調製
<1>γ-Al2O3担体の調製
濃度2.67mol/Lの硝酸アルミニウム水溶液3900ccを調製すると共に、濃度14重量%のアンモニア水溶液3900ccを用意した。次に、30Lのホーロー容器に純水20Lを入れ、撹拌しながら70℃に加温し、更に撹拌を継続しながら、上記硝酸アルミニウム水溶液650ccを投入して5分間撹拌し(pH値:2.0)、次いで上記アンモニア水溶液650ccを投入して5分間撹拌する(pH値:7.4)pHスイング操作を6回繰り返し行った。得られた水酸化アルミニウムのスラリー水溶液を濾過してケーキを回収し、次いで、このケーキを純水20Lに再分散させて再び濾過する洗浄操作を3回繰り返し行い、水酸化アルミニウムの洗浄ケーキを得た。次に、洗浄ケーキを風乾して水分調整を行った後、押出成形機で直径1.6mmの棒状に成形し、120℃、3時間の条件で乾燥した後、長さ約1cm程度に粉砕し、マッフル炉にて500℃、3時間の条件で焼成してγ-アルミナ担体を得た。
上記の多孔質無機酸化物担体を使用し、0.5mol/Lの濃度に調製した硝酸ニッケル水溶液97ccに上記多孔質無機酸化物担体の100gを含浸して密閉容器中にて12時間静置した後、エバポレーターにて常温で水分を除去し、電気炉にて空気中200℃、3時間の条件で焼成し、多孔質無機酸化物担体にニッケル(Ni)が担持された各焼成物を得た。次に、これら各焼成物を流通式水素還元装置に充填し、水素気流下に370℃、15時間の条件で水素還元を行い、水素化分解触媒(1)を得た。
上記で得られた水素化分解触媒(1)を100gに対して、7.19gのモリブデン酸アンモニウム[(NH4)6Mo7O24・4H2O]を純水65.92ccに溶かした水溶液を含浸させ密閉容器中にて12時間静置した後、エバポレーターにて常温で水分を除去し、電気炉にて空気中200℃、3時間の条件で焼成し、次に、この焼成物を流通式水素還元装置に充填し、水素気流下に370℃、15時間の条件で水素還元してモリブデン酸(MoO3)が上記水素化分解触媒基準で5重量%の割合で添加された水素化分解触媒(2)を調製した。
得られた水素化分解触媒(2)における金属Ni換算のニッケル担持量(Ni担持量)は22重量%、及びモリブデン酸(MoO3)担持量(MoO3担持量)は5重量%である。
上記で得られた水素化分解触媒(1)を100gに、4.72gのタングステン酸アンモニウム[5(NH4)2・12WO3・5H2O]をアミノエタノール水溶液65.92ccに溶かした溶液を含浸させ密閉容器中にて12時間静置した後、エバポレーターにて常温で水分を除去し、電気炉にて空気中200℃、3時間の条件で焼成し、次に、この焼成物を流通式水素還元装置に充填し、水素気流下に370℃、15時間の条件で水素還元してタングステン酸(WO3)が水素化分解触媒(1)基準で5重量%の割合で添加された水素化分解触媒(3)を調製した。得られた水素化分解触媒(3)における金属Ni換算のニッケル担持量(Ni担持量)は15重量%、及びタングステン酸(WO3)担持量(WO3担持量)は5重量%である。
原料油として使用したハイブリッドココナッツ油は、ラウリン酸(12:0)45~52重量%、ミリスチン酸(14:0)15~22重量%、カプリル酸(8:0)6~10重量%、カプリン酸(10:0)4~12重量%、ステアリン酸(18:0)1~5重量%、オレイン酸(18:1)2~10重量%、リノール酸(18:2)1~3重量%を主な構成脂肪酸基として含んでいた(なお、括弧内の数字は、炭素数:二重結合数を示す。また、百分率は重量%である。以下同じ。)。このようなハイブリッドココナッツ油を原料油として、下記の条件下で水素化分解を行った。
・反応温度:350oC
・LHSV:1.0h-1
・反応圧力:0.8MPa
・H2/脂肪酸トリグリセリドの流量比=1250NL/L
・触媒量:2.0mL
・触媒粒径:355~600μm
なお、使用した触媒は上記実施例1の<3>で調製した水素化分解触媒(2)であり、前処理として370℃、GHSV=5000h-1で7時間水素還元処理を行った。反応時間と転化率の関係を図1に、得られた炭化水素の炭素数分布を図2にそれぞれ示す。
受託番号FERM P-22090として寄託された微細藻類を培養し、採取した脂肪酸トリグリセリドの脂肪酸基組成(メタノールを用いたエステル交換法により生成した脂肪酸メチルエステルのGC/MS分析により分析した。)は、下記の表2に示すとおりであり、脂肪酸基組成におけるラウリン酸(C11H23COOH)基の占める割合が40重量%以上であることがわかる。
Claims (13)
- 脂肪酸トリグリセリドを含む原料油と、
水素ガスとを、
水素圧力2MPa以下の条件下で、周期表の第9族または第10族に属する1または複数の金属元素および周期表の第6族に属する1または複数の第6族元素の酸化物を多孔質金属酸化物担体上に担持させた触媒と接触させ、n-パラフィンおよびイソパラフィンの一方または双方を主成分とする燃料油を製造する工程を有し、
前記触媒に含まれる前記第6族元素の前記金属元素に対する重量比が、金属換算で1.0を超えないことを特徴とする燃料油の製造方法。 - 前記水素圧力が1MPa以下であることを特徴とする請求項1記載の燃料油の製造方法。
- 前記金属元素がニッケルおよび/またはコバルトであり、前記第6族元素がモリブデンおよび/またはタングステンであることを特徴とする請求項1または2記載の燃料油の製造方法。
- 前記金属元素がニッケルであり、前記第6族元素がモリブデンであることを特徴とする請求項3記載の燃料油の製造方法。
- 前記多孔質金属酸化物担体がγ-アルミナまたはその修飾物であることを特徴とする請求項1から4のいずれか1項記載の燃料油の製造方法。
- 前記原料油と、水素ガスと、前記触媒とを、
液空間速度0.5~20hr-1、反応温度250~400℃の条件下で接触させることを特徴とする請求項1から5のいずれか1項記載の燃料油の製造方法。 - 前記原料油に含まれる脂肪酸トリグリセリドの脂肪酸基組成における炭素数8~14の飽和脂肪酸基の含有量が40重量%以上であることを特徴とする請求項1から6のいずれか1項記載の燃料油の製造方法。
- 前記脂肪酸トリグリセリドの脂肪酸基組成におけるラウリン酸基の含有量が40重量%以上であることを特徴とする請求項7記載の燃料油の製造方法。
- 前記原料油が植物または細菌類由来の油脂であることを特徴とする請求項1から8のいずれか1項記載の燃料油の製造方法。
- 前記植物由来の油脂が、2種類以上の植物に由来する油脂の混合物であることを特徴とする請求項9記載の燃料油の製造方法。
- 前記植物由来の油脂がココナッツ油もしくはパーム核油または両者の混合物であることを特徴とする請求項9または10記載の燃料油の製造方法。
- 前記植物由来の油脂が藻類由来の油脂であることを特徴とする請求項9または10記載の燃料油の製造方法。
- 得られた前記燃料油を主成分とする燃料油が、ASTM D 7566に規定された航空油燃料の要件を満たしていることを特徴とする請求項1から12のいずれか1項記載の燃料油の製造方法。
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JP2011148909A (ja) * | 2010-01-21 | 2011-08-04 | Tokyo Univ Of Agriculture & Technology | バイオ炭化水素、バイオ炭化水素の製造方法、およびバイオ炭化水素製造装置 |
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WO2015022561A1 (ja) * | 2013-08-15 | 2015-02-19 | エヌエスエックス グローバル プロプライアタリー リミティド | 新規微細藻類及びこれを用いたバイオ燃料の産生方法 |
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JPWO2020090141A1 (ja) * | 2018-10-30 | 2021-09-24 | 株式会社レボインターナショナル | 液体炭化水素燃料の製造方法 |
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US20140357924A1 (en) | 2014-12-04 |
JPWO2013073528A1 (ja) | 2015-04-02 |
CA2854709A1 (en) | 2013-05-23 |
SG11201402172YA (en) | 2014-09-26 |
BR112014011647A2 (pt) | 2017-05-02 |
EP2781579A1 (en) | 2014-09-24 |
KR20140107208A (ko) | 2014-09-04 |
IL232481A0 (en) | 2014-06-30 |
CN104039929A (zh) | 2014-09-10 |
JP5920672B2 (ja) | 2016-05-25 |
PH12014501132A1 (en) | 2014-07-28 |
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