JP2020015778A - バイオ燃料の製造方法 - Google Patents
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- 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
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- 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
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/1802—Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
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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
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
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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
- C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
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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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- 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
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- 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
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- Crystallography & Structural Chemistry (AREA)
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Abstract
Description
図1は、バッチ式反応装置の概略図であり、反応器の外周にはヒータが設けられ、反応器内には触媒とともに原料油とアルコールが収納される。反応は反応器内の温度・反応試料の撹拌速度をコントローラで制御する下で、行われる。
<アルミニウム挿入SBA−15(Al−SBA−15(5))>
本発明において使用される固体酸触媒の一例として、以下のようにメソポーラスシリカ(SBA−15)に適量のアルミニウムを導入した触媒を調製した。ポリマーP123を塩酸で溶解させ、TEOS(Tetraethyl Orthoslilcate)と混合させた。そして、この混合物に、アルミニウムとシリコンの原子比を5になるように、適量の硫酸アルミニウム塩の塩酸溶液を加えた後、アンモニア水で中和し、アルミニウムをSBA−15に導入する。そして、シリカの結晶を成長させ、ポリマーP123等を450℃で空気中焼成によって除去し、アルミニウム挿入SBA−15(Al−SBA−15(5)を得た。また、硫酸アルミニウム塩の添加量を変えれば、アルミニウムとシリコンの原子比が異なるAl−SBA−15も調製される。
本発明において使用される固体酸触媒の一例として、以下のように硫酸化ジルコニアを調製した。酸化ジルコニアとして(JRC-ZRO-2〜5)を使用し、その粒径32〜50メッシュに粉砕した。その後、コニカルビーカに上記酸化ジルコニアを2g採取し、0.5モル/リットルの硫酸水溶液中に溶解させ、分散させ1時間放置後、10分程度吸引ろ過し、硫酸化ジルコニアを得た。さらに、上記操作により得られた硫酸化ジルコニアを30℃にて、24時間乾燥し、その後るつぼを用いて、600℃にて3時間、空気中にて焼成し、固体酸を調製した。また、硫酸の代わりに硝酸または塩酸を使用した場合、硝酸ジルコニアや塩酸ジルコニアが調製される。
表1中、Amberlyst 70は比較例として提示された陽イオン交換樹脂類の市販固体酸触媒である。
B2O3系固体酸触媒、メソポーラスシリカSBA-15にアルミニウムを導入したAl-SBA-15系固体酸触媒について原料油中の遊離脂肪酸の高い転化率が得られる。
メゾポーラスシリカにアルミニウムを一部導入したSiO2/Al2O3系固体酸触媒(Al-SBA-15)を図2に示す流通式反応装置の反応器に充填し、原料油と低級アルコールを送入してエステル化反応を行わせた。その結果所定の効果を挙げることができた。
Claims (4)
- 固体酸触媒の存在下で遊離脂肪酸を含む油脂と低級アルコールを反応させるバイオ燃料の製造方法において、遊離脂肪酸と低級アルコールとの モル比が6以下で行って、遊離脂肪酸と低級アルコールとのエステル化を優先的に行わせるにしたバイオ燃料の製造方法。
- 遊離脂肪酸と低級アルコールとのモル比が1〜4である請求項1のバイオ燃料の製造方法。
- 固体酸触媒としてSiO2/Al2O3系固体酸触媒、メソポーラスシリカにアルミニウムを一部導入したSiO2/Al2O3系固体酸触媒、Al2O3/B2O3系固体酸触媒、硫酸化ジルコニア系固体酸触媒から選択された触媒を使用する請求項1又は請求項2記載のバイオ燃料の製造方法
- 反応温度が150℃以下である請求項1〜請求項3記載のバイオ燃料の製造方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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JP2018137583A JP6770554B2 (ja) | 2018-07-23 | 2018-07-23 | バイオ燃料の製造方法 |
PCT/JP2019/028091 WO2020022143A1 (ja) | 2018-07-23 | 2019-07-17 | バイオ燃料の製造方法 |
EP19841147.2A EP3828252B1 (en) | 2018-07-23 | 2019-07-17 | Method for producing biofuel |
CN201980047849.5A CN112585247B (zh) | 2018-07-23 | 2019-07-17 | 生物燃料的制造方法 |
US17/262,344 US11427776B2 (en) | 2018-07-23 | 2019-07-17 | Method for producing biofuel |
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JP2018137583A JP6770554B2 (ja) | 2018-07-23 | 2018-07-23 | バイオ燃料の製造方法 |
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JP2020015778A true JP2020015778A (ja) | 2020-01-30 |
JP6770554B2 JP6770554B2 (ja) | 2020-10-14 |
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US (1) | US11427776B2 (ja) |
EP (1) | EP3828252B1 (ja) |
JP (1) | JP6770554B2 (ja) |
CN (1) | CN112585247B (ja) |
WO (1) | WO2020022143A1 (ja) |
Families Citing this family (3)
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JP7045775B2 (ja) * | 2019-11-29 | 2022-04-01 | 国立大学法人東京農工大学 | 流通式反応装置を用いたバイオ燃料の製造方法 |
WO2021106619A1 (ja) * | 2019-11-29 | 2021-06-03 | 富士通商株式会社 | 流通式反応装置を用いたバイオ燃料の製造方法 |
CN113385198B (zh) * | 2021-07-07 | 2022-08-05 | 太原理工大学 | 有序介孔硫酸化锆—铝复合氧化物固体酸材料及其制备和应用 |
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KR20040087625A (ko) * | 2003-04-08 | 2004-10-14 | 한국에너지기술연구원 | 폐식용유중의 유리지방산 제거방법 |
WO2004096962A1 (en) * | 2003-04-29 | 2004-11-11 | Escola De Química/Ufrj | Catalytic process to the esterification of fatty acids present in the acid grounds of the palm using acid solid catalysts |
WO2009016646A1 (en) * | 2007-08-01 | 2009-02-05 | Council Of Scientific & Industrial Research | Novel glycerol-based heterogeneous solid acid catalysts useful for the esterification of fatty acids, a process and use thereof |
EP2316913A1 (en) * | 2009-10-29 | 2011-05-04 | Malaysian Palm Oil Board | A Method Of Converting Free Fatty Acid (FFA) From Oil To Methyl Ester |
JP2011167677A (ja) * | 2010-02-22 | 2011-09-01 | Korea Inst Of Energy Research | タングステンオキサイドアルミナ触媒の製造方法、その方法によって製造されたタングステンオキサイドアルミナ触媒及びその触媒を用いて遊離脂肪酸が含まれた廃食用油から遊離脂肪酸を除去する方法 |
JP2013159685A (ja) * | 2012-02-03 | 2013-08-19 | Mitsubishi Chemicals Corp | 脂肪酸エステルの製造方法及びバイオディーゼル燃料 |
WO2013137286A1 (ja) * | 2012-03-13 | 2013-09-19 | 株式会社ダイキアクシス | 固体酸触媒、その製造方法及びそれを用いた脂肪酸アルキルエステルの製造方法 |
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2018
- 2018-07-23 JP JP2018137583A patent/JP6770554B2/ja active Active
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2019
- 2019-07-17 US US17/262,344 patent/US11427776B2/en active Active
- 2019-07-17 CN CN201980047849.5A patent/CN112585247B/zh active Active
- 2019-07-17 EP EP19841147.2A patent/EP3828252B1/en active Active
- 2019-07-17 WO PCT/JP2019/028091 patent/WO2020022143A1/ja unknown
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Non-Patent Citations (1)
Title |
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Publication number | Publication date |
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JP6770554B2 (ja) | 2020-10-14 |
CN112585247A (zh) | 2021-03-30 |
US20210214625A1 (en) | 2021-07-15 |
EP3828252A4 (en) | 2022-04-20 |
CN112585247B (zh) | 2023-08-25 |
WO2020022143A1 (ja) | 2020-01-30 |
EP3828252B1 (en) | 2024-03-06 |
EP3828252C0 (en) | 2024-03-06 |
EP3828252A1 (en) | 2021-06-02 |
US11427776B2 (en) | 2022-08-30 |
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