JP2010506960A - グリセロールホルマールの脂肪酸エステルの製造およびそのバイオ燃料としての使用 - Google Patents
グリセロールホルマールの脂肪酸エステルの製造およびそのバイオ燃料としての使用 Download PDFInfo
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- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
- C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
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- C—CHEMISTRY; METALLURGY
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
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- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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- 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
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
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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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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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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- 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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- 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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- 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
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Abstract
Description
成分(I)および(II):
(式中、Rは脂肪酸のアルキル鎖である)
の総含有量が85質量%以上であるバイオ燃料の製造方法であって、(a)動物または植物を起源とする油脂のトリグリセリドと、グリセロールホルマールとの間のエステル交換反応を、酸または塩基の存在下において行う工程、(b)バイオ燃料である上側層から下側層を除去する工程、および(c)所望により、工程(b)で得たバイオ燃料を水で洗浄し、かつ乾燥させる工程を含む、方法に関する。これに代わる方法では、動物または植物を起源とする油脂のトリグリセリドを加水分解処理(一般的に油脂分解と呼ばれる)にかけて、脂肪酸およびグリセロールを形成し、続いて得られた脂肪酸をグリセロールホルマールとともに、酸または塩基の存在下においてエステル化することを包含する。
グリセロールホルマール溶液(3557.4g、 34.2mol)および水酸化ナトリウム(14.3g、0.21mol)を菜種油(262.5g、0.28mmol)に加える。この混合物を70℃に加熱し、250rpmで16時間攪拌する。続いて、混合物を30℃に冷却し、水を粗製反応物に、2層が完全に分離するまで加える。極性層をpH7に中和し、過剰のグリセロールホルマールを減圧下で蒸留して、循環使用する。蒸留されなかった、遊離グリセロールを含む画分をホルムアルデヒドと酸触媒の存在下において反応させて、グリセロールホルマールを再生する。グリセロールホルマールエステルを含む非極性層(上側層)を分離し、H2SO45%水溶液(312.3ml)で洗浄する。その後、有機層を水でpH7になるまで洗浄する。生成物を無水Na2SO4で除湿し、濾別し、最後に残留水を減圧下で留別し、標題化合物254gを得る。生成物は透明の黄色液体である。1H−NMR(CDCl3、400MHz):δ0.87(t,3H,CH2CH3)、1.29(m,17.3H,CH2)、1.63(m,2H,CH2CH2CH2CO)、2.02(m, 2H,CH2CH2CH=CH)、2.36(t,2H, CH2CH2CO)、2.77(m,0.86H,CH=CHCH2CH=CH)、5.025−3.65(m,7H,アセタール)y 5.33(m,2.83H,CH=CH)。
グリセロールホルマールを、菜種油、ヒマワリ油、またはパーム油に由来するバイオディーゼルと、20%比率(w/w)で混合した時の混和性を、表2において、2種類の異なった温度で比較する。
三元混合物バイオディーゼル/グリセロールホルマール/グリセロールホルマールエステルの混和性を、異なった脂肪酸源および異なった温度で評価した。結果を表3に示す。
Claims (15)
- 成分(I)および(II):
の総含有量が85質量%以上であるバイオ燃料の製造方法であって、
(a)動物または植物を起源とする油脂のトリグリセリドと、グリセロールホルマールとの間のエステル交換反応を、酸または塩基の存在下において行う工程、
(b)前記バイオ燃料である上側層から下側層を除去する工程、および
(c)所望により、工程(b)で得た前記バイオ燃料を水で洗浄し、かつ乾燥させる工程
を含むか、あるいは
動物または植物を起源とする油脂のトリグリセリドを加水分解処理にかけ、脂肪酸およびグリセロールを形成し、続いて得られた脂肪酸をグリセロールホルマールとともに、酸または塩基触媒の存在下においてエステル化することを含む、方法。 - 前記バイオ燃料の、化合物(I)および(II)の含有量が95%を超える、請求項1に記載の方法。
- 前記動物または植物を起源とする油脂が、菜種油、ヒマワリ油、パーム油、やし油、大豆油、オリーブ油、およびそれらの混合物からなる群から選択される、請求項1または2に記載の方法。
- 前記油が菜種油である、請求項3に記載の方法。
- 前記エステル交換が、塩基の存在下において行われる、請求項1〜4のいずれか一項に記載の方法。
- 請求項1〜5のいずれか一項に記載のバイオ燃料を、グリセロールホルマール、バイオディーゼル、石油系ディーゼル、およびそれらの混合物からなる群から選択される化合物と混合することをさらに含んでなる、請求項1〜5のいずれか一項に記載の方法。
- 前記バイオディーゼルが、菜種油、ヒマワリ油、パーム油、やし油、大豆油、オリーブ油、およびそれらの混合物のエステル交換から得られるメチルまたはエチルエステルからなる群から選択される、請求項6に記載の方法。
- 請求項1〜7のいずれか一項に記載の方法により得られる製品。
- 請求項1〜5のいずれか一項に記載の方法により得られるバイオ燃料約70〜85%と、グリセロールホルマール約15〜30%とを含んでなる、請求項8に記載の製品。
- グリセロールホルマール12%以上と、請求項1〜5のいずれか一項に記載の方法により得られるバイオ燃料39%以上とを含んでなり、100%までの残部が、菜種油から得られるバイオディーゼルである、請求項8に記載の製品。
- グリセロールホルマール12%以上と、請求項1〜5のいずれか一項に記載の方法により得られるバイオ燃料40%以上とを含んでなり、100%までの残部が、ヒマワリ油から得られるバイオディーゼルである、請求項8に記載の製品。
- グリセロールホルマール19%以上と、請求項1〜5のいずれか一項に記載の方法により得られるバイオ燃料7%以上とを含んでなり、100%までの残部が、パーム油から得られるバイオディーゼルである、請求項8に記載の製品。
- 石油系ディーゼル約50〜95%を含んでなる、請求項8〜12のいずれか一項に記載の製品。
- 酸化防止剤、オクタン価を増加させる試剤、殺菌剤、キレート化剤、洗剤、分散剤、溶剤、腐食抑制剤、酸化物抑制剤、およびセタン価向上剤からなる群から選択された1種以上の追加成分をさらに含んでなる、請求項8〜13のいずれか一項に記載の製品。
- 請求項8〜14のいずれか一項に記載の製品の、バイオ燃料としての使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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ES200601918 | 2006-07-12 | ||
ESP200601918 | 2006-07-12 | ||
PCT/EP2007/057123 WO2008006860A2 (en) | 2006-07-12 | 2007-07-11 | Preparation of fatty acid esters of glycerol formal and its use as biofuel |
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Publication Number | Publication Date |
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JP2010506960A true JP2010506960A (ja) | 2010-03-04 |
JP2010506960A5 JP2010506960A5 (ja) | 2010-04-15 |
JP5342441B2 JP5342441B2 (ja) | 2013-11-13 |
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JP2009518887A Expired - Fee Related JP5342441B2 (ja) | 2006-07-12 | 2007-07-11 | グリセロールホルマールの脂肪酸エステルの製造およびそのバイオ燃料としての使用 |
Country Status (23)
Country | Link |
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US (1) | US8142525B2 (ja) |
EP (1) | EP2049623B1 (ja) |
JP (1) | JP5342441B2 (ja) |
KR (1) | KR101344770B1 (ja) |
CN (1) | CN101541929B (ja) |
AT (1) | ATE510902T1 (ja) |
AU (1) | AU2007274260B2 (ja) |
BR (1) | BRPI0713161A2 (ja) |
CA (1) | CA2657431C (ja) |
CO (1) | CO6180468A2 (ja) |
CR (1) | CR10586A (ja) |
CY (1) | CY1111764T1 (ja) |
DK (1) | DK2049623T3 (ja) |
ES (1) | ES2365226T3 (ja) |
HK (1) | HK1129416A1 (ja) |
IL (1) | IL196464A (ja) |
MX (1) | MX2009000431A (ja) |
MY (1) | MY145007A (ja) |
NZ (1) | NZ574432A (ja) |
PL (1) | PL2049623T3 (ja) |
PT (1) | PT2049623E (ja) |
SI (1) | SI2049623T1 (ja) |
WO (1) | WO2008006860A2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016501929A (ja) * | 2012-11-09 | 2016-01-21 | インスティトゥト、ウニベルシタット、デ、シエンシア、イ、テクノロヒア、ソシエダ、アノニマInstitut Univ. De Ciencia I Tecnologia,S.A. | バイオ燃料を製造する方法 |
JP2016503830A (ja) * | 2013-01-17 | 2016-02-08 | インスティトゥト、ウニベルシタット、デ、シエンシア、イ、テクノロヒア、ソシエダ、アノニマInstitut Univ. De Ciencia I Tecnologia,S.A. | グリセロール系バイオ燃料の配合物、調製および使用 |
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WO2009158379A2 (en) * | 2008-06-25 | 2009-12-30 | Benefuel Inc. | Process of manufacturing of fatty acid alkyl esters |
US8088948B2 (en) * | 2009-12-11 | 2012-01-03 | Envirosource, Inc. | Systems and methods for processing glycerol |
US8247600B2 (en) * | 2010-04-02 | 2012-08-21 | Envirosource, Inc. | Systems and methods for processing glycerol |
MY163273A (en) | 2011-03-09 | 2017-08-30 | Benefuel Inc | Systems and methods for making bioproducts |
CN102977937A (zh) * | 2012-11-23 | 2013-03-20 | 占小玲 | 一种车用混合燃油 |
WO2014150267A1 (en) | 2013-03-15 | 2014-09-25 | Momentive Specialty Chemicals Inc. | Amino-formaldehyde resins and applications thereof |
US9574152B2 (en) | 2015-02-19 | 2017-02-21 | Hexion Inc. | Diesel fuel additive |
GB201603517D0 (en) | 2016-02-29 | 2016-04-13 | Ocado Innovation Ltd | Improved goods delivery system |
JP7450328B2 (ja) | 2018-08-10 | 2024-03-15 | 栗田工業株式会社 | 凝集沈殿装置、その制御方法及び沈殿槽 |
WO2024089298A1 (es) | 2022-10-24 | 2024-05-02 | Selabtec Sciences, Slu | Método para preparar una composición de biocombustible |
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JP2000080092A (ja) * | 1986-12-29 | 2000-03-21 | Lubrizol Corp:The | ジオキソランおよびチオ類似物、それらの誘導体、およびそれらを含有する潤滑剤および燃料 |
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US20040025417A1 (en) * | 2001-12-19 | 2004-02-12 | Institut Francais Du Petrole | Diesel fuel compositions that contain glycerol acetal carbonates |
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US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
DE19648960A1 (de) | 1996-11-26 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von cyclischen Acetalen oder Ketalen |
ES2201894B2 (es) | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
US8419810B2 (en) | 2004-02-24 | 2013-04-16 | IFP Energies Nouvelles | Method for producing biofuels, transforming triglycerides into at least two biofuel families: fatty acid monoesters and ethers and/or soluble glycerol acetals |
WO2006084048A1 (en) | 2005-02-02 | 2006-08-10 | Jalin Technologies, Llc | Bio-diesel fuel and manufacture of same |
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- 2007-07-11 AT AT07787394T patent/ATE510902T1/de active
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JP2016501929A (ja) * | 2012-11-09 | 2016-01-21 | インスティトゥト、ウニベルシタット、デ、シエンシア、イ、テクノロヒア、ソシエダ、アノニマInstitut Univ. De Ciencia I Tecnologia,S.A. | バイオ燃料を製造する方法 |
JP2016503830A (ja) * | 2013-01-17 | 2016-02-08 | インスティトゥト、ウニベルシタット、デ、シエンシア、イ、テクノロヒア、ソシエダ、アノニマInstitut Univ. De Ciencia I Tecnologia,S.A. | グリセロール系バイオ燃料の配合物、調製および使用 |
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WO2008006860A3 (en) | 2008-05-08 |
CY1111764T1 (el) | 2015-10-07 |
US8142525B2 (en) | 2012-03-27 |
PT2049623E (pt) | 2011-08-11 |
IL196464A (en) | 2015-04-30 |
AU2007274260A1 (en) | 2008-01-17 |
MY145007A (en) | 2011-12-15 |
ATE510902T1 (de) | 2011-06-15 |
WO2008006860A2 (en) | 2008-01-17 |
KR101344770B1 (ko) | 2013-12-24 |
CN101541929A (zh) | 2009-09-23 |
PL2049623T3 (pl) | 2011-11-30 |
NZ574432A (en) | 2010-09-30 |
CA2657431A1 (en) | 2008-01-17 |
IL196464A0 (en) | 2009-09-22 |
US20100005708A1 (en) | 2010-01-14 |
CO6180468A2 (es) | 2010-07-19 |
MX2009000431A (es) | 2009-06-02 |
BRPI0713161A2 (pt) | 2012-04-03 |
CN101541929B (zh) | 2014-04-02 |
ES2365226T3 (es) | 2011-09-26 |
EP2049623A2 (en) | 2009-04-22 |
EP2049623B1 (en) | 2011-05-25 |
DK2049623T3 (da) | 2011-09-05 |
CA2657431C (en) | 2014-02-11 |
SI2049623T1 (sl) | 2011-09-30 |
HK1129416A1 (en) | 2009-11-27 |
AU2007274260B2 (en) | 2011-06-30 |
JP5342441B2 (ja) | 2013-11-13 |
CR10586A (es) | 2009-04-29 |
KR20090045243A (ko) | 2009-05-07 |
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