JP2014534192A - エステルの製造方法 - Google Patents
エステルの製造方法 Download PDFInfo
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- JP2014534192A JP2014534192A JP2014535219A JP2014535219A JP2014534192A JP 2014534192 A JP2014534192 A JP 2014534192A JP 2014535219 A JP2014535219 A JP 2014535219A JP 2014535219 A JP2014535219 A JP 2014535219A JP 2014534192 A JP2014534192 A JP 2014534192A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
-
- 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
-
- 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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- 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
-
- 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
- C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
このエステル化反応においてフリー脂肪酸を転化するためには、安定性の高い触媒を用いることが重要である。しかし、通常用いられる反応条件下では、多くの触媒は、フリー脂肪酸及び形成される水の存在下で溶解し、したがって触媒は急速に失活する。さらに、触媒の(物理的)分解が起こり、これは望ましくない微粒子形成とその結果望まない圧力低下、特に固定床における圧力低下をもたらしうる。さらに、触媒の一部が生成物中に残り、規格に適合させるためにそれを除去する必要がある。
米国特許第5508457号明細書にしたがって作ったチタニウムシリケートの錠剤10mLを固定床反応器に装填した。その反応器に、MeOH(1.73mL/h)と、5質量%のドデカン酸を含むなたね油(3.47mL/h)とを供給した。180℃で284時間の操作後、反応を止めて、生成物流と触媒を分析した。生成物流は、微量のチタン及びケイ素(数〜数十ppm(w/w))しか含んでいかなった。
さまざまな量のNaを含むチタニウムシリケート錠剤10mLを、例1にしたがって調製した錠剤をさまざまな量のHCl水で処理することによって調製した。錠剤の最終的Na含有量は、水相のpHをコントロールすることによって調節できる。HCl処理の2時間後、錠剤を脱イオン水で完全に洗い、オーブン中110℃で夜通し乾燥させた。この操作によって、明確なNa含有量、すなわち、6.0、3.9、3.2、2.4、及び0.8質量%のNa含有量をそれぞれが有するチタニウムシリケート錠剤の製造が可能になった。
Claims (13)
- トリグリセリド供給原料及びアルコールを準備するステップ、及び前記供給原料を不均一系触媒と接触させるステップ、それにより前記トリグリセリドと前記アルコールとのエステル交換をするステップを含む、エステル、特にバイオディーゼルの製造方法であって、前記不均一系触媒が第4族シリケートを含みかつNaを3質量%未満しか含まず、かつ、前記供給原料がさらに少なくとも一種の酸化合物を含むことを特徴とする製造方法。
- 前記バイオディーゼルがFAME(脂肪酸メチルエステル)を含む生成物である、請求項1に記載の製造方法。
- 前記アルコールが短鎖アルコール、特にメタノールである、請求項1又は2に記載の製造方法。
- 前記酸化合物が、脂肪酸、水、又はその両方である、請求項1〜3のいずれか一項に記載の製造方法。
- 前記第4族シリケート含有触媒がチタノシリケートを含む、請求項1〜4のいずれか一項に記載の製造方法。
- 前記供給原料中のフリー脂肪酸の含有量が、前記供給原料の全質量を基準にして0.1〜99質量%、好ましくは1〜30質量%である、請求項1〜5のいずれか一項に記載の製造方法。
- 前記供給原料と前記触媒との接触を固定床反応器又はスラリー反応器中で行う、請求項1〜6のいずれか一項に記載の製造方法。
- 前記供給原料と前記触媒との接触を40〜300℃、好ましくは120〜230℃の温度で行う、請求項1〜7のいずれか一項に記載の製造方法。
- 前記トリグリセリドが、動物、植物、又は微生物由来である、特に、大豆油、菜種油、パーム油、ひまわり油、サフラワー油、ヤトロファ(ナンヨウアブラギリ)油、からし油、麻実油、ヒマシ油、廃植物油、藻類のオイル、動物脂肪、トラップグリース、及びそれらの組み合わせ物から選択されるオイル及び/又は脂肪供給原料に含まれる、請求項1〜8のいずれか一項に記載の製造方法。
- 前記触媒が促進剤をさらに含む、請求項1〜9のいずれか一項に記載の製造方法。
- 前記促進剤が、カチオン、アニオン、及び/又は有機化合物、あるいはそれらの組み合わせから選択される、請求項10に記載の製造方法。
- 前記カチオン促進剤が、Li、Cs、Mg、Ca、Sr、Ba、La、Nb、Fe、Ni、V、W、Mo、Al、Ce、Sn、Zn、Cu、Mnのイオン及びそれらの組み合わせから選択され;
前記アニオン促進剤が、SO4 2−、BF4 −、CO3 2−、NO3 −、PO4 3−、F−、Cl−、Br−、I−、O2−、ヘテロポリ酸のアニオン、Keggin型アニオン、又はそれらの組み合わせから選択され;及び/又は、
前記有機化合物促進剤が、
− アニオン性有機化合物、例えば、OR、RSO3(式中、Rは有機基である);
− カチオン性有機化合物、例えば、アンモニウム、アルキルアンモニウム、アリールアンモニウム化合物;
− 中性有機化合物、例えば、ホスフィン類、アミン類、アルコール類、又はチオール類;及び
− それらの組み合わせ、
から選択される、請求項11に記載の製造方法。 - 前記触媒が3質量%未満のKしか含まない、請求項1〜11のいずれか一項に記載の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11185085 | 2011-10-13 | ||
EP11185085.5 | 2011-10-13 | ||
PCT/IB2012/055556 WO2013054306A1 (en) | 2011-10-13 | 2012-10-12 | Process for making esters |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014534192A true JP2014534192A (ja) | 2014-12-18 |
JP6207512B2 JP6207512B2 (ja) | 2017-10-04 |
Family
ID=47221502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014535219A Expired - Fee Related JP6207512B2 (ja) | 2011-10-13 | 2012-10-12 | エステルの製造方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US8981136B2 (ja) |
EP (1) | EP2766335B1 (ja) |
JP (1) | JP6207512B2 (ja) |
KR (1) | KR20140079792A (ja) |
CN (1) | CN103987689B (ja) |
AR (1) | AR088348A1 (ja) |
BR (1) | BR112014008909A2 (ja) |
CA (1) | CA2852036A1 (ja) |
IN (1) | IN2014CN03325A (ja) |
MY (1) | MY169859A (ja) |
SG (1) | SG11201401492RA (ja) |
WO (1) | WO2013054306A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106318648A (zh) * | 2015-06-30 | 2017-01-11 | 中国科学院大连化学物理研究所 | 基于微通道反应器的转酯化方法 |
CN106833767A (zh) * | 2017-04-19 | 2017-06-13 | 湖北文理学院 | 一种生物柴油 |
CN109529889A (zh) * | 2018-12-03 | 2019-03-29 | 广西锟德能源科技有限公司 | 一种酯化催化剂及其制备方法和在生物柴油制造中的应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06504714A (ja) * | 1990-12-04 | 1994-06-02 | エンゲルハード・コーポレーシヨン | 非晶質の錫およびチタンケイ酸塩を用いた競合イオン含有水系からの重金属、特に鉛除去 |
JPH07173103A (ja) * | 1993-05-04 | 1995-07-11 | Engelhard De Meern Bv | エステル化方法 |
JP2001316517A (ja) * | 2000-05-02 | 2001-11-16 | Ishikawajima Harima Heavy Ind Co Ltd | 廃プラスチック処理方法および装置 |
JP2005200398A (ja) * | 2003-08-29 | 2005-07-28 | Nippon Shokubai Co Ltd | 脂肪酸アルキルエステル及び/又はグリセリンの製造方法 |
WO2006033328A1 (ja) * | 2004-09-21 | 2006-03-30 | Tosoh Corporation | アルミノシリケートを含む新規な構造体、その製造方法およびその用途 |
JP2008013758A (ja) * | 2006-06-07 | 2008-01-24 | Shiro Saka | 脂肪酸アルキルエステルの製造方法 |
JP2008074764A (ja) * | 2006-09-21 | 2008-04-03 | Mitsubishi Chemicals Corp | プロピレンの製造方法 |
-
2012
- 2012-10-12 WO PCT/IB2012/055556 patent/WO2013054306A1/en active Application Filing
- 2012-10-12 KR KR1020147011014A patent/KR20140079792A/ko active IP Right Grant
- 2012-10-12 US US14/350,688 patent/US8981136B2/en not_active Expired - Fee Related
- 2012-10-12 BR BR112014008909A patent/BR112014008909A2/pt not_active Application Discontinuation
- 2012-10-12 EP EP12790665.9A patent/EP2766335B1/en not_active Not-in-force
- 2012-10-12 SG SG11201401492RA patent/SG11201401492RA/en unknown
- 2012-10-12 JP JP2014535219A patent/JP6207512B2/ja not_active Expired - Fee Related
- 2012-10-12 MY MYPI2014700906A patent/MY169859A/en unknown
- 2012-10-12 CA CA2852036A patent/CA2852036A1/en not_active Abandoned
- 2012-10-12 CN CN201280060628.XA patent/CN103987689B/zh not_active Expired - Fee Related
- 2012-10-15 AR ARP120103848A patent/AR088348A1/es active IP Right Grant
-
2014
- 2014-05-01 IN IN3325CHN2014 patent/IN2014CN03325A/en unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06504714A (ja) * | 1990-12-04 | 1994-06-02 | エンゲルハード・コーポレーシヨン | 非晶質の錫およびチタンケイ酸塩を用いた競合イオン含有水系からの重金属、特に鉛除去 |
JPH07173103A (ja) * | 1993-05-04 | 1995-07-11 | Engelhard De Meern Bv | エステル化方法 |
JP2001316517A (ja) * | 2000-05-02 | 2001-11-16 | Ishikawajima Harima Heavy Ind Co Ltd | 廃プラスチック処理方法および装置 |
JP2005200398A (ja) * | 2003-08-29 | 2005-07-28 | Nippon Shokubai Co Ltd | 脂肪酸アルキルエステル及び/又はグリセリンの製造方法 |
WO2006033328A1 (ja) * | 2004-09-21 | 2006-03-30 | Tosoh Corporation | アルミノシリケートを含む新規な構造体、その製造方法およびその用途 |
JP2008013758A (ja) * | 2006-06-07 | 2008-01-24 | Shiro Saka | 脂肪酸アルキルエステルの製造方法 |
JP2008074764A (ja) * | 2006-09-21 | 2008-04-03 | Mitsubishi Chemicals Corp | プロピレンの製造方法 |
Non-Patent Citations (1)
Title |
---|
SUPPES,G. J.,ET AL., APPLIED CATALYSIS A: GENERAL, vol. 257, no. 2, JPN6016021199, 2004, pages 213 - 223, ISSN: 0003611453 * |
Also Published As
Publication number | Publication date |
---|---|
EP2766335B1 (en) | 2015-12-30 |
JP6207512B2 (ja) | 2017-10-04 |
CA2852036A1 (en) | 2013-04-18 |
SG11201401492RA (en) | 2014-08-28 |
US8981136B2 (en) | 2015-03-17 |
IN2014CN03325A (ja) | 2015-07-03 |
WO2013054306A1 (en) | 2013-04-18 |
EP2766335A1 (en) | 2014-08-20 |
MY169859A (en) | 2019-05-23 |
US20140364637A1 (en) | 2014-12-11 |
CN103987689B (zh) | 2016-06-29 |
BR112014008909A2 (pt) | 2017-05-09 |
KR20140079792A (ko) | 2014-06-27 |
AR088348A1 (es) | 2014-05-28 |
CN103987689A (zh) | 2014-08-13 |
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