CN101792388A - 制备脂肪酸烷基酯的方法 - Google Patents
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Abstract
本发明涉及通过甘油三酯和脂肪酸混合物的酯交换、尤其是催化酯交换生产脂肪酸烷基酯的方法,其中从进行酯交换的反应混合物中,形成含有脂肪酸烷基酯的酯相和含有脂肪酸的甘油相,将两相分离,从甘油相中分离所述脂肪酸,由此产生含有脂肪酸的脂肪酸相,用醇酯化脂肪酸。本方法的特征为,将所述脂肪酸相与另一种甘油三酯和脂肪酸的混合物混合,并且用醇酯化如此获得的混合物中所含有的脂肪酸,由此获得含有甘油三酯和脂肪酸烷基酯的酯化混合物。然后使所述酯化混合物与醇进行酯交换,以产生其它脂肪酸烷基酯。
Description
本申请为分案申请,原申请的申请日为2001年10月5日,申请号为01803011.4(PCT/AT01/00320),发明名称为“制备脂肪酸烷基酯的方法”。
本发明涉及一种通过甘油三酯和脂肪酸的混合物的酯交换、特别是催化酯交换制备脂肪酸烷基酯的方法,其中从进行酯交换的反应混合物中,形成含有脂肪酸烷基酯的酯相和含有脂肪酸的甘油相,将两相分离,从甘油相中分离出所述脂肪酸,由此形成含有脂肪酸的脂肪酸相,用醇酯化脂肪酸。
对于本说明书和权利要求书来说,所谓甘油三酯应理解为由饱和和/或不饱和高级脂肪酸和甘油生成的酯。这类酯例如是来源于植物或动物来源的脂肪,还有废弃的食用油和废料脂肪。然而,许多来源于天然来源的脂肪也不同程度地含有游离脂肪酸。因此,那些脂肪是甘油三酯和游离脂肪酸的混合物,这种混合物的主要成分一般是甘油三酯。
所谓酯交换应理解为甘油三酯的醇解,即与醇反应,特别是与甲醇和乙醇反应,其中通过中间体产物甘油二酯和甘油一酯,生成所述脂肪酸的一酯以及甘油。
脂肪酸酯、特别是甲酯,是油化学(oleochemie)中重要的中间体产物。仅在欧洲,每年生产200,000吨植物油的甲酯,主要作为表面活性剂的原料。除此之外,作为柴油的代用燃料,脂肪酸甲酯的重要性也日益增加。
关于酯交换的催化剂,可以使用碱性催化剂(碱性氢氧化物、碱性醇化物、碱性氧化物、碱性碳酸盐、阴离子交换剂)、酸性催化剂(无机酸、对甲苯磺酸、三氟化硼、阳离子交换剂)和酶(脂酶)。今天,最好使用可溶于反应混合物的催化剂。它们形成均相混合物,并且确保证反应速率快和反应条件温和。最常用的均相催化剂是氢氧化钠、氢氧化钾以及甲醇钠,将溶于醇中的所述均相催化剂与植物油混合。可从AT-B386222了解到这种方法。酸性催化剂需要较高的反应温度和压力以及更为复杂的反应程序。酸性酯交换可从FR-A-8502340中了解到。
用碱性催化剂进行的酯交换可不使用溶剂来进行。反应始于甘油三酯和醇的两相体系;但在反应进行和酯的生成期间形成均相,由于甘油的生成和分离而又变为两相。
在用以制备脂肪酸与一元醇的酯的甘油三酯的醇解过程中,产生一个作为副产物的富含甘油的相。该相还含有脂肪酸、脂肪酸盐和脂肪酸酯。为了从甘油相中分离这些脂肪酸化合物,一般用酸进行处理。通过这种处理,脂肪酸从脂肪酸盐中游离出来。脂肪酸和脂肪酸酯本身与甘油不可混溶,因此作为一个单独的相从甘油相中分离出来。该相被称为脂肪酸相。
最初提到的那种方法可以从EP-A-0708813中得到。这种先前已知的方法通过用醇酯化该相中含有的脂肪酸、并且将所获得的脂肪酸烷基酯添加到正在进行酯交换的另一反应混合物中,来利用所述脂肪酸相。
正如已经提到的,来源于天然来源的脂肪也不同程度地含有游离脂肪酸。游离脂肪酸的含量越高,可用作酯交换原料的甘油三酯则越少。另一方面,按照在上述EP-A-0807813中所述,如果在一个单独的步骤中将所述游离脂肪酸酯化,则可以提高脂肪酸烷基酯的收率。
从Oleagineux,第40卷,第3期,第148-151页(1985)中得知,借助含有乙醇的溶剂混合油,而用硫酸作为催化剂,将脂肪酸相中含有的游离脂肪酸酯化为甲酯;用CaO中和硫酸;滤出所生成的硫酸钙;将所得酯与酯交换催化剂混合;并且让富含油的有机混合油与该混合物进行酯交换。溶剂混合油分别在含油或脂肪的原料的萃取期间获得,因此溶剂混合油是萃取剂和待酯交换的甘油三酯的混合物。该方法的费用非常大,并且不太适合于含有游离脂肪酸的含油原料的酯交换。
这正是本发明着手的地方,本发明的目的是提供最初所述的该种方法,按照该方法,可以在不经处理的状态下、即无需纯化和除去硫酸,加工所述脂肪酸,并且按照该方法,也可以对具有较高含量游离脂肪酸的原料进行酯交换。
按照本发明的方法的特征为:将脂肪酸相与另一种甘油三酯和脂肪酸的混合物混合,并且用醇酯化所得混合物中所含有的脂肪酸,由此获得含有甘油三酯和脂肪酸烷基酯的酯化混合物,使酯化混合物与醇进行酯交换,以便形成其它脂肪酸烷基酯。
因此,按照本发明的方法,在实际的酯交换之前,用醇酯化分别在待酯交换的脂肪或油(即甘油三酯和脂肪酸的混合物)中含有的脂肪酸,由此在存在得自前一次酯交换的脂肪酸相的情况下进行所述酯化,使得在待酯交换的脂肪中含有的脂肪酸以及在所混合的脂肪酸相中所含有的脂肪酸都被酯化。
得自前一次酯交换的脂肪酸相无需纯化,可以照原样,即加上过量的乙醇,将其加入到所述脂肪中。
如果脂肪含有非常高含量的游离脂肪酸,那么在所述酯交换之前,可以用醇对第一次酯化后所获得的酯化混合物至少再进行一次酯化。这样,可以逐渐降低游离脂肪酸的含量,使得有可能达到100%的脂肪酸烷基酯收率。
因此,本发明方法的一个优选实施方案的特征为,与脂肪酸相混合的甘油三酯和脂肪酸的混合物,显示出脂肪酸含量至少为5%(重量),特别是至少为10%(重量)。
所述酯化最好在酸性催化下进行,所述酯交换最好在碱性催化下进行。
在按照本发明的方法中,具体用甲醇或乙醇作为供酯交换和酯化用的醇。
通过以下实施例,更详细地描述本发明的一个示范性实施方案。
实施例
1.酯化
首先,将1,000g游离脂肪酸含量为7.15%的废弃食用油与100g甲醇和7.0g硫酸(98%)混合以进行酯化,将其回流2小时。将批料转移到分液漏斗中,分离为水相(51.6g)和油相(1,045.0g)。
2.酯交换
按照AT-B386.222中所述的方法,将油相经过两步碱性酯交换。这样,将油相与总共192.2g甲醇和12.19g KOH混合,在每个阶段后分离所形成的甘油相。在旋转蒸发器中从所形成的酯相(917.8g)中除去甲醇(40.8g),因此获得877.0g脂肪酸甲酯。
3.脂肪酸相的形成
通过加入12.0g硫酸,使两个从酯交换回收的甘油相(328.1g)的pH值约为3。通过这种酸化,从甘油相中存在的钾皂形成游离脂肪酸和作为固相得到的钾盐。将所形成的混合物过滤,将滤液转移到分液漏斗中。在相分离后,所述的量如下:脂肪酸相103.5g,甘油相200.2g,过滤残余物32.8g。
4.酯化
将由此回收的脂肪酸相(103.5g)与896.5g游离脂肪酸含量为7.15%的废弃食用油混合,为了进行酯化,将其与100g甲醇和7.0g硫酸(98%)一起回流2小时。将批料转移到分液漏斗中,分离为水相(59.2g)和油相(1,047.8g)。所述油中的游离脂肪酸含量等于0.98%。
5.酯交换
按照AT-B386.222中所述的方法,使油相经过两步碱性酯交换。这样,将油相与总共190.8g甲醇和12.11g KOH混合,在每个阶段后分离所形成的甘油相。在旋转蒸发器中从所形成的酯相(1,016.4g)中除去甲醇(56.3g),由此留下作为纯酯相的907.1g。
6.脂肪酸相的形成
将得自酯交换的甘油相(282.1g)结合在一起,通过加入10.1g硫酸,使pH值约为3。将所形成的混合物过滤,将滤液转移到分液漏斗中。在相分离后,所述的量如下:脂肪酸相97.2g,甘油相161.2g,过滤残余物33.8g。
可以将所获得的脂肪酸相再次与废弃食用油混合,可以将其用以进一步生产甲酯。
Claims (5)
1.一种通过在碱性催化下甘油三酯和脂肪酸的混合物的酯交换来制备脂肪酸烷基酯的方法,其中
从进行酯交换的反应混合物中,形成含有脂肪酸烷基酯的酯相和含有脂肪酸的甘油相,将两相分离,通过用酸处理从所述甘油相中分离出所述脂肪酸,由此形成脂肪酸相,用醇酯化所述脂肪酸,
其特征为,
将所述脂肪酸相与另一甘油三酯和脂肪酸的混合物混合,并且用醇酯化所得混合物中所含有的脂肪酸,由此获得水相和油相,将两相分离,使含有甘油三酯和脂肪酸烷基酯的油相与醇进行酯交换,以便形成其它脂肪酸烷基酯,其中与所述脂肪酸相混合的甘油三酯和脂肪酸的混合物显示出脂肪酸含量至少为5%重量。
2.一种权利要求1的方法,其特征为,在所述酯交换之前,用醇再一次酯化所述油相。
3.一种权利要求1的方法,其特征为,与所述脂肪酸相混合的甘油三酯和脂肪酸的混合物显示出脂肪酸含量至少为10%重量。
4.一种权利要求1-3中任一项的方法,其特征为,在酸性催化下进行所述酯化。
5.一种权利要求1-4中任一项的方法,其特征为,用甲醇或乙醇作为供所述酯交换和所述酯化用的醇。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104271714A (zh) * | 2012-03-09 | 2015-01-07 | 安东尼奥·坎蒂萨尼 | 用于小规模原位生产生物柴油的方法和装置 |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8088183B2 (en) | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US7806945B2 (en) | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US7871448B2 (en) | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US20050027137A1 (en) * | 2003-07-29 | 2005-02-03 | Hooker Jeffrey D. | Apparatus and method for the production of fatty acid alkyl ester |
US6822105B1 (en) * | 2003-08-12 | 2004-11-23 | Stepan Company | Method of making alkyl esters using glycerin |
US6890451B2 (en) * | 2003-09-23 | 2005-05-10 | Richard Sapienza | Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products |
US8313667B2 (en) | 2003-09-23 | 2012-11-20 | Mli Associates, L.L.C. | Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products |
US7473539B2 (en) * | 2004-09-20 | 2009-01-06 | Sunho Biodiesel Corporation | Methods for producing alkyl esters |
US9012506B2 (en) | 2004-09-28 | 2015-04-21 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
WO2006036967A1 (en) | 2004-09-28 | 2006-04-06 | Atrium Medical Corporation | Solubilizing a drug for use in a coating |
WO2007011385A2 (en) | 2004-09-28 | 2007-01-25 | Atrium Medical Corporation | Heat cured gel and method of making |
US9801982B2 (en) | 2004-09-28 | 2017-10-31 | Atrium Medical Corporation | Implantable barrier device |
US9000040B2 (en) | 2004-09-28 | 2015-04-07 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
US7842653B2 (en) * | 2005-06-16 | 2010-11-30 | Council Of Scientific & Industrial Research | Process for the preparation of lubricants |
JPWO2007000913A1 (ja) * | 2005-06-27 | 2009-01-22 | 国立大学法人東京工業大学 | 高級脂肪酸エステルの製造方法 |
JP2007022988A (ja) * | 2005-07-20 | 2007-02-01 | Rebo International:Kk | 脂肪酸アルキルエステルの製造方法 |
ES2245270B1 (es) * | 2005-07-22 | 2006-09-16 | Fundacion Cidaut | Procedimiento para la obtencion de comustible para motores de ciclo diesel a partir de aceites vegetales usados. |
JP4219349B2 (ja) * | 2005-09-16 | 2009-02-04 | 富士フイルム株式会社 | 脂肪酸アルキルエステルの製造方法及び燃料 |
FR2890962B1 (fr) * | 2005-09-21 | 2007-11-23 | Inst Francais Du Petrole | Procede ameliore de fabrication d'esters ethyliques a partir de corps gras d'origine naturelle |
FR2890961B1 (fr) * | 2005-09-21 | 2007-11-23 | Inst Francais Du Petrole | Procede perfectionne de fabrication d'esters ethyliques a partir de corps gras d'origine naturelle |
US9278161B2 (en) | 2005-09-28 | 2016-03-08 | Atrium Medical Corporation | Tissue-separating fatty acid adhesion barrier |
US9427423B2 (en) | 2009-03-10 | 2016-08-30 | Atrium Medical Corporation | Fatty-acid based particles |
US7754643B2 (en) * | 2005-10-07 | 2010-07-13 | Council Of Scientific & Industrial Research | Transesterification catalyst and a process for the preparation thereof |
ES2332284T3 (es) * | 2005-10-10 | 2010-02-01 | Council Of Scientific And Industrial Research | Proceso para la preparacion de carbonato de dialquilo. |
US7482480B2 (en) * | 2005-10-10 | 2009-01-27 | Council Of Scientific & Industrial Research | Process for the preparation of hydrocarbon fuel |
US20070155859A1 (en) * | 2006-01-04 | 2007-07-05 | Zhengzhe Song | Reactive polyurethane hot melt adhesive |
US7622600B1 (en) * | 2006-01-06 | 2009-11-24 | Redland Industries, Inc. | System and method for the continuous production of bio-diesel |
US7828978B2 (en) * | 2006-01-11 | 2010-11-09 | Doug Geier | Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel |
US20070261294A1 (en) * | 2006-05-10 | 2007-11-15 | Aiken John E | Process for production of biodiesel from high acid feed |
US7901469B2 (en) * | 2006-07-26 | 2011-03-08 | Alternative Fuels Group Inc. | Alternative organic fuel formulations including vegetable oil |
CA2663692A1 (en) * | 2006-09-19 | 2008-03-27 | Best Energies, Inc. | Biodiesel processes in the presence of free fatty acids and biodiesel producer compositions |
US9492596B2 (en) | 2006-11-06 | 2016-11-15 | Atrium Medical Corporation | Barrier layer with underlying medical device and one or more reinforcing support structures |
EP2083875B1 (en) | 2006-11-06 | 2013-03-27 | Atrium Medical Corporation | Coated surgical mesh |
HU0700128D0 (en) * | 2007-02-06 | 2007-03-28 | Thesz Janos | Method for fabrication of modifided structured triglyceride as biodisel fuel |
US8481771B2 (en) * | 2007-03-22 | 2013-07-09 | Cps Biofuels, Inc. | Biodiesel process |
WO2009039144A1 (en) * | 2007-09-19 | 2009-03-26 | Best Energies, Inc. | Processes for the esterification of free fatty acids and the production of biodiesel |
US8124801B2 (en) * | 2008-06-24 | 2012-02-28 | Benefuel Inc. | Process of manufacturing of fatty acid alkyl esters |
EP2303827B1 (en) | 2008-06-25 | 2019-10-16 | Benefuel Inc. | Process of manufacturing of fatty acid alkyl esters |
US20110038910A1 (en) | 2009-08-11 | 2011-02-17 | Atrium Medical Corporation | Anti-infective antimicrobial-containing biomaterials |
US8703849B2 (en) | 2010-01-22 | 2014-04-22 | Archer Daniels Midland Company | Processes for making high purity renewable source-based plasticizers and products made therefrom |
EP2593141B1 (en) | 2010-07-16 | 2018-07-04 | Atrium Medical Corporation | Composition and methods for altering the rate of hydrolysis of cured oil-based materials |
AT510636B1 (de) | 2010-10-28 | 2016-11-15 | Wimmer Theodor | Verfahren zur herstellung von fettsäureestern niederer alkohole |
WO2012112660A2 (en) * | 2011-02-15 | 2012-08-23 | Board Of Regents, The University Of Texas System | A metal-organic framework with optimized open metal sites and pore spaces for high methane storage at room termerature |
MY163273A (en) | 2011-03-09 | 2017-08-30 | Benefuel Inc | Systems and methods for making bioproducts |
US9867880B2 (en) | 2012-06-13 | 2018-01-16 | Atrium Medical Corporation | Cured oil-hydrogel biomaterial compositions for controlled drug delivery |
WO2014201001A1 (en) | 2013-06-11 | 2014-12-18 | Renewable Energy Group, Inc. | Production of biodiesel and products obtained therefrom |
UY35649A (es) * | 2013-07-09 | 2015-02-27 | Reg Seneca Llc | ?producción de productos a partir de materias primas que contienen ácidos grasos libres?. |
US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
CZ308339B6 (cs) * | 2016-02-17 | 2020-06-03 | Stanislav Nikl | Způsob přípravy esterů mastných kyselin esterifikací olejů a tuků s vyšším obsahem volných mastných kyselin methanolem nebo ethanolem |
CN111574363B (zh) * | 2020-05-26 | 2023-09-26 | 杭州潜阳科技有限公司 | 一种邻苯二甲酸二甲酯的生产工艺 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB612667A (en) * | 1945-05-29 | 1948-11-16 | Unilever Ltd | Improvements in or relating to methods of alcoholysis of low grade fatty materials |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2521742A (en) * | 1946-07-16 | 1950-09-12 | Lever Brothers Ltd | Method of treating low-grade fatty materials |
BR8300429A (pt) | 1983-01-28 | 1984-09-04 | Brasil Pesquisa Agropec | Processo da transesterificacao de oleos vegetais |
DE3319590A1 (de) | 1983-05-30 | 1984-12-06 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeureestern kurzkettiger aliphatischer alkohole aus freie fettsaeuren enthaltenden fetten und/oder oelen |
DE3444893A1 (de) | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeuremethylestern |
AT392977B (de) | 1989-10-13 | 1991-07-25 | Wimmer Theodor | Verfahren zur aufbereitung der bei der umesterung von fetten und oelen mit niederen alkoholen anfallenden glycerinphase |
FR2696185B1 (fr) | 1992-09-25 | 1994-12-02 | Inst Francais Du Petrole | Procédé amélioré de fabrication d'esters à partir de corps gras d'origine naturelle. |
AT399336B (de) | 1993-07-14 | 1995-04-25 | Martin Mag Dr Mittelbach | Verfahren zur herstellung von fettsäurealkylestern |
-
2000
- 2000-10-05 AT AT0169900A patent/ATA16992000A/de unknown
-
2001
- 2001-10-05 SK SK774-2002A patent/SK287690B6/sk not_active IP Right Cessation
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- 2001-10-05 DK DK01971467.4T patent/DK1322588T3/en active
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- 2001-10-05 EP EP01971467.4A patent/EP1322588B1/de not_active Revoked
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB612667A (en) * | 1945-05-29 | 1948-11-16 | Unilever Ltd | Improvements in or relating to methods of alcoholysis of low grade fatty materials |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104271714A (zh) * | 2012-03-09 | 2015-01-07 | 安东尼奥·坎蒂萨尼 | 用于小规模原位生产生物柴油的方法和装置 |
CN104271714B (zh) * | 2012-03-09 | 2016-05-04 | 亚历山大·德·利马·坎蒂萨尼 | 用于小规模原位生产生物柴油的方法和装置 |
Also Published As
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HUP0204190A2 (hu) | 2003-04-28 |
US20030004363A1 (en) | 2003-01-02 |
EP1322588B1 (de) | 2016-06-29 |
EP1322588A1 (de) | 2003-07-02 |
WO2002028811A1 (de) | 2002-04-11 |
JP2004510044A (ja) | 2004-04-02 |
CA2392723A1 (en) | 2002-04-11 |
CZ298652B6 (cs) | 2007-12-05 |
CZ20021854A3 (cs) | 2002-11-13 |
SK287690B6 (sk) | 2011-06-06 |
HUP0204190A3 (en) | 2011-01-28 |
EE200200289A (et) | 2003-12-15 |
BR0107288A (pt) | 2002-08-27 |
RU2287519C2 (ru) | 2006-11-20 |
ES2593283T3 (es) | 2016-12-07 |
LT1322588T (lt) | 2016-10-10 |
DK1322588T3 (en) | 2016-09-19 |
NZ519001A (en) | 2004-10-29 |
AU9146601A (en) | 2002-04-15 |
US6696583B2 (en) | 2004-02-24 |
ATA16992000A (de) | 2001-12-15 |
SK7742002A3 (en) | 2003-09-11 |
PL206658B1 (pl) | 2010-09-30 |
CN1392873A (zh) | 2003-01-22 |
PL355294A1 (en) | 2004-04-05 |
CA2392723C (en) | 2011-01-25 |
ZA200203786B (en) | 2003-05-13 |
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