CN1441837A - 酯交换方法 - 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
- C11C3/04—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
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
Abstract
本发明有关于一种通过酯交换反应制备羧酸链烷醇酯的方法,包括如下步骤:(1)将一种羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括产物酯和产物醇的混合物;(2)将来自步骤(1)的反应混合物通过一个离心分离区,将第二醇与第二酯分离。按本发明的方法能使反应时间更短且能改善产物收率。
Description
发明背景
本发明涉及通过酯交换反应制备羧酸链烷醇酯的方法,其中产物醇从反应混合物中快速移出,从而能有效提高反应速度和酯的总收率。
众所周知,酯交换反应的产物组成是由热力学平衡决定的。因此,为使产物酯的量达到最大,应该将产物醇尽快移出,以便移动到有利于产物的平衡位置。但是,在工业规模的操作中,这些产物醇的移出不太容易达到。例如,在甘油三酸酯与甲醇进行酯交换反应形成脂肪酸甲酯的间歇式生产过程中,将甘油三酸酯、甲醇和甲醇钠一起加入,混合物于75-80℃下反应1小时。关掉搅拌器,使混合物静置。甘油层将出现在底部,并从容器中排出。开动搅拌器,再加入一些甲醇钠,混合物于75-80℃下再反应1小时,排出甘油,粗甲酯用水洗涤并干燥。在一个连续生产过程中,将甘油三酸酯、甲醇和催化剂用泵计量混在一起并通过用泵将混合物经过一个静态混合器和管道长度送到一个沉降罐来实现混合。在此罐中,混合物被泵送到罐的一侧,在另一侧移出甲酯,甘油从底部排出。甲酯一离开此沉降罐,就进一步与另外的甲醇和催化剂混合,泵送通过静态混合器,经过管道,进入第二沉降罐。甲酯由此罐泵出,送去进一步精制。
前述实例显示在甘油三酸酯的酯交换反应过程中甘油、产物醇的快速移出通常不太容易。因此,产物甲酯的形成速度也不可能达到像甘油一形成就被移出的情况那样快。甘油的快速移出将使经济上更为有利。
发明概述
最广义地说,本发明有关于一种通过酯交换反应制备羧酸链烷醇酯的方法,包括如下步骤:(1)将一种羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括产物酯和产物醇的混合物;(2)将来自步骤(1)的反应混合物通过一个离心分离区,将第二醇与第二酯分离。按本发明的方法能使反应时间更短且能改善产物收率。
几个附图简介
图1是按本发明方法的流程图。CINC是离心分离器。
图2示出甘油三酸酯转化为甲酯的转化率随时间关系的曲线。
发明详述
按本发明的方法特别适用于酯交换反应。酯交换反应是本领域技术人员所熟知的,可用下面的反应式描述:
羧酸酯 醇 产物酯 产物醇
按本发明的方法可应用于反应中所形成产物醇密度大于酯交换反应所形成产物酯密度的任何酯交换反应。例如,若含月桂酸、肉豆蔻酸和油酸残基的甘油三酸酯与甲醇进行酯交换反应,则反应中所形成的醇,即甘油的密度大于月桂酸甲酯、肉豆蔻酸甲酯和油酸甲酯。在另一个实例中,若乙二醇二乙酸酯与甲醇进行酯交换反应,反应中所形成的醇,即乙二醇的密度大于乙酸甲酯。
按本发明方法的实施步骤是先将一种羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括产物酯和产物醇的混合物。羧酸酯可以是任何一元醇或多元醇如乙二醇或甘油的酯。醇与酯的摩尔比可以是能在期望的时间内有效将基本全部羧酸酯转化为产物酯的任何比例。一般来说,该摩尔比约3∶1,优选6∶1且最优选8∶1。有效量催化剂是必须能在期望的时间内将基本全部羧酸酯转化为产物酯的任何量。一般来说,该有效量将从约0.01%(重)到5%(重)变动,优选0.01-2%(重)且最优选0.03-1.5%(重)。催化剂可以是本领域技术人员所熟知的任何酯交换催化剂。一般来说,催化剂是金属烷醇盐如反应物醇的金属烷醇盐。例如,若反应物醇是甲醇,那么催化剂可以是金属甲醇盐如甲醇钠或甲醇钾。
反应区可以是任何酯交换反应常用类型的容器,例如包括但不限于带有搅拌器或搅动器的反应器、带有循环管路的反应器或是管内或类似容器内的静态混合器。反应混合物在反应区停留一段足以将基本全部羧酸酯转化为产物酯的时间。然后将反应混合物通过一个离心分离区,离心分离区可以是任何类型的可用离心分离机来分离不同密度液体的分离设备。离心分离过程能从酯交换反应中快速移出产物醇,有助于驱使反应完全。优选离心分离区包括一个离心分离器。优选的离心分离器是由Costner Industries Nevada Corp.(CINC)获得的V02型,参见美国专利5762800中的描述,其全部内容并入本文引为参考。
在一个特别优选的实施方案中,按本发明的方法用于通过甘油三酸酯与甲醇的酯交换反应来生产脂肪酸甲酯。甘油三酸酯通过与一种醇和金属烷醇盐进行酯交换反应转化为链烷醇酯的过程,优选通过与甲醇和甲醇钠进行酯交换反应转化为甲酯的过程是众所周知的。目前由甘油三酸酯制备甲酯的技术是采用间歇式和连续式两种工艺方法。在工业规模的间歇式工艺中,将甘油三酸酯、甲醇和甲醇钠一起加入到一个搅拌釜式反应器内,并于75-80℃下反应一段时间,通常约为1小时。然后关掉搅拌器,使混合物静置。甘油层将出现在底部,并从容器中排出。随后开动搅拌器,再加入一些甲醇钠,混合物于75-80℃下再反应1小时,排出甘油,粗甲酯用水洗涤并干燥。在一个连续生产过程中,将甘油三酸酯、甲醇和催化剂用泵计量混在一起并通过用泵将混合物经过一个静态混合器和管道长度送到一个沉降罐来实现混合。在此罐中,混合物被泵送到罐的一侧,在另一侧移出甲酯,甘油从底部排出。甲酯一离开此沉降罐,就进一步与另外的甲醇和催化剂混合,泵送通过静态混合器,经过管道,进入第二沉降罐。甲酯由比罐泵出,送去进一步精制。
按本发明的方法可采用任何类型的甘油三酸酯,包括但不限于椰子油、棕榈仁油、向日葵油、菜籽油、豆油、红花油和牛脂。
甲醇与甘油三酸酯的摩尔比可以是能在期望的时间内有效将基本全部甘油三酸酯转化为产物酯的任何比例。一般来说,甲醇与甘油三酸酯的摩尔比约3∶1,优选6∶1且最优选8∶1。优选的催化剂是金属甲醇盐如甲醇钠或甲醇钾。催化剂量可从约0.01%(重)到5%(重)变动,优选0.01-2%(重)且最优选0.03-1.5%(重)。
将甘油三酸酯引入适当的反应容器内,该反应器带有能将反应物混合到一起的设备如搅拌器或循环泵,并带有用来引入惰性气体如N2或CO2以避免最终产品变黑和氧化的设备。甘油三酸酯在反应器内被加热到50-90℃,优选到70-85℃且最优选到75-80℃。若使用循环泵,其规格应为所提供的物料周转率在1到20次/小时之间,优选2-15且最优选3-10次/小时。一旦甘油三酸酯被加热到75℃,将无水甲醇加催化剂一起加入到反应器内。甲醇与甘油三酸酯的摩尔比为3∶1,优选6∶1且最优选8∶1。催化剂量可从约0.01%(重)到5%(重)变动,优选0.01-2%(重)且最优选0.03-1.5%(重)。催化剂可以是金属烷醇盐,优选是金属甲醇盐如甲醇钾且最优选是甲醇钠。它们可通过加料口加入,优选由液面下加入,且最优选泵送到反应器液面下。将反应再回热到60-85℃,优选70-80℃,最优选75-80℃。一旦温度达到75-80℃,将反应器内的物料送到离心分离器,其实例之一参见美国专利5762800,引入全部内容作为参考。
按本发明的方法可以间歇式或连续式工艺实施。若在步骤(1)中少于基本全部量的羧酸酯转化为产物酯,可对本发明的方法进行改进。在这种情况下,可将第一次通过离心分离器的产物酯料流从离心分离器一或多次再循环到酯交换反应区,直到达到所期望的产物纯度。
按本发明方法的实施步骤还可以是将来自步骤(2)的链烷醇酯通过第二离心分离区,在此处将链烷醇酯与水接触来移出残留的甘油和其它杂质。
下面的实施例用来说明而非限定本发明。
实施例1
通过与甲醇钠和甲醇的酯交换反应制备豆油脂肪酸甲酯。一个2升水夹套反应器装上温度计、氮气液面下进气管、水冷凝器且不安装搅拌器。将约1.17mol或1000g色拉级豆油加入反应器。将水通入冷凝器,打开反应器的底阀并开动循环泵,水浴温度设定在90℃,并开始加热。当油的温度达到75℃时,将225g甲醇(表示有6mol过量)随0.08%(重)甲醇钠(25%的甲醇溶液)一起加入到反应器内。反应器为玻璃制品,因此可看到最初油相和甲醇是以两相存在。5分钟后,混合物变为均相,排出管线从泵切换到离心分离器(CostnerIndustries Nevada Corp.的V02型)的入口。离心分离器以2000rpm或33.5Hz的速度运转。重质相排出管线定为排放到烧杯中,轻质相出料管线定为从离心分离器返回到反应器顶部。甲醇和催化剂加入20分钟后,再加0.07%(重)甲醇钠。离心分离器第一次启动后5分钟将甘油排放到烧杯中。最初加入甲醇和催化剂45分钟后或第二次加入催化剂25分钟后,关闭离心分离器和泵。排空离心分离器,并与从离心分离器排出管线所收集的量合并。用气相色谱法进行分析,粗甲酯为98.5%甲酯、1.2%甘油单酯和0.3%甘油二酯。
Claims (12)
1.一种通过酯交换反应制备羧酸链烷醇酯的方法,包括如下步骤:(1)将一种羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括产物酯和产物醇的混合物;(2)将来自步骤(1)的反应混合物通过一个离心分离区,将第二醇与第二酯分离。
2.按权利要求1的方法,其中羧酸酯是甘油三酸酯。
3.按权利要求1的方法,其中醇是甲醇。
4.按权利要求1的方法,其中催化剂是甲醇钠。
5.一种制备羧酸链烷醇酯的方法,包括如下步骤:(1)将甘油三羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括链烷醇酯、甘油和未反应甘油三酸酯的混合物;(2)将来自步骤(1)的反应混合物通过一个离心分离区,形成重质甘油相和轻质相,其中甘油相与反应混合物连续分离;(3)将轻质相循环到步骤(1)。
6.按权利要求5的方法,其中甘油三酸酯选自椰子油、棕榈仁油、向日葵油、菜籽油、豆油、红花油和牛脂。
7.按权利要求5的方法,其中醇是甲醇。
8.按权利要求5的方法,其中催化剂是甲醇钠。
9.一种制备羧酸链烷醇酯的方法,包括如下步骤:(1)将甘油三羧酸酯与一种醇和一种有效量的酯交换催化剂在反应区进行反应,形成包括链烷醇酯和甘油的混合物;(2)将来自步骤(1)的反应混合物通过一个离心分离区,在此处将甘油与链烷醇酯分离;(3)将来自步骤(2)的链烷醇酯通过第二离心分离区,在此处将链烷醇酯与水接触来移出残留的甘油和其它杂质。
10.按权利要求9的方法,其中醇是甲醇。
11.按权利要求9的方法,其中催化剂是甲醇钠。
12.按权利要求9的方法,其中甘油三酸酯是豆油。
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US09/891,573 US6489496B2 (en) | 2000-07-12 | 2001-06-26 | Transesterification process |
US09/891,573 | 2001-06-26 |
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2001
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- 2001-06-29 AU AU7886301A patent/AU7886301A/xx active Pending
- 2001-06-29 WO PCT/US2001/020921 patent/WO2002004385A2/en not_active Application Discontinuation
- 2001-06-29 BR BR0112436-6A patent/BR0112436A/pt not_active Application Discontinuation
- 2001-06-29 EP EP01957086A patent/EP1299510A2/en not_active Withdrawn
- 2001-06-29 CA CA002415892A patent/CA2415892A1/en not_active Abandoned
- 2001-06-29 CN CN01812599A patent/CN1441837A/zh active Pending
- 2001-06-29 AU AU2001278863A patent/AU2001278863B2/en not_active Ceased
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Cited By (1)
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CN107583586A (zh) * | 2017-10-13 | 2018-01-16 | 安徽天意环保科技有限公司 | 表面活性剂的酯交换反应装置 |
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AU7886301A (en) | 2002-01-21 |
US6489496B2 (en) | 2002-12-03 |
CA2415892A1 (en) | 2002-01-17 |
US20020028961A1 (en) | 2002-03-07 |
AR028789A1 (es) | 2003-05-21 |
MY134010A (en) | 2007-11-30 |
AU2001278863B2 (en) | 2006-08-03 |
EP1299510A2 (en) | 2003-04-09 |
BR0112436A (pt) | 2003-12-30 |
WO2002004385A2 (en) | 2002-01-17 |
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