WO2014063456A1 - 一种牛磺酸的制备方法 - Google Patents

一种牛磺酸的制备方法 Download PDF

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Publication number
WO2014063456A1
WO2014063456A1 PCT/CN2013/071665 CN2013071665W WO2014063456A1 WO 2014063456 A1 WO2014063456 A1 WO 2014063456A1 CN 2013071665 W CN2013071665 W CN 2013071665W WO 2014063456 A1 WO2014063456 A1 WO 2014063456A1
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taurine
sodium
solution
ethylene oxide
taurate
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PCT/CN2013/071665
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English (en)
French (fr)
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陈勇
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潜江永安药业股份有限公司
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Priority to JP2014542708A priority Critical patent/JP5850550B2/ja
Priority to EP13719217.5A priority patent/EP2754652A1/en
Priority to US13/824,402 priority patent/US20140121405A1/en
Publication of WO2014063456A1 publication Critical patent/WO2014063456A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/18—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids

Definitions

  • the invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of taurine.
  • Taurine is a non-protein amino acid. It has anti-inflammatory, antipyretic, analgesic, anticonvulsant and blood pressure lowering effects. It has a good effect on infant brain development, nerve conduction, visual function improvement and calcium absorption. Taurine has a series of unique functions on the cardiovascular system, which can enhance physical fitness and relieve fatigue. Therefore, taurine is widely used in medical, food and health fields.
  • Taurine is prepared by biological extraction and chemical synthesis.
  • the former is rarely used due to raw materials and cost; currently used in industrial production mainly includes ethanolamine esterification method and ethylene oxide method.
  • ethylene oxide method has low cost and good product quality.
  • the environmental pollution is small, can be continuous and so on, is a process with obvious competitive advantages.
  • the ethylene oxide process is an emerging development process route.
  • the reaction principle is as follows:
  • taurine H 2 NCH 2 CH 2 SO 3 H
  • taurine H 2 NCH 2 CH 2 SO 3 H
  • 4 parts of the mother liquor have to be discharged, which not only causes waste of raw materials, but also has low yield, and Contamination of the environment, while the concentration of mother liquor requires a large amount of steam, resulting in higher energy consumption. Therefore, there is an urgent need to find an effective way to solve the above defects.
  • the main object of the present invention is to provide a preparation method of taurine which fully utilizes the sodium base in the system, recycles, does not introduce new raw materials or reagents, and also reduces some high-risk raw materials, thereby greatly simplifying the production process. , improve raw material utilization rate and product yield, and reduce production costs.
  • the present invention adopts the following technical solution: a method for preparing taurine, comprising the following steps:
  • the concentration concentration of the sodium taurate solution before the pH adjustment in the step (1) is 45% to 48%.
  • the substance for adjusting the pH in the step (1) is SO 2 or H 2 SO 3 .
  • the pH is adjusted to 4.5 to 9.0 by using SO 2 in the step (1).
  • the pH is adjusted to 5.5 to 6.5 by using SO 2 .
  • the solution is adjusted to a pH of 5.5-6.5 by using SO 2 , and ethylene oxide is formed to form sodium isethionate, wherein the sodium isethionate has a mass percentage of 48 to 55%.
  • ethylene oxide is introduced into the sodium taurate solution after adjusting the pH at 70 to 80 ° C, and the substance of sodium taurate and ethylene oxide in the solution The ratio is 1:1 ⁇ 1:1.2.
  • the volume percentage of ammonia accounts for 23 to 26% of the mixed solution.
  • the method for preparing taurine is used to prepare RNHCH 2 CH 2 SO 3 H and R(R')NCH 2 CH 2 SO 3 H.
  • the invention has the beneficial effects that the invention provides a method for preparing taurine, which utilizes the sodium balance in the system, recycles the mother liquor to the addition reaction to regenerate sodium taurate, and further synthesizes the extracted cattle. Sulfonic acid.
  • the invention fully utilizes the raw materials, solves the problem of using a large amount of high-risk chemical raw materials such as liquid alkali and concentrated sulfuric acid in the traditional process, thereby avoiding the production of a large amount of solid waste salt sodium sulfate, and also solving the traditional process of taurine mother liquor.
  • the secondary concentration is not well utilized and the environmental pollution problem caused by the discharge, and the steam required for the multiple concentration of the mother liquor is reduced, the yield is increased, and the production cost is also reduced.
  • the preparation method of the taurine provided by the embodiment of the invention comprises the following steps: after adjusting the pH value of the sodium taurate solution by using the S 4+ compound, the crude taurine is separated by crystallization, and the mother liquid is separated after the separation. The ethylene oxide is converted to sodium isethionate, and after adding ammonia, the reaction regenerates sodium taurate.
  • the taurine can be prepared by the following steps: after adjusting the pH of the sodium taurate solution by using the S 4+ compound, the ethylene oxide is further added to form a mixed solution of sodium isethionate and taurine, and then The crude taurine was separated, and after the separation, the mother liquor was added with ammonia to regenerate sodium taurate.

Abstract

本发明公开了一种牛磺酸的制备方法，包括如下步骤：将牛磺酸钠溶液采用S4+化合物调节pH值后，继续通入环氧乙烷转化成羟乙基磺酸钠，通入环氧乙烷前或后分离出牛磺酸粗品，羟乙基磺酸钠反应液再加氨后反应重新生成牛磺酸钠。本发明利用了系统中的钠基平衡，将母液循环利用至加成反应中重新生成牛磺酸钠，再进一步合成提取牛磺酸。本发明充分利用原料，解决了传统工艺中大量使用液碱与浓硫酸等高危险化学原料的问题，从而避免了产生大量固废盐硫酸钠，同时也解决了传统工艺中牛磺酸母液多次浓缩不能很好利用而排放带来的环境污染问题，再则也减少了母液多次浓缩所需要的蒸汽，提高了收率，降低了生产成本。

Description

一种牛磺酸的制备方法
技术领域
本发明属于有机化学合成技术领域，具体涉及一种牛磺酸的制备方法。
背景技术
牛磺酸是一种非蛋白质氨基酸，作为药物它具有消炎、解热、镇痛、抗惊厥和降低血压等作用，对婴幼儿大脑发育、神经传导、视觉机能的完善以及钙的吸收有良好作用，牛磺酸对心血管系统有一系列独特功能，能增强体质、解除疲劳，因此牛磺酸逐渐在医疗、食品保健等领域被广泛使用。
牛磺酸制备有生物提取法和化学合成法。前者受原料和成本影响，已很少采用；目前用于工业生产的主要有乙醇胺酯化法和环氧乙烷法，环氧乙烷法与乙醇胺酯化法相比，具有成本低，产品质量好，环境污染小，可连续化等优点，是竞争优势明显的工艺。
环氧乙烷法是一种新兴开发的工艺路线。其反应原理如下：
NaOH+SO2+CH2CH2O→HOCH2CH2SO3Na+NH3→H2NCH2CH2SO3Na+H2SO4→H2 NCH2CH2SO3H+Na2SO4
但是其中也存在一些弊端：①所使用液碱和硫酸等高危险化学原料，不仅容易腐蚀管道和设备，同时人操作时也容易引发安全事故，造成较大的经济损失；②大量硫酸钠固废产生，其中随着长时间的积累会带走部分牛磺酸，造成物料损失，同时硫酸钠始终会存在于母液中，其在高温高压的合成条件下，极易堵塞冷却器、加热器、合成塔和高压管道，造成生产无法正常进行，与此同时大量的硫酸盐固废增加劳动强度，且不易处理。③在后续提取过程中，牛磺酸（H2NCH2CH2SO3H）经多次提取，会产生大量废母液，④部分母液不得不排放掉，不仅造成原料浪费，收率低下，而且对环境造成污染，同时母液浓缩需消耗大量蒸汽，使得能耗较高。因此，急需寻求一个有效的方法解决以上缺陷。
发明内容
本发明的主要目的是提供一种牛磺酸的制备方法，其充分利用了系统中的钠基，循环利用，没有引入新的原料或试剂，同时还减少了部分高危原料，大大简化了生产工艺，提高了原料利用率和产品收率，降低了生产成本。
为了达到本发明的目的，本发明采用以下技术方案：一种牛磺酸的制备方法，包括如下步骤：
（1）将牛磺酸钠溶液采用S4+化合物调节pH值；
（2）通入环氧乙烷转化成羟乙基磺酸钠；
（3）通入环氧乙烷前或后分离出牛磺酸粗品；
（4）羟乙基磺酸钠反应液再加氨后反应重新生成牛磺酸钠。
优选地，所述步骤（1）中调节pH值前的牛磺酸钠溶液质量百分比浓度为45%~48%。
优选地，所述步骤（1）中调节pH值的物质是SO2或H2SO3。
优选地，所述步骤（1）中采用SO2调节pH值至4.5~9.0。
优选地，所述步骤（1）中采用SO2调节pH值至5.5~6.5。
优选地，所述采用SO2调节pH值至5.5-6.5的溶液，通入环氧乙烷生成羟乙基磺酸钠，其中羟乙基磺酸钠的质量百分比浓度为48~55%。
优选地，所述步骤（2）中在70~80℃下通入环氧乙烷到调节pH值后的牛磺酸钠溶液中，溶液中的牛磺酸钠与环氧乙烷的物质的量比为1:1~1:1.2。
优选地，所述步骤（4）中在羟乙基磺酸钠反应液中加氨后，氨的体积百分比占混合液的23~26%。
所述牛磺酸的制备方法用于制备RNHCH2CH2SO3H和R(R`)NCH2CH2SO3H。
本发明的有益效果是：本发明提供的一种牛磺酸的制备方法，其利用系统中的钠基平衡，将母液循环利用至加成反应中重新生成牛磺酸钠，再进一步合成提取牛磺酸。本发明充分利用了原料，解决了传统工艺中大量使用液碱与浓硫酸等高危险化学原料的问题，从而避免了产生大量固废盐硫酸钠，同时也解决了传统工艺中牛磺酸母液多次浓缩不能很好利用而排放带来的环境污染问题，再则也减少了母液多次浓缩所需要的蒸汽，提高了收率，也降低了生产成本。
具体实施方式
下面结合具体实施例对本发明所述技术方案作进一步的详细描述，以使本领域的技术人员可以更好的理解本发明并能予以实施，但所举实施例不作为对本发明的限定。
本发明实施例提供的一种牛磺酸的制备方法，包括如下步骤：将牛磺酸钠溶液采取S4+化合物调节pH值后，结晶分离出牛磺酸粗品，同时将分离后母液通入环氧乙烷转化成羟乙基磺酸钠，再加氨后反应重新生成牛磺酸钠。
另外，还可以通过如下步骤制成牛磺酸：将牛磺酸钠溶液采取S4+化合物调节pH值后，继续通入环氧乙烷生成羟乙基磺酸钠和牛磺酸混合溶液，再分离出牛磺酸粗品，分离后母液再加氨后反应重新生成牛磺酸钠。
反应原理如下：
Figure PCTCN2013071665-appb-C000001
实施例1：
取500ml、46%牛磺酸钠溶液于反应瓶中，搅拌下缓慢通入SO2至pH5.5停止，降至常温过滤，得到牛磺酸粗品，滤液移入反应瓶中，搅拌下于72℃时缓缓通入环氧乙烷（溶液中牛磺酸钠与环氧乙烷的物质的量比例为1:1），至反应达到终点（用碘滴数确定），然后将此反应液补加1015g NH3·H2O，在高压反应釜中加热至250℃，压力4.05MPa，反应1小时，降温出料，蒸发赶氨，得牛磺酸钠溶液。牛磺酸含量由HPLC测定，SO3 2-含量和羟乙基磺酸钠含量由离子色谱测定；结果如下，以质量百分比计：
牛磺酸粗品：数量：243g
牛磺酸含量：86.42%
SO3 2-含量：1.98%
牛磺酸钠溶液：数量：738g
牛磺酸钠含量（折牛磺酸）：39.16%
羟乙基磺酸钠含量：48.5%
实施例2：
取500ml、46%牛磺酸钠溶液于反应瓶中，搅拌下缓慢通入SO2至pH5.5停止，然后于75℃下缓慢通入环氧乙烷（溶液中牛磺酸钠与环氧乙烷的物质的量比例为1:1.1），至反应到达终点（用碘滴数确定），降至常温过滤，得牛磺酸的粗品，然后将此反应液补加1005g NH3·H2O，在高压反应釜中加热至253℃，压力4.1MPa，反应1小时，降温出料，蒸发赶氨，得牛磺酸钠溶液。结果如下，以质量百分比计：
牛磺酸粗品：数量：242g
牛磺酸含量：86.78%
SO3 2-含量：1.9%
牛磺酸钠溶液：数量：616g
牛磺酸钠含量（折牛磺酸）：39.15%
羟乙基磺酸钠含量：49.62%
实施例3：
取500ml、46%牛磺酸钠溶液于反应瓶中，搅拌下缓慢通入SO2至pH6.0停止，降至常温过滤，得到牛磺酸的粗品，滤液移入反应瓶中，搅拌下于78℃时缓缓通入环氧乙烷（溶液中牛磺酸钠与环氧乙烷的物质的量比例为1:1），至反应达到终点（用碘滴数确定），然后将此反应液补加1010g NH3·H2O，在高压反应釜中加热至255℃，压力4.15MPa，反应1.5小时，降温出料，蒸发赶氨，得牛磺酸钠溶液。结果如下，以质量百分比计：
牛磺酸粗品：数量：249g
牛磺酸含量：84.34%
SO3 2-含量：4.31%
牛磺酸钠溶液：数量：720g
牛磺酸钠含量（折牛磺酸）：39.16%
羟乙基磺酸钠含量：50.15%
实施例4：
取500ml、46%牛磺酸钠溶液于反应瓶中，搅拌下缓慢通入SO2至pH6.0停止，然后于80℃下缓慢通入环氧乙烷（溶液中牛磺酸钠与环氧乙烷的物质的量比例为1:1.2），至反应到达终点（用碘滴数确定），降至常温过滤，得牛磺酸的粗品，然后将此反应液补加1020g的NH3·H2O，在高压反应釜中加热至258℃，压力4.2MPa，反应1.5小时，降温出料，蒸发赶氨，得牛磺酸钠溶液。结果如下：
牛磺酸粗品：数量：246g
牛磺酸含量：85.36%
SO3 2-含量：3.76%
牛磺酸钠溶液：数量：607g
牛磺酸钠含量（折牛磺酸）：39.13%
羟乙基磺酸钠含量：52.86%

Claims (9)

  1. 一种牛磺酸的制备方法，其特征在于：包括如下步骤：
    （1）将牛磺酸钠溶液采用S4+化合物调节pH值；
    （2）通入环氧乙烷转化成羟乙基磺酸钠；
    （3）通入环氧乙烷前或后分离出牛磺酸粗品；
    （4）羟乙基磺酸钠反应液再加氨后反应重新生成牛磺酸钠。
  2. 根据权利要求1所述的牛磺酸的制备方法，其特征在于：所述步骤（1）中调节pH值前的牛磺酸钠溶液质量百分比浓度为45%~48%。
  3. 根据权利要求1所述的牛磺酸的制备方法，其特征在于：所述步骤（1）中调节pH值的物质是SO2或H2SO3。
  4. 根据权利要求1所述的牛磺酸的制备方法，其特征在于：所述步骤（1）中采用SO2调节pH值至4.5~9.0。
  5. 根据权利要求4所述的牛磺酸的制备方法，其特征在于：所述步骤（1）中采用SO2调节pH值至5.5~6.5。
  6. 根据权利要求5所述的牛磺酸的制备方法，其特征在于：所述步骤（2）中羟乙基磺酸钠的质量百分比浓度为48~55%。
  7. 根据权利要求1所述的牛磺酸的制备方法，其特征在于：所述步骤（2）中在70~80℃下通入环氧乙烷到调节pH值后的牛磺酸钠溶液中，溶液中的牛磺酸钠与环氧乙烷的物质的量比为1:1~1:1.2。
  8. 根据权利要求1所述的牛磺酸的制备方法，其特征在于：所述步骤（4）中在羟乙基磺酸钠反应液中加氨后，氨的体积百分比占混合液的23~26%。
  9. 权利要求1至8任一项所述的牛磺酸的制备方法，其特征在于：所述牛磺酸的制备方法用于制备RNHCH2CH2SO3H和R(R`)NCH2CH2SO3H。
PCT/CN2013/071665 2012-10-25 2013-02-19 一种牛磺酸的制备方法 WO2014063456A1 (zh)

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JP2014542708A JP5850550B2 (ja) 2012-10-25 2013-02-19 タウリンの製造方法
EP13719217.5A EP2754652A1 (en) 2012-10-25 2013-02-19 Taurine preparation method
US13/824,402 US20140121405A1 (en) 2012-10-25 2013-02-19 Process for producing taurine

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