WO2010045780A1 - 高纯度叔丁醇镁的制备方法 - Google Patents

高纯度叔丁醇镁的制备方法 Download PDF

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WO2010045780A1
WO2010045780A1 PCT/CN2009/000989 CN2009000989W WO2010045780A1 WO 2010045780 A1 WO2010045780 A1 WO 2010045780A1 CN 2009000989 W CN2009000989 W CN 2009000989W WO 2010045780 A1 WO2010045780 A1 WO 2010045780A1
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magnesium
tert
reaction
ester
alcohol
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俞迪虎
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上海奥锐特国际贸易有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/68—Preparation of metal alcoholates
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency

Definitions

  • the present invention relates to medicinal chemistry. Specifically, it relates to a method for preparing high-purity magnesium tert-butoxide. Background technique:
  • Magnesium methoxide can be prepared by direct reaction of magnesium with anhydrous methanol.
  • the synthesis of magnesium alkoxides, such as magnesium ethoxide, of higher primary alcohols (C ⁇ 2 alcohols) cannot be obtained by direct reaction of alcohols with magnesium metal under normal conditions. It is usually necessary to add a certain catalyst (mercury or iodine, see US2287088, DE 1230004). ) to accelerate the reaction or high temperature and high pressure reaction (about 130 ° C, lOatm, see DE 2261386).
  • the addition of the catalyst not only increases the cost and easily forms harmful impurities which are difficult to remove, but also causes environmental pollution and operation difficulties; and the high temperature and high pressure increase the cost of the equipment, thereby synthesizing the magnesium alkoxide compound other than magnesium methoxide by direct synthesis for industrial production. There are certain limitations.
  • No. 6,544,446 describes a process for the preparation of magnesium alkoxide which is obtained by reacting magnesium metal with isoprene to form a magnesium diisoprene adduct, which is then reacted with an alcohol to give a high yield of magnesium alkoxide. Preparation method. However, there is a certain risk in handling the double isoprene magnesium adduct.
  • US2005159630 describes a process for the preparation of an alcohol metal by the exchange of a higher alcohol with an alcohol of a lower alcohol metal to give a higher alcohol metal, the claims comprising all alkaline earth metals, wherein claim 4 comprises tert-butanol, but the embodiment does not exemplify Preparation of magnesium butoxide.
  • the present inventors have studied and repeated the process described in US2005159630 for the preparation of magnesium tert-butoxide, which does not give high purity magnesium tert-butoxide containing about 30% of magnesium methoxide which has not been completely exchanged.
  • magnesium tert-butoxide in the reaction system is too low, so that the magnesium tert-butoxide formed during the alcohol exchange reaction is quickly saturated and precipitated in the reaction mixture, and the unreacted magnesium methoxide is trapped and not removed in time. Methanol, this part of magnesium methoxide is no longer involved in the reaction and remains in the magnesium tert-butoxide, resulting in a final purity of only 70% of magnesium tert-butoxide.
  • the technical problem to be solved by the present invention is to overcome the above-mentioned deficiencies and design a preparation method of high-purity magnesium t-butoxide.
  • the invention provides a preparation method of high-purity magnesium tert-butoxide, which uses a lower alkyl magnesium alkoxide and a t-butanol ester as a starting material, and a t-butanol ester and a lower alkyl magnesium alkoxide in a reactive distillation (or distillation)
  • the transfer esterification reaction is carried out under conditions, and the low-boiling ester formed by the reaction is removed from the reaction system by distillation (or distillation). After the reaction is completed, excess t-butanol ester is removed by a conventional method to obtain high purity.
  • Magnesium tert-butoxide which uses a lower alkyl magnesium alkoxide and a t-butanol ester as a starting material, and a t-butanol ester and a lower alkyl magnesium alkoxide in a reactive distillation (or distillation)
  • the transfer esterification reaction is carried out under conditions, and the low-
  • the method of the present invention is specifically as follows: under the protection of nitrogen, the starting material lower magnesium alkoxide and t-butanol ester are added to a reaction device having a rectification (or distillation) device at a certain molar ratio, and when the reaction starts and reaches equilibrium, The temperature at the top of the rectification (or distillation) is close to the boiling point of the low-boiling ester produced by the reaction, and the low-boiling ester is produced as a by-product of the distillation. When the distillate (or distillation) distillate no longer contains the low-boiling ester, the reaction is completed. Excess t-butanol ester was removed by a conventional method, and after drying, an almost theoretical amount of product was obtained, white porous solid high purity magnesium tert-butoxide, purity 92% - 98%.
  • the present invention is based on the following principle - the inventors have found through experiments that a high purity magnesium tert-butoxide can be conveniently obtained by a transfer esterification reaction between a lower magnesium alkoxide and a t-butanol ester.
  • the reaction formula is as follows: (RO) 2 Mg + t-BuOR, , (t-BuO) 2 Mg + ROR,
  • R is ( ⁇ (: 4 fluorenyl, ! ⁇ is ⁇ ) decanoyl.
  • This reaction is a reversible reaction. According to the general principle of chemical reaction equilibrium, it is beneficial to increase the amount of reactants or remove the product in time during the reaction.
  • the lower magnesium decyl alcohol of the present invention is ⁇ (: 4 magnesium alkoxide, including magnesium methoxide, magnesium ethoxide, magnesium n-propoxide, magnesium isopropoxide, magnesium n-butoxide, magnesium isobutoxide, pure solid can be used A mixture of magnesium alkoxide or various magnesium alkoxides, or an alcohol solution or suspension thereof, may be used.
  • the alcohol in the alcohol solution or suspension is an alkyl alcohol of ⁇ (: 4 .
  • the lower magnesium decyl alcohol is also It may be a low-purity magnesium tert-butoxide obtained by other synthetic methods.
  • the lower-grade magnesium decyl alcohol may be used in the "one-pot" process, or purchased.
  • the tert-butanol ester is tert-butanol ( 4 ⁇ -lower fatty acid ester, including tert-butyl formate, tert-butyl acetate, tert-butyl propionate, tert-butyl butyrate, tert-butyl isobutyrate .
  • the molar ratio of the tert-butyl alcohol ester to the sum of all the lower alcohols in the reaction system is not less than 0.2: 1.
  • the molar ratio is less than 0.2: 1
  • the lower magnesium alkoxide does not react.
  • suitable molar ratio is 1 ⁇ 5: 1, can be larger, but will not affect the reaction results and is not economical.
  • the transfer esterification reaction between the lower alkyl magnesium alkoxide and the t-butanol ester is carried out in a reaction apparatus having a rectification (or distillation) apparatus, and the low-boiling ester formed by the reaction can be removed in time.
  • Reactive distillation (or distillation) can be carried out using a highly efficient rectification unit to reduce the amount of t-butanol ester used; it can also be a simple distillation with a large excess of t-butanol ester to remove the low boiling esters formed by the reaction.
  • the temperature and pressure of the reaction fine (or distillation) process are not limited by the physical properties of the starting materials and by-product low boiling esters.
  • Example 1 Take 1800 g of t-butyl acetate in a 2000 ml stirred four-necked flask. The reaction flask was equipped with a precision rectification column with an inner diameter of 15 mm and a height of 800 mm. Heated to 95 ° C under N 2 protection and accelerated at 15 ml/min. The rate was added to 409 g of a 4.1% solution of magnesium methoxide in methanol, and a white precipitate appeared at the beginning.
  • the pot temperature was 95 ° C, and the distillation temperature at the top of the column was 57.
  • the reflux ratio was set to 1.
  • the distillation temperature of the column also increases, gradually increasing from 57 ° C to 97 ° C, at this time the overhead does not contain Methyl acetate, all t-butyl acetate.
  • the reflux ratio is adjusted to 5 as the temperature at the top of the tower is gradually increased, and finally adjusted to 20.
  • the retort concentrating device is a vacuum concentrating device, concentrated under reduced pressure to dryness, to obtain 100 g of white porous solid magnesium tert-butoxide, purity 94.5 %.
  • the reflux ratio is adjusted to 20.
  • the smelting apparatus is a vacuum concentrating apparatus, and the mixture is concentrated to dryness under reduced pressure to give 105 g of a white porous solid, magnesium tert-butoxide, having a purity of 95.5%.
  • the retort concentrating device is a vacuum concentrating device, concentrated under reduced pressure to dryness, to give 100.5 g of white porous solid magnesium tert-butoxide, purity 93.5 %.
  • Example 2 tert-butyl acetate was used in place of tert-butyl acetate.
  • the reaction temperature was gradually increased from 32 ° C to 82 ° C, and the reaction time was required to be 5 hours. There was obtained 108 g of a white porous solid of magnesium tert-butoxide having a purity of 98 ° /. .
  • Example 6
  • magnesium methoxide (50% by weight of magnesium tert-butoxide, 50% by weight of magnesium methoxide) was purchased in place of magnesium methoxide for 6 hours. 80 g of a white porous solid, magnesium tert-butoxide, was obtained with a purity of 92%.

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

高纯度叔丁醇镁的制备方法 技术领域：
本发明涉及药物化学。 具体涉及高纯度叔丁醇镁的制备方法。 背景技术：
醇镁化合物是醇金属化合物的一种， 它的分子结构为 Mg(OR)2， R=烷基。 它是一种对水敏感的固体， 主要应用于有机合成的选择性 碱， 无水体系中的中和剂， 制备高纯度氧化镁的原料， 化学中间体和 聚烯烃的催化剂载体。由于二价金属镁离子可以和羰基形成稳定的螯 合物， 所以醇镁化合物比如甲醇镁可以作为选择性羰基凝聚剂。近年 来随着金属醇盐溶胶-凝胶法的迅速发展， 醇镁化合物也得到了多方 面的应用， 其潜在的应用前景亦引人注目。
甲醇镁可以通过镁和无水甲醇直接反应制备。 更高级伯醇 (C≥ 2 的醇)的醇镁， 如乙醇镁的合成， 在一般条件下不能通过醇和金属镁 直接反应得到，通常需要加入一定的催化剂（汞或碘，见 US2287088, DE 1230004 ) 来加速反应或高温高压反应 （约 130 °C， lOatm，见 DE2261386) 。 加入催化剂不仅使成本增高并且容易形成不易除去的 有害杂质， 以及造成环境污染和操作困难； 而高温高压又增加了设备 的成本，因而用直接合成法合成除甲醇镁外的醇镁化合物对于工业化 生产有一定局限性。
众所周知， 具有支链的醇镁都不能通过醇和金属镁直接反应得 到。
US6544446描述了一种制备醇镁的方法， 由金属镁与异戊二烯反 应生成双异戊二烯镁加合物， 然后与醇反应得到高收率醇镁， 实例给 出了叔丁醇镁的制备方法。但处理双异戊二烯镁加合物是存在一定的 危险性的。
US2005159630 描述了一种制备醇金属的方法， 利用高级醇与低 级醇金属的醇交换得到高级醇金属， 其权利要求包含所有碱土金属， 其中权利要求 4包含叔丁醇， 但实施例未例举叔丁醇镁的制备。 本发明人在研究并重复 US2005159630所描述的过程用于制备叔 丁醇镁时， 并不能得到高纯度的叔丁醇镁， 其中含有约 30 %的未被 完全交换的甲醇镁。研究发现， 由于叔丁醇镁在反应体系中的溶解度 太低，导致醇交换反应过程生成的叔丁醇镁在反应混合物中很快饱和 析出， 裹夹了未反应的甲醇镁和未及时移走甲醇， 这部分甲醇镁不再 参与反应而一直残留在叔丁醇镁中，造成最终叔丁醇镁的纯度只能达 到 70%。
由 Nata l i ya Ya. Turova 等人编著的 《 THE CHEM I STRY OF METALALKOX I DES》中提出一种叔丁醇锆的制备方法， 利用醋酸叔丁酯 与异丙醇锆的转移酯化反应得到叔丁醇锆。 发明内容：
本发明所要解决的技术问题在于克服上述不足之处，设计一种高 纯度叔丁醇镁的制备方法。
本发明提供了一种高纯度叔丁醇镁的制备方法,采用低级烷基醇 镁和叔丁醇酯为起始原料， 叔丁醇酯与低级烷基醇镁在反应精馏（或 蒸馏）条件下进行转移酯化反应， 反应生成的低沸点酯通过精馏（或 蒸馏）的方法从反应体系中移去， 反应完成后， 采用常规方法移去过 量的叔丁醇酯， 即得到高纯度叔丁醇镁。
本发明方法具体如下： 在氮气保护下， 将起始原料低级醇镁和叔 丁醇酯按一定的摩尔比加入具有精馏 （或蒸馏） 装置的反应设备中， 反应幵始并达到平衡时， 精馏（或蒸馏）塔顶温度接近反应副产低沸 点酯的沸点， 蒸出反应副产低沸点酯， 当精熘（或蒸馏） 的馏出物中 不再含有低沸点酯时，反应完成，采用常规方法移去过量的叔丁醇酯， 干燥后， 得到几乎理论量的产品， 白色多孔状固体高纯度叔丁醇镁， 纯度 92 %_98%。
本发明基于下列原理- 本发明人经过试验研究发现，用低级醇镁与叔丁醇酯间的转移酯 化反应可以很方便地得到高纯度叔丁醇镁。 反应式如下： (RO)2Mg + t-BuOR, ， (t-BuO)2Mg + ROR,
式中 R 为（^〜(：4的垸基， ！^为^〜 的垸酰基。
此反应为可逆反应， 按照化学反应平衡一般原理， 在反应过程中 增加反应物的用量或及时移走产物都有利于反应趋于完全。
本发明所述低级垸基醇镁为 〜(：4的醇镁，包括甲醇镁，乙醇镁， 正丙醇镁， 异丙醇镁， 正丁醇镁， 异丁醇镁， 可以使用纯的固体醇镁 或各种醇镁的混合物， 也可以使用它们的醇溶液或悬混液。所述醇溶 液或悬混液中的醇为 〜(：4的烷基醇。作为特例， 低级垸基醇镁还可 以是其他合成方法得到的低纯度叔丁醇镁。 低级垸基醇镁可以使用 "一锅法"现制现用， 或外购。
所述叔丁醇酯为叔丁醇的 （^〜( 4低级脂肪酸酯， 包括甲酸叔丁 酯， 乙酸叔丁酯， 丙酸叔丁酯， 丁酸叔丁酯， 异丁酸叔丁酯。
叔丁醇酯与反应体系中所有低级醇总和（包含低级醇镁中的醇和 溶剂的醇） 的摩尔比不小于 0. 2: 1， 当摩尔比小于 0. 2: 1， 低级醇 镁反应不充分， 残留在产品中， 影响产品纯度； 合适的摩尔比是 1〜 5： 1， 可以更大， 但不会对反应结果产生影响而且也不经济。 '
低级烷基醇镁与叔丁醇酯间的转移酯化反应是在具有精馏（或蒸 馏）装置的反应设备进行， 反应生成的低沸点酯能被及时移去。 反应 精馏（或蒸馏）可以采用高效的精馏装置， 减少叔丁醇酯使用量； 也 可以是简单蒸馏， 用大过量的叔丁醇酯带走反应生成的低沸点酯。
反应精镏（或蒸馏）过程的温度和压力依据起始原料和副产物低 沸点酯不同物理性质而定， 没有严格限制。
以下用实施例说明本发明，但实施例不代表权利要求所涵盖的全 部范围。 具体实施方式： 实施例 1 取 1800g乙酸叔丁酯置于 2000ml带搅拌的四口瓶中， 反应瓶 装置有内径 15 毫米高度 800毫米的精密精馏柱， N2保护下加热至 95°C , 以 15ml/min的滴加速率加入 409gl4.1 %的甲醇镁甲醇溶液， 一开始即出现白色沉淀。 滴加完毕后釜温为 95°C， 塔顶馏出温度为 57 , 此时设回流比为 1。 随着乙酸甲酯的逐渐蒸出和釜温的逐渐升 高， 塔顶馏出温度也随之升高， 逐渐从 57°C慢慢升至 97°C， 此时塔 顶馏出液不含有乙酸甲酯， 全部为乙酸叔丁酯。 同时随着塔顶温度的 逐渐升高将回流比调为 5， 最后调为 20。 当塔顶温度稳定在 97Γ较 长一段时间后 (1小时)， 停止蒸馏， 反应时间大约需要 14小时。 改精 馏装置为减压浓缩装置， 减压浓缩至干， 得到 100克白色多孔状固体 叔丁醇镁， 纯度 94. 5 %。
实施例 2
取 600g乙酸叔丁酯置于 1000ml带搅拌的四口瓶中，反应瓶装置 有内径 15毫米高度 800毫米的精密精馏柱， N2保护下，加入 50克固 体甲醇镁，将悬混液加热至回流， 全回流 2小时， 当塔顶温度为 57°C 时， 此时设回流比为 5。 随着乙酸甲酯的逐渐蒸出， 塔顶馏出温度也 随之升高， 逐渐从 57T慢慢升至 97° (：， 此时塔顶馏出液不含有乙酸 甲酯， 全部为乙酸叔丁酯。 同时随着塔顶温度的逐渐升高将回流比调 为 20。 当塔顶温度稳定在 97°C较长一段时间后 (1小时)， 停止蒸馏， 反应时间大约需要 8小时。改精馏装置为减压浓縮装置， 减压浓缩至 干， 得到 105克白色多孔状固体叔丁醇镁， 纯度 95. 5%。 实施例 3
取 500g乙酸叔丁酯置于 1000ml带搅拌的四口瓶中，反应瓶装置 有内径 15毫米高度 800毫米的精密精馏柱， N2保护下，加入 65克固 体乙醇镁，将悬混液加热至回流， 全回流 2小时， 当塔顶温度为 77°C 时， 此时设回流比为 10。 随着乙酸乙酯的逐渐蒸出， 塔顶馏出温度 也随之升高， 逐渐从 77°C慢慢升至 97°C， 此时塔顶馏出液不含有乙 酸乙酯， 全部为乙酸叔丁酯。 同时随着塔顶温度的逐渐升高将回流比 调为 20。当塔顶温度稳定在 97°C较长一段时间后 (1小时)，停止蒸馏， 反应时间大约需要 10小时。 改精馏装置为减压浓缩装置， 减压浓缩 至干， 得到 100.5克白色多孔状固体叔丁醇镁， 纯度 93. 5 %。 实施例 4
取 600g乙酸叔丁酯置于 1000ml带搅拌的四口瓶中，反应瓶装置 有回流冷凝管， N2保护下，加入 50克固体甲醇镁， 将悬混液加热至回 流， 回流 4小时后， 改回流冷凝管为简单蒸馏冷凝管， 边蒸熘边滴加 500g 乙酸叔丁酯， 随着乙酸甲酯的逐渐蒸出， 反应混合物温度也随 之升高， 慢慢升至 97°C， 此时塔顶馏出液不含有乙酸甲酯， 全部为 乙酸叔丁酯。 反应时间需要 15小时。 直接减压浓缩至干， 得到 101 克白色多孔状固体叔丁醇镁， 纯度 92 %。 实施例 5
按照实施例 2， 用甲酸叔丁酯代替乙酸叔丁酯， 反应温度从 32°C 慢慢升至 82°C， 反应时间需要 5小时。 得到 108克白色多孔状固体 叔丁醇镁， 纯度 98°/。。 实施例 6
按照实施例 2， 用外购的低纯度叔丁醇镁 （叔丁醇镁 50%wt,甲 醇镁 50%wt ) 代替甲醇镁， 反应时间需要 6小时。 得到 80克白色多 孔状固体叔丁醇镁， 纯度 92 %。

Claims

权 利 要 求 ,1、 一种高纯度叔丁醇镁的制备方法,其特征在于该方法包括下列 步骤：
( 1 ) 采用低级醇镁和叔丁醇酯作起始原料， 在氮气保护下， 加入 具有精馏或蒸馏装置的反应设备中， 加热至沸腾；
( 2 ) 反应开始并达到平衡时，精馏或蒸馏塔顶温度接近反应副产 物低沸点酯的沸点， 蒸出反应副产物低沸点酯， 当精馏或蒸 馏的馏出物中不再含有低沸点酯时， 反应完成；
( 3 ) 采用常规方法移去过量的叔丁醇酯，干燥后， 即得到高纯度
2、 按照权利要求 1所述的方法， 其特征在于所述叔丁醇酯为甲酸 叔丁酯、 乙酸叔丁酯、 丙酸叔丁酯、 丁酸叔丁酯或异丁酸叔丁 酯。
3、 按照权利要求 1所述的方法， 其特征在于所述低级烷基醇镁为 〜(：4的烷基醇镁中的一种或多种混合物或它们的醇溶液或悬 混液。
4、 按照权利要求 3所述的方法， 其特征在于所述醇溶液或悬混液 中的醇为（^〜( 4的烷基醇。
5、 按照权利要求 1所述的方法， 其特征在于所述低级垸基醇镁为 甲醇镁、 乙醇镁、 正丙醇镁、 异丙醇镁、 正丁醇镁、 叔丁醇镁 或异丁醇镁。
6、 按照权利要求 1所述的方法， 其特征在于所述低级烷基醇镁为 叔丁醇镁与苺 基醇镁的混合物。 , ,
7、 按照权利要求 1所述的方法， 其特征 于叔.丁醇酯与反应体系 中所有低级醇总和， 即低级醇镁中的 ^和溶剂的醇总和的摩尔 比为 0. 2-20： 1 ?
8、 按照权利要求 '6所述的方法， 其特征在于叔丁醇酯与反应体系 中所有低级醇总和， 即低级醇镁中的醇和溶剂的醇总和的摩尔 比为 1〜5： 1。
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CN102603476B (zh) * 2012-02-06 2013-11-27 扬州三友合成化工有限公司 高纯度高级醇镁的一种合成方法

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