α-乙酰-γ-丁内酯的合成机理研究及其应用
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摘要
α-乙酰-γ-丁内酯(ABL)是一重要的医药中间体和有机化工原料。尤其是随着维生素B1、延心痛、氯喹、杀菌剂丙硫菌唑、抗惊厥药物盐酸氯美噻唑、抗精神病药物利培酮嘧啶以及特殊医用高分子材料,在国内外市场上的不断开拓,对α-乙酰-γ-丁内酯的需求量也逐年增加。目前,α-乙酰-γ-丁内酯的合成方法主要有两种,其一：以γ-丁内酯和乙酸酯为原料,甲苯做溶剂,碱金属为缩合剂制备α-乙酰-γ-丁内酯的生产工艺；其二：以环氧乙烷和乙酰乙酸酯为原料的合成工艺。前者与后者相比,具有成本低、产率高、不安全隐患相对较小等优点。该工艺是国内目前工业化生产普遍使用的方法。但是,该生产工艺,使用甲苯做溶剂,并在金属钠熔融状态下滴加乙酸酯和γ-丁内酯的混合物,在反应引发阶段,产生大量极易气化的乙酸酯和反应生成的副产乙醇、氢气,经常发生冲料、燃烧、甚至爆炸等事故。另外,由于α-乙酰-γ-丁内酯在水中溶解度较大(约20%),后处理水相需要有机溶剂萃取,操作相对麻烦,污染严重。
本工作为使国内目前合成α-乙酰-γ-丁内酯工业化生产普遍采用的方法更加合理、安全、减少污染及简化操作,对其整个生产过程进行了系统的研究。揭示了α-乙酰-γ-丁内酯的反应机理；建立了一种收率高、相对安全、环境污染少、操作简便、易于工业化生产的合成新工艺。具体研究内容及结果如下：
1.揭示了α-乙酰-γ-丁内酯生成的反应机理
利用GC/MS联用对反应过程中物料组成的变化进行了跟踪检测,并采用密度泛函理论对其原料、产品以及可能生成的中间体的生成焓(△,H298)进行了计算,揭示了α-乙酰-γ-丁内酯生成的反应机理是：“γ-丁内酯在碱性条件下脱去一α-活泼氢形成其碳负离子,随后其在生成α-乙酰-γ-丁内酯过程中通过了两种途径,即：该碳负离子不但可直接进攻乙酸酯的羰基碳,形成α-乙酰-γ-丁内酯,而且该碳负离子还可进攻另一分子γ-丁内酯的羰基碳,形成其“二聚体”的碳负离子,该二聚体的碳负离子再与乙酸酯反应生成α-乙酰-γ-丁内酯”。
2.建立了“本底做溶剂代替甲苯合成α-乙酰-γ-丁内酯的新工艺”
α-乙酰-γ-丁内酯生成的反应机理表明,在合成α-乙酰-γ-丁内酯的过程中,可以不考虑由于原料局部过浓而产生副反应的问题。从而,用“本底做溶剂代替甲苯”,彻底避免了苯系物带来的环境污染；并通过调节金属钠比表面积实现了反应速率可控的目的,消除了冲料、着火等安全隐患；同时,通过选择中和用酸的种类、浓度、温度等条件,利用盐析原理,实现了油／水两相有效分离,取消了水相用有机溶剂萃取的操作,简化了后处理,生产成本每吨节省3100多元,收率从76%提高到了90%以上。建立了一条年产2000吨的工业化生产线。
3.建立了联产多种磷酸盐的废水处理方法
在生产α-乙酰-γ-丁内酯的过程中,每生产1吨α-乙酰-γ-丁内酯,同时产生副产物磷酸盐废水约2吨左右。对该废水为原料联产多种磷酸盐生产条件进行了系统的研究,建立了各项指标均符合国标要求的多种磷酸盐(磷酸二氢钠、磷酸氢二钠、磷酸钠、酸式焦磷酸钠、焦磷酸钠、三偏磷酸、六偏磷酸钠或三聚磷酸钠),联产新工艺。
4.建立了同时测定主副产物及原料气相色谱方法
为了实现对工业化生产的有效控制,采用毛细管气相色谱法,以己酸乙酯为内标物,建立了同时测定α-乙酰-γ-丁内酯、Y-丁内酯和α-(2-四氢呋喃亚基)--γ-丁内酯含量的方法,其线性范围分别在0～30.1335mg·mL-1、0～15.0810mg·mL-1和0～9.0600mg·mL-1的范围内被测组分浓度与被测组分与内标物峰面积比呈良好的线性关系,其相关系数均在0.9991以上；回收率在96.54～102.47%之间,相对标准偏差在0.08-2.48%之间。该方法具有良好的定量精确性和重复性,应用于α-乙酰-γ-丁内酯生产过程中中控及产品的含量分析,取得了满意的结果。
5.修订了“工业α-乙酰-γ-丁内酯”的质量标准
为确保该产品质量,满足下游产品的质量和生产要求,改变该产品现行标准落后的现状,建立相对科学、合理的产品质量标准。建立了以主成分α-乙酰-γ-丁内酯为内标,气相色谱校正面积归一化法同时测定主成分α-乙酰-γ-丁内酯和有害杂质苯和甲苯的方法。
a-Acetyl-y-butyrolactone (ABL) is an important drug intermediate and synthon in organic chemistry. As vitamin B1, delay heartache, chloroqhyll, fungicides prothioconazole, anti-convulsant drugs clomethiazole hydrochloride, the antipsychotic risperidone pyrimidine and special medical polymer materials, and are expanded the domestic and overseas markets constantly, the demand of ABL is also increased year by year. So far, there are only two published methods for ABL synthesis. The first one uses y-butyrolactone (GBL) and ethyl acetate (EtOAc) as raw materials, sodium as condensating agent and alkylbenzene as the solvent. The other method uses ethylene oxide and ethyl acetoacetate as raw materials. The former has more the advantages of low cost, high yield, unsafe hidden danger relatively small than the latter. The process is a commonly used method in domestic industrial production. However, the production process, using toluene as solvent, and mixtures of acetate and y-butyrolactone was added dropwise in the molten state of the sodium. In the inducing phase, a large amount of easily gasifiable acetate and the reaction generating byproduct of ethanol, hydrogen were produced. Red material, burning, even an explosion and other accidents were usually occured. In addition, due to a-acetyl-y-butyrolactone has larger solubility (about20%) in water. Water phase need organic solvent extract, post-processing operate relatively troublesome and serious pollution.
This work systematically studied the entire production process, in order to make domestic synthetic a-acetyl-y-butyrolactone industrial production commonly method is more reasonable, safe, reduce pollution and streamline operations. An environmentally friendly, safe, simple and efficient new method was been established for the synthesis of ABL with the yield higher. Specific research contents and results are as follows.
1. The mechanism of ABL synthesis was explored.
The mechanism of ABL synthesis from GBL and EtOAc was explored by detecting the material changes involved with GC/MS and the enthalpies of formation of the synthons, products, and possible intermediates were calculated using the density functional theory. GBL forms a carbanion of y-butyrolactone by losing an a-H under strongly alkaline conditions. ABL is then obtained via two reaction mechanisms. One of the reaction mechanisms involves direct reaction of the carbanion of y-butyrolactone with EtOAc to produce ABL. The other involves the formation of a carbanion of a-(2-hydroxy-tetrahydrofuran-2-yl)-y-butyrolactone through the reaction of two molecules of GBL, and the subsequent combination of this anion with EtOAc to produce ABL
2. Established the new process for synthetic ABL with raw material replacd toluene as solvent.
The mechanism of ABL synthesis showed that it is unnecessary to take into account raw materials'local thickness, and their self-condensation under these conditions in the synthesis of ABL process. Considering the reasons above, this work applied raw material replaced alkylbenzene as the solvent, and avoided environmental pollution by alkylbenzene; also, accidents such as red material and fire were avoided by specific surface area of sodium metal control. Meanwhile, through to selecting the type and concentration of acid, neutralizing temperature and other conditions, Effective isolation of the organic and aqueous phases was performed using the salting out method.
The operation of the aqueous phase using an organic solvent extraction was cancelled, and the post-processing was simplified. The production costs reduced more than3100yuan per ton, and the yield increased from76%to higher than90%. The industrialization production line with annual output of2,000t was established.
3. Established a treatment method for phosphate wastewater combined production of a variety of phosphate.
In the process of production ABL,1ton of ABL produces, meanwhile byproducts phosphate wastewater about2tons. Production conditions were systematically studied for Phosphate wastewater from the production ABL as raw material. A treatment method was established for phosphate wastewater combined production of a variety phosphate (sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, sodium trimetaphosphate, sodium hexametaphosphate, and sodium tripolyphosphate). The indexes of phosphate products were analyzed and the results showed all of them met the requirements of corresponding in dustrial phosphate standards.
4. A method for simultaneous determination of ABL, by-product and raw material was established by gas chromatography.
In order to achieved effective control of industrial production.A method for simultaneous determination contents of ABL, GBL and α-(2-tetrahydro furanylidene)-y-butyrolactone (AGBL) by gas chromatography was established with ethyl hexanoate as an internal standard. The method has been applied to the process in which GBL and ethyl acetate were used as raw material to produce ABL.The results showed that the peak area ratio of the measured component to the internal standard has a good linear relationship with component concentration in the range of the0-30.13g/L for ABL,0-15.08g/L for GBL and0-9.06g/L for AGBL, the correlation coefficients are more than0.9991, recoveries were between96.5-102.9%; Relative standard deviations were between0.10-2.50%. And the method is applied in ABL production process control and product analysis, and satisfactory results were obtained, which provides the basis for the optimization of the best technological conditions and establishments of product standards of ABL.
5. Revision of quality standard for industrial a-acetyl-y-butyrolactone
In order to ensure the product quality, meet the requirements of production and quality of downstream products, the current status of the backward standards for product are changed present, a relatively scientific and reasonable product quality standards was established. A method for simultaneous determination contents of ABL, benzene and toluene by gas chromatography was established with correction area normalization method using ABL as an internal standard.
本工作为使国内目前合成α-乙酰-γ-丁内酯工业化生产普遍采用的方法更加合理、安全、减少污染及简化操作,对其整个生产过程进行了系统的研究。揭示了α-乙酰-γ-丁内酯的反应机理；建立了一种收率高、相对安全、环境污染少、操作简便、易于工业化生产的合成新工艺。具体研究内容及结果如下：
1.揭示了α-乙酰-γ-丁内酯生成的反应机理
利用GC/MS联用对反应过程中物料组成的变化进行了跟踪检测,并采用密度泛函理论对其原料、产品以及可能生成的中间体的生成焓(△,H298)进行了计算,揭示了α-乙酰-γ-丁内酯生成的反应机理是：“γ-丁内酯在碱性条件下脱去一α-活泼氢形成其碳负离子,随后其在生成α-乙酰-γ-丁内酯过程中通过了两种途径,即：该碳负离子不但可直接进攻乙酸酯的羰基碳,形成α-乙酰-γ-丁内酯,而且该碳负离子还可进攻另一分子γ-丁内酯的羰基碳,形成其“二聚体”的碳负离子,该二聚体的碳负离子再与乙酸酯反应生成α-乙酰-γ-丁内酯”。
2.建立了“本底做溶剂代替甲苯合成α-乙酰-γ-丁内酯的新工艺”
α-乙酰-γ-丁内酯生成的反应机理表明,在合成α-乙酰-γ-丁内酯的过程中,可以不考虑由于原料局部过浓而产生副反应的问题。从而,用“本底做溶剂代替甲苯”,彻底避免了苯系物带来的环境污染；并通过调节金属钠比表面积实现了反应速率可控的目的,消除了冲料、着火等安全隐患；同时,通过选择中和用酸的种类、浓度、温度等条件,利用盐析原理,实现了油／水两相有效分离,取消了水相用有机溶剂萃取的操作,简化了后处理,生产成本每吨节省3100多元,收率从76%提高到了90%以上。建立了一条年产2000吨的工业化生产线。
3.建立了联产多种磷酸盐的废水处理方法
在生产α-乙酰-γ-丁内酯的过程中,每生产1吨α-乙酰-γ-丁内酯,同时产生副产物磷酸盐废水约2吨左右。对该废水为原料联产多种磷酸盐生产条件进行了系统的研究,建立了各项指标均符合国标要求的多种磷酸盐(磷酸二氢钠、磷酸氢二钠、磷酸钠、酸式焦磷酸钠、焦磷酸钠、三偏磷酸、六偏磷酸钠或三聚磷酸钠),联产新工艺。
4.建立了同时测定主副产物及原料气相色谱方法
为了实现对工业化生产的有效控制,采用毛细管气相色谱法,以己酸乙酯为内标物,建立了同时测定α-乙酰-γ-丁内酯、Y-丁内酯和α-(2-四氢呋喃亚基)--γ-丁内酯含量的方法,其线性范围分别在0～30.1335mg·mL-1、0～15.0810mg·mL-1和0～9.0600mg·mL-1的范围内被测组分浓度与被测组分与内标物峰面积比呈良好的线性关系,其相关系数均在0.9991以上；回收率在96.54～102.47%之间,相对标准偏差在0.08-2.48%之间。该方法具有良好的定量精确性和重复性,应用于α-乙酰-γ-丁内酯生产过程中中控及产品的含量分析,取得了满意的结果。
5.修订了“工业α-乙酰-γ-丁内酯”的质量标准
为确保该产品质量,满足下游产品的质量和生产要求,改变该产品现行标准落后的现状,建立相对科学、合理的产品质量标准。建立了以主成分α-乙酰-γ-丁内酯为内标,气相色谱校正面积归一化法同时测定主成分α-乙酰-γ-丁内酯和有害杂质苯和甲苯的方法。
a-Acetyl-y-butyrolactone (ABL) is an important drug intermediate and synthon in organic chemistry. As vitamin B1, delay heartache, chloroqhyll, fungicides prothioconazole, anti-convulsant drugs clomethiazole hydrochloride, the antipsychotic risperidone pyrimidine and special medical polymer materials, and are expanded the domestic and overseas markets constantly, the demand of ABL is also increased year by year. So far, there are only two published methods for ABL synthesis. The first one uses y-butyrolactone (GBL) and ethyl acetate (EtOAc) as raw materials, sodium as condensating agent and alkylbenzene as the solvent. The other method uses ethylene oxide and ethyl acetoacetate as raw materials. The former has more the advantages of low cost, high yield, unsafe hidden danger relatively small than the latter. The process is a commonly used method in domestic industrial production. However, the production process, using toluene as solvent, and mixtures of acetate and y-butyrolactone was added dropwise in the molten state of the sodium. In the inducing phase, a large amount of easily gasifiable acetate and the reaction generating byproduct of ethanol, hydrogen were produced. Red material, burning, even an explosion and other accidents were usually occured. In addition, due to a-acetyl-y-butyrolactone has larger solubility (about20%) in water. Water phase need organic solvent extract, post-processing operate relatively troublesome and serious pollution.
This work systematically studied the entire production process, in order to make domestic synthetic a-acetyl-y-butyrolactone industrial production commonly method is more reasonable, safe, reduce pollution and streamline operations. An environmentally friendly, safe, simple and efficient new method was been established for the synthesis of ABL with the yield higher. Specific research contents and results are as follows.
1. The mechanism of ABL synthesis was explored.
The mechanism of ABL synthesis from GBL and EtOAc was explored by detecting the material changes involved with GC/MS and the enthalpies of formation of the synthons, products, and possible intermediates were calculated using the density functional theory. GBL forms a carbanion of y-butyrolactone by losing an a-H under strongly alkaline conditions. ABL is then obtained via two reaction mechanisms. One of the reaction mechanisms involves direct reaction of the carbanion of y-butyrolactone with EtOAc to produce ABL. The other involves the formation of a carbanion of a-(2-hydroxy-tetrahydrofuran-2-yl)-y-butyrolactone through the reaction of two molecules of GBL, and the subsequent combination of this anion with EtOAc to produce ABL
2. Established the new process for synthetic ABL with raw material replacd toluene as solvent.
The mechanism of ABL synthesis showed that it is unnecessary to take into account raw materials'local thickness, and their self-condensation under these conditions in the synthesis of ABL process. Considering the reasons above, this work applied raw material replaced alkylbenzene as the solvent, and avoided environmental pollution by alkylbenzene; also, accidents such as red material and fire were avoided by specific surface area of sodium metal control. Meanwhile, through to selecting the type and concentration of acid, neutralizing temperature and other conditions, Effective isolation of the organic and aqueous phases was performed using the salting out method.
The operation of the aqueous phase using an organic solvent extraction was cancelled, and the post-processing was simplified. The production costs reduced more than3100yuan per ton, and the yield increased from76%to higher than90%. The industrialization production line with annual output of2,000t was established.
3. Established a treatment method for phosphate wastewater combined production of a variety of phosphate.
In the process of production ABL,1ton of ABL produces, meanwhile byproducts phosphate wastewater about2tons. Production conditions were systematically studied for Phosphate wastewater from the production ABL as raw material. A treatment method was established for phosphate wastewater combined production of a variety phosphate (sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, sodium trimetaphosphate, sodium hexametaphosphate, and sodium tripolyphosphate). The indexes of phosphate products were analyzed and the results showed all of them met the requirements of corresponding in dustrial phosphate standards.
4. A method for simultaneous determination of ABL, by-product and raw material was established by gas chromatography.
In order to achieved effective control of industrial production.A method for simultaneous determination contents of ABL, GBL and α-(2-tetrahydro furanylidene)-y-butyrolactone (AGBL) by gas chromatography was established with ethyl hexanoate as an internal standard. The method has been applied to the process in which GBL and ethyl acetate were used as raw material to produce ABL.The results showed that the peak area ratio of the measured component to the internal standard has a good linear relationship with component concentration in the range of the0-30.13g/L for ABL,0-15.08g/L for GBL and0-9.06g/L for AGBL, the correlation coefficients are more than0.9991, recoveries were between96.5-102.9%; Relative standard deviations were between0.10-2.50%. And the method is applied in ABL production process control and product analysis, and satisfactory results were obtained, which provides the basis for the optimization of the best technological conditions and establishments of product standards of ABL.
5. Revision of quality standard for industrial a-acetyl-y-butyrolactone
In order to ensure the product quality, meet the requirements of production and quality of downstream products, the current status of the backward standards for product are changed present, a relatively scientific and reasonable product quality standards was established. A method for simultaneous determination contents of ABL, benzene and toluene by gas chromatography was established with correction area normalization method using ABL as an internal standard.
引文
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