类质同晶甾体化合物的分离过程研究
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摘要
11α-羟基16α,17α-环氧黄体酮(简称HEP)是一种重要的激素药物中间体。工业上,HEP通过微生物转化16α,17α-环氧黄体酮(简称EP)制得,过程转化率约为40-45%。为解决工业生产中存在的HEP和EP分离难、收率低、产品质量不稳定等问题,本文对HEP和EP的分离工艺进行了系统的研究,建立了将萃取与溶析结晶耦合的“萃取溶析结晶”工艺,以及“浸取-结晶”和“浸取-吸附”集成的分离新工艺,并成功应用于HEP和EP的分离纯化。
根据HEP和EP分子与晶体结构的相似性,提出了HEP和EP在溶液结晶过程中形成了固体溶液型混晶的假设。通过设计实验制备出了不同质量比的HEP/EP混晶产品,并采用XRD、DSC以及HPLC等表征手段证明了该假设的正确性。从而说明结晶法分离纯化HEP和EP必须靠多级结晶完成。
测定了HEP和EP在8种纯溶剂和不同组成的甲苯-氯仿混合溶剂中的溶解度;研究了溶液热力学,特别是EP和HEP相对溶解度对于结晶纯化HEP的影响。发现同一溶剂中,EP相对于HEP的溶解度越大,结晶所得HEP纯度越高,氯仿-甲苯混合溶剂最适合HEP的分离纯化。
对开发新型分离HEP和EP工艺进行了探索性的研究。提出将萃取分离与溶析结晶分离相耦合的萃取溶析结晶技术并成功应用于HEP和EP的分离。进而研究了对原料进行浸取分离的预处理方式,将浸取过程与溶析-蒸发结晶过程组合,通过一次浸取预处理,再两次重结晶实现了HEP的分离纯化,该工艺较工厂分离工艺减少两次溶解,两次结晶和一次过滤操作,节约成本25～30%左右。
此外,还对经过浸取分离预处理后的原料,经溶剂溶解后进行吸附分离的浸取-吸附分离工艺过程首次进行了系统研究和优化。对吸附分离过程进行了系统的研究和优化。根据溶解度数据以及溶解度参数等理论,选择甲醇作为溶剂,氯仿作为洗脱剂,非极性大孔吸附树脂为吸附剂的吸附过程来实现HEP和EP的分离。通过吸附热力学与动力学数据的测定和关联,筛选树脂,优化了工艺条件;采用固定床吸附实现了HEP和EP的分离。吸附分离与原料的浸取预处理相结合,采用一步浸取一步吸附即可实现HEP和EP的分离,此工艺方案亦表现出很大的工业应用潜力。同时针对固定床吸附分离HEP和EP过程,完成了数学建模和模拟求解,为以后工业放大提供了基础模型依据。
上述有关研究内容尚未见国内外文献报道。
11α-Hydroxy-16α,17α-epoxyprogesterone (abbreviated as HEP) is an important intermediate for synthesis of hormone pharmaceuticals. In industry, HEP is prepared from 16α,17α-epoxyprogesterone (abbreviated as EP) through bioconversion with low conversion (about 40~45%). The separation and purification of HEP is difficult with low yield and poor product quality. To solve these problems, a systematic study on the separation process of HEP and EP was performed, and three different new processes for separation and purification of HEP have been developed in this thesis. According to the similarity in the molecular and crystal structures of HEP and EP, the solid solution formation of the two steroids when they were crystallized from solution were postulated and then confirmed based on the X-ray diffraction crystal structure determination, thermal analysis and composition analysis of the prepared HEP/EP solid solution crystals. This indicates that several stages or times crystallization is needed to get pure HEP crystals.
The solubility of HEP and EP in eight different pure solvents and chloroform-toluene mixed solvents with four different compositions were determined. The effect of relative solubility on the crystal purity was studied. The experimental results show that the bigger the relative solubility of EP to HEP is, the higher the purity of HEP crystals can be obtained. Toluene-chloroform mixed solvents afford the most effective enhancement of HEP crystal purity.
Novel separation process was studied and compared. The extractive drowning out crystallization was proposed and successfully used for separation and purification of HEP and EP for the first time. Then, combinative separation processes of leaching with crystallization were proposed. HEP was separated and purified through once leaching and twice recrystallization. The efficiency of purification increased 25~30% compared with the current five times recrystallization in industry.
Also a leaching-adsorption process was proposed and showed big potential for industrial application. The leaching-adsorption process was studied in detail. The isothermal adsorption equilibrium of HEP and EP on different adsorbates were determined. Screening of adsorbate, solvent and diluting solvent were performed. Also the adsorption kinetics of HEP and EP on the selected adsorbent were measured. The separation of HEP and EP by fixed bed adsorption was studied. The breakthrough and elution curves were determined, the process parameters were optimized. HEP was purified through once leaching and once following adsorptive separation. The modeling for the fixed bed adsorption was performed and solved. This work affords basic data and important foundation for the scaling up of the process.
All the contents above have never been founded in any type documents.
根据HEP和EP分子与晶体结构的相似性,提出了HEP和EP在溶液结晶过程中形成了固体溶液型混晶的假设。通过设计实验制备出了不同质量比的HEP/EP混晶产品,并采用XRD、DSC以及HPLC等表征手段证明了该假设的正确性。从而说明结晶法分离纯化HEP和EP必须靠多级结晶完成。
测定了HEP和EP在8种纯溶剂和不同组成的甲苯-氯仿混合溶剂中的溶解度;研究了溶液热力学,特别是EP和HEP相对溶解度对于结晶纯化HEP的影响。发现同一溶剂中,EP相对于HEP的溶解度越大,结晶所得HEP纯度越高,氯仿-甲苯混合溶剂最适合HEP的分离纯化。
对开发新型分离HEP和EP工艺进行了探索性的研究。提出将萃取分离与溶析结晶分离相耦合的萃取溶析结晶技术并成功应用于HEP和EP的分离。进而研究了对原料进行浸取分离的预处理方式,将浸取过程与溶析-蒸发结晶过程组合,通过一次浸取预处理,再两次重结晶实现了HEP的分离纯化,该工艺较工厂分离工艺减少两次溶解,两次结晶和一次过滤操作,节约成本25～30%左右。
此外,还对经过浸取分离预处理后的原料,经溶剂溶解后进行吸附分离的浸取-吸附分离工艺过程首次进行了系统研究和优化。对吸附分离过程进行了系统的研究和优化。根据溶解度数据以及溶解度参数等理论,选择甲醇作为溶剂,氯仿作为洗脱剂,非极性大孔吸附树脂为吸附剂的吸附过程来实现HEP和EP的分离。通过吸附热力学与动力学数据的测定和关联,筛选树脂,优化了工艺条件;采用固定床吸附实现了HEP和EP的分离。吸附分离与原料的浸取预处理相结合,采用一步浸取一步吸附即可实现HEP和EP的分离,此工艺方案亦表现出很大的工业应用潜力。同时针对固定床吸附分离HEP和EP过程,完成了数学建模和模拟求解,为以后工业放大提供了基础模型依据。
上述有关研究内容尚未见国内外文献报道。
11α-Hydroxy-16α,17α-epoxyprogesterone (abbreviated as HEP) is an important intermediate for synthesis of hormone pharmaceuticals. In industry, HEP is prepared from 16α,17α-epoxyprogesterone (abbreviated as EP) through bioconversion with low conversion (about 40~45%). The separation and purification of HEP is difficult with low yield and poor product quality. To solve these problems, a systematic study on the separation process of HEP and EP was performed, and three different new processes for separation and purification of HEP have been developed in this thesis. According to the similarity in the molecular and crystal structures of HEP and EP, the solid solution formation of the two steroids when they were crystallized from solution were postulated and then confirmed based on the X-ray diffraction crystal structure determination, thermal analysis and composition analysis of the prepared HEP/EP solid solution crystals. This indicates that several stages or times crystallization is needed to get pure HEP crystals.
The solubility of HEP and EP in eight different pure solvents and chloroform-toluene mixed solvents with four different compositions were determined. The effect of relative solubility on the crystal purity was studied. The experimental results show that the bigger the relative solubility of EP to HEP is, the higher the purity of HEP crystals can be obtained. Toluene-chloroform mixed solvents afford the most effective enhancement of HEP crystal purity.
Novel separation process was studied and compared. The extractive drowning out crystallization was proposed and successfully used for separation and purification of HEP and EP for the first time. Then, combinative separation processes of leaching with crystallization were proposed. HEP was separated and purified through once leaching and twice recrystallization. The efficiency of purification increased 25~30% compared with the current five times recrystallization in industry.
Also a leaching-adsorption process was proposed and showed big potential for industrial application. The leaching-adsorption process was studied in detail. The isothermal adsorption equilibrium of HEP and EP on different adsorbates were determined. Screening of adsorbate, solvent and diluting solvent were performed. Also the adsorption kinetics of HEP and EP on the selected adsorbent were measured. The separation of HEP and EP by fixed bed adsorption was studied. The breakthrough and elution curves were determined, the process parameters were optimized. HEP was purified through once leaching and once following adsorptive separation. The modeling for the fixed bed adsorption was performed and solved. This work affords basic data and important foundation for the scaling up of the process.
All the contents above have never been founded in any type documents.
引文
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