CN109134403B - 一种2-吗啉乙磺酸的制备方法 - Google Patents
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- HNXGGWNCFXZSAI-UHFFFAOYSA-N 2-morpholin-2-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCC1CNCCO1 HNXGGWNCFXZSAI-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000007710 freezing Methods 0.000 claims abstract description 9
- 230000008014 freezing Effects 0.000 claims abstract description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 8
- AKTHLFYZKHPYBY-UHFFFAOYSA-M sodium;1-chloroethanesulfonate Chemical compound [Na+].CC(Cl)S([O-])(=O)=O AKTHLFYZKHPYBY-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 239000011780 sodium chloride Substances 0.000 claims abstract description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 abstract description 11
- 238000010992 reflux Methods 0.000 abstract description 8
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 abstract description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- HBZSTRIPIRCTOW-UHFFFAOYSA-N 2-morpholin-2-ylethanesulfonic acid hydrate Chemical compound O.OS(=O)(=O)CCC1CNCCO1 HBZSTRIPIRCTOW-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VNJUXIZTRBJJSK-UHFFFAOYSA-M sodium 1-chloroethanesulfonate hydrate Chemical compound CC(S(=O)(=O)[O-])Cl.O.[Na+] VNJUXIZTRBJJSK-UHFFFAOYSA-M 0.000 description 5
- 239000002994 raw material Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UMJJNXFVAMHNIE-UHFFFAOYSA-N ClCC[Na] Chemical compound ClCC[Na] UMJJNXFVAMHNIE-UHFFFAOYSA-N 0.000 description 1
- ALTIBIYWDZVHMD-UHFFFAOYSA-N [Na].ClC(C)S(=O)(=O)O Chemical compound [Na].ClC(C)S(=O)(=O)O ALTIBIYWDZVHMD-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000006177 biological buffer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- -1 sodium alkyl benzene Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及乙磺酸衍生物，尤其涉及一种吗啉乙磺酸的制备方法。一种2‑吗啉乙磺酸的制备方法，将吗啉和氯代乙磺酸钠的有机溶液，在加热回流的条件下测量pH值，当pH值下降至9时，慢慢加入甲醇钠控制反应体系的pH值，反应完成后，得到2‑吗啉乙磺酸的甲醇溶液，加入盐酸溶液后，将pH值调节至5，热过滤除去氯化钠，得到2‑吗啉乙磺酸溶液冷冻结晶，将结晶的晶体离心分离后即得到2‑吗啉乙磺酸。
Description
技术领域
本发明涉及乙磺酸衍生物，尤其涉及一种吗啉乙磺酸的制备方法。
背景技术
吗啉乙磺酸是一种非常重要的生物缓冲剂，常用于各种植物的原生质体的分离与培养。也可以适用于香皂和肥皂中，可用作钙皂分散剂。也是主要的洗涤剂活性物，可代替部分烷基苯磺酸钠和三聚磷酸钠，制成低磷或无磷洗涤剂。
当前常规的合成路线是将吗啉与乙烯基磺酸钠进行开环反应，最后中和。其中原料价格较高，导致成本高。而开环反应时，容易产生副产物，导致反应效率不高，导致最终产物质量不高。
发明内容
本发明旨在解决现有技术的不足，提供了一种2-吗啉乙磺酸的制备方法。本发明生产效率高，成本更低，产物质量好。
本发明一种2-吗啉乙磺酸的制备方法，将吗啉和氯代乙磺酸钠的有机溶液，在加热回流的条件(温度控制在60-70℃)下测量pH值，当pH值下降至9时，慢慢加入甲醇钠控制反应体系的pH值，反应完成后，得到2-吗啉乙磺酸的甲醇溶液，加入盐酸溶液后，将pH值调节至5，热过滤除去氯化钠，得到2-吗啉乙磺酸溶液冷冻结晶，将结晶的晶体离心分离后即得到2-吗啉乙磺酸。
所述的一种2-吗啉乙磺酸的制备方法，所述2-吗啉乙磺酸的收率达90％以上，纯度≥99％(HPLC)。
所述的一种2-吗啉乙磺酸的制备方法，所述甲醇的含水量低于1％，所述吗啉纯度为99.5％。
所述的一种2-吗啉乙磺酸的制备方法，所述吗啉与有机溶剂的质量比为1∶3。
所述的一种2-吗啉乙磺酸的制备方法，所述吗啉与氯代乙磺酸钠的摩尔质量比为1∶1.1。
本发明直接采用常见易得的吗啉、氯代乙磺酸钠为原料，成本低。此外，由于原料结构和产物结构近，合成效率高，最终产物质量也更好。
具体实施方式
本发明一种2-吗啉乙磺酸的制备方法，将吗啉和氯代乙磺酸钠的有机溶液，在加热回流的条件(温度控制在60-70℃)下测量pH值，当pH值下降至9时，慢慢加入甲醇钠控制反应体系的pH值，反应完成后，得到2-吗啉乙磺酸的甲醇溶液，加入盐酸溶液后，将pH值调节至5，热过滤除去氯化钠，得到2-吗啉乙磺酸溶液冷冻结晶，将结晶的晶体离心分离后即得到2-吗啉乙磺酸。
实施例1
在500ml的三口瓶中加入200克甲醇后，加入50克吗啉和116克一水氯代乙磺酸钠，将三口瓶加热至甲醇回流(温度控制在60-70℃)，30分钟后开始测三口瓶内的pH值，当pH值下降至9左右时，开始加入甲醇钠与甲醇的混合液控制pH值至9左右，反应8小时后，通过TLC点板分析吗啉已反应完全后，开始滴加盐酸至pH值为5后，热过滤除盐，将三口瓶进行冷却结晶，得到即为2-吗啉乙磺酸粗品，将得到的粗品溶于80％甲醇溶液，并在加热的条件下加入2克活性碳脱色后，得到的2-吗啉乙磺酸溶液冷冻结晶，即得到2-吗啉乙磺酸一水合物，该2-吗啉乙磺酸烘干得到成品103克；收率92.46％，纯度99.21％(HPLC)。
实施例2
在500ml的三口瓶中加入200克乙醇后，加入50克吗啉和116克一水氯代乙磺酸钠，将三口瓶加热至乙醇回流(温度控制在75-85℃)，30分钟后开始测三口瓶内的pH值，当pH值下降至9左右时，开始加入乙醇钠与乙醇的混合液控制pH值至9左右，反应8小时后，通过TLC点板分析吗啉已反应完全后，开始滴加盐酸至pH值为5后，热过滤除盐，将三口瓶进行冷却结晶，得到即为2-吗啉乙磺酸粗品，将得到的粗品溶于80％乙醇溶液，并在加热的条件下加入2克活性碳脱色后，得到的2-吗啉乙磺酸溶液冷冻结晶，即得到2-吗啉乙磺酸一水合物，该2-吗啉乙磺酸烘干得到成品97克；收率87.5％，纯度98.66％(HPLC)。
实施例3
在500L的反应釜中加入200公斤甲醇后，加入50公斤吗啉和116公斤一水氯代乙磺酸钠，将反应釜加热至甲醇回流(温度控制在60-70℃)，30分钟后开始测反应釜内的pH值，当pH值下降至9左右时，开始加入甲醇钠与甲醇的混合液控制pH值至9左右，反应8小时后，通过TLC点板分析吗啉已反应完全后，开始滴加盐酸至pH值为5后，热过滤除盐，将反应釜进行冷却结晶，得到即为2-吗啉乙磺酸粗品，将得到的粗品溶于80％甲醇溶液，并在加热的条件下加入2公斤活性碳脱色后，得到的2-吗啉乙磺酸溶液冷冻结晶，即得到2-吗啉乙磺酸一水合物，该2-吗啉乙磺酸烘干得到成品107公斤；收率96.05％，纯度99.51％(HPLC)。
实施例4
在2000L的反应釜中加入800公斤甲醇后，加入200公斤吗啉和464公斤一水氯代乙磺酸钠，将反应釜加热至甲醇回流(温度控制在60-70℃)，30分钟后开始测反应釜内的pH值，当pH值下降至9左右时，开始加入甲醇钠与甲醇的混合液控制pH值至9左右，反应8小时后，通过TLC点板分析吗啉已反应完全后，开始滴加盐酸至pH值为5后，热过滤除盐，将反应釜进行冷却结晶，得到即为2-吗啉乙磺酸粗品，将得到的粗品溶于80％甲醇溶液，并在加热的条件下加入8公斤活性碳脱色后，得到的2-吗啉乙磺酸溶液冷冻结晶，即得到2-吗啉乙磺酸一水合物，该2-吗啉乙磺酸烘干得到成品420公斤；收率94.2％，纯度99.22％(HPLC)。
实施例5
在2000L的反应釜中加入800公斤甲醇后，加入200公斤吗啉和422公斤一水氯代乙磺酸钠，将反应釜加热至甲醇回流(温度控制在60-70℃)，30分钟后开始测反应釜内的pH值，当pH值下降至9左右时，开始加入甲醇钠与甲醇的混合液控制pH值至9左右，反应8小时后，通过TLC点板分析吗啉已反应完全后，开始滴加盐酸至pH值为5后，热过滤除盐，将反应釜进行冷却结晶，得到即为2-吗啉乙磺酸粗品，将得到的粗品溶于80％甲醇溶液，并在加热的条件下加入8公斤活性碳脱色后，得到的2-吗啉乙磺酸溶液冷冻结晶，即得到2-吗啉乙磺酸一水合物，该2-吗啉乙磺酸烘干得到成品391公斤；收率87.7％，纯度97.03％(HPLC)。
Claims (5)
1.一种2-吗啉乙磺酸的制备方法，其特征是将吗啉和氯代乙磺酸钠的有机溶液，在加热回流的条件，温度控制在60-70℃下测量pH值，当pH值下降至9时，慢慢加入甲醇钠控制反应体系的pH值，反应完成后，得到2-吗啉乙磺酸的甲醇溶液，加入盐酸溶液，将pH值调节至5，热过滤除去氯化钠，得到2-吗啉乙磺酸溶液冷冻结晶，将结晶的晶体离心分离后即得到2-吗啉乙磺酸。
2.根据权利要求1所述的一种2-吗啉乙磺酸的制备方法，其特征在于，所述2-吗啉乙磺酸的收率达90％以上，HPLC纯度≥99％。
3.根据权利要求1所述的一种2-吗啉乙磺酸的制备方法，其特征在于，所述甲醇的含水量低于1％，所述吗啉纯度为99.5％。
4.根据权利要求1或3所述的一种2-吗啉乙磺酸的制备方法，其特征在于，所述吗啉与有机溶剂的质量比为1∶3。
5.根据权利要求1所述的一种2-吗啉乙磺酸的制备方法，其特征在于，所述吗啉与氯代乙磺酸钠的摩尔质量比为1∶1.1。
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