CN103936785B - 一种氯化磷酰胆碱钙盐四水合物的制备方法 - Google Patents
一种氯化磷酰胆碱钙盐四水合物的制备方法 Download PDFInfo
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- CN103936785B CN103936785B CN201410183015.6A CN201410183015A CN103936785B CN 103936785 B CN103936785 B CN 103936785B CN 201410183015 A CN201410183015 A CN 201410183015A CN 103936785 B CN103936785 B CN 103936785B
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- calcium
- choline
- phosphoryl chloride
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229960001231 choline Drugs 0.000 title claims abstract description 32
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 title claims abstract description 27
- MMFBVFWEERQGJK-UHFFFAOYSA-N calcium;tetrahydrate Chemical compound O.O.O.O.[Ca] MMFBVFWEERQGJK-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000007788 liquid Substances 0.000 claims abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 30
- 235000011007 phosphoric acid Nutrition 0.000 claims abstract description 28
- 239000007787 solid Substances 0.000 claims abstract description 22
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 19
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 17
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 17
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 17
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 15
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 claims abstract description 14
- 229940062672 calcium dihydrogen phosphate Drugs 0.000 claims abstract description 14
- 229910000389 calcium phosphate Inorganic materials 0.000 claims abstract description 14
- 235000019691 monocalcium phosphate Nutrition 0.000 claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 12
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 11
- 239000001110 calcium chloride Substances 0.000 claims abstract description 11
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 11
- 239000012141 concentrate Substances 0.000 claims abstract description 10
- 235000019700 dicalcium phosphate Nutrition 0.000 claims abstract description 10
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 17
- 239000010409 thin film Substances 0.000 claims description 11
- 238000001704 evaporation Methods 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000000108 ultra-filtration Methods 0.000 claims description 6
- 239000008247 solid mixture Substances 0.000 claims description 5
- DZNXQEJLVYZVSK-UHFFFAOYSA-N C(C)(=O)OCC[N+](C)(C)C.P(=O)(Cl)(Cl)Cl Chemical compound C(C)(=O)OCC[N+](C)(C)C.P(=O)(Cl)(Cl)Cl DZNXQEJLVYZVSK-UHFFFAOYSA-N 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 20
- 238000000034 method Methods 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 8
- 239000002699 waste material Substances 0.000 abstract description 5
- 239000012065 filter cake Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 230000008719 thickening Effects 0.000 abstract description 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000008213 purified water Substances 0.000 description 12
- 235000019743 Choline chloride Nutrition 0.000 description 9
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 8
- 229960003178 choline chloride Drugs 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 229960005069 calcium Drugs 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- -1 phosphoryl chloride choline calcium salt Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000011759 adducin Human genes 0.000 description 3
- 108010076723 adducin Proteins 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- ICVPTJCCKTXCDT-UHFFFAOYSA-L calcium;2-(trimethylazaniumyl)ethyl phosphate;chloride Chemical compound [Cl-].[Ca+2].C[N+](C)(C)CCOP([O-])([O-])=O ICVPTJCCKTXCDT-UHFFFAOYSA-L 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000005374 membrane filtration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000005457 optimization Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229950004354 phosphorylcholine Drugs 0.000 description 2
- PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- AZRZBCASYOBNKQ-UHFFFAOYSA-N 6-chloro-3,5-diaminopyrazine-3-carboxamide Chemical compound CN(C)C(N)=NC(=O)C1=NC(Cl)=C(N)N=C1N AZRZBCASYOBNKQ-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000011172 small scale experimental method Methods 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Abstract
Description
外观 | 白色结晶性粉末 |
含水量 | 19.0~23.0% |
pH(1克溶于100ml水) | 7.0~8.5 |
滴定含量(干基) | 97.0%~102.0% |
含氯量 | 10.0%~11.5% |
含钙量 | 11.5%~13.0% |
含磷量 | 8.6~10.0% |
Claims (3)
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CN201410183015.6A CN103936785B (zh) | 2014-05-04 | 2014-05-04 | 一种氯化磷酰胆碱钙盐四水合物的制备方法 |
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CN201410183015.6A CN103936785B (zh) | 2014-05-04 | 2014-05-04 | 一种氯化磷酰胆碱钙盐四水合物的制备方法 |
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CN103936785A CN103936785A (zh) | 2014-07-23 |
CN103936785B true CN103936785B (zh) | 2016-05-18 |
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CN104892664A (zh) * | 2015-05-07 | 2015-09-09 | 芜湖福民生物药业有限公司 | 氯化磷酰胆碱钙盐四水化合物的制备方法 |
CN106083918B (zh) * | 2016-06-08 | 2018-07-06 | 芜湖福民生物药业有限公司 | 氯化磷酰胆碱钙盐四水化合物的制备方法 |
CN108546273B (zh) * | 2018-02-05 | 2020-12-15 | 浙江云涛生物技术股份有限公司 | 一种制备氯化磷酰胆碱钙盐的新工艺 |
CN108610359B (zh) * | 2018-04-21 | 2020-05-29 | 山东奥博生物科技有限公司 | 氯化磷酰胆碱钙盐的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102584891A (zh) * | 2012-01-13 | 2012-07-18 | 太仓市茜泾化工有限公司 | 一种氯化磷酰胆碱钙盐的制备方法 |
CN103694271A (zh) * | 2013-12-02 | 2014-04-02 | 常熟富士莱医药化工有限公司 | 氯化磷酰胆碱钙盐的制备方法 |
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CN102584891A (zh) * | 2012-01-13 | 2012-07-18 | 太仓市茜泾化工有限公司 | 一种氯化磷酰胆碱钙盐的制备方法 |
CN103694271A (zh) * | 2013-12-02 | 2014-04-02 | 常熟富士莱医药化工有限公司 | 氯化磷酰胆碱钙盐的制备方法 |
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Application publication date: 20140723 Assignee: Nantong Nabaiyuan Chemical Co., Ltd. Assignor: Suzhou Tianma Fine Chemical Product Co., Ltd. Contract record no.: 2016320010025 Denomination of invention: Method for preparing phosphorylcholine chloride calcium salt tetrahydrate Granted publication date: 20160518 License type: Exclusive License Record date: 20160615 |
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Effective date of registration: 20180727 Address after: No. 122, Hu Guan Zhen Lu Qing Road, Suzhou, Jiangsu, Jiangsu Patentee after: Suzhou Tianma Pharmaceutical Co., Ltd. Address before: 215101 Huayuan East Road, Mu Du Town, Wuzhong District, Suzhou, Jiangsu 199-1 Patentee before: Suzhou Tianma Fine Chemical Product Co., Ltd. |
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Address after: Suzhou City, Jiangsu province 215000 Guan Hu Zhen Hu Qing Road No. 122 Patentee after: Suzhou Zhengji Pharmaceutical Co.,Ltd. Address before: Suzhou City, Jiangsu province 215000 Guan Hu Zhen Hu Qing Road No. 122 Patentee before: SUZHOU TIANMA PHARMACEUTICAL Co.,Ltd. |
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EC01 | Cancellation of recordation of patent licensing contract |
Assignee: NANTONG NABAIYUAN CHEMICAL Co.,Ltd. Assignor: SUZHOU TIANMA SPECIALTY CHEMICALS Co.,Ltd. Contract record no.: 2016320010025 Date of cancellation: 20201021 |