CN102060901A - 由双烯醇酮醋酸酯合成***的工艺方法 - Google Patents
由双烯醇酮醋酸酯合成***的工艺方法 Download PDFInfo
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- CN102060901A CN102060901A CN 201110007898 CN201110007898A CN102060901A CN 102060901 A CN102060901 A CN 102060901A CN 201110007898 CN201110007898 CN 201110007898 CN 201110007898 A CN201110007898 A CN 201110007898A CN 102060901 A CN102060901 A CN 102060901A
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- Prior art keywords
- progesterone
- hydrogenation
- temperature
- ethanol
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- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 title claims abstract description 68
- 229960003387 progesterone Drugs 0.000 title claims abstract description 30
- 239000000186 progesterone Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title abstract description 19
- MZWRIOUCMXPLKV-RFOVXIPZSA-N 16-Dehydropregnenolone acetate Chemical compound C([C@@H]12)C[C@]3(C)C(C(C)=O)=CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 MZWRIOUCMXPLKV-RFOVXIPZSA-N 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 150000001993 dienes Chemical class 0.000 claims description 14
- 235000019439 ethyl acetate Nutrition 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000002994 raw material Substances 0.000 claims description 7
- 238000007670 refining Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000012047 saturated solution Substances 0.000 claims description 5
- 238000003457 Shi epoxidation reaction Methods 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 238000003672 processing method Methods 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 238000004062 sedimentation Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- 239000006228 supernatant Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000012535 impurity Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- -1 methyl alcohol hydride Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Steroid Compounds (AREA)
Abstract
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Application Number | Priority Date | Filing Date | Title |
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CN201110007898A CN102060901B (zh) | 2011-01-14 | 2011-01-14 | 由双烯醇酮醋酸酯合成***的工艺方法 |
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CN201110007898A CN102060901B (zh) | 2011-01-14 | 2011-01-14 | 由双烯醇酮醋酸酯合成***的工艺方法 |
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CN102060901A true CN102060901A (zh) | 2011-05-18 |
CN102060901B CN102060901B (zh) | 2012-09-05 |
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CN201110007898A Expired - Fee Related CN102060901B (zh) | 2011-01-14 | 2011-01-14 | 由双烯醇酮醋酸酯合成***的工艺方法 |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102911232A (zh) * | 2012-11-02 | 2013-02-06 | 湖北丹江口丹澳医药化工有限公司 | 一种***的制备方法 |
CN103087136A (zh) * | 2012-11-06 | 2013-05-08 | 湖南科源生物制品有限公司 | 一种制备***的新工艺 |
CN103113453A (zh) * | 2013-02-04 | 2013-05-22 | 湖北民生生物医药有限公司 | 一种减压浓缩替代冲馏生产沃氏氧化物的工艺方法 |
CN103524588A (zh) * | 2013-11-04 | 2014-01-22 | 浙江神洲药业有限公司 | 一种制备***的方法 |
CN103641880A (zh) * | 2013-11-18 | 2014-03-19 | 陕西汉江药业集团股份有限公司 | 一种从***生产母液中回收***的方法 |
CN104130305A (zh) * | 2014-07-15 | 2014-11-05 | 湖北葛店人福药业有限责任公司 | 一种合成***中间体孕烯醇醋酸酯的方法 |
CN105732757A (zh) * | 2016-03-02 | 2016-07-06 | 湖南科瑞生物制药股份有限公司 | ***的制备方法 |
CN106589036A (zh) * | 2016-12-11 | 2017-04-26 | 湖北竹溪人福药业有限责任公司 | 一种***及其异构体的分离方法 |
CN113956318A (zh) * | 2021-09-10 | 2022-01-21 | 丽江映华生物药业有限公司 | 一种***的精制方法 |
CN113999275A (zh) * | 2021-11-30 | 2022-02-01 | 陕西众和振华生物科技有限公司 | 一种***母液综合回收处理的碳中和工艺 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB512954A (en) * | 1937-03-29 | 1939-09-29 | Chem Ind Basel | Manufacture of ketones or secondary alcohols of the cyclopentanopolyhydrophenanthrene series |
-
2011
- 2011-01-14 CN CN201110007898A patent/CN102060901B/zh not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB512954A (en) * | 1937-03-29 | 1939-09-29 | Chem Ind Basel | Manufacture of ketones or secondary alcohols of the cyclopentanopolyhydrophenanthrene series |
Non-Patent Citations (1)
Title |
---|
《中国医药工业杂志》 20021231 严智娟等 3beta-羟基孕甾-5-烯-20-酮-3-醋酸酯的合成工艺改进 528页 1 第33卷, 第11期 * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102911232B (zh) * | 2012-11-02 | 2015-03-11 | 湖北丹澳药业有限公司 | 一种***的制备方法 |
CN102911232A (zh) * | 2012-11-02 | 2013-02-06 | 湖北丹江口丹澳医药化工有限公司 | 一种***的制备方法 |
CN103087136A (zh) * | 2012-11-06 | 2013-05-08 | 湖南科源生物制品有限公司 | 一种制备***的新工艺 |
CN103113453B (zh) * | 2013-02-04 | 2016-03-16 | 湖北民生生物医药有限公司 | 一种减压浓缩替代冲馏生产沃氏氧化物的工艺方法 |
CN103113453A (zh) * | 2013-02-04 | 2013-05-22 | 湖北民生生物医药有限公司 | 一种减压浓缩替代冲馏生产沃氏氧化物的工艺方法 |
CN103524588A (zh) * | 2013-11-04 | 2014-01-22 | 浙江神洲药业有限公司 | 一种制备***的方法 |
CN103524588B (zh) * | 2013-11-04 | 2015-09-23 | 浙江神洲药业有限公司 | 一种制备***的方法 |
CN103641880A (zh) * | 2013-11-18 | 2014-03-19 | 陕西汉江药业集团股份有限公司 | 一种从***生产母液中回收***的方法 |
CN103641880B (zh) * | 2013-11-18 | 2015-09-09 | 陕西汉江药业集团股份有限公司 | 一种从***生产母液中回收***的方法 |
CN104130305A (zh) * | 2014-07-15 | 2014-11-05 | 湖北葛店人福药业有限责任公司 | 一种合成***中间体孕烯醇醋酸酯的方法 |
CN105732757A (zh) * | 2016-03-02 | 2016-07-06 | 湖南科瑞生物制药股份有限公司 | ***的制备方法 |
CN106589036A (zh) * | 2016-12-11 | 2017-04-26 | 湖北竹溪人福药业有限责任公司 | 一种***及其异构体的分离方法 |
CN106589036B (zh) * | 2016-12-11 | 2018-07-24 | 湖北竹溪人福药业有限责任公司 | 一种***及其异构体的分离方法 |
CN113956318A (zh) * | 2021-09-10 | 2022-01-21 | 丽江映华生物药业有限公司 | 一种***的精制方法 |
CN113999275A (zh) * | 2021-11-30 | 2022-02-01 | 陕西众和振华生物科技有限公司 | 一种***母液综合回收处理的碳中和工艺 |
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CN102060901B (zh) | 2012-09-05 |
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Denomination of invention: Process for synthesizing progesterone by using dehydropregnenolone acetate Effective date of registration: 20121227 Granted publication date: 20120905 Pledgee: Jiang Shou commercial (China) Trading Co.,Ltd. Pledgor: HUBEI FANGTONG PHARMACEUTICAL Co.,Ltd. Registration number: 2012990000853 |
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Date of cancellation: 20141121 Granted publication date: 20120905 Pledgee: Jiang Shou commercial (China) Trading Co.,Ltd. Pledgor: HUBEI FANGTONG PHARMACEUTICAL Co.,Ltd. Registration number: 2012990000853 |
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