JP2015501331A - タウリンの製造方法 - Google Patents
タウリンの製造方法 Download PDFInfo
- Publication number
- JP2015501331A JP2015501331A JP2014542708A JP2014542708A JP2015501331A JP 2015501331 A JP2015501331 A JP 2015501331A JP 2014542708 A JP2014542708 A JP 2014542708A JP 2014542708 A JP2014542708 A JP 2014542708A JP 2015501331 A JP2015501331 A JP 2015501331A
- Authority
- JP
- Japan
- Prior art keywords
- taurine
- sodium
- solution
- ethylene oxide
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 title claims abstract description 144
- 229960003080 taurine Drugs 0.000 title claims abstract description 72
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 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 abstract description 28
- 239000011734 sodium Substances 0.000 claims abstract description 28
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 25
- CZDZQGXAHZVGPL-UHFFFAOYSA-M sodium;1-hydroxyethanesulfonate Chemical compound [Na+].CC(O)S([O-])(=O)=O CZDZQGXAHZVGPL-UHFFFAOYSA-M 0.000 claims abstract description 16
- OTTPFCJTQXRWHO-UHFFFAOYSA-N 3-(2,3-dichloroanilino)cyclohex-2-en-1-one Chemical compound ClC1=CC=CC(NC=2CCCC(=O)C=2)=C1Cl OTTPFCJTQXRWHO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 12
- 239000012452 mother liquor Substances 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract description 5
- 235000011152 sodium sulphate Nutrition 0.000 abstract description 5
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 4
- 235000011121 sodium hydroxide Nutrition 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- -1 analgesic Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000004382 visual function Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/18—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
タウリン含有量:86.42%
SO3 2−含有量:1.98%
タウリンナトリウム溶液(重量):738g
タウリンナトリウム含有量(タウリンに換算して):39.16%
ヒドロキシエタンスルホン酸ナトリウム含有量:48.5%
タウリン含有量:86.78%
SO3 2−含有量:1.9%
タウリンナトリウム溶液(重量):616g
タウリンナトリウム含有量(タウリンに換算して):39.15%
ヒドロキシエタンスルホン酸ナトリウム含有量:49.62%
タウリン含有量:84.34%
SO3 2−含有量:4.31%
タウリンナトリウム溶液(重量):720g
タウリンナトリウム含有量(タウリンに換算して):39.16%
ヒドロキシエタンスルホン酸ナトリウム含有量:50.15%
タウリン含有量:85.36%
SO3 2−含有量:3.76%
タウリンナトリウム溶液(重量):607g
タウリンナトリウム含有量(タウリンに換算して):39.13%
ヒドロキシエタンスルホン酸ナトリウム含有量:52.86%
Claims (9)
- 1)タウリンナトリウム溶液に対してS4+化合物を用いてpH値の調整を行うステップと、
2)エチレンオキシドを導入してヒドロキシエタンスルホン酸ナトリウムに変換させるステップと、
3)エチレンオキシドを導入する直前または直後においてタウリンを粗分離するステップと、
4)ヒドロキシエタンスルホン酸ナトリウムの反応液にアンモニアを更に加えて反応させ、タウリンナトリウムを新たに生成するステップとを含むことを特徴とする、タウリンの製造方法。 - 前記ステップ1)において、pH値を調整する前のタウリンナトリウム溶液の質量パーセント濃度が45%〜48%であることを特徴とする、請求項1に記載のタウリンの製造方法。
- 前記ステップ1)において、pH値の調整に用いられる物質がSO2またはH2SO3であることを特徴とする、請求項1に記載のタウリンの製造方法。
- 前記ステップ1)において、SO2を用いてpH値を4.5〜9.0に調整することを特徴とする、請求項1に記載のタウリンの製造方法。
- 前記ステップ1)において、SO2を用いてpH値を5.5〜6.5に調整することを特徴とする、請求項4に記載のタウリンの製造方法。
- 前記ステップ2)において、ヒドロキシエタンスルホン酸ナトリウムの質量パーセント濃度が48%〜55%であることを特徴とする、請求項5に記載のタウリンの製造方法。
- 前記ステップ2)において、70〜80℃のエチレンオキシドを、pH値を調整済みのタウリンナトリウム溶液に導入し、溶液におけるタウリンナトリウムとエチレンオキシドとの物質量の比率が1:1〜1:1.2となるようにすることを特徴とする、請求項1に記載のタウリンの製造方法。
- 前記ステップ4)において、ヒドロキシエタンスルホン酸ナトリウムの反応液にアンモニアを加えた後、アンモニアの体積パーセントが混合液の23%〜26%を占めることを特徴とする、請求項1に記載のタウリンの製造方法。
- 前記タウリンの製造方法は、RNHCH2CH2SO3HとR(R`)NCH2CH2SO3Hの製造に用いられることを特徴とする、請求項1〜8の何れか一項に記載のタウリンの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210416911.3 | 2012-10-25 | ||
CN201210416911.3A CN103382170B (zh) | 2012-10-25 | 2012-10-25 | 一种牛磺酸的制备方法 |
PCT/CN2013/071665 WO2014063456A1 (zh) | 2012-10-25 | 2013-02-19 | 一种牛磺酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015501331A true JP2015501331A (ja) | 2015-01-15 |
JP5850550B2 JP5850550B2 (ja) | 2016-02-03 |
Family
ID=49490127
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014542708A Active JP5850550B2 (ja) | 2012-10-25 | 2013-02-19 | タウリンの製造方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20140121405A1 (ja) |
EP (1) | EP2754652A1 (ja) |
JP (1) | JP5850550B2 (ja) |
CN (1) | CN103382170B (ja) |
WO (1) | WO2014063456A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019513688A (ja) * | 2016-06-28 | 2019-05-30 | 潜江永安薬業股▲分▼有限公司 | タウリン酸の製造方法 |
JP2023095750A (ja) * | 2021-12-24 | 2023-07-06 | チェンジャン ヨンアン ファーマシュティカル カンパニー リミテッド | タウリン母液のリサイクル方法 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104628609A (zh) * | 2013-11-07 | 2015-05-20 | 山东方明药业集团股份有限公司 | 一种牛磺酸的分离提取方法 |
US9428450B2 (en) | 2014-04-18 | 2016-08-30 | Songzhou Hu | Process for producing taurine from alkali taurinates |
US20210179551A1 (en) | 2014-04-18 | 2021-06-17 | Vitaworks Ip, Llc | Process for producing alkali taurinate |
US9593076B2 (en) * | 2014-04-18 | 2017-03-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
USRE48392E1 (en) * | 2014-04-18 | 2021-01-12 | Vitaworks Ip, Llc | Cyclic process for the production of taurine from alkali isethionate |
US9573890B2 (en) | 2014-04-18 | 2017-02-21 | Vitaworks Ip, Llc | Process for producing taurine |
USRE48369E1 (en) * | 2014-04-18 | 2020-12-29 | Vitaworks Ip, Llc | Process for producing taurine |
WO2018026396A1 (en) * | 2016-08-04 | 2018-02-08 | Vitaworks Ip, Llc | Process for producing taurine |
US9428451B2 (en) | 2014-04-18 | 2016-08-30 | Songzhou Hu | Cyclic process for the production of taurine from alkali isethionate |
US9061976B1 (en) * | 2014-05-27 | 2015-06-23 | Songzhou Hu | Cyclic process for the production of taurine from ethylene oxide |
CN104447426B (zh) * | 2014-12-01 | 2016-08-24 | 江苏远洋药业股份有限公司 | 一种牛磺酸母液中提取牛磺酸的方法 |
CN105037217B (zh) * | 2015-06-17 | 2017-04-12 | 南京博炫生物科技有限公司 | 一种生物缓冲剂的制备方法 |
CN104945289A (zh) * | 2015-07-14 | 2015-09-30 | 潜江永安药业股份有限公司 | 一种用固体羟乙基磺酸钠制备牛磺酸的方法 |
US9598357B1 (en) | 2016-02-29 | 2017-03-21 | Vitaworks Ip, Llc | Process for producing taurine from alkali taurinates |
US10683264B2 (en) | 2016-09-16 | 2020-06-16 | Vitaworks Ip, Llc | Process for producing taurine |
US9815778B1 (en) * | 2016-09-16 | 2017-11-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
CN106588704B (zh) * | 2016-11-24 | 2019-03-15 | 黄冈市富驰制药有限责任公司 | 一种制备牛磺酸的方法 |
US9994517B1 (en) | 2016-12-01 | 2018-06-12 | Vitaworks Ip, Llc | Method for preparing taurine |
US9850200B1 (en) | 2016-12-01 | 2017-12-26 | Vitaworks Ip, Llc | Method for preparing taurine |
CN107056659B (zh) * | 2017-06-16 | 2019-06-18 | 潜江永安药业股份有限公司 | 一种高收率循环生产牛磺酸的方法 |
WO2019094051A1 (en) * | 2017-11-13 | 2019-05-16 | Plant Sensory Systems, Llc | Methods for high taurine production using novel decarboxylases |
CN110590614A (zh) * | 2019-08-28 | 2019-12-20 | 王建峰 | 一种牛磺酸的分离纯化工艺 |
CN110483342A (zh) * | 2019-09-02 | 2019-11-22 | 潜江永安药业股份有限公司 | 一种牛磺酸母液除杂回收的方法以及除杂回收系统 |
CN111214843B (zh) * | 2020-03-02 | 2022-04-26 | 黄冈永安日用化工有限公司 | 一种高品质甲基牛磺酸钠的蒸馏装置及生产方法 |
CN113816880B (zh) * | 2020-06-19 | 2023-08-11 | 万华化学集团股份有限公司 | 一种高效合成n-甲基牛磺酸及n-甲基牛磺酸钠的方法 |
CN112592296B (zh) * | 2020-12-21 | 2023-01-20 | 浙江新和成股份有限公司 | 一种连续反应生产羟乙基磺酸钠的方法 |
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US8609890B1 (en) * | 2011-09-06 | 2013-12-17 | Songzhou Hu | Cyclic process for the production of taurine |
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AU2005324199A1 (en) * | 2005-01-05 | 2006-07-13 | Magd Ahmed Kotb Abdalla | Taurine synthesis, production and utility as a medicine |
CN101508658A (zh) * | 2008-02-14 | 2009-08-19 | 王代龙 | 牛磺酸的制备方法 |
-
2012
- 2012-10-25 CN CN201210416911.3A patent/CN103382170B/zh active Active
-
2013
- 2013-02-19 EP EP13719217.5A patent/EP2754652A1/en not_active Withdrawn
- 2013-02-19 US US13/824,402 patent/US20140121405A1/en not_active Abandoned
- 2013-02-19 WO PCT/CN2013/071665 patent/WO2014063456A1/zh active Application Filing
- 2013-02-19 JP JP2014542708A patent/JP5850550B2/ja active Active
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CN101508657A (zh) * | 2008-02-14 | 2009-08-19 | 王代龙 | 牛磺酸的合成方法 |
CN101508659A (zh) * | 2008-02-14 | 2009-08-19 | 王代龙 | 一种制备牛磺酸的方法 |
CN101486669A (zh) * | 2009-01-09 | 2009-07-22 | 沙洋天一药业有限公司 | 一种合成牛磺酸的方法 |
US8609890B1 (en) * | 2011-09-06 | 2013-12-17 | Songzhou Hu | Cyclic process for the production of taurine |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019513688A (ja) * | 2016-06-28 | 2019-05-30 | 潜江永安薬業股▲分▼有限公司 | タウリン酸の製造方法 |
JP2023095750A (ja) * | 2021-12-24 | 2023-07-06 | チェンジャン ヨンアン ファーマシュティカル カンパニー リミテッド | タウリン母液のリサイクル方法 |
JP7503599B2 (ja) | 2021-12-24 | 2024-06-20 | チェンジャン ヨンアン ファーマシュティカル カンパニー リミテッド | タウリン母液を用いてイセチオン酸アルカリ金属塩を製造する方法およびタウリンを製造する方法 |
Also Published As
Publication number | Publication date |
---|---|
JP5850550B2 (ja) | 2016-02-03 |
US20140121405A1 (en) | 2014-05-01 |
EP2754652A1 (en) | 2014-07-16 |
CN103382170B (zh) | 2015-04-08 |
WO2014063456A1 (zh) | 2014-05-01 |
CN103382170A (zh) | 2013-11-06 |
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