JP2019513688A - タウリン酸の製造方法 - Google Patents
タウリン酸の製造方法 Download PDFInfo
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- taurate
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- 239000002253 acid Substances 0.000 title claims description 29
- 229940104261 taurate Drugs 0.000 claims abstract description 39
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims abstract description 39
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000007791 liquid phase Substances 0.000 claims abstract description 19
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 17
- 239000010452 phosphate Substances 0.000 claims abstract description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 13
- 239000007790 solid phase Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 30
- -1 alkali metal salt Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000047 product Substances 0.000 abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 abstract description 3
- 239000000383 hazardous chemical Substances 0.000 abstract description 3
- 125000002091 cationic group Chemical group 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 229940104256 sodium taurate Drugs 0.000 description 11
- GWLWWNLFFNJPDP-UHFFFAOYSA-M sodium;2-aminoethanesulfonate Chemical group [Na+].NCCS([O-])(=O)=O GWLWWNLFFNJPDP-UHFFFAOYSA-M 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical group [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000004255 ion exchange chromatography Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002910 solid waste Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000036592 analgesia 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000004382 visual function Effects 0.000 description 1
- 239000002699 waste material Substances 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
-
- 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
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/08—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(a)系のpHが5.0〜9.5の値になるまでヒドロキシエチルスルホン酸とタウリン酸塩溶液を混合する工程と、
(b)系の液相と固相を分離し、得られた固相はタウリン酸粗製品であり、得られた液相はヒドロキシエチルスルホン酸塩溶液である工程と、
(c)工程(b)で得られた液相にアンモニア水を加えて反応させ、タウリン酸塩溶液を得る工程と、
を含むことを特徴とするタウリン酸の製造方法である。
質量パーセントが46%のタウリン酸ナトリウム水溶液 500mLを反応フラスコに入れて、室温で撹拌しながら、pHが5.5になるまでヒドロキシエチルスルホン酸をゆっくり加えて、系温度を15℃に降温して濾過し、タウリン酸粗製品 216gを得、濾液を反応フラスコに移した後、この濾液に濃度が26.5%のアンモニア水 1710gを追加し、高圧反応釜にて250℃に加熱し、圧力10MPaで1時間反応させ、降温して排出し、蒸発してアンモニアを追い出し、タウリン酸ナトリウム溶液 697gを得た。タウリン酸の含有量はHPLCで測定し、ヒドロキシエチルスルホン酸ナトリウムの含有量はイオンクロマトグラフィーで測定した。結果を表1に示し、表に記載のパーセント含有量はいずれも質量パーセントである。
実施例1で得られたタウリン酸ナトリウム溶液 500mLを反応フラスコに入れて、室温で撹拌しながら、pHが7.5になるまでヒドロキシエチルスルホン酸をゆっくり加えて、系温度を15℃に降温して濾過し、タウリン酸粗製品 229gを得、濾液を反応フラスコに移した後、この濾液に濃度が25.8%のアンモニア水 1700gを追加し、高圧反応釜にて253℃に加熱し、圧力10.5MPaで1時間反応させ、降温して排出し、蒸発してアンモニアを追い出し、タウリン酸ナトリウム溶液 615gを得た。タウリン酸の含有量はHPLCで測定し、ヒドロキシエチルスルホン酸ナトリウムの含有量はイオンクロマトグラフィーで測定した。結果を表2に示し、表に記載のパーセント含有量はいずれも質量パーセントである。
質量パーセントが46%のタウリン酸ナトリウム溶液 500mLを反応フラスコに入れて、室温で撹拌しながら、pHが8.5になるまでヒドロキシエチルスルホン酸をゆっくり加えて、系温度を15℃に降温して濾過し、タウリン酸粗製品 223gを得、濾液を反応フラスコに移した後、この濾液に濃度が26.0%のアンモニア水 1690gを追加し、高圧反応釜にて256℃に加熱し、圧力10.5MPaで1時間反応させ、降温して排出し、蒸発してアンモニアを追い出し、タウリン酸ナトリウム溶液 580gを得た。タウリン酸の含有量はHPLCで測定し、ヒドロキシエチルスルホン酸ナトリウムの含有量はイオンクロマトグラフィーで測定した。結果を表3に示し、表に記載のパーセント含有量はいずれも質量パーセントである。
質量パーセントが46%のタウリン酸ナトリウム溶液 500mlを反応フラスコに入れて、室温で撹拌しながら、pHが9.0になるまでヒドロキシエチルスルホン酸をゆっくり加えて、15℃に降温して濾過し、タウリン酸粗製品 201gを得、濾液を反応フラスコに移した後、この濾液に濃度が25.9%のアンモニア水 1680gを追加し、高圧反応釜にて258℃に加熱し、圧力11MPaで1時間反応させ、降温して排出し、蒸発してアンモニアを追い出し、タウリン酸ナトリウム溶液 585gを得た。タウリン酸の含有量はHPLCで測定し、ヒドロキシエチルスルホン酸ナトリウムの含有量はイオンクロマトグラフィーで測定した。結果を表4に示し、表に記載のパーセント含有量はいずれも質量パーセントである。
実施例2の質量パーセントが46.35%のタウリン酸ナトリウム溶液 600gを反応フラスコに入れて、室温で撹拌しながら、pHが7.8になるまでヒドロキシエチルスルホン酸をゆっくり加えて、15℃に降温して濾過し、タウリン酸粗製品 221gを得、濾液を反応フラスコに移した後、この濾液に濃度が25.9%のアンモニア水 1700gを追加し、高圧反応釜にて258℃に加熱し、圧力11MPaで1.5時間反応させ、降温して排出し、蒸発してアンモニアを追い出し、タウリン酸ナトリウム溶液 605gを得た。タウリン酸の含有量はHPLCで測定し、ヒドロキシエチルスルホン酸ナトリウムの含有量はイオンクロマトグラフィーで測定した。結果を表5に示し、表に記載のパーセント含有量はいずれも質量パーセントである。
Claims (10)
- (a)系のpHが5.0〜9.5の値になるまでヒドロキシエチルスルホン酸とタウリン酸塩溶液を混合する工程と、
(b)系の液相と固相を分離し、得られた固相はタウリン酸粗製品であり、得られた液相はヒドロキシエチルスルホン酸塩溶液である工程と、
(c)工程(b)で得られた液相にアンモニア水を加えて反応させ、タウリン酸塩溶液を得る工程と、
を含むことを特徴とするタウリン酸の製造方法。 - 前記タウリン酸塩は、タウリン酸のアンモニウム塩、タウリン酸のアルカリ金属塩、タウリン酸のアルカリ土類金属塩からなる群より選択される少なくとも1種であることを特徴とする請求項1に記載の方法。
- 工程(a)において、前記タウリン酸塩溶液は、タウリン酸塩の水への溶解及び/又は工程(b)で得られたタウリン酸塩溶液の循環利用に由来することを特徴とする請求項1に記載の方法。
- 工程(a)において、タウリン酸塩溶液の質量パーセント濃度が35%〜60%であることを特徴とする請求項1に記載の方法。
- 工程(a)において、タウリン酸塩溶液の質量パーセント濃度が40%〜50%であることを特徴とする請求項1に記載の方法。
- 工程(a)では、系のpHが5.5〜9.0の値になるまでヒドロキシエチルスルホン酸とタウリン酸塩溶液を混合することを特徴とする請求項1に記載の方法。
- 工程(b)で系の液相と固相を分離する際に、系の温度が0〜50℃であることを特徴とする請求項1に記載の方法。
- 工程(b)で系の液相と固相を分離する際に、系の温度が10〜20℃であることを特徴とする請求項1に記載の方法。
- 前記タウリン酸の製造方法はバッチ式であることを特徴とする請求項1に記載の方法。
- 前記タウリン酸の製造方法は連続式であることを特徴とする請求項1に記載の方法。
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CN201610489140.9 | 2016-06-28 | ||
CN201610489140.9A CN106008280B (zh) | 2016-06-28 | 2016-06-28 | 一种制备牛磺酸的方法 |
PCT/CN2016/088077 WO2018000404A1 (zh) | 2016-06-28 | 2016-07-01 | 一种制备牛磺酸的方法 |
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EP (1) | EP3287439A4 (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US9145359B2 (en) | 2013-12-30 | 2015-09-29 | Songzhou Hu | Cyclic process for the production of taurine from monoethanolamine |
US9428450B2 (en) | 2014-04-18 | 2016-08-30 | Songzhou Hu | Process for producing taurine from alkali taurinates |
US9573890B2 (en) | 2014-04-18 | 2017-02-21 | Vitaworks Ip, Llc | Process for producing taurine |
US20210179551A1 (en) | 2014-04-18 | 2021-06-17 | Vitaworks Ip, Llc | Process for producing alkali taurinate |
USRE48369E1 (en) | 2014-04-18 | 2020-12-29 | Vitaworks Ip, Llc | 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 |
CN106008280B (zh) * | 2016-06-28 | 2018-01-09 | 潜江永安药业股份有限公司 | 一种制备牛磺酸的方法 |
US9815778B1 (en) | 2016-09-16 | 2017-11-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
US9745258B1 (en) | 2016-09-16 | 2017-08-29 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
US10112894B2 (en) | 2016-09-16 | 2018-10-30 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
US10683264B2 (en) | 2016-09-16 | 2020-06-16 | Vitaworks Ip, Llc | Process for producing taurine |
US11161808B1 (en) | 2020-09-09 | 2021-11-02 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
US11578036B2 (en) | 2020-09-09 | 2023-02-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
US11254639B1 (en) | 2020-09-09 | 2022-02-22 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
CN113087645B (zh) * | 2021-03-25 | 2022-10-28 | 湖北远大生命科学与技术有限责任公司 | 制备牛磺酸的系统和方法 |
CN114011367B (zh) * | 2021-11-26 | 2023-07-11 | 王代龙 | 一种2-氨基乙磺酸高效合成反应设备及使用方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8609890B1 (en) * | 2011-09-06 | 2013-12-17 | Songzhou Hu | Cyclic process for the production of taurine |
JP2015501331A (ja) * | 2012-10-25 | 2015-01-15 | キアンジアン ヨンアン ファーマシューティカル カンパニー リミテッドQiangjiang Yongan Pharmaceutical Co., Ltd | タウリンの製造方法 |
US20150210633A1 (en) * | 2014-01-29 | 2015-07-30 | Songzhou Hu | Process for the production of taurine from ethanol |
US20150299113A1 (en) * | 2014-04-18 | 2015-10-22 | Songzhou Hu | Cyclic process for the production of taurine from alkali isethionate and alkali vinyl sulfonate |
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CN106008280B (zh) * | 2016-06-28 | 2018-01-09 | 潜江永安药业股份有限公司 | 一种制备牛磺酸的方法 |
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US8609890B1 (en) * | 2011-09-06 | 2013-12-17 | Songzhou Hu | Cyclic process for the production of taurine |
JP2015501331A (ja) * | 2012-10-25 | 2015-01-15 | キアンジアン ヨンアン ファーマシューティカル カンパニー リミテッドQiangjiang Yongan Pharmaceutical Co., Ltd | タウリンの製造方法 |
US20150210633A1 (en) * | 2014-01-29 | 2015-07-30 | Songzhou Hu | Process for the production of taurine from ethanol |
US20150299113A1 (en) * | 2014-04-18 | 2015-10-22 | Songzhou Hu | Cyclic process for the production of taurine from alkali isethionate and alkali vinyl sulfonate |
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CN106008280A (zh) | 2016-10-12 |
EP3287439A4 (en) | 2018-03-07 |
JP6931284B2 (ja) | 2021-09-01 |
CN106008280B (zh) | 2018-01-09 |
EP3287439A1 (en) | 2018-02-28 |
WO2018000404A1 (zh) | 2018-01-04 |
US20180208553A1 (en) | 2018-07-26 |
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