JPS6383058A - Production of aminoethylsulfonic acid - Google Patents
Production of aminoethylsulfonic acidInfo
- Publication number
- JPS6383058A JPS6383058A JP61225007A JP22500786A JPS6383058A JP S6383058 A JPS6383058 A JP S6383058A JP 61225007 A JP61225007 A JP 61225007A JP 22500786 A JP22500786 A JP 22500786A JP S6383058 A JPS6383058 A JP S6383058A
- Authority
- JP
- Japan
- Prior art keywords
- solution
- sulfonic acid
- inorganic salts
- aminoethyl sulfonic
- reaction solution
- 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.)
- Pending
Links
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims abstract description 24
- 238000000909 electrodialysis Methods 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 235000010265 sodium sulphite Nutrition 0.000 claims abstract description 12
- 239000012528 membrane Substances 0.000 claims abstract description 10
- 239000003011 anion exchange membrane Substances 0.000 claims abstract description 9
- 238000005341 cation exchange Methods 0.000 claims abstract description 9
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000011033 desalting Methods 0.000 claims abstract description 6
- 238000010612 desalination reaction Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 abstract description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 208000010125 myocardial infarction Diseases 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 230000003908 liver function Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RORNWUHWEYNMLS-UHFFFAOYSA-N 2-(2-aminoethylsulfonyl)ethanamine Chemical compound NCCS(=O)(=O)CCN RORNWUHWEYNMLS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 aminoethyl sulfone Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 208000027700 hepatic dysfunction Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、アミノエチルスルホン酸を合成する場合に混
入して来る無機塩類、特に塩化ナトリウム、硫酸ナトリ
ウムなどを効果的に除去し、医薬用として使用できるア
ミノエチルスルホン酸を製造する方法に関するものであ
る。[Detailed Description of the Invention] [Industrial Application Field] The present invention effectively removes inorganic salts, especially sodium chloride, sodium sulfate, etc. that are mixed in when synthesizing aminoethyl sulfonic acid, and makes it suitable for pharmaceutical use. The present invention relates to a method for producing aminoethyl sulfonic acid, which can be used as an aminoethyl sulfonic acid.
アミノエチルスルホン酸は、タウリンとして知られてい
る化合物で、心筋梗塞、動脈硬化、肝典能障害などに対
して、予防および治癒効果を有する。Aminoethyl sulfonic acid is a compound known as taurine, and has preventive and curative effects against myocardial infarction, arteriosclerosis, hepatic dysfunction, etc.
クロルエチルアミン塩酸塩類と亜硫酸ナトリウムとから
アミノエチルスルホン酸を合成した反応液には、塩化ナ
トリウム、硫酸ナトリウムなどの無機塩類が多量台まれ
ていて、この反応液からアミノエチルスルホン酸を晶析
させて単離しても、無機塩類を含まないアミノエチルス
ルホン酸を効率よく得ることは困難である。そこで、上
記反応液から無機塩類を除去することにより無機塩類を
含まないアミノエチルスルホン酸を得る方法として、電
気Ｇ析による方法が案出され、それは特顎昭５９−１６
４８９３に記載されている。The reaction solution used to synthesize aminoethyl sulfonic acid from chloroethylamine hydrochloride and sodium sulfite contains a large amount of inorganic salts such as sodium chloride and sodium sulfate, and aminoethyl sulfonic acid is crystallized from this reaction solution. Even if isolated, it is difficult to efficiently obtain aminoethylsulfonic acid that does not contain inorganic salts. Therefore, as a method for obtaining aminoethyl sulfonic acid free of inorganic salts by removing inorganic salts from the above reaction solution, a method using electrolytic G deposition was devised.
4893.
上記従来技術の電気遇析法はかなりの量のアミノエチル
スルホン酸が？Ｍ縮液側に透過して流出するという欠点
がある。Does the conventional electrolytic precipitation method described above produce a considerable amount of aminoethyl sulfonic acid? There is a drawback that it permeates and flows out to the M condensate side.
〔問題点を解決するための手段及び作用〕本発明者らは
、上記問題点を解決するため鋭意検討した結果、２段電
気透析法を採用することにより高収率で目的生成物が得
られることを見出し本発明を完成させるに至つた。[Means and effects for solving the problems] As a result of intensive studies to solve the above problems, the present inventors found that the desired product can be obtained in high yield by adopting a two-stage electrodialysis method. This discovery led to the completion of the present invention.
即ち、本発明はクロルエチルアミン塩酸塩と亜硫酸ナト
リウムとを反応させて得られるアミノエチルスルホン酸
を含有する反応ン皮を、陽イオン交換膜と陰イオン交換
膜とを交互に設置した第一電気透析装置にかけ、無機塩
類を除去した第一脱塩液と無機塩類を蓄積させた第一濃
縮液とに分けて流出させた後、第一脱塩液からアミノエ
チルスルホン酸を単離するとともに、第一濃縮液を前記
第一電気透析装置と同様の第二電気透析装置にかけ、第
二脱塩液と第二濃ｍ液とに分けて流出させた後、第二脱
塩液をアミノエチルスルホン酸の合成系および／又は電
気透析系ヘリサイクルして流出したアミノエチルスルホ
ン酸を回収する方法である。That is, the present invention provides a first electrodialysis method in which a reaction membrane containing aminoethyl sulfonic acid obtained by reacting chloroethylamine hydrochloride and sodium sulfite is provided with alternating cation exchange membranes and anion exchange membranes. After the first desalination liquid, which has removed inorganic salts, and the first concentrated liquid, which has accumulated inorganic salts, are separated and flowed out, aminoethylsulfonic acid is isolated from the first desalination liquid, and the first desalination liquid is separated from the first desalination liquid. The first concentrated solution is applied to a second electrodialysis device similar to the first electrodialysis device, and the second desalted solution and the second concentrated solution are separated and flowed out. This is a method in which the aminoethylsulfonic acid that flows out is recovered by recycling it to the synthesis system and/or electrodialysis system.
本発明で用いる電気透析装置は、通常用いられるもので
、陽イオン交換膜と陰イオン交換膜とを交互に多数配列
し、両端の１対の電橋を配置するものである。陽極側に
陰イオン交換膜、陰極側に陽イオン交換膜のある室では
、電離した陽イオンが陰極に向かって移動し、陽イオン
交換膜を透過して隣室に至り、次の陰イオン交換膜で透
過を阻止される。一方、陰イオンは反対に陽極に向かっ
て移動し陰イオン交換膜を透過して隣室に至り、次の陽
イオン交換膜で阻止される。したがって、１室おきに陽
イオンと陰イオンとが蓄積する室と両イオンが除去され
る室ができることになり、結果として濃縮が行われる室
と脱塩が行われる室とが構成されることになる。これが
本発明で使用する電気透析装置の作用機構である。脱塩
が行われる室から流出するのが脱塩液であり、／Ｍ縮が
行われる室から流出する液が濃縮液である０本発明で使
用するイオン交換層は通常使用されているものでもよ（
、例えば、陽イオン交換膜としてはネオセプタ側−■
（徳山曹達■社製品）、陰イオン交換膜としてはネオセ
プタＡＣＳ （徳山曹達（）菊社製品）などでよい。ま
た、電極液としては硫酸ナトリウム水溶液がよく、これ
を酸性に保つために硫酸を添加してｐＨを２〜５に調整
するのがよい。The electrodialysis apparatus used in the present invention is a commonly used one in which a large number of cation exchange membranes and anion exchange membranes are arranged alternately, and a pair of electric bridges are arranged at both ends. In a chamber with an anion exchange membrane on the anode side and a cation exchange membrane on the cathode side, ionized cations move toward the cathode, pass through the cation exchange membrane, reach the next chamber, and pass through the next anion exchange membrane. The transmission is blocked. On the other hand, anions move toward the anode, pass through the anion exchange membrane, reach the next chamber, and are blocked by the next cation exchange membrane. Therefore, every other chamber has a chamber where cations and anions accumulate and a chamber where both ions are removed, resulting in a chamber where concentration is performed and a chamber where desalination is performed. Become. This is the working mechanism of the electrodialysis device used in the present invention. The desalting solution flows out from the chamber where desalination is performed, and the solution flowing out from the chamber where condensation is performed is a concentrated solution. Yo(
For example, as a cation exchange membrane, Neoceptor side -■
(Tokuyama Soda ■ company product), Neocepta ACS (Tokuyama Soda () Kikusha product) etc. may be used as the anion exchange membrane. The electrode solution is preferably an aqueous sodium sulfate solution, and in order to keep it acidic, sulfuric acid is preferably added to adjust the pH to 2 to 5.
電気透析装置にかける反応液の１度及び温度は特に制限
はないが、電気透析中にアミノエチルスルホン酸の結晶
が透析槽内で析出しないように反応液の１度及び温度を
保つことが必要である０反応液中に含まれる無機塩類の
量にもよるが、ｉ３！７ｒ後のアミノエチルスルホン酸
の濃度が１８％の反応液でも充分処理することが可能で
ある。There are no particular restrictions on the degree and temperature of the reaction solution applied to the electrodialyzer, but it is necessary to maintain the temperature and degree of the reaction solution to prevent crystals of aminoethyl sulfonic acid from precipitating in the dialysis tank during electrodialysis. Although it depends on the amount of inorganic salts contained in the reaction solution, even a reaction solution with an aminoethyl sulfonic acid concentration of 18% after i3!7r can be sufficiently treated.
本発明では、第一電気透析装置より流出する第一脱塩ｌ
ｌ！及び第一７ａｉｔｌ液のうち、第一脱塩液を冷却し
て７ミノエチルスルホン酸の結晶を析出させたのち、常
法により濾過、乾燥して、無機塩類を含まないアミノエ
チルスルホン酸の結晶を得、また第一ｌ眉縮）夜は第二
電気透析装置にかけて脱塩１縮処理を行い、脱塩された
第二脱塩液をアミノエチルスルホン酸の合成系および／
又は電気透析系へ再循環して、ここに含まれるアミノエ
チルスルホン酸を回収する。上記の第二ｔ７４ ｍ ？
ｆＸは系外へ放出する。In the present invention, the first desalination l flowing out from the first electrodialyzer is
l! Of the first 7aitl solution, the first desalted solution is cooled to precipitate crystals of 7-aminoethylsulfonic acid, and then filtered and dried by a conventional method to obtain crystals of aminoethylsulfonic acid that do not contain inorganic salts. At night, the second desalted solution was subjected to a desalination treatment using a second electrodialysis device, and the second desalted solution was transferred to an aminoethyl sulfonic acid synthesis system and/or
Alternatively, the aminoethyl sulfonic acid contained therein can be recovered by recycling to the electrodialysis system. Second t74 m above?
fX is released outside the system.
以下、実施例により本発明を更に具体的に説明する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
アミノエチルスルホンＭ５７８ｇ、塩化ナトリウふ５６
８ ｇ 、亜硫酸ナトリウム５６ｇ、硫酸ナトリウム４
２ｇ及び水３０００ ｇより成るアミノエチルスルホン
酸を含有する反応液４２４４ ｇに水９（１０ｇを加え
て、電気透析装置にかける溶液に調整した。また、塩化
ナトリウム１６６ ｇおよび水１９５０ ｇよりなる食
塩水を調整した。これらの溶液を陽イオン交換膜がネオ
セプタＣＭ−■あり、陰イオン交換膜がネオセプタＡＣ
Ｓである第一電気透析装置にかけ、電極液として硫酸ナ
トリウム水溶液を用い、液温５０℃で第一電気透析処理
を行いアミノエチルスルホン酸５２２ｇ、塩化ナトリウ
ム８ｇ、亜硫酸ナトリウム２８ｇ、硫酸ナトリウム１６
ｇ及び水２３０４ ｇより成る第一脱塩液２８７ｇ並び
にアミノエチルスルホン！５６ｇ、塩化ナトリウム７２
６ｇ、亜硫酸ナトリウム２８ｇ、硫酸ナトリウム２６ｇ
及び水３５４６ ｇより成る第一濃縮液４３８２ ｇを
得た。第一脱塩液は冷却してアミノエチルスルホン酸の
結晶を析出させたのち、これを濾過し、次いで水３９０
ｇでリンスし乾燥して、無機塩類を含まないアミノエ
チルスルホン酸の結晶４０２ｇを得た。アミノエチルス
ルホン酸１２０ｇ、塩化ナトリウム８ｇ１亜硫酸ナトリ
ウム２８ｇ、硫酸ナトリウム１６ｇ及び水２６９４ ｇ
より成る濾液は、後述の第二脱塩液と一緒にして、アミ
ノエチルスルホン酸の合成系および／又は透析系へ再循
環する。Example 1 Aminoethyl sulfone M578g, sodium chloride 56g
8 g, sodium sulfite 56 g, sodium sulfate 4
9 (10 g) of water was added to 4,244 g of a reaction solution containing aminoethyl sulfonic acid, consisting of 2 g of aminoethyl sulfonic acid and 3,000 g of water, to prepare a solution to be applied to an electrodialyzer. The water was adjusted.The cation exchange membrane was Neocepta CM-■, and the anion exchange membrane was Neoceptor AC.
Using a sodium sulfate aqueous solution as an electrode solution, the first electrodialysis treatment was carried out at a temperature of 50° C. to obtain 522 g of aminoethyl sulfonic acid, 8 g of sodium chloride, 28 g of sodium sulfite, and 16 g of sodium sulfate.
g and 287 g of the first desalination solution consisting of 2304 g of water and aminoethyl sulfone! 56g, sodium chloride 72
6g, sodium sulfite 28g, sodium sulfate 26g
4382 g of a first concentrate consisting of 3546 g of water and 3546 g of water was obtained. The first desalination solution was cooled to precipitate crystals of aminoethylsulfonic acid, and then filtered, followed by water 390%
The resulting product was rinsed with water and dried to obtain 402 g of aminoethyl sulfonic acid crystals containing no inorganic salts. 120 g of aminoethyl sulfonic acid, 8 g of sodium chloride, 28 g of sodium sulfite, 16 g of sodium sulfate and 2694 g of water.
The filtrate is recycled to the aminoethylsulfonic acid synthesis system and/or dialysis system together with the second desalting solution described below.
第一濃縮液と塩化ナトリウム１６６ｇおよび水３７８４
ｇよりなる食塩水とは第一電気透析装置と同様の第二
電気透析装置にかけて、第一電気透析袋Ｉと同様の条件
で透析を行い、アミノエチルスルホン１９５０ ｇ、塩
化ナトリウム８ｇ、亜硫酸ナトリウム１４ｇ、硫酸ナト
リウム［Ｏｇ及び水２１２８ｇより成る第二脱塩’１５
２２１０ｇ並びにアミノエチルスルホンＨ６ｇ、塩化ナ
トリウム８８４ｇ、亜硫酸ナトリウム１４ｇ、６ｆｉ酸
ナトナトリウム１６び水５２０２ ｇより成る第二？７
Ａ縮液６１２２ ｇを得た。第二脱塩液は前述の濾液と
一諸にしてアミノエチルスルホン酸の合成系又は透析系
へ再循環してアミノエチルスルホン酸を回収する。First concentrate, 166g of sodium chloride and 3784g of water
A saline solution consisting of 1,950 g of aminoethyl sulfone, 8 g of sodium chloride, and 14 g of sodium sulfite was obtained by dialyzing it in a second electrodialysis device similar to the first electrodialysis device under the same conditions as the first electrodialysis bag I. , 2nd desalination '15 consisting of sodium sulfate [Og and 2128 g of water.
2210 g, as well as 6 g of aminoethyl sulfone H, 884 g of sodium chloride, 14 g of sodium sulfite, 16 g of sodium 6fiate, and 5202 g of water. 7
6122 g of condensate A was obtained. The second desalted solution is combined with the above-mentioned filtrate and recycled to the aminoethylsulfonic acid synthesis system or dialysis system to recover aminoethylsulfonic acid.
本発明の方法より、クロルエチルアミン塩酸塩と亜硫酸
ナトリウムとからアミノエチルスルホン酸を合成した反
応液を処理して、無機塩類を含まないアミノエチルスル
ホン酸を効率よ（得ることができる。According to the method of the present invention, aminoethyl sulfonic acid containing no inorganic salts can be efficiently obtained by treating a reaction solution in which aminoethyl sulfonic acid is synthesized from chloroethylamine hydrochloride and sodium sulfite.
Claims (1)
を反応させて得られるアミノエチルスルホン酸を含有す
る反応液を、陽イオン交換膜と陰イオン交換膜とを交互
に設定した第一電気透析装置にかけ、無機塩類を除去し
た第一脱塩液と無機塩類を蓄積させた第一濃縮液とに分
けて流出させた後、第一脱塩液からアミノエチルスルホ
ン酸を単離するとともに、第一濃縮液を前記第一電気透
析装置と同様の第二電気透析装置にかけ、第二脱塩液と
第二濃縮液とに分けて流出させた後、第二脱塩液をアミ
ノエチルスルホン酸の合成系および／又は電気透析系へ
リサイクルすることを特徴とするアミノエチルスルホン
酸の製造方法。(1) A reaction solution containing aminoethyl sulfonic acid obtained by reacting chloroethylamine hydrochloride and sodium sulfite is applied to a first electrodialysis device in which a cation exchange membrane and an anion exchange membrane are alternately set, After separating the first desalting liquid from which inorganic salts have been removed and the first concentrated liquid from which inorganic salts have been accumulated, the aminoethyl sulfonic acid is isolated from the first desalting liquid, and the first concentrated liquid is separated from the first desalting liquid. is applied to a second electrodialysis device similar to the first electrodialysis device, and the second desalination solution and the second concentrated solution are separated and flowed out. A method for producing aminoethyl sulfonic acid, which comprises recycling the aminoethyl sulfonic acid to/or an electrodialysis system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61225007A JPS6383058A (en) | 1986-09-25 | 1986-09-25 | Production of aminoethylsulfonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61225007A JPS6383058A (en) | 1986-09-25 | 1986-09-25 | Production of aminoethylsulfonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6383058A true JPS6383058A (en) | 1988-04-13 |
Family
ID=16822617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61225007A Pending JPS6383058A (en) | 1986-09-25 | 1986-09-25 | Production of aminoethylsulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6383058A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380064A (en) * | 1992-11-30 | 1995-01-10 | Ikeda Bussan Co., Ltd. | Rotatable seat |
| US5810441A (en) * | 1996-06-14 | 1998-09-22 | Ikeda Bussan Co., Ltd. | Rotating device of automotive seat |
| FR2769625A1 (en) * | 1997-10-15 | 1999-04-16 | Atochem Elf Sa | A new method for the elimination of salts from aqueous sufonamide solutions |
| CN106349123A (en) * | 2016-08-25 | 2017-01-25 | 江苏德玛膜科技有限公司 | Method for separating taurine in taurine crude product mother solution |
| CN109134317A (en) * | 2018-09-10 | 2019-01-04 | 合肥科佳高分子材料科技有限公司 | A kind of method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid |
-
1986
- 1986-09-25 JP JP61225007A patent/JPS6383058A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380064A (en) * | 1992-11-30 | 1995-01-10 | Ikeda Bussan Co., Ltd. | Rotatable seat |
| US5810441A (en) * | 1996-06-14 | 1998-09-22 | Ikeda Bussan Co., Ltd. | Rotating device of automotive seat |
| FR2769625A1 (en) * | 1997-10-15 | 1999-04-16 | Atochem Elf Sa | A new method for the elimination of salts from aqueous sufonamide solutions |
| EP0913391A1 (en) * | 1997-10-15 | 1999-05-06 | Elf Atochem S.A. | Desalination of aqueous sulfonamide solutions |
| US6036830A (en) * | 1997-10-15 | 2000-03-14 | Elf Atochem S.A. | Desalination of aqueous sulphonamide solutions |
| CN106349123A (en) * | 2016-08-25 | 2017-01-25 | 江苏德玛膜科技有限公司 | Method for separating taurine in taurine crude product mother solution |
| CN109134317A (en) * | 2018-09-10 | 2019-01-04 | 合肥科佳高分子材料科技有限公司 | A kind of method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid |
| CN109134317B (en) * | 2018-09-10 | 2021-11-12 | 合肥科佳高分子材料科技有限公司 | Method for preparing L-10-camphorsulfonic acid by bipolar membrane electrodialysis |
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