JPH0366659A - Production of isethionic acid - Google Patents
Production of isethionic acidInfo
- Publication number
- JPH0366659A JPH0366659A JP20122089A JP20122089A JPH0366659A JP H0366659 A JPH0366659 A JP H0366659A JP 20122089 A JP20122089 A JP 20122089A JP 20122089 A JP20122089 A JP 20122089A JP H0366659 A JPH0366659 A JP H0366659A
- Authority
- JP
- Japan
- Prior art keywords
- isethionic acid
- hydrogen chloride
- reaction
- anhydrous
- ethanol
- 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
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 title claims description 39
- 229940045996 isethionic acid Drugs 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- LLOHIFXFHGMBNO-UHFFFAOYSA-N azane;2-hydroxyethanesulfonic acid Chemical compound [NH4+].OCCS([O-])(=O)=O LLOHIFXFHGMBNO-UHFFFAOYSA-N 0.000 claims abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- -1 isethionic anhydride ammonium salt Chemical compound 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- 239000002904 solvent Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940045998 sodium isethionate Drugs 0.000 description 2
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- 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」
本発明は界面活性剤、樹脂或は触媒等の分野に有用な化
合物であるイセチオン酸の改良された製造方法に関する
。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to an improved method for producing isethionic acid, a compound useful in the fields of surfactants, resins, catalysts, and the like.
「従来技術Ｊ
イセチオン酸の製造方法として従来から種々の方法が提
案されているが、製造されたイセチオン酸を容易に単離
できる方法としては、米国特許第４．６９６．７７３号
が既に開示されている。“Prior Art J Various methods have been proposed for producing isethionic acid, but U.S. Pat. No. 4,696,773 has already been disclosed as a method for easily isolating the produced isethionic acid. ing.
上記方法にあっては、確かに品質の良いイセチオン酸を
高収率で得ることができるが、使用される反応溶媒が無
水の低級アルコールであり、この溶媒に対する原料イセ
チオン酸ナトリウムの溶解度が極めて低い。従って無水
塩化水素との反応が実質的に不均一な状態で起こる為か
反応速度が遅くこれを回避するべく反応温度を上げると
、分解等の好ましくない副反応が起こり、その結果得ら
れるイセチオン酸の品質が低下した。In the above method, isethionic acid of good quality can certainly be obtained in high yield, but the reaction solvent used is anhydrous lower alcohol, and the solubility of the raw material sodium isethionate in this solvent is extremely low. . Therefore, perhaps because the reaction with anhydrous hydrogen chloride occurs in a substantially non-uniform state, the reaction rate is slow and when the reaction temperature is raised to avoid this, undesirable side reactions such as decomposition occur, resulting in isethionic acid being obtained. quality has decreased.
「発明が解決しようとする問題点」
上記の如き欠点を解決すべく、本発明者らはイセチオン
酸塩の溶解度、及び酸との反応により得られるイセチオ
ン酸単体の単離の経済性に着目し検討を加えた結果、今
まで顧みられることがなかった、特定のアルコールに対
する溶解度が高いイセチオン酸のアンモニウム塩を用い
れば、高品質のイセチオン酸を工業的に容易に製造出来
ることを見出し、本発明に到達した。"Problems to be Solved by the Invention" In order to solve the above-mentioned drawbacks, the present inventors focused on the solubility of isethionate salts and the economical efficiency of isolation of isethionic acid alone obtained by reaction with acid. As a result of further investigation, it was discovered that high-quality isethionic acid can be easily produced industrially by using an ammonium salt of isethionic acid, which has a high solubility in a specific alcohol, which has not been considered until now. reached.
「問題点を解決する為の手段」
即ち、本発明は炭素数１〜３のアルコールの存在下、無
水イセチオン酸アンモニウム塩と無水塩化水素を反応さ
せることを特徴とするイセチオン酸の製造方法である。"Means for Solving the Problems" That is, the present invention is a method for producing isethionic acid, which is characterized by reacting isethionic anhydride ammonium salt with anhydrous hydrogen chloride in the presence of an alcohol having 1 to 3 carbon atoms. .
本発明方法を実施するに当り１反応溶媒として低級アル
コールが用いられるが、これらの例として、メタノール
、エタノール、ｎ−プロパノール、イソプロパノール等
が挙げられ、これらのアルコールに対するイセチオン酸
アンモニウムの溶解度は同ナトリウム塩のそれに比べて
極めて大である。In carrying out the method of the present invention, lower alcohols are used as a reaction solvent, examples of which include methanol, ethanol, n-propanol, isopropanol, etc., and the solubility of ammonium isethionate in these alcohols is that of sodium chloride. It is extremely large compared to that of salt.
例えば、エタノールに対する室温での溶解度を比べてみ
ると、アンモニウム塩の場合、３重量２であるのに対し
、ナトリウム塩の場合、僅かに０．５％である。For example, when comparing the solubility in ethanol at room temperature, in the case of ammonium salt, it is 3% by weight, while in the case of sodium salt, it is only 0.5%.
このように、溶解度の相違により、無水塩化水素との反
応が均一相で進む割合が一桁大きく、従って該反応が速
く進むだけでなく、反応中に副生成物の生成が抑えられ
、上記単体の分離が容易となる。In this way, due to the difference in solubility, the rate at which the reaction with anhydrous hydrogen chloride proceeds in a homogeneous phase is an order of magnitude higher, and therefore, not only does the reaction proceed faster, but the formation of by-products during the reaction is suppressed, and the above simple substance separation becomes easy.
上記のアルコール溶媒とイセチオン酸アンモニウム塩と
の混合比が反応を迅速に進める上で重要であり、後者の
前者に対する重量比は１０〜６０％が好ましい。６０％
以上の使用量では、イセチオン酸アンモニウム塩の溶解
量が少なくなり好ましくなく、又、１０％以上では徒に
使用する溶媒量が多くなるだけでなく、反応効率が悪く
なり好ましくない。The mixing ratio of the above-mentioned alcohol solvent and isethionic acid ammonium salt is important for speeding up the reaction, and the weight ratio of the latter to the former is preferably 10 to 60%. 60%
If the amount used is above, the amount of dissolved ammonium salt of isethionate will decrease, which is not preferable, and if it exceeds 10%, not only will the amount of solvent used increase unnecessarily, but the reaction efficiency will deteriorate, which is not preferable.
本発明方法にあっては使用するイセチオン酸アンモニウ
ム塩は公知の如何なる方法にて得られたものでも良く、
その製造法の一例として、酸性亜硫酸アンモニウムと酸
化エチレンとの反応により得られる。In the method of the present invention, the ammonium salt of isethionate used may be obtained by any known method,
As an example of its production method, it is obtained by reacting acidic ammonium sulfite with ethylene oxide.
本発明方法の原料となるイセチオン酸アンモニウム塩と
塩化水素は共に無水の状態のものを用いるべきであり、
そうする事によってイセチオン酸単体の純度及び収率を
高めることが出来る。同様に溶媒として用いられるアル
コール類も無水の状態の物が好ましい。Both isethionic acid ammonium salt and hydrogen chloride, which are the raw materials for the method of the present invention, should be used in an anhydrous state.
By doing so, the purity and yield of isethionic acid alone can be increased. Similarly, the alcohol used as a solvent is preferably in an anhydrous state.
更に詳しく説明すると、イセチオン酸アンモニウム塩及
び上記のアルコール類にあっては、含水率が１．０％以
下であることが好ましく、塩化水素にあっては、通常工
業的に入手可能な物で良く、その場合含水率はｔｏｏ
ｐｐｍ以下である。To explain in more detail, the isethionic acid ammonium salt and the above alcohols preferably have a water content of 1.0% or less, and as for hydrogen chloride, normally industrially available products may be used. , in that case the water content is too
ppm or less.
本発明方法を実施するに当っては、原料及び上記の溶媒
であるアルコール類を反応容器に入れる。In carrying out the method of the present invention, the raw materials and the alcohols as the solvents mentioned above are placed in a reaction vessel.
その場合入れる順序には限定はないが、例えば、反応容
器にまず溶媒を入れ、次いでイセチオン酸アンモニウム
塩を加え、所定温度に保ちながら攪拌下に塩化水素を添
加する方法、或は溶媒であるアルコール類中に予め塩化
水素を溶解しておき、そこへイセチオン酸アンモニウム
塩を加えて反応を進める方法等を例示できる。In that case, there is no limit to the order in which the solvent is added, but for example, a method may be used in which the solvent is first added to the reaction vessel, then isethionic acid ammonium salt is added, and hydrogen chloride is added while stirring while keeping the temperature at a predetermined temperature, or alcohol as a solvent is added. Examples include a method in which hydrogen chloride is dissolved in advance in a mixture, and isethionic acid ammonium salt is added thereto to proceed with the reaction.
反応温度は通常室温以上であれば良いが、イセチオン酸
アンモニウム塩あるいはイセチオン酸そのものの分解が
予想される程の高温となると、かえって製品の品質低下
の原因となり、好ましくなく、従って、反応温度は室温
以上８０℃以下が好ましい。Generally, the reaction temperature should be at room temperature or above, but if the temperature is so high that decomposition of isethionic acid ammonium salt or isethionic acid itself is expected, it will cause a decrease in the quality of the product, which is not desirable. Therefore, the reaction temperature should be set at room temperature. The temperature is preferably above 80°C.
本発明方法を実施するに際し、イセチオン酸アンモニウ
ム塩と塩化水素のモル比は等モルで良いが、反応を充分
に進める為には、塩化水素を若干過剰に用いることが好
ましく、その過剰量は５０モルＸ程度であり、これ以上
過剰に用いる必要はない。When carrying out the method of the present invention, the molar ratio of isethionic acid ammonium salt and hydrogen chloride may be equimolar, but in order to proceed with the reaction sufficiently, it is preferable to use a slight excess of hydrogen chloride, and the excess amount is 50% It is about X mol, and there is no need to use it in excess.
以上の条件で反応を進め、完了後、反応系内に固体とし
て存在する塩化アンモニウムを濾別し、更に反応媒体を
又塩化水素を過剰に用いた場合にはこれも蒸留によって
留去させることによって無水の高純度イセチオン酸を得
ることが出来る。この際、イセチオン酸の分解を回避す
るために、蒸留温度は高くとも、反応時と同程度が好ま
しい。The reaction proceeds under the above conditions, and after completion, the ammonium chloride present as a solid in the reaction system is filtered off, and the reaction medium is further removed by distillation if hydrogen chloride is used in excess. Anhydrous and highly pure isethionic acid can be obtained. At this time, in order to avoid decomposition of isethionic acid, the distillation temperature is preferably the same as that during the reaction, even if it is high.
「実施例」
以下に、実施例及び比較例を挙げ更に本発明方法を詳し
く説明する。"Example" The method of the present invention will be explained in detail below with reference to Examples and Comparative Examples.
実施例１
撹拌機、温度計、還流冷却器の付いた反応容器へ３７．
０ｇの乾燥イセチオン酸アンモニウムと１００ｍ１のエ
タノールを仕込んでガス導入部以外は密閉した。その後
、無水塩化水素ガスを予め２０℃に冷却しておいた反応
容器内の混合物へ撹拌しながら平均１４ Ｑ ／Ｈｒの
の速度で導入した。導入した塩化水素量は合計でＩＩ、
４ｇであった。約３０分かけて導入したが、その間導入
は円滑に進んだ。又、反応温度は略５０℃以下に保った
。Example 1 37. Into a reaction vessel equipped with a stirrer, thermometer, and reflux condenser.
0 g of dry ammonium isethionate and 100 ml of ethanol were charged, and everything except the gas inlet was sealed. Thereafter, anhydrous hydrogen chloride gas was introduced into the mixture in the reaction vessel, which had been previously cooled to 20° C., at an average rate of 14 Q/Hr while stirring. The total amount of hydrogen chloride introduced was II,
It was 4g. The installation took about 30 minutes, but it went smoothly during that time. Further, the reaction temperature was maintained at about 50°C or lower.
生成した塩化アンモニウムを濾過、除去した後、エタノ
ール及び過剰の塩化水素を減圧下に蒸溜除去した所、残
留液体としてイセチオン酸が３３ｇ得られた。これを２
５℃迄冷却し、固化させた。収率は仕込んだイセチオン
酸アンモニウム対して１００％であり純度は９９．８％
であった。After filtering and removing the generated ammonium chloride, ethanol and excess hydrogen chloride were removed by distillation under reduced pressure, yielding 33 g of isethionic acid as a residual liquid. This 2
It was cooled to 5°C and solidified. The yield is 100% based on the charged ammonium isethionate, and the purity is 99.8%.
Met.
実施例２
実施例１で用いた装置に乾燥イセチオン酸アンモニウム
３７． Ｏｇとイソプロパノールｌｏｏｍ’Ｑを仕込み
、無水塩化水素１１．５ｇを約４０分掛けて反応容器内
の混合物へ導入した。この間内圧は０．７気圧に、反応
温度は約５０℃以下に保たれた。冷却、濾過及び減圧蒸
溜を行い、３３．２ｇのイセチオン酸を得た。Example 2 The apparatus used in Example 1 was charged with 37% dry ammonium isethionate. Og and isopropanol room'Q were charged, and 11.5 g of anhydrous hydrogen chloride was introduced into the mixture in the reaction vessel over about 40 minutes. During this time, the internal pressure was maintained at 0.7 atm and the reaction temperature was maintained at about 50°C or less. Cooling, filtration and vacuum distillation were performed to obtain 33.2 g of isethionic acid.
収率は１０ｏｚであり、その純度は９９．７％であった
。The yield was 10 oz and the purity was 99.7%.
比較例１
実施例１記載の方法に於いて、イセチオン酸アンモニウ
ムに換えて乾燥イセチオン酸ナトリウム３８．５ｇを用
い、無水塩化水素ガスの導入量を平均して１４ Ｑ ／
Ｈｒで反応を行った所、導入開始後約３０分で導入が滞
り、以後導入速度を７ Ｑ ／Ｈｒに下げ続行した所、
実施例１と同様に円滑に進み、合計で１１．５ｇの無水
塩化水素を導入するのに約７５分を要した。見掛けの収
率は１００％であったが、純度は９９％以下であった。Comparative Example 1 In the method described in Example 1, 38.5 g of dry sodium isethionate was used in place of ammonium isethionate, and the amount of anhydrous hydrogen chloride gas introduced was 14 Q /
When the reaction was carried out at 7 hr, the introduction stalled approximately 30 minutes after the start of introduction, and after that the introduction rate was lowered to 7 Q/hr and continued.
The process proceeded smoothly as in Example 1, and it took about 75 minutes to introduce a total of 11.5 g of anhydrous hydrogen chloride. The apparent yield was 100%, but the purity was less than 99%.
「発明の効果」
本発明方法を用いれば、従来公知の方法に比べ、イセチ
オン酸をより能率よく、より短時間に製造することが出
来る。"Effects of the Invention" By using the method of the present invention, isethionic acid can be produced more efficiently and in a shorter time than conventionally known methods.
Claims (1)
ン酸アンモニウム塩と無水塩化水素を反応させることを
特徴とするイセチオン酸の製造方法。 ２、前記アルコールがエタノール又はイソプロパノール
であり、用いる前記イセチオン酸アンモニウム塩とエタ
ノール又はイソプロパノールの重量比が０．１〜０．６
である特許請求の範囲第１項記載の製造方法。[Scope of Claims] 1. A method for producing isethionic acid, which comprises reacting isethionic anhydride ammonium salt with anhydrous hydrogen chloride in the presence of an alcohol having 1 to 3 carbon atoms. 2. The alcohol is ethanol or isopropanol, and the weight ratio of the isethionic acid ammonium salt to ethanol or isopropanol is 0.1 to 0.6.
The manufacturing method according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20122089A JPH0366659A (en) | 1989-08-04 | 1989-08-04 | Production of isethionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20122089A JPH0366659A (en) | 1989-08-04 | 1989-08-04 | Production of isethionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0366659A true JPH0366659A (en) | 1991-03-22 |
Family
ID=16437333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20122089A Pending JPH0366659A (en) | 1989-08-04 | 1989-08-04 | Production of isethionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0366659A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112159340A (en) * | 2020-10-12 | 2021-01-01 | 黄冈永安药业有限公司 | Preparation method of hydroxyethyl sulfonic acid |
-
1989
- 1989-08-04 JP JP20122089A patent/JPH0366659A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112159340A (en) * | 2020-10-12 | 2021-01-01 | 黄冈永安药业有限公司 | Preparation method of hydroxyethyl sulfonic acid |
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