JPH07101932A - Production of organic solution of acrylamidoalkanesulfonic acid metal salt - Google Patents
Production of organic solution of acrylamidoalkanesulfonic acid metal saltInfo
- Publication number
- JPH07101932A JPH07101932A JP27496993A JP27496993A JPH07101932A JP H07101932 A JPH07101932 A JP H07101932A JP 27496993 A JP27496993 A JP 27496993A JP 27496993 A JP27496993 A JP 27496993A JP H07101932 A JPH07101932 A JP H07101932A
- Authority
- JP
- Japan
- Prior art keywords
- metal salt
- acid
- acid metal
- acrylamidoalkanesulfonic
- reaction
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はアクリルアミドアルカン
スルホン酸の中和方法に関する。特に反応速度が速くか
つ高濃度かつ濾過性良好なアクリルアミドアルカンスル
ホン酸金属塩有機溶液の製造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for neutralizing acrylamidoalkanesulfonic acid. In particular, the present invention relates to a method for producing an organic solution of an acrylamidoalkanesulfonic acid metal salt organic solution having a high reaction rate, a high concentration, and good filterability.
【０００２】[0002]
【従来の技術】アクリルアミドアルカンスルホン酸を金
属塩に中和する製造方法は、既に特公昭６２−２８７７
９号公報に記載されている。即ち、アクリルアミドアル
カンスルホン酸と弱酸金属塩、例えば炭酸、酢酸のアル
カリ金属塩、特にナトリウム塩を反応させて中和する。2. Description of the Related Art A method for neutralizing acrylamidoalkanesulfonic acid into a metal salt has already been disclosed in JP-B-62-2877.
No. 9 publication. That is, acrylamide alkanesulfonic acid is reacted with a weak acid metal salt, for example, an alkali metal salt of carbonic acid or acetic acid, particularly a sodium salt, to neutralize.
【０００３】アクリルアミドアルカンスルホン酸は高温
になると自己重合をしやすいので重合禁止剤、例えば大
気中の酸素を利用しつつ、低温に維持し中和させる。ま
た中和反応に伴い、水が生成する。生成する水の量は弱
酸金属塩に炭酸塩を用いると得られる塩の１モルに対
し、水１／２モルである。弱酸金属塩に炭酸水素塩を用
いると得られる塩の１モルに対し、水１モルが生成す
る。従って、弱酸金属塩としては炭酸塩の方が炭酸水素
塩より好ましいと記載されている。[0003] Acrylamide alkane sulfonic acid easily undergoes self-polymerization at high temperatures, so that it is maintained at a low temperature and neutralized while utilizing a polymerization inhibitor, for example, oxygen in the atmosphere. Further, water is produced along with the neutralization reaction. The amount of water produced is 1/2 mol of water based on 1 mol of the salt obtained by using a carbonate as the weak acid metal salt. When hydrogen carbonate is used as the weak acid metal salt, 1 mol of water is produced for 1 mol of the salt obtained. Therefore, it is described that the carbonate is preferred as the weak acid metal salt over the hydrogen carbonate.
【０００４】しかし、この方法ではアクリルアミドアル
カンスルホン酸金属塩有機溶液の濃度は高々１５重量％
に過ぎない。高濃度になるとアクリルアミドアルカンス
ルホン酸金属塩が析出する。酸性サイドでは自己重合を
起こしやすいので中和反応に際し、弱酸金属塩を少量過
剰に仕込み、反応後濾別するが、弱酸金属塩とアクリル
アミドアルカンスルホン酸金属塩を分離回収できない。
また、工業的に利用する際に濃度が低いと製造設備が大
きくなるため設備投資が高価になり、コストアップとな
る。また、低濃度になれば仕掛かり品在庫が多くなりコ
ストアップとなる。However, according to this method, the concentration of the organic solution of the metal salt of acrylamidoalkanesulfonic acid is at most 15% by weight.
Nothing more than. When the concentration becomes high, acrylamidoalkanesulfonic acid metal salt is precipitated. On the acidic side, self-polymerization is likely to occur, so a small amount of a weak acid metal salt is charged during the neutralization reaction and the mixture is filtered after the reaction, but the weak acid metal salt and the acrylamidoalkanesulfonic acid metal salt cannot be separated and recovered.
In addition, if the concentration is low when used industrially, the manufacturing equipment becomes large and the equipment investment becomes expensive, resulting in an increase in cost. Further, if the concentration becomes low, the inventory of work-in-process will increase and the cost will increase.
【０００５】[0005]
【発明が解決しようとする課題】本発明の目的はアクリ
ルアミドアルカンスルホン酸の中和に際し、反応速度が
速くかつ高濃度有機溶媒溶液を容易に製造する方法を提
供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for easily producing a high-concentration organic solvent solution which has a high reaction rate when neutralizing acrylamidoalkanesulfonic acid.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、アクリル
アミドアルカンスルホン酸金属塩の有機溶液中での溶解
度を向上させる方法を研究し本発明の完成に至った。即
ち、本発明は、アクリルアミドアルカンスルホン酸を予
め溶解した弱酸金属塩又は水酸化ナトリウムの水溶液中
で中和反応させた後、有機溶媒を加えることを特徴とす
るアクリルアミドアルカンスルホン酸金属塩の有機溶液
の製造方法である。The present inventors have studied the method of improving the solubility of acrylamide alkane sulfonic acid metal salt in an organic solution and completed the present invention. That is, the present invention is characterized by adding an organic solvent after a neutralization reaction in an aqueous solution of a weak acid metal salt or sodium hydroxide in which acrylamidoalkanesulfonic acid is previously dissolved, and then adding an organic solvent. Is a manufacturing method.
【０００７】本発明に用いるアクリルアミドアルカンス
ルホン酸は２−アクリルアミド−２−エタンスルホン
酸、２−アクリルアミド−２−メチルプロパンスルホン
酸、２−アクリルアミド−２−メチルブタンスルホン酸
等がある。中でも工業的に多く用いられ、安価である２
−アクリルアミド−２−メチルプロパンスルホン酸が好
ましい。The acrylamidoalkanesulfonic acid used in the present invention includes 2-acrylamido-2-ethanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid and 2-acrylamido-2-methylbutanesulfonic acid. Above all, it is used industrially and is inexpensive 2.
-Acrylamido-2-methylpropanesulfonic acid is preferred.
【０００８】本発明に用いる弱酸金属塩は主にアルカリ
金属塩であり、中ではナトリウム塩が安価であり、多く
用いられる。また炭酸金属塩、または炭酸水素金属塩で
もよく、これらの混合物であっても、どちらでもよい。The weak acid metal salt used in the present invention is mainly an alkali metal salt, of which the sodium salt is inexpensive and is often used. Further, it may be a metal carbonate or a hydrogen carbonate, or a mixture thereof or either.
【０００９】本発明では水溶液中で中和するため、弱酸
金属塩を予め水溶液にし、中和を行うことができる。従
来の弱酸金属塩を分散させた状態で、不均一反応させる
と反応速度は、固体の溶解速度に律速なため十分な時間
が必要であり、反応を制御することが難しい。しかし、
水溶液の形であれば反応速度が速く、反応の制御が可能
となる。本発明では弱酸金属塩と水酸化ナトリウムを併
用して用いることもできる。In the present invention, since the neutralization is carried out in an aqueous solution, the weak acid metal salt can be previously made into an aqueous solution for neutralization. When a conventional weakly acid metal salt is dispersed in a heterogeneous reaction, the reaction rate is rate-determined by the solid dissolution rate, so that a sufficient time is required and it is difficult to control the reaction. But,
If it is in the form of an aqueous solution, the reaction rate is fast and the reaction can be controlled. In the present invention, a weak acid metal salt and sodium hydroxide may be used in combination.
【００１０】水酸化ナトリウムのみを用いる場合は当量
用いるようにする。弱酸金属塩を用いる場合は若干当量
より多めに加えるとよい。水酸化ナトリウムを弱酸金属
塩と併用する場合は、弱酸金属塩のみの場合より過剰量
は少なくてよい。過剰量が少なくなれば濾別が軽減され
る。When using only sodium hydroxide, an equivalent amount is used. When a weak acid metal salt is used, it may be added in a slightly larger amount than the equivalent amount. When sodium hydroxide is used in combination with a weak acid metal salt, the excess amount may be smaller than when only weak acid metal salt is used. When the excess amount is small, filtration is reduced.
【００１１】本発明に用いる有機溶媒は例えばジメチル
ホルムアミド、ジメチルスルホキシド、ジメチルアセト
アミド等がある。中でも価格の安いジメチルホルムアミ
ドが好ましい。The organic solvent used in the present invention includes, for example, dimethylformamide, dimethylsulfoxide, dimethylacetamide and the like. Of these, dimethylformamide, which is inexpensive, is preferable.
【００１２】反応中のアクリルアミドアルカンスルホン
酸の自己重合を防止するため重合禁止剤を添加すること
はよい。重合禁止剤としてはヒドロキシモノメチルエー
テル、ｔ−ブチルカテコール、酸素等がある。A polymerization inhibitor may be added in order to prevent self-polymerization of the acrylamidoalkanesulfonic acid during the reaction. Examples of the polymerization inhibitor include hydroxymonomethyl ether, t-butylcatechol, oxygen and the like.
【００１３】反応温度は４０℃以下、好ましくは３０℃
以下に保持する。反応の終了はｐＨメーターで測定でき
る。予め用いる溶媒のｐＨを測定しておくとよい。有機
溶媒は含水量によりｐＨメーターが異なった値を示すの
で注意を要する。The reaction temperature is 40 ° C. or lower, preferably 30 ° C.
Keep below. The end of the reaction can be measured with a pH meter. It is advisable to measure the pH of the solvent used in advance. Care must be taken because the pH meter of the organic solvent shows different values depending on the water content.
【００１４】アクリルアミドアルカンスルホン酸と弱酸
金属塩、または水酸化ナトリウムの投入順序は、弱酸金
属塩または水酸化ナトリウムを予め水に溶解させ、アク
リルアミドアルカンスルホン酸を投入する。The order of introducing the acrylamidoalkanesulfonic acid and the weak acid metal salt or sodium hydroxide is to dissolve the weak acid metal salt or sodium hydroxide in water in advance and then add the acrylamidoalkanesulfonic acid.
【００１５】[0015]
【発明の効果】本発明のアクリルアミドアルカンスルホ
ン酸金属塩の有機溶液の製造方法によれば、アクリルア
ミドアルカンスルホン酸金属塩の濃度を２５重量％以上
に上げられる。濃度が向上することにより、反応槽、付
帯設備の大きさを小さくでき、設備投資が少なくて済
む。また溶媒等の仕掛かりが少なくて済み、コストダウ
ンができる。アクリロニトリル（ＡＮ）の有機溶媒水溶
液中での重合にそのまま使用することができ好適であ
る。EFFECTS OF THE INVENTION According to the method for producing an organic solution of a metal salt of acrylamide alkane sulfonic acid of the present invention, the concentration of the metal salt of acrylamide alkane sulfonic acid can be increased to 25% by weight or more. By increasing the concentration, the size of the reaction tank and incidental equipment can be reduced, and the equipment investment can be reduced. Further, the amount of solvent and the like required is small, and the cost can be reduced. It is suitable because it can be used as it is for polymerization of acrylonitrile (AN) in an aqueous solution of an organic solvent.
【００１６】[0016]
【実施例】以下、さらに詳細には実施例にて説明する。
実施例中、特に断わらない限り「％」は「重量％」とす
る。アクリルアミドアルカンスルホン酸の有機溶液の定
量は、ヨウドの付加量にて測定した。EXAMPLES The present invention will be described in more detail below with reference to examples.
In the examples, "%" is "% by weight" unless otherwise specified. The quantification of the organic solution of acrylamide alkane sulfonic acid was measured by the amount of iodine added.
【００１７】実施例１ 火気中に開放した反応槽を用い、水７５ｇｒに無水炭酸
ナトリウムを１９．２ｇｒ予め溶解させ、次に２−アク
リルアミド−２−メチルプロパンスルホン酸を徐々に７
５ｇｒ投入しながらよく撹拌し、２−アクリルアミド−
２−メチルプロパンスルホン酸ナトリウム塩を製造し、
中和後にジメチルホルムアミド１５０ｇｒを加える。反
応系は２０℃に維持した。ｐＨが８になった時点を反応
終点とした。反応時間は２０分であった。この溶液の２
−アクリルアミド−２−メチルプロパンスルホン酸ナト
リウム塩の濃度は２５．３６％、水分は２４．７７％で
あった。次いでＡＮ９１．１５％、ＭＡ８．０％、上記
アクリルアミドアルカンスルホン酸ナトリウム塩有機溶
液０．８５％を重量部加えて定法に従い、アクリル系重
合体のドープを得、次いで湿式紡糸をしてアクリル繊維
を製造した。Example 1 Using a reaction vessel opened to the fire, 19.2 gr of anhydrous sodium carbonate was pre-dissolved in 75 gr of water, and then 2-acrylamido-2-methylpropanesulfonic acid was gradually added to 7 gr.
While adding 5 gr, stir well, 2-acrylamide-
Producing 2-methylpropanesulfonic acid sodium salt,
After neutralization, 150 gr of dimethylformamide are added. The reaction system was maintained at 20 ° C. The time point when the pH reached 8 was taken as the end point of the reaction. The reaction time was 20 minutes. 2 of this solution
-The concentration of acrylamido-2-methylpropanesulfonic acid sodium salt was 25.36%, and the water content was 24.77%. Then, 91.15% of AN, 8.0% of MA, and 0.85% of an organic solution of sodium acrylamidoalkanesulfonate are added in a weight ratio to obtain an acrylic polymer dope according to a standard method, and then wet spinning is performed to obtain acrylic fibers. Manufactured.
【００１８】比較例１ 実施例１の反応槽を用い、ジメチルホルムアミド１３３
ｇｒに無水炭酸ナトリウムを１１．４ｇｒ加え、よく撹
拌し、次に２−アクリルアミド−２−メチルプロパンス
ルホン酸を徐々に４４．３６ｇｒ投入しながらよく撹拌
し、２−アクリルアミド−２−メチルプロパンスルホン
酸ナトリウム塩を製造した。反応系は２０℃に維持し
た。ｐＨが９になった時点を反応終点とした。この溶液
の２−アクリルアミド−２−メチルプロパンスルホン酸
ナトリウム塩の濃度は１５．０％であった。反応時間は
１２０分で遅いことが判る。Comparative Example 1 Using the reaction vessel of Example 1, dimethylformamide 133 was used.
To the gr, 11.4 gr of anhydrous sodium carbonate was added and well stirred, and then 2-acrylamido-2-methylpropanesulfonic acid was slowly stirred while adding 44.36 gr of 2-acrylamido-2-methylpropanesulfonic acid. The sodium salt was prepared. The reaction system was maintained at 20 ° C. The time point when the pH reached 9 was taken as the end point of the reaction. The concentration of 2-acrylamido-2-methylpropanesulfonic acid sodium salt in this solution was 15.0%. It can be seen that the reaction time is 120 minutes and is slow.
【００１９】実施例２ 実施例１と同様に水酸化ナトリム１４．５ｇｒを用いて
２−アクリルアミド−２−メチルプロパン酸ナトリウム
塩溶塩を製造した。反応時間は２０分であった。この溶
液の２−アクリルアミド−２−メチルプロパンスルホン
酸ナトリウム塩の濃度は２６．６９％、水分は２５．８
２％であった。Example 2 In the same manner as in Example 1, 14.5 gr of sodium hydroxide was used to produce a sodium salt of 2-acrylamido-2-methylpropanoate. The reaction time was 20 minutes. The concentration of 2-acrylamido-2-methylpropanesulfonic acid sodium salt in this solution is 26.69%, and the water content is 25.8.
It was 2%.
Claims (3)
め溶解した弱酸金属塩又は水酸化ナトリウムの水溶液中
で中和反応させた後、有機溶媒を加えることを特徴とす
るアクリルアミドアルカンスルホン酸金属塩の有機溶液
の製造方法。1. A solution of an organic solution of acrylamidoalkanesulfonic acid metal salt, which is obtained by neutralizing an acrylamidoalkanesulfonic acid in an aqueous solution of a weak acid metal salt or sodium hydroxide, and then adding an organic solvent. Production method.
−アクリルアミド−２−メチルプロパンスルホン酸であ
る請求項１記載の製造方法。2. The acrylamide alkane sulfonic acid is 2
-The production method according to claim 1, which is acrylamido-2-methylpropanesulfonic acid.
請求項１記載の製造方法。3. The method according to claim 1, wherein the organic solvent is dimethylformamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27496993A JPH07101932A (en) | 1993-10-05 | 1993-10-05 | Production of organic solution of acrylamidoalkanesulfonic acid metal salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27496993A JPH07101932A (en) | 1993-10-05 | 1993-10-05 | Production of organic solution of acrylamidoalkanesulfonic acid metal salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07101932A true JPH07101932A (en) | 1995-04-18 |
Family
ID=17549093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27496993A Pending JPH07101932A (en) | 1993-10-05 | 1993-10-05 | Production of organic solution of acrylamidoalkanesulfonic acid metal salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07101932A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0841322A1 (en) * | 1996-11-08 | 1998-05-13 | The Lubrizol Corporation | Dry blending of acrylamidoalkanesulfonic acid monomer with basic compounds |
-
1993
- 1993-10-05 JP JP27496993A patent/JPH07101932A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0841322A1 (en) * | 1996-11-08 | 1998-05-13 | The Lubrizol Corporation | Dry blending of acrylamidoalkanesulfonic acid monomer with basic compounds |
| US5792828A (en) * | 1996-11-08 | 1998-08-11 | The Lubrizol Corporation | Dry blending of acrylamidoalkanesulfonic acid monomer with basic compounds |
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