JP2013245192A - フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 - Google Patents
フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 Download PDFInfo
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Landscapes
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Abstract
【解決手段】 ケトンとジアミンを、有機溶剤中にケトン基とアミノ基との比率が、モル比で0.3以上で仕込み、ケトン基とアミノ基との反応と反応系から水の排出とを行って一つのアミノ基とケチミン基を含む化合物(A)を含む混合物を得る工程で、該反応を、ジアミン1モルに対して生成する水が0.6〜1.95モルとなるまで行う工程と、
化合物(A)とフッ素化脂肪族基を含むスルホニルクロライド(B)を反応させて、ケチミン基を有するフッ素化脂肪族基含有化合物(C)を得る工程と、
化合物(C)が有するケチミン基を加水分解する工程
を含むフッ素化脂肪族基を含むスルホニルアミド化合物の製法、該化合物とハロゲン化有機酸の金属塩とを反応させるアニオン性親水基含有界面活性剤の製法。
【選択図】 なし
Description
1.ジアミン化合物とケトン化合物とを反応させて得られる一つのアミン基と一つのケチミン基を有する化合物はアミノ基を一つしか有していない。その為、この化合物1分子はフッ素化脂肪族基を含むスルホニルクロライド化合物1分子としか反応せず、前記のようなフッ素化脂肪族基を含むスルホニルクロライド化合物が1分子用いられた副生成物が生成しない。
2.一つのアミン基と一つのケチミン基を有する化合物とフッ素化脂肪族基を含むスルホニルクロライド化合物とを反応させて得られる反応物に水を加えることにより、該ケチミン基が加水分解されて、フッ素化脂肪族基を含むスルホニルアミドとケトンとなる。
3.ジアミン化合物とケトン化合物との反応は可逆反応であり、ジアミン化合物とケトン化合物とを反応させる反応系には、ジアミン化合物、ケトン化合物、ジアミン化合物1分子とケトン化合物1分子との反応物(一つのアミン基と一つのケチミン基を有する化合物)、ジアミン化合物1分子とケトン化合物2分子との反応物(副生成物)との混合物となるが、反応系に仕込む際のジアミン化合物のアミノ基のモル量とケトン化合物のケトン基のモル量を特定の範囲とすることで、副生成物の生成量を極力抑えつつ、また、ジアミン化合物の量も極力抑えることができる。
4.ジアミン化合物とケトン化合物とを反応させると水が生成する。この反応は平衡反応のため、反応を進行させるためにこの水は反応系から排出する必要があるが、水に溶け易いケトン化合物を用いると、水の排出と共にケトン化合物が系外へと排出されてしまう為、前記3.においてモル量を特定の範囲に仕込んでもケトン化合物が不足してしまい、目的とする一つのアミン基と一つのケチミン基を有する化合物を最大効率下で得にくい。
5.前記4.を解決するためには、沸点が水より高いケトン化合物を用いればよい。
本発明は上記知見に基づき完成したものである。
該混合物中の化合物(A)とフッ素化脂肪族基を含むスルホニルクロライド化合物(B)とを反応させて、ケチミン基を有するフッ素化脂肪族基含有化合物(C)を得る第二工程と、
該化合物(C)が有するケチミン基を加水分解することにより化合物(C)中にアミノ基を生成する第三工程
を含むことを特徴とするスルホニルアミド化合物の製造方法を提供するものである。
A−II N−置換体ポリエチレンイミン
精留塔を備えた清浄な3Lセパラブルフラスコに1,3−プロパンジアミンを216.7g、メチルイソブチルケトン526.1gを仕込んだ。フラスコ内の反応系内の温度を150℃まで昇温し、6時間かけて1,3−プロパンジアミンとメチルイソブチルケトンとの反応と、生成される水の精留による系外への排出を行い、一つのアミノ基と一つのケチミン基を有する化合物を含む混合物を得た。脱水停止後、反応系内の温度を30℃まで降温した。この反応で得られた水の生成量は1.2モルであった。
清浄な3Lセパラブルフラスコに1,3−プロパンジアミンを148.2g、トルエン134gを仕込んだ。3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロオクタン−1−スルフォニルクロライド89.3gをトルエン356.9gに溶解した溶液を調製した。攪拌中の3Lセパラブルフラスコに該溶液を仕込んだ。発熱が収まった後、45℃で2時間攪拌した。1−ブタノール400gとイオン交換水342gとを投入し、80℃へ昇温した。80℃へ到達後、攪拌を停止し、45℃へ降温した。45℃へ到達後、1時間静置し、水層を分液した。分液した水層は390gであった。
Claims (7)
- 沸点が110〜200℃のケトン化合物(a1)とジアミン化合物(a2)とを、ケトン化合物(a1)が有するケトン基(a1−1)とジアミン化合物(a2)が有するアミノ基(a2−1)との比率が、モル比〔(a1−1)/(a2−1)〕で0.3以上となる範囲で反応系に仕込み、ケトン化合物(a1)が有するケトン基(a1−1)とジアミン化合物(a2)が有するアミノ基(a2−1)との反応と該反応を行う反応系から該反応で生成される水の排出とを行って一つのアミノ基と一つのケチミン基とを有する化合物(A)を含む混合物を得る工程であり、該反応を、仕込んだジアミン化合物(a2)1モルに対してケトン基(a1−1)とアミノ基(a2−1)との反応により生成する水が0.6〜1.95モルとなるまで行う第一工程と、
該混合物中の化合物(A)とフッ素化脂肪族基を含むスルホニルクロライド化合物(B)とを反応させて、ケチミン基を有するフッ素化脂肪族基含有化合物(C)を得る第二工程と、
該化合物(C)が有するケチミン基を加水分解することにより化合物(C)中にアミノ基を生成する第三工程
を含むことを特徴とするスルホニルアミド化合物の製造方法。 - 前記第一工程において、ケトン化合物(a1)とジアミン化合物(a2)とを、ケトン基(a1−1)とアミノ基(a2−1)とのモル比〔(a1−1)/(a2−1)〕で0.5〜0.95となる範囲で仕込む、請求項1記載のフッ素化脂肪族基を含むスルホニルアミド化合物の製造方法。
- 前記第一工程において、仕込んだジアミン化合物(a2)1モルに対してケトン基(a1−1)とアミノ基(a2−1)との反応により生成する水が1.0〜1.85モルとなるまでケトン基(a1−1)とアミノ基(a2−1)との反応を行う請求項1記載のフッ素化脂肪族基を含むスルホニルアミド化合物の製造方法。
- 前記ケトン化合物(a1)がメチルイソブチルケトンで、ジアミン化合物(a2)が1,3−プロパンジアミンである請求項1記載のフッ素化脂肪族基を含むスルホニルアミド化合物の製造方法。
- 前記第二工程において、フッ素化脂肪族基を含むスルホニルクロライド化合物(B)が有するスルホニルクロライド基1モルに対して化合物(A)が有するアミノ基が1.5〜10となる範囲で化合物(A)とフッ素化脂肪族基を含むスルホニルクロライド化合物(B)とを反応させる請求項1記載のフッ素化脂肪族基を含むスルホニルアミド化合物の製造方法。
- 前記ケトン化合物(a1)とジアミン化合物(a2)とを120〜180℃の環境下で反応させる請求項1記載のフッ素化脂肪族基を含むスルホニルアミド化合物の製造方法。
- 請求項1〜6のいずれか1項記載の製造方法で得られるフッ素化脂肪族基を含むスルホニルアミド化合物とハロゲン化有機酸の金属塩とを反応させることを特徴とするアニオン性親水基含有界面活性剤の製造方法。
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WO2011005642A1 (en) * | 2009-07-10 | 2011-01-13 | E. I. Du Pont De Nemours And Company | Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines |
JP5522501B2 (ja) * | 2012-05-18 | 2014-06-18 | Dic株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
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WO2011005642A1 (en) * | 2009-07-10 | 2011-01-13 | E. I. Du Pont De Nemours And Company | Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines |
JP5522501B2 (ja) * | 2012-05-18 | 2014-06-18 | Dic株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
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