JPH10279545A - Production of n,n-dimethylacrylamide - Google Patents
Production of n,n-dimethylacrylamideInfo
- Publication number
- JPH10279545A JPH10279545A JP9094443A JP9444397A JPH10279545A JP H10279545 A JPH10279545 A JP H10279545A JP 9094443 A JP9094443 A JP 9094443A JP 9444397 A JP9444397 A JP 9444397A JP H10279545 A JPH10279545 A JP H10279545A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ester adduct
- dimethylamine
- sulfuric acid
- adduct
- 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.)
- Granted
Links
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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、重合して石油採掘
剤、糊剤等に使用される有用なモノマーであるＮ，Ｎ−
ジメチルアクリルアミドの工業的に有利な製造法に関す
る。BACKGROUND OF THE INVENTION The present invention relates to N, N-monomers which are useful monomers which are polymerized and used for petroleum mining agents, sizing agents and the like.
The present invention relates to an industrially advantageous method for producing dimethylacrylamide.
【０００２】[0002]
【従来の技術】Ｎ，Ｎ，−ジメチルアクリルアミドの工
業的に製造する方法として、例えばＵＳ２４５１４３６
号、特開平４−２０８２５８号、特開平６−１９９７５
２号等に示されるアミンアダクト法が公知である。該方
法は、原料として安価なアクリル酸メチルを用い、以下
の方法でＮ，Ｎ−ジメチルアクリルアミドが製造され
る。 （１）二重結合の保護（アダクト化） アクリル酸メチルとジメチルアミンを反応させ、化３で
表される化合物（以下エステルアダクトという。）に変
換する。2. Description of the Related Art As a method for industrially producing N, N, -dimethylacrylamide, for example, US Pat.
JP-A-4-208258, JP-A-6-19975
The amine adduct method described in No. 2 and the like is known. In this method, inexpensive methyl acrylate is used as a raw material, and N, N-dimethylacrylamide is produced by the following method. (1) Protection of double bond (formation of adduct) Methyl acrylate is reacted with dimethylamine to convert to a compound represented by Formula 3 (hereinafter referred to as ester adduct).
【０００３】[0003]
【化３】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＯＣＨ3 Embedded image (CH 3 ) 2 N—CH 2 CH 2 —COOCH 3
【０００４】（２）アミド化 エステルアダクトにジメチルアミンを反応させ、化４で
表される化合物（以下アミドアダクトという。）に変換
する。(2) Amidation Ester adduct is reacted with dimethylamine to convert it into a compound represented by Chemical formula 4 (hereinafter referred to as amide adduct).
【０００５】[0005]
【化４】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＮ（ＣＨ3）2 ## STR4 ## (CH 3) 2 N-CH 2 CH 2 -CON (CH 3) 2
【０００６】（３）熱分解 アミドアダクトを熱分解し、Ｎ，Ｎ−ジメチルアクリル
アミドを得る。(3) Thermal decomposition The amide adduct is thermally decomposed to obtain N, N-dimethylacrylamide.
【０００７】これら反応の内、アミド化反応では、エス
テルアダクトとジメチルアミンとを等モルで反応させる
と反応終期の反応速度が非常に遅くなるため、通常、ど
ちらかを過剰モル用い未反応物を回収する方法がとられ
ており、その際も、ジメチルアミンは沸点が低く回収に
多大な装置等を要するため、エステルアダクトを過剰に
用い、これの未反応物を回収する方法が一般的である。[0007] Of these reactions, in the amidation reaction, when the ester adduct and dimethylamine are reacted in an equimolar amount, the reaction rate at the end of the reaction becomes extremely slow. In this case, a method of recovering unreacted dimethylamine is generally used, since dimethylamine has a low boiling point and requires a large amount of equipment for recovery. .
【０００８】[0008]
【発明が解決しようとする課題】しかしながら、このよ
うにして回収したエステルアダクトをアミド化反応に再
使用する場合、しばしば反応液中にゲル状物質が生成し
て増粘し、液の取り出し等の作業が困難になり、安定し
た運転が困難であるという欠点があった。However, when the ester adduct recovered in this way is reused in the amidation reaction, a gel-like substance is often formed in the reaction solution to increase the viscosity, and it is difficult to remove the solution. There was a drawback that work became difficult and stable operation was difficult.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、かかる課
題を解決すべく鋭意研究の結果、ゲル化を起こす物質が
主としてアミド化反応で水分により強塩基触媒存在下エ
ステルアダクトから副成するジメチルβ−アラニンであ
ること、エステルアダクト中の水分が３００ｐｐｍ以下
であるとゲル化を起こさないこと、中和に９９〜１００
％硫酸を用いることによりこの条件が満足され回収率を
低下させることなく安定した運転が可能であることを見
いだし、本発明を完成するにいたった。すなわち本発明
は、（１）二重結合の保護：アクリル酸メチルとジメチ
ルアミンとを反応し化３で表されるエステルアダクトに
変換し、（２）アミド化：これを強塩基性触媒存在下、
化３で表される化合物の０．４〜０．９倍モルのジメチ
ルアミンと反応し化４で表されるアミドアダクトとし、
（３）中和・回収：中和・化３で表される未反応物の回
収ののち、（４）熱分解：熱分解してＮ，Ｎ−ジメチル
アクリルアミドを製造する方法において、中和を濃度９
９〜１００％の硫酸で行うＮ，Ｎ−ジメチルアクリルア
ミドの製造法を提供するものである。Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, the substance causing gelation is mainly formed by amidation in the presence of a strong base catalyst in the presence of a strong base catalyst in the amidation reaction. Being dimethyl β-alanine, not causing gelation if the water content in the ester adduct is 300 ppm or less, and 99-100 for neutralization.
It has been found that the use of% sulfuric acid satisfies these conditions and enables stable operation without lowering the recovery rate, and completed the present invention. That is, the present invention provides (1) protection of a double bond: a reaction between methyl acrylate and dimethylamine to convert it into an ester adduct represented by the following chemical formula (3), and (2) amidation: this is carried out in the presence of a strong basic catalyst. ,
Reacting with 0.4 to 0.9 times the molar amount of dimethylamine of the compound represented by the chemical formula 3 to form an amide adduct represented by the chemical formula 4,
(3) Neutralization / Recovery: After recovering the unreacted substance represented by Neutralization / Chemical Formula 3, (4) Pyrolysis: In the method of producing N, N-dimethylacrylamide by pyrolysis, neutralization is performed. Density 9
The present invention provides a method for producing N, N-dimethylacrylamide using 9-100% sulfuric acid.
【００１０】[0010]
【化３】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＯＣＨ3 Embedded image (CH 3 ) 2 N—CH 2 CH 2 —COOCH 3
【００１１】[0011]
【化４】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＮ（ＣＨ3）2 ## STR4 ## (CH 3) 2 N-CH 2 CH 2 -CON (CH 3) 2
【００１２】以下、本発明を詳細に説明する。本発明の
（１）アクリル酸の二重結合へのジメチルアミンの付加
は、両者を混ぜ合わせるだけで無触媒で容易に進行す
る。反応温度は室温から若干高められた温度、好ましく
は３０〜４０℃である。反応は等モルの使用でも５〜６
時間程度で完結するが、予めアミド化に必要なジメチル
アミンを過剰に使用した方が反応速度も速く、反応終了
後も反応液をそのまま次のアミド化に供することができ
るので好ましい。Hereinafter, the present invention will be described in detail. The addition of dimethylamine to the double bond of acrylic acid (1) of the present invention proceeds easily without a catalyst simply by mixing the two. The reaction temperature is a temperature slightly elevated from room temperature, preferably 30 to 40 ° C. The reaction is 5-6 even with equimolar use.
Although the reaction is completed in about an hour, it is preferable to use an excess of dimethylamine necessary for amidation in advance because the reaction speed is high and the reaction solution can be directly used for the next amidation even after the reaction is completed.
【００１３】本発明の（２）アミド化も公知の方法が使
用できるが、以下の方法が望ましい。すなわち、エステ
ルアダクト１モルに対してジメチルアミン０．４〜０．
９倍モル、好ましくは０．７〜０．８倍モルを強塩基性
触媒存在下反応させることにより実施される。使用でき
る強塩基性触媒としてはアルコラート類、中でもソジウ
ムメトキシドが最も好ましい。使用量は、エステルアダ
クトに対して０．０１〜０．０１５モル程度で十分であ
る。反応は常圧で若干高められた温度、好ましくは４０
〜６０℃で実施され、反応時間は条件にもよるが２〜８
時間程度で完結する。Known methods can be used for the amidation (2) of the present invention, but the following method is preferred. That is, dimethylamine 0.4 to 0.1 to 1 mol of ester adduct.
The reaction is carried out by reacting 9 times mol, preferably 0.7 to 0.8 times mol in the presence of a strong basic catalyst. Alcoholates, particularly sodium methoxide, are most preferred as the strong basic catalyst that can be used. About 0.01 to 0.015 mol of the ester adduct is sufficient. The reaction is carried out at a slightly elevated temperature at normal pressure, preferably 40 ° C.
６０60 ° C., and the reaction time varies depending on the conditions.
Complete in about an hour.
【００１４】アミド化反応終了後、アミドアダクト、メ
タノール、未反応のエステルアダクトの混合物が生成す
る。本発明においては、該混合液を（３）中和後減圧下
蒸留することにより未反応のエステルアダクトを回収す
る。該混合物を中和することなくそのまま蒸留分離する
と、釜液に強塩基性触媒が濃縮され、二量体化その他の
副反応を起こすので好ましくない。中和に使用される酸
は、９９〜１００％の硫酸である。硫酸の濃度が低いと
回収エステルアダクトを再利用した場合、ゲル化をおこ
し、一方、硫酸濃度が１００％を越える場合は、すなわ
ちフリーのＳＯ3 ガスが存在すると、装置の腐食等の問
題が生じるので好ましくない。９９〜１００％の硫酸
は、濃硫酸と発煙硫酸から容易に製造されるが、濃硫酸
と発煙硫酸とを一定量比で中和工程に同時に添加するこ
ともできる。発煙硫酸は、発煙の程度が少ないＳＯ3 ２
０％程度のものが取扱い易く好ましい。エステルアダク
トの回収は、通常、１塔もしくは２塔で分離される。例
えば１塔の場合、塔頂よりメタノール、塔低よりアミド
アダクト、中段サイドでエステルアダクトが取り出さ
れ、メタノールは廃棄される。After the completion of the amidation reaction, a mixture of the amide adduct, methanol and unreacted ester adduct is formed. In the present invention, the unreacted ester adduct is recovered by subjecting the mixture to (3) neutralization and distillation under reduced pressure. If the mixture is separated by distillation without neutralization, the strongly basic catalyst is concentrated in the kettle solution, and undesirably causes dimerization and other side reactions. The acid used for neutralization is 99-100% sulfuric acid. If the concentration of sulfuric acid is low, the recovered ester adduct is reused to cause gelation, while if the concentration of sulfuric acid exceeds 100%, that is, if free SO 3 gas is present, problems such as corrosion of the device occur. It is not preferable. Although 99 to 100% sulfuric acid is easily produced from concentrated sulfuric acid and fuming sulfuric acid, concentrated sulfuric acid and fuming sulfuric acid may be simultaneously added to the neutralization step at a fixed ratio. Fuming sulfuric acid is SO 3 2 with a low degree of fuming.
About 0% is preferable because it is easy to handle. The ester adduct is usually separated in one or two columns. For example, in the case of one tower, methanol is taken out from the top of the tower, an amide adduct is taken out from the bottom of the tower, and an ester adduct is taken out in the middle side, and methanol is discarded.
【００１５】アミドアダクトは、（４）熱分解工程に導
かれ、公知の方法で熱分解することによりＮ，Ｎ−ジメ
チルアクリルアミドを得ることができる。The amide adduct is led to a (4) thermal decomposition step, and is thermally decomposed by a known method to obtain N, N-dimethylacrylamide.
【００１６】本発明の特徴は、中和に９９〜１００％硫
酸を用いる点にある。本発明者らは、ゲル化を起こす物
質について検討を重ねたところ、アミド化反応で水分に
より強塩基性触媒存在下、エステルアダクトが加水分解
されたジメチルβ−アラニンであることを見いだした。
中和に使用される濃硫酸には通常３％程度の水分が含ま
れており、未反応のエステルアダクトを回収するととも
に水もリサイクルされている。水を除去する方法の一つ
は蒸留であり、沸点はメタノール＜水＜エステルアダク
ト＜アミドアダクトの順であるので理論的には分離可能
である。しかしながら、例えば蒸留塔の中段温度を高め
にすれば水はメタノール側に完全に排出されるもののエ
ステルアダクトもメタノール中に多く排出されロスが多
く、一方、低めにすればエステルアダクトのロスはない
ものの回収エステルアダクト中に含まれる水分も増加
し、アミド化反応に再使用した場合にゲル化を起こす。
特に連続蒸留においては、フィード液の組成も変化しそ
れに伴い中段温度も変化することからロスあるいはゲル
化を起こすことなく運転することは現実的には不可能で
ある。A feature of the present invention resides in that 99 to 100% sulfuric acid is used for neutralization. The present inventors have repeated studies on substances that cause gelation, and found that the ester adduct is dimethyl β-alanine in which the ester adduct is hydrolyzed in the amidation reaction in the presence of a strongly basic catalyst with water.
The concentrated sulfuric acid used for neutralization usually contains about 3% of water, and unreacted ester adduct is recovered and water is recycled. One of the methods for removing water is distillation, and the boiling point is in the order of methanol <water <ester adduct <amide adduct, and can be separated theoretically. However, for example, if the middle stage temperature of the distillation column is increased, water is completely discharged to the methanol side, but the ester adduct is also largely discharged into the methanol, resulting in a large loss. The water content in the recovered ester adduct also increases, causing gelation when reused in the amidation reaction.
In particular, in continuous distillation, it is practically impossible to operate without loss or gelation because the composition of the feed solution changes and the middle stage temperature changes accordingly.
【００１７】本発明者らは、更にエステルアダクト中の
水分が３００ｐｐｍ以下、あるいは中和反応後の水分が
７５ｐｐｍ以下であると再利用してもゲル化を起こさな
いことを見いだした。かかる知見をもとに９９〜１００
％の硫酸を中和剤として使用することにより、蒸留塔の
運転条件に左右されることなく、またエステルアダクト
をロスすることもなくゲル化することもなく、安定的に
運転できるという、工業的に極めて優れたものである。The present inventors have further found that when the water content in the ester adduct is 300 ppm or less, or the water content after the neutralization reaction is 75 ppm or less, no gelation occurs even when the water is reused. Based on such knowledge, 99-100
% Sulfuric acid as a neutralizing agent enables industrial operation to be performed stably without being affected by the operating conditions of the distillation column, and without causing loss or gelling of the ester adduct. It is extremely excellent.
【００１８】[0018]
【実施例】以下実施例を挙げて本発明を詳細に説明す
る。 実施例１〜２、比較例１〜４ エステル化槽で、アクリル酸メチル１６０ｋｇ／ｈｒと
ジメチルアミン１６７ｋｇ／ｈｒとを４０℃２時間反応
させて得られた仕込液及び回収エステルアダクトを使用
し、種々の中和剤を用いアミド化反応を実施した。反応
条件は以下の通りである。 ◎アミド化槽…常圧、４０℃ ・仕込液：３３０ｋｇ／ｈｒ（ジメチルアミン５１％、
エステルアダクト４９％） ・回収エステルアダクト：７５ｋｇ／ｈｒ ・ソジウムメトキシド２８％メタノール溶液：５．３ｋ
ｇ／ｈｒ ・中和剤：１．３８ｋｇ／ｈｒ ◎蒸留塔 蒸留塔は１塔で、塔頂よりメタノール、塔低よりアミド
アダクト、中段サイドカットでエステルアダクトを取り
だした。 ・塔低液（主としてアミドアダクト）：２６５ｋｇ／ｈ
ｒ ・廃メタノール：６５ｋｇ／ｈｒ ・中段サイドカット（回収エステルアダクト）：７５ｋ
ｇ／ｈｒ 結果を表１に示す。The present invention will be described in detail below with reference to examples. Examples 1-2, Comparative Examples 1-4 In an esterification tank, a charge liquid and a recovered ester adduct obtained by reacting 160 kg / hr of methyl acrylate and 167 kg / hr of dimethylamine at 40 ° C for 2 hours were used. The amidation reaction was performed using various neutralizing agents. The reaction conditions are as follows. ◎ Amidation tank: normal pressure, 40 ° C. ・ Feeding liquid: 330 kg / hr (dimethylamine 51%,
Ester adduct 49%)-Recovered ester adduct: 75kg / hr-Sodium methoxide 28% methanol solution: 5.3k
g / hr Neutralizing agent: 1.38 kg / hr Distillation column A single distillation column was prepared by taking methanol from the top, amide adduct from the bottom of the column, and ester adduct by middle side cut.・ Low tower liquid (mainly amide adduct): 265 kg / h
r Waste methanol: 65 kg / hr Middle side cut (recovered ester adduct): 75 k
g / hr The results are shown in Table 1.
【００１９】[0019]
【表１】 * リサイクリした場合のアミド化槽[Table 1] * Amidation tank in case of recycling
【００２０】[0020]
【発明の効果】以上説明してきたように、本発明による
と、簡便な方法で、エステルアダクトをロスすることも
なくゲル化することもなく、安定的に運転できるとい
う、工業的に極めて優れた製法が提供される。As explained above, according to the present invention, it is possible to stably operate the ester adduct without losing or gelling the ester adduct by a simple method. A recipe is provided.
Claims (1)
反応し化１で表される化合物に変換し、これを強塩基性
触媒存在下、化１で表される化合物の０．４〜０．９倍
モルのジメチルアミンと反応し化２で表される化合物と
し、中和・化１で表される未反応物の回収ののち、熱分
解してＮ，Ｎ−ジメチルアクリルアミドを製造する方法
において、中和を濃度９９〜１００％の硫酸で行うこと
を特徴とする、Ｎ，Ｎ−ジメチルアクリルアミドの製造
法。 【化１】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＯＣＨ3 【化２】（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＮ（ＣＨ3）2 1. A method comprising reacting methyl acrylate with dimethylamine to convert it into a compound represented by the formula (1), and converting the compound represented by the formula (1) to 0.4 to 0.9 in the presence of a strong basic catalyst. A method for producing N, N-dimethylacrylamide by reacting with twice the molar amount of dimethylamine to form a compound represented by Chemical Formula 2, recovering unreacted substances represented by Chemical Formula 1, and then thermally decomposing the compound to obtain N, N-dimethylacrylamide A method for producing N, N-dimethylacrylamide, wherein neutralization is performed with sulfuric acid having a concentration of 99 to 100%. ## STR1 ## (CH 3) 2 N-CH 2 CH 2 -COOCH 3 ## STR2 ## (CH 3) 2 N-CH 2 CH 2 -CON (CH 3) 2
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09444397A JP3976831B2 (en) | 1997-03-31 | 1997-03-31 | Method for producing N, N-dimethylacrylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09444397A JP3976831B2 (en) | 1997-03-31 | 1997-03-31 | Method for producing N, N-dimethylacrylamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10279545A true JPH10279545A (en) | 1998-10-20 |
| JP3976831B2 JP3976831B2 (en) | 2007-09-19 |
Family
ID=14110413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09444397A Expired - Lifetime JP3976831B2 (en) | 1997-03-31 | 1997-03-31 | Method for producing N, N-dimethylacrylamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3976831B2 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000041996A1 (en) * | 1999-01-16 | 2000-07-20 | Ciba Specialty Chemicals Water Treatments Limited | Production of acrylic monomers |
| JP2000273072A (en) * | 1999-03-24 | 2000-10-03 | Kohjin Co Ltd | Production of (meth)acrylamide derivative |
| WO2008102615A1 (en) | 2007-02-20 | 2008-08-28 | Idemitsu Kosan Co., Ltd. | PROCESS FOR PRODUCING β-ALKOXYPROPIONAMIDE |
| WO2010067589A1 (en) | 2008-12-10 | 2010-06-17 | 出光興産株式会社 | Method for producing β-alkoxypropionamide |
| JP2012025675A (en) * | 2010-07-21 | 2012-02-09 | Kohjin Co Ltd | Acrylamide derivative with little yellowing |
| JP2012097005A (en) * | 2010-10-29 | 2012-05-24 | Kohjin Co Ltd | Method of manufacturing hydroxyalkyl (meth) acrylamide |
| CN103111171A (en) * | 2012-12-27 | 2013-05-22 | 山东瑞博龙化工科技股份有限公司 | Cracking tail gas absorption and treatment device for production device of dimethyl acrylamide |
| JP2014193851A (en) * | 2013-02-28 | 2014-10-09 | Fujifilm Corp | Method for manufacturing polyfunctional (meth)acrylamide compound |
| JP2015214547A (en) * | 2015-05-22 | 2015-12-03 | Ｋｊケミカルズ株式会社 | Less yellowing acrylamide derivative |
| JP2017186303A (en) * | 2016-03-30 | 2017-10-12 | Ｋｊケミカルズ株式会社 | MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE |
| CN107673985A (en) * | 2017-12-05 | 2018-02-09 | 淄博益利化工新材料有限公司 | A kind of high yield N, the preparation technology of N DMAAs |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH07145122A (en) * | 1993-11-24 | 1995-06-06 | Mitsui Toatsu Chem Inc | Production of n-alkyl-alpha,beta-unsaturated carboxamide |
| JPH07316111A (en) * | 1994-05-23 | 1995-12-05 | Mitsubishi Rayon Co Ltd | Production of n,n-disubstituted (meth)acrylamide derivative |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07145122A (en) * | 1993-11-24 | 1995-06-06 | Mitsui Toatsu Chem Inc | Production of n-alkyl-alpha,beta-unsaturated carboxamide |
| JPH07316111A (en) * | 1994-05-23 | 1995-12-05 | Mitsubishi Rayon Co Ltd | Production of n,n-disubstituted (meth)acrylamide derivative |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000041996A1 (en) * | 1999-01-16 | 2000-07-20 | Ciba Specialty Chemicals Water Treatments Limited | Production of acrylic monomers |
| JP2000273072A (en) * | 1999-03-24 | 2000-10-03 | Kohjin Co Ltd | Production of (meth)acrylamide derivative |
| US8338645B2 (en) | 2007-02-20 | 2012-12-25 | Idemitsu Kosan Co., Ltd. | Method for producing a β-alkoxypropionamide |
| WO2008102615A1 (en) | 2007-02-20 | 2008-08-28 | Idemitsu Kosan Co., Ltd. | PROCESS FOR PRODUCING β-ALKOXYPROPIONAMIDE |
| WO2010067589A1 (en) | 2008-12-10 | 2010-06-17 | 出光興産株式会社 | Method for producing β-alkoxypropionamide |
| US8604240B2 (en) | 2008-12-10 | 2013-12-10 | Idemitsu Kosan Co., Ltd. | Method for producing β-alkoxypropionamide |
| JP2012025675A (en) * | 2010-07-21 | 2012-02-09 | Kohjin Co Ltd | Acrylamide derivative with little yellowing |
| JP2012097005A (en) * | 2010-10-29 | 2012-05-24 | Kohjin Co Ltd | Method of manufacturing hydroxyalkyl (meth) acrylamide |
| CN103111171A (en) * | 2012-12-27 | 2013-05-22 | 山东瑞博龙化工科技股份有限公司 | Cracking tail gas absorption and treatment device for production device of dimethyl acrylamide |
| JP2014193851A (en) * | 2013-02-28 | 2014-10-09 | Fujifilm Corp | Method for manufacturing polyfunctional (meth)acrylamide compound |
| JP2015214547A (en) * | 2015-05-22 | 2015-12-03 | Ｋｊケミカルズ株式会社 | Less yellowing acrylamide derivative |
| JP2017186303A (en) * | 2016-03-30 | 2017-10-12 | Ｋｊケミカルズ株式会社 | MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE |
| CN107673985A (en) * | 2017-12-05 | 2018-02-09 | 淄博益利化工新材料有限公司 | A kind of high yield N, the preparation technology of N DMAAs |
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