JP3976831B2 - Method for producing N, N-dimethylacrylamide - Google Patents
Method for producing N, N-dimethylacrylamide Download PDFInfo
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- JP3976831B2 JP3976831B2 JP09444397A JP9444397A JP3976831B2 JP 3976831 B2 JP3976831 B2 JP 3976831B2 JP 09444397 A JP09444397 A JP 09444397A JP 9444397 A JP9444397 A JP 9444397A JP 3976831 B2 JP3976831 B2 JP 3976831B2
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- dimethylamine
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- 229940088644 n,n-dimethylacrylamide Drugs 0.000 title claims description 10
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000006386 neutralization reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000007112 amidation reaction Methods 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 9
- 238000001879 gelation Methods 0.000 description 7
- 230000009435 amidation Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- 229940000635 beta-alanine Drugs 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-aminopropionic acid Natural products NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- -1 dimethyl β-alanine Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002699 waste material Substances 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
- 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)
Description
【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。
【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６−１９９７５２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。
【０００３】
【化３】
（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＯＣＨ3
【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。
【０００５】
【化４】
（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＮ（ＣＨ3）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。
【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。
【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。
【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９９〜１００％の硫酸で行うことにより、回収した未反応物中の水分を３００ｐｐｍ以下とし、ジメチルアミンとの反応に再利用することとする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。また、ジメチルアミンと反応する化３で表される化合物が回収されたものである、前記の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。
【００１０】
【化３】
（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＯＣＨ3
【００１１】
【化４】
（ＣＨ3）2Ｎ−ＣＨ2ＣＨ2−ＣＯＮ（ＣＨ3）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。
【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。
【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 ２０％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。
【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。
【００１６】
本発明の特徴は、中和に９９〜１００％硫酸を用いることにより、回収された未反応のエステルアダクトの水分含量を３００ｐｐｍ以下とし、ジメチルアミンとの反応に再利用する点にある。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。
【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。
【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：５．３ｋｇ／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／ｈｒ
・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）：７５ｋｇ／ｈｒ
結果を表１に示す。
【００１９】
【表１】
【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。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an industrially advantageous process for producing N, N-dimethylacrylamide, which is a useful monomer that is polymerized and used in petroleum mining agents, pastes and the like.
[0002]
[Prior art]
As an industrial method for producing N, N, -dimethylacrylamide, for example, the amine adduct method shown in US Pat. No. 2,451,436, JP-A-4-208258, JP-A-6-199752 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) Double bond protection (adducting)
Methyl acrylate and dimethylamine are reacted to convert to a compound represented by Chemical Formula 3 (hereinafter referred to as ester adduct).
[0003]
[Chemical 3]
(CH 3 ) 2 N—CH 2 CH 2 —COOCH 3
[0004]
(2) Amidated ester adduct is reacted with dimethylamine to convert it into a compound represented by chemical formula 4 (hereinafter referred to as amide adduct).
[0005]
[Formula 4]
(CH 3) 2 N-CH 2 CH 2 -CON (CH 3) 2
[0006]
(3) Pyrolysis The amide adduct is pyrolyzed to obtain N, N-dimethylacrylamide.
[0007]
Among these reactions, in the amidation reaction, when the ester adduct and dimethylamine are reacted in equimolar amounts, the reaction rate at the end of the reaction becomes very slow. In this case, since dimethylamine has a low boiling point and requires a large amount of equipment for recovery, a method of recovering the unreacted product using an ester adduct in excess is generally used.
[0008]
[Problems to be solved by the invention]
However, when the ester adduct recovered in this way is reused in the amidation reaction, a gel-like substance is often generated in the reaction liquid to thicken it, making it difficult to take out the liquid, etc., and stable operation. There was a drawback that it was difficult.
[0009]
[Means for Solving the Problems]
As a result of diligent research to solve such problems, the present inventors have determined that the substance that causes gelation is dimethyl β-alanine, which is a by-product of ester adducts in the presence of a strong base catalyst due to moisture in an amidation reaction. When the water content in the adduct is 300 ppm or less, gelation does not occur, and by using 99 to 100% sulfuric acid for neutralization, this condition is satisfied and stable operation is possible without reducing the recovery rate. As a result, the present invention has been completed. That is, the present invention provides (1) protection of double bond: conversion of methyl acrylate and dimethylamine to ester adduct represented by Chemical Formula 3, and (2) amidation: in the presence of a strongly basic catalyst. The amide adduct represented by the chemical formula 4 is reacted with 0.4 to 0.9 times moles of dimethylamine of the compound represented by the chemical formula 3, and (3) neutralization / recovery: represented by the neutralization / chemical formula 3 (4) Thermal decomposition: In the method for producing N, N-dimethylacrylamide by thermal decomposition, neutralization is performed with sulfuric acid having a concentration of 99 to 100%. The present invention provides a method for producing N, N-dimethylacrylamide, wherein the water content in the product is 300 ppm or less and is reused for the reaction with dimethylamine. The present invention also provides a method for producing the above N, N-dimethylacrylamide, wherein the compound represented by Chemical Formula 3 that reacts with dimethylamine is recovered.
[0010]
[Chemical 3]
(CH 3 ) 2 N—CH 2 CH 2 —COOCH 3
[0011]
[Formula 4]
(CH 3) 2 N-CH 2 CH 2 -CON (CH 3) 2
[0012]
Hereinafter, the present invention will be described in detail.
The addition of dimethylamine to the double bond of (1) acrylic acid of the present invention proceeds easily without catalyst simply by mixing the two. The reaction temperature is a temperature slightly increased from room temperature, preferably 30 to 40 ° C. The reaction is completed in about 5 to 6 hours even if equimolar use is used, but the reaction rate is faster if the dimethylamine necessary for amidation in advance is used excessively, and the reaction solution is used for the next amidation as it is after completion of the reaction. Since it can provide, it is preferable.
[0013]
Although (2) amidation of the present invention can be used by a known method, the following method is desirable.
That is, it is carried out by reacting 0.4 to 0.9 times mol, preferably 0.7 to 0.8 times mol of dimethylamine in the presence of a strongly basic catalyst with respect to 1 mol of the ester adduct.
As strongly basic catalysts that can be used, alcoholates, most preferably sodium methoxide are preferred. About 0.01-0.015 mol is sufficient for the usage-amount with respect to ester adduct.
The reaction is carried out at a slightly elevated temperature at normal pressure, preferably 40 to 60 ° C., and the reaction time is about 2 to 8 hours depending on the conditions.
[0014]
After completion of the amidation reaction, a mixture of an amide adduct, methanol, and an unreacted ester adduct is formed. In the present invention, the unreacted ester adduct is recovered by (3) neutralizing and then distilling under reduced pressure.
If the mixture is separated by distillation without neutralization, the strongly basic catalyst is concentrated in the kettle and is not preferable because dimerization and other side reactions occur.
The acid used for neutralization is 99-100% sulfuric acid. If the recovered ester adduct is reused when the concentration of sulfuric acid is low, gelation occurs. On the other hand, if the sulfuric acid concentration exceeds 100%, that is, if free SO 3 gas is present, problems such as corrosion of the apparatus occur. Therefore, it is not preferable.
99-100% sulfuric acid is easily produced from concentrated sulfuric acid and fuming sulfuric acid, but concentrated sulfuric acid and fuming sulfuric acid can be simultaneously added to the neutralization step in a certain ratio. The fuming sulfuric acid is preferably about 20% SO 3 with a low degree of fuming because it is easy to handle.
The recovery of the ester adduct is usually separated in one or two towers. For example, in the case of one column, methanol is taken out from the top of the column, an amide adduct is taken out from the bottom of the column, and an ester adduct is taken out from the middle side, and methanol is discarded.
[0015]
The amide adduct is led to a (4) pyrolysis step, and N, N-dimethylacrylamide can be obtained by pyrolysis by a known method.
[0016]
The feature of the present invention is that the water content of the recovered unreacted ester adduct is reduced to 300 ppm or less by using 99 to 100% sulfuric acid for neutralization and reused for the reaction with dimethylamine. As a result of repeated studies on substances that cause gelation, the present inventors have found that the ester adduct is dimethyl β-alanine hydrolyzed in the presence of a strong basic catalyst by moisture in the amidation reaction. Concentrated sulfuric acid used for neutralization usually contains about 3% of water, and unreacted ester adducts are recovered and water is also recycled. One method of removing water is distillation, and the boiling point is in the order of methanol <water <ester adduct <amide adduct, so that separation is theoretically possible. However, for example, if the middle temperature of the distillation column is increased, water is completely discharged to the methanol side, but the ester adduct is also discharged to a large amount in the methanol, and on the other hand, if it is lower, there is no loss of the ester adduct. The water content in the recovered ester adduct also increases, causing gelation when reused in the amidation reaction. In particular, in continuous distillation, since the composition of the feed liquid changes and the middle stage temperature changes accordingly, it is practically impossible to operate without loss or gelation.
[0017]
The present inventors have further found that gelation does not occur even when reused 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.
By using 99 to 100% sulfuric acid as a neutralizing agent based on such knowledge, without depending on the operating conditions of the distillation column, without losing the ester adduct and without gelling, It is extremely industrially superior in that it can be stably operated.
[0018]
【Example】
Hereinafter, the present invention will be described in detail with reference to examples.
Examples 1-2 and Comparative Examples 1-4
In the esterification tank, the amidation reaction was carried out using various neutralizing agents using the charged solution and the recovered ester adduct obtained by reacting 160 kg / hr of methyl acrylate with 167 kg / hr of dimethylamine for 2 hours at 40 ° C. Carried out.
The reaction conditions are as follows.
◎ Amidation tank: normal pressure, 40 ℃
-Feed liquid: 330 kg / hr
(Dimethylamine 51%, ester adduct 49%)
・ Recovered ester adduct: 75 kg / hr
Sodium methoxide 28% methanol solution: 5.3 kg / hr
・ Neutralizer: 1.38 kg / hr
◎ Distillation tower There was one distillation tower, methanol from the top, amide adduct from the bottom, and ester adduct from the middle side cut.
・ Tower low liquid (mainly amide adduct): 265 kg / hr
-Waste methanol: 65 kg / hr
-Middle stage side cut (recovered ester adduct): 75 kg / hr
The results are shown in Table 1.
[0019]
[Table 1]
【The invention's effect】
As described above, according to the present invention, an industrially excellent production method is provided that can be stably operated by a simple method without losing the ester adduct or gelling. .
Claims (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 |
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| Publication Number | Publication Date |
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| JPH10279545A JPH10279545A (en) | 1998-10-20 |
| JP3976831B2 true JP3976831B2 (en) | 2007-09-19 |
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| JP09444397A Expired - Lifetime JP3976831B2 (en) | 1997-03-31 | 1997-03-31 | Method for producing N, N-dimethylacrylamide |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1140797A1 (en) * | 1999-01-16 | 2001-10-10 | 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 |
| CN101616889B (en) | 2007-02-20 | 2013-08-21 | 出光兴产株式会社 | Preparation method of β-alkoxy propionamides |
| JP5331469B2 (en) | 2008-12-10 | 2013-10-30 | 出光興産株式会社 | Process for producing β-alkoxypropionamides |
| JP2012025675A (en) * | 2010-07-21 | 2012-02-09 | Kohjin Co Ltd | Acrylamide derivative with little yellowing |
| JP5649049B2 (en) * | 2010-10-29 | 2015-01-07 | Ｋｊケミカルズ株式会社 | Process for producing 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 |
| JP5992463B2 (en) * | 2013-02-28 | 2016-09-14 | 富士フイルム株式会社 | Method for producing 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 |
| JP6869529B2 (en) * | 2016-03-30 | 2021-05-12 | Ｋｊケミカルズ株式会社 | Method for Producing β-Substituted Propionic Acid Amide and N-Substituted (Meta) Acrylamide |
| CN107673985B (en) * | 2017-12-05 | 2020-10-02 | 淄博齐塑环保科技有限公司 | Preparation process of high-yield N, N-dimethylacrylamide |
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| JPH07145122A (en) * | 1993-11-24 | 1995-06-06 | Mitsui Toatsu Chem Inc | Process for producing N-alkyl-α, β-unsaturated carboxylic acid amide |
| JPH07316111A (en) * | 1994-05-23 | 1995-12-05 | Mitsubishi Rayon Co Ltd | Process for producing N, N-disubstituted (meth) acrylamide derivative |
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