WO1999054281A1 - Process for producing dimethylacetamide - Google Patents
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- WO1999054281A1 WO1999054281A1 PCT/JP1999/002070 JP9902070W WO9954281A1 WO 1999054281 A1 WO1999054281 A1 WO 1999054281A1 JP 9902070 W JP9902070 W JP 9902070W WO 9954281 A1 WO9954281 A1 WO 9954281A1
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- dimethylamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Definitions
- the present invention relates to a method for efficiently producing dimethylacetamide by reacting acetic acid with dimethylamine.
- Dimethylacetamide is an industrially useful substance as a solvent, an organic synthesis raw material, a pharmaceutical raw material and the like.
- Japanese Patent Publication No. 53-82716 proposes a method in which molybdenum oxide is added as a catalyst to acetic acid to introduce dimethylamine, thereby improving the yield and shortening the reaction time.
- Japanese Patent Application Laid-Open No. Hei 6-2797975 proposes a method for producing a carboxylic acid amide by reacting a carboxylic acid and an amine under pressure while removing water of reaction.
- the material of the pressurizing device must be made acid-resistant, and it is necessary to attach a dehydrating device to the pressurizing device, so that the equipment cost is high. Disclosure of the invention
- the present inventors have conducted intensive studies on the above problems, and as a result, in a method for producing dimethylacetamide from acetic acid and dimethylamine, dimethylamine acetate is gradually decomposed into acetic acid and dimethylamine at a temperature of 10 ° C or more.
- acetic acid is neutralized with dimethylamine at normal pressure and room temperature, and then the decomposition reaction is carried out under pressure.
- the inventors have found that an amide aqueous solution can be obtained at a high yield, and have completed the present invention.
- the present invention provides a method for producing dimethylacetamide from acetic acid and dimethylamine, which comprises the steps of: i) neutralizing acetic acid and dimethylamine at ordinary pressure under a molar ratio of dimethylamine acetic acid of at least 1.01; A) a neutralization reaction step of synthesizing dimethylamine acetate to obtain a reaction product solution containing the same; and b) an amidation reaction step of subjecting the reaction product solution to a reaction under pressure.
- acetic acid and dimethylamine are desired to be as high as possible, but may be of industrial grade.
- acetic acid and dimethylamine are supplied to a reaction tank and neutralized under anhydrous and non-catalytic conditions to synthesize dimethylamine acetate, and a reaction product containing the same is produced. Obtain a liquid.
- Acetic acid and dimethylamine may be supplied simultaneously to the reaction vessel, or acetic acid may be charged first, and dimethylamine may be supplied thereto.
- the ratio is preferably such that dimethylamine is present in excess with respect to acetic acid, and the molar ratio of dimethylamine Z acetic acid is 1.01 or more, preferably 1.01 to 1.5, more preferably 1.01. It is in the range of ⁇ 1.20.
- the reaction temperature is not particularly limited, but is preferably in the range of 30 to 60 ° C.
- the reaction product liquid obtained in the neutralization reaction step is subjected to a reaction under pressure.
- the obtained reaction product solution is withdrawn from the neutralization reaction tank, dimethylamine is further added to the reaction product solution, and the amidation reaction is performed under pressure.
- the reaction product liquid obtained in the neutralization reaction step and dimethylamine may be supplied simultaneously to the reaction tank, or the reaction product liquid obtained in the neutralization reaction step may be supplied to the reaction tank.
- the dimethylamine may be supplied first, and dimethylamine may be supplied thereto.
- Dimethylamine to be added may be liquid or gaseous. The amount of addition is 0.1 to 5, preferably 0.2 to 2, more preferably 0.5 to: acetic acid in molar ratio with respect to acetic acid charged in the neutralization reaction step. It is.
- Dimethylamine and the reaction product liquid obtained in the neutralization reaction step are charged to the amidation reaction tank. After that, the reaction is carried out at a reaction temperature of 100 to 300 ° C, preferably 150 to 250 ° C, a reaction time of 1 to 2 hours, and a reaction pressure of 0.1 to 5 MPa, preferably 1 to 3 MPa.
- reaction pressure is maintained at a predetermined pressure by heating to the above reaction temperature.
- a catalyst can be used.
- the catalyst include molybdenum compounds such as molybdenum oxide and chemolybdic acid, tungstate compounds such as tandene trioxide and phosphotungstic acid, and sodium metavanadate.
- the Mo O 3 0. 6 g was added to Otoku Leeb as a catalyst, where except having conducted the reaction with stirring 1 5 0 to 160 ° C having conducted in the same manner as in Example 1, after for 1 hour
- the reaction rate was 88.1%, and the reaction rate after 2 hours was 94.5. /. Met.
- Dimethylacetamide with low impurity content Can be obtained in high yield.
- Dimethylacetamide is an industrially useful substance as a solvent, a raw material for organic synthesis, a raw material for pharmaceuticals, and the like.
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Abstract
Description
明 細 書 ジメチルァセトアミ ドの製造法 技術分野 Description Manufacturing method for dimethylacetamide Technical field
本発明は、 酢酸とジメチルァミンの反応によりジメチルァセトアミ ドを効率的 に製造する方法に関するものである。 ジメチルァセトアミ ドは溶剤、 有機合成原 料、 医薬原料等として工業上有用な物質である。 The present invention relates to a method for efficiently producing dimethylacetamide by reacting acetic acid with dimethylamine. Dimethylacetamide is an industrially useful substance as a solvent, an organic synthesis raw material, a pharmaceutical raw material and the like.
背景技術 Background art
酢酸とジメチルァミンとからジメチルァセトアミ ドを製造する方法は従来常圧 で行われていたが、 低収率かつ反応時間が長いという不都合があった。 そこで、 特公昭 5 3— 8 2 7 1 6号公報では、 酢酸に触媒として酸化モリブデンを添加し てジメチルァミンを導入することによって収率の向上と反応時間を短縮するとい う方法が提案されているが、 この方法でも反応時間は十分には短縮されていなか つた。 また、 特開平 6— 2 7 9 3 7 5号公報では、 加圧下、 カルボン酸とアミン とを反応水を除去しながら反応させてカルボン酸アミ ドを製造する方法が提案さ れている。 しかし、 この方法は、 加圧装置の材質を耐酸性にすること、 加圧装置 に脱水装置を付属させることが必要となるため、 設備費が高くついていた。 発明の開示 A method for producing dimethylacetamide from acetic acid and dimethylamine has conventionally been carried out at normal pressure, but has the disadvantage of a low yield and a long reaction time. In view of this, Japanese Patent Publication No. 53-82716 proposes a method in which molybdenum oxide is added as a catalyst to acetic acid to introduce dimethylamine, thereby improving the yield and shortening the reaction time. However, even with this method, the reaction time was not sufficiently shortened. Further, Japanese Patent Application Laid-Open No. Hei 6-2797975 proposes a method for producing a carboxylic acid amide by reacting a carboxylic acid and an amine under pressure while removing water of reaction. However, in this method, the material of the pressurizing device must be made acid-resistant, and it is necessary to attach a dehydrating device to the pressurizing device, so that the equipment cost is high. Disclosure of the invention
本発明は、 従来技術の有するこのような問題点を鑑みてなされたものであり、 その目的とするところは、 酢酸とジメチルァミンの反応によってジメチルァセト アミ ドを工業的に製造するにあたって、 反応時間の短縮及び装置を単純化して、 効率的にジメチルァセトアミ ドを製造する方法を提供することにある。 The present invention has been made in view of such problems of the prior art, and has as its object to reduce the reaction time when industrially producing dimethylacetamide by the reaction of acetic acid and dimethylamine. Another object of the present invention is to provide a method for efficiently producing dimethylacetamide by simplifying the apparatus.
本発明者らは上記課題について鋭意検討した結果、 酢酸とジメチルァミンとか らジメチルァセトアミドを製造する方法において、 ジメチルァミンアセテートが 1 0 o °c以上の温度では徐々に酢酸とジメチルァミンとに分解すること、 ジメチ ルァセトアミ ドの収率向上には、 アミド化反応時間の短縮が重要であることをつ きとめた。 そこで、 常圧、 常温で酢酸をジメチルァミンで中和した後、 続いて加 圧下で分解反応を実施することにより、 短時間で不純物の少ないジメチルァセト アミ ド水溶液が高収率で得られることを見出し、 本発明を完成した。 The present inventors have conducted intensive studies on the above problems, and as a result, in a method for producing dimethylacetamide from acetic acid and dimethylamine, dimethylamine acetate is gradually decomposed into acetic acid and dimethylamine at a temperature of 10 ° C or more. In order to improve the yield of dimethylacetamide, it was important to shorten the amidation reaction time. Therefore, acetic acid is neutralized with dimethylamine at normal pressure and room temperature, and then the decomposition reaction is carried out under pressure. The inventors have found that an amide aqueous solution can be obtained at a high yield, and have completed the present invention.
すなわち、 本発明は、 酢酸とジメチルァミンとからジメチルァセトアミ ドを製 造する方法において、 ィ） 酢酸とジメチルァミンとを常圧下、 ジメチルアミン 酢酸のモル比 1 . 0 1以上で中和させて、 ジメチルァミンアセテートを合成し、 それを含む反応生成液を得る中和反応工程、 及び口） この反応生成液を加圧下で 反応に付すアミ ド化反応工程を含む上記方法である。 That is, the present invention provides a method for producing dimethylacetamide from acetic acid and dimethylamine, which comprises the steps of: i) neutralizing acetic acid and dimethylamine at ordinary pressure under a molar ratio of dimethylamine acetic acid of at least 1.01; A) a neutralization reaction step of synthesizing dimethylamine acetate to obtain a reaction product solution containing the same; and b) an amidation reaction step of subjecting the reaction product solution to a reaction under pressure.
発明を実施するための最良の形態 BEST MODE FOR CARRYING OUT THE INVENTION
以下、 本発明について詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の方法に用いられる原料の酢酸及びジメチルァミンはなるべく純度の高 いものが望まれるが工業用の純度であっても差し支えない。 The starting materials used in the method of the present invention, acetic acid and dimethylamine, are desired to be as high as possible, but may be of industrial grade.
本発明の方法における中和反応工程では、 酢酸とジメチルァミンとを反応槽に 供給して、 無水、 無触媒の条件下で中和させて、 ジメチルァミンアセテートを合 成し、 それを含む反応生成液を得る。 In the neutralization reaction step in the method of the present invention, acetic acid and dimethylamine are supplied to a reaction tank and neutralized under anhydrous and non-catalytic conditions to synthesize dimethylamine acetate, and a reaction product containing the same is produced. Obtain a liquid.
酢酸とジメチルァミンは反応槽に同時に供給する力、 又は酢酸を先に仕込み、 そこにジメチルァミンを供給してもよい。 その比率は、 酢酸に対してジメチルァ ミンが過剰に存在するのがよく、 ジメチルァミン Z酢酸のモル比は 1 . 0 1以上、 好ましくは 1 . 0 1〜1 . 5、 より好ましくは 1 . 0 1〜1 . 2 0の範囲である。 反応温度は特に限定されないが、 好ましくは 3 0〜6 0 °Cの範囲である。 Acetic acid and dimethylamine may be supplied simultaneously to the reaction vessel, or acetic acid may be charged first, and dimethylamine may be supplied thereto. The ratio is preferably such that dimethylamine is present in excess with respect to acetic acid, and the molar ratio of dimethylamine Z acetic acid is 1.01 or more, preferably 1.01 to 1.5, more preferably 1.01. It is in the range of ~ 1.20. The reaction temperature is not particularly limited, but is preferably in the range of 30 to 60 ° C.
本発明の方法におけるアミ ド化反応工程では、 上記中和反応工程で得られた反 応生成液を加圧下で反応に付す。 好ましくは、 得られた反応生成液を中和反応槽 から抜き出し、 該反応生成液にさらにジメチルァミンを添加し、 加圧下でアミ ド 化反応を実施する。 In the amidation reaction step in the method of the present invention, the reaction product liquid obtained in the neutralization reaction step is subjected to a reaction under pressure. Preferably, the obtained reaction product solution is withdrawn from the neutralization reaction tank, dimethylamine is further added to the reaction product solution, and the amidation reaction is performed under pressure.
アミ ド化反応槽への仕込みは、 上記中和反応工程で得られた反応生成液とジメ チルァミンとを反応槽に同時に供給してもよいし、 中和反応工程で得られた反応 生成液を先に仕込み、 そこにジメチルァミンを供給してもよい。 添加するジメチ ルァミンは、 液状でもガス状でもよい。 その添加量は、 中和反応工程で仕込んだ 酢酸に対して、 モル比で 0 . 1〜5、 好ましくは、 0 . 2〜2、 より好ましくは 0 . 5〜：！である。 For charging the amidation reaction tank, the reaction product liquid obtained in the neutralization reaction step and dimethylamine may be supplied simultaneously to the reaction tank, or the reaction product liquid obtained in the neutralization reaction step may be supplied to the reaction tank. The dimethylamine may be supplied first, and dimethylamine may be supplied thereto. Dimethylamine to be added may be liquid or gaseous. The amount of addition is 0.1 to 5, preferably 0.2 to 2, more preferably 0.5 to: acetic acid in molar ratio with respect to acetic acid charged in the neutralization reaction step. It is.
アミ ド化反応槽にジメチルァミンと中和反応工程で得られた反応生成液とを仕 込んだ後に、 反応温度 100〜300°C、 好ましくは 1 50〜250°C、 反応時 間 1〜2時間、 反応圧力 0. l〜5MP a、 好ましくは 1〜 3 M P aで反応させ る。 Dimethylamine and the reaction product liquid obtained in the neutralization reaction step are charged to the amidation reaction tank. After that, the reaction is carried out at a reaction temperature of 100 to 300 ° C, preferably 150 to 250 ° C, a reaction time of 1 to 2 hours, and a reaction pressure of 0.1 to 5 MPa, preferably 1 to 3 MPa.
オートクレーブ等の密閉できるアミド化反応槽を使用し、 上記反応温度まで加 温することにより所定の反応圧力に維持する。 Using a tightly closed amidation reaction tank such as an autoclave, the reaction pressure is maintained at a predetermined pressure by heating to the above reaction temperature.
アミ ド化反応終了後、 過剰のジメチルァミンは塔頂からガス状態で未反応原料 として回収することができる。 放圧後、 塔底からジメチルァセトアミ ドを主成分 とする液が得られる。 After the completion of the amidation reaction, excess dimethylamine can be recovered as unreacted raw material in a gaseous state from the top of the tower. After the pressure is released, a liquid containing dimethylacetamide as a main component is obtained from the bottom of the column.
本発明のアミ ド化反応工程においては触媒を用いることができる。 触媒として は、 酸化モリブデン、 ケィモリブデン酸等のモリブデン酸化合物、 三酸化タンダ ステン、 リンタングステン酸等のタングステン酸化合物、 メタバナジン酸ナトリ ゥム等が挙げられる。 In the amidation reaction step of the present invention, a catalyst can be used. Examples of the catalyst include molybdenum compounds such as molybdenum oxide and chemolybdic acid, tungstate compounds such as tandene trioxide and phosphotungstic acid, and sodium metavanadate.
以下、 本発明を実施例をもって具体的に説明するが、 本発明はこの実施例のみ に限定されないことは言うまでもない。 Hereinafter, the present invention will be described specifically with reference to Examples, but it goes without saying that the present invention is not limited to only these Examples.
実施例 1 Example 1
攪拌装置、 還流冷却器付き 500m lセパラブルフラスコに酢酸 120 g (2. 0モル） を仕込み、 冷却下ジメチルァミン 92. 0 g (2. 04モル） で中和し た。 中和液を全量、 加熱 ·攪拌装置付き 500 m 1オートクレーブに移液した。 オートクレーブを密閉した後、 ガス仕込みラインからジメチルァミン 45 g (1 モル） を仕込み密閉した。 これを攪拌しながら、 1 70°C、 最大圧力 2MP aで 1時間反応させた。 反応率は 86. 5%であった。 室温に冷却後、 過剰のジメチ ルァミンを回収し、 その後反応液 220. 7 gを取り出した。 反応液のジメチル ァセトアミ ド濃度は 58. 7%、 反応率は 86. 0% (酢酸ベース） であった。 比較例 1 A 500 ml separable flask equipped with a stirrer and a reflux condenser was charged with 120 g (2.0 mol) of acetic acid, and neutralized with 92.0 g (2.04 mol) of dimethylamine under cooling. The entire amount of the neutralized solution was transferred to a 500 ml autoclave equipped with a heating and stirring device. After sealing the autoclave, 45 g (1 mol) of dimethylamine was charged from the gas charging line and sealed. The mixture was reacted at 170 ° C. and a maximum pressure of 2 MPa for 1 hour with stirring. The reaction rate was 86.5%. After cooling to room temperature, excess dimethylamine was recovered, and then 220.7 g of the reaction solution was taken out. The dimethylacetamide concentration of the reaction solution was 58.7%, and the reaction rate was 86.0% (acetic acid base). Comparative Example 1
攪拌装置、 還流冷却器付き 500m lセパラブルフラスコに酢酸 120 g (2. 0モル） を仕込み、 冷却下ジメチルァミン 92. 0 g (2. 04モル） で中和し た。 中和液を移液せずにそのまま攪拌しながら、 反応温度 1 20°C、 常圧で 1時 間反応を行つたところ、 反応率は 32%、 5時間後の反応率は 55 %、 20時間 の反応率は 69%であった。 比較例 2 A 500 ml separable flask equipped with a stirrer and a reflux condenser was charged with 120 g (2.0 mol) of acetic acid, and neutralized with 92.0 g (2.04 mol) of dimethylamine under cooling. The reaction was conducted for 1 hour at a reaction temperature of 120 ° C and normal pressure while stirring the neutralized solution without transfer.The reaction rate was 32%, and the reaction rate after 5 hours was 55%. The reaction rate over time was 69%. Comparative Example 2
前記セパラブルフラスコに生成水溜出装置を付け、 生成水を系外に抜きながら、 反応温度 1 50°Cで 1時間反応を行った以外は比較例 1と同様の操作を行ったと ころ反応率は 46%であった。 5時間後の反応率は 82 %、 1 0時間後の反応率 は 95%であった。 Attach the generated water distilling device to the separable flask, and perform the same operation as in Comparative Example 1 except that the reaction was performed at a reaction temperature of 150 ° C for 1 hour while draining the generated water out of the system. 46%. The reaction rate after 5 hours was 82%, and the reaction rate after 10 hours was 95%.
実施例 2 Example 2
オートク レープに触媒として Mo O 3 を 0. 6 g添加し、 攪拌しながら 1 5 0〜 160 °Cで反応を行つた以外は実施例 1と同様の操作を行つたところ、 1時 間後の反応率は 88. 1 %、 2時間後の反応率は 94. 5。/。であった。 The Mo O 3 0. 6 g was added to Otoku Leeb as a catalyst, where except having conducted the reaction with stirring 1 5 0 to 160 ° C having conducted in the same manner as in Example 1, after for 1 hour The reaction rate was 88.1%, and the reaction rate after 2 hours was 94.5. /. Met.
実施例 3 Example 3
オートクレ—ブに触媒として WO 3 を 0. 6 g添加し、 攪拌しながら 1 50 〜 1 60 °C、 最大圧力 1. 7 M P aで反応を行つた以外は実施例 1と同様の操作 を行ったところ、 1時間後の反応率は 88. 0%であった。 Otokure - Bed in the WO 3 0. 6 g was added as a catalyst, stirring 1 50 ~ 1 60 ° C, except having conducted the reaction at maximum pressure 1. 7 MP a the same procedure as in Example 1 As a result, the reaction rate after 1 hour was 88.0%.
実施例 4 Example 4
ォ一トクレーブに触媒として Na V03 を 0. 6 g添加し、 攪拌しながら 1 50〜160°C、 最大圧力 1. 7 MP aで反応を行った以外は実施例 1と同様の 操作を行つたところ、 1時間後の反応率は 87. 3 %であった。 O and Na V0 3 0. 6 g was added as a catalyst to an Tokurebu, stirring 1 50 to 160 ° C, line in the same manner as in Example 1 except that the reaction was carried out at a maximum pressure 1. 7 MP a As a result, the reaction rate after one hour was 87.3%.
比較例 3 Comparative Example 3
セパラブルフラスコに触媒として Mo O 3 を 0. 6 g添加し、 反応を行った 以外は比較例 1と同様の操作を行つたところ、 反応率は 45 %であった。 5時間 後の反応率は 69%、 10時間後の反応率は 79 %であった。 The same operation as in Comparative Example 1 was carried out except that 0.6 g of Mo O 3 was added as a catalyst to the separable flask, and the reaction was carried out. As a result, the reaction rate was 45%. The reaction rate after 5 hours was 69%, and the reaction rate after 10 hours was 79%.
比較例 4 Comparative Example 4
セパラブルフラスコに触媒として Mo O 3 を 0. 6 g添カ卩し、 反応を行った 以外は、 比較例 2と同様の操作を行ったところ、 反応率は 82 °/0であった。 5時 間後の反応率は 94°/。、 1 0時間後の反応率は 94 %であった。 The same operation as in Comparative Example 2 was carried out except that 0.6 g of Mo O 3 as a catalyst was added to the separable flask and reacted, and the reaction rate was 82 ° / 0 . The reaction rate after 5 hours is 94 ° /. The reaction rate after 10 hours was 94%.
産業上の利用可能性 Industrial applicability
以上のように、 常圧で酢酸とジメチルァミンを中和した後、 加圧下でアミ ド化 反応すること、 そのアミ ド化反応工程でさらにジメチルァミンを添加し、 加圧下 でアミ ド化反応を行うことにより、 不純物含有量が少ないジメチルァセトアミ ド を高収率で得ることができる。 ジメチルァセトアミ ドは溶剤、 有機合成原料、 医 薬原料等として工業上有用な物質である。 As described above, after acetic acid and dimethylamine are neutralized at normal pressure, the amidation reaction is performed under pressure, and further dimethylamine is added during the amidation reaction step, and the amidation reaction is performed under pressure. Dimethylacetamide with low impurity content Can be obtained in high yield. Dimethylacetamide is an industrially useful substance as a solvent, a raw material for organic synthesis, a raw material for pharmaceuticals, and the like.
Claims
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002329241A CA2329241A1 (en) | 1998-04-20 | 1999-04-19 | Process for producing dimethylacetamide |
| KR1020007011509A KR20010042773A (en) | 1998-04-20 | 1999-04-19 | Process for producing dimethylacetamide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10/123853 | 1998-04-20 | ||
| JP12385398 | 1998-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999054281A1 true WO1999054281A1 (en) | 1999-10-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1999/002070 Ceased WO1999054281A1 (en) | 1998-04-20 | 1999-04-19 | Process for producing dimethylacetamide |
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| Country | Link |
|---|---|
| KR (1) | KR20010042773A (en) |
| CN (1) | CN1147464C (en) |
| CA (1) | CA2329241A1 (en) |
| WO (1) | WO1999054281A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100313669B1 (en) * | 1999-10-14 | 2001-11-15 | 박영구 | Process for preparing N,N- dimethylacetamide |
| CN112341353A (en) * | 2020-11-05 | 2021-02-09 | 广州市荔盛化学品有限公司 | Propyl betaine and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1325467C (en) * | 2004-08-26 | 2007-07-11 | 西南化工研究设计院 | Technological process of synthesizing dimethyl acetylamide with methyl acetate and dimethylamine |
| CN100420668C (en) * | 2005-12-29 | 2008-09-24 | 西南化工研究设计院 | Process method for synthesizing dimethylacetamide from ethyl acetate and dimethylamine |
| CN100537521C (en) * | 2006-06-23 | 2009-09-09 | 中国石油天然气集团公司 | Method for synthesizing N,N dimethyl acetamide in high purity |
| CN106563438B (en) * | 2016-10-12 | 2020-01-03 | 中海油天津化工研究设计院有限公司 | Catalyst for synthesizing amide and method for synthesizing N, N-dimethylpropionamide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382716A (en) * | 1976-12-27 | 1978-07-21 | Shiyosutokinsukii Zabuodo Himi | Process for preparing dimethylacetamide |
| DE4432540A1 (en) * | 1994-09-13 | 1995-03-02 | Thalmann & Kunde Ohg | Process for the preparation of N,N-dimethylcarboxamides |
-
1999
- 1999-04-19 CA CA002329241A patent/CA2329241A1/en not_active Abandoned
- 1999-04-19 WO PCT/JP1999/002070 patent/WO1999054281A1/en not_active Ceased
- 1999-04-19 KR KR1020007011509A patent/KR20010042773A/en not_active Withdrawn
- 1999-04-19 CN CNB99805285XA patent/CN1147464C/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382716A (en) * | 1976-12-27 | 1978-07-21 | Shiyosutokinsukii Zabuodo Himi | Process for preparing dimethylacetamide |
| DE4432540A1 (en) * | 1994-09-13 | 1995-03-02 | Thalmann & Kunde Ohg | Process for the preparation of N,N-dimethylcarboxamides |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, Vol. 122, 1995, Abstract No. 122:213635; & DE 4432540 A1. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100313669B1 (en) * | 1999-10-14 | 2001-11-15 | 박영구 | Process for preparing N,N- dimethylacetamide |
| CN112341353A (en) * | 2020-11-05 | 2021-02-09 | 广州市荔盛化学品有限公司 | Propyl betaine and preparation method thereof |
| CN112341353B (en) * | 2020-11-05 | 2022-11-25 | 广州市荔盛化学品有限公司 | Propyl betaine and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010042773A (en) | 2001-05-25 |
| CN1147464C (en) | 2004-04-28 |
| CA2329241A1 (en) | 1999-10-28 |
| CN1298382A (en) | 2001-06-06 |
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