WO1999054281A1 - Procede de production de dimethylacetamide - Google Patents

Procede de production de dimethylacetamide Download PDF

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Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
dimethylamine
reaction
acetic acid
dimethylacetamide
reaction step
Prior art date
Application number
PCT/JP1999/002070
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Toshiaki Komidou
Kazumoto Ogura
Tadashi Irisawa
Toshio Yoshida
Original Assignee
Mitsubishi Rayon Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Rayon Co., Ltd. filed Critical Mitsubishi Rayon Co., Ltd.
Priority to CA002329241A priority Critical patent/CA2329241A1/en
Priority to KR1020007011509A priority patent/KR20010042773A/ko
Publication of WO1999054281A1 publication Critical patent/WO1999054281A1/ja

Links

Classifications

    • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/JP1999/002070 1998-04-20 1999-04-19 Procede de production de dimethylacetamide WO1999054281A1 (fr)

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 (ko) 1998-04-20 1999-04-19 디메틸아세트아미드의 제조방법

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 (fr) 1999-10-28

Family

ID=14871024

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1999/002070 WO1999054281A1 (fr) 1998-04-20 1999-04-19 Procede de production de dimethylacetamide

Country Status (4)

Country Link
KR (1) KR20010042773A (zh)
CN (1) CN1147464C (zh)
CA (1) CA2329241A1 (zh)
WO (1) WO1999054281A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100313669B1 (ko) * 1999-10-14 2001-11-15 박영구 Ｎ,ｎ-디메틸아세트아미드의 제조방법
CN112341353A (zh) * 2020-11-05 2021-02-09 广州市荔盛化学品有限公司 一种丙基甜菜碱及其制备方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1325467C (zh) * 2004-08-26 2007-07-11 西南化工研究设计院 乙酸甲酯和二甲胺合成二甲基乙酰胺的工艺方法
CN100420668C (zh) * 2005-12-29 2008-09-24 西南化工研究设计院 乙酸乙酯和二甲胺合成二甲基乙酰胺的工艺方法
CN100537521C (zh) * 2006-06-23 2009-09-09 中国石油天然气集团公司 一种合成n,n-二甲基乙酰胺的方法
CN106563438B (zh) * 2016-10-12 2020-01-03 中海油天津化工研究设计院有限公司 一种合成酰胺的催化剂以及合成n,n-二甲基丙酰胺的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5382716A (en) * 1976-12-27 1978-07-21 Shiyosutokinsukii Zabuodo Himi Process for preparing dimethylacetamide
DE4432540A1 (de) * 1994-09-13 1995-03-02 Thalmann & Kunde Ohg Verfahren zur Herstellung von Carbonsäuredimethylamiden

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5382716A (en) * 1976-12-27 1978-07-21 Shiyosutokinsukii Zabuodo Himi Process for preparing dimethylacetamide
DE4432540A1 (de) * 1994-09-13 1995-03-02 Thalmann & Kunde Ohg Verfahren zur Herstellung von Carbonsäuredimethylamiden

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 122, 1995, Abstract No. 122:213635; & DE 4432540 A1. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100313669B1 (ko) * 1999-10-14 2001-11-15 박영구 Ｎ,ｎ-디메틸아세트아미드의 제조방법
CN112341353A (zh) * 2020-11-05 2021-02-09 广州市荔盛化学品有限公司 一种丙基甜菜碱及其制备方法
CN112341353B (zh) * 2020-11-05 2022-11-25 广州市荔盛化学品有限公司 一种丙基甜菜碱及其制备方法

Also Published As

Publication number Publication date
CN1147464C (zh) 2004-04-28
CA2329241A1 (en) 1999-10-28
KR20010042773A (ko) 2001-05-25
CN1298382A (zh) 2001-06-06

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