JP2001163845A5 - - Google Patents
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- JP2001163845A5 JP2001163845A5 JP1999353713A JP35371399A JP2001163845A5 JP 2001163845 A5 JP2001163845 A5 JP 2001163845A5 JP 1999353713 A JP1999353713 A JP 1999353713A JP 35371399 A JP35371399 A JP 35371399A JP 2001163845 A5 JP2001163845 A5 JP 2001163845A5
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- JP
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- Prior art keywords
- ketone
- mol
- aminonitrile
- less
- amount
- 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.)
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- 150000002576 ketones Chemical class 0.000 description 9
- 125000005219 aminonitrile group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N Dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Description
【特許請求の範囲】
【請求項１】 下記一般式（１）
【化１】
【化２】
【請求項２】 Ｒ、Ｒ’の一方が水素原子であり、他方がｔ−ブチル基又はｓｅｃ−ブチル基である請求項１記載の製造方法。
【請求項３】 アルコールが、炭素数１〜４の直鎖状又は分岐状のアルコールである請求項１又は２記載の製造方法。
【請求項４】 ケトンが、アセトン、メチルエチルケトン又はメチルイソブチルケトンである請求項１〜３のいずれか１項記載の製造方法。
[Claims]
1. The following general formula (1)
Embedded image
Embedded image
2. The method according to claim 1, wherein one of R and R ′ is a hydrogen atom, and the other is a t-butyl group or a sec-butyl group.
3. The method according to claim 1, wherein the alcohol is a linear or branched alcohol having 1 to 4 carbon atoms.
4. The method according to claim 1, wherein the ketone is acetone, methyl ethyl ketone or methyl isobutyl ketone.
【０００９】
【課題を解決するための手段】 本発明者らは、上記課題を解決すべく鋭意検討した結果、アミノニトリルを、塩基及び、アミノニトリル１モルに対して０．０１モル以上、１モル未満のケトンの存在下、含水アルコール溶媒中で加水分解する方法であれば、均一系で反応することができ、ケトン由来の環化副生物等がほとんど生成することがないため、簡便に高品質のアミノ酸アミドを高収率で得ることができることを見出し、本発明を完成した。
[0009]
Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that aminonitrile is used in an amount of 0.01 mol or more and less than 1 mol based on 1 mol of base and aminonitrile. If it is a method of hydrolyzing in a hydroalcoholic solvent in the presence of a ketone, the reaction can be performed in a homogeneous system, and cyclized by-products derived from the ketone are hardly generated, so that high-quality amino acids can be easily prepared. The present inventors have found that amides can be obtained in high yield, and have completed the present invention.
本発明の製造方法に用いるケトンとしては、脂肪族ケトンが好ましく、アセトン、メチルエチルケトン、メチルイソブチルケトンが特に好ましい。本発明においては、これらを１種以上用いることができる。ケトンの使用量は使用するケトンの種類によって異なるが、アミノニトリル１モルに対して、０．０１モル以上、１モル未満であることが好ましい。０．０１〜１モル以下であれば、アミノニトリルの加水分解が十分促進されるとともに、生成するアミノ酸アミドとケトンとが反応して環化物が生成することがほとんどない。さらに、経済的観点から、アミノニトリル１モルに対して、ケトンが０．０１〜０．５モルであることが特に好ましい。 As the ketone used in the production method of the present invention, an aliphatic ketone is preferable, and acetone, methyl ethyl ketone, and methyl isobutyl ketone are particularly preferable. In the present invention, one or more of these can be used. The amount of the ketone varies depending on the type of the ketone used , but is preferably 0.01 mol or more and less than 1 mol with respect to 1 mol of aminonitrile. When the amount is 0.01 to 1 mol or less, hydrolysis of aminonitrile is sufficiently promoted, and the generated amino acid amide and ketone hardly react to form a cyclized product. Further, from an economic viewpoint, it is particularly preferable that the ketone is 0.01 to 0.5 mol per 1 mol of aminonitrile.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35371399A JP2001163845A (en) | 1999-12-13 | 1999-12-13 | Method of producing amino acid amide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35371399A JP2001163845A (en) | 1999-12-13 | 1999-12-13 | Method of producing amino acid amide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001163845A JP2001163845A (en) | 2001-06-19 |
| JP2001163845A5 true JP2001163845A5 (en) | 2007-02-01 |
Family
ID=18432728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35371399A Pending JP2001163845A (en) | 1999-12-13 | 1999-12-13 | Method of producing amino acid amide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001163845A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004099506A (en) * | 2002-09-09 | 2004-04-02 | Mitsubishi Rayon Co Ltd | Method for producing amino acid amide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL182954C (en) * | 1975-08-20 | 1988-06-16 | Stamicarbon | PROCESS FOR PREPARING ALFA-AMINO ACID AMIDE |
| FR2372797A1 (en) * | 1976-12-03 | 1978-06-30 | Anvar | PROCESS FOR CHEMICAL CATALYTIC HYDROLYSIS OF A-AMINO-NITRILS OR THEIR SALTS |
| JPS5817741B2 (en) * | 1981-03-26 | 1983-04-09 | 三菱瓦斯化学株式会社 | Method for producing α-amino acid amide |
| NL8600131A (en) * | 1986-01-22 | 1987-08-17 | Stamicarbon | PROCESS FOR THE PREPARATION OF ALFA-AMINO-ALFA-METHYLCARBONIC ACIDS AND ALFA-AMINO-ALFA-CYCLOALKYL CARBONIC ACIDS. |
| NL8600132A (en) * | 1986-01-22 | 1987-08-17 | Stamicarbon | PROCESS FOR THE PREPARATION OF ALFA-AMINO-ALFA HYDROGEN CARBONIC ACID AMIDS. |
| JPH03246267A (en) * | 1990-02-22 | 1991-11-01 | Kyowa Yuka Kk | Production of glycinamide |
-
1999
- 1999-12-13 JP JP35371399A patent/JP2001163845A/en active Pending
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