JPS6150934B2 - - Google Patents
Info
- Publication number
- JPS6150934B2 JPS6150934B2 JP10645483A JP10645483A JPS6150934B2 JP S6150934 B2 JPS6150934 B2 JP S6150934B2 JP 10645483 A JP10645483 A JP 10645483A JP 10645483 A JP10645483 A JP 10645483A JP S6150934 B2 JPS6150934 B2 JP S6150934B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dihydro
- furandione
- formula
- alkali
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 claims description 16
- 150000004716 alpha keto acids Chemical class 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 235000010755 mineral Nutrition 0.000 claims description 5
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
- QHKABHOOEWYVLI-UHFFFAOYSA-N 3-methyl-2-oxobutanoic acid Chemical compound CC(C)C(=O)C(O)=O QHKABHOOEWYVLI-UHFFFAOYSA-N 0.000 description 3
- 239000001388 3-methyl-2-oxobutanoic acid Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001371 alpha-amino acids Chemical class 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- -1 2-pentyl group Chemical group 0.000 description 1
- CKGNFKNZKFVYQG-UHFFFAOYSA-N 3-ethyl-2-oxopentanoic acid Chemical compound CCC(CC)C(=O)C(O)=O CKGNFKNZKFVYQG-UHFFFAOYSA-N 0.000 description 1
- BXOFCIOUUNZDQC-UHFFFAOYSA-N 3-methyl-2-oxohexanoic acid Chemical compound CCCC(C)C(=O)C(O)=O BXOFCIOUUNZDQC-UHFFFAOYSA-N 0.000 description 1
- 239000001668 3-methyl-2-oxopentanoic acid Substances 0.000 description 1
- JVQYSWDUAOAHFM-UHFFFAOYSA-N 3-methyl-2-oxovaleric acid Chemical compound CCC(C)C(=O)C(O)=O JVQYSWDUAOAHFM-UHFFFAOYSA-N 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はα−ケト酸またはその塩の製法に関す
る。
さらに委しくは、置換基を持つジヒドロ−２・
３−フランジオンをアルカリ加水分解して対応す
るα−ケト酸またはその塩を製造する新規な方法
に関するものである。
α−ケト酸には種々の化合物が含まれているが
α−アミノ酸の出発物質、尿毒症及び腎不全の治
療薬、その他農薬の中間体、あるいはヘアートリ
ートメント剤原料などの各方面の用途に用いられ
る有用な化合物である。
従来公知の方法としては
(1) α−アミノ酸にアミノ酸酸化酵素を作用させ
る方法
The Biochemical Journal.50、258（1951）
Jof Biological Chemistry.153、387（1944）
特開昭52−114091
Bull、Chem、Soc、JaPan.31、665（1958）
(2) 不飽和ヒダントインとアルカリ金属水酸化物
の水溶液を反応させる方法
Encycloped ia of Chem.Technology.11、
148（1966）
特開昭53−46920
特開昭54−86217
(3) 芳香族アルデヒドとヒダントインとの縮合物
のアルカリ加水分解による方法
Monat.92、335〜342、343〜351（1961）
(4) シアノ化アシル化合物の加水分解による方法
特開昭53−46919
(5) イソブチルアルデヒドを原料としてハロゲン
化オキシムとなし、これをNaCNでシアノ化オ
キシムとして加水分解する方法
USP 4302402（1980）
等種々の方法が知られているが、(1)のα−アミノ
酸、(2)の不飽和ヒダントイン、(3)のヒダントイン
(4)のシアノアシル化合物のいずれも高価で入手し
にくく工業的に有利な製法とは云えない。
また(5)の方法は比較的入手が容易なイソブチル
アルデヒドを原料とするものであるが、工程が複
雑な上、青酸ソーダを使用するので安全上の問題
があり、且つ収率も良くない。
このような状況に鑑み本発明者らは工業的に有
利なα−ケト酸の製造方法について鋭意検討を行
なつた結果、本発明者らがさきに発明したジヒド
ロ−２・３−フランジオンをアルカリ加水分解す
れば容易にα−ケト酸を得ることができることを
知り本発明に到達した。
即ち本発明の目的は、工業的に有用なα−ケト
酸またはその塩を収率よく工業的に有利に製造す
る方法を提供するにあり、その要旨は一般式
The present invention relates to a method for producing α-keto acids or salts thereof. More preferably, dihydro-2.
The present invention relates to a novel method for producing the corresponding α-keto acid or its salt by alkaline hydrolysis of 3-furandione. α-keto acids contain various compounds, and are used for various purposes such as starting materials for α-amino acids, therapeutic agents for uremia and renal failure, intermediates for other agricultural chemicals, and raw materials for hair treatment agents. It is a useful compound. Conventionally known methods include (1) a method in which an amino acid oxidase acts on α-amino acids The Biochemical Journal. 50 , 258 (1951) Jof Biological Chemistry. 153 , 387 (1944) JP-A-52-114091 Bull, Chem; Soc, Japan. 31 , 665 (1958) (2) Method for reacting unsaturated hydantoin with aqueous solution of alkali metal hydroxide Encyclopedia of Chem.Technology. 11 ,
148 (1966) JP-A-53-46920 JP-A-54-86217 (3) Method by alkaline hydrolysis of condensate of aromatic aldehyde and hydantoin Monat. 92 , 335-342, 343-351 (1961) (4 ) A method by hydrolysis of cyanated acyl compounds JP-A-53-46919 (5) A method of producing a halogenated oxime using isobutyraldehyde as a raw material and hydrolyzing it with NaCN to form a cyanated oxime USP 4302402 (1980) and various other methods. Methods are known, including (1) α-amino acid, (2) unsaturated hydantoin, and (3) hydantoin.
All of the cyanoacyl compounds (4) are expensive and difficult to obtain, and cannot be said to be an industrially advantageous manufacturing method. In addition, method (5) uses isobutyraldehyde, which is relatively easy to obtain, as a raw material, but the process is complicated, and since sodium cyanide is used, there are safety problems, and the yield is not good. In view of this situation, the present inventors conducted intensive studies on an industrially advantageous method for producing α-keto acids, and as a result, dihydro-2,3-furandione, which the present inventors had previously invented, The present invention was achieved by finding that α-keto acids can be easily obtained by alkaline hydrolysis. That is, an object of the present invention is to provide a method for producing an industrially useful α-keto acid or its salt in a high yield and in an industrially advantageous manner.
【式】で表わされるジヒドロ−２・３
−フランジオン類
（ここにR1、R2はそれぞれC1〜C3のアルキル基、
ＲはDihydro-2,3-furandiones represented by the formula (where R 1 and R 2 are each a C 1 to C 3 alkyl group,
R is
【式】で表わされる基を示し、R3、
R4は前記R1、R2と同じ。）を水の存在下、アルカ
リを加えて加水分解し、要すればさらに鉱酸を作
用させることを特徴とする一般式
It represents a group represented by [Formula], and R 3 and R 4 are the same as R 1 and R 2 above. ) is hydrolyzed by adding an alkali in the presence of water, and if necessary, a mineral acid is further applied.
【式】で表わされるα−ケト酸
（ここにR1、R2は前記に同じ。）の製法である。
本発明は従来文献に記載のない新規な方法であ
り、その反応機構は次のごとく推定される。
本発明で用いる一般式This is a method for producing an α-keto acid represented by the formula (where R 1 and R 2 are the same as above). The present invention is a novel method that has not been described in any prior literature, and its reaction mechanism is estimated as follows. General formula used in the present invention
【式】
で表わされるジヒドロ−２・３−フランジオンは
４及び５の位置に置換基を有するジヒドロ−２・
３−フランジオンであり、ＲはDihydro-2,3-furandione represented by the formula is dihydro-2,3-furandione having substituents at the 4 and 5 positions.
3-furandione, R is
【式】で表
わされる基である。
R1、R2、即ちR3、R4は同じであつてもよく異
なつていてもよい。通常C1〜C3のアルキル基で
あり、その例としてはメチル基、エチル基、ｎ−
プロピル基、イソプロピル基が挙げられる。従つ
てIt is a group represented by [Formula]. R 1 and R 2 , that is, R 3 and R 4 may be the same or different. Usually a C1 - C3 alkyl group, examples of which are methyl, ethyl, n-
Examples include propyl group and isopropyl group. accordingly
【式】基の例としてはイソプロピル基が
最もよく用いられるが、この他２−ペンチル基、
３−ペンチル基、２−ブチル基が挙げられる。
本発明の方法で製造されるα−ケト酸の例とし
てはジメチルピルビン酸、ジエチルピルビン酸、
メチルエチルピルビン酸、メチルプロピルピルビ
ン酸等が挙げられる。
本発明で加水分解に用いるアルカリ苛性ソー
ダ、苛性カリ、水酸化カルシウム、水酸化マグネ
シウム等の通常用いられるアルカリを使用する。
また鉱酸としては塩酸、硝酸、硫酸等の無機酸が
用いられ、通常塩酸を用いるのが都合よく、また
好結果が得られる。
次に本発明の実施態様について説明する。
ジヒドロ−２・３−フランジオンを撹拌しなが
らアルカリ水溶液に冷却しながら添加し後、昇温
して加水分解するとα−ケト酸のアルカリ塩を生
成する。副生するアルデヒド、アルドールを水蒸
気蒸溜等の手段により除去回収してから、或はフ
リーのα−ケト酸を望むならば鉱酸により酸性に
してから、エーテル、酢酸エチル、EDCなどの
溶媒にて抽出、晶析、蒸溜などの方法により目的
物を取得することができる。
アルカリは通常水溶液として反応させるが、ア
ルコール類、グリコール類、アルキルエーテル、
アニソール、テトラヒドロフラン、ジオキサン、
ジオキソラン等の溶媒を用いる方が目的物によつ
ては好結果の得られる場合もあり、その際は必ず
理論量以上の水を存在させることが必要である。
原料ジヒドロ−２・３−フランジオン１モルに
対し、加水分解に用いるアルカリは0.5〜5.0モル
好ましくは1.1〜1.4モルを添加すると好結果が得
られる。
また遊離のα−ケト酸を目的とする場合添加す
る鉱酸はジヒドロ−２・３−フランジオン１モル
に対し0.5〜10モル好ましくは1.5〜2.5モルを添加
するのがよい。勿論加水分解のためのアルカリの
量にも関係があり、加水分解に与らなかつた余剰
のアルカリを中和するに必要な量以上に加えるこ
とは必要である。
加水分解に適当な温度は０〜60℃好ましくは25
〜35℃の範囲に保持して行なうと好結果が得られ
る。
本発明は全く新規な方法であり、加水分解とい
う工程の簡単な反応で収率よく製品が得られ、工
業的に有利に利用できる。
以下実施例により本発明をさらに詳細に説明す
る。
実施例 １
ジヒドロ−５−イソプロピル−４・４−ジメチ
ル−２・３−フランジオン20ｇと35％水酸化ナト
ウム17ｇを30℃１時間半かき混ぜ加水分解した
後、濃塩酸30mlを加えて酸性化した。ガスクロマ
トグラフイによる定量値はジメチルピルビン酸の
生成が90％であることを示した。
この溶液をエーテル50mlで抽出し、エーテル層
を無水硫酸ナトリウムで乾燥した後エーテルを留
去し減圧蒸溜して沸点70℃（10mmHg）でジメチ
ルピルビン酸7.2ｇを得た。
実施例 ２〜４
第１表に示す原料を用い実施例１と同様の方法
でアルカリ加水分解し、第１表に示す結果を得
た。[Formula] As an example of the group, isopropyl group is most often used, but in addition, 2-pentyl group,
Examples include 3-pentyl group and 2-butyl group. Examples of α-keto acids produced by the method of the present invention include dimethylpyruvic acid, diethylpyruvic acid,
Examples include methylethylpyruvic acid and methylpropylpyruvic acid. In the present invention, commonly used alkalis such as caustic soda, caustic potash, calcium hydroxide, and magnesium hydroxide are used for hydrolysis.
In addition, as the mineral acid, inorganic acids such as hydrochloric acid, nitric acid, and sulfuric acid are used, and it is usually convenient to use hydrochloric acid and good results can be obtained. Next, embodiments of the present invention will be described. Dihydro-2,3-furandione is added to an alkaline aqueous solution while cooling while stirring, and then heated and hydrolyzed to produce an alkali salt of an α-keto acid. After removing and recovering by-produced aldehydes and aldols by means such as steam distillation, or if free α-keto acids are desired, acidifying them with mineral acid, and then using a solvent such as ether, ethyl acetate, or EDC. The target product can be obtained by methods such as extraction, crystallization, and distillation. Alkali is usually reacted as an aqueous solution, but alcohols, glycols, alkyl ethers,
Anisole, tetrahydrofuran, dioxane,
Depending on the object, better results may be obtained by using a solvent such as dioxolane, and in that case, it is necessary to make sure that more than the theoretical amount of water is present. Good results can be obtained by adding 0.5 to 5.0 mol, preferably 1.1 to 1.4 mol, of the alkali used for hydrolysis to 1 mol of raw material dihydro-2,3-furandione. Further, when the purpose is to obtain a free α-keto acid, the mineral acid to be added is preferably added in an amount of 0.5 to 10 mol, preferably 1.5 to 2.5 mol, per 1 mol of dihydro-2,3-furandione. Of course, the amount of alkali for hydrolysis is also related, and it is necessary to add more than the amount necessary to neutralize the excess alkali that did not participate in the hydrolysis. The suitable temperature for hydrolysis is 0 to 60℃, preferably 25℃.
Good results can be obtained by maintaining the temperature in the range of ~35°C. The present invention is a completely new method, and a product can be obtained in good yield through a simple reaction step of hydrolysis, and can be used industrially to advantage. The present invention will be explained in more detail with reference to Examples below. Example 1 20 g of dihydro-5-isopropyl-4,4-dimethyl-2,3-furandione and 17 g of 35% sodium hydroxide were stirred and hydrolyzed at 30°C for 1.5 hours, and then acidified by adding 30 ml of concentrated hydrochloric acid. . Quantitative values by gas chromatography showed that the production of dimethylpyruvic acid was 90%. This solution was extracted with 50 ml of ether, the ether layer was dried over anhydrous sodium sulfate, and the ether was distilled off and distilled under reduced pressure to obtain 7.2 g of dimethylpyruvic acid with a boiling point of 70°C (10 mmHg). Examples 2 to 4 The raw materials shown in Table 1 were subjected to alkaline hydrolysis in the same manner as in Example 1, and the results shown in Table 1 were obtained.
Claims (1)
Ｒは【式】で表わされる基を示し、R3、 R4は前記R1、R2と同じ意味を持つ。）を水の存在
下、アルカリを加えて加水分解し、要すればさら
に鉱酸を作用させることを特徴とする 一般式【式】で表わされるα− ケト酸の製法。 ２ ジヒドロ−２・３−フランジオン類がジヒド
ロ−５−イソプロピル−４・４−ジメチル−２・
３−フランジオンである特許請求の範囲１記載の
方法。 ３ アルカリが苛性ソーダである特許請求の範囲
１記載の方法。[Claims] 1 Dihydro-2,3-furandiones represented by the general formula [Formula] (where R 1 and R 2 are each a C 1 to C 3 alkyl group,
R represents a group represented by [Formula], and R 3 and R 4 have the same meanings as R 1 and R 2 above. ) is hydrolyzed in the presence of water by adding an alkali, and if necessary, a mineral acid is further allowed to act on the α-keto acid. 2 Dihydro-2,3-furandiones are dihydro-5-isopropyl-4,4-dimethyl-2,
2. The method according to claim 1, wherein the 3-furandione is 3-furandione. 3. The method according to claim 1, wherein the alkali is caustic soda.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10645483A JPS606638A (en) | 1983-06-13 | 1983-06-13 | Production of alpha-ketoacid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10645483A JPS606638A (en) | 1983-06-13 | 1983-06-13 | Production of alpha-ketoacid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS606638A JPS606638A (en) | 1985-01-14 |
| JPS6150934B2 true JPS6150934B2 (en) | 1986-11-06 |
Family
ID=14434038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10645483A Granted JPS606638A (en) | 1983-06-13 | 1983-06-13 | Production of alpha-ketoacid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS606638A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210062681A1 (en) * | 2019-09-04 | 2021-03-04 | Saudi Arabian Oil Company | Systems and Methods for Proactive Operation of Process Facilities Based on Historical Operations Data |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7667076B2 (en) * | 2005-09-14 | 2010-02-23 | Regents Of The University Of California | Amide forming chemical ligation |
-
1983
- 1983-06-13 JP JP10645483A patent/JPS606638A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210062681A1 (en) * | 2019-09-04 | 2021-03-04 | Saudi Arabian Oil Company | Systems and Methods for Proactive Operation of Process Facilities Based on Historical Operations Data |
| US11591936B2 (en) * | 2019-09-04 | 2023-02-28 | Saudi Arabian Oil Company | Systems and methods for proactive operation of process facilities based on historical operations data |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS606638A (en) | 1985-01-14 |
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