JPH0741462A - Production of 2-hydroxymethylmercaptobutyric acid - Google Patents
Production of 2-hydroxymethylmercaptobutyric acidInfo
- Publication number
- JPH0741462A JPH0741462A JP5185903A JP18590393A JPH0741462A JP H0741462 A JPH0741462 A JP H0741462A JP 5185903 A JP5185903 A JP 5185903A JP 18590393 A JP18590393 A JP 18590393A JP H0741462 A JPH0741462 A JP H0741462A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxymethylmercaptobutyric
- reaction
- production
- producing
- 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.)
- Pending
Links
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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は２−ヒドロキシメチルメ
ルカプト酪酸アミドを加水分解して２−ヒドロキシメチ
ルメルカプト酪酸を製造する方法に関する。２−ヒドロ
キシメチルメルカプト酪酸は飼料として多量に使用され
ており、極めて重要な化合物である。TECHNICAL FIELD The present invention relates to a method for producing 2-hydroxymethylmercaptobutyric acid by hydrolyzing 2-hydroxymethylmercaptobutyric acid amide. 2-Hydroxymethylmercaptobutyric acid is used as a feed in large amounts and is a very important compound.
【０００２】[0002]
【従来の技術】２−ヒドロキシメチルメルカプト酪酸の
工業的製造方法として、アクロレインとメチルメルカプ
タン及び青酸を原料とする方法が工業化されている。こ
の方法はアクロレインとメチルメルカプタン及び青酸か
らα−ヒドロキシメチルメルカプトブチロニトリルを合
成し、次に２−ヒドロキシメチルメルカプト酪酸アミド
を合成し更に過剰の硫酸存在下で水和反応することによ
り２−ヒドロキシメチルメルカプト酪酸を得る方法であ
る。2. Description of the Related Art As a method for industrially producing 2-hydroxymethylmercaptobutyric acid, a method using acrolein, methylmercaptan and hydrocyanic acid as raw materials has been industrialized. In this method, α-hydroxymethylmercaptobutyronitrile is synthesized from acrolein, methyl mercaptan and hydrocyanic acid, and then 2-hydroxymethylmercaptobutyric acid amide is synthesized, followed by hydration reaction in the presence of excess sulfuric acid to give 2-hydroxymethyl. It is a method of obtaining methyl mercaptobutyric acid.
【０００３】[0003]
【発明が解決しようとする課題】この方法は、反応が容
易であり収率も高く一見優れているように見える。しか
しこの方法の大きな欠点は、大量の廃硫酸及び硫酸アン
モニウムの副生を伴い、この処理費用が高くこれが２−
ヒドロキシメチルメルカプト酪酸の製造コストを圧迫す
るという欠点がある。This method seems to be excellent because the reaction is easy and the yield is high. However, a major drawback of this method is that it involves a large amount of waste sulfuric acid and ammonium sulfate as a by-product, and the cost of this treatment is high.
There is a drawback that the production cost of hydroxymethyl mercaptobutyric acid is suppressed.
【０００４】[0004]
【課題を解決するための手段】本発明者は、これらの問
題点を解決するために鋭意検討を行った結果、ヘテロポ
リ酸又はその塩類が２−ヒドロキシメチルメルカプト酪
酸アミドの加水分解に対して高い活性を有することを見
出し、全く硫酸アンモニウムの副生しない製造方法を完
成することができた。Means for Solving the Problems As a result of intensive studies to solve these problems, the present inventor has found that heteropolyacids or salts thereof are high in hydrolysis of 2-hydroxymethylmercaptobutyric acid amide. It was found that they have activity, and they were able to complete a production method in which no ammonium sulfate was by-produced.
【０００５】すなわち本発明は２−ヒドロキシメチルメ
ルカプト酪酸アミドをヘテロポリ酸又はその塩類の存在
下、液相で水と接触させて加水分解することを特徴とす
る２−ヒドロキシメチルメルカプト酪酸の製造方法であ
る。That is, the present invention provides a method for producing 2-hydroxymethylmercaptobutyric acid, which comprises hydrolyzing 2-hydroxymethylmercaptobutyric acid amide in the liquid phase in the presence of heteropolyacid or salts thereof by contacting with water. is there.
【０００６】加水分解で同時に発生するアンモニアは２
−ヒドロキシメチルメルカプト酪酸アミドの製造原料の
青酸を製造工程で使用することが出来、従来硫酸アンモ
ニウムとして産業廃棄物としていたがリサイクル使用さ
れるため、極めて工業的に価値の高い方法である。Ammonia generated at the same time by hydrolysis is 2
Since it is possible to use hydrocyanic acid, which is a raw material for the production of hydroxymethylmercaptobutyric acid amide, in the production process, and it was conventionally used as industrial waste as ammonium sulfate, but it is recycled, which is an extremely industrially valuable method.
【０００７】本発明の方法は水又は有機溶媒に２−ヒド
ロキシメチルメルカプト酪酸アミドを溶解した後、ヘテ
ロポリ酸又はその塩類を加え、更に水を加えて加熱し、
ヒドロキシメチルメルカプト酪酸アミドを加水分解して
行う。According to the method of the present invention, 2-hydroxymethylmercaptobutyric acid amide is dissolved in water or an organic solvent, then heteropolyacid or a salt thereof is added, and water is further added and heated.
It is carried out by hydrolyzing hydroxymethylmercaptobutyric acid amide.
【０００８】ヘテロポリ酸は多種元素のオキシ酸縮合体
であり、例えばモンブドリン酸、モリブドセシウムリン
酸、モリブドカリウムリン酸、モンブドタングステンリ
ン酸、モンブドセシウムケイ素リン酸、モリブドバナジ
ウムリン酸等が挙げられる。これらのヘテロポリ酸又は
その塩類は溶液状態又は懸濁状態で用いることができ、
単独または混合して使用することが出来る。Heteropolyacids are oxyacid condensates of various elements, and include, for example, monbudric acid, molybdocesium phosphoric acid, molybdopotassium phosphoric acid, monbudtungsten phosphoric acid, monbuddocesium silicon phosphoric acid, molybdovanadium phosphoric acid. Etc. These heteropoly acids or salts thereof can be used in a solution state or a suspension state,
They can be used alone or as a mixture.
【０００９】ヘテロポリ酸又はその塩類の量は２−ヒド
ロキシメチルメルカプト酪酸アミドに対して約０．００
１〜０．１倍モルの範囲で使用される。反応に用いる水
の量は２−ヒドロキシメチルメルカプト酪酸アミドに対
して等量以上であればよいが、好ましくは約１０倍以上
である。The amount of the heteropoly acid or its salt is about 0.00 based on 2-hydroxymethylmercaptobutyric acid amide.
It is used in the range of 1 to 0.1 times mol. The amount of water used in the reaction may be equal to or more than that of 2-hydroxymethylmercaptobutyric acid amide, but is preferably about 10 times or more.
【００１０】反応は約５０〜２５０℃、好ましくは８０
〜２２０で実施され、回分法又は連続法で行う。反応時
間は反応温度、触媒量、水の量によって異なるが、通常
は５分〜６時間である。反応圧力は通常反応に用いられ
る水、有機溶媒及び反応により発生するアンモニア等の
自生圧力下で実施される。この発生するアンモニアは必
要に応じて適宜抜きながら反応させることも可能であ
る。The reaction is about 50-250 ° C, preferably 80
~ 220, performed in batch or continuous mode. The reaction time varies depending on the reaction temperature, the amount of catalyst and the amount of water, but is usually 5 minutes to 6 hours. The reaction pressure is usually under the autogenous pressure of water, an organic solvent and ammonia generated by the reaction which are used in the reaction. It is also possible to react the generated ammonia while appropriately extracting it.
【００１１】生成した２−ヒドロキシメチルメルカプト
酪酸は、加水分解終了液から触媒等の不溶解物を除去し
た後、アンモニアを留出除去して、有機溶剤たとえばメ
チルエチルケトン等で抽出後、溶剤を留出除去すること
により単離される。The produced 2-hydroxymethylmercaptobutyric acid is prepared by removing insoluble matters such as a catalyst from the hydrolyzed solution, distilling off ammonia, extracting with an organic solvent such as methyl ethyl ketone, and distilling the solvent. It is isolated by removing.
【００１２】[0012]
【実施例１】２００ｍｌのオ−トクレ−ブに２−ヒドロ
キシメチルメルカプト酪酸アミド１４．９ｇ、水１００
ｇ、モリブドセシウムリン酸のアンモニウム塩を１．０
ｇを加え、１３５℃で２．５時間反応した。反応終了後
オ−トクレ−ブを室温まで冷却し残圧をパ−ジ後、反応
液を取り出しこの液体クロマトグラフィ−で分析した結
果、２−ヒドロキシメチルメルカプト酪酸が１３．４ｇ
（収率９２％）生成していることが判明した。Example 1 Into 200 ml of autoclave, 14.9 g of 2-hydroxymethylmercaptobutyric acid amide and 100 parts of water.
g, 1.0 ammonium salt of molybdocesium phosphate
g was added and the mixture was reacted at 135 ° C. for 2.5 hours. After the reaction was completed, the autoclave was cooled to room temperature, the residual pressure was purged, and the reaction solution was taken out and analyzed by this liquid chromatography. As a result, 13.4 g of 2-hydroxymethylmercaptobutyric acid was obtained.
(Yield 92%) It was found to be produced.
【００１３】[0013]
【実施例２〜４】使用する触媒のヘテロポリ酸を変更し
た以外は実施例１と同一の方法で反応を実施した。結果
は表１の通りである。Examples 2 to 4 The reaction was carried out in the same manner as in Example 1 except that the heteropoly acid of the catalyst used was changed. The results are shown in Table 1.
【００１４】[0014]
【表１】 [Table 1]
【００１５】[0015]
【比較例１】触媒のヘテロポリ酸を除いた以外は実施例
１と同一の方法で反応を実施した。その結果２−ヒドロ
キシメチルメルカプト酪酸の収率は１１％であった。Comparative Example 1 The reaction was carried out in the same manner as in Example 1 except that the catalyst heteropolyacid was removed. As a result, the yield of 2-hydroxymethylmercaptobutyric acid was 11%.
【００１６】[0016]
【発明の効果】本発明によれば、２−ヒドロキシメチル
メルカプト酪酸アミドから温和な条件下、高収率で２−
ヒドロキシメチルメルカプト酪酸を製造することがで
き、硫酸アンモニウムの副生を伴わない工業的に極めて
有用なプロセスである。INDUSTRIAL APPLICABILITY According to the present invention, 2-hydroxymethyl mercaptobutyric acid amide can be produced in a high yield under mild conditions.
Hydroxymethylmercaptobutyric acid can be produced, and is an industrially extremely useful process without the by-product of ammonium sulfate.
Claims (1)
ドをヘテロポリ酸又はその塩類の存在下、液相で水と接
触させて加水分解することを特徴とする２−ヒドロキシ
メチルメルカプト酪酸の製造方法。1. A process for producing 2-hydroxymethylmercaptobutyric acid, which comprises hydrolyzing 2-hydroxymethylmercaptobutyric acid amide in the liquid phase by contacting it with water in the presence of a heteropolyacid or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5185903A JPH0741462A (en) | 1993-07-28 | 1993-07-28 | Production of 2-hydroxymethylmercaptobutyric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5185903A JPH0741462A (en) | 1993-07-28 | 1993-07-28 | Production of 2-hydroxymethylmercaptobutyric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0741462A true JPH0741462A (en) | 1995-02-10 |
Family
ID=16178903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5185903A Pending JPH0741462A (en) | 1993-07-28 | 1993-07-28 | Production of 2-hydroxymethylmercaptobutyric acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0741462A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008132605A1 (en) * | 2007-04-25 | 2008-11-06 | Toyota Jidosha Kabushiki Kaisha | Plant-fiber-material transformation method |
| DE102006037258B4 (en) * | 2005-08-10 | 2009-12-31 | Kabushiki Kaisha Ogura, Ebina | Cutting blade for cutting rod-like members and cutting machine, on which the cutting blade is fixed |
| US8409356B2 (en) | 2008-06-03 | 2013-04-02 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
| US8460472B2 (en) | 2008-06-03 | 2013-06-11 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
| US8460471B2 (en) | 2008-06-03 | 2013-06-11 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
| US8486197B2 (en) | 2007-09-05 | 2013-07-16 | Toyota Jidosha Kabushiki Kaisha | Method of saccharification and separation for plant fiber materials |
-
1993
- 1993-07-28 JP JP5185903A patent/JPH0741462A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006037258B4 (en) * | 2005-08-10 | 2009-12-31 | Kabushiki Kaisha Ogura, Ebina | Cutting blade for cutting rod-like members and cutting machine, on which the cutting blade is fixed |
| WO2008132605A1 (en) * | 2007-04-25 | 2008-11-06 | Toyota Jidosha Kabushiki Kaisha | Plant-fiber-material transformation method |
| AU2008243879B2 (en) * | 2007-04-25 | 2010-11-25 | Toyota Jidosha Kabushiki Kaisha | Plant-fiber-material transformation method |
| US8382905B2 (en) | 2007-04-25 | 2013-02-26 | Toyota Jidosha Kabushiki Kaisha | Plant-fiber-material transformation method |
| US8486197B2 (en) | 2007-09-05 | 2013-07-16 | Toyota Jidosha Kabushiki Kaisha | Method of saccharification and separation for plant fiber materials |
| US8409356B2 (en) | 2008-06-03 | 2013-04-02 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
| US8460472B2 (en) | 2008-06-03 | 2013-06-11 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
| US8460471B2 (en) | 2008-06-03 | 2013-06-11 | Toyota Jidosha Kabushiki Kaisha | Method for glycosylating and separating plant fiber material |
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