JPH02121962A - Production of mercaptocarboxylic acid - Google Patents
Production of mercaptocarboxylic acidInfo
- Publication number
- JPH02121962A JPH02121962A JP63272654A JP27265488A JPH02121962A JP H02121962 A JPH02121962 A JP H02121962A JP 63272654 A JP63272654 A JP 63272654A JP 27265488 A JP27265488 A JP 27265488A JP H02121962 A JPH02121962 A JP H02121962A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acid
- mercaptocarboxylic acid
- solution
- sulfur compound
- 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
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims abstract description 20
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 14
- 150000002825 nitriles Chemical class 0.000 claims abstract description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 abstract description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 10
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011593 sulfur Substances 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- OLPXIHXXKBDZES-UHFFFAOYSA-L 37488-76-9 Chemical compound [Na+].[Na+].[S-]S[S-] OLPXIHXXKBDZES-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YJGLJZCJQQYDRF-UHFFFAOYSA-L [K+].[K+].[S-]S[S-] Chemical compound [K+].[K+].[S-]S[S-] YJGLJZCJQQYDRF-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ISBHMJZRKAFTGE-ONEGZZNKSA-N (e)-pent-2-enenitrile Chemical compound CC\C=C\C#N ISBHMJZRKAFTGE-ONEGZZNKSA-N 0.000 description 1
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- LTJSXGVQCAVSJW-UHFFFAOYSA-N [K+].[K+].[S-][S-] Chemical compound [K+].[K+].[S-][S-] LTJSXGVQCAVSJW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- DVBRNDGHBLXMCR-UHFFFAOYSA-L dipotassium tetrasulfide Chemical compound [K+].[K+].[S-]SS[S-] DVBRNDGHBLXMCR-UHFFFAOYSA-L 0.000 description 1
- ZLCCLBKPLLUIJC-UHFFFAOYSA-L disodium tetrasulfane-1,4-diide Chemical compound [Na+].[Na+].[S-]SS[S-] ZLCCLBKPLLUIJC-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は水硫化アルカリ水溶液とアクリロニトリル等の
不飽和ニトリルを用いたβ−メルカプトプロピオン酸の
如きメルカプトカルボン酸の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing a mercaptocarboxylic acid such as β-mercaptopropionic acid using an aqueous alkali hydrosulfide solution and an unsaturated nitrile such as acrylonitrile.
〔従来の技術及び発明が解決しようとする課題〕水硫化
アルカリ水溶液とアクリロニトリルからのβ−メルカプ
トプロピオン酸の製造法としては特開昭５８−１９８４
６０号公報があるが、本発明者らが追試を行ったところ
、原料として使用する水硫化アルカリ水溶液の種類によ
って得られるβ−メルカプトプロピオン酸の収率に大き
な差がでることが明らかとなった。その原因を究明する
ために詳細な検討を実施した結果、本発明を完成するに
至ったものである。[Prior art and problems to be solved by the invention] A method for producing β-mercaptopropionic acid from an aqueous alkali hydrosulfide solution and acrylonitrile is disclosed in JP-A-58-1984.
No. 60, but when the present inventors conducted additional tests, it became clear that there was a large difference in the yield of β-mercaptopropionic acid obtained depending on the type of aqueous alkali hydrosulfide solution used as a raw material. . As a result of conducting detailed studies to investigate the cause, the present invention has been completed.
即ち本発明は、一般式
％式％
（式中Ｒ１，Ｒ２はＨ又はＣＩ〜３のアルキル基、ｎは
０〜３の整数）
で表される不飽和ニトリルを水硫化アルカリ水溶液に加
えて反応させ、中和、加水分解してメルカプトカルボン
酸を製造するに際し、反応促進剤として硫黄化合物を存
在させることを特徴とするメルカプトカルボン酸の製造
法である。That is, in the present invention, an unsaturated nitrile represented by the general formula % (wherein R1 and R2 are H or an alkyl group of CI to 3, and n is an integer of 0 to 3) is added to an aqueous alkali hydrosulfide solution and reacted. This is a method for producing mercaptocarboxylic acid, which is characterized in that a sulfur compound is present as a reaction accelerator when producing mercaptocarboxylic acid by neutralizing and hydrolyzing the mercaptocarboxylic acid.
上記不飽和ニトリルとしては、アクリロニトリル、メタ
クリロニトリル、２−ブテンニトリルベ ３−ブテンニ
トリル、２−ペンテンニトリル、３−ペンテンニトリル
、４−ペンテンニトリル等があげられる。Examples of the unsaturated nitrile include acrylonitrile, methacrylonitrile, 2-butenenitrile, 3-butenenitrile, 2-pentenenitrile, 3-pentenenitrile, 4-pentenenitrile, and the like.
以下本発明について詳細に説明するが、説明を簡単にす
るために不飽和二） ＩＪルとしてアクリロニトリルを
使用してβ−メルカプトプロピオン酸を製造する場合を
代表例として述べる。The present invention will be described in detail below, but to simplify the explanation, a case will be described as a representative example in which β-mercaptopropionic acid is produced using acrylonitrile as the unsaturated compound.
他の不飽和二） ＩＪルについてもアクリロニトリルの
場合と同様に対応するメルカプトカルボン酸を得ること
ができる。With respect to other unsaturated 2) IJ groups, the corresponding mercaptocarboxylic acids can be obtained in the same manner as in the case of acrylonitrile.
上記の如く、本発明者らが特開昭５８−１９８４６０号
について追試を重ねた結果、原料として使用する水硫化
アルカリ水溶液の種類により反応成績が大きく異なり、
得られるβ−メルカプトプロピオン酸の収率に著しい差
が認められた。つまり、高純度の水硫化アルカリ水溶液
を用いて反応を実施した場合は、β−メルカプトプロピ
オン酸の収率は低く、同公報記載の通りの収率を得るこ
とができず、かえって不純物を含有する純度の低い水硫
化アルカリ水溶液を用いて反応を実施した際に、β−メ
ルカプトプロピオン酸の収率が向上する場合のあること
が判明した。As mentioned above, as a result of repeated tests by the present inventors regarding JP-A-58-198460, we found that the reaction results vary greatly depending on the type of aqueous alkali hydrosulfide solution used as a raw material.
A significant difference in the yield of β-mercaptopropionic acid was observed. In other words, when the reaction is carried out using a high-purity aqueous alkali hydrosulfide solution, the yield of β-mercaptopropionic acid is low and the yield as described in the publication cannot be obtained, and instead it contains impurities. It has been found that when the reaction is carried out using an aqueous alkali hydrosulfide solution with low purity, the yield of β-mercaptopropionic acid may be improved.
その原因としては、水硫化アルカリ中に不純物として含
有されている微量成分が反応促進剤としての役割を成し
、β−メルカプトプロピオン酸の生成を促進させている
ものと予想して鋭意検討を重ねた結果、本発明者らは水
硫化アルカリ水溶液とアクリロニトリルからβ−メルカ
プトプロピオン酸を製造するに際し、反応促進剤として
硫黄化合物を存在させることにより、βメルカプトプロ
ピオン酸収率が大幅に向上することを見出したものであ
る。The cause of this is thought to be that trace components contained as impurities in the alkali hydrosulfide act as reaction accelerators, promoting the production of β-mercaptopropionic acid, and we have conducted extensive studies. As a result, the present inventors found that when producing β-mercaptopropionic acid from an aqueous alkali hydrosulfide solution and acrylonitrile, the yield of β-mercaptopropionic acid was significantly improved by the presence of a sulfur compound as a reaction accelerator. This is what I found.
反応は水硫化アルカリ水溶液にアクリロニトリルの如き
不飽和ニトリルを加えて反応させる際に、反応促進剤と
して硫黄化合物を存在させるものであり、反応促進剤で
ある硫黄化合物としては、硫黄、二硫化ナトリウム、三
硫化ナトリウム、四硫化ナトリウム、三硫化ナトリウム
、二硫化カリウム、三硫化カリウム、四硫化カリウム、
三硫化カリウム等があげられる。また、硫黄化合物を存
在させる方法は特に限定されないが、もともと不純物と
して硫黄化合物を含有している純度の低い水硫化アルカ
リはそのまま反応に使用することもできるし、高純度の
水硫化アルカリを用いる場合には、水硫化アルカリ水溶
液に硫黄化合物を添加して溶解させてからでも、また溶
解させなくても反応に用いることができる。存在させる
硫黄化合物の水硫化アルカリに対する比率としては、モ
ル比で０．４％以上、好ましくは０．７％から５％の範
囲が良く、硫黄化合物の量が少ない場合はβ−メルカプ
トプロピオン酸の収率が低く、また５％以上存在させて
もβ−メルカプトプロピオン酸収率向上の効果はうすく
、経済的に不利になる。The reaction involves adding an unsaturated nitrile such as acrylonitrile to an aqueous alkali hydrosulfide solution and causing the reaction, and a sulfur compound is present as a reaction accelerator. Examples of the sulfur compound as a reaction accelerator include sulfur, sodium disulfide, Sodium trisulfide, sodium tetrasulfide, sodium trisulfide, potassium disulfide, potassium trisulfide, potassium tetrasulfide,
Examples include potassium trisulfide. In addition, the method of making the sulfur compound present is not particularly limited, but a low-purity alkali hydrosulfide that originally contains sulfur compounds as impurities can be used as is for the reaction, or when using a high-purity alkali hydrosulfide The sulfur compound can be used in the reaction either after the sulfur compound is added to the aqueous alkali hydrosulfide solution and dissolved, or without dissolving it. The ratio of the sulfur compound to the alkali hydrosulfide is preferably 0.4% or more in terms of molar ratio, preferably in the range of 0.7% to 5%.If the amount of sulfur compound is small, β-mercaptopropionic acid The yield is low, and even if it is present in an amount of 5% or more, the effect of improving the yield of β-mercaptopropionic acid is weak, which is economically disadvantageous.
水硫化アルカリにアクリロニトリルの如き不飽和ニトリ
ルを加える方法としては、不飽和ニトリルを時間をかけ
て徐々に滴下して反応させても良いし、短時間のうちに
添加して反応させても構わないが、徐々に滴下して反応
させた方がメルカプトカルボン酸の収率が良くなるので
、より好ましい。不飽和ニトリル滴下終了後、数時間熟
成反応を行い反応を完了させる。反応温度は２０〜７０
℃であり、温度が低いと反応速度が遅くなるので反応時
間が長くなり生産性を悪くするし、７０℃を超えると対
応するメルカプトカルボン酸の収率が低下する欠点があ
る。To add an unsaturated nitrile such as acrylonitrile to an alkali hydrosulfide, the unsaturated nitrile can be gradually added dropwise over a period of time to cause the reaction, or it can be added over a short period of time to cause the reaction. However, since the yield of mercaptocarboxylic acid is better when the reaction is carried out by gradual addition, it is more preferable. After dropping the unsaturated nitrile, the reaction is aged for several hours to complete the reaction. Reaction temperature is 20-70
℃, and if the temperature is low, the reaction rate will be slow and the reaction time will be long, resulting in poor productivity.If the temperature is higher than 70℃, there is a disadvantage that the yield of the corresponding mercaptocarboxylic acid will decrease.
以上の条件で得られた反応液は、酸性条件下あるいは塩
基性条件下にして加水分解しメルカプトカルボン酸を製
造するのであるが、この場合酸性条件下で加水分解する
際には、熟成終了後の反応液に塩酸、硫酸などの鉱酸を
加えて中和、酸性化して加水分解を行い、塩基性条件下
での加水分解の際には、熟成終了後の反応液に水酸化ナ
トリウム、水酸化カリウムなどの水酸化アルカリを加え
て加水分解を行った後に鉱酸を加えて中和してメルカプ
トカルボン酸を得ることができる。The reaction solution obtained under the above conditions is hydrolyzed under acidic or basic conditions to produce mercaptocarboxylic acid. In this case, when hydrolyzing under acidic conditions, it is necessary to Hydrolysis is carried out by adding mineral acids such as hydrochloric acid and sulfuric acid to the reaction solution to neutralize and acidify it. When hydrolysis is carried out under basic conditions, sodium hydroxide and water are added to the reaction solution after aging. Mercaptocarboxylic acid can be obtained by adding an alkali hydroxide such as potassium oxide to perform hydrolysis and then adding a mineral acid to neutralize it.
高速液体クロマトグラフィーによる分析によれば、硫黄
化合物を含有しない高純度の水硫化アルカリ水溶液を用
いて反応を行う場合には、メルカプトカルボン酸は３０
〜４０％の収率でしか生成しないのに比べて、硫黄化合
物を存在させて反応を行う場合には７０％以上の高収率
でメルカプトカルボン酸が生成することが明らかになっ
た。According to analysis by high performance liquid chromatography, mercaptocarboxylic acid has a concentration of 30
It has been revealed that mercaptocarboxylic acid is produced in a high yield of 70% or more when the reaction is carried out in the presence of a sulfur compound, whereas the mercaptocarboxylic acid is produced in a yield of only ~40%.
次に実施例によって本発明を具体的に説明するが、本発
明はこれら実施例に何ら限定されるものではない。EXAMPLES Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
２６％水酸化ナトＩＪウム水溶液３０３．０ｇにＩＩ、
Ｓガスを吹き込み、吸収反応させて、３０％水硫化アル
カリ水溶液３７０．０ｇ（ＮａＳＨ１，９７％ル）を合
成した。得られた水硫化アルカリ水溶液に粉末硫黄１、
０ｇ （０，０３１モル）を加えて、溶液を７０℃に加
熱して硫黄を完全に溶解した。次に、この溶液の温度を
４５℃に保ちながらアクリロニ） ＩＪル９５．４ｇ（
１，８モル）を２時間かけて全量滴下し、その後２時間
同温度に保つことによって反応を行った。Example 1 II to 303.0 g of 26% sodium hydroxide aqueous solution,
S gas was blown into the reactor to cause an absorption reaction, and 370.0 g of a 30% aqueous alkali hydrosulfide solution (1,97% NaSH) was synthesized. Powdered sulfur 1,
0 g (0,031 mol) was added and the solution was heated to 70° C. to completely dissolve the sulfur. Next, while maintaining the temperature of this solution at 45°C, add 95.4 g of acryloni
1.8 mol) was added dropwise over 2 hours, and then the reaction was carried out by keeping the same temperature for 2 hours.
この後３６％塩酸５６０ｇ、水１５０ｇを加え、温度１
０６〜１１０℃で６時間還流状態に保ち、加水分解反応
を終了させた。反応液を高速液体クロマトグラフィーで
分析したところ、７５％の収率でβ−メルカプトプロピ
オン酸が生成していた。After this, 560 g of 36% hydrochloric acid and 150 g of water were added, and the temperature was 1.
The mixture was kept under reflux at 06-110°C for 6 hours to complete the hydrolysis reaction. Analysis of the reaction solution by high performance liquid chromatography revealed that β-mercaptopropionic acid was produced in a yield of 75%.
比較例１
２６％水酸化す） ＩＪウム水溶液３０３、ＯｇにＨ２
ｓガスを吹き込み、吸収反応させて、３０％水硫化ナト
リウム水溶液３７０゜Ｏｇを合成した。この溶液の温度
を４５℃に保ちながらアクリロニトリル９５．４ｇを２
時間かけて全量滴下し、以下実施例１と同様の手順で反
応を実施し、得られた反応液を高速液体クロマトグラフ
ィーで分析した結果、３３％の収率でβ−メルカプトプ
ロピオン酸が生成していた。Comparative Example 1 26% hydroxide) IJum aqueous solution 303, Og and H2
S gas was blown into the reactor to cause an absorption reaction to synthesize a 30% aqueous solution of sodium hydrogen sulfide at 370°Og. While maintaining the temperature of this solution at 45°C, add 95.4 g of acrylonitrile to 2
The entire amount was added dropwise over a period of time, the reaction was carried out in the same manner as in Example 1, and the resulting reaction solution was analyzed by high performance liquid chromatography. As a result, β-mercaptopropionic acid was produced with a yield of 33%. was.
出願人代理人 古 谷 馨Applicant's agent Kaoru Furutani
Claims (1)
ル基、ｎは０〜３の整数） で表される不飽和ニトリルを水硫化アルカリ水溶液に加
えて反応させ、中和、加水分解してメルカプトカルボン
酸を製造するに際し、反応促進剤として硫黄化合物を存
在させることを特徴とするメルカプトカルボン酸の製造
法。[Claims] Represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. A method for producing mercaptocarboxylic acid, which comprises adding an unsaturated nitrile to an aqueous alkali hydrosulfide solution, reacting it, neutralizing it, and hydrolyzing it to produce mercaptocarboxylic acid, in which a sulfur compound is present as a reaction accelerator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63272654A JPH02121962A (en) | 1988-10-28 | 1988-10-28 | Production of mercaptocarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63272654A JPH02121962A (en) | 1988-10-28 | 1988-10-28 | Production of mercaptocarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02121962A true JPH02121962A (en) | 1990-05-09 |
Family
ID=17516935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63272654A Pending JPH02121962A (en) | 1988-10-28 | 1988-10-28 | Production of mercaptocarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02121962A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013076968A1 (en) | 2011-11-21 | 2013-05-30 | 三井化学株式会社 | METHOD FOR PRODUCING β-MERCAPTOCARBOXYLIC ACID |
| WO2013076969A1 (en) | 2011-11-21 | 2013-05-30 | 三井化学株式会社 | METHOD FOR PRODUCING β-MERCAPTOCARBOXYLIC ACID |
| WO2013112028A1 (en) * | 2012-01-27 | 2013-08-01 | 주식회사 케이오씨솔루션 | Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials |
| CN105198781A (en) * | 2015-09-10 | 2015-12-30 | 山西其右建材科技有限公司 | Method of treating solid waste produced in beta-mercaptopropionic acid production process |
-
1988
- 1988-10-28 JP JP63272654A patent/JPH02121962A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013076968A1 (en) | 2011-11-21 | 2013-05-30 | 三井化学株式会社 | METHOD FOR PRODUCING β-MERCAPTOCARBOXYLIC ACID |
| WO2013076969A1 (en) | 2011-11-21 | 2013-05-30 | 三井化学株式会社 | METHOD FOR PRODUCING β-MERCAPTOCARBOXYLIC ACID |
| KR20140084309A (en) | 2011-11-21 | 2014-07-04 | 미쓰이 가가쿠 가부시키가이샤 | Production method of? -mercaptocarboxylic acid |
| CN103946211A (en) * | 2011-11-21 | 2014-07-23 | 三井化学株式会社 | Method for producing beta-mercaptocarboxylic acid |
| CN103946210A (en) * | 2011-11-21 | 2014-07-23 | 三井化学株式会社 | Method for producing beta-mercaptocarboxylic acid |
| JP5636510B2 (en) * | 2011-11-21 | 2014-12-03 | 三井化学株式会社 | Process for producing β-mercaptocarboxylic acid |
| JPWO2013076969A1 (en) * | 2011-11-21 | 2015-04-27 | 三井化学株式会社 | Process for producing β-mercaptocarboxylic acid |
| US9133112B2 (en) | 2011-11-21 | 2015-09-15 | Mitsui Chemicals, Inc. | Process for preparing β-mercaptocarboxylic acid |
| US9206119B2 (en) | 2011-11-21 | 2015-12-08 | Mitsui Chemicals Inc. | Process for preparing β-mercaptocarboxylic acid |
| WO2013112028A1 (en) * | 2012-01-27 | 2013-08-01 | 주식회사 케이오씨솔루션 | Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials |
| CN104053646A (en) * | 2012-01-27 | 2014-09-17 | 可奥熙搜路司有限公司 | Method for producing 3-mercaptopropionic acid, and carbonic acid ester composition having mercapto group using same, and method for producing thiourethane-based optical materials |
| CN105198781A (en) * | 2015-09-10 | 2015-12-30 | 山西其右建材科技有限公司 | Method of treating solid waste produced in beta-mercaptopropionic acid production process |
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