JPH0544457B2 - - Google Patents
Info
- Publication number
- JPH0544457B2 JPH0544457B2 JP269284A JP269284A JPH0544457B2 JP H0544457 B2 JPH0544457 B2 JP H0544457B2 JP 269284 A JP269284 A JP 269284A JP 269284 A JP269284 A JP 269284A JP H0544457 B2 JPH0544457 B2 JP H0544457B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- glycinonitrile
- hydantoin
- acid
- ammonium bicarbonate
- 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 - Lifetime
Links
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 19
- 239000001099 ammonium carbonate Substances 0.000 claims description 19
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 15
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 13
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 11
- 229940091173 hydantoin Drugs 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- 239000004471 Glycine Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 description 5
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000006150 Bucherer-Bergs reaction Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- -1 cyanide compound Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は、ヒダントインの製造法に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing hydantoin.
従来ヒダントインの製造方法としては、ホルム
アルデヒド、シアン化合物、および（重）炭酸ア
ンモニウムを常圧下、水または水性アルコール溶
媒中で反応させるBucherer−Bergs反応が知られ
ている。しかしこの方法は、非常に困難であり、
その後種々の改良法が報告されている。 As a conventional method for producing hydantoin, the Bucherer-Bergs reaction is known in which formaldehyde, a cyanide compound, and ammonium (bi)carbonate are reacted in water or an aqueous alcoholic solvent under normal pressure. However, this method is extremely difficult and
Since then, various improved methods have been reported.
例えば、グリコロニトリルと重炭酸アンモニウ
ムを密閉加圧下に反応させた後、酸処理を行う方
法（特公昭39−24807）。グリコロニトリルと重炭
酸アンモニウムを常圧下第２アミン又は第３アミ
ンの存在下反応させる方法（特公昭50−671）。ま
た、グリコロニトリルと重炭酸アンモニウムを水
性アルコキシエタノール類と水を溶媒として用い
反応させる方法（特開昭54−138557）等がある。 For example, a method in which glycolonitrile and ammonium bicarbonate are reacted under closed pressure and then treated with acid (Japanese Patent Publication No. 39-24807). A method of reacting glycolonitrile and ammonium bicarbonate under normal pressure in the presence of a secondary or tertiary amine (Japanese Patent Publication No. 50-671). There is also a method in which glycolonitrile and ammonium bicarbonate are reacted with aqueous alkoxyethanol using water as a solvent (Japanese Patent Application Laid-Open No. 138557/1983).
しかし、これらの方法は、例えば、反応生成物
の着色が著るしい、グリコロニトリルは特に不安
定であり、この分解が着色の原因にもなつてい
る、密閉加圧下に反応を行うためには耐圧設備を
用いる必要がある、などの操作上及び設備上の問
題点があつた。 However, in these methods, for example, the coloring of the reaction product is significant, glycolonitrile is particularly unstable, and this decomposition is a cause of coloration, and the reaction is carried out under closed pressure. There were operational and equipment problems such as the need to use pressure-resistant equipment.
また、他の方法としてグリシンエチルエステル
塩酸塩とシアン酸塩との反応（Chem.Ber.333418
（1900））、グリシンとシアン酸塩との反応（J.
Chem.Soc.192679）、およびグリシンと尿素との
反応（Chem.Ber.412953（1908））等が知られてい
るが、原料のグリシンやグリシンエチルエステル
塩酸塩及びシアン酸塩等が高価であるという問題
がある。 Another method is the reaction of glycine ethyl ester hydrochloride with cyanate (Chem.Ber. 33 3418
(1900)), the reaction of glycine with cyanate (J.
Chem.Soc. 1926 79) and the reaction between glycine and urea (Chem.Ber. 41 2953 (1908)), etc., but the raw materials such as glycine, glycine ethyl ester hydrochloride and cyanate are expensive. There is a problem that.
本発明者らはこのような問題点を克服するため
種々検討した結果、グリシノニトリルと重炭酸ア
ンモン、炭酸アンモンもしくはアンモニアと２酸
化炭素またはこれらの混合物を水または水性溶媒
中で、常圧下に反応させた後酸処理をすることに
より、収率よくヒダントインを製造することがで
きることを見いだした。 As a result of various studies to overcome these problems, the present inventors found that glycinonitrile and ammonium bicarbonate, ammonium carbonate or ammonia and carbon dioxide, or a mixture thereof, were mixed in water or an aqueous solvent under normal pressure. It has been found that hydantoin can be produced in good yield by performing an acid treatment after the reaction.
因みに、グリシノニトリルと重炭酸アンモン、
炭酸アンモンまたはアンモニアと２酸化炭素との
反応によりヒダントインを製造した例は従来公知
の文献、特許等には未だ見あたらない。 By the way, glycinonitrile and ammonium bicarbonate,
No examples of producing hydantoin by the reaction of ammonium carbonate or ammonia with carbon dioxide have been found in any conventionally known literature or patents.
本発明は、グリシノニトリルと重炭酸アンモ
ン、炭酸アンモンもしくはアンモニアと２酸化炭
素またはこれらの混合物を水または水性溶媒中常
圧下で反応させた後硫酸あるいは塩酸を添加し加
熱処理することを特徴とするヒダントインの製造
方法を提供せんとするものであるが、本発明にお
いて、原料として使用できるグリシノニトリル
は、例えば、ホルムアルデヒド、青酸、アンモニ
アより工業的に製造することができ、精製品、粗
製品、およびグリシノニトリル硫酸塩をアルカリ
で中和し、遊離させたもの等である。 The present invention is characterized in that glycinonitrile and ammonium bicarbonate, ammonium carbonate or ammonia and carbon dioxide, or a mixture thereof are reacted in water or an aqueous solvent under normal pressure, and then sulfuric acid or hydrochloric acid is added and heat treated. Although it is intended to provide a method for producing hydantoin, glycinonitrile that can be used as a raw material in the present invention can be industrially produced from, for example, formaldehyde, hydrocyanic acid, and ammonia, and can be used as a purified product, a crude product, and those obtained by neutralizing glycinonitrile sulfate with an alkali and liberating it.
また重炭酸アンモン、炭酸アンモンまたは炭酸
ガスとアンモニアいずれでも良く、これらの混合
物を使用することもできる。 Further, any of ammonium bicarbonate, ammonium carbonate, carbon dioxide gas and ammonia may be used, and a mixture thereof may also be used.
また水と併用することのできる親水性有機溶媒
として、メタノール、エタノール、ジオキサン、
テトラヒドロフラン、グリセリン、エチレングリ
コール、イソプロパノール、ｎ−プロパノール等
が挙げられる。 Hydrophilic organic solvents that can be used in combination with water include methanol, ethanol, dioxane,
Examples include tetrahydrofuran, glycerin, ethylene glycol, isopropanol, n-propanol, and the like.
重炭酸アンモン等は必ずしも制限はないが一般
に、グリシノニトリルに対し1.0〜3.0倍モル用い
ることが望ましい。モル比を多くするとコスト高
となり、また収率もあまり向上しない。反応混合
物中のグリシノニトリル濃度は５〜30wt％程度
が適当である。 Ammonium bicarbonate and the like are not necessarily limited, but it is generally desirable to use them in an amount of 1.0 to 3.0 times the molar amount of glycinonitrile. If the molar ratio is increased, the cost will increase and the yield will not improve much. The appropriate concentration of glycinonitrile in the reaction mixture is about 5 to 30 wt%.
反応温度についても厳密な制限はないが、45〜
80℃で行うことが好ましく反応時間は、２〜10時
間程度である。反応温度が低いと反応時間が長く
なる。また反応時間が高すぎると重炭酸アンモニ
ウムの飛散が起り好ましくない。 There is no strict limit on the reaction temperature, but it is 45~
It is preferable to carry out the reaction at 80°C, and the reaction time is about 2 to 10 hours. The lower the reaction temperature, the longer the reaction time. Moreover, if the reaction time is too long, ammonium bicarbonate will scatter, which is undesirable.
反応後副生したヒダントイン誘導体を環化させ
るため濃硫酸あるいは濃塩酸を、使用したグリシ
ノニトリルに対し３〜５当量比加え酸処理を行
う。酸処理の条件は特別な制限ではないが、温度
は80〜110℃で、時間は１時間位である。 In order to cyclize the hydantoin derivative produced as a by-product after the reaction, acid treatment is performed by adding concentrated sulfuric acid or concentrated hydrochloric acid in an equivalent ratio of 3 to 5 to the glycinonitrile used. The acid treatment conditions are not particularly limited, but the temperature is 80 to 110°C and the time is about 1 hour.
次に本発明を実施例により詳細に説明する。た
だし、これは説明のための例示であり、本発明を
何ら制限するものではないことは言うまでもな
い。なお収率は仕込グリシノニトリルに対するも
のである。 Next, the present invention will be explained in detail with reference to examples. However, it goes without saying that this is an example for explanation and does not limit the present invention in any way. Note that the yield is based on the charged glycinonitrile.
実施例 １
500mlセパラブルフラスコに玉入冷却管、温度
計、メカニカルスターラーを備える。Example 1 A 500ml separable flask was equipped with a ball cooling tube, a thermometer, and a mechanical stirrer.
フラスコに水147ｇ、40wt％グリシノニトリル
水溶液140ｇおよび重炭酸アンモニウム158ｇを入
れ、75℃に加熱し３時間反応させた。 147 g of water, 140 g of a 40 wt% aqueous glycinonitrile solution, and 158 g of ammonium bicarbonate were placed in a flask, heated to 75° C., and reacted for 3 hours.
次いでこの反応液に95wt％濃硫酸225ｇを発泡
に注意して50℃以下に保ちながら加えた。これを
105℃に加熱し、１時間加熱処理をした。この反
応液を高速液体クロマトグラフ（カラムShodex
Ion pak Ｃ−811溶離液0.4wt％HClO4、カラム
Shodex OH pak Ｂ−804溶離液0.05wt％
H3PO4）で分析したところ液中収率でヒダント
イン74％、ヒダントイン酸２％、グリシン10％が
得られた。 Next, 225 g of 95 wt % concentrated sulfuric acid was added to this reaction solution while being careful to prevent foaming and keeping the temperature below 50°C. this
It was heated to 105°C and heat treated for 1 hour. This reaction solution was analyzed using a high-performance liquid chromatograph (column Shodex).
Ion pak C-811 eluent 0.4wt% HClO 4 , column
Shodex OH pak B-804 eluent 0.05wt%
As a result of analysis using H 3 PO 4 ), 74% hydantoin, 2% hydantoic acid, and 10% glycine were obtained in liquid yield.
実施例 ２
実施例１と同装置を備えた500mlセパラブルフ
ラスコに、40wt％グリシノニトリル水溶液を140
ｇ、重炭酸アンモニウムを197.5ｇ仕込む。75℃
に加熱し３時間反応させた。Example 2 In a 500 ml separable flask equipped with the same equipment as in Example 1, 140% of a 40 wt% glycinonitrile aqueous solution was added.
g, and prepare 197.5 g of ammonium bicarbonate. 75℃
The mixture was heated to a temperature of 100.degree. C. and reacted for 3 hours.
次に、95wt％濃硫酸180ｇを、発泡に注意し50
℃以下に保ちながら加えた。そして105℃、１時
間加熱処理を行つた。この液を高速液体クロマト
グラフで分析したところ、液中収率ヒダントイン
74％、ヒダントイン酸２％、グリシン７％が得ら
れた。 Next, add 180 g of 95 wt% concentrated sulfuric acid to 50 g, being careful not to foam.
The mixture was added while keeping the temperature below ℃. Then, heat treatment was performed at 105°C for 1 hour. When this liquid was analyzed by high performance liquid chromatography, the yield of hydantoin in the liquid was found to be
74%, hydantoic acid 2%, and glycine 7%.
実施例 ３
実施例１と同装置を備えた500mlセパラブルフ
ラスコに40wt％グリシノニトリル水溶液140ｇ、
重炭酸アンモニウム158ｇを仕込む。これを55℃
に加熱し10時間反応させた。Example 3 In a 500 ml separable flask equipped with the same equipment as in Example 1, 140 g of a 40 wt% glycinonitrile aqueous solution was added.
Charge 158g of ammonium bicarbonate. This is 55℃
The mixture was heated to a temperature of 100.degree. and reacted for 10 hours.
次に36wt％硫酸354ｇを50℃以下に保ちながら
加えた。そして105℃、１時間加熱処理を行つた。 Next, 354 g of 36 wt% sulfuric acid was added while keeping the temperature below 50°C. Then, heat treatment was performed at 105°C for 1 hour.
この反応液を高速液体クロマトグラフで分析し
たところ液中収率ヒダントイン70％、ヒダントイ
ン酸２％、グリシン６％が得られた。 When this reaction solution was analyzed by high performance liquid chromatography, the yield in the solution was 70% for hydantoin, 2% for hydantoic acid, and 6% for glycine.
実施例 ４
実施例１と同装置を備えた500mlセパラブルフ
ラスコに22wt％アンモニア水150ｇ、グリシノニ
トリル56ｇを仕込み50℃以下で炭酸ガス45を吹
込んだ。その後80℃に加熱し、２時間反応させ
た。Example 4 A 500 ml separable flask equipped with the same equipment as in Example 1 was charged with 150 g of 22 wt% ammonia water and 56 g of glycinonitrile, and 45 g of carbon dioxide gas was blown into the flask at a temperature below 50°C. Thereafter, the mixture was heated to 80°C and reacted for 2 hours.
次に95wt％濃硫酸225ｇを発泡に注意して50℃
以下に保ちながら加えた。これを105℃に加熱し、
１時間加熱処理をした。この反応液を高速液体ク
ロマトグラフで分析したところ、液中収率ヒダン
トイン72％、ヒダントイン酸３％、グリシン８％
が得られた。 Next, add 225g of 95wt% concentrated sulfuric acid at 50°C, being careful not to foam.
I added it while keeping it below. Heat this to 105℃,
Heat treatment was performed for 1 hour. When this reaction solution was analyzed by high performance liquid chromatography, the yield in the solution was 72% for hydantoin, 3% for hydantoic acid, and 8% for glycine.
was gotten.
実施例 ５
実施例１と同装置を備えた500mlセパラブルフ
ラスコに40wt％グリシノニトリル水溶液を140
ｇ、炭酸アンモニウムを188ｇ仕込む。70℃に加
熱し、４時間反応させた。Example 5 A 40 wt% glycinonitrile aqueous solution was added to a 500 ml separable flask equipped with the same equipment as in Example 1.
Prepare 188g of ammonium carbonate. The mixture was heated to 70°C and reacted for 4 hours.
次に、95wt％濃硫酸225ｇを発泡に注意して50
℃以下に保ちながら加えた。これを105℃に加熱
し、１時間加熱処理をした。この反応液を高速液
体クロマトグラフで分析したところ、液中収率ヒ
ダントイン72％、ヒダントイン酸４％、グリシン
８％が得られた。 Next, add 225g of 95wt% concentrated sulfuric acid to 50%
The mixture was added while keeping the temperature below ℃. This was heated to 105°C and heat treated for 1 hour. When this reaction solution was analyzed by high performance liquid chromatography, the yield in the solution was 72% for hydantoin, 4% for hydantoic acid, and 8% for glycine.
Claims (1)
炭酸アンモン、炭酸アンモンもしくはアンモニア
と２酸化炭素またはこれらの混合物を反応させ、
次いで硫酸または塩酸を添加し加熱処理すること
を特徴とするヒダントインの製造方法。1 Reacting glycinonitrile with ammonium bicarbonate, ammonium carbonate or ammonia with carbon dioxide or a mixture thereof in water or an aqueous solvent,
A method for producing hydantoin, which comprises then adding sulfuric acid or hydrochloric acid and heat-treating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP269284A JPS60146876A (en) | 1984-01-12 | 1984-01-12 | Production of hydantoin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP269284A JPS60146876A (en) | 1984-01-12 | 1984-01-12 | Production of hydantoin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60146876A JPS60146876A (en) | 1985-08-02 |
| JPH0544457B2 true JPH0544457B2 (en) | 1993-07-06 |
Family
ID=11536326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP269284A Granted JPS60146876A (en) | 1984-01-12 | 1984-01-12 | Production of hydantoin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60146876A (en) |
-
1984
- 1984-01-12 JP JP269284A patent/JPS60146876A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60146876A (en) | 1985-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |