JPS5919100B2 - Method for producing 3,5-diamino-1,2,4-triazole sulfate - Google Patents
Method for producing 3,5-diamino-1,2,4-triazole sulfateInfo
- Publication number
- JPS5919100B2 JPS5919100B2 JP9227674A JP9227674A JPS5919100B2 JP S5919100 B2 JPS5919100 B2 JP S5919100B2 JP 9227674 A JP9227674 A JP 9227674A JP 9227674 A JP9227674 A JP 9227674A JP S5919100 B2 JPS5919100 B2 JP S5919100B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- hydrazine
- mol
- sulfate
- diamino
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RYTIYGVHKPCJDX-UHFFFAOYSA-N sulfuric acid;1h-1,2,4-triazole-3,5-diamine Chemical compound OS(O)(=O)=O.NC1=NNC(N)=N1 RYTIYGVHKPCJDX-UHFFFAOYSA-N 0.000 title description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 11
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- -1 triazole sulfate Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 4
- 239000012493 hydrazine sulfate Substances 0.000 description 4
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 4
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- 241000594009 Phoxinus phoxinus Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
【発明の詳細な説明】
本発明は、一般式
ＨＮ−ＮＨト
Ｈ２Ｎ−ＣＣ−ＮＨ２・ ＨＣｌ＋ ＮＨ２−（＼ ／
＊ ２ＮＨ２ＮＨ２・ Ｈ２ＳＯ４・ ２ＨＣＩで表わ
されるヒドラジン酸性塩とジシアンジアミドとを反応さ
せることを特徴とする３・５−ジア、 ミノー１ ・
２ ・ ４−トリアゾール硫酸塩の製造法に関する。[Detailed Description of the Invention] The present invention provides the general formula HN-NHtH2N-CC-NH2.HCl+ NH2-(\ /
* 3,5-dia, minnow 1, which is characterized by reacting a hydrazine acid salt represented by 2NH2NH2・H2SO4・2HCI with dicyandiamide.
2. Relating to a method for producing 4-triazole sulfate.
従来３・５−ジアミノーｌ ・ ２ ・ ４−トリアゾ
ール（以下グアナゾールと称する）の製造法としてはヒ
ドラジン２塩酸塩とジシアンジアミドとを０反応させる
方法が知られている。Conventionally, as a method for producing 3,5-diaminol.2.4-triazole (hereinafter referred to as guanazole), a method in which hydrazine dihydrochloride and dicyandiamide are reacted is known.
（米国特許第２６４８６７１号明細書参照）。しかしな
がらこの従来方法は反応仕込組成中のヒドラジン分とし
て９％以上の含有濃度に於て初めて６５〜７０％のグア
ナゾールを取得出来るも５ のであり（６％の場合は収
率１５％）、高収率を得るためには高濃度のヒドラジン
を用いるか若しくはヒドラジン２塩酸塩にした後水の濃
縮を必要とした。(See US Pat. No. 2,648,671). However, in this conventional method, 65-70% guanazole can only be obtained when the hydrazine content in the reaction charge composition is 9% or more (yield is 15% in the case of 6%), resulting in a high yield. In order to obtain a high concentration of hydrazine, it was necessary to use a high concentration of hydrazine or to concentrate the water after conversion to hydrazine dihydrochloride.
またヒドラジン２塩酸塩は水に易溶性の性質を有しジシ
アンジアミドとの反応に於て、発０熱反応であることか
ら分割投入方式に於ても温度の匍脚が難カルくかつ反応
時間も長時間を要する。即ち、反応温度が５０℃以上か
または必要以上の時間を要した場合は副反応物としてグ
アニル尿素、下記に示すグアナゾグアナゾール等（水に
難溶性）、６の生成がいちじるしく目的生成物の収率が
低下する欠点を有していた。ＮＨＣＮ→ＨＮ（ｌ）ＮＨ
＋Ｎｏ、。In addition, hydrazine dihydrochloride has the property of being easily soluble in water, and the reaction with dicyandiamide is a zero exothermic reaction, making it difficult to control the temperature and shorten the reaction time even in the split-input method. It takes a long time. That is, if the reaction temperature is 50°C or higher or if a longer time than necessary, the formation of guanylurea, guanazoguanazole (poorly soluble in water), etc. shown below as a side reaction product, and the formation of the desired product (6) is significant. It had the disadvantage of lower yield. NHCN→HN(l)NH
+No.
Ｃｌさらに上記した方法は反応終了後生成物を取得する
にも塩酸グアナゾールが水に易溶性であることからそれ
をいつたん遊離化させた後減圧濃縮して乾固させ、次い
で大量の熱メタノールにて抽出した後さらに減圧濃縮し
目的のグアナゾールを取得しなければならず極めて煩雑
な後処理を行なわ）なければならなかつた。Furthermore, in the above method, to obtain the product after the reaction is completed, since guanazole hydrochloride is easily soluble in water, it is first liberated and then concentrated under reduced pressure to dryness, and then poured into a large amount of hot methanol. After extraction, the desired guanazole had to be further concentrated under reduced pressure, requiring extremely complicated post-treatment.
本発明者等はこれら従来法に於ける欠点を解決すべく種
種研究を重ねた結果下記に示すような本発明方法によれ
ば極めて簡単にグアナゾール類を取得し得ることを見出
した。The inventors of the present invention have repeatedly conducted various studies to solve the drawbacks of these conventional methods, and have found that guanazoles can be obtained extremely easily by the method of the present invention as shown below.
すなわち本発明方法は混酸のヒドラジン酸性塩とジシア
ンジアミドとを反応させるものであるが本発明方法によ
ればヒドラジン２塩酸塩の場合に比べて反応が緩慢なた
め反応温度の制御が容易であり、かつ反応温度も４０〜
７０℃好ましくは５０〜６５℃で実施することができ目
的生成物も極めて高収率で得ることができる。That is, the method of the present invention involves reacting the mixed acid hydrazine acid salt with dicyandiamide, but according to the method of the present invention, the reaction temperature is easier to control because the reaction is slower than in the case of hydrazine dihydrochloride. The reaction temperature is also 40~
The reaction can be carried out at 70°C, preferably from 50 to 65°C, and the desired product can be obtained in extremely high yield.
また本発明方法によれば反応終了後単に反応液を冷却す
ることによつて簡単に生成物であるグアＫナゾール硫酸
塩を収得することが出来るので従来法のような煩雑な後
処理工程をまつたく必要としない利点を有し反応終了後
生成物を取得した後の反応母液は次の反応の反応液とし
て用いることによつて本発明方法を効果的に実施するこ
とが出来る。Furthermore, according to the method of the present invention, the product, guar Knazole sulfate, can be easily obtained by simply cooling the reaction solution after the reaction is completed, thereby avoiding the complicated post-treatment steps required in conventional methods. The method of the present invention can be carried out effectively by using the reaction mother liquor after obtaining the product after the completion of the reaction as a reaction solution for the next reaction.
本発明方法に用いられるヒドラジン酸性塩は例えば下記
式に示す方法により取得することができる。The hydrazine acid salt used in the method of the present invention can be obtained, for example, by the method shown in the following formula.
次に本発明をさらに具体的に説明するために実施例をあ
げるが本発明は以下の実施例に限定されるものではない
。EXAMPLES Next, Examples will be given to explain the present invention more specifically, but the present invention is not limited to the following Examples.
実施例 １
１０００ＣＣの３頚フラスコに効率の良（・撹拌子およ
び温度計を附して２０％ヒドラジンヒトラード２５０Ｖ
（ １．０モル）を仕込み水浴下内温３０℃以下に保ち
つつ酸性硫酸ヒドラジン１３０，（ １．０モル）を徐
徐に加えＰＨ６．Ｏに調整して中性塩である硫酸ヒドラ
ジンとする、この水溶液中に３５％塩酸を２０８Ｖ（
２．０モル）を上記内温で滴加し硫酸、塩酸からなる混
酸のヒドラジン酸性塩とした後ジシアンジアミド１６８
，（２．０モル）を内温６０℃に保ちつつ同温温で４時
間反応を行ない完結させる。Example 1 A 1000CC 3-necked flask with high efficiency (with a stirrer and thermometer, 20% hydrazine hydrogen at 250V)
(1.0 mol) was prepared, and while keeping the internal temperature below 30°C in a water bath, slowly added acidic hydrazine sulfate 130, (1.0 mol) to pH 6. In this aqueous solution, add 35% hydrochloric acid at 208 V (
2.0 mol) was added dropwise at the above internal temperature to form a hydrazine acid salt of a mixed acid consisting of sulfuric acid and hydrochloric acid, and then dicyandiamide 168
, (2.0 mol) at the same temperature for 4 hours while maintaining the internal temperature at 60°C to complete the reaction.
次いで直ちに冷却を始め内温１５℃で結晶を充分に析出
させこのものを遠心沢過し、冷水（５℃）で２回洗滌を
行なつた後乾燥して３・５ジアミノ−１ ・ ２ ・
４ −トリアゾール硫酸塩１６９Ｖ（純度９２％、収率
５７％）を得る。なおこの場合の反応組成中のヒドラジ
ノ濃度８．５％である。Immediately, cooling was started to sufficiently precipitate crystals at an internal temperature of 15°C, which was centrifugally filtered, washed twice with cold water (5°C), and then dried to give 3.5 diamino-1, 2, and
4-triazole sulfate 169V (purity 92%, yield 57%) is obtained. In this case, the hydrazino concentration in the reaction composition was 8.5%.
実施例 ２
実施例１によつて得られた反応母液（ヒドラジン分含有
量２．３％）５５３ｙのＨ容量を反応装置に仕込み続い
て８０％ヒドラジンヒトラード２５？（０．４モル）を
加え水浴下内温３０℃以下に保ちつつ酸性硫酸ヒドラジ
ン５２７（０．４モル）を徐徐に加えＰＨ６．Ｏに調整
する。Example 2 A reaction mother liquor (hydrazine content 2.3%) obtained in Example 1 with an H capacity of 553y was charged into a reactor, and then 80% hydrazine hydrogen was added to the reactor. (0.4 mol) was added, and while keeping the internal temperature under the water bath at 30°C or less, acidic hydrazine sulfate 527 (0.4 mol) was gradually added to pH 6. Adjust to O.
この水溶液中に３５゛％塩酸を１０４ｔ（１．０モル）
を上記内温を３０℃以下に保持しながら滴加し硫酸、塩
酸からなる混酸のヒドラジン酸性塩とした後ジシアンジ
アミド８４７（１．０モル）を内温６０℃に保ちつつ反
応を行ない同温度で４時間反応させる。次いで直ちに冷
却を始め内温１５℃で結晶を充分に析出させ遠心沢過し
、冷水（５℃）で２回洗滌を行なつた後乾燥して３・５
−ジアミノ−１・２・４トリアゾール硫酸塩１２６ｙ（
純度８８％、収率８５％）を得る。本例の反応組成物中
のヒドラジン濃度は８．９％である。なお再結晶は水を
用いて行ない純度９８．５％の目的生成物を取得した（
収率９５％）。In this aqueous solution, 104t (1.0 mol) of 35% hydrochloric acid was added.
was added dropwise while keeping the internal temperature below 30°C to form a hydrazine acid salt of a mixed acid consisting of sulfuric acid and hydrochloric acid, and then reacted with dicyandiamide 847 (1.0 mol) while keeping the internal temperature at 60°C. Allow to react for 4 hours. Immediately, cooling was started to sufficiently precipitate the crystals at an internal temperature of 15°C, followed by centrifugal filtration, washing twice with cold water (5°C), and drying.
-diamino-1,2,4 triazole sulfate 126y (
Purity: 88%, yield: 85%). The hydrazine concentration in the reaction composition of this example is 8.9%. The recrystallization was performed using water and the desired product with a purity of 98.5% was obtained (
yield 95%).
実施例 ３
１０００ＣＣの３頚フラスコに効率の良い攪拌子および
温度計を附して８０％ヒドラジンヒトラード１２５ｙ（
２．０モル）を仕込み水浴下内温３０℃以下に保ちつつ
６０％硫酸１６５ク（１．０モル）を徐徐に加えＰＨ６
．Ｏに調整して中性塩である硫酸ヒドラジンとする。Example 3 A 1000CC 3-necked flask was equipped with an efficient stirrer and a thermometer, and 80% hydrazine Htland 125y (
2.0 mol), and while keeping the internal temperature below 30°C in a water bath, gradually added 165 ml of 60% sulfuric acid (1.0 mol) to pH 6.
．． Adjust to O to obtain hydrazine sulfate, which is a neutral salt.
この水溶液中に３５％塩酸２０８７（２．０モル）を上
記内温で滴加し硫酸塩酸からなる混酸のヒドラジン酸性
塩とした後ジシアンジアミド１６８７（２．０モル）を
内温６０℃に保ちつつ反応を行ない、同温度で４時間反
応を行ない充結させる。なおこの場合の反応組成物中の
ヒドラジン濃度は９．６％である。以下実施例１と同様
にして処理を行なうと３・５−ジアミノ−１・２・４−
トリアゾール硫酸塩１６３ｔ（純度９２．５％、収率５
５％）を得る。To this aqueous solution, 35% hydrochloric acid 2087 (2.0 mol) was added dropwise at the above internal temperature to form a hydrazine acid salt of a mixed acid consisting of sulfuric acid, and then dicyandiamide 1687 (2.0 mol) was added while maintaining the internal temperature at 60°C. The reaction is carried out at the same temperature for 4 hours to complete the reaction. Note that the hydrazine concentration in the reaction composition in this case was 9.6%. Hereinafter, when the treatment is carried out in the same manner as in Example 1, 3,5-diamino-1,2,4-
Triazole sulfate 163t (purity 92.5%, yield 5
5%).
比較例撹拌機、温度計を付けた１０００ＣＣの３頚フラ
スコに、水２５０ＣＣと酸性硫酸ヒドラジン（Ｈ２Ｎ−
ＮＨ２・Ｈ２ＳＯ４） １３０７（１．０モル）とを添
加した。Comparative Example In a 1000 cc three-necked flask equipped with a stirrer and a thermometer, 250 cc of water and acidic hydrazine sulfate (H2N-
NH2.H2SO4) 1307 (1.0 mol) was added.
内温を４５〜５０℃に維持しつつジシアンジアミド８４
７（１．０モル）を添加して２時間反応させた。Dicyandiamide 84 while maintaining the internal temperature at 45-50℃
7 (1.0 mol) was added and reacted for 2 hours.
この場合の反応組成中のヒドラジン濃度は６，９％であ
る。冷却後か性ソーダ２モル水溶液２００ＣＣで中和し
てグアナゾール遊離し、Ｍｔ・％Ｈ２ＳＯ４をＮａ２ｓ
Ｏ４に変えた。The hydrazine concentration in the reaction composition in this case is 6.9%. After cooling, it was neutralized with 200 cc of a 2 molar aqueous solution of caustic soda to liberate guanazole, and the Mt%H2SO4 was converted to Na2s.
Changed to O4.
常温で減圧濃度、乾操後、１，５１沸騰メタノールでグ
アナゾールを抽出し、このメタノール溶液をエバポレー
ターで濃縮、冷却、沢過、乾燥して、３・５−ジアミノ
−１・２・４−トリアゾール１１．９ク（純度９０％、
収率１２％）を得た。水の添加量５００ＣＣ（ヒドラジ
ン濃度４．５％）、反応時間を４時間とした以外は前記
例と同様な条件で反応を行なうと純度９１％、収率１３
％で目的物が得られる。After concentration under reduced pressure at room temperature and drying, guanazole is extracted with 1,51 boiling methanol, and this methanol solution is concentrated in an evaporator, cooled, filtered, and dried to obtain 3,5-diamino-1,2,4-triazole. 11.9k (90% purity,
A yield of 12%) was obtained. When the reaction was carried out under the same conditions as in the previous example except that the amount of water added was 500 cc (hydrazine concentration 4.5%) and the reaction time was 4 hours, the purity was 91% and the yield was 13.
The desired product can be obtained in %.
更に反応温度を７０℃または９０℃とした以外は前記例
と同様に反応を行なうとそれぞれ純度７３％、収率１８
％および純度６１％、収率２１％で目的物を得ることが
できる。Further, when the reaction was carried out in the same manner as in the above example except that the reaction temperature was changed to 70°C or 90°C, the purity was 73% and the yield was 18%.
The target product can be obtained with a purity of 61% and a yield of 21%.
Claims (1)
されるヒドラジン酸性塩とジシアンジアミドとを反応さ
せることを特徴とする３・５−ジアミノ−１・２・４−
トリアゾール硫酸塩の製造法。[Claims] 1. 3,5-diamino-1,2,4-, which is characterized by reacting a hydrazine acid salt represented by the general formula 2NH_2NH_2·H_2SO_4·2HCl with dicyandiamide.
Method for producing triazole sulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9227674A JPS5919100B2 (en) | 1974-08-14 | 1974-08-14 | Method for producing 3,5-diamino-1,2,4-triazole sulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9227674A JPS5919100B2 (en) | 1974-08-14 | 1974-08-14 | Method for producing 3,5-diamino-1,2,4-triazole sulfate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5123266A JPS5123266A (en) | 1976-02-24 |
| JPS5919100B2 true JPS5919100B2 (en) | 1984-05-02 |
Family
ID=14049865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9227674A Expired JPS5919100B2 (en) | 1974-08-14 | 1974-08-14 | Method for producing 3,5-diamino-1,2,4-triazole sulfate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5919100B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357395A (en) * | 1980-08-22 | 1982-11-02 | General Electric Company | Transfer lamination of vapor deposited foils, method and product |
| DE3510202A1 (en) * | 1985-03-21 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | ELECTRICAL BOARDS |
-
1974
- 1974-08-14 JP JP9227674A patent/JPS5919100B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5123266A (en) | 1976-02-24 |
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