DE2112398A1 - Carbohydrazide prepn - from hydrazine(hydrate) and urea or semicarbazide (salt) - Google Patents
Carbohydrazide prepn - from hydrazine(hydrate) and urea or semicarbazide (salt)Info
- Publication number
- DE2112398A1 DE2112398A1 DE19712112398 DE2112398A DE2112398A1 DE 2112398 A1 DE2112398 A1 DE 2112398A1 DE 19712112398 DE19712112398 DE 19712112398 DE 2112398 A DE2112398 A DE 2112398A DE 2112398 A1 DE2112398 A1 DE 2112398A1
- Authority
- DE
- Germany
- Prior art keywords
- carbohydrazide
- semicarbazide
- urea
- hydrazine
- hydrazine hydrate
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 22
- XEVRDFDBXJMZFG-UHFFFAOYSA-N Carbohydrazide Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 title claims abstract description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000004202 carbamide Substances 0.000 title claims abstract description 11
- DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 title description 2
- 239000011780 sodium chloride Substances 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 5
- XHQYBDSXTDXSHY-UHFFFAOYSA-N Semicarbazide hydrochloride Chemical compound Cl.NNC(N)=O XHQYBDSXTDXSHY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003349 semicarbazides Chemical class 0.000 claims abstract description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 2
- 102000037197 Anion exchangers Human genes 0.000 claims 1
- 108091006437 Anion exchangers Proteins 0.000 claims 1
- 238000002844 melting Methods 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
Abstract
Description
Verfahren zur Herstellung von Carbohydrazid Die Erfindung betrifft ein Verfahren zur Herstellung von Carbohydrazid aus Harnstoff oder Semicarbazid oder Semicarbazidsalz. Process for the preparation of carbohydrazide The invention relates to a process for the production of carbohydrazide from urea or semicarbazide or semicarbazide salt.
Oarbohydrazid wird bekanntlich durch Umsetzung von Hydrazin mit Dialkylkarbonaten oder Phosgen hergestellt.Oarbohydrazide is known to be produced by reacting hydrazine with dialkyl carbonates or phosgene produced.
Außerdem ist es nach F. Kurzer u. M. Wilkinson, Chem. Rev. 70, 111 - 149 bekannt, Carbohydrazid durch Erhitzen des Hydrazoniumsalzes der Hydrazinkarbonsäure auf 140 ° C herzustellen. According to F. Kurzer and M. Wilkinson, Chem. Rev. 70, 111-149, it is also known to produce carbohydrazide by heating the hydrazonium salt of hydrazine carboxylic acid to 140.degree.
Es ist weiterhin bekannt, Semicarbazid aus Harnstoff und Hydrazinhydrat herzustellen.It is also known, semicarbazide from urea and hydrazine hydrate to manufacture.
Die Erfindung hat den Zweck, Carbohydrazid in sehr einfacher Weise und unter Verwendung des ungiftigen und preisgünstigen Harnstoffs bzw. des hieraus entstandenen Semicarbazids herzustellen. Außerdem bietet Semicarbazid gegenüber Phosgen den Vorteil der ungefährlichen und einfachen Handhabung.The purpose of the invention is to make carbohydrazide in a very simple manner and using the non-toxic and inexpensive urea or from it to produce the resulting semicarbazids. Also offers semicarbazide opposite Phosgene has the advantage of being safe and easy to use.
Das erfindungsgemäße Verfahren zur Herstellung von Carbohydrazid aus Harnstoff oder Semicarbazid oder Semicarbazidsalz ist dadurch gekennzqlchnet, daß der Ausgangsstoff mit Hydrazinhydrat r oder wasserfreiem Hydrazin unter Rückfluß und Zufuhr von Wärme zur Reaktion gebracht wird. The process according to the invention for the preparation of carbohydrazide from urea or semicarbazide or semicarbazide salt is characterized in that the starting material is reacted with hydrazine hydrate or anhydrous hydrazine under reflux and with the addition of heat.
Nachstehend seien in zwei Beispielen praktische Verfahren zur Herstellung von Carbohydrazid beschrieben.Practical methods of preparation are given below in two examples described by carbohydrazide.
Beispiel 1 240 g Harnstoff und 600 g Hydrazinhydrat wurden 40 Stunden unter Rückfluß gekocht. Es entwickelte sich Ammoniak. Das überschüssl-' ge Hydrazinhydrat wurde zum überwiegenden Teil abdestilliert. Example 1 240 g of urea and 600 g of hydrazine hydrate were used for 40 hours refluxed. Ammonia developed. The excess hydrazine hydrate was for the most part distilled off.
Nach Zugabe von 250 - 300 ml Äthanol und zusätzlichem Schütteln fiel das Carbohydrazid in feiner Form aus und wurde abgesaugt.After adding 250-300 ml of ethanol and additional shaking, it fell the carbohydrazide in fine form and was filtered off with suction.
Die Ausbeute bei diesem Herstellungsverfahren betrug 236 g ^ 65,7 %. Der Schmelzpunkt des auf diese Weise hergestellten Carbo-0 hydrazids lag bei 146 - 149 ° C. Die Ausbeute der Carbohydrazid-Gewinnung konnte bei diesem Herstellungsverfahren durch längeres Kochen oder Verwendung von wasserfreiem Hydrazin auf über 90 % erhöht werden.The yield from this manufacturing process was 236 g ^ 65.7 %. The melting point of the carbo-hydrazide produced in this way was around 146 - 149 ° C. The yield of the carbohydrazide recovery could not be achieved with this manufacturing process increased to over 90% by prolonged boiling or using anhydrous hydrazine will.
Beispiel 2 5,57 go Mol) Semicarbazidhydrochlorid und 7,5 g (203 Mol) Hydrazinhydrat wurden unter Rückfluß 6 Stunden gekocht. Das Uberschüssige'Hydrazin wurde abdestilliert. Der Rückstand wurde in einer genügenden Menge Wasser gelöst und übor oinen Aniononnuatauscher gegeben. Nach dem Abdestitlieren des Wassers wurde das so entstandene Carbohydrazid mit Alkohol verrührt und abgesaugt. Example 2 5.57 g mol) semicarbazide hydrochloride and 7.5 g (203 mol) Hydrazine hydrate was refluxed for 6 hours. The excess hydrazine was distilled off. The residue was dissolved in a sufficient amount of water and via an anionic substitute exchanger given. After distilling of the water, the carbohydrazide formed was stirred with alcohol and filtered off with suction.
Die Ausbeute an Carbohydrazid betrug bei diesem Herstellungsverfahren 3,4 g =A 75,6 %. Der Schmelzpunkt dieses Oarbohydrazids lag bei 150 - 152 ° C.The yield of carbohydrazide in this production process was 3.4 g = A 75.6%. The melting point of this obobohydrazide was 150 - 152 ° C.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112398 DE2112398A1 (en) | 1971-03-15 | 1971-03-15 | Carbohydrazide prepn - from hydrazine(hydrate) and urea or semicarbazide (salt) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112398 DE2112398A1 (en) | 1971-03-15 | 1971-03-15 | Carbohydrazide prepn - from hydrazine(hydrate) and urea or semicarbazide (salt) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2112398A1 true DE2112398A1 (en) | 1972-09-21 |
Family
ID=5801600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712112398 Pending DE2112398A1 (en) | 1971-03-15 | 1971-03-15 | Carbohydrazide prepn - from hydrazine(hydrate) and urea or semicarbazide (salt) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2112398A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269717A (en) * | 1980-04-17 | 1981-05-26 | Nalco Chemical Company | Boiler additives for oxygen scavenging |
| EP0103400A1 (en) * | 1982-08-17 | 1984-03-21 | Olin Corporation | Process for making carbohydrazide |
| JP2002275150A (en) * | 2001-03-16 | 2002-09-25 | Japan Hydrazine Co Inc | Method of producing carbodihydrazide |
| CN106674059A (en) * | 2017-01-03 | 2017-05-17 | 李亚杉 | Synthesis method of carbohydrazide |
| CN106831517A (en) * | 2017-02-06 | 2017-06-13 | 李亚杉 | A kind of synthetic method of thiocarbohydrazide |
| CN106986802A (en) * | 2017-05-22 | 2017-07-28 | 重庆丽澄环保科技有限公司 | A kind of method for synthesizing thiocarbohydrazide |
| PL425112A1 (en) * | 2018-04-03 | 2019-10-07 | Instytut Ciężkiej Syntezy Organicznej BLACHOWNIA | Method for producing carbohydrazide |
-
1971
- 1971-03-15 DE DE19712112398 patent/DE2112398A1/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269717A (en) * | 1980-04-17 | 1981-05-26 | Nalco Chemical Company | Boiler additives for oxygen scavenging |
| EP0103400A1 (en) * | 1982-08-17 | 1984-03-21 | Olin Corporation | Process for making carbohydrazide |
| JP2002275150A (en) * | 2001-03-16 | 2002-09-25 | Japan Hydrazine Co Inc | Method of producing carbodihydrazide |
| JP4641640B2 (en) * | 2001-03-16 | 2011-03-02 | 株式会社日本ファインケム | Method for producing carbodihydrazide |
| CN106674059A (en) * | 2017-01-03 | 2017-05-17 | 李亚杉 | Synthesis method of carbohydrazide |
| CN106831517A (en) * | 2017-02-06 | 2017-06-13 | 李亚杉 | A kind of synthetic method of thiocarbohydrazide |
| CN106986802A (en) * | 2017-05-22 | 2017-07-28 | 重庆丽澄环保科技有限公司 | A kind of method for synthesizing thiocarbohydrazide |
| PL425112A1 (en) * | 2018-04-03 | 2019-10-07 | Instytut Ciężkiej Syntezy Organicznej BLACHOWNIA | Method for producing carbohydrazide |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |