DE1087119B - Manufacture of hydrazine hydrate - Google Patents
Manufacture of hydrazine hydrateInfo
- Publication number
- DE1087119B DE1087119B DEF26797A DEF0026797A DE1087119B DE 1087119 B DE1087119 B DE 1087119B DE F26797 A DEF26797 A DE F26797A DE F0026797 A DEF0026797 A DE F0026797A DE 1087119 B DE1087119 B DE 1087119B
- Authority
- DE
- Germany
- Prior art keywords
- sulfate
- water
- question
- hydrazine hydrate
- amount
- 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
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 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 claims description 3
- DBLJAFVPFHRQSP-UHFFFAOYSA-N aminoazanium;sulfate Chemical compound NN.NN.OS(O)(=O)=O DBLJAFVPFHRQSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims description 3
- 239000012493 hydrazine sulfate Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000010446 mirabilite Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004691 decahydrates Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/16—Hydrazine; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Nach bekannten Verfahren ist es möglich, wasserfreies Hydrazin aus trockenem Hydrazinsulfat durch Umsetzung mit reinem Ammoniak zu gewinnen.According to known methods it is possible to produce anhydrous hydrazine from dry hydrazine sulfate Implementation with pure ammonia to gain.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Gewinnung von Hydrazinhydrat aus Mono- oder Dihydrazinsulfat in Gegenwart von Wasser, das darin besteht, daß man die Hydrazinsulfatlösung mit einem Alkali- oder Erdalkalihydroxyd oder -oxyd versetzt, die Löslichkeit des entstehenden Alkali- oder Erdalkalisulfates durch den Zusatz einer wasserlöslichen organischen Verbindung senkt, das betreffende Sulfat abtrennt und die verbleibende Lösung durch Destillation auf Hydrazinhydrat aufarbeitet. Nach dem erfindungsgemäßen Verfahren wird die betreffende Salzlösung mit Alkali- bzw. Erdalkalihydroxyd und einem leicht wasserlöslichen einwertigen aliphatischen Alkohol oder Dioxan umgesetzt. Beim Einhalten bestimmter Konzentrations- und Temperaturbedingungen ist es hierbei überraschenderweise möglich, das unter diesen Umständen schwerlösliche Alkali- bzw. Erdalkalisulfat in Form eines sehr leicht filtrierbaren körnigen, kristallwasserfreien Niederschlages nahezu quantitativ abzuscheiden, der sich überdies gut auswaschen läßt. Im Falle der Ausfällung des Natriumsulfates wurde überraschenderweise gefunden, daß der Umwandlungspunkt des Natriumsulfates in das schwer filtrierbare Hepta- bzw. Dekahydrat bei der Abscheidung unter den erfindungsgemäßen Bedingungen von 32 bzw. 24° C auf .unter 150° C herabgesetzt wird. Auf diese Weise wird die Gefahr des Einschlusses hydrazinhaltiger Mutterlauge im Kristallwasser des Niederschlags vermieden.The present invention relates to a method for the production of hydrazine hydrate from mono- or dihydrazine sulfate in the presence of water, the consists in adding an alkali or alkaline earth metal hydroxide or oxide to the hydrazine sulfate solution, the solubility of the resulting alkali or alkaline earth sulfate by adding a water-soluble one organic compound lowers, separates the sulfate in question and the remaining solution through Worked up distillation on hydrazine hydrate. According to the method according to the invention, the relevant Salt solution with alkali or alkaline earth hydroxide and an easily water-soluble monovalent aliphatic Alcohol or dioxane implemented. When observing certain concentration and temperature conditions it is surprisingly possible here to remove the alkali or alkali metal, which is sparingly soluble under these circumstances, Alkaline earth sulfate in the form of a very easily filterable, granular precipitate that is almost free of water of crystallization to be separated quantitatively, which, moreover, can be washed out easily. In the case of sodium sulphate precipitation it was surprisingly found that the transition point of the sodium sulfate in the Difficult-to-filter hepta- or decahydrate when separating under the conditions according to the invention from 32 or 24 ° C to below 150 ° C will. In this way there is a risk of mother liquor containing hydrazine being trapped in the water of crystallization of precipitation avoided.
Als Basen zur Ausfällung der Schwefelsäure sind z. B. geeignet alle Alkalihydroxyde, speziell Natrium- und Kaliumhydroxyd, in Form ihrer konzentrierten Laugen, ferner alle Erdalkalioxyde, und -hydroxyde, besonders Calciumhydroxyd und Calciumoxyd. Die Menge der betreffenden Base wird so bemessen, daß ein Überschuß von 0 bis 5O°/o der stöchiometrischen Menge, bezogen auf die zu bindende Schwefelsäure, vorhanden ist.The bases for the precipitation of sulfuric acid are, for. B. suitable all alkali hydroxides, especially sodium and potassium hydroxide, in the form of their concentrated alkalis, furthermore all alkaline earth oxides and hydroxides, especially calcium hydroxide and calcium oxide. The amount of the base in question is such that an excess of 0 to 50% of the stoichiometric amount, based on the sulfuric acid to be bound, is available.
Als organische Verbindungen zur Ausfällung des betreffenden Sulfates werden leicht wasserlösliche einwertige aliphatische Alkohole, vorzugsweise Methyl-, Äthyl- und Propylalkohol, sowie Dioxan verwendet. Die Menge an organischem Lösungsmittel beträgt nach dem erfindungsgemäßen Verfahren 20 bis 500 °/o, vorzugsweise 50 bis 200°/o, bezogen auf die vorhandene Wassermenge. Die Temperatur während der Umsetzung mit der betreffenden Base sowie mit dem aliphatischen Alkohol liegt zwischen 15 und 100° C. Es empfiehlt sich, die Temperatur vor der Abtrennung des betreffenden Sulfates zur Erniedrigung der Löslichkeit auf 20 bis 30° C zu halten, wenn auchEasily water-soluble monovalent compounds are used as organic compounds for the precipitation of the sulfate in question aliphatic alcohols, preferably methyl, ethyl and propyl alcohol, and also dioxane are used. The amount of organic solvent in the process according to the invention is 20 to 500%, preferably 50 to 200%, based on the amount of water present. The temperature during the reaction with the base in question and with the aliphatic alcohol is between 15 and 100 ° C. It is recommended that the temperature before the separation of the sulfate in question to lower the Maintain solubility at 20 to 30 ° C, though
Herstellung von HydrazinhydratManufacture of hydrazine hydrate
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
Dr. Günter Henrich, Opladen,
ist als Erfinder genannt wordenDr. Günter Henrich, Opladen,
has been named as the inventor
durchaus höhere Temperaturen hierbei möglich sind.higher temperatures are possible here.
Die Trennung des Hydrazinhydrates nach der Sulfatabscheidung vom organischen Lösungsmittel ist auf destillatorischem Wege ohne weiteres möglich, so daß die weitere Aufarbeitung keine Schwierigkeiten mehr bereitet.The separation of the hydrazine hydrate after the sulphate separation from the organic solvent is easily possible by distillation, so that no further work-up is difficult more prepares.
In einem Rührgefäß werden 162 kg 5O°/oiges Dihydrazinsulfatlösung mit 84 kg 5O°/oiger NaOH gemischt. Anschließend wird dieses Gemisch in einem weiteren Rührgefäß mit 200 kg Methanol versetzt, die entstehende Suspension auf 20° C abgekühlt und filtriert. Es werden so 71 kg Natriumsulfat abgetrennt, die mit dem zum Einsatz bestimmten Methanol gewaschen werden. Das Filtrat, bestehend aus 200 kg Methanol, 50 kg Hydrazinhydrat, etwas NaOH und 123 kg Wasser, wird in einem Verdampfer fast restlos verdampft, wobei man den Dampf in die Mitte einer Kolonne leitet, die mit Verdampfer und Rücklaufkondensator versehen ist. Am Kopf der Kolonne wird Methanol und in der Mitte Wasser abgezogen, während man aus dem Sumpf reines Hydrazinhydrat gewinnt. 162 kg of 50% dihydrazine sulfate solution are placed in a stirred vessel mixed with 84 kg of 50% NaOH. Then this mixture is in one 200 kg of methanol are added to another stirred vessel, the resulting suspension is cooled to 20 ° C. and filtered. In this way 71 kg of sodium sulfate are separated off and washed with the methanol intended for use will. The filtrate, consisting of 200 kg of methanol, 50 kg of hydrazine hydrate, some NaOH and 123 kg of water is almost completely evaporated in an evaporator, with the steam in the middle of a Column passes, which is provided with evaporator and reflux condenser. At the head of the column is Methanol and water in the middle are drawn off, while pure hydrazine hydrate is obtained from the sump.
Claims (3)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26797A DE1087119B (en) | 1958-10-13 | 1958-10-13 | Manufacture of hydrazine hydrate |
| FR807231A FR1244517A (en) | 1958-10-13 | 1959-10-12 | Hydrazine hydrate manufacturing process |
| BE583504A BE583504A (en) | 1958-10-13 | 1959-10-12 | A method of manufacturing hydrazine hydrate. |
| GB3468759A GB876038A (en) | 1958-10-13 | 1959-10-13 | A process for the production of hydrazine hydrates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26797A DE1087119B (en) | 1958-10-13 | 1958-10-13 | Manufacture of hydrazine hydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1087119B true DE1087119B (en) | 1960-08-18 |
Family
ID=7092168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF26797A Pending DE1087119B (en) | 1958-10-13 | 1958-10-13 | Manufacture of hydrazine hydrate |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE583504A (en) |
| DE (1) | DE1087119B (en) |
| FR (1) | FR1244517A (en) |
| GB (1) | GB876038A (en) |
-
1958
- 1958-10-13 DE DEF26797A patent/DE1087119B/en active Pending
-
1959
- 1959-10-12 FR FR807231A patent/FR1244517A/en not_active Expired
- 1959-10-12 BE BE583504A patent/BE583504A/en unknown
- 1959-10-13 GB GB3468759A patent/GB876038A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1244517A (en) | 1960-10-28 |
| BE583504A (en) | 1960-02-01 |
| GB876038A (en) | 1961-08-30 |
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