US3607041A - Hydrazine - Google Patents
Hydrazine Download PDFInfo
- Publication number
- US3607041A US3607041A US765598A US3607041DA US3607041A US 3607041 A US3607041 A US 3607041A US 765598 A US765598 A US 765598A US 3607041D A US3607041D A US 3607041DA US 3607041 A US3607041 A US 3607041A
- Authority
- US
- United States
- Prior art keywords
- ketazine
- zone
- water
- hydrolyzing
- methylethyl
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title claims abstract description 50
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 40
- 230000003301 hydrolyzing effect Effects 0.000 claims description 37
- LAWAERKRWYQEEN-FKJILZIQSA-N (e)-n-[(z)-butan-2-ylideneamino]butan-2-imine Chemical compound CC\C(C)=N/N=C(\C)CC LAWAERKRWYQEEN-FKJILZIQSA-N 0.000 claims description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 9
- 150000007857 hydrazones Chemical class 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- -1 methylethyl hydrazone Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000035611 feeding Effects 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Images
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
Definitions
- the present invention relates to a process for preparing hydrazine from ketazines which are miscible with water only to a limited extent.
- hydrazine by hydrolysis of water-soluble acetone azine in aqueous solution at elevated temperature and ressures, the hydrolysis being conveniently effected on the trays of a fractioning column operated under pressure.
- ketazines Upon hydrolysis of ketazines, hydrazone and ketone are formed and hydrazine may be obtained by disproportionation of the hydrazone to hydrazine and the azine.
- the hydrolysis step involves handling a two-phase liquid system where the ketazines are miscible with water only to a limited extent and surprisingly it has been found possible to handle such a twophase liquid system if the residence time of the mixture which is fed to the column is relatively long in a zone in the vicinity of the point of feed of the mixture to the column prepared with the residence times in similar lengths of other parts of the column.
- the present invention is for a process for preparing hydrazine which comprises feeding a ketazine which is miscible with water only to a limited extent, such as methyl ethyl ketazine, and water to a distillation column operated at an elevated temperature and at a superatmospheric pressure, a zone in the vicinity of the point of feed of the ketazine to the column having plates so designed that the residence time thereof is relatively long compared with the re sidence times of plates or packing equivalent thereto outside this zone in other parts of the column and recovering an aqueous solution of hydrazine as bottoms.
- the ketazine In the zone in the vicinity of the ketazine feed, the ketazine is hydrolized to hydrazone, the presence of which increases the solubility of the ketazine thereby increasing its rate of hydrolysis. Below this zone hydrazone is disproportionated to azine and hydrazine, the azine being returned to the zone in the vicinity of the ketazine/water feed and hydrazine being recovered from the sump. In the zone above the ketazine/water feed zone unhydrolysed ketazine is condensed and returned to the ketazine/water feed zone and ketone/water is distilled off.
- the present invention is also for a fractionating column wherein trays in the vicinity of the feed inlet(s) to the column, have a greater residence time than each of the trays or packing equivalent thereto in the remainder of the column.
- the ketazine is converted to the ketone and hydrazine the ketone being removed as distillate and hydrazine being removed as bottoms.
- the ketazine and water may be fed to the distillation column at the same point or at different points. If the feeds are at different points the ketazine is preferably fed at a point below that at which the water is fed to the column. 1f the ketazine and water are fed at the same point they may be mixed before feeding. Preferably the feeds are heated before being fed to the column for example to a temperature in the range 60 to 160 C.
- the zone in the vicinity of the point of feed of the ketazine to the column is equivalent to 2-7 theoretical trays, preferably 3-5 theoretical plates, the zone below the ketazine feed zone is equivalent to 3-15 theoretical plates, preferably 5-10 theoretical plates, and the zone above the ketazine feed zone is equivalent to 3-15 theoretical plates preferably 5-12 theoretical plates.
- the zone in the vicinity of the point of feed of the ketazine to the column contains 2-6 actual high-residence-type trays having an overall residence time of 3-15 minutes.
- the zone in the vicinity of the point of feed of ketazine contains two or three highresidence-type trays immediately below the point of feed and one or two highresidence-type trays immediately above the point of feed.
- Ketazine and water are fed to column 1 through line 4 and ketone and water are removed through line 5. l-lydrazine and water are removed from the sump through line 6.
- EXAMPLE 1 A column 9 inches in diameter was packed with knitmesh except for the middle section which consisted of three high-residence-type trays. The liquid holdup of each of these high 'high-residence-type trays was approximately 250 cubic inches.
- the column was operated at a reflux ratio of 4:1 a pressure of pounds per square inch gauge and a sump temperature of 180 C.
- Methyl ethyl ketone azine (43.5 pounds per hour) and water (1 11 pounds per hour) were heated to C. and fed to the middle plate of the hydrolysis section.
- Methyl ethyl ketone (44.1 pounds per hour), water (14.9 pounds per hour) and methyl ethyl ketone azine (0.6 pounds per hour) were removed from the top of the column whilst hydrazine (9.80 pounds per hour), water (85.4 pounds per hour) and methyl ethyl ketone (0.11 pounds per hour) were continuously withdrawn from the sump.
- a process for the preparation of hydrazine by the fractional distillation of a ketazine at an elevated temperature and at a superatmospheric pressure sufficient to hydrolyze the ketazine in a hydrolyzing zone which process comprises;
- zone in the vicinity of the point of feed of the ketazine is equivalent to about 2-7 theoretical plates and the zones above and below the ketazine feed zone are each equivalent to about 3-15 theoretical plates.
- zone at the point of feed of the ketazine contains 2-3 high-residence-type trays immediately below the point of feed and 1-2 high-residence-type trays immediately above the point of feed.
- a process for the preparation of hydrazine by the fractional distillation of methylethyl ketazine in a distillation column in a hydrolyzing zone which process comprises:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB46564/67A GB1211547A (en) | 1967-10-12 | 1967-10-12 | Hydrazine |
Publications (1)
Publication Number | Publication Date |
---|---|
US3607041A true US3607041A (en) | 1971-09-21 |
Family
ID=10441737
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US765598A Expired - Lifetime US3607041A (en) | 1967-10-12 | 1968-10-07 | Hydrazine |
Country Status (4)
Country | Link |
---|---|
US (1) | US3607041A (de) |
JP (1) | JPS4948640B1 (de) |
DE (1) | DE1801912A1 (de) |
GB (1) | GB1211547A (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4036936A (en) * | 1975-08-15 | 1977-07-19 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing hydrazine hydrate |
US4724133A (en) * | 1975-09-10 | 1988-02-09 | Atochem | Preparation of concentrated aqueous solution of hydrazine hydrate |
US4725421A (en) * | 1975-09-10 | 1988-02-16 | Atochem | Process for the preparation of concentrated solutions of hydrazine hydrate |
US4963232A (en) * | 1987-05-28 | 1990-10-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a purified hydrazine hydrate |
US6375793B1 (en) * | 1994-02-07 | 2002-04-23 | Swarovski Optik Kg | Method and tower for removing residual monomers |
WO2018065997A1 (en) | 2016-10-03 | 2018-04-12 | Council Of Scientific & Industrial Research | An improved process for production of hydrazine hydrate |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3096049B1 (fr) | 2019-05-16 | 2021-12-17 | Arkema France | Procede ameliore de preparation d'hydrate d'hydrazine avec recyclage pyrazoline |
FR3096048B1 (fr) | 2019-05-16 | 2021-04-30 | Arkema France | Procede ameliore de preparation d'hydrate d'hydrazine avec recyclage oxime |
FR3130815A1 (fr) | 2021-12-21 | 2023-06-23 | Arkema France | Procede de preparation d'hydrate d'hydrazine en presence d’un agent anti-mousse |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3151046A (en) * | 1959-05-22 | 1964-09-29 | Phillips Petroleum Co | Methylethylpyridine-methylvinylpyridine fractionation |
US3189411A (en) * | 1961-02-08 | 1965-06-15 | Bayer Ag | Preparation of hydrazine hydrate |
-
1967
- 1967-10-12 GB GB46564/67A patent/GB1211547A/en not_active Expired
-
1968
- 1968-10-07 US US765598A patent/US3607041A/en not_active Expired - Lifetime
- 1968-10-08 JP JP43072908A patent/JPS4948640B1/ja active Pending
- 1968-10-09 DE DE19681801912 patent/DE1801912A1/de active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3151046A (en) * | 1959-05-22 | 1964-09-29 | Phillips Petroleum Co | Methylethylpyridine-methylvinylpyridine fractionation |
US3189411A (en) * | 1961-02-08 | 1965-06-15 | Bayer Ag | Preparation of hydrazine hydrate |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4036936A (en) * | 1975-08-15 | 1977-07-19 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing hydrazine hydrate |
US4724133A (en) * | 1975-09-10 | 1988-02-09 | Atochem | Preparation of concentrated aqueous solution of hydrazine hydrate |
US4725421A (en) * | 1975-09-10 | 1988-02-16 | Atochem | Process for the preparation of concentrated solutions of hydrazine hydrate |
US4963232A (en) * | 1987-05-28 | 1990-10-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a purified hydrazine hydrate |
US6375793B1 (en) * | 1994-02-07 | 2002-04-23 | Swarovski Optik Kg | Method and tower for removing residual monomers |
WO2018065997A1 (en) | 2016-10-03 | 2018-04-12 | Council Of Scientific & Industrial Research | An improved process for production of hydrazine hydrate |
Also Published As
Publication number | Publication date |
---|---|
DE1801912A1 (de) | 1969-05-14 |
JPS4948640B1 (de) | 1974-12-23 |
GB1211547A (en) | 1970-11-11 |
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