DE3148971C2 - - Google Patents
Info
- Publication number
- DE3148971C2 DE3148971C2 DE3148971A DE3148971A DE3148971C2 DE 3148971 C2 DE3148971 C2 DE 3148971C2 DE 3148971 A DE3148971 A DE 3148971A DE 3148971 A DE3148971 A DE 3148971A DE 3148971 C2 DE3148971 C2 DE 3148971C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrazine
- methanol
- selectivity
- mol
- monohydrochloride
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 39
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 34
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- 229940050176 methyl chloride Drugs 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 claims description 13
- GIKDYMRZQQJQFB-UHFFFAOYSA-N Methylhydrazine hydrochloride Chemical compound Cl.CNN GIKDYMRZQQJQFB-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- -1 methyl halide Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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 description 1
- NIIPNAJXERMYOG-UHFFFAOYSA-N 1,1,2-trimethylhydrazine Chemical compound CNN(C)C NIIPNAJXERMYOG-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- DLRICKJDQFHZGI-UHFFFAOYSA-N ammonia;chloroamine Chemical compound N.ClN DLRICKJDQFHZGI-UHFFFAOYSA-N 0.000 description 1
- 229940045984 antineoplastic methylhydrazine Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55173116A JPS5829296B2 (ja) | 1980-12-10 | 1980-12-10 | モノメチルヒドラジンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3148971A1 DE3148971A1 (de) | 1982-07-29 |
| DE3148971C2 true DE3148971C2 (en, 2012) | 1988-08-18 |
Family
ID=15954436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813148971 Granted DE3148971A1 (de) | 1980-12-10 | 1981-12-10 | Verfahren zur herstellung von monomethylhydrazin |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4855501A (en, 2012) |
| JP (1) | JPS5829296B2 (en, 2012) |
| DE (1) | DE3148971A1 (en, 2012) |
| GB (1) | GB2090828B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59137453A (ja) * | 1983-01-25 | 1984-08-07 | Nippon Hidorajin Kogyo Kk | タ−シヤリ−ブチルヒドラジンの製造方法 |
| JPH0684896U (ja) * | 1993-05-27 | 1994-12-06 | 貴子 条谷 | 煙草サービススタンド |
| DE102007046467A1 (de) | 2007-09-28 | 2009-04-02 | Saltigo Gmbh | Verfahren zur Herstellung von Monomethylhydrazin |
| CN103130678A (zh) * | 2013-03-12 | 2013-06-05 | 东力（南通）化工有限公司 | 质量浓度为40%的甲基肼水溶液提浓至98%的方法 |
| CN105315172B (zh) * | 2015-12-07 | 2017-06-23 | 济南大学 | 一种分离水—甲基肼共沸混合物的新工艺 |
| CN106543026B (zh) * | 2016-10-31 | 2018-01-16 | 石家庄金派医药化工有限公司 | 一种甲基肼的制备方法 |
| CN109400497A (zh) * | 2018-12-11 | 2019-03-01 | 河北合佳医药科技集团股份有限公司 | 一种甲基肼的清洁生产工艺 |
| CN109503418B (zh) * | 2018-12-11 | 2021-06-08 | 河北合佳医药科技集团股份有限公司 | 一种甲基肼的制备工艺 |
| CN111320554A (zh) * | 2019-12-11 | 2020-06-23 | 东力（南通）化工有限公司 | 一种一甲基肼生产工艺改进技术 |
| CN117384062A (zh) * | 2023-08-29 | 2024-01-12 | 东力（南通）化工有限公司 | 一种连续催化合成甲基肼工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3083229A (en) * | 1958-10-09 | 1963-03-26 | Dow Chemical Co | Propynyl-hydrazines |
| GB875152A (en) * | 1958-12-31 | 1961-08-16 | Us Rubber Co | Method for the preparation of poly substituted hydrazine derivatives |
| US3140315A (en) * | 1959-02-18 | 1964-07-07 | Bayer Ag | Alkyl-substituted hydrazines and hydrazones and process for preparation thereof |
| US4124452A (en) * | 1978-05-22 | 1978-11-07 | The United States Of America As Represented By The Secretary Of The Navy | Distillation technique for removal of UDMH from water |
| JPS5615257A (en) * | 1979-07-17 | 1981-02-14 | Nippon Hidorajin Kogyo Kk | Preparation of methylhydrazine |
-
1980
- 1980-12-10 JP JP55173116A patent/JPS5829296B2/ja not_active Expired
-
1981
- 1981-12-03 US US06/327,088 patent/US4855501A/en not_active Expired - Lifetime
- 1981-12-07 GB GB8136798A patent/GB2090828B/en not_active Expired
- 1981-12-10 DE DE19813148971 patent/DE3148971A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2090828B (en) | 1984-11-07 |
| GB2090828A (en) | 1982-07-21 |
| JPS5829296B2 (ja) | 1983-06-22 |
| US4855501A (en) | 1989-08-08 |
| JPS5798247A (en) | 1982-06-18 |
| DE3148971A1 (de) | 1982-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8120 | Willingness to grant licences paragraph 23 | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |