CN101397264B - 用于制备甲基肼的方法 - Google Patents
用于制备甲基肼的方法 Download PDFInfo
- Publication number
- CN101397264B CN101397264B CN200810211492.3A CN200810211492A CN101397264B CN 101397264 B CN101397264 B CN 101397264B CN 200810211492 A CN200810211492 A CN 200810211492A CN 101397264 B CN101397264 B CN 101397264B
- Authority
- CN
- China
- Prior art keywords
- hydrazine
- distillation
- mixture
- methyl
- mmh
- 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 - Fee Related
Links
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 112
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 238000004821 distillation Methods 0.000 claims abstract description 39
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000011541 reaction mixture Substances 0.000 claims abstract description 23
- 150000007530 organic bases Chemical class 0.000 claims abstract description 20
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims abstract description 17
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- 229940050176 methyl chloride Drugs 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 11
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 229960004418 trolamine Drugs 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 1
- 230000011987 methylation Effects 0.000 abstract 2
- 238000007069 methylation reaction Methods 0.000 abstract 2
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 13
- 239000003513 alkali Substances 0.000 description 10
- 150000002429 hydrazines Polymers 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical class O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 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 7
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000006353 environmental stress Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 238000000998 batch distillation Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 hydrazine compound Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- UAOZLNLYTGMSAV-UHFFFAOYSA-N NN.CN(C)C Chemical compound NN.CN(C)C UAOZLNLYTGMSAV-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- GIKDYMRZQQJQFB-UHFFFAOYSA-N Methylhydrazine hydrochloride Chemical compound Cl.CNN GIKDYMRZQQJQFB-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical class COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000009635 nitrosylation Effects 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007046467.5 | 2007-09-28 | ||
| DE102007046467A DE102007046467A1 (de) | 2007-09-28 | 2007-09-28 | Verfahren zur Herstellung von Monomethylhydrazin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101397264A CN101397264A (zh) | 2009-04-01 |
| CN101397264B true CN101397264B (zh) | 2013-03-27 |
Family
ID=40263014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810211492.3A Expired - Fee Related CN101397264B (zh) | 2007-09-28 | 2008-09-26 | 用于制备甲基肼的方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7683217B2 (enExample) |
| EP (1) | EP2042483B1 (enExample) |
| JP (1) | JP5322564B2 (enExample) |
| CN (1) | CN101397264B (enExample) |
| DE (1) | DE102007046467A1 (enExample) |
| ES (1) | ES2432575T3 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE426607B (sv) | 1982-03-29 | 1983-01-31 | Kamyr Ab | Sett att behandla en massasuspension som er i rorelse lengs en bana medelst fortrengning av massans suspensionsvetska med en eller flera ersettningsvetskor |
| CN104151190B (zh) * | 2014-08-07 | 2016-01-20 | 山东汇海医药化工有限公司 | 一种从甲基氨基硫脲合成母液中回收甲基肼的方法 |
| CN104628595B (zh) * | 2015-02-03 | 2017-05-17 | 西安近代化学研究所 | 一种42％甲基肼水溶液的制备方法 |
| CN104628594B (zh) * | 2015-02-03 | 2017-04-12 | 西安近代化学研究所 | 一种高纯度甲基肼的制备方法 |
| CN105037196B (zh) * | 2015-08-10 | 2017-03-29 | 济南大学 | 一种常压下催化合成甲基肼的新方法 |
| CN109180522B (zh) * | 2018-09-28 | 2021-01-29 | 吉林化工学院 | 一种去除叔丁基肼盐酸盐中盐酸肼的工艺 |
| CN110590595A (zh) * | 2019-09-26 | 2019-12-20 | 河北合佳医药科技集团股份有限公司 | 一种绿色高效的甲基肼粗品溶液精馏方法 |
| 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 |
| CN114133339A (zh) * | 2021-11-12 | 2022-03-04 | 东力（南通）化工有限公司 | 一种甲基肼连续流微通道烷基化方法 |
| CN114292208B (zh) * | 2021-12-27 | 2023-11-28 | 杭州新本立医药有限公司 | 一种固体酸催化制备甲基肼的方法 |
| CN117384063B (zh) * | 2023-08-29 | 2025-11-07 | 东力（南通）化工有限公司 | 一种三甲基肼的合成工艺及产品 |
| CN117160060B (zh) * | 2023-08-30 | 2025-10-31 | 湖北三峰透平装备股份有限公司 | 一种甲基联氨联合制备装置及制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2954283A (en) | 1957-12-02 | 1960-09-27 | Nat Distillers Chem Corp | Fuel mixtures |
| FR1260474A (fr) * | 1960-06-22 | 1961-05-05 | Olin Mathieson | Production de monométhylhydrazine anhydre par distillation extractive |
| US3423464A (en) * | 1966-08-25 | 1969-01-21 | Olin Mathieson | Process for the manufacture of monomethylhydrazine |
| JPS5399099A (en) * | 1977-02-09 | 1978-08-30 | Osuboogu Hansu | Method of making hydrazine |
| JPS5615257A (en) * | 1979-07-17 | 1981-02-14 | Nippon Hidorajin Kogyo Kk | Preparation of methylhydrazine |
| JPS5829296B2 (ja) * | 1980-12-10 | 1983-06-22 | 日本ヒドラジン工業株式会社 | モノメチルヒドラジンの製造方法 |
| JPH0239502B2 (ja) | 1982-03-15 | 1990-09-05 | Nippon Hydrogene Kogyo | Monomechiruhidorajinnokaishuhoho |
| JPS60237059A (ja) | 1984-05-09 | 1985-11-25 | Nippon Carbide Ind Co Ltd | モノアルキルヒドラジンの製法 |
-
2007
- 2007-09-28 DE DE102007046467A patent/DE102007046467A1/de not_active Withdrawn
-
2008
- 2008-09-17 ES ES08164473T patent/ES2432575T3/es active Active
- 2008-09-17 EP EP08164473.4A patent/EP2042483B1/de active Active
- 2008-09-18 US US12/233,010 patent/US7683217B2/en active Active
- 2008-09-26 CN CN200810211492.3A patent/CN101397264B/zh not_active Expired - Fee Related
- 2008-09-26 JP JP2008249197A patent/JP5322564B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101397264A (zh) | 2009-04-01 |
| EP2042483A1 (de) | 2009-04-01 |
| US20090187045A1 (en) | 2009-07-23 |
| DE102007046467A1 (de) | 2009-04-02 |
| EP2042483B1 (de) | 2013-08-28 |
| ES2432575T3 (es) | 2013-12-04 |
| US7683217B2 (en) | 2010-03-23 |
| JP5322564B2 (ja) | 2013-10-23 |
| JP2009102309A (ja) | 2009-05-14 |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
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| CF01 | Termination of patent right due to non-payment of annual fee |