DE2727832C3 - Verfahren zur Herstellung von N'-Methylacethydrazid - Google Patents
Verfahren zur Herstellung von N'-MethylacethydrazidInfo
- Publication number
- DE2727832C3 DE2727832C3 DE2727832A DE2727832A DE2727832C3 DE 2727832 C3 DE2727832 C3 DE 2727832C3 DE 2727832 A DE2727832 A DE 2727832A DE 2727832 A DE2727832 A DE 2727832A DE 2727832 C3 DE2727832 C3 DE 2727832C3
- Authority
- DE
- Germany
- Prior art keywords
- acethydrazide
- hydrogen
- paraformaldehyde
- catalyst
- reaction
- 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
- 238000000034 method Methods 0.000 title description 18
- OMMMMWZZJZZMLV-UHFFFAOYSA-N n'-methylacetohydrazide Chemical compound CNNC(C)=O OMMMMWZZJZZMLV-UHFFFAOYSA-N 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000001257 hydrogen Substances 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 11
- 229920002866 paraformaldehyde Polymers 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- -1 aliphatic hydrazines Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910003445 palladium oxide Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- PLNNJQXIITYYTN-UHFFFAOYSA-N 2-methylpropanehydrazide Chemical compound CC(C)C(=O)NN PLNNJQXIITYYTN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- 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
- C07C241/04—Preparation of hydrazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/698,452 US4045484A (en) | 1975-07-16 | 1976-06-21 | Process for preparing N'-methyl acethydrazide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2727832A1 DE2727832A1 (de) | 1977-12-22 |
| DE2727832B2 DE2727832B2 (de) | 1979-11-15 |
| DE2727832C3 true DE2727832C3 (de) | 1981-03-12 |
Family
ID=24805311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2727832A Expired DE2727832C3 (de) | 1976-06-21 | 1977-06-21 | Verfahren zur Herstellung von N'-Methylacethydrazid |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS52156809A (nl) |
| BE (1) | BE855863A (nl) |
| CA (1) | CA1088097A (nl) |
| CH (1) | CH625504A5 (nl) |
| DE (1) | DE2727832C3 (nl) |
| FR (1) | FR2355809A1 (nl) |
| GB (1) | GB1576859A (nl) |
| NL (1) | NL7706868A (nl) |
| ZA (1) | ZA773719B (nl) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH307629A (de) * | 1952-05-23 | 1955-06-15 | Ag J R Geigy | Verfahren zur Herstellung eines monosubstituierten Hydrazins. |
-
1977
- 1977-03-01 CA CA272,920A patent/CA1088097A/en not_active Expired
- 1977-06-20 FR FR7718825A patent/FR2355809A1/fr active Granted
- 1977-06-20 BE BE178573A patent/BE855863A/xx unknown
- 1977-06-21 DE DE2727832A patent/DE2727832C3/de not_active Expired
- 1977-06-21 CH CH759577A patent/CH625504A5/fr not_active IP Right Cessation
- 1977-06-21 NL NL7706868A patent/NL7706868A/nl not_active Application Discontinuation
- 1977-06-21 GB GB25848/77A patent/GB1576859A/en not_active Expired
- 1977-06-21 JP JP7381677A patent/JPS52156809A/ja active Granted
- 1977-06-21 ZA ZA00773719A patent/ZA773719B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1088097A (en) | 1980-10-21 |
| NL7706868A (nl) | 1977-12-23 |
| FR2355809A1 (fr) | 1978-01-20 |
| CH625504A5 (en) | 1981-09-30 |
| ZA773719B (en) | 1978-05-30 |
| BE855863A (fr) | 1977-12-20 |
| JPS543852B2 (nl) | 1979-02-27 |
| DE2727832A1 (de) | 1977-12-22 |
| JPS52156809A (en) | 1977-12-27 |
| FR2355809B1 (nl) | 1980-07-18 |
| DE2727832B2 (de) | 1979-11-15 |
| GB1576859A (en) | 1980-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |