CN112624938A - 一种合成乙基肼二盐酸盐的新方法 - Google Patents
一种合成乙基肼二盐酸盐的新方法 Download PDFInfo
- Publication number
- CN112624938A CN112624938A CN202010695619.4A CN202010695619A CN112624938A CN 112624938 A CN112624938 A CN 112624938A CN 202010695619 A CN202010695619 A CN 202010695619A CN 112624938 A CN112624938 A CN 112624938A
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- CN
- China
- Prior art keywords
- ethyl hydrazine
- solvent
- dihydrochloride
- acetyl
- acethydrazide
- 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.)
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- ICIVIXSUYOSPAL-UHFFFAOYSA-N ethylhydrazine;dihydrochloride Chemical compound Cl.Cl.CCNN ICIVIXSUYOSPAL-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 21
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 11
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000009776 industrial production Methods 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 16
- SOHGTZGWMYZGGJ-UHFFFAOYSA-N n-ethylacetohydrazide Chemical compound CCN(N)C(C)=O SOHGTZGWMYZGGJ-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- -1 copper (I) chloro [1, 3-bis (2, 6-diisopropylphenyl) imidazol-2-ylidene ] copper (I) Chemical compound 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000001308 synthesis method Methods 0.000 claims description 5
- VTPSRWHMEJMWGN-UHFFFAOYSA-N 4-hydrazinylbutan-2-one Chemical compound CC(=O)CCNN VTPSRWHMEJMWGN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 238000012790 confirmation Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- UIWVQFSAXYWENY-UHFFFAOYSA-N n'-ethylacetohydrazide Chemical compound CCNNC(C)=O UIWVQFSAXYWENY-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- SKEHVMZPBBGBAO-UHFFFAOYSA-N ethylhydrazine;hydrochloride Chemical compound Cl.CCNN SKEHVMZPBBGBAO-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QZVRXWBKQJFSLP-UHFFFAOYSA-N 2-ethyl-1h-pyrazol-3-one Chemical compound CCN1NC=CC1=O QZVRXWBKQJFSLP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- HKRINCVYMIAYBE-UHFFFAOYSA-M copper 1,3-bis[2,6-di(propan-2-yl)phenyl]-2H-imidazol-2-ide chloride Chemical compound [Cl-].[Cu+2].CC(C)C1=CC=CC(C(C)C)=C1N1C=CN(C=2C(=CC=CC=2C(C)C)C(C)C)[CH-]1 HKRINCVYMIAYBE-UHFFFAOYSA-M 0.000 description 2
- 230000006203 ethylation Effects 0.000 description 2
- 238000006200 ethylation reaction Methods 0.000 description 2
- 235000013842 nitrous oxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- SYVLAGSPNDOFGH-UHFFFAOYSA-N [Li+].[O-2].[O-2].O.O.[Al+3] Chemical compound [Li+].[O-2].[O-2].O.O.[Al+3] SYVLAGSPNDOFGH-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- LJNKLCWPWAPYME-UHFFFAOYSA-N copper;2,2,6,6-tetramethylheptane-3,5-dione Chemical compound [Cu].CC(C)(C)C(=O)CC(=O)C(C)(C)C.CC(C)(C)C(=O)CC(=O)C(C)(C)C LJNKLCWPWAPYME-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229940124828 glucokinase activator Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
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CN202010695619.4A CN112624938B (zh) | 2020-07-20 | 2020-07-20 | 一种合成乙基肼二盐酸盐的新方法 |
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CN202010695619.4A CN112624938B (zh) | 2020-07-20 | 2020-07-20 | 一种合成乙基肼二盐酸盐的新方法 |
Publications (2)
Publication Number | Publication Date |
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CN112624938A true CN112624938A (zh) | 2021-04-09 |
CN112624938B CN112624938B (zh) | 2022-12-30 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101003494A (zh) * | 2007-01-22 | 2007-07-25 | 上海化学试剂研究所 | 肼基乙酸乙酯盐酸盐的制备方法 |
CN105732468A (zh) * | 2016-04-07 | 2016-07-06 | 昆明理工大学 | 一种n’-(2-(1h-吲哚-3-基)乙酰基)芳酰肼类化合物及其制备方法和用途 |
-
2020
- 2020-07-20 CN CN202010695619.4A patent/CN112624938B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101003494A (zh) * | 2007-01-22 | 2007-07-25 | 上海化学试剂研究所 | 肼基乙酸乙酯盐酸盐的制备方法 |
CN105732468A (zh) * | 2016-04-07 | 2016-07-06 | 昆明理工大学 | 一种n’-(2-(1h-吲哚-3-基)乙酰基)芳酰肼类化合物及其制备方法和用途 |
Non-Patent Citations (4)
Title |
---|
ALEXANDER G. TSKHOVREBOV .ECT: "Reactions of Grignard Reagents with Nitrous Oxide", 《ORGANOMETALLICS》 * |
B.MAOTKOWSK .ECT: "SOLID NaOH/K2C03-A NEW HIGHLY EFFECTIVE BASE FOR PHASE-TRANSFER CATALYSED N-ALKYLATION OF DIPHENYLE"HOSPHINIHCY DIUZIDE", 《TETRAHEDRON LETTERS》 * |
CONDON, F. E.ECT: "Ethylhydrazine. Fischer synthesis revisited", 《PROCEDURES INTERNATIONAL》 * |
V. YU. GUSEV .ECT: "Complexation and extraction properties of N´,N´-dibutyloctanohydrazide", 《RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION》 * |
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TR01 | Transfer of patent right |
Effective date of registration: 20240731 Address after: 300071 Tianjin City, Nankai District Wei Jin Road No. 94, Nankai University Patentee after: Xu Fengbo Country or region after: China Address before: 300071 Tianjin City, Nankai District Wei Jin Road No. 94, Nankai University Patentee before: NANKAI University Country or region before: China |
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Effective date of registration: 20240806 Address after: 300112 Tianjin Science and Technology Plaza 6-1205 (Tiankai Park), West Scientific Research Road, Nankai District, Tianjin Patentee after: Tianjin Tiankai Ruilai Co.,Ltd. Country or region after: China Address before: 300071 Tianjin City, Nankai District Wei Jin Road No. 94, Nankai University Patentee before: Xu Fengbo Country or region before: China |
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