IL121799A - Preparation of aminoalkynes - Google Patents
Preparation of aminoalkynesInfo
- Publication number
- IL121799A IL121799A IL12179997A IL12179997A IL121799A IL 121799 A IL121799 A IL 121799A IL 12179997 A IL12179997 A IL 12179997A IL 12179997 A IL12179997 A IL 12179997A IL 121799 A IL121799 A IL 121799A
- Authority
- IL
- Israel
- Prior art keywords
- independently
- surfactant
- hydrogen atom
- chloroalkyne
- aminoalkyne
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000004094 surface-active agent Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000005576 amination reaction Methods 0.000 claims abstract description 17
- -1 alkynyl alcohol Chemical compound 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002280 amphoteric surfactant Substances 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- WTNNDYSRQSOJKB-UHFFFAOYSA-N 3-chloro-3-methylpent-1-yne Chemical compound CCC(C)(Cl)C#C WTNNDYSRQSOJKB-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YGWRQPVJLXLHAC-UHFFFAOYSA-N 3-methylpent-1-yn-3-amine Chemical compound CCC(C)(N)C#C YGWRQPVJLXLHAC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2686496P | 1996-10-01 | 1996-10-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL121799A0 IL121799A0 (en) | 1998-02-22 |
| IL121799A true IL121799A (en) | 2001-04-30 |
Family
ID=21834227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12179997A IL121799A (en) | 1996-10-01 | 1997-09-18 | Preparation of aminoalkynes |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0834498B1 (ko) |
| JP (1) | JPH10114727A (ko) |
| KR (1) | KR19980032426A (ko) |
| CN (1) | CN1124253C (ko) |
| AT (1) | ATE193520T1 (ko) |
| AU (1) | AU3759697A (ko) |
| BR (1) | BR9704945A (ko) |
| CA (1) | CA2215813A1 (ko) |
| DE (1) | DE69702171T2 (ko) |
| HU (1) | HUP9701594A3 (ko) |
| IL (1) | IL121799A (ko) |
| MX (1) | MX9707345A (ko) |
| TR (1) | TR199701087A2 (ko) |
| ZA (1) | ZA978492B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0312863D0 (en) | 2003-06-04 | 2003-07-09 | Syngenta Ltd | Fungicides |
| CN102180798B (zh) * | 2011-03-18 | 2013-11-06 | 湖北汉星化工新材料有限公司 | 一步法催化合成n,n-二乙基丙炔胺的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1927528C3 (de) * | 1969-05-30 | 1978-01-19 | Basf Ag | Verfahren zur herstellung von alpha- aethinylaminen |
| HU187775B (en) * | 1982-07-14 | 1986-02-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | New process for producing propargile-amines of pharmaceutical activity |
| US5254584A (en) * | 1992-12-18 | 1993-10-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
-
1997
- 1997-09-17 AU AU37596/97A patent/AU3759697A/en not_active Abandoned
- 1997-09-18 CA CA002215813A patent/CA2215813A1/en not_active Abandoned
- 1997-09-18 IL IL12179997A patent/IL121799A/en not_active IP Right Cessation
- 1997-09-22 ZA ZA9708492A patent/ZA978492B/xx unknown
- 1997-09-25 MX MX9707345A patent/MX9707345A/es not_active Application Discontinuation
- 1997-09-26 CN CN97116937A patent/CN1124253C/zh not_active Expired - Lifetime
- 1997-09-29 JP JP9279317A patent/JPH10114727A/ja not_active Withdrawn
- 1997-09-29 KR KR1019970049657A patent/KR19980032426A/ko not_active Application Discontinuation
- 1997-09-30 DE DE69702171T patent/DE69702171T2/de not_active Expired - Lifetime
- 1997-09-30 AT AT97307688T patent/ATE193520T1/de not_active IP Right Cessation
- 1997-09-30 BR BR9704945A patent/BR9704945A/pt not_active Application Discontinuation
- 1997-09-30 EP EP97307688A patent/EP0834498B1/en not_active Expired - Lifetime
- 1997-09-30 HU HU9701594A patent/HUP9701594A3/hu unknown
- 1997-10-01 TR TR97/01087A patent/TR199701087A2/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA978492B (en) | 1998-03-23 |
| CN1178214A (zh) | 1998-04-08 |
| DE69702171D1 (de) | 2000-07-06 |
| DE69702171T2 (de) | 2000-12-14 |
| MX9707345A (es) | 1998-04-30 |
| KR19980032426A (ko) | 1998-07-25 |
| EP0834498A1 (en) | 1998-04-08 |
| ATE193520T1 (de) | 2000-06-15 |
| HU9701594D0 (en) | 1997-11-28 |
| TR199701087A2 (xx) | 1998-04-21 |
| IL121799A0 (en) | 1998-02-22 |
| EP0834498B1 (en) | 2000-05-31 |
| CA2215813A1 (en) | 1998-04-01 |
| CN1124253C (zh) | 2003-10-15 |
| HUP9701594A3 (en) | 1999-04-28 |
| JPH10114727A (ja) | 1998-05-06 |
| HUP9701594A2 (hu) | 1998-07-28 |
| BR9704945A (pt) | 1999-05-18 |
| AU3759697A (en) | 1998-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |