DE1265742B - Verfahren zur Herstellung von 1, 4-Bis-(monoalkylamino)-trans-butenen-(2) - Google Patents
Verfahren zur Herstellung von 1, 4-Bis-(monoalkylamino)-trans-butenen-(2)Info
- Publication number
- DE1265742B DE1265742B DEF47760A DEF0047760A DE1265742B DE 1265742 B DE1265742 B DE 1265742B DE F47760 A DEF47760 A DE F47760A DE F0047760 A DEF0047760 A DE F0047760A DE 1265742 B DE1265742 B DE 1265742B
- Authority
- DE
- Germany
- Prior art keywords
- trans
- bis
- butene
- monoalkylamino
- dichloro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- -1 2 Chemical compound 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- SWSOIFQIPTXLOI-HNQUOIGGSA-N (e)-1,4-dichlorobut-1-ene Chemical compound ClCC\C=C\Cl SWSOIFQIPTXLOI-HNQUOIGGSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004985 diamines Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GKBHYEKPVGINRL-YCRREMRBSA-N (e)-n-benzylbut-1-en-1-amine Chemical compound CC\C=C\NCC1=CC=CC=C1 GKBHYEKPVGINRL-YCRREMRBSA-N 0.000 description 1
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical class NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47760A DE1265742B (de) | 1965-11-25 | 1965-11-25 | Verfahren zur Herstellung von 1, 4-Bis-(monoalkylamino)-trans-butenen-(2) |
| GB5160466A GB1162028A (en) | 1965-11-25 | 1966-11-17 | Process for Preparing 1.4-bis-(mono-alkylamino)-trans-butenes-(2) |
| NL6616271A NL6616271A (OSRAM) | 1965-11-25 | 1966-11-18 | |
| CH1670866A CH479536A (de) | 1965-11-25 | 1966-11-22 | Verfahren zur Herstellung von 1,4-Bis-amino-transbutenen-(2) |
| FR85007A FR1501605A (fr) | 1965-11-25 | 1966-11-25 | Procédé de préparation de 1.4-bis-(monoalkylamino)-trans-butènes-(2) |
| BE690220D BE690220A (OSRAM) | 1965-11-25 | 1966-11-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47760A DE1265742B (de) | 1965-11-25 | 1965-11-25 | Verfahren zur Herstellung von 1, 4-Bis-(monoalkylamino)-trans-butenen-(2) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1265742B true DE1265742B (de) | 1968-04-11 |
Family
ID=7101828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF47760A Pending DE1265742B (de) | 1965-11-25 | 1965-11-25 | Verfahren zur Herstellung von 1, 4-Bis-(monoalkylamino)-trans-butenen-(2) |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE690220A (OSRAM) |
| CH (1) | CH479536A (OSRAM) |
| DE (1) | DE1265742B (OSRAM) |
| FR (1) | FR1501605A (OSRAM) |
| GB (1) | GB1162028A (OSRAM) |
| NL (1) | NL6616271A (OSRAM) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB595540A (en) * | 1945-07-06 | 1947-12-08 | Alan Woodworth Johnson | 1:4-diamino-2-butines |
-
1965
- 1965-11-25 DE DEF47760A patent/DE1265742B/de active Pending
-
1966
- 1966-11-17 GB GB5160466A patent/GB1162028A/en not_active Expired
- 1966-11-18 NL NL6616271A patent/NL6616271A/xx unknown
- 1966-11-22 CH CH1670866A patent/CH479536A/de not_active IP Right Cessation
- 1966-11-25 BE BE690220D patent/BE690220A/xx unknown
- 1966-11-25 FR FR85007A patent/FR1501605A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB595540A (en) * | 1945-07-06 | 1947-12-08 | Alan Woodworth Johnson | 1:4-diamino-2-butines |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6616271A (OSRAM) | 1967-05-26 |
| FR1501605A (fr) | 1967-11-10 |
| GB1162028A (en) | 1969-08-20 |
| BE690220A (OSRAM) | 1967-05-25 |
| CH479536A (de) | 1969-10-15 |
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