CH419107A - Verfahren zur Herstellung von Cyclooctylamin - Google Patents
Verfahren zur Herstellung von CyclooctylaminInfo
- Publication number
- CH419107A CH419107A CH1074563A CH1074563A CH419107A CH 419107 A CH419107 A CH 419107A CH 1074563 A CH1074563 A CH 1074563A CH 1074563 A CH1074563 A CH 1074563A CH 419107 A CH419107 A CH 419107A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclooctene
- cyclooctylamine
- sulfuric acid
- reaction mixture
- acid
- Prior art date
Links
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 32
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 31
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 17
- 239000004913 cyclooctene Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 5
- XCFPVEPFJPBYAS-UHFFFAOYSA-N n-cyclooctylformamide Chemical compound O=CNC1CCCCCCC1 XCFPVEPFJPBYAS-UHFFFAOYSA-N 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- SWGXDLRCJNEEGZ-UHFFFAOYSA-N N-cyclohexylformamide Chemical compound O=CNC1CCCCC1 SWGXDLRCJNEEGZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XBWOPGDJMAJJDG-UHFFFAOYSA-N 1-cyclohexylethanamine Chemical compound CC(N)C1CCCCC1 XBWOPGDJMAJJDG-UHFFFAOYSA-N 0.000 description 1
- ALTNHEBBNUHKKU-UHFFFAOYSA-N 1-cyclooctylcyclooctene Chemical compound C1CCCCCCC1C1=CCCCCCC1 ALTNHEBBNUHKKU-UHFFFAOYSA-N 0.000 description 1
- MQOMKCIKNDDXEZ-UHFFFAOYSA-N 1-dibutylphosphoryloxy-4-nitrobenzene Chemical compound CCCCP(=O)(CCCC)OC1=CC=C([N+]([O-])=O)C=C1 MQOMKCIKNDDXEZ-UHFFFAOYSA-N 0.000 description 1
- HFACYWDPMNWMIW-UHFFFAOYSA-N 2-cyclohexylethanamine Chemical compound NCCC1CCCCC1 HFACYWDPMNWMIW-UHFFFAOYSA-N 0.000 description 1
- 101000713211 Colocasia esculenta Mannose-specific lectin TAR1 Proteins 0.000 description 1
- -1 N-substituted formamides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- YBWITBVNLGRBPJ-UHFFFAOYSA-N formonitrile;sulfuric acid Chemical compound N#C.OS(O)(=O)=O YBWITBVNLGRBPJ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB68739A DE1178846B (de) | 1962-09-06 | 1962-09-06 | Verfahren zur Herstellung von Cyclooctylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH419107A true CH419107A (de) | 1966-08-31 |
Family
ID=6976019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1074563A CH419107A (de) | 1962-09-06 | 1963-08-30 | Verfahren zur Herstellung von Cyclooctylamin |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT242680B (enExample) |
| BE (1) | BE637032A (enExample) |
| CH (1) | CH419107A (enExample) |
| DE (1) | DE1178846B (enExample) |
| GB (1) | GB987198A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2819306A (en) * | 1953-09-14 | 1958-01-07 | Firestone Tire & Rubber Co | Preparation of formamides by reacting hydrogen cyanide with cyclohexene |
-
0
- BE BE637032D patent/BE637032A/xx unknown
-
1962
- 1962-09-06 DE DEB68739A patent/DE1178846B/de active Pending
-
1963
- 1963-08-22 GB GB3322363A patent/GB987198A/en not_active Expired
- 1963-08-30 CH CH1074563A patent/CH419107A/de unknown
- 1963-09-06 AT AT722163A patent/AT242680B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB987198A (en) | 1965-03-24 |
| AT242680B (de) | 1965-09-27 |
| DE1178846B (de) | 1964-10-01 |
| BE637032A (enExample) |
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