DE1178846B - Verfahren zur Herstellung von Cyclooctylamin - Google Patents
Verfahren zur Herstellung von CyclooctylaminInfo
- Publication number
- DE1178846B DE1178846B DEB68739A DEB0068739A DE1178846B DE 1178846 B DE1178846 B DE 1178846B DE B68739 A DEB68739 A DE B68739A DE B0068739 A DEB0068739 A DE B0068739A DE 1178846 B DE1178846 B DE 1178846B
- Authority
- DE
- Germany
- Prior art keywords
- cyclooctylamine
- cyclooctene
- parts
- amine
- weight
- 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
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 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 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 14
- 239000004913 cyclooctene Substances 0.000 claims description 14
- XCFPVEPFJPBYAS-UHFFFAOYSA-N n-cyclooctylformamide Chemical compound O=CNC1CCCCCCC1 XCFPVEPFJPBYAS-UHFFFAOYSA-N 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000001816 cooling Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 235000019253 formic acid Nutrition 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
- -1 N-substituted formamides Chemical class 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- JJTCHEOKVCQQSH-UHFFFAOYSA-N n-(1-ethylcyclohexyl)formamide Chemical compound O=CNC1(CC)CCCCC1 JJTCHEOKVCQQSH-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE637032D BE637032A (enExample) | 1962-09-06 | ||
| DEB68739A DE1178846B (de) | 1962-09-06 | 1962-09-06 | Verfahren zur Herstellung von Cyclooctylamin |
| GB3322363A GB987198A (en) | 1962-09-06 | 1963-08-22 | Production of cyclooctylamine |
| CH1074563A CH419107A (de) | 1962-09-06 | 1963-08-30 | Verfahren zur Herstellung von Cyclooctylamin |
| AT722163A AT242680B (de) | 1962-09-06 | 1963-09-06 | Verfahren zur Herstellung von Cyclooctylamin |
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 |
|---|---|
| DE1178846B true DE1178846B (de) | 1964-10-01 |
Family
ID=6976019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB68739A Pending DE1178846B (de) | 1962-09-06 | 1962-09-06 | 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) |
Citations (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
Patent Citations (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB987198A (en) | 1965-03-24 |
| CH419107A (de) | 1966-08-31 |
| AT242680B (de) | 1965-09-27 |
| BE637032A (enExample) |
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