CH378311A - Verfahren zur kontinuierlichen Herstellung von Hydrochloriden cycloaliphatischer Ketoxime - Google Patents
Verfahren zur kontinuierlichen Herstellung von Hydrochloriden cycloaliphatischer KetoximeInfo
- Publication number
- CH378311A CH378311A CH6857459A CH6857459A CH378311A CH 378311 A CH378311 A CH 378311A CH 6857459 A CH6857459 A CH 6857459A CH 6857459 A CH6857459 A CH 6857459A CH 378311 A CH378311 A CH 378311A
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- cycloalkane
- mixture
- chloride
- nitrosyl chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000003840 hydrochlorides Chemical class 0.000 title claims description 6
- 238000010924 continuous production Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 239000004157 Nitrosyl chloride Substances 0.000 claims description 39
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical group ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims description 39
- 235000019392 nitrosyl chloride Nutrition 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 150000001924 cycloalkanes Chemical class 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000007034 nitrosation reaction Methods 0.000 claims description 8
- 230000009935 nitrosation Effects 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 15
- 239000004914 cyclooctane Substances 0.000 description 14
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 13
- -1 oxime hydrochloride Chemical class 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- CEWJNZXLHJFHGA-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCCCC1 CEWJNZXLHJFHGA-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- WVQMNVHWDSLKKT-UHFFFAOYSA-N n-cyclohexylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCC1 WVQMNVHWDSLKKT-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0047847 | 1958-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH378311A true CH378311A (de) | 1964-06-15 |
Family
ID=6968391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6857459A CH378311A (de) | 1958-02-14 | 1959-01-20 | Verfahren zur kontinuierlichen Herstellung von Hydrochloriden cycloaliphatischer Ketoxime |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE575278A (enrdf_load_stackoverflow) |
| CH (1) | CH378311A (enrdf_load_stackoverflow) |
| NL (1) | NL236090A (enrdf_load_stackoverflow) |
-
0
- BE BE575278D patent/BE575278A/fr unknown
-
1959
- 1959-01-20 CH CH6857459A patent/CH378311A/de unknown
- 1959-02-13 NL NL236090A patent/NL236090A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE575278A (enrdf_load_stackoverflow) | |
| NL236090A (enrdf_load_stackoverflow) | 1964-03-10 |
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