DE1545616A1 - Verfahren zur Reinigung von Laurinlactam - Google Patents
Verfahren zur Reinigung von LaurinlactamInfo
- Publication number
- DE1545616A1 DE1545616A1 DE19511545616 DE1545616A DE1545616A1 DE 1545616 A1 DE1545616 A1 DE 1545616A1 DE 19511545616 DE19511545616 DE 19511545616 DE 1545616 A DE1545616 A DE 1545616A DE 1545616 A1 DE1545616 A1 DE 1545616A1
- Authority
- DE
- Germany
- Prior art keywords
- laurolactam
- water
- lactams
- lactam
- treatment
- 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.)
- Granted
Links
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 5
- 230000008707 rearrangement Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 150000003951 lactams Chemical class 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 238000004140 cleaning Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004157 Nitrosyl chloride Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 2
- 235000019392 nitrosyl chloride Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- -1 cyclododecane oxime Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/16—Separation or purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511545616 DE1545616A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Reinigung von Laurinlactam |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511545616 DE1545616A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Reinigung von Laurinlactam |
| DEB0083530 | 1965-09-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1545616A1 true DE1545616A1 (de) | 1969-09-04 |
| DE1545616B2 DE1545616B2 (enrdf_load_stackoverflow) | 1974-04-18 |
| DE1545616C3 DE1545616C3 (enrdf_load_stackoverflow) | 1974-11-21 |
Family
ID=25752867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511545616 Granted DE1545616A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Reinigung von Laurinlactam |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1545616A1 (enrdf_load_stackoverflow) |
-
1951
- 1951-01-28 DE DE19511545616 patent/DE1545616A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE1545616C3 (enrdf_load_stackoverflow) | 1974-11-21 |
| DE1545616B2 (enrdf_load_stackoverflow) | 1974-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69010904T2 (de) | Extraktionsverfahren zur entfernung von verunreinigungen aus terephthalsäurefiltrat. | |
| DE2127851A1 (de) | Verfahren zur Herstellung von Hydrochinon | |
| DE1593968C3 (de) | Verfahren zur Herstellung von Hydrochinon und Brenzcatechin | |
| DE2163259B2 (de) | Verfahren zur reinigung von rohlactamen mit 6 bis 12 kohlenstoffatomen im ring | |
| EP0018541B2 (de) | Verfahren zur Herstellung von 4-Nitrotoluol-2-sulfonsäure | |
| DE1545616A1 (de) | Verfahren zur Reinigung von Laurinlactam | |
| DE2708388C2 (de) | Verfahren zur Herstellung von 4,4'- Dihydroxydiphenylsulfon | |
| EP0523532A2 (de) | Verfahren zur Reinigung von Indigo | |
| DE2263247A1 (de) | Reinigung von anthrachinon | |
| DE2244172C3 (de) | Verfahren zur Herstellung von besonders reinen Tetrachlorbisphenolen | |
| DE1804693A1 (de) | Chemisches Verfahren | |
| DE2460912C3 (de) | Verfahren zur Herstellung von 2-Chlorbutadien-(M) | |
| DE2624472A1 (de) | Verfahren zur reinigung von adipinsaeure | |
| DE69017864T2 (de) | Verfahren zur Herstellung von Phenol. | |
| EP0475226B1 (de) | Verfahren zur Herstellung von 2-Mercapto-benzothiazol | |
| DE2646808C3 (de) | Verfahren zur Reinigung von im Zuge der Anthrachinonherstellung erhaltenem Phthalsäureanhydrid | |
| EP0115299A1 (de) | Verfahren zur gleichzeitigen Gewinnung von 4-Hydroxydiphenyl und 4,4'-Dihydroxydiphenyl | |
| EP0014406B1 (de) | Verfahren zur Abtrennung von Selen, Selenverbindungen, Schwefel und/oder Schwefelverbindungen aus diese Elemente bzw. Verbindungen aufweisenden Urethanen | |
| DE3519039C2 (enrdf_load_stackoverflow) | ||
| DE2535192C3 (de) | Verfahren zur Gewinnung von schwefelfreiem Reinnaphthalin und von Thionaphthen aus Steinkohlenteer | |
| DE2307310A1 (de) | Verfahren zur reinigung von diaminomaleonitril | |
| EP0189547B1 (de) | Verfahren zur Entfernung von Naphthochinon aus Phthalsäureanhydrid | |
| DE1002339C2 (de) | Verfahren zur Aufarbeitung des bei der Oxydation von technischem trans-Dekahydronaphthalin gebildeten Reaktionsgemisches | |
| DE2214225C2 (de) | Verfahren zur Gewinnung von Trimellitsäureanhydrid | |
| DE2403664A1 (de) | Verfahren zur reinigung von naphtalin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |