DE2023344A1 - Verfahren zur Reinigung von Caprolactam - Google Patents
Verfahren zur Reinigung von CaprolactamInfo
- Publication number
- DE2023344A1 DE2023344A1 DE19702023344 DE2023344A DE2023344A1 DE 2023344 A1 DE2023344 A1 DE 2023344A1 DE 19702023344 DE19702023344 DE 19702023344 DE 2023344 A DE2023344 A DE 2023344A DE 2023344 A1 DE2023344 A1 DE 2023344A1
- Authority
- DE
- Germany
- Prior art keywords
- caprolactam
- lactam
- weight
- parts
- crystallization
- 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.)
- Withdrawn
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 26
- 150000003951 lactams Chemical class 0.000 claims description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 12
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 12
- 230000008707 rearrangement Effects 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims 2
- 150000003738 xylenes Chemical class 0.000 claims 1
- 238000004140 cleaning Methods 0.000 description 18
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PWXIKGAMKWRXHD-UHFFFAOYSA-N 3-butylaziridin-2-one Chemical compound CCCCC1NC1=O PWXIKGAMKWRXHD-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000006085 Schmidt reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 hexenoic acid nitriles Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702023344 DE2023344A1 (de) | 1970-05-13 | 1970-05-13 | Verfahren zur Reinigung von Caprolactam |
| CA127,089A CA964656A (en) | 1970-05-13 | 1971-11-08 | Process for the purification of caprolactam |
| FR7140161A FR2159180A1 (en) | 1970-05-13 | 1971-11-09 | Epsilon caprolactam purificn - by crystallisation from aromatic solvent and distillation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702023344 DE2023344A1 (de) | 1970-05-13 | 1970-05-13 | Verfahren zur Reinigung von Caprolactam |
| FR7140161A FR2159180A1 (en) | 1970-05-13 | 1971-11-09 | Epsilon caprolactam purificn - by crystallisation from aromatic solvent and distillation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2023344A1 true DE2023344A1 (de) | 1971-11-25 |
Family
ID=25759133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702023344 Withdrawn DE2023344A1 (de) | 1970-05-13 | 1970-05-13 | Verfahren zur Reinigung von Caprolactam |
Country Status (3)
| Country | Link |
|---|---|
| CA (1) | CA964656A (enExample) |
| DE (1) | DE2023344A1 (enExample) |
| FR (1) | FR2159180A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2619234A1 (de) * | 1975-05-01 | 1976-11-25 | Stamicarbon | Verfahren zur gewinnung von reinem epsilon-caprolactam aus einer waessrigen loesung desselben |
| EP0570110A1 (en) * | 1992-04-17 | 1993-11-18 | Sumitomo Chemical Company, Limited | Process for producing a high purity caprolactam |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1490312A (fr) * | 1965-09-11 | 1967-07-28 | Zimmer Ag Hans J | Procédé perfectionné de purification de l'epsilon-caprolactame |
-
1970
- 1970-05-13 DE DE19702023344 patent/DE2023344A1/de not_active Withdrawn
-
1971
- 1971-11-08 CA CA127,089A patent/CA964656A/en not_active Expired
- 1971-11-09 FR FR7140161A patent/FR2159180A1/fr active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2619234A1 (de) * | 1975-05-01 | 1976-11-25 | Stamicarbon | Verfahren zur gewinnung von reinem epsilon-caprolactam aus einer waessrigen loesung desselben |
| EP0570110A1 (en) * | 1992-04-17 | 1993-11-18 | Sumitomo Chemical Company, Limited | Process for producing a high purity caprolactam |
| US5362870A (en) * | 1992-04-17 | 1994-11-08 | Sumitomo Chemical Company, Ltd. | Process for producing a high purity caprolactam |
| US5459261A (en) * | 1992-04-17 | 1995-10-17 | Sumitomo Chemical Company, Limited | Process for producing a high purity caprolactam |
| US5525725A (en) * | 1992-04-17 | 1996-06-11 | Sumitomo Chemical Company, Limited | Process for producing a high purity caprolactam |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2159180B1 (enExample) | 1976-03-26 |
| FR2159180A1 (en) | 1973-06-22 |
| CA964656A (en) | 1975-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal | ||
| 8165 | Unexamined publication of following application revoked |