DE1695247C3 - Verfahren zur Reinigung von Lactamen durch Schmelzkristallisation - Google Patents
Verfahren zur Reinigung von Lactamen durch SchmelzkristallisationInfo
- Publication number
- DE1695247C3 DE1695247C3 DE1695247A DE1695247A DE1695247C3 DE 1695247 C3 DE1695247 C3 DE 1695247C3 DE 1695247 A DE1695247 A DE 1695247A DE 1695247 A DE1695247 A DE 1695247A DE 1695247 C3 DE1695247 C3 DE 1695247C3
- Authority
- DE
- Germany
- Prior art keywords
- lactam
- melt
- crystallization
- crystals
- caprolactam
- 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.)
- Expired
Links
- 150000003951 lactams Chemical class 0.000 title claims description 70
- 238000002425 crystallisation Methods 0.000 title claims description 30
- 230000008025 crystallization Effects 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 23
- 238000000746 purification Methods 0.000 title claims description 5
- 239000013078 crystal Substances 0.000 claims description 41
- 239000000155 melt Substances 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 18
- 239000002002 slurry Substances 0.000 claims description 9
- 238000004140 cleaning Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000000605 extraction Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 230000008023 solidification Effects 0.000 description 7
- 238000007711 solidification Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XPMMAKUHNMSONL-UHFFFAOYSA-N 6-methylpiperidin-2-one Chemical compound CC1CCCC(=O)N1 XPMMAKUHNMSONL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000011538 cleaning material Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000009423 ventilation Methods 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0036—Crystallisation on to a bed of product crystals; Seeding
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0059—General arrangements of crystallisation plant, e.g. flow sheets
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH830065A CH450433A (de) | 1965-06-15 | 1965-06-15 | Verfahren zur Reinigung von Lactamen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1695247A1 DE1695247A1 (de) | 1972-05-10 |
| DE1695247B2 DE1695247B2 (de) | 1974-10-03 |
| DE1695247C3 true DE1695247C3 (de) | 1975-05-28 |
Family
ID=4338186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1695247A Expired DE1695247C3 (de) | 1965-06-15 | 1966-06-14 | Verfahren zur Reinigung von Lactamen durch Schmelzkristallisation |
Country Status (7)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2019431C2 (de) * | 1970-04-22 | 1981-10-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigung von Caprolactam |
| CH549020A (de) * | 1970-12-22 | 1974-05-15 | Inventa Ag | Verfahren zur reinigung von lactamen. |
| US3966712A (en) * | 1972-05-19 | 1976-06-29 | Bayer Aktiengesellschaft | Process for the purification of caprolactam |
| US4148792A (en) * | 1976-09-15 | 1979-04-10 | Bayer Aktiengesellschaft | Purification of caprolactam |
| DE2845075A1 (de) * | 1978-10-17 | 1980-05-08 | Basf Ag | Verfahren zur reinigung von rohcaprolactam |
| US4554817A (en) * | 1983-05-10 | 1985-11-26 | Trw Inc. | Valve sleeve shaping method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3145198A (en) * | 1964-08-18 | piija | ||
| US3179657A (en) * | 1965-04-20 | Process for purifying caprolactam | ||
| US2813858A (en) * | 1954-08-26 | 1957-11-19 | Allied Chem & Dye Corp | Process for purifying epsilon-caprolactam |
-
1965
- 1965-06-15 CH CH830065A patent/CH450433A/de unknown
-
1966
- 1966-06-07 US US555739A patent/US3476744A/en not_active Expired - Lifetime
- 1966-06-14 GB GB26557/66A patent/GB1078249A/en not_active Expired
- 1966-06-14 DE DE1695247A patent/DE1695247C3/de not_active Expired
- 1966-06-14 NL NL666608223A patent/NL142953B/xx unknown
- 1966-06-15 BE BE682555D patent/BE682555A/xx unknown
- 1966-06-15 YU YU1125/66A patent/YU31791B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6608223A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-16 |
| US3476744A (en) | 1969-11-04 |
| NL142953B (nl) | 1974-08-15 |
| DE1695247A1 (de) | 1972-05-10 |
| CH450433A (de) | 1968-01-31 |
| BE682555A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-15 |
| DE1695247B2 (de) | 1974-10-03 |
| YU31791B (en) | 1973-12-31 |
| GB1078249A (en) | 1967-08-09 |
| YU112566A (en) | 1973-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |