CA1309404C - Process for purifying caprolactam - Google Patents
Process for purifying caprolactamInfo
- Publication number
- CA1309404C CA1309404C CA000573088A CA573088A CA1309404C CA 1309404 C CA1309404 C CA 1309404C CA 000573088 A CA000573088 A CA 000573088A CA 573088 A CA573088 A CA 573088A CA 1309404 C CA1309404 C CA 1309404C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- caprolactam
- active agent
- comprised
- toluene
- 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 - Fee Related
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title claims abstract description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000004094 surface-active agent Substances 0.000 claims abstract description 16
- 238000009835 boiling Methods 0.000 claims abstract description 13
- 239000006227 byproduct Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 7
- 239000011261 inert gas Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 230000009935 nitrosation Effects 0.000 claims abstract description 5
- 238000007034 nitrosation reaction Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- 230000017105 transposition Effects 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 12
- 238000012856 packing Methods 0.000 claims description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 8
- 238000002485 combustion reaction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical group ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000002699 waste 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
- C07D201/16—Separation or purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21548/87A IT1222419B (it) | 1987-07-31 | 1987-07-31 | Procedimento di purificazione del caprolattame |
| IT21548A/87 | 1987-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1309404C true CA1309404C (en) | 1992-10-27 |
Family
ID=11183439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000573088A Expired - Fee Related CA1309404C (en) | 1987-07-31 | 1988-07-26 | Process for purifying caprolactam |
Country Status (8)
| Country | Link |
|---|---|
| AR (1) | AR244664A1 (enrdf_load_stackoverflow) |
| BR (1) | BR8803787A (enrdf_load_stackoverflow) |
| CA (1) | CA1309404C (enrdf_load_stackoverflow) |
| DE (1) | DE3825524A1 (enrdf_load_stackoverflow) |
| ES (1) | ES2007278A6 (enrdf_load_stackoverflow) |
| IN (1) | IN171456B (enrdf_load_stackoverflow) |
| IT (1) | IT1222419B (enrdf_load_stackoverflow) |
| SU (1) | SU1709905A3 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2781796B1 (fr) † | 1998-07-28 | 2000-09-22 | Rhone Poulenc Fibres | Procede de deshydratation de lactame |
| CN1284774C (zh) * | 2001-08-27 | 2006-11-15 | Dsmip财产有限公司 | 减压蒸馏碱性己内酰胺产物的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1173261B (it) * | 1984-02-08 | 1987-06-18 | Snia Bpd Spa | Procedimento di purificazione del caprolattame |
-
1987
- 1987-07-31 IT IT21548/87A patent/IT1222419B/it active
-
1988
- 1988-07-08 IN IN480/MAS/88A patent/IN171456B/en unknown
- 1988-07-26 CA CA000573088A patent/CA1309404C/en not_active Expired - Fee Related
- 1988-07-27 AR AR88311523A patent/AR244664A1/es active
- 1988-07-27 DE DE3825524A patent/DE3825524A1/de not_active Withdrawn
- 1988-07-29 SU SU884356218A patent/SU1709905A3/ru active
- 1988-07-29 BR BR8803787A patent/BR8803787A/pt not_active IP Right Cessation
- 1988-07-29 ES ES8802389A patent/ES2007278A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR244664A1 (es) | 1993-11-30 |
| SU1709905A3 (ru) | 1992-01-30 |
| DE3825524A1 (de) | 1989-02-09 |
| BR8803787A (pt) | 1989-02-21 |
| ES2007278A6 (es) | 1989-06-01 |
| IN171456B (enrdf_load_stackoverflow) | 1992-10-17 |
| IT8721548A0 (it) | 1987-07-31 |
| IT1222419B (it) | 1990-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |