TWI565516B - 以膜處理來回收己內醯胺之技術 - Google Patents
以膜處理來回收己內醯胺之技術 Download PDFInfo
- Publication number
- TWI565516B TWI565516B TW099144493A TW99144493A TWI565516B TW I565516 B TWI565516 B TW I565516B TW 099144493 A TW099144493 A TW 099144493A TW 99144493 A TW99144493 A TW 99144493A TW I565516 B TWI565516 B TW I565516B
- Authority
- TW
- Taiwan
- Prior art keywords
- caprolactam
- membrane
- permeate
- aqueous solution
- weight
- Prior art date
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 212
- 239000012528 membrane Substances 0.000 title claims description 127
- 238000011084 recovery Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 86
- 239000012466 permeate Substances 0.000 claims description 62
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 49
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 49
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 49
- 239000012535 impurity Substances 0.000 claims description 42
- 239000007864 aqueous solution Substances 0.000 claims description 36
- 239000012465 retentate Substances 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 17
- 239000012530 fluid Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000001166 ammonium sulphate Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 230000000717 retained effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000011045 prefiltration Methods 0.000 claims description 3
- 238000000108 ultra-filtration Methods 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- XBUFCZMOAHHGMX-UHFFFAOYSA-N hydroxylamine;phosphoric acid Chemical compound ON.ON.ON.OP(O)(O)=O XBUFCZMOAHHGMX-UHFFFAOYSA-N 0.000 claims description 2
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 238000010979 pH adjustment Methods 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000001728 nano-filtration Methods 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 150000002894 organic compounds Chemical class 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 230000004907 flux Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002699 waste material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000001741 organic sulfur group Chemical group 0.000 description 5
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- -1 polypropylene Polymers 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009295 crossflow filtration Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- MKAFBCFSDHPPNP-UHFFFAOYSA-N decylazanium hydrogen sulfate Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCC)N MKAFBCFSDHPPNP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/14—Preparation of salts or adducts of lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09179903 | 2009-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201129418A TW201129418A (en) | 2011-09-01 |
| TWI565516B true TWI565516B (zh) | 2017-01-11 |
Family
ID=42174487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099144493A TWI565516B (zh) | 2009-12-18 | 2010-12-17 | 以膜處理來回收己內醯胺之技術 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20130211072A1 (enExample) |
| EP (1) | EP2513050A2 (enExample) |
| JP (1) | JP2013514335A (enExample) |
| KR (1) | KR101810704B1 (enExample) |
| CN (1) | CN102666483A (enExample) |
| EA (1) | EA201200915A1 (enExample) |
| IN (1) | IN2012DN05159A (enExample) |
| TW (1) | TWI565516B (enExample) |
| WO (1) | WO2011073400A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104071948B (zh) * | 2014-06-25 | 2016-04-27 | 江苏久吾高科技股份有限公司 | 一种利用膜技术处理己内酰胺废水的方法及装置 |
| CN108341763B (zh) * | 2018-04-24 | 2020-12-01 | 河北美邦工程科技股份有限公司 | 一种己内酰胺结晶纯化方法 |
| CN110964492B (zh) * | 2018-09-29 | 2022-04-12 | 中国石油化工股份有限公司 | 一种溶硫剂及其制备方法和应用 |
| CN114805207A (zh) * | 2022-04-14 | 2022-07-29 | 山东华鲁恒升化工股份有限公司 | 一种利用膜分离技术除去重排液中硫酸的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW408109B (en) * | 1997-04-29 | 2000-10-11 | Dsm Nv | Process for recovering caprolactam from a neutralized rearrangement mixture |
| CN101570503A (zh) * | 2008-11-11 | 2009-11-04 | 广东新会美达锦纶股份有限公司 | 一种低浓度己内酰胺水溶液的浓缩方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS523261A (en) | 1975-06-24 | 1977-01-11 | Sumitomo Chem Co Ltd | Purification method for polluted water |
| JPS59115704A (ja) | 1982-12-24 | 1984-07-04 | Toray Ind Inc | 半透膜の処理法 |
| NL1011936C2 (nl) * | 1999-04-29 | 2000-10-31 | Dsm Nv | Werkwijze voor het bereiden van caprolactam. |
| PL206266B1 (pl) | 2001-03-01 | 2010-07-30 | Dsm Ip Assets Bvdsm Ip Assets Bv | Sposób odzyskiwania i oczyszczania kaprolaktamu z rozpuszczalnika organicznego |
-
2010
- 2010-12-17 KR KR1020127018141A patent/KR101810704B1/ko active Active
- 2010-12-17 JP JP2012543794A patent/JP2013514335A/ja not_active Withdrawn
- 2010-12-17 US US13/516,296 patent/US20130211072A1/en not_active Abandoned
- 2010-12-17 IN IN5159DEN2012 patent/IN2012DN05159A/en unknown
- 2010-12-17 TW TW099144493A patent/TWI565516B/zh active
- 2010-12-17 WO PCT/EP2010/070097 patent/WO2011073400A2/en not_active Ceased
- 2010-12-17 EP EP10795353A patent/EP2513050A2/en not_active Withdrawn
- 2010-12-17 EA EA201200915A patent/EA201200915A1/ru unknown
- 2010-12-17 CN CN2010800579438A patent/CN102666483A/zh active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW408109B (en) * | 1997-04-29 | 2000-10-11 | Dsm Nv | Process for recovering caprolactam from a neutralized rearrangement mixture |
| CN101570503A (zh) * | 2008-11-11 | 2009-11-04 | 广东新会美达锦纶股份有限公司 | 一种低浓度己内酰胺水溶液的浓缩方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101810704B1 (ko) | 2017-12-19 |
| CN102666483A (zh) | 2012-09-12 |
| JP2013514335A (ja) | 2013-04-25 |
| EP2513050A2 (en) | 2012-10-24 |
| US20130211072A1 (en) | 2013-08-15 |
| EA201200915A1 (ru) | 2012-12-28 |
| WO2011073400A2 (en) | 2011-06-23 |
| IN2012DN05159A (enExample) | 2015-10-23 |
| WO2011073400A3 (en) | 2011-09-09 |
| KR20120112544A (ko) | 2012-10-11 |
| TW201129418A (en) | 2011-09-01 |
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