SK279708B6 - Spôsob získavania kaprolaktámu zo zmiešaných odpad - Google Patents
Spôsob získavania kaprolaktámu zo zmiešaných odpad Download PDFInfo
- Publication number
- SK279708B6 SK279708B6 SK665-93A SK66593A SK279708B6 SK 279708 B6 SK279708 B6 SK 279708B6 SK 66593 A SK66593 A SK 66593A SK 279708 B6 SK279708 B6 SK 279708B6
- Authority
- SK
- Slovakia
- Prior art keywords
- polycaprolactam
- acid
- caprolactam
- depolymerization
- waste
- Prior art date
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000010812 mixed waste Substances 0.000 title claims description 12
- 229920002292 Nylon 6 Polymers 0.000 claims abstract description 61
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 239000002699 waste material Substances 0.000 claims abstract description 23
- 230000002378 acidificating effect Effects 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- -1 polyethylene terephthalate Polymers 0.000 claims description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 9
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 8
- 230000001376 precipitating effect Effects 0.000 abstract description 3
- 230000000593 degrading effect Effects 0.000 abstract description 2
- 239000002198 insoluble material Substances 0.000 abstract 2
- 239000000835 fiber Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000007380 fibre production Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- REKWWOFUJAJBCL-UHFFFAOYSA-L dilithium;hydrogen phosphate Chemical compound [Li+].[Li+].OP([O-])([O-])=O REKWWOFUJAJBCL-UHFFFAOYSA-L 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010800 human waste Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229910001386 lithium phosphate Inorganic materials 0.000 description 1
- SNKMVYBWZDHJHE-UHFFFAOYSA-M lithium;dihydrogen phosphate Chemical compound [Li+].OP(O)([O-])=O SNKMVYBWZDHJHE-UHFFFAOYSA-M 0.000 description 1
- XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000001755 vocal effect Effects 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
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/12—Preparation of lactams by depolymerising polyamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/904,223 US5241066A (en) | 1992-06-25 | 1992-06-25 | Method of recovering caprolactam from mixed waste |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK66593A3 SK66593A3 (en) | 1994-02-02 |
| SK279708B6 true SK279708B6 (sk) | 1999-02-11 |
Family
ID=25418799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK665-93A SK279708B6 (sk) | 1992-06-25 | 1993-06-25 | Spôsob získavania kaprolaktámu zo zmiešaných odpad |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5241066A (cs) |
| EP (1) | EP0575860A1 (cs) |
| AU (1) | AU667916B2 (cs) |
| CA (1) | CA2084865C (cs) |
| CZ (1) | CZ290422B6 (cs) |
| SK (1) | SK279708B6 (cs) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5458740A (en) * | 1994-03-04 | 1995-10-17 | Basf Corporation | Process for the purification of crude caprolactam |
| US5457197A (en) * | 1994-04-08 | 1995-10-10 | Alliedsignal Inc. | Monomer recovery from multi-component materials |
| ATE176786T1 (de) * | 1994-11-08 | 1999-03-15 | Basf Corp | Verfahren zur abtrennung von polymeren aus polymermischungen |
| US5565158A (en) * | 1994-11-16 | 1996-10-15 | Basf Corporation | Process for recycling multicomponent mixed polymer wastes |
| US5849804A (en) * | 1995-06-29 | 1998-12-15 | Basf Corporation | Recovery of polyamides from composite articles |
| US5656757A (en) * | 1995-08-10 | 1997-08-12 | Alliedsignal Inc. | Monomer recovery from multi-component materials |
| US5681952A (en) * | 1995-12-08 | 1997-10-28 | Alliedsignal Inc. | Process for depolymerizing nylon-containing waste to form caprolactam |
| US5698322A (en) * | 1996-12-02 | 1997-12-16 | Kimberly-Clark Worldwide, Inc. | Multicomponent fiber |
| US6140463A (en) * | 1997-02-18 | 2000-10-31 | Stefandl; Roland E. | Process for recycling and recovery of purified nylon polymer |
| US5889142A (en) * | 1997-04-21 | 1999-03-30 | Alliedsignal Inc. | Selective polyamide recovery from multi-component materials |
| US6089009A (en) | 1997-08-28 | 2000-07-18 | Belmont Textile Machinery Co., Inc. | Fluid-jet false-twisting method and product |
| US5990306A (en) * | 1997-09-03 | 1999-11-23 | Alliedsignal Inc. | Process for the purification of caprolactam obtained from the depolymerization of polyamide-containing carpet |
| US6268434B1 (en) | 1997-10-31 | 2001-07-31 | Kimberly Clark Worldwide, Inc. | Biodegradable polylactide nonwovens with improved fluid management properties |
| US5910545A (en) | 1997-10-31 | 1999-06-08 | Kimberly-Clark Worldwide, Inc. | Biodegradable thermoplastic composition |
| US6201068B1 (en) | 1997-10-31 | 2001-03-13 | Kimberly-Clark Worldwide, Inc. | Biodegradable polylactide nonwovens with improved fluid management properties |
| DE19753377B4 (de) * | 1997-12-02 | 2008-07-10 | Lurgi Zimmer Gmbh | Verfahren zur Herstellung von ε-Caprolactam aus Extraktwasser der PA-6-Synthese |
| US6306782B1 (en) | 1997-12-22 | 2001-10-23 | Kimberly-Clark Worldwide, Inc. | Disposable absorbent product having biodisintegratable nonwovens with improved fluid management properties |
| US6544455B1 (en) | 1997-12-22 | 2003-04-08 | Kimberly-Clark Worldwide, Inc. | Methods for making a biodegradable thermoplastic composition |
| US6309988B1 (en) | 1997-12-22 | 2001-10-30 | Kimberly-Clark Worldwide, Inc. | Biodisintegratable nonwovens with improved fluid management properties |
| US6194483B1 (en) | 1998-08-31 | 2001-02-27 | Kimberly-Clark Worldwide, Inc. | Disposable articles having biodegradable nonwovens with improved fluid management properties |
| US6197860B1 (en) | 1998-08-31 | 2001-03-06 | Kimberly-Clark Worldwide, Inc. | Biodegradable nonwovens with improved fluid management properties |
| FR2809395B1 (fr) * | 2000-05-26 | 2002-07-19 | Rhodia Polyamide Intermediates | Procede de purification de lactames |
| US6500897B2 (en) | 2000-12-29 | 2002-12-31 | Kimberly-Clark Worldwide, Inc. | Modified biodegradable compositions and a reactive-extrusion process to make the same |
| US6579934B1 (en) | 2000-12-29 | 2003-06-17 | Kimberly-Clark Worldwide, Inc. | Reactive extrusion process for making modifiied biodegradable compositions |
| US6552124B2 (en) | 2000-12-29 | 2003-04-22 | Kimberly-Clark Worldwide, Inc. | Method of making a polymer blend composition by reactive extrusion |
| US7053151B2 (en) | 2000-12-29 | 2006-05-30 | Kimberly-Clark Worldwide, Inc. | Grafted biodegradable polymer blend compositions |
| US6890989B2 (en) | 2001-03-12 | 2005-05-10 | Kimberly-Clark Worldwide, Inc. | Water-responsive biodegradable polymer compositions and method of making same |
| US20060069170A1 (en) * | 2004-09-27 | 2006-03-30 | Chemical Products Corporation | Decomposition of Polyester |
| US7067613B2 (en) * | 2004-06-04 | 2006-06-27 | Chemical Products Corporation | Separation of polyolefins from nylons |
| US20060070188A1 (en) * | 2004-09-27 | 2006-04-06 | Chemical Products Corporation | Colorant Removal from Polymeric Fibers |
| CN103467378A (zh) * | 2013-09-23 | 2013-12-25 | 福建锦江科技有限公司 | 利用锦纶废丝、下脚料回收生产己内酰胺的工艺方法及磷酸作为催化剂在该方法中的应用 |
| US12410298B2 (en) * | 2021-10-21 | 2025-09-09 | Nan Ya Plastics Corporation | Disposal method for waste fabric containing polyester, nylon, and dye |
| TWI797789B (zh) * | 2021-10-21 | 2023-04-01 | 南亞塑膠工業股份有限公司 | 含聚酯及尼龍的廢棄織物處理方法 |
| US12410299B2 (en) | 2021-10-21 | 2025-09-09 | Nan Ya Plastics Corporation | Disposal method for waste fabric containing polyester, spandex, and dye |
| EP4306585A1 (en) * | 2022-07-11 | 2024-01-17 | Cap Iii B.V. | Process for the recovery of epsilon-caprolactam and polyether polyurethane from polyamide 6 and polyether polyurethane comprising materials |
| WO2025172517A1 (en) | 2024-02-15 | 2025-08-21 | Basf Se | Process for preparing carbon monoxide (co) and molecular hydrogen (h2) from a textile material |
| WO2025172514A1 (en) | 2024-02-15 | 2025-08-21 | Basf Se | Process for preparing carbon monoxide (co) and molecular hydrogen (h2) from a solid material |
| FR3159389A1 (fr) * | 2024-02-16 | 2025-08-22 | Syntetica | Procédé de dépolymérisation du polyamide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3182055A (en) * | 1963-02-18 | 1965-05-04 | Allied Chem | Regeneration of e-caprolactam from polyamides |
| US3317519A (en) * | 1965-05-21 | 1967-05-02 | Allied Chem | Simultaneous depolymerization of polycaproamide and polyester with recovery of caprolactam |
| US5169870A (en) * | 1991-06-21 | 1992-12-08 | Basf Corporation | Reclaiming ε-caprolactam from nylon 6 carpet |
| EP1522235A1 (de) * | 2003-10-08 | 2005-04-13 | Westfalia Profiltechnik GmbH & Co. KG | Führungs- und Laufsystem von Schubladen, Auszügen für Werkstattwagen, Kraftfahrzeugsitzen oder dergleichen Auszugselementen |
-
1992
- 1992-06-25 US US07/904,223 patent/US5241066A/en not_active Expired - Lifetime
- 1992-12-08 CA CA002084865A patent/CA2084865C/en not_active Expired - Fee Related
-
1993
- 1993-06-15 EP EP93109504A patent/EP0575860A1/en not_active Ceased
- 1993-06-21 CZ CZ19931230A patent/CZ290422B6/cs not_active IP Right Cessation
- 1993-06-24 AU AU41495/93A patent/AU667916B2/en not_active Ceased
- 1993-06-25 SK SK665-93A patent/SK279708B6/sk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2084865A1 (en) | 1993-12-26 |
| CA2084865C (en) | 1997-06-03 |
| AU667916B2 (en) | 1996-04-18 |
| US5241066A (en) | 1993-08-31 |
| AU4149593A (en) | 1994-01-06 |
| CZ123093A3 (en) | 1994-02-16 |
| EP0575860A1 (en) | 1993-12-29 |
| CZ290422B6 (cs) | 2002-07-17 |
| SK66593A3 (en) | 1994-02-02 |
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