JPH08502296A - ヘキサメチレンジアミン(及びカプロラクタム)を得るためのナイロン6,6(及び場合により)ナイロン6の解重合 - Google Patents
ヘキサメチレンジアミン(及びカプロラクタム)を得るためのナイロン6,6(及び場合により)ナイロン6の解重合Info
- Publication number
- JPH08502296A JPH08502296A JP6510106A JP51010694A JPH08502296A JP H08502296 A JPH08502296 A JP H08502296A JP 6510106 A JP6510106 A JP 6510106A JP 51010694 A JP51010694 A JP 51010694A JP H08502296 A JPH08502296 A JP H08502296A
- Authority
- JP
- Japan
- Prior art keywords
- nylon
- depolymerization
- caprolactam
- weight
- basic
- 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.)
- Granted
Links
- 229920002292 Nylon 6 Polymers 0.000 title claims abstract description 35
- 229920002302 Nylon 6,6 Polymers 0.000 title claims abstract description 34
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 32
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title description 24
- 229920001778 nylon Polymers 0.000 claims abstract description 22
- 239000004677 Nylon Substances 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 4
- 238000001256 steam distillation Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000002699 waste material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- AKRJQFGOFJIQMW-UHFFFAOYSA-M NC(C(=O)[O-])CCCC.[Na+] Chemical compound NC(C(=O)[O-])CCCC.[Na+] AKRJQFGOFJIQMW-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- CLUHWBURHNNGPK-UHFFFAOYSA-M sodium;6-aminohexanoate Chemical compound [Na+].NCCCCCC([O-])=O CLUHWBURHNNGPK-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement 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
- C07D201/02—Preparation of lactams
- C07D201/12—Preparation of lactams by depolymerising polyamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/14—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with steam or water
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.(a)(i)0〜75重量%のナイロン6及び25〜100重量%のナイ ロン6,6;ならびに(ii)ポリマーの合計重量に基づいて1〜50重量%の 量の塩基性ナイロン解重合触媒を含む溶融ポリマー系を250〜400℃の温度 で確立し; (b)溶融ポリマー系を通って水蒸気を導き; (c)水蒸気を凝縮させて水、カプロラクタム及びヘキサメチレンジアミ ンの混合物を得る 段階を含むナイロン6及びナイロン6,6の混合物を解重合する方法。 2.塩基性ナイロン解重合触媒がアルカリ金属ヒドロキシド及びアルカリ土類 金属ヒドロキシドから成る群より選ばれる請求の範囲第1項に記載の方法。 3.溶融ポリマー系が25〜75重量%のナイロン6及び25〜75重量%の ナイロン6,6を含む請求の範囲第1項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/963,224 | 1992-10-19 | ||
US07/963,224 US5266694A (en) | 1992-10-19 | 1992-10-19 | Nylon component reclamation |
PCT/US1993/009543 WO1994008942A1 (en) | 1992-10-19 | 1993-10-13 | Depolymerization of nylon 6,6 (and optionally) nylon 6 to obtain hexamethylene diamine (and caprolactam) |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH08502296A true JPH08502296A (ja) | 1996-03-12 |
JP3285582B2 JP3285582B2 (ja) | 2002-05-27 |
Family
ID=25506940
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51010694A Expired - Lifetime JP3285582B2 (ja) | 1992-10-19 | 1993-10-13 | ヘキサメチレンジアミン(及びカプロラクタム)を得るためのナイロン6,6(及び場合により)ナイロン6の解重合 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5266694A (ja) |
EP (1) | EP0664787B1 (ja) |
JP (1) | JP3285582B2 (ja) |
AU (1) | AU672062B2 (ja) |
CA (1) | CA2146630C (ja) |
DE (1) | DE69311734T2 (ja) |
ES (1) | ES2104182T3 (ja) |
WO (1) | WO1994008942A1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5457197A (en) * | 1994-04-08 | 1995-10-10 | Alliedsignal Inc. | Monomer recovery from multi-component materials |
US5536831A (en) * | 1994-12-12 | 1996-07-16 | Basf Aktiengesellschaft | Obtaining caprolactam by cleavage of molten polycaprolactam |
KR100316687B1 (ko) * | 1994-12-27 | 2002-02-19 | 전 원 중 | 유기불순물을함유한저순도카프로락탐의정제방법 |
FR2736637B1 (fr) * | 1995-07-12 | 1997-08-22 | Rhone Poulenc Fibres & Polymer | Procede de transformation de polyamides en composes comprenant de l'azote |
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 |
NL1005942C2 (nl) * | 1997-05-01 | 1998-11-03 | Dsm Nv | Depolymeriseren van polyamiden. |
NL1006575C2 (nl) * | 1997-07-14 | 1999-01-15 | Dsm Nv | Depolymeriseren van polyamiden. |
WO2001094457A2 (en) | 2000-06-08 | 2001-12-13 | Dupont Canada Inc. | Solvent-based recovery and recycle of polyamide material |
DE10029422A1 (de) * | 2000-06-15 | 2001-12-20 | Andreas Hornung | Einstufiges Verfahren zur Rückgewinnung von hochreinem epsilon-Caprolactam aus Teppichböden oder Mischfasern |
KR102036265B1 (ko) | 2009-05-07 | 2019-10-24 | 게노마티카 인코포레이티드 | 아디페이트, 헥사메틸렌디아민 및 6-아미노카프로산의 생합성을 위한 미생물 및 방법 |
US8080506B2 (en) * | 2009-07-14 | 2011-12-20 | MSI Technology LLC. | Reactive purge compound for polymer purging |
US11578144B2 (en) | 2018-05-23 | 2023-02-14 | 2569924 Ontario Inc. | Compositions and methods for removing contaminants from plastics processing equipment |
WO2024040143A1 (en) * | 2022-08-19 | 2024-02-22 | Northwestern University | Catalytic chemical recycling of polyamide-based plastics |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE518416A (ja) * | ||||
NL260459A (ja) * | 1960-01-25 | 1964-04-27 | ||
NL283077A (ja) * | 1961-09-12 | |||
US3317519A (en) * | 1965-05-21 | 1967-05-02 | Allied Chem | Simultaneous depolymerization of polycaproamide and polyester with recovery of caprolactam |
JPS53132585A (en) * | 1977-04-21 | 1978-11-18 | Toyobo Co Ltd | Recovery of epsilon-caprolactam |
SE451464B (sv) * | 1981-12-01 | 1987-10-12 | Lumalampan Ab | Forfarande och anordning for atervinning av kvicksilver ur avfall innehallande organiskt material |
US4605762A (en) * | 1982-04-23 | 1986-08-12 | Celanese Mexicana S.A. | Depolymerization of condensation polymers |
DE3502105A1 (de) * | 1985-01-23 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von schiff'schen basen |
CN87101541A (zh) * | 1987-04-21 | 1988-11-02 | 营口县博洛铺助剂厂 | 一种生产己二酸、己二胺盐酸盐技术 |
JPH07131541A (ja) * | 1993-11-02 | 1995-05-19 | Oki Electric Ind Co Ltd | ボイススイッチ |
-
1992
- 1992-10-19 US US07/963,224 patent/US5266694A/en not_active Expired - Lifetime
-
1993
- 1993-10-13 CA CA002146630A patent/CA2146630C/en not_active Expired - Lifetime
- 1993-10-13 ES ES93923278T patent/ES2104182T3/es not_active Expired - Lifetime
- 1993-10-13 DE DE69311734T patent/DE69311734T2/de not_active Expired - Lifetime
- 1993-10-13 AU AU53218/94A patent/AU672062B2/en not_active Expired - Fee Related
- 1993-10-13 JP JP51010694A patent/JP3285582B2/ja not_active Expired - Lifetime
- 1993-10-13 WO PCT/US1993/009543 patent/WO1994008942A1/en active IP Right Grant
- 1993-10-13 EP EP93923278A patent/EP0664787B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
WO1994008942A1 (en) | 1994-04-28 |
AU672062B2 (en) | 1996-09-19 |
JP3285582B2 (ja) | 2002-05-27 |
DE69311734D1 (de) | 1997-07-24 |
US5266694A (en) | 1993-11-30 |
EP0664787B1 (en) | 1997-06-18 |
AU5321894A (en) | 1994-05-09 |
EP0664787A1 (en) | 1995-08-02 |
CA2146630A1 (en) | 1994-04-28 |
CA2146630C (en) | 2003-05-27 |
ES2104182T3 (es) | 1997-10-01 |
DE69311734T2 (de) | 1998-01-15 |
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