RU2215754C2 - Способ получения полиамидов из соединений аминокарбоновой кислоты - Google Patents
Способ получения полиамидов из соединений аминокарбоновой кислоты Download PDFInfo
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- RU2215754C2 RU2215754C2 RU2000124663/04A RU2000124663A RU2215754C2 RU 2215754 C2 RU2215754 C2 RU 2215754C2 RU 2000124663/04 A RU2000124663/04 A RU 2000124663/04A RU 2000124663 A RU2000124663 A RU 2000124663A RU 2215754 C2 RU2215754 C2 RU 2215754C2
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- RU
- Russia
- Prior art keywords
- acid
- pressure
- aminocaproic acid
- reaction mixture
- mixture
- Prior art date
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 34
- 229920002647 polyamide Polymers 0.000 title claims abstract description 34
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 239000011541 reaction mixture Substances 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- -1 ceroxide Chemical compound 0.000 claims abstract description 29
- 239000007791 liquid phase Substances 0.000 claims abstract description 21
- 125000005219 aminonitrile group Chemical group 0.000 claims abstract description 20
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 19
- 239000012071 phase Substances 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims abstract description 12
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 11
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 11
- 239000010457 zeolite Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000945 filler Substances 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 4
- 150000004760 silicates Chemical class 0.000 claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 claims abstract description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052845 zircon Inorganic materials 0.000 claims abstract description 3
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 15
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 10
- 229960002684 aminocaproic acid Drugs 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical group O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 5
- AKVAIQVGWQLMBG-UHFFFAOYSA-N 6-amino-n,n-diethylhexanamide Chemical compound CCN(CC)C(=O)CCCCCN AKVAIQVGWQLMBG-UHFFFAOYSA-N 0.000 claims description 3
- JYYXVDYYEXMEJU-UHFFFAOYSA-N 6-amino-n,n-dimethylhexanamide Chemical compound CN(C)C(=O)CCCCCN JYYXVDYYEXMEJU-UHFFFAOYSA-N 0.000 claims description 3
- BUSHYIBZUMHUEU-UHFFFAOYSA-N 6-amino-n-methylhexanamide Chemical compound CNC(=O)CCCCCN BUSHYIBZUMHUEU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- NJNQDCIAOXIFTB-UHFFFAOYSA-N ethyl 6-aminohexanoate Chemical compound CCOC(=O)CCCCCN NJNQDCIAOXIFTB-UHFFFAOYSA-N 0.000 claims description 3
- TZJVWRXHKAXSEA-UHFFFAOYSA-N methyl 6-aminohexanoate Chemical compound COC(=O)CCCCCN TZJVWRXHKAXSEA-UHFFFAOYSA-N 0.000 claims description 3
- GXQFDPRUJPBDFB-UHFFFAOYSA-N 6-amino-n-ethylhexanamide Chemical compound CCNC(=O)CCCCCN GXQFDPRUJPBDFB-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- ZLHYDRXTDZFRDZ-UHFFFAOYSA-N epsilon-aminocaproamide Chemical compound NCCCCCC(N)=O ZLHYDRXTDZFRDZ-UHFFFAOYSA-N 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 description 21
- 239000000047 product Substances 0.000 description 18
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- 239000000049 pigment Substances 0.000 description 14
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 12
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
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- 239000000975 dye Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19808490.0 | 1998-02-27 | ||
| DE19808490A DE19808490A1 (de) | 1998-02-27 | 1998-02-27 | Verfahren zur Herstellung von Polyamiden aus Aminocarbonsäureverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2000124663A RU2000124663A (ru) | 2002-08-27 |
| RU2215754C2 true RU2215754C2 (ru) | 2003-11-10 |
Family
ID=7859221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2000124663/04A RU2215754C2 (ru) | 1998-02-27 | 1999-02-23 | Способ получения полиамидов из соединений аминокарбоновой кислоты |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6362307B1 (enExample) |
| EP (1) | EP1056798B1 (enExample) |
| JP (1) | JP2002504606A (enExample) |
| KR (1) | KR100552372B1 (enExample) |
| CN (1) | CN1175027C (enExample) |
| AR (1) | AR018276A1 (enExample) |
| AU (1) | AU2928399A (enExample) |
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| CA (1) | CA2322035A1 (enExample) |
| CZ (1) | CZ292892B6 (enExample) |
| DE (2) | DE19808490A1 (enExample) |
| ES (1) | ES2182496T3 (enExample) |
| ID (1) | ID25452A (enExample) |
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| UA (1) | UA54586C2 (enExample) |
| WO (1) | WO1999043734A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19846014A1 (de) | 1998-10-06 | 2000-04-13 | Basf Ag | Beschleuniger für die Herstellung von Polyamiden aus Aminonitrilen |
| HUP0105495A2 (en) * | 1999-02-11 | 2002-05-29 | Basf Ag | Method for producing polyamide 6 of a low extract content, high viscosity stability and low remonomerization rate |
| NL1013939C2 (nl) * | 1999-12-23 | 2001-06-26 | Dsm Nv | Werkwijze voor de bereiding van een polyamide. |
| US6807503B2 (en) * | 2002-11-04 | 2004-10-19 | Brion Technologies, Inc. | Method and apparatus for monitoring integrated circuit fabrication |
| US6875838B2 (en) * | 2003-04-28 | 2005-04-05 | Invista North Americal S.A.R.L. | Process for reducing caprolactam and its oligomers in nylon-6 pre-polymer |
| US7754825B2 (en) * | 2005-02-03 | 2010-07-13 | E. I. Du Pont De Nemours And Company | Light stabilized copolyetherester compositions |
| EP3060597A4 (en) * | 2013-10-22 | 2017-06-14 | Empire Technology Development LLC | Compounds and methods for producing nylon 6 |
| US9988491B2 (en) | 2013-10-22 | 2018-06-05 | Empire Technology Development Llc | Methods and compounds for producing nylon 6,6 |
| US10131610B2 (en) | 2013-10-25 | 2018-11-20 | Empire Technology Development Llc | Methods of producing dicarbonyl compounds |
| FR3013356B1 (fr) * | 2013-11-15 | 2018-03-16 | Arkema France | Procede de synthese de polyamide |
| WO2019067517A1 (en) | 2017-09-28 | 2019-04-04 | E. I. Du Pont De Nemours And Company | POLYMERIZATION PROCESS |
| CN108691026B (zh) * | 2018-04-26 | 2020-10-20 | 东华大学 | 一种近红外光结构诱导牵伸制备高强度聚酰胺纤维的制备方法 |
| CN111122720B (zh) * | 2019-12-11 | 2022-09-02 | 湖北三宁碳磷基新材料产业技术研究院有限公司 | 己内酰胺、6-氨基己酰胺和6-氨基己腈的分析方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245129A (en) | 1935-01-02 | 1941-06-10 | Du Pont | Process for preparing linear polyamides |
| US4568736A (en) | 1984-09-17 | 1986-02-04 | The Standard Oil Company | Preparation of polyamide from omega-aminonitrile with oxygen containing phosphorus catalyst |
| DE3534817A1 (de) * | 1985-09-30 | 1987-04-02 | Davy Mckee Ag | Verfahren zur herstellung von polyamid |
| DE4339648A1 (de) | 1993-11-20 | 1995-05-24 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
| DE4443125A1 (de) | 1994-12-03 | 1996-06-05 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
| ES2187826T3 (es) * | 1996-08-30 | 2003-06-16 | Basf Ag | Procedimiento para la obtencion de poliamidas a partir de aminonitrilos. |
| WO1999012993A1 (en) * | 1997-09-05 | 1999-03-18 | Dupont Canada Inc. | Manufacture of branched polyamides |
-
1998
- 1998-02-27 DE DE19808490A patent/DE19808490A1/de not_active Withdrawn
-
1999
- 1999-01-21 TW TW088100866A patent/TWI238835B/zh not_active IP Right Cessation
- 1999-02-03 MY MYPI99000378A patent/MY123297A/en unknown
- 1999-02-08 AR ARP990100516A patent/AR018276A1/es unknown
- 1999-02-23 CZ CZ20003102A patent/CZ292892B6/cs not_active IP Right Cessation
- 1999-02-23 WO PCT/EP1999/001169 patent/WO1999043734A1/de not_active Ceased
- 1999-02-23 KR KR1020007009507A patent/KR100552372B1/ko not_active Expired - Fee Related
- 1999-02-23 BR BR9908282-9A patent/BR9908282A/pt not_active Application Discontinuation
- 1999-02-23 PL PL99342622A patent/PL342622A1/xx unknown
- 1999-02-23 EP EP99910264A patent/EP1056798B1/de not_active Expired - Lifetime
- 1999-02-23 AU AU29283/99A patent/AU2928399A/en not_active Abandoned
- 1999-02-23 DE DE59902118T patent/DE59902118D1/de not_active Expired - Lifetime
- 1999-02-23 CN CNB998033987A patent/CN1175027C/zh not_active Expired - Fee Related
- 1999-02-23 CA CA002322035A patent/CA2322035A1/en not_active Abandoned
- 1999-02-23 TR TR2000/02501T patent/TR200002501T2/xx unknown
- 1999-02-23 JP JP2000533480A patent/JP2002504606A/ja not_active Withdrawn
- 1999-02-23 ID IDW20001642A patent/ID25452A/id unknown
- 1999-02-23 RU RU2000124663/04A patent/RU2215754C2/ru not_active IP Right Cessation
- 1999-02-23 UA UA2000095528A patent/UA54586C2/uk unknown
- 1999-02-23 US US09/622,337 patent/US6362307B1/en not_active Expired - Lifetime
- 1999-02-23 ES ES99910264T patent/ES2182496T3/es not_active Expired - Lifetime
- 1999-02-23 SK SK1163-2000A patent/SK11632000A3/sk unknown
-
2000
- 2000-08-17 BG BG104700A patent/BG104700A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE19808490A1 (de) | 1999-09-02 |
| EP1056798A1 (de) | 2000-12-06 |
| CN1175027C (zh) | 2004-11-10 |
| CN1292010A (zh) | 2001-04-18 |
| CZ20003102A3 (cs) | 2000-12-13 |
| WO1999043734A1 (de) | 1999-09-02 |
| US6362307B1 (en) | 2002-03-26 |
| PL342622A1 (en) | 2001-06-18 |
| JP2002504606A (ja) | 2002-02-12 |
| ID25452A (id) | 2000-10-05 |
| KR20010041382A (ko) | 2001-05-15 |
| TWI238835B (en) | 2005-09-01 |
| EP1056798B1 (de) | 2002-07-24 |
| BG104700A (en) | 2001-09-28 |
| MY123297A (en) | 2006-05-31 |
| CA2322035A1 (en) | 1999-09-02 |
| UA54586C2 (uk) | 2003-03-17 |
| SK11632000A3 (sk) | 2001-04-09 |
| BR9908282A (pt) | 2000-10-31 |
| CZ292892B6 (cs) | 2003-12-17 |
| TR200002501T2 (tr) | 2001-02-21 |
| ES2182496T3 (es) | 2003-03-01 |
| AU2928399A (en) | 1999-09-15 |
| DE59902118D1 (de) | 2002-08-29 |
| KR100552372B1 (ko) | 2006-02-16 |
| AR018276A1 (es) | 2001-11-14 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20060224 |