JPH0212256B2 - - Google Patents
Info
- Publication number
- JPH0212256B2 JPH0212256B2 JP56045368A JP4536881A JPH0212256B2 JP H0212256 B2 JPH0212256 B2 JP H0212256B2 JP 56045368 A JP56045368 A JP 56045368A JP 4536881 A JP4536881 A JP 4536881A JP H0212256 B2 JPH0212256 B2 JP H0212256B2
- Authority
- JP
- Japan
- Prior art keywords
- alkali metal
- range
- aminoalkanoate
- hydrogen sulfide
- lactam
- 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 - Lifetime
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- 229910052783 alkali metal Inorganic materials 0.000 claims description 38
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 28
- -1 alkali metal carboxylate Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 150000001340 alkali metals Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 150000003951 lactams Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 9
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- OFHDZEYCBJGZEF-UHFFFAOYSA-N 1,4-dibromo-2-(4-methylphenyl)benzene Chemical compound C1=CC(C)=CC=C1C1=CC(Br)=CC=C1Br OFHDZEYCBJGZEF-UHFFFAOYSA-N 0.000 description 1
- GHVFWFCIYIGDCX-UHFFFAOYSA-N 1,4-dibromo-2-butyl-5-cyclohexylbenzene Chemical compound C1=C(Br)C(CCCC)=CC(Br)=C1C1CCCCC1 GHVFWFCIYIGDCX-UHFFFAOYSA-N 0.000 description 1
- KZHZSALFKRDIBQ-UHFFFAOYSA-N 1,4-dibromo-2-ethyl-5-propan-2-ylbenzene Chemical compound CCC1=CC(Br)=C(C(C)C)C=C1Br KZHZSALFKRDIBQ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- PTIQIITULDNGAF-UHFFFAOYSA-N 1,4-dichloro-2,3,5,6-tetramethylbenzene Chemical compound CC1=C(C)C(Cl)=C(C)C(C)=C1Cl PTIQIITULDNGAF-UHFFFAOYSA-N 0.000 description 1
- UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 description 1
- WKDOCYUWLREIQL-UHFFFAOYSA-N 1,4-dichloro-2-(3-methylcyclopentyl)-5-octylbenzene Chemical compound C1=C(Cl)C(CCCCCCCC)=CC(Cl)=C1C1CC(C)CC1 WKDOCYUWLREIQL-UHFFFAOYSA-N 0.000 description 1
- KFAKZJUYBOYVKA-UHFFFAOYSA-N 1,4-dichloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Cl KFAKZJUYBOYVKA-UHFFFAOYSA-N 0.000 description 1
- ULYZMNKNGHNAIE-UHFFFAOYSA-N 1,4-diiodo-2-octadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(I)=CC=C1I ULYZMNKNGHNAIE-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- AFNHODZKFRGAOZ-UHFFFAOYSA-N 1-(3-methylphenyl)azetidin-2-one Chemical compound CC1=CC=CC(N2C(CC2)=O)=C1 AFNHODZKFRGAOZ-UHFFFAOYSA-N 0.000 description 1
- AZAMPMUEKXNYFW-UHFFFAOYSA-N 1-[2-(2-oxopyrrolidin-1-yl)ethyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCN1C(=O)CCC1 AZAMPMUEKXNYFW-UHFFFAOYSA-N 0.000 description 1
- GNFCNQUBONBCLF-UHFFFAOYSA-N 1-benzyl-4-(2-methylphenyl)piperidin-2-one Chemical compound CC1=CC=CC=C1C1CC(=O)N(CC=2C=CC=CC=2)CC1 GNFCNQUBONBCLF-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 1
- NNAACTNLZAIIBF-UHFFFAOYSA-N 1-cyclopentyl-4-dodecylpiperidin-2-one Chemical compound O=C1CC(CCCCCCCCCCCC)CCN1C1CCCC1 NNAACTNLZAIIBF-UHFFFAOYSA-N 0.000 description 1
- DXRBTWLMBZCLBV-UHFFFAOYSA-N 1-dodecyl-3-octylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCC(CCCCCCCC)C1=O DXRBTWLMBZCLBV-UHFFFAOYSA-N 0.000 description 1
- VUQMOERHEHTWPE-UHFFFAOYSA-N 1-ethylpiperidin-2-one Chemical compound CCN1CCCCC1=O VUQMOERHEHTWPE-UHFFFAOYSA-N 0.000 description 1
- BWIRRVWVFWVVSG-UHFFFAOYSA-N 1-propan-2-ylazepan-2-one Chemical compound CC(C)N1CCCCCC1=O BWIRRVWVFWVVSG-UHFFFAOYSA-N 0.000 description 1
- YHNQOXAUNKFXNZ-UHFFFAOYSA-N 13-amino-tridecanoic acid Chemical compound NCCCCCCCCCCCCC(O)=O YHNQOXAUNKFXNZ-UHFFFAOYSA-N 0.000 description 1
- DPQQGJPGOOUTQS-UHFFFAOYSA-M 13-aminotridecanoate;rubidium(1+) Chemical compound [Rb+].NCCCCCCCCCCCCC([O-])=O DPQQGJPGOOUTQS-UHFFFAOYSA-M 0.000 description 1
- YDUZJJVOMVPPMD-UHFFFAOYSA-N 2,5-dichloro-1-dodecyl-3-hexylbenzene Chemical compound CCCCCCCCCCCCC1=CC(Cl)=CC(CCCCCC)=C1Cl YDUZJJVOMVPPMD-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical compound CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 description 1
- RDFMDVXONNIGBC-UHFFFAOYSA-N 2-aminoheptanoic acid Chemical compound CCCCCC(N)C(O)=O RDFMDVXONNIGBC-UHFFFAOYSA-N 0.000 description 1
- ZXONXKTYRSSVKY-UHFFFAOYSA-N 2-benzyl-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(CC=2C=CC=CC=2)=C1 ZXONXKTYRSSVKY-UHFFFAOYSA-N 0.000 description 1
- FGSUUFDRDVJCLT-UHFFFAOYSA-N 3-methylazepan-2-one Chemical compound CC1CCCCNC1=O FGSUUFDRDVJCLT-UHFFFAOYSA-N 0.000 description 1
- BNWOFLCLCRHUTF-UHFFFAOYSA-N 3-phenylpyrrolidin-2-one Chemical compound O=C1NCCC1C1=CC=CC=C1 BNWOFLCLCRHUTF-UHFFFAOYSA-N 0.000 description 1
- AHTSYKFOEHCRTI-UHFFFAOYSA-N 4-benzyl-3-butyl-1-phenylpyrrolidin-2-one Chemical compound C1N(C=2C=CC=CC=2)C(=O)C(CCCC)C1CC1=CC=CC=C1 AHTSYKFOEHCRTI-UHFFFAOYSA-N 0.000 description 1
- SHJDOXMERQRWDJ-UHFFFAOYSA-N 4-bromo-1-chloro-2-phenylbenzene Chemical compound ClC1=CC=C(Br)C=C1C1=CC=CC=C1 SHJDOXMERQRWDJ-UHFFFAOYSA-N 0.000 description 1
- BDEZUJWXOXUYFB-UHFFFAOYSA-M 6-aminohexanoate;rubidium(1+) Chemical compound [Rb+].NCCCCCC([O-])=O BDEZUJWXOXUYFB-UHFFFAOYSA-M 0.000 description 1
- RSTNUXHTAATHED-UHFFFAOYSA-N 8-(butylamino)-4-cyclohexyl-7-methyloctanoic acid Chemical compound CCCCNCC(C)CCC(CCC(O)=O)C1CCCCC1 RSTNUXHTAATHED-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- VHRZOOAZTLUOJP-UHFFFAOYSA-N amino heptanoate Chemical compound CCCCCCC(=O)ON VHRZOOAZTLUOJP-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- YLSVAXPSKWYQRN-UHFFFAOYSA-M cesium;4-amino-2-phenylbutanoate Chemical compound [Cs+].NCCC(C([O-])=O)C1=CC=CC=C1 YLSVAXPSKWYQRN-UHFFFAOYSA-M 0.000 description 1
- XETQKEIVAJQNEY-UHFFFAOYSA-M cesium;5-(ethylamino)pentanoate Chemical compound [Cs+].CCNCCCCC([O-])=O XETQKEIVAJQNEY-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- KVQGGLZHHFGHPU-UHFFFAOYSA-N methyl 4-aminobutanoate Chemical compound COC(=O)CCCN KVQGGLZHHFGHPU-UHFFFAOYSA-N 0.000 description 1
- ZYKOKVARXPKXFW-UHFFFAOYSA-N methyl 8-aminooctanoate Chemical compound COC(=O)CCCCCCCN ZYKOKVARXPKXFW-UHFFFAOYSA-N 0.000 description 1
- KAONDSIEAGDWKS-UHFFFAOYSA-N n,n-dipropylbutanamide Chemical compound CCCN(CCC)C(=O)CCC KAONDSIEAGDWKS-UHFFFAOYSA-N 0.000 description 1
- ABMDIECEEGFXNC-UHFFFAOYSA-N n-ethylpropanamide Chemical compound CCNC(=O)CC ABMDIECEEGFXNC-UHFFFAOYSA-N 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- PYIYRSAWFUKGQV-UHFFFAOYSA-M potassium;10-aminodecanoate Chemical compound [K+].NCCCCCCCCCC([O-])=O PYIYRSAWFUKGQV-UHFFFAOYSA-M 0.000 description 1
- SHXKMVBVWZYJFB-UHFFFAOYSA-M potassium;2-[2-(dodecylamino)ethyl]decanoate Chemical compound [K+].CCCCCCCCCCCCNCCC(C([O-])=O)CCCCCCCC SHXKMVBVWZYJFB-UHFFFAOYSA-M 0.000 description 1
- RXJJXODXVBSUDF-UHFFFAOYSA-M potassium;5-(benzylamino)-3-(2-methylphenyl)pentanoate Chemical compound [K+].CC1=CC=CC=C1C(CC([O-])=O)CCNCC1=CC=CC=C1 RXJJXODXVBSUDF-UHFFFAOYSA-M 0.000 description 1
- DODZTDPBCYADAL-UHFFFAOYSA-M potassium;5-aminopentanoate Chemical compound [K+].NCCCCC([O-])=O DODZTDPBCYADAL-UHFFFAOYSA-M 0.000 description 1
- XDAZXKSWOLXGPP-UHFFFAOYSA-M potassium;6-(propan-2-ylamino)hexanoate Chemical compound [K+].CC(C)NCCCCCC([O-])=O XDAZXKSWOLXGPP-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- RNNVQUQHVWAPPN-UHFFFAOYSA-M sodium;3-[2-(cyclopentylamino)ethyl]pentadecanoate Chemical compound [Na+].CCCCCCCCCCCCC(CC([O-])=O)CCNC1CCCC1 RNNVQUQHVWAPPN-UHFFFAOYSA-M 0.000 description 1
- QKJPFZCCZMBRFB-UHFFFAOYSA-M sodium;3-aminopropanoate Chemical compound [Na+].NCCC([O-])=O QKJPFZCCZMBRFB-UHFFFAOYSA-M 0.000 description 1
- PDMUBVHXTYNLDT-UHFFFAOYSA-M sodium;4-(methylamino)butanoate Chemical compound [Na+].CNCCCC([O-])=O PDMUBVHXTYNLDT-UHFFFAOYSA-M 0.000 description 1
- MJGIKHNOXNRIHX-UHFFFAOYSA-M sodium;4-aminobutanoate Chemical compound [Na+].NCCCC([O-])=O MJGIKHNOXNRIHX-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0272—Preparatory processes using other sulfur sources
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/147,407 US4324886A (en) | 1980-05-06 | 1980-05-06 | Arylene sulfide polymer prepared from aminoalkanoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572250A JPS572250A (en) | 1982-01-07 |
| JPH0212256B2 true JPH0212256B2 (en]) | 1990-03-19 |
Family
ID=22521458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4536881A Granted JPS572250A (en) | 1980-05-06 | 1981-03-27 | Alkali metal aminoalkanoate and manufacture of polymer therewith |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4324886A (en]) |
| EP (1) | EP0039508B1 (en]) |
| JP (1) | JPS572250A (en]) |
| CA (1) | CA1191860A (en]) |
| DE (1) | DE3162489D1 (en]) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03126456U (en]) * | 1990-04-02 | 1991-12-19 | ||
| JPH0433356U (en]) * | 1990-07-12 | 1992-03-18 | ||
| WO2021193226A1 (ja) | 2020-03-27 | 2021-09-30 | Dic株式会社 | ラミネート方法及びラミネート装置 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4393197A (en) * | 1982-02-16 | 1983-07-12 | Phillips Petroleum Company | Arylene sulfide polymer preparation |
| JPS617332A (ja) * | 1984-06-20 | 1986-01-14 | Kureha Chem Ind Co Ltd | 高分子量ポリアリ−レンスルフイドの製造法 |
| DE3428985A1 (de) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen, gegebenenfalls verzweigten polyarylensulfiden |
| JPH0643489B2 (ja) * | 1986-02-14 | 1994-06-08 | 呉羽化学工業株式会社 | 安定性の高いポリアリ−レンチオエ−テルの製造法 |
| JPH01132633A (ja) * | 1987-09-29 | 1989-05-25 | Phillips Petroleum Co | 芳香族スルフィド／スルホンポリマーの製造方法 |
| US5086163A (en) * | 1987-09-29 | 1992-02-04 | Phillips Petroleum Company | Aromatic sulfide/sulfone polymer production |
| US5110902A (en) * | 1987-09-29 | 1992-05-05 | Phillips Petroleum Company | Aromatic sulfide/sulfone polymer production with complex of alkali metal hydrosulfide and alkali metal amino alkanoate |
| US5015725A (en) * | 1987-09-29 | 1991-05-14 | Phillips Petroleum Company | Aromatic sulfide/sulfone polymer production |
| JP2575430B2 (ja) * | 1987-12-18 | 1997-01-22 | 東ソー株式会社 | ポリ（ｐ−フェニレンスルフィド）の製造方法 |
| CA1337231C (en) * | 1987-12-24 | 1995-10-03 | Toso Susteel Co., Ltd. | Process for producing poly (para-phenylenesulfide) |
| MY104185A (en) * | 1988-08-31 | 1994-02-28 | Idemitsu Petrochemical Company Ltd | A process for preparing polyarylene sulfides |
| DE4105748A1 (de) * | 1991-02-23 | 1992-08-27 | Bayer Ag | Verfahren zur herstellung von polyarylensulfiden |
| JPH05202189A (ja) * | 1991-09-23 | 1993-08-10 | Phillips Petroleum Co | アリーレンスルフィドポリマーの調製方法 |
| JP3177755B2 (ja) * | 1992-07-10 | 2001-06-18 | 出光石油化学株式会社 | Ｎ−メチルアミノ酪酸リチウムの製造方法 |
| US20020183481A1 (en) * | 1999-12-30 | 2002-12-05 | Vidaurri Fernando C. | Method to decrease corrosiveness of reactants in poly(arylene sulfide) polymer production |
| WO2004060972A1 (ja) * | 2002-12-27 | 2004-07-22 | Kureha Chemical Industry Company, Limited | ポリアリーレンスルフィド及びその製造方法 |
| US7312300B2 (en) * | 2005-02-22 | 2007-12-25 | Chevron Phillips Chemical Company Lp | Inferred water analysis in polyphenylene sulfide production |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE820439C (de) * | 1946-05-24 | 1951-11-12 | Basf Ag | Verfahren zur Herstellung von Aminocarbonsaeuren aus ihren Lactamen |
| NL127988C (en]) * | 1965-06-04 | |||
| US3919177A (en) * | 1973-11-19 | 1975-11-11 | Phillips Petroleum Co | P-phenylene sulfide polymers |
| US3867356A (en) * | 1973-11-19 | 1975-02-18 | Phillips Petroleum Co | Arylene sulfide polymers |
| US3884884A (en) * | 1973-11-20 | 1975-05-20 | Phillips Petroleum Co | Arylene sulfide polymers |
| US4064114A (en) * | 1975-05-27 | 1977-12-20 | Phillips Petroleum Company | Production of arylene sulfide polymers |
| US4060520A (en) * | 1976-03-30 | 1977-11-29 | Phillips Petroleum Company | Continuous reaction for preparation of arylene sulfide polymer |
-
1980
- 1980-05-06 US US06/147,407 patent/US4324886A/en not_active Expired - Lifetime
-
1981
- 1981-03-27 JP JP4536881A patent/JPS572250A/ja active Granted
- 1981-04-09 CA CA000375126A patent/CA1191860A/en not_active Expired
- 1981-05-05 DE DE8181103387T patent/DE3162489D1/de not_active Expired
- 1981-05-05 EP EP81103387A patent/EP0039508B1/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03126456U (en]) * | 1990-04-02 | 1991-12-19 | ||
| JPH0433356U (en]) * | 1990-07-12 | 1992-03-18 | ||
| WO2021193226A1 (ja) | 2020-03-27 | 2021-09-30 | Dic株式会社 | ラミネート方法及びラミネート装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3162489D1 (en) | 1984-04-12 |
| CA1191860A (en) | 1985-08-13 |
| EP0039508A1 (en) | 1981-11-11 |
| JPS572250A (en) | 1982-01-07 |
| EP0039508B1 (en) | 1984-03-07 |
| US4324886A (en) | 1982-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0212256B2 (en]) | ||
| US4786711A (en) | P-phenylene sulfide polymer preparation with dehydrated mixture of alkali metal hydroxide and excess alkali metal bisulfide | |
| US4064114A (en) | Production of arylene sulfide polymers | |
| JP3568054B2 (ja) | ポリフェニレンスルフィドの製造方法 | |
| US4096132A (en) | Production of p-phenylene sulfide polymers | |
| US4038259A (en) | Production of p-phenylene sulfide polymers | |
| US4039518A (en) | Production of p-phenylene sulfide polymers | |
| US5438115A (en) | Process for preparing poly(arylene sulfide) polymers | |
| US5239050A (en) | Process for preparing arylene sulfide polymer with addition of aqueous alkali metal carboxylate prior to termination of polymerization | |
| US4820800A (en) | Arylene sulfide polymers | |
| KR20110086702A (ko) | 폴리아릴렌설피드 수지의 제조 방법 | |
| CA1087348A (en) | Production of arylene sulfide polymers | |
| US4393197A (en) | Arylene sulfide polymer preparation | |
| EP0287009A1 (en) | Process for preparing poly(arylene sulfide ketone) with water addition | |
| EP0086487B1 (en) | Arylene sulfide polymer preparation | |
| US5175243A (en) | Process for preparing arylene sulfide polymers with halo benzene containing deactivating group | |
| JPS59215323A (ja) | ポリアリ−レンサルフアイドの製造法 | |
| US3790536A (en) | Arylene sulfide polymer process | |
| US4371706A (en) | Preparation of alkali metal aminoalkanoates | |
| US5037952A (en) | Process for the production of high molecular weight, optionally branched polyarylene sulfides | |
| US4464507A (en) | Process for the production of high molecular weight, optionally branched, polyarylene sulphides | |
| US3940375A (en) | Arylene sulfide polymers | |
| JP3023924B2 (ja) | カルボキシル基含有アリーレンスルフィド系共重合体の製造方法 | |
| JPS58152020A (ja) | 高分子量の分枝状ポリアリ−レンサルフアイド類の製造方法 | |
| US5237046A (en) | Process for stabilizing the molecular weight of linear or optionally branched polyarylene sulfides |