CA1176797A - PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta. - Google Patents

PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta.

Info

Publication number: CA1176797A
Authority: CA; Canada
Prior art keywords: beta; carboxylic acid; amides; substituted; acid
Prior art date: 1978-12-27
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

Application number

CA000399458A

Other languages

English (en)

Inventor

Erich Kuster

Bernhard Goossens

Kurt Dahmen

Eduard Barthell

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stockhausen GmbH and Co KG

Original Assignee

Chemische Fabrik Stockhausen GmbH

Priority date (The priority date 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 date listed.)

1978-12-27

Filing date

1982-03-25

Publication date

1984-10-23

1978-12-27 Priority claimed from DE19782856383 external-priority patent/DE2856383C2/de

1979-03-24 Priority claimed from DE19792911642 external-priority patent/DE2911642C2/de

1979-12-27 Priority claimed from CA342,641A external-priority patent/CA1129883A/fr

1982-03-25 Application filed by Chemische Fabrik Stockhausen GmbH filed Critical Chemische Fabrik Stockhausen GmbH

1982-03-25 Priority to CA000399458A priority Critical patent/CA1176797A/fr

1984-10-23 Application granted granted Critical

1984-10-23 Publication of CA1176797A publication Critical patent/CA1176797A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 19
150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 7
238000002360 preparation method Methods 0.000 title abstract description 5
-1 carboxylic acid N-substituted-amides Chemical class 0.000 claims abstract description 35
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 24
230000014759 maintenance of location Effects 0.000 claims abstract description 16
239000000654 additive Substances 0.000 claims abstract description 7
230000003311 flocculating effect Effects 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
238000004062 sedimentation Methods 0.000 claims abstract description 6
239000002480 mineral oil Substances 0.000 claims abstract 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract 2
150000001412 amines Chemical class 0.000 claims description 25
229920001577 copolymer Polymers 0.000 claims description 22
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229920001519 homopolymer Polymers 0.000 claims description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
230000000996 additive effect Effects 0.000 claims description 5
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000005397 methacrylic acid ester group Chemical group 0.000 claims description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
239000010801 sewage sludge Substances 0.000 claims description 2
229920001567 vinyl ester resin Polymers 0.000 claims description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
125000005396 acrylic acid ester group Chemical group 0.000 claims 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
239000001530 fumaric acid Substances 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000011976 maleic acid Substances 0.000 claims 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 7
238000007056 transamidation reaction Methods 0.000 abstract description 7
238000010438 heat treatment Methods 0.000 abstract description 4
150000003141 primary amines Chemical class 0.000 abstract description 4
229920006395 saturated elastomer Polymers 0.000 abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
125000003277 amino group Chemical group 0.000 abstract description 2
239000012808 vapor phase Substances 0.000 abstract description 2
229920006317 cationic polymer Polymers 0.000 abstract 1
238000009835 boiling Methods 0.000 description 26
229940117913 acrylamide Drugs 0.000 description 25
239000000047 product Substances 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 20
238000000034 method Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
150000001408 amides Chemical class 0.000 description 17
239000000178 monomer Substances 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
101150041968 CDC13 gene Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 4
239000000945 filler Substances 0.000 description 4
239000003999 initiator Substances 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000000197 pyrolysis Methods 0.000 description 3
UYDAXZISGMHYGU-VOTSOKGWSA-N (e)-n-[4-(dimethylamino)-3,3-dimethylbutyl]but-2-enamide Chemical compound C\C=C\C(=O)NCCC(C)(C)CN(C)C UYDAXZISGMHYGU-VOTSOKGWSA-N 0.000 description 2
BQTJJGGRUHUVMD-UHFFFAOYSA-N 3-methoxy-2-methylpropanamide Chemical compound COCC(C)C(N)=O BQTJJGGRUHUVMD-UHFFFAOYSA-N 0.000 description 2
BPXCLLWXDHBFRH-UHFFFAOYSA-N 3-methoxypropanamide Chemical compound COCCC(N)=O BPXCLLWXDHBFRH-UHFFFAOYSA-N 0.000 description 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000294754 Macroptilium atropurpureum Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000003926 acrylamides Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000004927 clay Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JUFFRRNJQGSRRA-UHFFFAOYSA-N n-[2-[(dimethylamino)methyl]-2-methylbutyl]-2-methylprop-2-enamide Chemical compound CN(C)CC(C)(CC)CNC(=O)C(C)=C JUFFRRNJQGSRRA-UHFFFAOYSA-N 0.000 description 2
ZZSGYARVLIMPBM-UHFFFAOYSA-N n-[3-(dimethylamino)-2,2-dimethylpropyl]prop-2-enamide Chemical compound CN(C)CC(C)(C)CNC(=O)C=C ZZSGYARVLIMPBM-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
SHKBTNJKIRTXQP-DHZHZOJOSA-N (e)-n-[3-(dibutylamino)-2,2-dimethylpropyl]but-2-enamide Chemical compound CCCCN(CCCC)CC(C)(C)CNC(=O)\C=C\C SHKBTNJKIRTXQP-DHZHZOJOSA-N 0.000 description 1
WGAWKVBOPIUIQS-RMKNXTFCSA-N (e)-n-[3-(diethylamino)-2,2-dimethylpropyl]but-2-enamide Chemical compound CCN(CC)CC(C)(C)CNC(=O)\C=C\C WGAWKVBOPIUIQS-RMKNXTFCSA-N 0.000 description 1
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical class CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
VFPWOMLXNMBLCA-UHFFFAOYSA-N 3-methoxybutanamide Chemical compound COC(C)CC(N)=O VFPWOMLXNMBLCA-UHFFFAOYSA-N 0.000 description 1
ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
HJGSVYJWCCJPBE-VOTSOKGWSA-N C\C=C\C(=O)NCC(C)(C)CN(C)C Chemical compound C\C=C\C(=O)NCC(C)(C)CN(C)C HJGSVYJWCCJPBE-VOTSOKGWSA-N 0.000 description 1
101100135641 Caenorhabditis elegans par-3 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JWOWFSLPFNWGEM-UHFFFAOYSA-N Cl.Cl.NC(=N)C(C)CN=NCC(C)C(N)=N Chemical compound Cl.Cl.NC(=N)C(C)CN=NCC(C)C(N)=N JWOWFSLPFNWGEM-UHFFFAOYSA-N 0.000 description 1
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
229920006063 Lamide® Polymers 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
101100520533 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) un-7 gene Proteins 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
CWBANCVUBCKNAS-UHFFFAOYSA-N [2,2-dimethyl-3-(prop-2-enoylamino)propyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(C)(C)CNC(=O)C=C CWBANCVUBCKNAS-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000008360 acrylonitriles Chemical class 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
XAGFODPZIPBFFR-OUBTZVSYSA-N aluminium-28 atom Chemical compound [28Al] XAGFODPZIPBFFR-OUBTZVSYSA-N 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000007068 beta-elimination reaction Methods 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000002817 coal dust Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000006698 induction Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
ULDIVZQLPBUHAG-UHFFFAOYSA-N n',n',2,2-tetramethylpropane-1,3-diamine Chemical compound CN(C)CC(C)(C)CN ULDIVZQLPBUHAG-UHFFFAOYSA-N 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
DLZVHQZWZNKFAC-UHFFFAOYSA-N n-[3-(dibutylamino)-2,2-dimethylpropyl]prop-2-enamide Chemical compound CCCCN(CCCC)CC(C)(C)CNC(=O)C=C DLZVHQZWZNKFAC-UHFFFAOYSA-N 0.000 description 1
JSOOEKHPRWYXKE-UHFFFAOYSA-N n-[3-(diethylamino)-2,2-dimethylpropyl]-2-methylprop-2-enamide Chemical compound CCN(CC)CC(C)(C)CNC(=O)C(C)=C JSOOEKHPRWYXKE-UHFFFAOYSA-N 0.000 description 1
IBOFFDNDRXEPFG-UHFFFAOYSA-N n-[3-(diethylamino)-2,2-dimethylpropyl]prop-2-enamide Chemical compound CCN(CC)CC(C)(C)CNC(=O)C=C IBOFFDNDRXEPFG-UHFFFAOYSA-N 0.000 description 1
FDHFLHJTOFSAOD-UHFFFAOYSA-N n-[3-(dimethylamino)-2-methyl-2-phenylpropyl]prop-2-enamide Chemical compound C=CC(=O)NCC(C)(CN(C)C)C1=CC=CC=C1 FDHFLHJTOFSAOD-UHFFFAOYSA-N 0.000 description 1
MQGFNNDAXIMEFA-UHFFFAOYSA-N n-[5-(diethylamino)-4,4-dimethylpentyl]prop-2-enamide Chemical compound CCN(CC)CC(C)(C)CCCNC(=O)C=C MQGFNNDAXIMEFA-UHFFFAOYSA-N 0.000 description 1
YZFGDSOEONYTGE-UHFFFAOYSA-N n-[5-(dimethylamino)-4,4-dimethylpentyl]-2-methylprop-2-enamide Chemical compound CN(C)CC(C)(C)CCCNC(=O)C(C)=C YZFGDSOEONYTGE-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000010865 sewage Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000399458A 1978-12-27 1982-03-25 PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta. Expired CA1176797A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000399458A CA1176797A (fr)	1978-12-27	1982-03-25	PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta.

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
DE19782856383 DE2856383C2 (de)	1978-12-27	1978-12-27	Verfahren zur Herstellung von alpha, beta -ungesättigten N-substituierten Säureamiden und ihre Verwendung zur Herstellung von Polymerisaten sowie das N-(2,2-Dimethyl-3-dimethylaminopropyl)-crotonsäureamid
DEP2856383.9		1978-12-27
DE19792911642 DE2911642C2 (de)	1979-03-24	1979-03-24	Verfahren zur Herstellung von α,β-ungesättigten N-substituierten Carbonsäureamiden und ihre Verwendung zur Herstellung von Polymerisaten sowie das N-(N',N',2,2 Tetramethyl-3-aminopropyl)-methacrylamid
DEP2911642.5		1979-03-24
CA342,641A CA1129883A (fr)	1978-12-27	1979-12-27	PREPARATION D'AMIDES SUBST. EN N D'ACIDE CARBOXYLIQUE .alpha.,.beta.-ETHYLENIQUES, ET POLYMERES DERIVES
CA000399458A CA1176797A (fr)	1978-12-27	1982-03-25	PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta.

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA342,641A Division CA1129883A (fr)	1978-12-27	1979-12-27	PREPARATION D'AMIDES SUBST. EN N D'ACIDE CARBOXYLIQUE .alpha.,.beta.-ETHYLENIQUES, ET POLYMERES DERIVES

Publications (1)

Publication Number	Publication Date
CA1176797A true CA1176797A (fr)	1984-10-23

Family

ID=27426209

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000399458A Expired CA1176797A (fr)	1978-12-27	1982-03-25	PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta.

Country Status (1)

Country	Link
CA (1)	CA1176797A (fr)

1982
- 1982-03-25 CA CA000399458A patent/CA1176797A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-10-23	MKEX	Expiry

Publication	Publication Date	Title
CA1129883A (fr)	1982-08-17	PREPARATION D'AMIDES SUBST. EN N D'ACIDE CARBOXYLIQUE .alpha.,.beta.-ETHYLENIQUES, ET POLYMERES DERIVES
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US4702844A (en)	1987-10-27	Flocculants and their use
US4251651A (en)	1981-02-17	Amphoteric polyelectrolyte
US5281340A (en)	1994-01-25	Cationic polymer flocculating agents
JPS6310609A (ja)	1988-01-18	ビニルアミン共重合体およびその製法
JPH05192513A (ja)	1993-08-03	カチオン性高分子凝集剤
US4104226A (en)	1978-08-01	Retention aids and flocculants based on polyacrylamides
US4093542A (en)	1978-06-06	Flocculating agent comprising water-in-oil emulsion of H-active polymer carrying formaldehyde and amine radicals
AU736965B2 (en)	2001-08-09	Use of hydrophilic dispersion polymers for coated broke treatment
US5573675A (en)	1996-11-12	Clarification of deinking process waters using polymers containing vinylamine
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CA1176797A (fr)	1984-10-23	PREPARATION D'ACIDE AMIDO-(SUBSTITUE EN N)- CARBOXYLIQUE INSATURE EN .alpha.,.beta.
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JP4238945B2 (ja)	2009-03-18	製紙用添加剤および紙の製造方法
US5100561A (en)	1992-03-31	Cationic polymers for sludge dewatering
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JP4660896B2 (ja)	2011-03-30	汚泥の脱水方法
JP4064194B2 (ja)	2008-03-19	凝集剤及びその使用方法
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JP3294015B2 (ja)	2002-06-17	中性サイズ定着剤
JPH0598595A (ja)	1993-04-20	紙力増強剤
SU652192A1 (ru)	1979-03-15	Сополимер метакриламида, алкилированного и неалкилированного алкиламиноалкил(мет)акрилата и олигоэфиракрилата в качестве флоккулирующего агента дл бумажной массы