CS223883B2 - Method of making the n-substituted amide alpha,beta-nonsaturated carboxyl acids - Google Patents

Method of making the n-substituted amide alpha,beta-nonsaturated carboxyl acids Download PDF

Info

Publication number: CS223883B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; substituted; amides; alkyl; acid
Prior art date: 1978-12-27

Application number

CS923279A

Other languages

Czech (cs)

English (en)

Inventor

Erich Kuester

Bernhard Goossens

Kurt Dahmen

Eduard Barthell

Original Assignee

Stockhausen & Cie Chem Fab

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

1979-12-22

Publication date

1983-11-25

1979-12-22 Application filed by Stockhausen & Cie Chem Fab filed Critical Stockhausen & Cie Chem Fab

1980-09-29 Priority to CS806569A priority Critical patent/CS223886B2/cs

1983-11-25 Publication of CS223883B2 publication Critical patent/CS223883B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001412 amines Chemical class 0.000 claims abstract description 31
150000001408 amides Chemical class 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
230000018044 dehydration Effects 0.000 claims abstract description 10
238000006297 dehydration reaction Methods 0.000 claims abstract description 10
238000003379 elimination reaction Methods 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 4
230000008030 elimination Effects 0.000 claims abstract description 4
-1 N-substituted amides Chemical class 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000001735 carboxylic acids Chemical class 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
239000011949 solid catalyst Substances 0.000 claims description 8
238000003776 cleavage reaction Methods 0.000 claims description 7
230000007017 scission Effects 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000003141 primary amines Chemical class 0.000 claims description 4
239000000377 silicon dioxide Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
229910044991 metal oxide Inorganic materials 0.000 claims description 3
150000004706 metal oxides Chemical class 0.000 claims description 3
239000008262 pumice Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000003158 alcohol group Chemical group 0.000 claims description 2
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 claims description 2
229910000149 boron phosphate Inorganic materials 0.000 claims description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
101500006448 Mycobacterium bovis (strain ATCC BAA-935 / AF2122/97) Endonuclease PI-MboI Proteins 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
229910052809 inorganic oxide Inorganic materials 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 2
229920000728 polyester Polymers 0.000 abstract description 2
125000002947 alkylene group Chemical group 0.000 abstract 1
230000009435 amidation Effects 0.000 abstract 1
238000007112 amidation reaction Methods 0.000 abstract 1
238000009835 boiling Methods 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 14
239000000047 product Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
BPXCLLWXDHBFRH-UHFFFAOYSA-N 3-methoxypropanamide Chemical class COCCC(N)=O BPXCLLWXDHBFRH-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000000197 pyrolysis Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
VFPWOMLXNMBLCA-UHFFFAOYSA-N 3-methoxybutanamide Chemical compound COC(C)CC(N)=O VFPWOMLXNMBLCA-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 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
229920001577 copolymer Polymers 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000178 monomer Substances 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
239000002243 precursor Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
BRACMCXUUMEMOZ-UHFFFAOYSA-N 2-ethyl-n',n',2-trimethylpropane-1,3-diamine Chemical compound CCC(C)(CN)CN(C)C BRACMCXUUMEMOZ-UHFFFAOYSA-N 0.000 description 1
JQDXZJYAUSVHDH-UHFFFAOYSA-N 3-chloropropanamide Chemical class NC(=O)CCCl JQDXZJYAUSVHDH-UHFFFAOYSA-N 0.000 description 1
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
CTHLIEMDQZLSDA-UHFFFAOYSA-N 5-(dimethylamino)-4,4-dimethyl-2-methylidenepentanamide Chemical compound CN(C)CC(C)(C)CC(=C)C(N)=O CTHLIEMDQZLSDA-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
VMEPWIOVHIRLGQ-UHFFFAOYSA-N CCN(CC)CC(C)(C)CCCN Chemical compound CCN(CC)CC(C)(C)CCCN VMEPWIOVHIRLGQ-UHFFFAOYSA-N 0.000 description 1
IELGUDZLNXJFBS-UHFFFAOYSA-N CN(C1CC(CCC1)NC(C=C)=O)C Chemical compound CN(C1CC(CCC1)NC(C=C)=O)C IELGUDZLNXJFBS-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
IRLLIJUGYFWTPR-UHFFFAOYSA-N N,N,2,2-tetramethylbutane-1,4-diamine Chemical compound CN(C)CC(C)(C)CCN IRLLIJUGYFWTPR-UHFFFAOYSA-N 0.000 description 1
LZHGNHLJUDXSMN-UHFFFAOYSA-N N,N,2,2-tetramethylpentane-1,5-diamine Chemical compound CN(C)CC(C)(C)CCCN LZHGNHLJUDXSMN-UHFFFAOYSA-N 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
IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 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
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical class NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 1
ZSJHIZJESFFXAU-UHFFFAOYSA-N boric acid;phosphoric acid Chemical compound OB(O)O.OP(O)(O)=O ZSJHIZJESFFXAU-UHFFFAOYSA-N 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 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
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
239000003657 drainage water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
239000008394 flocculating agent Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
WIXVJXFSZZQRJP-UHFFFAOYSA-N n',n'-dibutyl-2,2-dimethylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CC(C)(C)CN WIXVJXFSZZQRJP-UHFFFAOYSA-N 0.000 description 1
VOPPDUQFENQNOL-UHFFFAOYSA-N n',n'-diethyl-2,2-dimethylpropane-1,3-diamine Chemical compound CCN(CC)CC(C)(C)CN VOPPDUQFENQNOL-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
QFVABCFXLYFZLN-UHFFFAOYSA-N n-[3-(dibutylamino)-2,2-dimethylpropyl]-2-methylprop-2-enamide Chemical compound CCCCN(CCCC)CC(C)(C)CNC(=O)C(C)=C QFVABCFXLYFZLN-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
LBRCNSTWERYGQU-UHFFFAOYSA-N n-[3-(dimethylamino)-2,2-dimethylpropyl]-3-methoxybutanamide Chemical compound COC(C)CC(=O)NCC(C)(C)CN(C)C LBRCNSTWERYGQU-UHFFFAOYSA-N 0.000 description 1
WORWKSGNLQMYSQ-UHFFFAOYSA-N n-[4-(dimethylamino)-3,3-dimethylbutyl]-2-methylprop-2-enamide Chemical compound CN(C)CC(C)(C)CCNC(=O)C(C)=C WORWKSGNLQMYSQ-UHFFFAOYSA-N 0.000 description 1
AZFUJRRXUZSZDK-UHFFFAOYSA-N n-[4-(dimethylamino)-3,3-dimethylbutyl]prop-2-enamide Chemical compound CN(C)CC(C)(C)CCNC(=O)C=C AZFUJRRXUZSZDK-UHFFFAOYSA-N 0.000 description 1
JIPOLJCPEDSWHY-UHFFFAOYSA-N n-[5-(dimethylamino)-4,4-dimethylpentyl]prop-2-enamide Chemical compound CN(C)CC(C)(C)CCCNC(=O)C=C JIPOLJCPEDSWHY-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-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
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000006561 solvent free reaction Methods 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000005156 substituted alkylene group Chemical group 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000008646 thermal stress Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
- C02F1/56—Macromolecular compounds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
- D21H17/45—Nitrogen-containing groups
- D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Hydrology & Water Resources (AREA)
Oil, Petroleum & Natural Gas (AREA)
Environmental & Geological Engineering (AREA)
Water Supply & Treatment (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Lubricants (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Paper (AREA)
Separation Of Suspended Particles By Flocculating Agents (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS923279A 1978-12-27 1979-12-22 Method of making the n-substituted amide alpha,beta-nonsaturated carboxyl acids CS223883B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS806569A CS223886B2 (cs)	1978-12-27	1980-09-29	Způsob výroby homopolymerů a kopolymerů N-substituovaných amidů a,fi-nenasycených karboxylových kyselin

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CS223883B2 true CS223883B2 (en)	1983-11-25

Family

ID=6058517

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS923279A CS223883B2 (en)	1978-12-27	1979-12-22	Method of making the n-substituted amide alpha,beta-nonsaturated carboxyl acids

Country Status (5)

Country	Link
JP (1)	JPS55115857A (ja)
CS (1)	CS223883B2 (ja)
DE (1)	DE2856383C2 (ja)
IN (1)	IN153678B (ja)
PL (1)	PL237981A1 (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2911642C2 (de) *	1979-03-24	1983-01-20	Chemische Fabrik Stockhausen GmbH, 4150 Krefeld	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
DE3128574C2 (de) *	1981-07-20	1984-03-29	Deutsche Texaco Ag, 2000 Hamburg	Verfahren zur Herstellung von N-substituierten Acryl- und Methacrylamiden
DE3209800C2 (de) *	1982-03-18	1990-03-08	Chemische Fabrik Stockhausen GmbH, 4150 Krefeld	Verfahren zur Herstellung von N-(tert. Aminoalkyl)acrylamiden
DE3800199A1 (de) *	1988-01-07	1989-07-20	Sandoz Ag	Seitenkettenhaltige vinylpolymere

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2534585A (en) *	1948-04-15	1950-12-19	American Cyanamid Co	Method of producing n-alkyl acrylamides
US3670048A (en) *	1966-09-09	1972-06-13	Du Pont	Graft copolymers of unsaturated polyethers on polyamide and polyester substrates
DE2819735C2 (de) *	1978-05-05	1982-09-16	Chemische Fabrik Stockhausen GmbH, 4150 Krefeld	Verfahren zur Herstellung von α,β-ungesättigten N-substituierten Säureamiden

1978
- 1978-12-27 DE DE19782856383 patent/DE2856383C2/de not_active Expired
1979
- 1979-12-22 CS CS923279A patent/CS223883B2/cs unknown
- 1979-12-24 PL PL23798179A patent/PL237981A1/xx unknown
- 1979-12-27 JP JP17398979A patent/JPS55115857A/ja active Granted
1980
- 1980-01-23 IN IN45/DEL/80A patent/IN153678B/en unknown

Also Published As

Publication number	Publication date
JPS6360732B2 (ja)	1988-11-25
JPS55115857A (en)	1980-09-06
PL237981A1 (en)	1983-04-11
DE2856383C2 (de)	1982-11-25
DE2856383A1 (de)	1980-07-03
IN153678B (ja)	1984-08-04

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US2355837A (en)	1944-08-15	Substituted glyoxalidines
US4680360A (en)	1987-07-14	Process for producing poly(allylamine) derivatives
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US4321411A (en)	1982-03-23	Process for producing N-substituted acrylamide or methacrylamide
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US6008371A (en)	1999-12-28	Process for the preparation of (meth)acrylic acid esters
US4166828A (en)	1979-09-04	Preparation of N-(aminomethyl)-α,β-ethylenically unsaturated carboxamides and their polymers
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US4256666A (en)	1981-03-17	Preparation of β-aminopropionamides
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JPH029851A (ja)	1990-01-12	第２ホルムアミドの合成方法
US4182844A (en)	1980-01-08	Preparation of polyaminoamide resin in the absence of water
US4288390A (en)	1981-09-08	Preparation of N-(aminomethyl)-α,β-ethylenically unsaturated carboxamides and their polymers
JP2878211B2 (ja)	1999-04-05	アルキルイミダゾリドン（メタ）アクリレートの製造方法