DE102008054612A1 - Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid - Google Patents
Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid Download PDFInfo
- Publication number
- DE102008054612A1 DE102008054612A1 DE102008054612A DE102008054612A DE102008054612A1 DE 102008054612 A1 DE102008054612 A1 DE 102008054612A1 DE 102008054612 A DE102008054612 A DE 102008054612A DE 102008054612 A DE102008054612 A DE 102008054612A DE 102008054612 A1 DE102008054612 A1 DE 102008054612A1
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated carboxylic
- preparation
- anhydride
- amides
- carboxylic acids
- 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.)
- Withdrawn
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title abstract description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title abstract description 6
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 claims description 2
- -1 carbenium ions Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(C/C=C/CCCC1)C(*N)(CC(*)CC1)CC1O Chemical compound CC1(C/C=C/CCCC1)C(*N)(CC(*)CC1)CC1O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000006434 Ritter amidation reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- HOZLHJIPBBRFGM-UHFFFAOYSA-N n-dodecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C(C)=C HOZLHJIPBBRFGM-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical group CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 1
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- UIOSCHPMOHHRNY-UHFFFAOYSA-N 1-n,4-n,4-n-triethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(N(CC)CC)C=C1 UIOSCHPMOHHRNY-UHFFFAOYSA-N 0.000 description 1
- AWXUBHMURFEJMY-UHFFFAOYSA-N 1-n,4-n,4-n-trimethylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N(C)C)C=C1 AWXUBHMURFEJMY-UHFFFAOYSA-N 0.000 description 1
- KDLIPGJLQQTGKY-UHFFFAOYSA-N 1-n,4-n-bis(2-methylpropyl)benzene-1,4-diamine Chemical compound CC(C)CNC1=CC=C(NCC(C)C)C=C1 KDLIPGJLQQTGKY-UHFFFAOYSA-N 0.000 description 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 description 1
- ZEMODTUZIWTRPF-UHFFFAOYSA-N 1-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(NCC)C=C1 ZEMODTUZIWTRPF-UHFFFAOYSA-N 0.000 description 1
- UQGWMGDVLKILAW-UHFFFAOYSA-N 1-n-(2-methylpropyl)-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NCC(C)C)=CC=C1NC1=CC=CC=C1 UQGWMGDVLKILAW-UHFFFAOYSA-N 0.000 description 1
- PIPXINMICYUFAD-UHFFFAOYSA-N 1-n-butyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NCCCC)=CC=C1NC1=CC=CC=C1 PIPXINMICYUFAD-UHFFFAOYSA-N 0.000 description 1
- JFVLZAWPGJYRAF-UHFFFAOYSA-N 1-n-ethyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NCC)=CC=C1NC1=CC=CC=C1 JFVLZAWPGJYRAF-UHFFFAOYSA-N 0.000 description 1
- LISMVBJUACINFW-UHFFFAOYSA-N 1-n-hexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NCCCCCC)=CC=C1NC1=CC=CC=C1 LISMVBJUACINFW-UHFFFAOYSA-N 0.000 description 1
- GYXXGCCWYRAYGT-UHFFFAOYSA-N 1-n-methyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NC1=CC=CC=C1 GYXXGCCWYRAYGT-UHFFFAOYSA-N 0.000 description 1
- FXAPKODDEVWFHP-UHFFFAOYSA-N 1-n-pentyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NCCCCC)=CC=C1NC1=CC=CC=C1 FXAPKODDEVWFHP-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- XSAFJJOOOGGPDU-UHFFFAOYSA-N 2-methylprop-2-enoate;propan-2-ylazanium Chemical compound CC(C)[NH3+].CC(=C)C([O-])=O XSAFJJOOOGGPDU-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- UXECZRHYNNQUEH-UHFFFAOYSA-N 4-n,4-n-di(butan-2-yl)-1-n-phenylbenzene-1,4-diamine;4-n,4-n-dibutyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N(CCCC)CCCC)=CC=C1NC1=CC=CC=C1.C1=CC(N(C(C)CC)C(C)CC)=CC=C1NC1=CC=CC=C1 UXECZRHYNNQUEH-UHFFFAOYSA-N 0.000 description 1
- GYBOHKQUSAITPM-UHFFFAOYSA-N 4-n,4-n-diethyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=CC=CC=C1 GYBOHKQUSAITPM-UHFFFAOYSA-N 0.000 description 1
- QETJPYXHTISDOG-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=CC=C1 QETJPYXHTISDOG-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- UHJVLUYSDYOULM-UHFFFAOYSA-N 4-n-(5-methylhexan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCC(C)C)=CC=C1NC1=CC=CC=C1 UHJVLUYSDYOULM-UHFFFAOYSA-N 0.000 description 1
- LIAVGCGPNJLGQT-UHFFFAOYSA-N 4-n-butan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC)=CC=C1NC1=CC=CC=C1 LIAVGCGPNJLGQT-UHFFFAOYSA-N 0.000 description 1
- UUHDOYXTPSCMOY-UHFFFAOYSA-N 4-n-ethyl-4-n-methyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N(C)CC)=CC=C1NC1=CC=CC=C1 UUHDOYXTPSCMOY-UHFFFAOYSA-N 0.000 description 1
- BESSXHKSLAMFFX-UHFFFAOYSA-N 4-n-heptan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCCCC)=CC=C1NC1=CC=CC=C1 BESSXHKSLAMFFX-UHFFFAOYSA-N 0.000 description 1
- PILIQRYPQJIREQ-UHFFFAOYSA-N 4-n-phenyl-1-n-propylbenzene-1,4-diamine Chemical compound C1=CC(NCCC)=CC=C1NC1=CC=CC=C1 PILIQRYPQJIREQ-UHFFFAOYSA-N 0.000 description 1
- BQCPAKBDPLFSFR-UHFFFAOYSA-N 4-n-tert-butyl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)(C)C)=CC=C1NC1=CC=CC=C1 BQCPAKBDPLFSFR-UHFFFAOYSA-N 0.000 description 1
- XOIZPYZCDNKYBW-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-diol Chemical compound CC(C)(C)C1=CC(O)=CC(O)=C1 XOIZPYZCDNKYBW-UHFFFAOYSA-N 0.000 description 1
- ZMWAXVAETNTVAT-UHFFFAOYSA-N 7-n,8-n,5-triphenylphenazin-5-ium-2,3,7,8-tetramine;chloride Chemical compound [Cl-].C=1C=CC=CC=1NC=1C=C2[N+](C=3C=CC=CC=3)=C3C=C(N)C(N)=CC3=NC2=CC=1NC1=CC=CC=C1 ZMWAXVAETNTVAT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- IPPWILKGXFOXHO-UHFFFAOYSA-N chloranilic acid Chemical compound OC1=C(Cl)C(=O)C(O)=C(Cl)C1=O IPPWILKGXFOXHO-UHFFFAOYSA-N 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008054612A DE102008054612A1 (de) | 2008-12-15 | 2008-12-15 | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
| RU2011129251/04A RU2011129251A (ru) | 2008-12-15 | 2009-11-19 | Способ получения n-изопропил (мет) акриламида |
| RU2015101155/04A RU2015101155A (ru) | 2008-12-15 | 2009-11-19 | Способ получения n-изопропил(мет)акриламида |
| EP09756729.1A EP2358664B1 (de) | 2008-12-15 | 2009-11-19 | Verfahren zur herstellung von n-isopropyl(meth)acrylamid |
| KR1020117010969A KR20110099683A (ko) | 2008-12-15 | 2009-11-19 | Ｎ―이소프로필(메트)아크릴아미드의 제조 방법 |
| EP20156880.5A EP3680231A1 (de) | 2008-12-15 | 2009-11-19 | Verfahren zur herstellung von n-isopropyl(meth)acrylamid |
| PCT/EP2009/065435 WO2010072480A1 (de) | 2008-12-15 | 2009-11-19 | Verfahren zur herstellung von n-isopropyl(meth)acrylamid |
| US13/119,244 US9512062B2 (en) | 2008-12-15 | 2009-11-19 | Method for producing N-isopropyl(meth)acrylamide |
| JP2011541268A JP5791511B2 (ja) | 2008-12-15 | 2009-11-19 | Ｎ−イソプロピル（メタ）アクリルアミドの製造方法 |
| ES09756729T ES2790593T3 (es) | 2008-12-15 | 2009-11-19 | Procedimiento para preparación de N-isopropil(met)acrilamida |
| KR1020177007294A KR101853597B1 (ko) | 2008-12-15 | 2009-11-19 | Ｎ―이소프로필(메트)아크릴아미드의 제조 방법 |
| CN2009801421344A CN102197018A (zh) | 2008-12-15 | 2009-11-19 | 制备n-异丙基(甲基)丙烯酰胺的方法 |
| CN201710008630.7A CN106631862A (zh) | 2008-12-15 | 2009-11-19 | 制备n‑异丙基(甲基)丙烯酰胺的方法 |
| TW098142285A TWI498314B (zh) | 2008-12-15 | 2009-12-10 | Ｎ－異丙基（甲基）丙烯醯胺的製備方法 |
| JP2015038420A JP2015134794A (ja) | 2008-12-15 | 2015-02-27 | Ｎ−イソプロピル（メタ）アクリルアミドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008054612A DE102008054612A1 (de) | 2008-12-15 | 2008-12-15 | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102008054612A1 true DE102008054612A1 (de) | 2010-06-17 |
Family
ID=42125499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102008054612A Withdrawn DE102008054612A1 (de) | 2008-12-15 | 2008-12-15 | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9512062B2 (https=) |
| EP (2) | EP3680231A1 (https=) |
| JP (2) | JP5791511B2 (https=) |
| KR (2) | KR101853597B1 (https=) |
| CN (2) | CN106631862A (https=) |
| DE (1) | DE102008054612A1 (https=) |
| ES (1) | ES2790593T3 (https=) |
| RU (2) | RU2011129251A (https=) |
| TW (1) | TWI498314B (https=) |
| WO (1) | WO2010072480A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3599232A1 (de) * | 2018-07-26 | 2020-01-29 | Evonik Operations GmbH | Verfahren zur herstellung von n-methyl(meth)acrylamid |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011089363A1 (de) * | 2011-12-21 | 2013-06-27 | Evonik Röhm Gmbh | Verfahren zur Herstellung von N-Alkyl(meth)acrylamiden |
| US11136287B2 (en) | 2017-03-01 | 2021-10-05 | Api Corporation | Method for producing n-benzyl-2-bromo-3-methoxypropionamide and intermediates thereof |
| CN107200695A (zh) * | 2017-06-13 | 2017-09-26 | 山东瑞博龙化工科技股份有限公司 | 一种制备n‑羟乙基甲基丙烯酰胺的方法 |
| CN107245039A (zh) * | 2017-06-13 | 2017-10-13 | 山东瑞博龙化工科技股份有限公司 | 一种制备n‑羟乙基丙烯酰胺的方法 |
| US11505520B2 (en) | 2018-05-23 | 2022-11-22 | Evonik Operations Gmbh | Method for preparing keto-functionalized aromatic (meth)acrylates |
| EP3652151B1 (en) | 2018-07-17 | 2020-08-12 | Evonik Operations GmbH | Method for preparing c-h acidic (meth)acrylates |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD76235A5 (de) * | 1968-02-05 | 1970-09-20 | Sumitomo Chemical Co | Verfahren zur Herstellung von Bis-amiden |
| GB2102426A (en) * | 1981-08-01 | 1983-02-02 | Roehm Gmbh | Process for the preparation of methacrylamide or acrylamide |
| DE3131096A1 (de) | 1981-08-06 | 1983-02-24 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von n-substituierten methacryl- und acrylamiden |
| DE3412650A1 (de) * | 1984-04-04 | 1985-10-17 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von hydroxyalkyl-acrylamiden und -methacrylamiden |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH580572A5 (https=) | 1973-10-03 | 1976-10-15 | Lonza Ag | |
| US4288592A (en) * | 1979-04-30 | 1981-09-08 | American Cyanamid Company | Process for preparing amides by reaction in presence of molecular sieve |
| FR2590567B1 (fr) * | 1985-11-27 | 1988-07-15 | Charbonnages Ste Chimique | Nouveau procede de synthese de (meth)acrylamide de n-dialkylaminoalkyle |
| JPH03264549A (ja) | 1990-03-15 | 1991-11-25 | Sanyo Chem Ind Ltd | 不飽和単量体の製造方法 |
| RU2137740C1 (ru) | 1995-06-08 | 1999-09-20 | Эксон продакшн рисерч компани | Способ ингибирования образования клатрат-гидратов в жидкости |
| DE10010811A1 (de) * | 2000-03-08 | 2001-09-13 | Basf Ag | Verfahren zur Herstellung von Polymeren |
| US6753431B2 (en) * | 2000-06-02 | 2004-06-22 | Sumitomo Chemical Company Limited | Production of mixed acid anhydride and amide compound |
| US20040024152A1 (en) * | 2000-07-28 | 2004-02-05 | Masayuki Toyama | Gas hydrate formation inhibitor and method for inhibiting gas hydrate formation with the same |
| WO2005121133A1 (en) * | 2004-06-11 | 2005-12-22 | Takeda Pharmaceutical Company Limited | Highly selective novel amidation method |
| DE102006047617B4 (de) | 2006-10-09 | 2008-11-27 | Clariant International Limited | Verfahren zur Herstellung basischer (Meth)acrylamide |
| US8445723B2 (en) | 2008-08-19 | 2013-05-21 | Nalco Company | Processes for producing N-alkyl (alkyl)acrylamides |
-
2008
- 2008-12-15 DE DE102008054612A patent/DE102008054612A1/de not_active Withdrawn
-
2009
- 2009-11-19 RU RU2011129251/04A patent/RU2011129251A/ru unknown
- 2009-11-19 RU RU2015101155/04A patent/RU2015101155A/ru not_active Application Discontinuation
- 2009-11-19 EP EP20156880.5A patent/EP3680231A1/de not_active Withdrawn
- 2009-11-19 WO PCT/EP2009/065435 patent/WO2010072480A1/de not_active Ceased
- 2009-11-19 JP JP2011541268A patent/JP5791511B2/ja active Active
- 2009-11-19 CN CN201710008630.7A patent/CN106631862A/zh active Pending
- 2009-11-19 KR KR1020177007294A patent/KR101853597B1/ko active Active
- 2009-11-19 KR KR1020117010969A patent/KR20110099683A/ko not_active Ceased
- 2009-11-19 CN CN2009801421344A patent/CN102197018A/zh active Pending
- 2009-11-19 US US13/119,244 patent/US9512062B2/en active Active
- 2009-11-19 ES ES09756729T patent/ES2790593T3/es active Active
- 2009-11-19 EP EP09756729.1A patent/EP2358664B1/de active Active
- 2009-12-10 TW TW098142285A patent/TWI498314B/zh active
-
2015
- 2015-02-27 JP JP2015038420A patent/JP2015134794A/ja not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD76235A5 (de) * | 1968-02-05 | 1970-09-20 | Sumitomo Chemical Co | Verfahren zur Herstellung von Bis-amiden |
| GB2102426A (en) * | 1981-08-01 | 1983-02-02 | Roehm Gmbh | Process for the preparation of methacrylamide or acrylamide |
| DE3131096A1 (de) | 1981-08-06 | 1983-02-24 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von n-substituierten methacryl- und acrylamiden |
| DE3412650A1 (de) * | 1984-04-04 | 1985-10-17 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von hydroxyalkyl-acrylamiden und -methacrylamiden |
Non-Patent Citations (1)
| Title |
|---|
| DS 25 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3599232A1 (de) * | 2018-07-26 | 2020-01-29 | Evonik Operations GmbH | Verfahren zur herstellung von n-methyl(meth)acrylamid |
| WO2020020698A1 (en) * | 2018-07-26 | 2020-01-30 | Evonik Operations Gmbh | Process for preparing n-methyl(meth)acrylamide |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2358664B1 (de) | 2020-03-25 |
| US20110218312A1 (en) | 2011-09-08 |
| JP5791511B2 (ja) | 2015-10-07 |
| TWI498314B (zh) | 2015-09-01 |
| CN106631862A (zh) | 2017-05-10 |
| EP3680231A1 (de) | 2020-07-15 |
| WO2010072480A1 (de) | 2010-07-01 |
| JP2012512217A (ja) | 2012-05-31 |
| RU2015101155A3 (https=) | 2018-08-31 |
| JP2015134794A (ja) | 2015-07-27 |
| TW201035015A (en) | 2010-10-01 |
| US9512062B2 (en) | 2016-12-06 |
| ES2790593T3 (es) | 2020-10-28 |
| CN102197018A (zh) | 2011-09-21 |
| EP2358664A1 (de) | 2011-08-24 |
| RU2015101155A (ru) | 2015-06-27 |
| KR101853597B1 (ko) | 2018-04-30 |
| RU2011129251A (ru) | 2013-01-20 |
| KR20110099683A (ko) | 2011-09-08 |
| KR20170033910A (ko) | 2017-03-27 |
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