CA1175830A - Process for preparing n-substituted acrylamides and methacrylamides - Google Patents
Process for preparing n-substituted acrylamides and methacrylamidesInfo
- Publication number
- CA1175830A CA1175830A CA000407528A CA407528A CA1175830A CA 1175830 A CA1175830 A CA 1175830A CA 000407528 A CA000407528 A CA 000407528A CA 407528 A CA407528 A CA 407528A CA 1175830 A CA1175830 A CA 1175830A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- group
- amine
- acrylamide
- decomposition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000003926 acrylamides Chemical class 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 40
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 30
- -1 N-substituted acrylamides Chemical class 0.000 claims abstract description 18
- 238000004821 distillation Methods 0.000 claims abstract description 12
- 239000000376 reactant Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 238000000354 decomposition reaction Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical class NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- HQMLIDZJXVVKCW-UHFFFAOYSA-N 2-aminopropanamide Chemical class CC(N)C(N)=O HQMLIDZJXVVKCW-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000000197 pyrolysis Methods 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007056 transamidation reaction Methods 0.000 description 5
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- MCSVQCDNSCMOAS-UHFFFAOYSA-N 1-n',1-n',2,2-tetramethylpropane-1,1-diamine Chemical compound CN(C)C(N)C(C)(C)C MCSVQCDNSCMOAS-UHFFFAOYSA-N 0.000 description 3
- OOFAEFCMEHZNGP-UHFFFAOYSA-N 1-n',1-n'-dimethylpropane-1,1-diamine Chemical compound CCC(N)N(C)C OOFAEFCMEHZNGP-UHFFFAOYSA-N 0.000 description 3
- ANCPBLUIOKGULL-UHFFFAOYSA-N 2-methylidene-3-oxopent-4-enamide Chemical group NC(=O)C(=C)C(=O)C=C ANCPBLUIOKGULL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 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 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 101100379067 Caenorhabditis elegans anc-1 gene Proteins 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3128574A DE3128574C2 (de) | 1981-07-20 | 1981-07-20 | Verfahren zur Herstellung von N-substituierten Acryl- und Methacrylamiden |
| DEP3128574.0 | 1981-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1175830A true CA1175830A (en) | 1984-10-09 |
Family
ID=6137298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000407528A Expired CA1175830A (en) | 1981-07-20 | 1982-07-19 | Process for preparing n-substituted acrylamides and methacrylamides |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0070425B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5818346A (enrdf_load_stackoverflow) |
| CA (1) | CA1175830A (enrdf_load_stackoverflow) |
| DE (2) | DE3128574C2 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920222A (en) * | 1988-02-19 | 1990-04-24 | Shell Internationale Research Maatschappij B.V. | Preparation of 3,3-diarylacrylic acid amides |
| CN103772226A (zh) * | 2009-05-01 | 2014-05-07 | 出光兴产株式会社 | α β不饱和羧酸-N,N二取代酰胺以及3-烷氧基羧酸-N,N二取代酰胺的制造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3402599C2 (de) * | 1984-01-26 | 1986-02-27 | Chemische Fabrik Stockhausen GmbH, 4150 Krefeld | Verfahren zur Herstellung von N-substituierten α,ß-ungesättigten Carbonsäureamiden |
| US5587515A (en) * | 1992-10-21 | 1996-12-24 | Kohjin Co., Ltd. | Method of manufacturing N-monosubstituted (meth)acrylamides |
| JP2000273072A (ja) * | 1999-03-24 | 2000-10-03 | Kohjin Co Ltd | （メタ）アクリルアミド誘導体の製法 |
| DE10119685A1 (de) | 2001-04-20 | 2002-10-24 | Stockhausen Chem Fab Gmbh | Entfernung nicht-wasserlöslicher Substanzen aus Metallaufschlüssen |
| DE102009060535A1 (de) | 2009-12-23 | 2011-06-30 | Ashland Licensing and Intellectual Property LLC, Ohio | Katlonisches Polymer basierend auf Dimethylaminopropylacrylamid-Hydrosulfat zur Sedimentation von in Schwefelsäure unlöslichen Materialien bei der Herstellung von Titandioxid |
| WO2021010268A1 (ja) | 2019-07-16 | 2021-01-21 | 三菱ケミカル株式会社 | Ｎ－置換アミド化合物／アミド化合物共重合体の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143220A (en) * | 1972-05-13 | 1979-03-06 | Bayer Aktiengesellschaft | Polyurethanes prepared with novel mannich bases |
| US3878247A (en) * | 1974-01-25 | 1975-04-15 | Jefferson Chem Co Inc | Preparation of n-(tertiaryaminoalkyl) acrylamides |
| IN151693B (enrdf_load_stackoverflow) * | 1978-05-05 | 1983-07-02 | Stockhausen & Cie Chem Fab | |
| DE2856383C2 (de) * | 1978-12-27 | 1982-11-25 | Chemische Fabrik Stockhausen GmbH, 4150 Krefeld | 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 |
| DE2918486C2 (de) * | 1979-05-08 | 1982-10-14 | Chemische Fabrik Stockhausen GmbH, 4150 Krefeld | Verfahren zur Herstellung von N-substituierten Acrylamiden |
-
1981
- 1981-07-20 DE DE3128574A patent/DE3128574C2/de not_active Expired
-
1982
- 1982-06-29 DE DE8282105752T patent/DE3262545D1/de not_active Expired
- 1982-06-29 EP EP82105752A patent/EP0070425B1/de not_active Expired
- 1982-07-15 JP JP57122273A patent/JPS5818346A/ja active Granted
- 1982-07-19 CA CA000407528A patent/CA1175830A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920222A (en) * | 1988-02-19 | 1990-04-24 | Shell Internationale Research Maatschappij B.V. | Preparation of 3,3-diarylacrylic acid amides |
| CN103772226A (zh) * | 2009-05-01 | 2014-05-07 | 出光兴产株式会社 | α β不饱和羧酸-N,N二取代酰胺以及3-烷氧基羧酸-N,N二取代酰胺的制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5818346A (ja) | 1983-02-02 |
| EP0070425B1 (de) | 1985-03-13 |
| DE3128574A1 (de) | 1983-01-27 |
| DE3128574C2 (de) | 1984-03-29 |
| JPH0343262B2 (enrdf_load_stackoverflow) | 1991-07-01 |
| EP0070425A1 (de) | 1983-01-26 |
| DE3262545D1 (en) | 1985-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4206143A (en) | Method for making N-substituted acrylamides and methacrylamides | |
| CA1175830A (en) | Process for preparing n-substituted acrylamides and methacrylamides | |
| US4675442A (en) | Method of making methacrylamides | |
| JPH0237913B2 (enrdf_load_stackoverflow) | ||
| US4321411A (en) | Process for producing N-substituted acrylamide or methacrylamide | |
| JPH07145122A (ja) | Ｎ−アルキル−α，β−不飽和カルボン酸アミドの製造方法 | |
| EP0619295B1 (en) | Process for producing n-monosubstituted (meth)acrylamyde | |
| US3078275A (en) | N, n-disubstituted-alpha-(tertiaryaminoalkyl)-alpha, alpha-diphenylacetamides | |
| WO2000002855A2 (en) | Synthesis of compounds useful in the manufacture of ketorolac | |
| US5089653A (en) | Process for the selective reduction of the 4-halogen in 2,4-dihaloanilines | |
| JP3274258B2 (ja) | Ｎ−モノ置換−（メタ）アクリルアミドの製法 | |
| JPS5826849A (ja) | メタクリル−及びアクリルアミドの製造法 | |
| US5072024A (en) | Synthesis of N-substituted amides by condensation of nitriles with certain organic hydroxyl compounds | |
| JPH0434982B2 (enrdf_load_stackoverflow) | ||
| GB2103216A (en) | Process for the preparation of N-substituted methacrylamides and acrylamides | |
| US5792880A (en) | Process for the preparation of N-lauroyl-L-glutamic acid di-n-butylamide | |
| EP0413140B1 (en) | Process for production of carboxylic acid esters and formamide | |
| US3686262A (en) | Preparation of (2-cyanoethyl) ketones | |
| US4933462A (en) | Synthesis of 3-(2-hydroxyethyl)-2-oxazolidinones | |
| US4062893A (en) | Process for preparing N,N-dialkyl aromatic amines | |
| JP3242213B2 (ja) | Ｎ−（メタ）アクリロイルモルホリンの製造方法 | |
| US5099066A (en) | Synthesis of N-substituted amides by condensation of nitriles with certain organic hydroxyl compounds | |
| US5026866A (en) | Synthesis of 2,2'-bis-Δ2 -oxazoline | |
| KR810002038B1 (ko) | 할로 아실아미드의 제조방법 | |
| US5066813A (en) | Method for production of 1,3-thiazolidin-2-ones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |