DE3123970C2 - - Google Patents
Info
- Publication number
- DE3123970C2 DE3123970C2 DE3123970A DE3123970A DE3123970C2 DE 3123970 C2 DE3123970 C2 DE 3123970C2 DE 3123970 A DE3123970 A DE 3123970A DE 3123970 A DE3123970 A DE 3123970A DE 3123970 C2 DE3123970 C2 DE 3123970C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- ester
- compounds
- amine
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001412 amines Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000010936 titanium Substances 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 description 25
- -1 N-substituted amides Chemical class 0.000 description 18
- 238000009835 boiling Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 238000006845 Michael addition reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007098 aminolysis reaction Methods 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- HRHKBQXBOFVHMK-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-1,1-dimethylhydrazine Chemical compound CN(C)NCC(C)(C)C HRHKBQXBOFVHMK-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- IJSVVICYGLOZHA-UHFFFAOYSA-N 2-methyl-n-phenylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=CC=C1 IJSVVICYGLOZHA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 244000309494 Bipolaris glycines Species 0.000 description 1
- 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 1
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- GYIPQKRAWKCWHP-UHFFFAOYSA-N [V+5].[O-2].[Al+3].[O-2].[O-2].[O-2] Chemical class [V+5].[O-2].[Al+3].[O-2].[O-2].[O-2] GYIPQKRAWKCWHP-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical class NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002510 isobutyric acid esters Chemical class 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 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
- CEBFLGHPYLIZSC-UHFFFAOYSA-N n-benzyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCC1=CC=CC=C1 CEBFLGHPYLIZSC-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000007039 two-step reaction Methods 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
- 239000008096 xylene Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813123970 DE3123970A1 (de) | 1981-06-19 | 1981-06-19 | "verfahren zur herstellung von methacrylamiden" |
| FR8208642A FR2508034B1 (fr) | 1981-06-19 | 1982-05-18 | Procede de preparation d'amides acryliques et methacryliques |
| IT67707/82A IT1156355B (it) | 1981-06-19 | 1982-06-01 | Procedimento per la produzione di ammidi di acido acrilico o metacrilico |
| GB08217664A GB2100732B (en) | 1981-06-19 | 1982-06-18 | Process for acrylamide or methacrylamide preparation |
| JP57105256A JPS58949A (ja) | 1981-06-19 | 1982-06-18 | アクリル−および／またはメタクリル酸のアミドの製造法 |
| US06/709,343 US4675442A (en) | 1981-06-19 | 1985-03-06 | Method of making methacrylamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813123970 DE3123970A1 (de) | 1981-06-19 | 1981-06-19 | "verfahren zur herstellung von methacrylamiden" |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3123970A1 DE3123970A1 (de) | 1983-01-05 |
| DE3123970C2 true DE3123970C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-07-05 |
Family
ID=6134846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813123970 Granted DE3123970A1 (de) | 1981-06-19 | 1981-06-19 | "verfahren zur herstellung von methacrylamiden" |
Country Status (6)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4492801A (en) * | 1983-02-28 | 1985-01-08 | Texaco Inc. | Production of N-substituted (meth)acrylamides from (meth)acrylates and amines over a metal alkoxide catalyst |
| EP0216966B2 (en) * | 1985-09-04 | 1996-03-06 | Huntsman Corporation | Improved process for the production of N-substituted (meth) acrylamides from (meth) acrylates & amines over a metal oxide or alkoxide catalyst |
| JPS60141360A (ja) * | 1983-12-28 | 1985-07-26 | Kyocera Corp | 鋳造装置 |
| JPS62281848A (ja) * | 1986-04-01 | 1987-12-07 | Japan Tobacco Inc | 酸アミドの合成法 |
| EP0401286B1 (en) * | 1988-02-25 | 1995-09-13 | The Dow Chemical Company | Process for preparing n-(hydroxyalkyl)-2-unsaturated amides and 2-alkenyl oxazolines |
| MX170841B (es) * | 1988-09-26 | 1993-09-20 | Goodyear Tire & Rubber | Proceso mejorado para la sintesis catalizada de metacrilaminadas y acrilimidas n-substituidas |
| US4959489A (en) * | 1989-10-02 | 1990-09-25 | Air Products And Chemicals, Inc. | Process for making an acrylamide containing a dialkyl acetal group |
| DE4027843A1 (de) * | 1990-09-03 | 1992-03-05 | Roehm Gmbh | Kontinuierliches verfahren zur herstellung von n-substituierten acryl- und methacrylamiden |
| EP0697398B1 (de) * | 1994-08-19 | 1997-10-29 | BASF Aktiengesellschaft | Verfahren zur Herstellung von N-Alkenylcarbonsäureamiden |
| US5679852A (en) * | 1995-06-02 | 1997-10-21 | Schering Aktiengesellschaft | Process for the production of DTPA-monoamides of the central carboxylic acid and their use as pharmaceutical agents |
| DE10323699A1 (de) * | 2003-05-22 | 2004-12-09 | Röhm GmbH & Co. KG | Verfahren zur kontinuierlichen Herstellung von Alkylamino(meth)acrylamiden |
| KR101246421B1 (ko) * | 2004-11-23 | 2013-03-21 | 에보니크 룀 게엠베하 | 알킬 아미노 아크릴 아미드의 연속 제조 방법 |
| DE102005017453A1 (de) * | 2005-04-15 | 2006-10-19 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Amiden basierend auf Polyetheraminen und (Meth)acrylsäure |
| DE102006036220A1 (de) | 2006-08-03 | 2008-02-07 | Clariant International Limited | Polyetheramin-Makromonomere mit zwei benachbarten Hydroxylgruppen und ihre Verwendung zur Herstellung von Polyurethanen |
| WO2008118312A1 (en) | 2007-03-23 | 2008-10-02 | Rhodia Inc. | Process for making a (meth) acrylamide monomer |
| JP5221107B2 (ja) | 2007-11-12 | 2013-06-26 | 花王株式会社 | 脂肪族カルボン酸アミドの製造方法 |
| US20210070690A1 (en) * | 2016-05-23 | 2021-03-11 | Chubu University Educational Foundation | Catalyst for converting ester to amide using hydroxyl group as orientation group |
| CN108047075A (zh) * | 2017-12-20 | 2018-05-18 | 蓬莱星火化工有限公司 | (甲基)丙烯酰胺丙基二甲基胺的合成方法 |
| JPWO2022249994A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 2021-05-28 | 2022-12-01 | ||
| CN117242052A (zh) * | 2021-05-28 | 2023-12-15 | 富士胶片株式会社 | N-（杂）芳基（甲基）丙烯酰胺化合物的制造方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529838A (en) * | 1948-09-23 | 1950-11-14 | American Cyanamid Co | Preparation of n, n-dialkylacrylamides |
| US2719175A (en) * | 1952-11-01 | 1955-09-27 | Eastman Kodak Co | Vapor phase preparation of n-substituted acrylamides |
| DE2110060C3 (de) * | 1971-03-03 | 1980-06-26 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von Nsubstituierten Carbonsäureamiden |
| SE395000B (sv) * | 1970-06-02 | 1977-07-25 | Henkel & Cie Gmbh | Forfarande for framstellning av karbonsyraamider genom omsettning av karbonsyror med ammoniak eller aminer |
| US3816483A (en) * | 1970-06-02 | 1974-06-11 | Henkel & Cie Gmbh | Carboxylic acid amide preparation |
| US3763234A (en) * | 1970-12-03 | 1973-10-02 | Halcon International Inc | Preparation of amides |
| GB1312386A (en) * | 1970-12-23 | 1973-04-04 | Hemscheidt Maschf Hermann | Hydraulic roof-support frame |
| GB1396615A (en) * | 1973-01-04 | 1975-06-04 | British Titan Ltd | Condensation process |
| US3878247A (en) * | 1974-01-25 | 1975-04-15 | Jefferson Chem Co Inc | Preparation of n-(tertiaryaminoalkyl) acrylamides |
| US3907893A (en) * | 1974-06-28 | 1975-09-23 | Goodyear Tire & Rubber | Preparation of antioxidant amides |
| US3945970A (en) * | 1974-06-28 | 1976-03-23 | The Goodyear Tire & Rubber Company | Preparation of methacrylamides |
| US4322551A (en) * | 1978-02-16 | 1982-03-30 | The Goodyear Tire & Rubber Company | Process for preparing aromatic amide antioxidants |
| DE2809102C2 (de) * | 1978-03-03 | 1986-12-04 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung von α,β-ungesättigen Carbonsäureamiden |
| DE3048020A1 (de) * | 1978-04-17 | 1982-07-15 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung n-substituierter acryl- oder methacrylamide |
| DE2816516C2 (de) * | 1978-04-17 | 1985-05-15 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung N-substituierter Acryl- und Methacrylamide |
| JPS5829287B2 (ja) * | 1980-03-12 | 1983-06-22 | 日東化学工業株式会社 | Ｎ−置換アクリルアミドまたはｎ−置換メタクリルアミドの製造方法 |
| US4549017A (en) * | 1983-09-23 | 1985-10-22 | Texaco Inc. | Process for the production of N-substituted (meth)acrylamides from (meth)acrylates and amines over a metal oxide or alkoxide catalyst |
-
1981
- 1981-06-19 DE DE19813123970 patent/DE3123970A1/de active Granted
-
1982
- 1982-05-18 FR FR8208642A patent/FR2508034B1/fr not_active Expired
- 1982-06-01 IT IT67707/82A patent/IT1156355B/it active
- 1982-06-18 JP JP57105256A patent/JPS58949A/ja active Granted
- 1982-06-18 GB GB08217664A patent/GB2100732B/en not_active Expired
-
1985
- 1985-03-06 US US06/709,343 patent/US4675442A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4675442A (en) | 1987-06-23 |
| GB2100732A (en) | 1983-01-06 |
| JPH0261937B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-21 |
| DE3123970A1 (de) | 1983-01-05 |
| GB2100732B (en) | 1985-08-07 |
| IT8267707A0 (it) | 1982-06-01 |
| IT1156355B (it) | 1987-02-04 |
| FR2508034B1 (fr) | 1986-03-21 |
| FR2508034A1 (fr) | 1982-12-24 |
| JPS58949A (ja) | 1983-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ROEHM GMBH & CO. KG, 64293 DARMSTADT, DE |