DE1468939A1 - Verfahren zur Herstellung von Methacrylsaeuremethylester - Google Patents
Verfahren zur Herstellung von MethacrylsaeuremethylesterInfo
- Publication number
- DE1468939A1 DE1468939A1 DE19651468939 DE1468939A DE1468939A1 DE 1468939 A1 DE1468939 A1 DE 1468939A1 DE 19651468939 DE19651468939 DE 19651468939 DE 1468939 A DE1468939 A DE 1468939A DE 1468939 A1 DE1468939 A1 DE 1468939A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- water
- methacrylic acid
- reaction
- methyl methacrylate
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 44
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- NTQWADDNQQUGRH-UHFFFAOYSA-N hydrogen sulfate;2-methylprop-2-enoylazanium Chemical compound OS(O)(=O)=O.CC(=C)C(N)=O NTQWADDNQQUGRH-UHFFFAOYSA-N 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 14
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 description 19
- 238000005886 esterification reaction Methods 0.000 description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 238000001256 steam distillation Methods 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000006140 methanolysis reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GSGDLMJZJATUFX-UHFFFAOYSA-N S(O)(O)(=O)=O.S(=O)(=O)(O)O.C(C(=C)C)(=O)N Chemical compound S(O)(O)(=O)=O.S(=O)(=O)(O)O.C(C(=C)C)(=O)N GSGDLMJZJATUFX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- -1 methacrylic acid nitrile Chemical class 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER0041824 | 1965-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468939A1 true DE1468939A1 (de) | 1968-12-19 |
Family
ID=7406459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651468939 Pending DE1468939A1 (de) | 1965-10-23 | 1965-10-23 | Verfahren zur Herstellung von Methacrylsaeuremethylester |
Country Status (5)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0201307A1 (en) * | 1985-05-06 | 1986-11-12 | Rohm And Haas Company | Process for preparing unsaturated organic compounds |
| DE102006058251A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern |
-
1965
- 1965-10-23 DE DE19651468939 patent/DE1468939A1/de active Pending
-
1966
- 1966-07-19 BE BE684333D patent/BE684333A/xx unknown
- 1966-09-27 FR FR77760A patent/FR1508142A/fr not_active Expired
- 1966-10-11 GB GB45476/66A patent/GB1122546A/en not_active Expired
- 1966-10-21 NL NL6614956A patent/NL6614956A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0201307A1 (en) * | 1985-05-06 | 1986-11-12 | Rohm And Haas Company | Process for preparing unsaturated organic compounds |
| DE102006058251A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1508142A (fr) | 1968-01-05 |
| BE684333A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-03 |
| NL6614956A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-04-24 |
| GB1122546A (en) | 1968-08-07 |
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