DE2222669A1 - Verfahren zur herstellung von methylmethacrylat - Google Patents
Verfahren zur herstellung von methylmethacrylatInfo
- Publication number
- DE2222669A1 DE2222669A1 DE19722222669 DE2222669A DE2222669A1 DE 2222669 A1 DE2222669 A1 DE 2222669A1 DE 19722222669 DE19722222669 DE 19722222669 DE 2222669 A DE2222669 A DE 2222669A DE 2222669 A1 DE2222669 A1 DE 2222669A1
- Authority
- DE
- Germany
- Prior art keywords
- bath
- methanol
- acid
- reaction
- water
- 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 11
- -1 aryl sulfonic acid Chemical compound 0.000 claims description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims description 2
- 229960000907 methylthioninium chloride Drugs 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 244000261422 Lysimachia clethroides Species 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- JIRULJUIQOAJPM-UHFFFAOYSA-N 3-methoxy-2-methylpropanoic acid Chemical compound COCC(C)C(O)=O JIRULJUIQOAJPM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
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 |
|---|---|---|---|
| FR7122946A FR2142305A5 (enExample) | 1971-06-17 | 1971-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2222669A1 true DE2222669A1 (de) | 1973-01-04 |
Family
ID=9079176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722222669 Pending DE2222669A1 (de) | 1971-06-17 | 1972-05-09 | Verfahren zur herstellung von methylmethacrylat |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3836575A (enExample) |
| BE (1) | BE785045A (enExample) |
| BR (1) | BR7203389D0 (enExample) |
| CA (1) | CA953734A (enExample) |
| CH (1) | CH552555A (enExample) |
| DD (1) | DD98508A5 (enExample) |
| DE (1) | DE2222669A1 (enExample) |
| FR (1) | FR2142305A5 (enExample) |
| IT (1) | IT956101B (enExample) |
| NL (1) | NL7207382A (enExample) |
| RO (1) | RO59094A (enExample) |
| SU (1) | SU424347A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19536183A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure |
-
1971
- 1971-06-17 FR FR7122946A patent/FR2142305A5/fr not_active Expired
-
1972
- 1972-05-09 DE DE19722222669 patent/DE2222669A1/de active Pending
- 1972-05-10 CH CH697572A patent/CH552555A/fr not_active IP Right Cessation
- 1972-05-12 RO RO70869A patent/RO59094A/ro unknown
- 1972-05-26 BR BR3389/72A patent/BR7203389D0/pt unknown
- 1972-05-30 SU SU1788175A patent/SU424347A3/ru active
- 1972-05-31 IT IT25194/72A patent/IT956101B/it active
- 1972-06-01 NL NL7207382A patent/NL7207382A/xx unknown
- 1972-06-05 CA CA143,905A patent/CA953734A/en not_active Expired
- 1972-06-12 DD DD163625A patent/DD98508A5/xx unknown
- 1972-06-16 BE BE785045A patent/BE785045A/xx unknown
- 1972-06-19 US US00263846A patent/US3836575A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7207382A (enExample) | 1972-12-19 |
| IT956101B (it) | 1973-10-10 |
| BR7203389D0 (pt) | 1973-06-14 |
| CH552555A (fr) | 1974-08-15 |
| FR2142305A5 (enExample) | 1973-01-26 |
| US3836575A (en) | 1974-09-17 |
| DD98508A5 (enExample) | 1973-06-20 |
| RO59094A (enExample) | 1975-10-15 |
| BE785045A (fr) | 1972-12-18 |
| CA953734A (en) | 1974-08-27 |
| SU424347A3 (ru) | 1974-04-15 |
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