DE1768960A1 - Verfahren zur Herstellung von Acetessigsaeureestern - Google Patents
Verfahren zur Herstellung von AcetessigsaeureesternInfo
- Publication number
- DE1768960A1 DE1768960A1 DE19681768960 DE1768960A DE1768960A1 DE 1768960 A1 DE1768960 A1 DE 1768960A1 DE 19681768960 DE19681768960 DE 19681768960 DE 1768960 A DE1768960 A DE 1768960A DE 1768960 A1 DE1768960 A1 DE 1768960A1
- Authority
- DE
- Germany
- Prior art keywords
- acid ester
- acetoacetic acid
- reaction
- diketene
- reaction product
- 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
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- -1 acetoacetic acid ester Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000006227 byproduct Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1068567A CH478751A (de) | 1967-07-27 | 1967-07-27 | Verfahren zur Herstellung von Acetessigsäureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768960A1 true DE1768960A1 (de) | 1972-01-13 |
Family
ID=4365749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768960 Pending DE1768960A1 (de) | 1967-07-27 | 1968-07-17 | Verfahren zur Herstellung von Acetessigsaeureestern |
Country Status (11)
-
1967
- 1967-07-27 CH CH1068567A patent/CH478751A/de not_active IP Right Cessation
-
1968
- 1968-07-17 DE DE19681768960 patent/DE1768960A1/de active Pending
- 1968-07-23 GB GB1225867D patent/GB1225867A/en not_active Expired
- 1968-07-25 FR FR1575144D patent/FR1575144A/fr not_active Expired
- 1968-07-25 NO NO294068A patent/NO125973B/no unknown
- 1968-07-25 CS CS543468A patent/CS153466B2/cs unknown
- 1968-07-25 AT AT723968A patent/AT278732B/de not_active IP Right Cessation
- 1968-07-26 NL NL6810616A patent/NL6810616A/xx unknown
- 1968-07-26 BE BE718690D patent/BE718690A/xx unknown
- 1968-07-26 DK DK361968A patent/DK129831B/da unknown
- 1968-07-26 SE SE1020968A patent/SE354468B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO125973B (enrdf_load_stackoverflow) | 1972-12-04 |
| DK129831B (da) | 1974-11-25 |
| NL6810616A (enrdf_load_stackoverflow) | 1969-01-29 |
| FR1575144A (enrdf_load_stackoverflow) | 1969-07-18 |
| SE354468B (enrdf_load_stackoverflow) | 1973-03-12 |
| GB1225867A (enrdf_load_stackoverflow) | 1971-03-24 |
| CS153466B2 (enrdf_load_stackoverflow) | 1974-02-25 |
| BE718690A (enrdf_load_stackoverflow) | 1968-12-31 |
| DK129831C (enrdf_load_stackoverflow) | 1975-05-12 |
| CH478751A (de) | 1969-09-30 |
| AT278732B (de) | 1970-02-10 |
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