DE1643195C - - Google Patents
Info
- Publication number
- DE1643195C DE1643195C DE19671643195 DE1643195A DE1643195C DE 1643195 C DE1643195 C DE 1643195C DE 19671643195 DE19671643195 DE 19671643195 DE 1643195 A DE1643195 A DE 1643195A DE 1643195 C DE1643195 C DE 1643195C
- Authority
- DE
- Germany
- Prior art keywords
- diketene
- sodium
- acid
- alcohol
- reaction
- 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
- WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 5
- 235000017281 sodium acetate Nutrition 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M Sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 8
- 150000001298 alcohols Chemical class 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 238000009835 boiling Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating Effects 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 238000007086 side reaction Methods 0.000 claims 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- -1 Acetoacetic acid ester Chemical class 0.000 claims 2
- 241000220317 Rosa Species 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 150000001447 alkali salts Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N 3-acetyl-6-methylpyran-2,4-dione Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims 1
- 241000282941 Rangifer tarandus Species 0.000 claims 1
- 239000004115 Sodium Silicate Substances 0.000 claims 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M Sodium stearate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 claims 1
- 150000004720 acetoacetic acids Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000003980 alpha-chlorocarboxylic acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 235000015872 dietary supplement Nutrition 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 235000015243 ice cream Nutrition 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 230000001264 neutralization Effects 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052911 sodium silicate Inorganic materials 0.000 claims 1
- 239000004328 sodium tetraborate Substances 0.000 claims 1
- 235000010339 sodium tetraborate Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M Sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- FHSUFDYFOHSYHI-UHFFFAOYSA-M 3-oxopentanoate Chemical compound CCC(=O)CC([O-])=O FHSUFDYFOHSYHI-UHFFFAOYSA-M 0.000 description 1
- 229940089960 Chloroacetate Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- KPFSGNRRZMYZPH-UHFFFAOYSA-M potassium;2-chloroacetate Chemical compound [K+].[O-]C(=O)CCl KPFSGNRRZMYZPH-UHFFFAOYSA-M 0.000 description 1
- 229940075581 sodium bromide Drugs 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW0043137 | 1967-01-10 | ||
| DEW0043137 | 1967-01-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643195A1 DE1643195A1 (de) | 1972-01-27 |
| DE1643195C true DE1643195C (xx) | 1973-04-19 |
Family
ID=7603535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643195 Granted DE1643195A1 (de) | 1967-01-10 | 1967-01-10 | Verfahren zur Herstellung von Acetessigsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3549693A (xx) |
| BE (1) | BE709080A (xx) |
| CH (1) | CH485641A (xx) |
| DE (1) | DE1643195A1 (xx) |
| FR (1) | FR1550747A (xx) |
| GB (1) | GB1177591A (xx) |
| NL (1) | NL158780B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2558517C2 (de) * | 1975-12-24 | 1983-11-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 4-Methyl-imidazol-5-carbonsäureisopropylester |
| EP3728487A4 (en) | 2017-12-22 | 2021-11-03 | Fourth Principle, LLC. | COMPOSITIONS INCLUDING CETO-ESTER COMPOUNDS AND METHODS OF USE THEREOF |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290127B (de) * | 1964-06-26 | 1969-03-06 | Hoechst Ag | Verfahren zur Herstellung von Acetessigsaeureestern |
-
1967
- 1967-01-10 DE DE19671643195 patent/DE1643195A1/de active Granted
-
1968
- 1968-01-02 NL NL6800019.A patent/NL158780B/xx not_active IP Right Cessation
- 1968-01-03 US US695343A patent/US3549693A/en not_active Expired - Lifetime
- 1968-01-05 GB GB848/68A patent/GB1177591A/en not_active Expired
- 1968-01-08 BE BE709080D patent/BE709080A/xx unknown
- 1968-01-09 FR FR1550747D patent/FR1550747A/fr not_active Expired
- 1968-01-09 CH CH27768A patent/CH485641A/de not_active IP Right Cessation
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