DE3024535A1 - Verfahren zur herstellung von acetessigsaeurealkylestern - Google Patents
Verfahren zur herstellung von acetessigsaeurealkylesternInfo
- Publication number
- DE3024535A1 DE3024535A1 DE19803024535 DE3024535A DE3024535A1 DE 3024535 A1 DE3024535 A1 DE 3024535A1 DE 19803024535 DE19803024535 DE 19803024535 DE 3024535 A DE3024535 A DE 3024535A DE 3024535 A1 DE3024535 A1 DE 3024535A1
- Authority
- DE
- Germany
- Prior art keywords
- acid alkyl
- ester
- mixture
- alkyl ester
- acetoacetate
- 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.)
- Withdrawn
Links
- 150000002148 esters Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- -1 alkyl acetoacetates Chemical class 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 18
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 11
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- NTUIQDQTOGRCPP-UHFFFAOYSA-N methyl 4-acetyloxybut-3-enoate Chemical compound COC(=O)CC=COC(C)=O NTUIQDQTOGRCPP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- ZRTYWWLEANWADO-DAXSKMNVSA-N ethyl (Z)-2-acetyloxybut-2-enoate Chemical compound CCOC(=O)C(=C\C)\OC(C)=O ZRTYWWLEANWADO-DAXSKMNVSA-N 0.000 description 5
- BIYHFDWODFSWQJ-UHFFFAOYSA-N ethyl 4-acetyloxybut-3-enoate Chemical compound C(C)OC(CC=COC(C)=O)=O BIYHFDWODFSWQJ-UHFFFAOYSA-N 0.000 description 5
- AAROSGFSRQVZGL-XQRVVYSFSA-N methyl (z)-2-acetyloxybut-2-enoate Chemical compound COC(=O)C(=C\C)\OC(C)=O AAROSGFSRQVZGL-XQRVVYSFSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MUUKISYMZRAJKG-UHFFFAOYSA-N CC(=C(C(=O)O)OC(C)=O)C Chemical compound CC(=C(C(=O)O)OC(C)=O)C MUUKISYMZRAJKG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- DMZPWBTUMHDJNK-HYXAFXHYSA-N (z)-2-acetyloxybut-2-enoic acid Chemical compound C\C=C(C(O)=O)/OC(C)=O DMZPWBTUMHDJNK-HYXAFXHYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 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 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- TYAUGADAWWKDOH-UHFFFAOYSA-N methanol;methyl 3-oxobutanoate Chemical compound OC.COC(=O)CC(C)=O TYAUGADAWWKDOH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010626 work up procedure 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803024535 DE3024535A1 (de) | 1980-06-28 | 1980-06-28 | Verfahren zur herstellung von acetessigsaeurealkylestern |
| EP81104851A EP0043088B1 (de) | 1980-06-28 | 1981-06-23 | Verfahren zur Herstellung von Acetessigsäurealkylestern |
| DE8181104851T DE3161956D1 (en) | 1980-06-28 | 1981-06-23 | Process for the production of alkyl esters of acetoactic acid |
| JP9845281A JPS5738748A (en) | 1980-06-28 | 1981-06-26 | Manufacture of acetoacetic acid alkyl ester |
| CA000380711A CA1152528A (en) | 1980-06-28 | 1981-06-26 | Process for the preparation of acetoacetic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803024535 DE3024535A1 (de) | 1980-06-28 | 1980-06-28 | Verfahren zur herstellung von acetessigsaeurealkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3024535A1 true DE3024535A1 (de) | 1982-01-28 |
Family
ID=6105883
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803024535 Withdrawn DE3024535A1 (de) | 1980-06-28 | 1980-06-28 | Verfahren zur herstellung von acetessigsaeurealkylestern |
| DE8181104851T Expired DE3161956D1 (en) | 1980-06-28 | 1981-06-23 | Process for the production of alkyl esters of acetoactic acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181104851T Expired DE3161956D1 (en) | 1980-06-28 | 1981-06-23 | Process for the production of alkyl esters of acetoactic acid |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0043088B1 (forum.php) |
| JP (1) | JPS5738748A (forum.php) |
| CA (1) | CA1152528A (forum.php) |
| DE (2) | DE3024535A1 (forum.php) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2900311A (en) * | 1952-10-11 | 1959-08-18 | Union Carbide Corp | Purification of acetoacetic esters by distillation |
-
1980
- 1980-06-28 DE DE19803024535 patent/DE3024535A1/de not_active Withdrawn
-
1981
- 1981-06-23 EP EP81104851A patent/EP0043088B1/de not_active Expired
- 1981-06-23 DE DE8181104851T patent/DE3161956D1/de not_active Expired
- 1981-06-26 JP JP9845281A patent/JPS5738748A/ja active Granted
- 1981-06-26 CA CA000380711A patent/CA1152528A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0043088B1 (de) | 1984-01-18 |
| CA1152528A (en) | 1983-08-23 |
| JPH0251891B2 (forum.php) | 1990-11-08 |
| EP0043088A1 (de) | 1982-01-06 |
| JPS5738748A (en) | 1982-03-03 |
| DE3161956D1 (en) | 1984-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |