DE2652863C3 - - Google Patents
Info
- Publication number
- DE2652863C3 DE2652863C3 DE2652863C3 DE 2652863 C3 DE2652863 C3 DE 2652863C3 DE 2652863 C3 DE2652863 C3 DE 2652863C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- reaction
- methylbutenol
- acetoacetic acid
- reaction mixture
- 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.)
- Active
Links
- -1 acetoacetic acid ester Chemical class 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 32
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 23
- VBPSVYDSYVJIPX-UHFFFAOYSA-N pent-2-en-2-ol Chemical compound CCC=C(C)O VBPSVYDSYVJIPX-UHFFFAOYSA-N 0.000 claims description 19
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052782 aluminium Inorganic materials 0.000 claims description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N Isoprenyl alcohol Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- FHSUFDYFOHSYHI-UHFFFAOYSA-M 3-oxopentanoate Chemical compound CCC(=O)CC([O-])=O FHSUFDYFOHSYHI-UHFFFAOYSA-M 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 7
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- GCXJINGJZAOJHR-UHFFFAOYSA-N 2-methylacetoacetic acid Chemical compound CC(=O)C(C)C(O)=O GCXJINGJZAOJHR-UHFFFAOYSA-N 0.000 description 3
- WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- RTYRONIMTRDBLT-UHFFFAOYSA-N hept-5-en-2-one Chemical compound CC=CCCC(C)=O RTYRONIMTRDBLT-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FVOALQOAKFPOCF-UHFFFAOYSA-N 3-methylpent-2-en-2-ol Chemical compound CCC(C)=C(C)O FVOALQOAKFPOCF-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (Z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-Pentanol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- SYRKLPUYGHMXDN-UHFFFAOYSA-N 2-methylquinoline-5,8-dione Chemical compound O=C1C=CC(=O)C2=NC(C)=CC=C21 SYRKLPUYGHMXDN-UHFFFAOYSA-N 0.000 description 1
- UTTHSCJYARGIIW-UHFFFAOYSA-M 3-oxobutanoyloxyaluminum Chemical compound CC(=O)CC(=O)O[Al] UTTHSCJYARGIIW-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- NTDURBZYFOSETC-UHFFFAOYSA-N C(CC(=O)C)(=O)OC(=CCC)C Chemical compound C(CC(=O)C)(=O)OC(=CCC)C NTDURBZYFOSETC-UHFFFAOYSA-N 0.000 description 1
- 101700074212 CYTX Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 101700079974 OV17 Proteins 0.000 description 1
- JXRCCBGRGLINST-UHFFFAOYSA-L [Al+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O Chemical compound [Al+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O JXRCCBGRGLINST-UHFFFAOYSA-L 0.000 description 1
- IWAUTUCYWHZANT-UHFFFAOYSA-M [Al+3].CC(C)[O-].CC(C)[O-].CC(=O)CC([O-])=O Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(=O)CC([O-])=O IWAUTUCYWHZANT-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DEVXQDKRGJCZMV-UHFFFAOYSA-K aluminum;3-oxobutanoate Chemical compound [Al+3].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O DEVXQDKRGJCZMV-UHFFFAOYSA-K 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Family
ID=
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