DE2012093C - - Google Patents
Info
- Publication number
- DE2012093C DE2012093C DE19702012093 DE2012093A DE2012093C DE 2012093 C DE2012093 C DE 2012093C DE 19702012093 DE19702012093 DE 19702012093 DE 2012093 A DE2012093 A DE 2012093A DE 2012093 C DE2012093 C DE 2012093C
- Authority
- DE
- Germany
- Prior art keywords
- pyrolysis
- ketone
- methyl
- acetate
- group
- 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
- 150000002576 ketones Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
- 239000007858 starting material Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- -1 alkyl cyclopentyl ketones Chemical class 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 4
- 150000001793 charged compounds Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- VZRXWNVJPINTDV-UHFFFAOYSA-N 1-(3-propan-2-ylcyclopentyl)ethanone Chemical compound CC(C)C1CCC(C(C)=O)C1 VZRXWNVJPINTDV-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AEJVFGYEZXMAPQ-UHFFFAOYSA-N 1-(6,6-dimethyl-3-bicyclo[3.1.0]hexanyl)ethanone Chemical compound C1C(C(=O)C)CC2C(C)(C)C12 AEJVFGYEZXMAPQ-UHFFFAOYSA-N 0.000 description 2
- KEAQFUVPVXQRBA-UHFFFAOYSA-N C(C)(C)C1(CC(CC1)C)C(=O)C1(CC(CC1)C)C(C)C Chemical compound C(C)(C)C1(CC(CC1)C)C(=O)C1(CC(CC1)C)C(C)C KEAQFUVPVXQRBA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- BWRHOYDPVJPXMF-UHFFFAOYSA-N carane Chemical compound C1C(C)CCC2C(C)(C)C12 BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- JWQKMEKSFPNAIB-SNVBAGLBSA-N (5r)-1-methyl-5-prop-1-en-2-ylcyclohexene Chemical class CC(=C)[C@@H]1CCC=C(C)C1 JWQKMEKSFPNAIB-SNVBAGLBSA-N 0.000 description 1
- WDBNFGAUCPWHLN-UHFFFAOYSA-N 1-(3-prop-1-en-2-ylcyclopentyl)ethanone Chemical compound CC(=C)C1CCC(C(C)=O)C1 WDBNFGAUCPWHLN-UHFFFAOYSA-N 0.000 description 1
- GEUINYLILIYHOG-UHFFFAOYSA-N 2-methyl-1-(3-methylcyclopentyl)propan-1-one Chemical compound CC(C)C(=O)C1CCC(C)C1 GEUINYLILIYHOG-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GCPZLJNKHNJVGF-HTQZYQBOSA-N [(1r,2r)-2-hydroxycyclohexyl] acetate Chemical compound CC(=O)O[C@@H]1CCCC[C@H]1O GCPZLJNKHNJVGF-HTQZYQBOSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- OGLDWXZKYODSOB-SNVBAGLBSA-N alpha-phellandrene Natural products CC(C)[C@H]1CC=C(C)C=C1 OGLDWXZKYODSOB-SNVBAGLBSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 229930006741 carane Natural products 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YYCPSEFQLGXPCO-UHFFFAOYSA-N xi-p-Menth-3-ene Chemical compound CC(C)C1=CCC(C)CC1 YYCPSEFQLGXPCO-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80712069A | 1969-03-13 | 1969-03-13 | |
| US80712069 | 1969-03-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2012093A1 DE2012093A1 (enExample) | 1971-02-25 |
| DE2012093C true DE2012093C (enExample) | 1973-04-26 |
Family
ID=
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