DE1964964C - - Google Patents
Info
- Publication number
- DE1964964C DE1964964C DE19691964964 DE1964964A DE1964964C DE 1964964 C DE1964964 C DE 1964964C DE 19691964964 DE19691964964 DE 19691964964 DE 1964964 A DE1964964 A DE 1964964A DE 1964964 C DE1964964 C DE 1964964C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- alicyclic
- solvent
- oxygen
- polar
- 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
- WFPZPJSADLPSON-UHFFFAOYSA-N Dinitrogen tetroxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- -1 dinitrogen-oxygen Chemical compound 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical compound [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 229930015698 phenylpropenes Natural products 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1Z,5Z,9Z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 description 3
- 206010047289 Ventricular extrasystoles Diseases 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008079 hexane Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RDAFFINKUCJOJK-UYIJSCIWSA-N (1Z,5E)-cyclodeca-1,5-diene Chemical compound C1CC\C=C/CC\C=C\C1 RDAFFINKUCJOJK-UYIJSCIWSA-N 0.000 description 2
- SIKBTEDZSLYKRA-UHFFFAOYSA-N 2-nitrocyclododecan-1-one Chemical compound [O-][N+](=O)C1CCCCCCCCCCC1=O SIKBTEDZSLYKRA-UHFFFAOYSA-N 0.000 description 2
- QSJIVGDXHUYGKK-UHFFFAOYSA-N 2-nitrocyclooctan-1-one Chemical compound [O-][N+](=O)C1CCCCCCC1=O QSJIVGDXHUYGKK-UHFFFAOYSA-N 0.000 description 2
- URYYVOIYTNXXBN-UHFFFAOYSA-N cyclooctene Chemical compound [CH]1[CH]CCCCCC1 URYYVOIYTNXXBN-UHFFFAOYSA-N 0.000 description 2
- 239000004913 cyclooctene Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000001272 nitrous oxide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-Cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 1
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 1
- CHVJITGCYZJHLR-UHFFFAOYSA-N Cycloheptatriene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N Cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- PZIBOVBPVADPBS-UHFFFAOYSA-J S(=O)(=O)([O-])[O-].[Si+4].S(=O)(=O)([O-])[O-] Chemical compound S(=O)(=O)([O-])[O-].[Si+4].S(=O)(=O)([O-])[O-] PZIBOVBPVADPBS-UHFFFAOYSA-J 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 description 1
- RRKODOZNUZCUBN-UHFFFAOYSA-N cycloocta-1,3-diene Chemical compound C1CCC=CC=CC1 RRKODOZNUZCUBN-UHFFFAOYSA-N 0.000 description 1
- GMUVJAZTJOCSND-OWOJBTEDSA-N cycloundecene Chemical compound C1CCCC\C=C\CCCC1 GMUVJAZTJOCSND-OWOJBTEDSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- YTPLVOOAFADQJP-UHFFFAOYSA-N dodeca-1,3,5-triene Chemical compound CCCCCCC=CC=CC=C YTPLVOOAFADQJP-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78833068A | 1968-12-31 | 1968-12-31 | |
| US78833068 | 1968-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1964964A1 DE1964964A1 (de) | 1970-09-03 |
| DE1964964C true DE1964964C (US06724976-20040420-M00002.png) | 1973-05-17 |
Family
ID=25144163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691964964 Granted DE1964964A1 (de) | 1968-12-31 | 1969-12-24 | Verfahren zur Herstellung von alicyclischen alpha-Nitroketonen |
Country Status (6)
-
1969
- 1969-12-15 GB GB1239115D patent/GB1239115A/en not_active Expired
- 1969-12-17 NL NL6918961A patent/NL6918961A/xx unknown
- 1969-12-24 DE DE19691964964 patent/DE1964964A1/de active Granted
- 1969-12-29 JP JP44105395A patent/JPS51107B1/ja active Pending
- 1969-12-31 FR FR6945725A patent/FR2027613A1/fr not_active Withdrawn
- 1969-12-31 BE BE743954D patent/BE743954A/xx unknown
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