DE1298991B - Verfahren zur Herstellung von Cyclohexenol - Google Patents
Verfahren zur Herstellung von CyclohexenolInfo
- Publication number
- DE1298991B DE1298991B DEC35517A DEC0035517A DE1298991B DE 1298991 B DE1298991 B DE 1298991B DE C35517 A DEC35517 A DE C35517A DE C0035517 A DEC0035517 A DE C0035517A DE 1298991 B DE1298991 B DE 1298991B
- Authority
- DE
- Germany
- Prior art keywords
- hydroperoxide
- cyclohexenol
- cyclohexene
- heavy metal
- decomposition
- 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.)
- Pending
Links
- QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical compound OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 title claims description 13
- PQANGXXSEABURG-UHFFFAOYSA-N cyclohexenol Natural products OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 13
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910001385 heavy metal Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- QEEPPWQOVJWUBC-UHFFFAOYSA-N 1-hydroperoxycyclohexene Chemical group OOC1=CCCCC1 QEEPPWQOVJWUBC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 4
- 239000002274 desiccant Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 7
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- -1 cyclohexene Chemical class 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AGJCMOLZDPMPNS-UHFFFAOYSA-N hydrogen peroxide hydrate Chemical compound O.OO.OO AGJCMOLZDPMPNS-UHFFFAOYSA-N 0.000 description 3
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 150000002432 hydroperoxides Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- CKMXAIVXVKGGFM-UHFFFAOYSA-N p-cumic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MGDMIHIUDQJWOA-UHFFFAOYSA-N 1-(cyclohexen-1-ylperoxy)cyclohexene Chemical group C1CCCC(OOC=2CCCCC=2)=C1 MGDMIHIUDQJWOA-UHFFFAOYSA-N 0.000 description 1
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical compound CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- FYTJMUYAPJUVHO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-6-ol Chemical compound C1CCCC2OC21O FYTJMUYAPJUVHO-UHFFFAOYSA-N 0.000 description 1
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical class [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XFXBZUGAKSVCJA-UHFFFAOYSA-N cycloheptene-1-carbaldehyde Chemical compound O=CC1=CCCCCC1 XFXBZUGAKSVCJA-UHFFFAOYSA-N 0.000 description 1
- FNTHQRXVZDCWSP-UHFFFAOYSA-N cyclohexane-1,1,2-triol Chemical compound OC1CCCCC1(O)O FNTHQRXVZDCWSP-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical class [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with unsaturation at least in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35517A DE1298991B (de) | 1965-04-06 | 1965-04-06 | Verfahren zur Herstellung von Cyclohexenol |
| FR54778A FR1471965A (fr) | 1965-04-06 | 1966-03-24 | Procédé de préparation du cyclohexanol |
| US538617A US3467720A (en) | 1965-04-06 | 1966-03-30 | Process for the production of cyclohexenol |
| GB15009/66A GB1135475A (en) | 1965-04-06 | 1966-04-05 | Process for the production of cyclohexanol |
| BE679156D BE679156A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-04-06 | 1966-04-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35517A DE1298991B (de) | 1965-04-06 | 1965-04-06 | Verfahren zur Herstellung von Cyclohexenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1298991B true DE1298991B (de) | 1969-07-10 |
Family
ID=7021845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC35517A Pending DE1298991B (de) | 1965-04-06 | 1965-04-06 | Verfahren zur Herstellung von Cyclohexenol |
Country Status (4)
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE625085A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE1002754B (de) * | 1954-05-12 | 1957-02-21 | Du Pont | Verfahren zur Herstellung von zur Adipinsaeureherstellung geeigneten Gemischen aus Cyclohexanon und Cyclohexanol |
| GB846847A (en) * | 1958-03-03 | 1960-08-31 | Inst Francais Du Petrole | An improved method of producing conjugated diolefines |
| FR1292244A (fr) * | 1961-03-17 | 1962-05-04 | Inst Francais Du Petrole | Nouveau procédé de fabrication d'hydroperoxydes d'oléfines |
| DE1129486B (de) * | 1957-09-04 | 1962-05-17 | Fine Organics Inc | Verfahren zur Herstellung von Hydroperoxyden durch Oxydation von Kohlenwasserstoffen |
| US3096376A (en) * | 1958-03-03 | 1963-07-02 | Clement Genevieve | Process for making cyclohexene hydroperoxides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2223500A (en) * | 1937-02-24 | 1940-12-03 | Du Pont | Oxidation of cyclic olefins |
| GB700546A (en) * | 1951-03-06 | 1953-12-02 | Du Pont | Hydroperoxides |
| US2974161A (en) * | 1958-04-25 | 1961-03-07 | Sinclair Refining Co | Olefin oxidation with a solid calcined catalyst |
| US3171864A (en) * | 1960-10-03 | 1965-03-02 | Inst Francais Du Petrole | Process for manufacturing conjugated diolefins |
-
1965
- 1965-04-06 DE DEC35517A patent/DE1298991B/de active Pending
-
1966
- 1966-03-30 US US538617A patent/US3467720A/en not_active Expired - Lifetime
- 1966-04-05 GB GB15009/66A patent/GB1135475A/en not_active Expired
- 1966-04-06 BE BE679156D patent/BE679156A/xx unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE625085A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE1002754B (de) * | 1954-05-12 | 1957-02-21 | Du Pont | Verfahren zur Herstellung von zur Adipinsaeureherstellung geeigneten Gemischen aus Cyclohexanon und Cyclohexanol |
| DE1129486B (de) * | 1957-09-04 | 1962-05-17 | Fine Organics Inc | Verfahren zur Herstellung von Hydroperoxyden durch Oxydation von Kohlenwasserstoffen |
| GB846847A (en) * | 1958-03-03 | 1960-08-31 | Inst Francais Du Petrole | An improved method of producing conjugated diolefines |
| US3096376A (en) * | 1958-03-03 | 1963-07-02 | Clement Genevieve | Process for making cyclohexene hydroperoxides |
| FR1292244A (fr) * | 1961-03-17 | 1962-05-04 | Inst Francais Du Petrole | Nouveau procédé de fabrication d'hydroperoxydes d'oléfines |
Also Published As
| Publication number | Publication date |
|---|---|
| BE679156A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-09-16 |
| GB1135475A (en) | 1968-12-04 |
| US3467720A (en) | 1969-09-16 |
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