DE2523764A1 - Verfahren zur herstellung von alpha-beta-ungesaettigten alkoholen - Google Patents
Verfahren zur herstellung von alpha-beta-ungesaettigten alkoholenInfo
- Publication number
- DE2523764A1 DE2523764A1 DE19752523764 DE2523764A DE2523764A1 DE 2523764 A1 DE2523764 A1 DE 2523764A1 DE 19752523764 DE19752523764 DE 19752523764 DE 2523764 A DE2523764 A DE 2523764A DE 2523764 A1 DE2523764 A1 DE 2523764A1
- Authority
- DE
- Germany
- Prior art keywords
- allene
- mercury
- water
- hours
- nitrate
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 20
- 150000001298 alcohols Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001361 allenes Chemical class 0.000 claims description 8
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 claims description 6
- -1 acyclic allene Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002730 mercury Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000003046 allene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910001987 mercury nitrate Inorganic materials 0.000 description 6
- DRXYRSRECMWYAV-UHFFFAOYSA-N nitrooxymercury Chemical compound [Hg+].[O-][N+]([O-])=O DRXYRSRECMWYAV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- IQEPFWDDSIGKBH-UHFFFAOYSA-N cyclopentadeca-1,2-diene Chemical compound C1CCCCCCC=C=CCCCCC1 IQEPFWDDSIGKBH-UHFFFAOYSA-N 0.000 description 2
- GXKXSGKUODLRSQ-UHFFFAOYSA-N cyclotrideca-1,2-diene Chemical compound C1CCCCCC=C=CCCCC1 GXKXSGKUODLRSQ-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GYTDJCTUFWFXBE-UHFFFAOYSA-M (2,2,2-trifluoroacetyl)oxymercury Chemical compound [Hg+].[O-]C(=O)C(F)(F)F GYTDJCTUFWFXBE-UHFFFAOYSA-M 0.000 description 1
- SPWMFXSIAMGJPC-XQRVVYSFSA-N (z)-hex-2-en-3-ol Chemical compound CCC\C(O)=C\C SPWMFXSIAMGJPC-XQRVVYSFSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WAMOTICFHBWHDN-UHFFFAOYSA-N cyclopentadec-2-en-1-ol Chemical compound OC1CCCCCCCCCCCCC=C1 WAMOTICFHBWHDN-UHFFFAOYSA-N 0.000 description 1
- AHWMKJRUMHXULY-UHFFFAOYSA-N cyclopentadeca-1,3-diene Chemical compound C1CCCCCC=CC=CCCCCC1 AHWMKJRUMHXULY-UHFFFAOYSA-N 0.000 description 1
- QPFZUISGBBUKRA-UHFFFAOYSA-N cyclotridec-2-en-1-ol Chemical compound OC1CCCCCCCCCCC=C1 QPFZUISGBBUKRA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- SMOVOSVEEFIBSP-UHFFFAOYSA-N hex-3-en-2-ol Chemical compound CCC=CC(C)O SMOVOSVEEFIBSP-UHFFFAOYSA-N 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 229940008718 metallic mercury Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2406974A GB1443304A (en) | 1974-05-30 | 1974-05-30 | Preparation of alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2523764A1 true DE2523764A1 (de) | 1975-12-11 |
Family
ID=10205876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752523764 Withdrawn DE2523764A1 (de) | 1974-05-30 | 1975-05-28 | Verfahren zur herstellung von alpha-beta-ungesaettigten alkoholen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS511405A (enrdf_load_stackoverflow) |
| BE (1) | BE829235A (enrdf_load_stackoverflow) |
| CH (1) | CH599081A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2523764A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2272970B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1443304A (enrdf_load_stackoverflow) |
| NL (1) | NL7506267A (enrdf_load_stackoverflow) |
-
1974
- 1974-05-30 GB GB2406974A patent/GB1443304A/en not_active Expired
-
1975
- 1975-05-20 BE BE1006672A patent/BE829235A/xx unknown
- 1975-05-28 DE DE19752523764 patent/DE2523764A1/de not_active Withdrawn
- 1975-05-28 FR FR7516613A patent/FR2272970B1/fr not_active Expired
- 1975-05-28 JP JP50063105A patent/JPS511405A/ja active Pending
- 1975-05-28 CH CH684275A patent/CH599081A5/xx not_active IP Right Cessation
- 1975-05-28 NL NL7506267A patent/NL7506267A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7506267A (nl) | 1975-12-02 |
| JPS511405A (enrdf_load_stackoverflow) | 1976-01-08 |
| GB1443304A (en) | 1976-07-21 |
| CH599081A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| BE829235A (nl) | 1975-11-20 |
| FR2272970B1 (enrdf_load_stackoverflow) | 1978-02-03 |
| FR2272970A1 (enrdf_load_stackoverflow) | 1975-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |