DE1717151B1 - Verfahren zur Herstellung von Hexanon-(2) oder Hexanon-(3) durch katalytische Dehydrierung von Hexanol-(2) oder Hexanol-(3) - Google Patents
Verfahren zur Herstellung von Hexanon-(2) oder Hexanon-(3) durch katalytische Dehydrierung von Hexanol-(2) oder Hexanol-(3)Info
- Publication number
- DE1717151B1 DE1717151B1 DE19661717151 DE1717151A DE1717151B1 DE 1717151 B1 DE1717151 B1 DE 1717151B1 DE 19661717151 DE19661717151 DE 19661717151 DE 1717151 A DE1717151 A DE 1717151A DE 1717151 B1 DE1717151 B1 DE 1717151B1
- Authority
- DE
- Germany
- Prior art keywords
- hexanol
- hexanone
- catalyst
- preparation
- dehydrogenation
- 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
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 230000003197 catalytic effect Effects 0.000 title claims description 6
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 title claims description 5
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 title claims description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 24
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 239000011787 zinc oxide Substances 0.000 claims description 9
- 239000008262 pumice Substances 0.000 claims description 6
- 239000004575 stone Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- 239000010949 copper Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- WUCBICXOWNTEAT-UHFFFAOYSA-N [O--].[O--].[Ni++].[Zn++] Chemical compound [O--].[O--].[Ni++].[Zn++] WUCBICXOWNTEAT-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic secondary alcohols Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exhaust Gas Treatment By Means Of Catalyst (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2766865A GB1111416A (en) | 1965-06-30 | 1965-06-30 | Dehydrogenation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1717151B1 true DE1717151B1 (de) | 1971-10-21 |
Family
ID=10263333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661717151 Pending DE1717151B1 (de) | 1965-06-30 | 1966-06-10 | Verfahren zur Herstellung von Hexanon-(2) oder Hexanon-(3) durch katalytische Dehydrierung von Hexanol-(2) oder Hexanol-(3) |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE683448A (enExample) |
| DE (1) | DE1717151B1 (enExample) |
| GB (1) | GB1111416A (enExample) |
| NL (1) | NL148299B (enExample) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE832292C (de) * | 1950-03-07 | 1952-02-21 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung von Butyraldehyd |
| DE854351C (de) * | 1940-02-16 | 1952-11-04 | Basf Ag | Verfahren zur Herstellung von Propionaldehyd |
| DE863459C (de) * | 1946-07-08 | 1953-01-19 | Trico Folberth Ltd | Vorrichtung zum Anbringen eines Scheibenwischerarmes auf einer hin und her gehenden Spindel |
| DE1016695B (de) * | 1954-02-26 | 1957-10-03 | Knapsack Ag | Verfahren zur Dehydrierung von sekundaeren Alkoholen zu Ketonen |
| DE1026739B (de) * | 1955-02-08 | 1958-03-27 | Knapsack Ag | Verfahren zur Dehydrierung niedrigmolekularer, aliphatischer, sekundaerer Alkohole zu den entsprechenden Ketonen |
| DE1055520B (de) * | 1956-01-31 | 1959-04-23 | Rheinpreussen Ag | Verfahren zur Dehydrierung von Alkoholen |
| DE1064484B (de) * | 1957-04-25 | 1959-09-03 | Leuna Werke Veb | Verfahren zur Darstellung hochaktiver Mischkatalysatoren |
| US3053898A (en) * | 1959-07-21 | 1962-09-11 | Exxon Research Engineering Co | Preparation of ketones from secondary alcohols |
| DE1147933B (de) * | 1958-01-30 | 1963-05-02 | Rheinpreussen Ag | Verfahren zur katalytischen Dehydrierung von Alkoholen durch thermische Zersetzung |
-
1965
- 1965-06-30 GB GB2766865A patent/GB1111416A/en not_active Expired
-
1966
- 1966-06-10 DE DE19661717151 patent/DE1717151B1/de active Pending
- 1966-06-23 NL NL6608721A patent/NL148299B/xx unknown
- 1966-06-30 BE BE683448D patent/BE683448A/xx unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE854351C (de) * | 1940-02-16 | 1952-11-04 | Basf Ag | Verfahren zur Herstellung von Propionaldehyd |
| DE863459C (de) * | 1946-07-08 | 1953-01-19 | Trico Folberth Ltd | Vorrichtung zum Anbringen eines Scheibenwischerarmes auf einer hin und her gehenden Spindel |
| DE832292C (de) * | 1950-03-07 | 1952-02-21 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung von Butyraldehyd |
| DE1016695B (de) * | 1954-02-26 | 1957-10-03 | Knapsack Ag | Verfahren zur Dehydrierung von sekundaeren Alkoholen zu Ketonen |
| DE1026739B (de) * | 1955-02-08 | 1958-03-27 | Knapsack Ag | Verfahren zur Dehydrierung niedrigmolekularer, aliphatischer, sekundaerer Alkohole zu den entsprechenden Ketonen |
| DE1055520B (de) * | 1956-01-31 | 1959-04-23 | Rheinpreussen Ag | Verfahren zur Dehydrierung von Alkoholen |
| DE1064484B (de) * | 1957-04-25 | 1959-09-03 | Leuna Werke Veb | Verfahren zur Darstellung hochaktiver Mischkatalysatoren |
| DE1147933B (de) * | 1958-01-30 | 1963-05-02 | Rheinpreussen Ag | Verfahren zur katalytischen Dehydrierung von Alkoholen durch thermische Zersetzung |
| US3053898A (en) * | 1959-07-21 | 1962-09-11 | Exxon Research Engineering Co | Preparation of ketones from secondary alcohols |
Also Published As
| Publication number | Publication date |
|---|---|
| NL148299B (nl) | 1976-01-15 |
| GB1111416A (en) | 1968-04-24 |
| BE683448A (enExample) | 1966-12-30 |
| NL6608721A (enExample) | 1967-01-02 |
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