DE2144150A1 - Verfahren zur oxydehydrierung organischer verbindungen - Google Patents
Verfahren zur oxydehydrierung organischer verbindungenInfo
- Publication number
- DE2144150A1 DE2144150A1 DE2144150A DE2144150A DE2144150A1 DE 2144150 A1 DE2144150 A1 DE 2144150A1 DE 2144150 A DE2144150 A DE 2144150A DE 2144150 A DE2144150 A DE 2144150A DE 2144150 A1 DE2144150 A1 DE 2144150A1
- Authority
- DE
- Germany
- Prior art keywords
- oxygen
- reactor
- gases
- ammonium halide
- hydrogen
- 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
- 238000000034 method Methods 0.000 title claims description 17
- 150000002894 organic compounds Chemical class 0.000 title claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 18
- -1 ammonium halide Chemical class 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000003546 flue gas Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002485 combustion reaction Methods 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003345 natural gas Substances 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical class [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 6
- 238000011144 upstream manufacturing Methods 0.000 description 5
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229940107816 ammonium iodide Drugs 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000002737 fuel gas Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- PRXLCSIMRQFQMX-UHFFFAOYSA-N [O].[I] Chemical compound [O].[I] PRXLCSIMRQFQMX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000000567 combustion gas Substances 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
- 229920001577 copolymer Polymers 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE788307D BE788307A (fr) | 1971-09-03 | Procede d'oxydeshydrogenation de composes organiques | |
| DE2144150A DE2144150A1 (de) | 1971-09-03 | 1971-09-03 | Verfahren zur oxydehydrierung organischer verbindungen |
| IT27812/72A IT963678B (it) | 1971-09-03 | 1972-08-02 | Processo per la ossideidrogenazio ne di composti organici |
| US00283986A US3821287A (en) | 1971-09-03 | 1972-08-28 | Oxidative dehydrogenation of methyl issbutgrate |
| NL7211768A NL7211768A (enExample) | 1971-09-03 | 1972-08-29 | |
| CA150,722A CA1010056A (en) | 1971-09-03 | 1972-08-30 | Oxidative dehydrogenation of organic compounds |
| FR7230912A FR2151026B1 (enExample) | 1971-09-03 | 1972-08-31 | |
| JP47087211A JPS4834101A (enExample) | 1971-09-03 | 1972-09-01 | |
| GB4063872A GB1398557A (en) | 1971-09-03 | 1972-09-01 | Dehydrogenation of organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2144150A DE2144150A1 (de) | 1971-09-03 | 1971-09-03 | Verfahren zur oxydehydrierung organischer verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2144150A1 true DE2144150A1 (de) | 1973-03-15 |
Family
ID=5818571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2144150A Pending DE2144150A1 (de) | 1971-09-03 | 1971-09-03 | Verfahren zur oxydehydrierung organischer verbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3821287A (enExample) |
| JP (1) | JPS4834101A (enExample) |
| BE (1) | BE788307A (enExample) |
| CA (1) | CA1010056A (enExample) |
| DE (1) | DE2144150A1 (enExample) |
| FR (1) | FR2151026B1 (enExample) |
| GB (1) | GB1398557A (enExample) |
| IT (1) | IT963678B (enExample) |
| NL (1) | NL7211768A (enExample) |
-
0
- BE BE788307D patent/BE788307A/xx unknown
-
1971
- 1971-09-03 DE DE2144150A patent/DE2144150A1/de active Pending
-
1972
- 1972-08-02 IT IT27812/72A patent/IT963678B/it active
- 1972-08-28 US US00283986A patent/US3821287A/en not_active Expired - Lifetime
- 1972-08-29 NL NL7211768A patent/NL7211768A/xx not_active Application Discontinuation
- 1972-08-30 CA CA150,722A patent/CA1010056A/en not_active Expired
- 1972-08-31 FR FR7230912A patent/FR2151026B1/fr not_active Expired
- 1972-09-01 GB GB4063872A patent/GB1398557A/en not_active Expired
- 1972-09-01 JP JP47087211A patent/JPS4834101A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2151026A1 (enExample) | 1973-04-13 |
| BE788307A (fr) | 1973-03-01 |
| GB1398557A (en) | 1975-06-25 |
| CA1010056A (en) | 1977-05-10 |
| US3821287A (en) | 1974-06-28 |
| JPS4834101A (enExample) | 1973-05-16 |
| NL7211768A (enExample) | 1973-03-06 |
| FR2151026B1 (enExample) | 1976-08-13 |
| IT963678B (it) | 1974-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |