DE2122750A1 - - Google Patents
Info
- Publication number
- DE2122750A1 DE2122750A1 DE19712122750 DE2122750A DE2122750A1 DE 2122750 A1 DE2122750 A1 DE 2122750A1 DE 19712122750 DE19712122750 DE 19712122750 DE 2122750 A DE2122750 A DE 2122750A DE 2122750 A1 DE2122750 A1 DE 2122750A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- initiator
- liquid
- oxygen
- aldehyde
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 77
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 56
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 239000003999 initiator Substances 0.000 claims description 39
- 239000001301 oxygen Substances 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 239000007788 liquid Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 31
- 150000001299 aldehydes Chemical class 0.000 claims description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
- 239000005977 Ethylene Substances 0.000 claims description 27
- 239000007789 gas Substances 0.000 claims description 27
- 239000012429 reaction media Substances 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- 150000002576 ketones Chemical class 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims description 7
- -1 olefin hydrocarbon Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 150000001336 alkenes Chemical class 0.000 description 32
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 230000003797 telogen phase Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 229910002090 carbon oxide Inorganic materials 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- FEWIGMWODIRUJM-UHFFFAOYSA-N 4-hexen-3-one Chemical compound CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3589370A | 1970-05-08 | 1970-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2122750A1 true DE2122750A1 (enrdf_load_stackoverflow) | 1971-11-25 |
Family
ID=21885414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712122750 Pending DE2122750A1 (enrdf_load_stackoverflow) | 1970-05-08 | 1971-05-07 |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE766856A (enrdf_load_stackoverflow) |
| DE (1) | DE2122750A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2091364A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1296503A (enrdf_load_stackoverflow) |
| NL (1) | NL7106202A (enrdf_load_stackoverflow) |
-
1971
- 1971-05-05 GB GB1296503D patent/GB1296503A/en not_active Expired
- 1971-05-06 NL NL7106202A patent/NL7106202A/xx unknown
- 1971-05-07 DE DE19712122750 patent/DE2122750A1/de active Pending
- 1971-05-07 FR FR7116650A patent/FR2091364A5/fr not_active Expired
- 1971-05-07 BE BE766856A patent/BE766856A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE766856A (fr) | 1971-10-01 |
| FR2091364A5 (enrdf_load_stackoverflow) | 1972-01-14 |
| GB1296503A (enrdf_load_stackoverflow) | 1972-11-15 |
| NL7106202A (enrdf_load_stackoverflow) | 1971-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60314010T2 (de) | Verfahren zur reduzierung der aldehydkonzentration in einer mischung die cyclohexanon und ein oder mehrere aldehyde enthält | |
| DE69007323T2 (de) | Verfahren zur Herstellung von sec.-Butylbenzol. | |
| DE1693027C3 (de) | Verfahren zur Herstellung von ε-Caprolacton oder von Methyl-ε-caprolactonen | |
| EP0360094A2 (de) | Verfahren zum Herstellen von Homopolymerisaten oder Copolymerisaten des Propylens | |
| DE2122750A1 (enrdf_load_stackoverflow) | ||
| DE69516098T2 (de) | Verfahren zur Herstellung von Isopropylalkohol durch Hydratisierung von Propylen | |
| DE2945075A1 (de) | Verfahren zur behandlung einer c tief 4 -kohlenwasserstoff-fraktion zur gewinnung von butadien | |
| DE2052782B2 (de) | Verfahren zur Herstellung von olefinisch ungesättigten Verbindungen durch Dehydratisierung von Alkoholen | |
| DE2136744C3 (de) | Verfahren zur Herstellung von Cyclohexylhydroperoxid enthaltenden Oxidationsprodukten | |
| DE1294013B (enrdf_load_stackoverflow) | ||
| EP0934238A1 (de) | Verfahren zur herstellung von oxidationsprodukten des cyclohexans im gegenstrom | |
| DE69020572T2 (de) | Verfahren zur entfernung von chloropren aus 1,2-dichlorethan. | |
| WO2004054998A1 (de) | Verfahren zur herstellung von trioxan | |
| DE882402C (de) | Reaktionsgefaess und Verfahren zur Durchfuehrung chemischer Reaktionen | |
| DE935844C (de) | Verfahren zur Herstellung von Propionaldehyd und Propanol | |
| DE1929076A1 (de) | Verfahren zur Reinigung ungesaettigter Kohlenwasserstoffe | |
| DE907889C (de) | Verfahren zur Durchfuehrung der Oxo-Synthese mit Mischungen von Olefinen | |
| DE2359286A1 (de) | Verfahren zur katalytischen herstellung von alkancarbonsaeurealkenylestern | |
| DE2042378C3 (enrdf_load_stackoverflow) | ||
| DE857373C (de) | Aufarbeitungsverfahren fuer waessrige Loesungen von Acrylnitril | |
| DE2144475A1 (de) | Verfahren zur kontinuierlichen herstellung von 3,4-dichlorbuten-1 | |
| DE1568177C3 (de) | Verfahren zur kontinuierlichen Herstellung von alpha-Acetyl-alphachlor-gamma-butyrolacton | |
| DE932368C (de) | Verfahren zur Herstellung von Carbonsaeuren | |
| DE1079021B (de) | Verfahren zur Herstellung von AEthylchlorid aus AEthylen und AEthan | |
| AT213391B (de) | Verfahren zur Herstellung von Carbonsäuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |