DE1012913B - Verfahren zur Herstellung von Hydroperoxyden substituierter aromatischer Kohlenwasserstoffe - Google Patents
Verfahren zur Herstellung von Hydroperoxyden substituierter aromatischer KohlenwasserstoffeInfo
- Publication number
- DE1012913B DE1012913B DES32959A DES0032959A DE1012913B DE 1012913 B DE1012913 B DE 1012913B DE S32959 A DES32959 A DE S32959A DE S0032959 A DES0032959 A DE S0032959A DE 1012913 B DE1012913 B DE 1012913B
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- aromatic hydrocarbons
- hydroperoxides
- keto acid
- substituted aromatic
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000002432 hydroperoxides Chemical group 0.000 title claims description 3
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 11
- -1 ß-keto acid ester Chemical class 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- 230000006698 induction Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- OUGLPIHDPBRSID-UHFFFAOYSA-N 2-ethyl-3-oxobutanedioic acid Chemical compound CCC(C(O)=O)C(=O)C(O)=O OUGLPIHDPBRSID-UHFFFAOYSA-N 0.000 description 1
- XVUBJBPHJUNOTD-UHFFFAOYSA-N 2-nitro-3-oxo-3-phenylpropanoic acid Chemical compound OC(=O)C([N+]([O-])=O)C(=O)C1=CC=CC=C1 XVUBJBPHJUNOTD-UHFFFAOYSA-N 0.000 description 1
- RTPQHRPDDDCSGE-UHFFFAOYSA-N 3,5-dioxo-5-phenylpentanoic acid Chemical compound OC(=O)CC(=O)CC(=O)C1=CC=CC=C1 RTPQHRPDDDCSGE-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- RRJVSWHPJLGNPA-UHFFFAOYSA-N 4-ethoxy-2,4-dioxobutanoic acid Chemical compound CCOC(=O)CC(=O)C(O)=O RRJVSWHPJLGNPA-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- JHCGIFHFABXVNQ-UHFFFAOYSA-N ethyl 3,5-dioxo-5-phenylpentanoate Chemical compound CCOC(=O)CC(=O)CC(=O)C1=CC=CC=C1 JHCGIFHFABXVNQ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
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 |
|---|---|---|---|
| FR1012913X | 1952-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1012913B true DE1012913B (de) | 1957-08-01 |
Family
ID=9571234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES32959A Pending DE1012913B (de) | 1952-04-11 | 1953-04-07 | Verfahren zur Herstellung von Hydroperoxyden substituierter aromatischer Kohlenwasserstoffe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2674629A (en, 2012) |
| BE (1) | BE518624A (en, 2012) |
| CH (1) | CH307323A (en, 2012) |
| DE (1) | DE1012913B (en, 2012) |
| FR (1) | FR1053743A (en, 2012) |
| GB (1) | GB736715A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131674B (de) * | 1960-05-10 | 1962-06-20 | Phenolchemie Ges Mit Beschraen | Verfahren zur Herstellung von Aralkylmonohydroperoxyden |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE535707A (en, 2012) * | 1954-02-17 | |||
| US2792426A (en) * | 1954-10-14 | 1957-05-14 | Monsanto Chemicals | Production of hydroperoxides using alpha-aryl ketones as oxidation initiators |
| US2792425A (en) * | 1954-10-14 | 1957-05-14 | Monsanto Chemicals | Production of hydroperoxides using malonic esters as oxidation initiators |
| US2792424A (en) * | 1954-10-14 | 1957-05-14 | Monsanto Chemicals | Production of hydroperoxides using certain beta diketones as oxidation initiators |
| US2861107A (en) * | 1955-08-22 | 1958-11-18 | Edogawa Kagaku Kogyo Kabushiki | Process for the production of cumene hydroperoxide |
| DE1033658B (de) * | 1955-10-26 | 1958-07-10 | Montedison Spa | Verfahren zur Herstellung von Phenylcyclohexylhydroperoxyd |
| DE1059903B (de) * | 1956-05-23 | 1959-06-25 | Montedison Spa | Verfahren zur Herstellung von Phenylcyclohexylhydroperoxyd |
| US4602118A (en) * | 1984-11-09 | 1986-07-22 | Exxon Research And Engineering Co. | Liquid phase oxidation of organic compounds to their hydroperoxides |
| CN109180548A (zh) * | 2018-09-11 | 2019-01-11 | 中国海洋石油集团有限公司 | 提高乙苯氢过氧化物稳定性的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB610293A (en) * | 1946-04-08 | 1948-10-13 | Distillers Co Yeast Ltd | Improvements in or relating to the manufacture of alkyl benzene peroxides |
-
0
- BE BE518624D patent/BE518624A/xx unknown
-
1952
- 1952-04-11 FR FR1053743D patent/FR1053743A/fr not_active Expired
-
1953
- 1953-04-01 GB GB9098/53A patent/GB736715A/en not_active Expired
- 1953-04-03 US US346806A patent/US2674629A/en not_active Expired - Lifetime
- 1953-04-07 DE DES32959A patent/DE1012913B/de active Pending
- 1953-04-10 CH CH307323D patent/CH307323A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB610293A (en) * | 1946-04-08 | 1948-10-13 | Distillers Co Yeast Ltd | Improvements in or relating to the manufacture of alkyl benzene peroxides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131674B (de) * | 1960-05-10 | 1962-06-20 | Phenolchemie Ges Mit Beschraen | Verfahren zur Herstellung von Aralkylmonohydroperoxyden |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1053743A (fr) | 1954-02-04 |
| US2674629A (en) | 1954-04-06 |
| GB736715A (en) | 1955-09-14 |
| CH307323A (fr) | 1955-05-31 |
| BE518624A (en, 2012) |
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