CA1057314A - Oxidation of diethylbenzenes - Google Patents
Oxidation of diethylbenzenesInfo
- Publication number
- CA1057314A CA1057314A CA233,213A CA233213A CA1057314A CA 1057314 A CA1057314 A CA 1057314A CA 233213 A CA233213 A CA 233213A CA 1057314 A CA1057314 A CA 1057314A
- Authority
- CA
- Canada
- Prior art keywords
- diethylbenzene
- feedstock
- oxidation
- reaction
- metal oxide
- 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.)
- Expired
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 49
- 230000003647 oxidation Effects 0.000 title claims abstract description 29
- 150000005195 diethylbenzenes Chemical class 0.000 title abstract description 12
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims abstract description 104
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000007789 gas Substances 0.000 claims abstract description 23
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims abstract description 18
- GAEYNZPUAJMOJP-UHFFFAOYSA-N 1,2-diethylbenzene hydrogen peroxide Chemical compound OO.CCC1=CC=CC=C1CC GAEYNZPUAJMOJP-UHFFFAOYSA-N 0.000 claims abstract description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 11
- 238000000746 purification Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 29
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000012535 impurity Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 10
- 239000000395 magnesium oxide Substances 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 238000002203 pretreatment Methods 0.000 claims description 6
- 230000001627 detrimental effect Effects 0.000 claims description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002432 hydroperoxides Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SMILELQFOWXKKC-UHFFFAOYSA-N OO.CCCC(=O)C1=CC=CC=C1 Chemical compound OO.CCCC(=O)C1=CC=CC=C1 SMILELQFOWXKKC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- -1 perbenzoates Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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 |
|---|---|---|---|
| US05/496,644 US4169210A (en) | 1974-08-12 | 1974-08-12 | Oxidation of diethylbenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057314A true CA1057314A (en) | 1979-06-26 |
Family
ID=23973539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,213A Expired CA1057314A (en) | 1974-08-12 | 1975-08-11 | Oxidation of diethylbenzenes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4169210A (https=) |
| JP (1) | JPS5141334A (https=) |
| BE (1) | BE832358A (https=) |
| CA (1) | CA1057314A (https=) |
| DE (1) | DE2535835A1 (https=) |
| FR (1) | FR2281926A1 (https=) |
| GB (1) | GB1479115A (https=) |
| IT (1) | IT1040317B (https=) |
| NL (1) | NL7508549A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5813781A (ja) * | 1981-07-14 | 1983-01-26 | 東レ株式会社 | 耐擦過性にすぐれた炭素繊維 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2621213A (en) * | 1949-07-19 | 1952-12-09 | Allied Chem & Dye Corp | Pretreatment of aralkyl hydrocarbons with alkali metal hydroxide |
| US2632774A (en) * | 1949-11-18 | 1953-03-24 | Hercules Powder Co Ltd | Oxioation of aromatic hydrocarbons |
| US2535344A (en) * | 1949-11-26 | 1950-12-26 | Hercules Powder Co Ltd | Flotation of minerals with hydroperoxide frothers |
| US2661375A (en) * | 1950-02-07 | 1953-12-01 | Hercules Powder Co Ltd | Production of phenols and acyclic aldehydes |
| US2633476A (en) * | 1952-03-04 | 1953-03-31 | Shell Dev | Production of aromatic hydroperoxides |
| GB758934A (en) * | 1953-10-12 | 1956-10-10 | Ici Ltd | Improvements in and relating to the oxidation of aromatic hydrocarbons |
| US2883427A (en) * | 1954-09-22 | 1959-04-21 | Monsanto Chemicals | Manufacture of diphenylmethyl hydroperoxide |
| US2813907A (en) * | 1954-10-06 | 1957-11-19 | Shell Dev | Production of aralkyl hydroperoxides |
| FR1392364A (fr) * | 1963-05-09 | 1965-03-12 | Universal Oil Prod Co | Procédé de préparation d'hydroperoxydes d'hydrocarbures aromatiques alcoyl substitués |
-
1974
- 1974-08-12 US US05/496,644 patent/US4169210A/en not_active Expired - Lifetime
-
1975
- 1975-07-17 NL NL7508549A patent/NL7508549A/xx unknown
- 1975-08-01 IT IT26026/75A patent/IT1040317B/it active
- 1975-08-05 JP JP50094803A patent/JPS5141334A/ja active Pending
- 1975-08-06 GB GB32891/75A patent/GB1479115A/en not_active Expired
- 1975-08-11 FR FR7524917A patent/FR2281926A1/fr active Granted
- 1975-08-11 CA CA233,213A patent/CA1057314A/en not_active Expired
- 1975-08-12 DE DE19752535835 patent/DE2535835A1/de not_active Withdrawn
- 1975-08-12 BE BE159139A patent/BE832358A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1479115A (en) | 1977-07-06 |
| DE2535835A1 (de) | 1976-02-26 |
| US4169210A (en) | 1979-09-25 |
| BE832358A (fr) | 1975-12-01 |
| JPS5141334A (en) | 1976-04-07 |
| NL7508549A (nl) | 1976-02-16 |
| FR2281926A1 (fr) | 1976-03-12 |
| FR2281926B1 (https=) | 1979-05-18 |
| IT1040317B (it) | 1979-12-20 |
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