NO128324B - - Google Patents
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- Publication number
- NO128324B NO128324B NO00166200A NO16620066A NO128324B NO 128324 B NO128324 B NO 128324B NO 00166200 A NO00166200 A NO 00166200A NO 16620066 A NO16620066 A NO 16620066A NO 128324 B NO128324 B NO 128324B
- Authority
- NO
- Norway
- Prior art keywords
- ethylbenzene
- reaction
- oxidation
- temperature
- hydroperoxide
- Prior art date
Links
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 24
- 230000003647 oxidation Effects 0.000 claims description 23
- 230000035484 reaction time Effects 0.000 claims description 12
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000006227 byproduct Substances 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- -1 chlorohydrin compound Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51782165A | 1965-12-30 | 1965-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128324B true NO128324B (fr) | 1973-10-29 |
Family
ID=24061367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00166200A NO128324B (fr) | 1965-12-30 | 1966-12-29 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3459810A (fr) |
| BE (1) | BE691683A (fr) |
| CH (1) | CH470339A (fr) |
| DE (1) | DE1568808A1 (fr) |
| ES (1) | ES335098A1 (fr) |
| FR (1) | FR1510252A (fr) |
| GB (1) | GB1128150A (fr) |
| IL (1) | IL27188A (fr) |
| LU (1) | LU52693A1 (fr) |
| NL (1) | NL6617603A (fr) |
| NO (1) | NO128324B (fr) |
| SE (1) | SE330168B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846499A (en) * | 1970-10-22 | 1974-11-05 | Texaco Inc | Manufacture of hydrocarbyl hydroperoxide |
| US4066706A (en) * | 1975-04-21 | 1978-01-03 | Halcon International, Inc. | Preparation of ethylbenzene hydroperoxide |
| JPS6017783B2 (ja) * | 1977-10-31 | 1985-05-07 | 三井化学株式会社 | ｍ−ジイソプロピルベンゼンの酸化方法 |
| US4262143A (en) * | 1979-02-16 | 1981-04-14 | Halcon International, Inc. | Preparation of hydroperoxides |
| US5446227A (en) * | 1993-09-07 | 1995-08-29 | Phillips Petroleum Company | Co-production of an alkenyl aromatic compound or precursor thereof and an oxygenated sulfur-containing compound |
| JP3301245B2 (ja) * | 1994-03-24 | 2002-07-15 | 住友化学工業株式会社 | プロピレンオキシドの回収方法 |
| DE10139212A1 (de) * | 2001-08-09 | 2003-02-27 | Creavis Tech & Innovation Gmbh | Herstellung von Peroxiden des Ethylbenzols und deren Verwendung |
| US7901128B2 (en) * | 2004-07-20 | 2011-03-08 | Dow Global Technologies Llc | Tapered aperture multi-tee mixer |
| ES2261080B1 (es) * | 2005-04-19 | 2007-12-16 | Universidad Politecnica De Valencia | Procedimiento y catalizadores para la expoxidacion de compuestos olefinicos en presencia de oxigeno. |
| WO2008058925A1 (fr) * | 2006-11-13 | 2008-05-22 | Shell Internationale Research Maatschappij B.V. | Procédé pour l'oxydation en phase liquide de l'éthylbenzène en hydroperoxyde d'éthylbenzène |
| CN106554298B (zh) * | 2015-09-28 | 2019-04-23 | 万华化学集团股份有限公司 | 一种乙苯氧化制备乙苯氢过氧化物的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2749368A (en) * | 1952-09-15 | 1956-06-05 | Shell Dev | Production of aralkyl hydroperoxides |
| US2867666A (en) * | 1954-09-22 | 1959-01-06 | Monsanto Chemicals | Production of alpha-methylbenzyl hydroperoxide |
-
1965
- 1965-12-30 US US517821A patent/US3459810A/en not_active Expired - Lifetime
-
1966
- 1966-12-14 NL NL6617603A patent/NL6617603A/xx unknown
- 1966-12-21 GB GB57291/66A patent/GB1128150A/en not_active Expired
- 1966-12-23 BE BE691683D patent/BE691683A/fr not_active IP Right Cessation
- 1966-12-28 LU LU52693D patent/LU52693A1/xx unknown
- 1966-12-29 CH CH1870966A patent/CH470339A/fr not_active IP Right Cessation
- 1966-12-29 FR FR89285A patent/FR1510252A/fr not_active Expired
- 1966-12-29 IL IL27188A patent/IL27188A/en unknown
- 1966-12-29 NO NO00166200A patent/NO128324B/no unknown
- 1966-12-30 DE DE19661568808 patent/DE1568808A1/de not_active Ceased
- 1966-12-30 ES ES0335098A patent/ES335098A1/es not_active Expired
- 1966-12-30 SE SE17940/66A patent/SE330168B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE330168B (fr) | 1970-11-09 |
| DE1568808A1 (de) | 1970-04-16 |
| BE691683A (fr) | 1967-06-23 |
| LU52693A1 (fr) | 1968-08-05 |
| CH470339A (fr) | 1969-03-31 |
| GB1128150A (en) | 1968-09-25 |
| NL6617603A (fr) | 1967-07-03 |
| IL27188A (en) | 1970-09-17 |
| FR1510252A (fr) | 1968-01-19 |
| ES335098A1 (es) | 1967-11-16 |
| US3459810A (en) | 1969-08-05 |
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