CA1071656A - Preparation of ethylbenzene hydroperoxide - Google Patents
Preparation of ethylbenzene hydroperoxideInfo
- Publication number
- CA1071656A CA1071656A CA000250488A CA250488A CA1071656A CA 1071656 A CA1071656 A CA 1071656A CA 000250488 A CA000250488 A CA 000250488A CA 250488 A CA250488 A CA 250488A CA 1071656 A CA1071656 A CA 1071656A
- Authority
- CA
- Canada
- Prior art keywords
- zone
- ethylbenzene
- oxidation
- reaction zone
- liquid
- 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
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 166
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 90
- 230000003647 oxidation Effects 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 22
- 239000011261 inert gas Substances 0.000 claims abstract description 20
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 239000007788 liquid Substances 0.000 claims description 42
- 239000007789 gas Substances 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 8
- 238000011144 upstream manufacturing Methods 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 5
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 229940058172 ethylbenzene Drugs 0.000 description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
- B01J10/002—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor carried out in foam, aerosol or bubbles
-
- 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
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/0004—Processes in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00105—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling
- B01J2219/00108—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00761—Details of the reactor
- B01J2219/00763—Baffles
- B01J2219/00765—Baffles attached to the reactor wall
- B01J2219/00768—Baffles attached to the reactor wall vertical
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/18—Details relating to the spatial orientation of the reactor
- B01J2219/182—Details relating to the spatial orientation of the reactor horizontal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/19—Details relating to the geometry of the reactor
- B01J2219/194—Details relating to the geometry of the reactor round
- B01J2219/1941—Details relating to the geometry of the reactor round circular or disk-shaped
- B01J2219/1943—Details relating to the geometry of the reactor round circular or disk-shaped cylindrical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/569,734 US4066706A (en) | 1975-04-21 | 1975-04-21 | Preparation of ethylbenzene hydroperoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071656A true CA1071656A (en) | 1980-02-12 |
Family
ID=24276630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000250488A Expired CA1071656A (en) | 1975-04-21 | 1976-04-20 | Preparation of ethylbenzene hydroperoxide |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4066706A (enExample) |
| JP (1) | JPS51128931A (enExample) |
| AU (1) | AU500738B2 (enExample) |
| BE (1) | BE840918A (enExample) |
| BR (1) | BR7602423A (enExample) |
| CA (1) | CA1071656A (enExample) |
| DE (1) | DE2617432C3 (enExample) |
| ES (1) | ES447195A1 (enExample) |
| FR (1) | FR2308619A1 (enExample) |
| GB (1) | GB1502045A (enExample) |
| IT (1) | IT1058164B (enExample) |
| NL (1) | NL172237C (enExample) |
| SU (1) | SU988189A3 (enExample) |
| ZA (1) | ZA761760B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4408081A (en) * | 1981-10-05 | 1983-10-04 | Shell Oil Company | Process for oxidation of isobutane |
| US4556748A (en) * | 1983-10-31 | 1985-12-03 | The Dow Chemical Company | Process for producing alkylene glycols |
| US4950794A (en) * | 1989-05-24 | 1990-08-21 | Arco Chemical Technology, Inc. | Ethylbenzene oxidation |
| US5210354A (en) * | 1992-05-08 | 1993-05-11 | Arco Chemical Technology, L.P. | Propylene oxide-styrene monomer process |
| US5276235A (en) * | 1993-02-19 | 1994-01-04 | Arco Chemical Technology, L.P. | Residual stream upgrading in a propylene oxide-styrene monomer process |
| US5675055A (en) * | 1995-10-04 | 1997-10-07 | Arco Chemical Technology, L.P. | Acidification/extraction treatment of waste caustic stream |
| US5883268A (en) * | 1997-10-23 | 1999-03-16 | Arco Chemical Technology, L.P. | Process stream purification |
| US6512129B1 (en) | 2002-01-23 | 2003-01-28 | Arco Chemical Technology, L.P. | Epoxidation process |
| US6755979B2 (en) * | 2002-08-15 | 2004-06-29 | Arco Chemical Technology, L.P. | Peroxide impurities removal |
| ES2339111T3 (es) * | 2003-09-24 | 2010-05-17 | Repsol Quimica S.A. | Procedimiento para la preparacion de hidroperoxidos. |
| JP4743442B2 (ja) * | 2004-07-20 | 2011-08-10 | ダウ グローバル テクノロジーズ エルエルシー | テーパー状開口付きマルチｔ字ミキサ |
| BRPI0514717A (pt) * | 2004-09-01 | 2008-06-24 | Shell Int Research | vaso reator substancialmente horizontal, reator, e, processos de contatar um reagente lìquido com um reagente gasoso e de fabricar um hidroperóxido orgánico |
| DE602006012535D1 (de) * | 2005-10-21 | 2010-04-08 | Glaxo Group Ltd | Peri-kondensierte tricyclische verbindungen verwendbar als antibakterielle mittel |
| CN101535248B (zh) * | 2006-11-13 | 2012-08-08 | 国际壳牌研究有限公司 | 将乙苯液相氧化成乙苯氢过氧化物的方法 |
| US8142661B2 (en) * | 2008-09-29 | 2012-03-27 | Lyondell Chemical Technology, L.P. | Residual stream upgrading in a propylene oxide-styrene monomer process |
| NL2007874C2 (en) | 2011-11-25 | 2013-05-28 | Progression Industry B V | The application of chemical compounds presents a styrene production process in a fuel. |
| 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 |
| RU2633362C2 (ru) * | 2016-01-12 | 2017-10-12 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ получения гидропероксида этилбензола |
| MX378115B (es) | 2017-02-03 | 2025-03-10 | Lyondell Chemical Tech Lp | Mejora de la corriente de residuos en un proceso de coproducción de óxido de propileno/estireno. |
| SG11201909635WA (en) | 2017-05-01 | 2019-11-28 | Lyondell Chemical Technology L P | By-product stream upgrading in a propylene oxide/styrene coproduction process |
| EP3412635B1 (en) | 2017-06-08 | 2021-04-14 | Lyondell Chemie Nederland B.V. | Wastewater treatment method |
| CN107930555B (zh) * | 2017-11-30 | 2021-04-20 | 万华化学集团股份有限公司 | 制备乙苯氢过氧化物的多级卧式搅拌气升式反应器及应用 |
| JP7194272B2 (ja) * | 2018-12-26 | 2022-12-21 | 万華化学集団股▲分▼有限公司 | 有機物を酸化するための装置及び方法 |
| CN110743486A (zh) * | 2019-12-06 | 2020-02-04 | 东华工程科技股份有限公司 | 用于草酰胺的合成反应器 |
| CN111606835A (zh) * | 2020-06-05 | 2020-09-01 | 常州瑞华化工工程技术股份有限公司 | 一种乙苯氧化制备乙苯过氧化氢的方法 |
| US20230339832A1 (en) | 2022-04-21 | 2023-10-26 | Lyondell Chemical Technology, L.P. | Use of carbon dioxide to improve caustic washing of alkylene oxide / alkenyl benzene monomer streams |
| WO2025165853A1 (en) | 2024-01-30 | 2025-08-07 | Lyondell Chemical Technology, L.P. | Process for production of propylene oxide and styrene monomer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2637772A (en) * | 1948-07-07 | 1953-05-05 | Rca Corp | Keyed automatic gain control |
| US3459810A (en) * | 1965-12-30 | 1969-08-05 | Halcon International Inc | Process for the preparation of ethylbenzene hydroperoxide |
| US3351635A (en) * | 1966-03-14 | 1967-11-07 | Halcon International Inc | Epoxidation process |
| FR1491518A (fr) * | 1966-06-30 | 1967-08-11 | Rhone Poulenc Sa | Préparation d'hydroperoxydes |
| JPS4945383A (enExample) * | 1972-09-09 | 1974-04-30 |
-
1975
- 1975-04-21 US US05/569,734 patent/US4066706A/en not_active Expired - Lifetime
-
1976
- 1976-03-23 ZA ZA761760A patent/ZA761760B/xx unknown
- 1976-04-12 NL NLAANVRAGE7603846,A patent/NL172237C/xx not_active IP Right Cessation
- 1976-04-20 BE BE166296A patent/BE840918A/xx not_active IP Right Cessation
- 1976-04-20 BR BR2423/76A patent/BR7602423A/pt unknown
- 1976-04-20 FR FR7611529A patent/FR2308619A1/fr active Granted
- 1976-04-20 SU SU762346055A patent/SU988189A3/ru active
- 1976-04-20 CA CA000250488A patent/CA1071656A/en not_active Expired
- 1976-04-20 IT IT49090/76A patent/IT1058164B/it active
- 1976-04-21 JP JP51046068A patent/JPS51128931A/ja active Granted
- 1976-04-21 DE DE2617432A patent/DE2617432C3/de not_active Expired
- 1976-04-21 GB GB16164/75A patent/GB1502045A/en not_active Expired
- 1976-04-21 ES ES447195A patent/ES447195A1/es not_active Expired
- 1976-09-03 AU AU12981/76A patent/AU500738B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51128931A (en) | 1976-11-10 |
| FR2308619A1 (fr) | 1976-11-19 |
| AU1298176A (en) | 1977-10-20 |
| NL7603846A (nl) | 1976-10-25 |
| SU988189A3 (ru) | 1983-01-07 |
| ZA761760B (en) | 1977-10-26 |
| JPS564549B2 (enExample) | 1981-01-30 |
| NL172237B (nl) | 1983-03-01 |
| IT1058164B (it) | 1982-04-10 |
| US4066706A (en) | 1978-01-03 |
| BE840918A (fr) | 1976-10-20 |
| GB1502045A (en) | 1978-02-22 |
| DE2617432A1 (de) | 1976-11-04 |
| AU500738B2 (en) | 1979-05-31 |
| DE2617432B2 (de) | 1979-02-15 |
| NL172237C (nl) | 1983-08-01 |
| DE2617432C3 (de) | 1979-10-31 |
| ES447195A1 (es) | 1977-07-01 |
| BR7602423A (pt) | 1976-10-19 |
| FR2308619B1 (enExample) | 1979-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |