TWI343910B - - Google Patents
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- Publication number
- TWI343910B TWI343910B TW094106461A TW94106461A TWI343910B TW I343910 B TWI343910 B TW I343910B TW 094106461 A TW094106461 A TW 094106461A TW 94106461 A TW94106461 A TW 94106461A TW I343910 B TWI343910 B TW I343910B
- Authority
- TW
- Taiwan
- Prior art keywords
- reactor
- oxygen
- gas
- cumene hydroperoxide
- liquid phase
- Prior art date
Links
- 239000007789 gas Substances 0.000 claims description 107
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 103
- 239000001301 oxygen Substances 0.000 claims description 103
- 229910052760 oxygen Inorganic materials 0.000 claims description 103
- 238000004519 manufacturing process Methods 0.000 claims description 50
- 239000007791 liquid phase Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 41
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 37
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 29
- 238000007254 oxidation reaction Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 17
- 239000011148 porous material Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000012295 chemical reaction liquid Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004880 explosion Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- -1 dimethyl phenyl Chemical group 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 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
- 230000000704 physical effect Effects 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 description 1
- LCKPEFUXKRSTMA-UHFFFAOYSA-N 6-propan-2-yl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C(C)C)C1O2 LCKPEFUXKRSTMA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004476 mid-IR spectroscopy Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- 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
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
-
- 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
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
- B01J4/002—Nozzle-type elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004060904 | 2004-03-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200602300A TW200602300A (en) | 2006-01-16 |
| TWI343910B true TWI343910B (enExample) | 2011-06-21 |
Family
ID=34918034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094106461A TW200602300A (en) | 2004-03-04 | 2005-03-03 | Process for production of cumene hydroperoxide |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7439404B2 (enExample) |
| EP (1) | EP1721895A4 (enExample) |
| KR (1) | KR101168875B1 (enExample) |
| CN (1) | CN1926101B (enExample) |
| TW (1) | TW200602300A (enExample) |
| WO (1) | WO2005085191A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1932583A1 (en) * | 2006-11-28 | 2008-06-18 | Shell Internationale Researchmaatschappij B.V. | Reactor vessel |
| US20090005606A1 (en) * | 2007-06-27 | 2009-01-01 | H R D Corporation | High shear process for the production of cumene hydroperoxide |
| WO2011053818A2 (en) * | 2009-10-30 | 2011-05-05 | Illa International, Llc | Non-barbotage method for oxidation of hydrocarbons by forming and utilizing liquid phase thin film |
| IT1396221B1 (it) * | 2009-11-09 | 2012-11-16 | Polimeri Europa Spa | Procedimento per la preparazione di fenolo da cumene. |
| WO2012036825A1 (en) * | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Oxidation of cyclohexylbenzene |
| RU2566504C1 (ru) * | 2014-08-08 | 2015-10-27 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" | Способ окисления алкилароматических углеводородов и реактор для его осуществления |
| CN104447629B (zh) * | 2014-12-01 | 2017-01-04 | 中石化上海工程有限公司 | 环氧丙烷装置氧化单元副产蒸汽的方法 |
| CN104876845B (zh) * | 2015-05-28 | 2017-01-04 | 南京红宝丽股份有限公司 | 一种过氧化羟基异丙苯的制备方法 |
| 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 |
| CN112830865A (zh) * | 2019-11-25 | 2021-05-25 | 南京延长反应技术研究院有限公司 | 一种基于微界面强化异丙苯制备苯酚的系统及工艺 |
| CN117884055A (zh) * | 2022-10-08 | 2024-04-16 | 中国石油化工股份有限公司 | 一种过氧化氢异丙苯的连续合成系统和方法 |
| CN119707768B (zh) * | 2024-12-30 | 2025-07-01 | 常州瑞华化工工程技术股份有限公司 | 一种异丁烷氧化方法及系统 |
| CN119684236B (zh) * | 2024-12-30 | 2025-07-04 | 常州瑞华化工工程技术股份有限公司 | 一种异丙苯法低能耗生产环氧丙烷的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619510A (en) * | 1948-05-06 | 1952-11-25 | Hercules Powder Co Ltd | Manufacture of isopropyl benzene hydroperoxide |
| US3907901A (en) * | 1969-07-14 | 1975-09-23 | Allied Chem | Continuous process for preparing cumene hydroperoxide |
| FR2708603B1 (fr) | 1993-08-06 | 1995-10-27 | Rhone Poulenc Chimie | Procédé de préparation d'hydroperoxyde de cumène. |
| US6043399A (en) | 1994-08-08 | 2000-03-28 | Rhodia Chimie | Process for the preparation of cumene hydroperoxide |
| US5767322A (en) | 1996-06-27 | 1998-06-16 | General Electric Company | Cumene oxidation process |
| ID19133A (id) * | 1996-12-12 | 1998-06-18 | Praxair Technology Inc | Pengisian oksigen langsung kedalam reaktor-reaktor ruang gelembung |
| JP2000053641A (ja) | 1998-08-10 | 2000-02-22 | Mitsubishi Chemicals Corp | 有機ハイドロパーオキサイド及びフェノールの製造方法 |
| JP2000063352A (ja) | 1998-08-12 | 2000-02-29 | Mitsui Chemicals Inc | 芳香族アルキルヒドロペルオキシドの製造方法 |
| JP2003231674A (ja) | 2002-02-07 | 2003-08-19 | Sumitomo Chem Co Ltd | クメンの酸化方法 |
| JP2003327576A (ja) | 2002-03-06 | 2003-11-19 | Sumitomo Chem Co Ltd | クメンハイドロパーオキサイドを含む溶液の加熱システム |
| JP3954460B2 (ja) | 2002-07-24 | 2007-08-08 | 株式会社ノーリツ | 浴室暖房装置 |
-
2005
- 2005-03-03 WO PCT/JP2005/003599 patent/WO2005085191A1/ja not_active Ceased
- 2005-03-03 KR KR1020067017680A patent/KR101168875B1/ko not_active Expired - Lifetime
- 2005-03-03 EP EP05719903A patent/EP1721895A4/en not_active Withdrawn
- 2005-03-03 CN CN2005800063989A patent/CN1926101B/zh not_active Expired - Lifetime
- 2005-03-03 US US10/591,439 patent/US7439404B2/en not_active Expired - Lifetime
- 2005-03-03 TW TW094106461A patent/TW200602300A/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1926101B (zh) | 2010-11-24 |
| KR20070001985A (ko) | 2007-01-04 |
| CN1926101A (zh) | 2007-03-07 |
| WO2005085191A1 (ja) | 2005-09-15 |
| TW200602300A (en) | 2006-01-16 |
| KR101168875B1 (ko) | 2012-07-30 |
| US7439404B2 (en) | 2008-10-21 |
| EP1721895A1 (en) | 2006-11-15 |
| EP1721895A4 (en) | 2008-02-27 |
| US20070260093A1 (en) | 2007-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |