WO2003068763A1 - Procede de recuperation d'oxyde de propylene - Google Patents
Procede de recuperation d'oxyde de propylene Download PDFInfo
- Publication number
- WO2003068763A1 WO2003068763A1 PCT/JP2003/001421 JP0301421W WO03068763A1 WO 2003068763 A1 WO2003068763 A1 WO 2003068763A1 JP 0301421 W JP0301421 W JP 0301421W WO 03068763 A1 WO03068763 A1 WO 03068763A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- propylene oxide
- propylene
- cumene
- reaction
- recovering
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Definitions
- the present invention relates to a method for recovering propylene oxide. More specifically, the present invention provides a method for recovering propylene oxide from a reaction solution in which propylene oxide is produced by reacting cumene hydroperoxide with propylene in a high yield, and further comprising a step of purifying the propylene oxide.
- the present invention relates to a method for recovering propylene oxide, which is capable of minimizing the problem of yield loss and corrosion, and which is particularly advantageous from an industrial viewpoint. Background art
- a method of obtaining propylene oxide by oxidizing propylene using cumene hydroperoxide as an oxygen carrier is known in WO 01/05778 and the like. Since it is produced, it is hydrogenated and converted to cumene, and then oxidized to return to cumene hydroperoxide, which can be used repeatedly. Disclosure of the invention
- An object of the present invention is to recover propylene oxide in a high yield from a reaction solution containing propylene oxide obtained by reacting cumene hydroperoxide with propylene, and further comprising a step of purifying the propylene oxide. It is an object of the present invention to provide a method for recovering propylene oxide, which is capable of minimizing problems such as a decrease in yield and corrosion in the propylene oxide, and which is extremely advantageous from an industrial point of view.
- the present invention is a method for distilling and separating propylene oxide from a mixed solution containing propylene oxide, cumene and cumyl alcohol using a distillation column, wherein the column bottom temperature of the distillation column is 190 or less. It relates to a method for recovering a certain propylene oxide.
- a mixed solution containing propylene oxide, cumene and cumyl alcohol can be obtained by subjecting cumene hydroperoxide and propylene to an epoxidation reaction in the presence of a catalyst.
- the epoxidation reaction is preferably carried out in the presence of a catalyst comprising a titanium-containing silicon oxide from the viewpoint of obtaining propylene oxide with high yield and high selectivity.
- These catalysts are preferably so-called titanium-silicone catalysts containing titanium chemically bonded to silicon oxide.
- a titanium compound supported on a silica carrier, a compound compounded with silicon oxide by a coprecipitation method or a sol-gel method, or a zeolite compound containing titanium can be used.
- Cumene hydroperoxide used as a raw material for the epoxidation reaction is generally obtained by autoxidation of cumene with an oxygen-containing gas such as air or oxygen-enriched air, and is a diluted or concentrated purified or unpurified product. May be.
- the solvent may be composed of a substance existing in the cumene hydroperoxide solution used, but it is particularly preferable to use cumene as a solvent without adding a solvent from an industrial viewpoint.
- the epoxidation reaction temperature is generally 0 to 200, but a temperature of 25 to 200 is preferred.
- the pressure is usually 100 to 2000 kPa, but a pressure of 100 to 1000 kPa is preferable in consideration of the reaction temperature and economy.
- the epoxidation reaction can be advantageously carried out using a catalyst in the form of a slurry or fixed bed, but for large-scale industrial operations, a fixed bed is preferred.
- the amount of propylene used in the epoxidation reaction is usually 1 to 20 times, preferably 5 to 20 times the molar amount of the fresh cumenehydride peroxide used in the epoxidation reaction. It is.
- the use of excess propylene relative to fresh cumene hydroperoxide is effective in maintaining a high level of propylene oxide formed.
- Excess propylene remaining after the epoxy reaction is usually recovered by distillation.
- propylene oxide is recovered by distillation.
- the recovery of propylene oxide may be carried out in any step after the epoxidation reaction, but considering the energy required for distillation, propylene oxide, cumene and cumyl after recovering unreacted propylene are considered. It is preferable to use a mixed solution containing alcohol.
- Distillation conditions vary depending on the temperature and composition of the reaction liquid supplied to the distillation process, but the pressure is usually 0 to 1 MPa in gauge pressure, preferably 0 to 0.1 MPa, and the top of the column.
- the temperature can be increased from 0 to 100 ° C.
- Examples of the distillation method include a packed tower method using a packing material and a tray column method using a perforated plate, etc. From the viewpoint, it is preferable to use a packed tower system.
- the bottom temperature of the distillation column at the time of recovering propylene oxide is 190 or less in order to achieve the object of the present invention.
- the tower bottom temperature is preferably about 100.
- Example 2 As a raw material, 40 g of a mixed solution of 5% by weight of cumyl alcohol and 95% by weight of cumene was charged into a autoclave, and heated and stirred at 136 for 60 minutes. Dehydration of cumyl alcohol produced permethylstyrene. Table 1 shows the results. Example 2 The procedure was performed in the same manner as in Example 1 except that the heating temperature was 15.5 ° C. Table 1 shows the results.
- Example 1 The procedure was performed in the same manner as in Example 1 except that the heating temperature was 184. Table 1 shows the results.
- Example 1 The procedure was performed in the same manner as in Example 1 except that the heating temperature was 194 ° C. Table 1 shows the results.
- ⁇ -methylstyrene yield (%) ⁇ _methylstyrene production amount (mo 1) Cumyl alcohol amount in Z raw material (mol) X 100
- the above was used as the bottom liquid. It was performed using raw materials, but when the heating temperature became 190 or more, it was found that the production of hexamethylstyrene, that is, the generation of water was remarkable.
- Example 4 The operation was performed in the same manner as in Example 4 except that the heating temperature was 15.5 ° C. Table 2 shows the results.
- Example 6 The procedure was performed in the same manner as in Example 4 except that the heating temperature was 174. Table 2 shows the results.
- Example 2 The operation was performed in the same manner as in Example 4 except that the heating temperature was 194 ° C. Table 2 shows the results.
- propylene oxide is recovered in high yield from a reaction solution in which cumenehydride-containing peroxide is reacted with propylene to produce propylene oxide, and the propylene oxide is purified. It is possible to provide a method for recovering propylene oxide, which is capable of minimizing the reduction in yield and the problem of corrosion in the process, and which is extremely advantageous from an industrial point of view.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003211927A AU2003211927A1 (en) | 2002-02-15 | 2003-02-12 | Method for recovering propylene oxide |
DE60320642T DE60320642D1 (de) | 2002-02-15 | 2003-02-12 | Verfahren zur gewinnung von propylenoxid |
KR10-2004-7012534A KR20040089627A (ko) | 2002-02-15 | 2003-02-12 | 프로필렌 옥시드의 회수 방법 |
EP03705069A EP1484326B1 (en) | 2002-02-15 | 2003-02-12 | Method for recovering propylene oxide |
US10/504,537 US20050085648A1 (en) | 2002-02-15 | 2003-02-12 | Method for recovering propylene oxide |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002038198A JP2003238546A (ja) | 2002-02-15 | 2002-02-15 | プロピレンオキサイドの回収方法 |
JP2002-38198 | 2002-02-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003068763A1 true WO2003068763A1 (fr) | 2003-08-21 |
Family
ID=27678153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2003/001421 WO2003068763A1 (fr) | 2002-02-15 | 2003-02-12 | Procede de recuperation d'oxyde de propylene |
Country Status (11)
Country | Link |
---|---|
US (1) | US20050085648A1 (ja) |
EP (1) | EP1484326B1 (ja) |
JP (1) | JP2003238546A (ja) |
KR (1) | KR20040089627A (ja) |
CN (1) | CN1307167C (ja) |
AT (1) | ATE393765T1 (ja) |
AU (1) | AU2003211927A1 (ja) |
DE (1) | DE60320642D1 (ja) |
ES (1) | ES2305442T3 (ja) |
TW (1) | TW200302826A (ja) |
WO (1) | WO2003068763A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2191790A3 (en) * | 2003-05-19 | 2012-10-17 | SeptRx, Inc. | Tissue distention device and related methods for therapeutic intervention |
JP2005097184A (ja) * | 2003-09-25 | 2005-04-14 | Sumitomo Chemical Co Ltd | プロピレンオキサイドの製造方法 |
JP2005097185A (ja) * | 2003-09-25 | 2005-04-14 | Sumitomo Chemical Co Ltd | プロピレンオキサイドの製造方法 |
WO2011118823A1 (en) * | 2010-03-26 | 2011-09-29 | Sumitomo Chemical Company, Limited | Method of producing propylene oxide |
TWI660942B (zh) | 2014-07-24 | 2019-06-01 | 大陸商中國石油化工科技開發有限公司 | Method and device for recovering refined propylene |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5319114A (en) * | 1993-09-23 | 1994-06-07 | Arco Chemical Technology, L. P. | Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal |
JP2003081953A (ja) * | 2001-09-12 | 2003-03-19 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3351635A (en) * | 1966-03-14 | 1967-11-07 | Halcon International Inc | Epoxidation process |
US5489366A (en) * | 1994-03-28 | 1996-02-06 | Texaco Chemical Inc. | Recovery of purified and substantially anhydrous propylene oxide |
JP2002322167A (ja) * | 2001-04-27 | 2002-11-08 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
-
2002
- 2002-02-15 JP JP2002038198A patent/JP2003238546A/ja active Pending
-
2003
- 2003-02-12 AU AU2003211927A patent/AU2003211927A1/en not_active Abandoned
- 2003-02-12 EP EP03705069A patent/EP1484326B1/en not_active Expired - Lifetime
- 2003-02-12 ES ES03705069T patent/ES2305442T3/es not_active Expired - Lifetime
- 2003-02-12 KR KR10-2004-7012534A patent/KR20040089627A/ko not_active Application Discontinuation
- 2003-02-12 CN CNB038038811A patent/CN1307167C/zh not_active Expired - Fee Related
- 2003-02-12 US US10/504,537 patent/US20050085648A1/en not_active Abandoned
- 2003-02-12 WO PCT/JP2003/001421 patent/WO2003068763A1/ja active IP Right Grant
- 2003-02-12 AT AT03705069T patent/ATE393765T1/de not_active IP Right Cessation
- 2003-02-12 TW TW092102906A patent/TW200302826A/zh unknown
- 2003-02-12 DE DE60320642T patent/DE60320642D1/de not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5319114A (en) * | 1993-09-23 | 1994-06-07 | Arco Chemical Technology, L. P. | Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal |
JP2003081953A (ja) * | 2001-09-12 | 2003-03-19 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1484326A4 (en) | 2006-03-08 |
ATE393765T1 (de) | 2008-05-15 |
EP1484326B1 (en) | 2008-04-30 |
DE60320642D1 (de) | 2008-06-12 |
AU2003211927A1 (en) | 2003-09-04 |
CN1307167C (zh) | 2007-03-28 |
ES2305442T3 (es) | 2008-11-01 |
KR20040089627A (ko) | 2004-10-21 |
JP2003238546A (ja) | 2003-08-27 |
CN1633423A (zh) | 2005-06-29 |
US20050085648A1 (en) | 2005-04-21 |
TW200302826A (en) | 2003-08-16 |
EP1484326A1 (en) | 2004-12-08 |
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