TWI262912B - System and method for purifying cumene hydroperoxide cleavage products - Google Patents
System and method for purifying cumene hydroperoxide cleavage products Download PDFInfo
- Publication number
- TWI262912B TWI262912B TW091133633A TW91133633A TWI262912B TW I262912 B TWI262912 B TW I262912B TW 091133633 A TW091133633 A TW 091133633A TW 91133633 A TW91133633 A TW 91133633A TW I262912 B TWI262912 B TW I262912B
- Authority
- TW
- Taiwan
- Prior art keywords
- aqueous salt
- impurities
- salt phase
- water
- aqueous
- Prior art date
Links
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000003776 cleavage reaction Methods 0.000 title claims abstract description 43
- 230000007017 scission Effects 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 78
- 239000012535 impurity Substances 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 238000010438 heat treatment Methods 0.000 claims abstract description 37
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 16
- 238000004891 communication Methods 0.000 claims abstract description 15
- 239000012530 fluid Substances 0.000 claims abstract description 14
- 239000012670 alkaline solution Substances 0.000 claims abstract description 7
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims description 94
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 14
- 235000011152 sodium sulphate Nutrition 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000005336 cracking Methods 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 230000002079 cooperative effect Effects 0.000 claims description 8
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 73
- 239000012071 phase Substances 0.000 description 60
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000007788 liquid Substances 0.000 description 15
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000003377 acid catalyst Substances 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 3
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 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 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000001032 ion-exclusion chromatography Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000005887 phenylation reaction Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- -1 sodium oxyhydroxide Chemical compound 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- 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
- B01J19/0086—Processes carried out with a view to control or to change the pH-value; Applications of buffer salts; Neutralisation reactions
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- 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
- B01J2219/00004—Scale aspects
- B01J2219/00006—Large-scale industrial plants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/683,190 US6573408B1 (en) | 2001-11-29 | 2001-11-29 | System and method for purifying cumene hydroperoxide cleavage products |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200300411A TW200300411A (en) | 2003-06-01 |
| TWI262912B true TWI262912B (en) | 2006-10-01 |
Family
ID=24742928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091133633A TWI262912B (en) | 2001-11-29 | 2002-11-18 | System and method for purifying cumene hydroperoxide cleavage products |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6573408B1 (enExample) |
| EP (1) | EP1458663B1 (enExample) |
| JP (1) | JP4498739B2 (enExample) |
| KR (1) | KR20050058244A (enExample) |
| CN (1) | CN100369879C (enExample) |
| AT (1) | ATE355260T1 (enExample) |
| AU (1) | AU2002353928A1 (enExample) |
| BR (1) | BR0214624A (enExample) |
| DE (1) | DE60218528T2 (enExample) |
| ES (1) | ES2281561T3 (enExample) |
| TW (1) | TWI262912B (enExample) |
| WO (1) | WO2003048094A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7034192B2 (en) * | 2004-03-24 | 2006-04-25 | Sunoco Inc. (R&M) | Method for removal of acetol from phenol |
| US7186866B1 (en) * | 2005-11-14 | 2007-03-06 | Sunoco, Inc. (R&M) | Process for recovery of cumene hydroperoxide decomposition products by distillation |
| JP4996861B2 (ja) * | 2006-02-23 | 2012-08-08 | 三井化学株式会社 | 回収フェノール類の精製方法 |
| EP1847522A1 (en) * | 2006-04-18 | 2007-10-24 | INEOS Phenol GmbH & Co. KG | Process for removal of hydroxyacetone from phenol |
| CN109180437A (zh) * | 2018-09-06 | 2019-01-11 | 常州大学 | 管式连续流反应器中过氧化氢异丙苯分解制备苯酚的方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734085A (en) | 1956-02-07 | Removal of salts from acetone-phenol mixtures | ||
| US2744143A (en) | 1956-05-01 | filar | ||
| US2992169A (en) | 1961-07-11 | Inven | ||
| US3335070A (en) | 1964-06-18 | 1967-08-08 | Hercules Inc | Phenol purification by base addition and plural distillation |
| US3437699A (en) | 1965-11-19 | 1969-04-08 | Skelly Oil Co | Phenol purification |
| GB1148907A (en) | 1965-11-26 | 1969-04-16 | Ici Ltd | Purification of phenol |
| US3862244A (en) | 1967-05-29 | 1975-01-21 | Rhone Poulenc Sa | Process for the purification of phenol |
| US3692845A (en) | 1969-03-12 | 1972-09-19 | Allied Chem | Purification of phenol |
| US3965187A (en) | 1970-07-02 | 1976-06-22 | Allied Chemical Corporation | Hydrogenation of phenol |
| GB1412308A (en) | 1973-01-11 | 1975-11-05 | Bp Chem Int Ltd | Removal of mineral acid catalyst from cumene hydroperoxide cleavage products |
| US4092360A (en) | 1977-05-04 | 1978-05-30 | Allied Chemical Corporation | Production of cyclohexanone |
| US4298765A (en) | 1980-03-26 | 1981-11-03 | Allied Corporation | Purification of phenol with reduced energy consumption |
| US4334107A (en) | 1980-11-11 | 1982-06-08 | Allied Chemical Corporation | Catalytic purification of phenol |
| IT1227668B (it) | 1988-12-02 | 1991-04-23 | Montedipe S P A M | Processo per il recupero del fenolo da uno spurgo di rettifica |
| IT1248679B (it) | 1990-06-01 | 1995-01-26 | Enichem Anic Spa | Procedimento per la purificazione di fenolo |
| JPH05286879A (ja) | 1992-04-03 | 1993-11-02 | Mitsui Petrochem Ind Ltd | 高純度フェノールの製造方法 |
| RU2111203C1 (ru) | 1993-12-01 | 1998-05-20 | Закошанский Владимир Михайлович | Способ очистки фенола от органических примесей |
| US5414154A (en) | 1994-06-06 | 1995-05-09 | Alliedsignal Inc. | Phenol with low levels of methylbenzofuran |
| US5491268A (en) | 1994-09-23 | 1996-02-13 | General Electric Company | Process for removal of acidic compounds from phenol process streams |
| US5510543A (en) | 1994-12-09 | 1996-04-23 | General Electric Company | Removal and neutralization of acid catalyst from products of cumene hydroperoxide cleavage |
| US6066767A (en) | 1999-02-10 | 2000-05-23 | Illa International, Llc | Method of purifying cumene hydroperoxide decomposition products from hydroxyacetone and from other carbonyls |
-
2001
- 2001-11-29 US US09/683,190 patent/US6573408B1/en not_active Expired - Lifetime
-
2002
- 2002-10-29 DE DE60218528T patent/DE60218528T2/de not_active Expired - Lifetime
- 2002-10-29 JP JP2003549289A patent/JP4498739B2/ja not_active Expired - Fee Related
- 2002-10-29 CN CNB028265564A patent/CN100369879C/zh not_active Expired - Fee Related
- 2002-10-29 ES ES02789328T patent/ES2281561T3/es not_active Expired - Lifetime
- 2002-10-29 KR KR1020047008073A patent/KR20050058244A/ko not_active Ceased
- 2002-10-29 BR BR0214624-0A patent/BR0214624A/pt not_active IP Right Cessation
- 2002-10-29 WO PCT/US2002/034786 patent/WO2003048094A1/en not_active Ceased
- 2002-10-29 AT AT02789328T patent/ATE355260T1/de not_active IP Right Cessation
- 2002-10-29 AU AU2002353928A patent/AU2002353928A1/en not_active Abandoned
- 2002-10-29 EP EP02789328A patent/EP1458663B1/en not_active Expired - Lifetime
- 2002-11-18 TW TW091133633A patent/TWI262912B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1458663A1 (en) | 2004-09-22 |
| US20030100800A1 (en) | 2003-05-29 |
| ES2281561T3 (es) | 2007-10-01 |
| TW200300411A (en) | 2003-06-01 |
| EP1458663B1 (en) | 2007-02-28 |
| DE60218528D1 (de) | 2007-04-12 |
| JP4498739B2 (ja) | 2010-07-07 |
| CN1610654A (zh) | 2005-04-27 |
| CN100369879C (zh) | 2008-02-20 |
| KR20050058244A (ko) | 2005-06-16 |
| DE60218528T2 (de) | 2007-11-22 |
| AU2002353928A1 (en) | 2003-06-17 |
| ATE355260T1 (de) | 2006-03-15 |
| US6573408B1 (en) | 2003-06-03 |
| JP2005511675A (ja) | 2005-04-28 |
| BR0214624A (pt) | 2004-11-23 |
| WO2003048094A1 (en) | 2003-06-12 |
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