NL8000193A - Bereiding van fenolen uit hydroperoxyden. - Google Patents
Bereiding van fenolen uit hydroperoxyden. Download PDFInfo
- Publication number
- NL8000193A NL8000193A NL8000193A NL8000193A NL8000193A NL 8000193 A NL8000193 A NL 8000193A NL 8000193 A NL8000193 A NL 8000193A NL 8000193 A NL8000193 A NL 8000193A NL 8000193 A NL8000193 A NL 8000193A
- Authority
- NL
- Netherlands
- Prior art keywords
- phenol
- glycol
- column
- distillation
- residue
- Prior art date
Links
- 150000002989 phenols Chemical class 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title description 6
- 150000002432 hydroperoxides Chemical class 0.000 title description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 97
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 52
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- 238000004821 distillation Methods 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 20
- 238000000354 decomposition reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000000895 extractive distillation Methods 0.000 claims description 10
- -1 isopropyl aromatic compound Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 44
- 238000000605 extraction Methods 0.000 description 37
- 239000000047 product Substances 0.000 description 27
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 25
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 18
- 238000005979 thermal decomposition reaction Methods 0.000 description 17
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 16
- 238000000746 purification Methods 0.000 description 11
- 239000012535 impurity Substances 0.000 description 9
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 6
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- MAUHXSLDMRIHLY-UHFFFAOYSA-N 1-methyl-2-pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1C MAUHXSLDMRIHLY-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- IOHJVFLGIQPBKQ-UHFFFAOYSA-N 2-methylpent-1-enylbenzene Chemical class CCCC(C)=CC1=CC=CC=C1 IOHJVFLGIQPBKQ-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 229930007927 cymene Natural products 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GDEQPEBFOWYWSA-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C)=C1C GDEQPEBFOWYWSA-UHFFFAOYSA-N 0.000 description 1
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 241001292274 Eumenes Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- 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
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP101279A JPS5594326A (en) | 1979-01-11 | 1979-01-11 | Preparation of phenol |
| JP101279 | 1979-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8000193A true NL8000193A (nl) | 1980-07-15 |
Family
ID=11489656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8000193A NL8000193A (nl) | 1979-01-11 | 1980-01-11 | Bereiding van fenolen uit hydroperoxyden. |
Country Status (8)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4480134A (en) * | 1983-04-05 | 1984-10-30 | General Electric Company | Process for preparing phenol and acetone from cumene |
| US4567304A (en) * | 1983-04-05 | 1986-01-28 | General Electric Company | Process for preparing acetone and phenol |
| JPH0390043A (ja) * | 1989-08-31 | 1991-04-16 | Agency Of Ind Science & Technol | フェノールおよびその誘導体の回収方法 |
| JP3265659B2 (ja) * | 1992-06-05 | 2002-03-11 | 住友化学工業株式会社 | フェノールの精製方法 |
| IT1271279B (it) * | 1994-12-15 | 1997-05-27 | Enichem Spa | Processo per il recupero di fenolo da un flusso acquoso contenente na2 so4 |
| US6965056B1 (en) * | 1999-05-03 | 2005-11-15 | Shell Oil Company | Removal of salts in the manufacture of phenolic compound |
| EP2011807B1 (en) | 2006-04-17 | 2016-02-24 | Asahi Kasei Chemicals Corporation | Method for purifying -methylstyrene, and heat-resistant styrene copolymer using the -methylstyrene |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH288171A (fr) * | 1950-09-20 | 1953-01-15 | Distillers Co Yeast Ltd | Procédé de préparation du phénol. |
| US3331755A (en) * | 1964-12-18 | 1967-07-18 | Consolidation Coal Co | Extractive distillation of 2, 6-xylenol with glycol |
| IT998154B (it) * | 1973-06-15 | 1976-01-20 | Sir Soc Italiana Resine Spa | Procedimento per la separazione e la purificazione di paracumil fenolo |
| FR2245593B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-08-31 | 1976-06-18 | Rhone Poulenc Ind | |
| GB1574420A (en) * | 1976-12-18 | 1980-09-03 | Bp Chem Int Ltd | Process for recovering crude phenol from catalyst-free cumene hydroperoxide cleavage reaction products |
-
1979
- 1979-01-11 JP JP101279A patent/JPS5594326A/ja active Pending
-
1980
- 1980-01-03 US US06/109,214 patent/US4271322A/en not_active Expired - Lifetime
- 1980-01-08 GB GB8000536A patent/GB2040930B/en not_active Expired
- 1980-01-11 NL NL8000193A patent/NL8000193A/nl not_active Application Discontinuation
- 1980-01-11 FR FR8000626A patent/FR2446269A1/fr active Granted
- 1980-01-11 DE DE19803000899 patent/DE3000899A1/de not_active Withdrawn
- 1980-01-11 CA CA000343483A patent/CA1144572A/en not_active Expired
- 1980-01-11 IT IT19159/80A patent/IT1129966B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1129966B (it) | 1986-06-11 |
| GB2040930B (en) | 1983-05-05 |
| DE3000899A1 (de) | 1980-07-24 |
| FR2446269B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-01 |
| IT8019159A0 (it) | 1980-01-11 |
| US4271322A (en) | 1981-06-02 |
| JPS5594326A (en) | 1980-07-17 |
| GB2040930A (en) | 1980-09-03 |
| FR2446269A1 (fr) | 1980-08-08 |
| CA1144572A (en) | 1983-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |