WO1997015542A1 - Process for purifying a 2,6-dialkylphenol - Google Patents
Process for purifying a 2,6-dialkylphenol Download PDFInfo
- Publication number
- WO1997015542A1 WO1997015542A1 PCT/US1996/017113 US9617113W WO9715542A1 WO 1997015542 A1 WO1997015542 A1 WO 1997015542A1 US 9617113 W US9617113 W US 9617113W WO 9715542 A1 WO9715542 A1 WO 9715542A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- washing
- process according
- metal hydroxide
- conducted
- solution
- Prior art date
Links
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
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
-
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/17—Saline water conversion
Definitions
- This invention relates to a process for converting an impure 2,6-dialkylphenol, such as produced in a catalyzed phenol ortho-alkylation process, into a highly pure product.
- the invention is particularly well-adapted for the purification of 2,6- diisopropylphenol produced by catalytic ortho-alkylation of phenol with propylene.
- impurities include 2,6-diisopropylbenzoquinone, 2-isopropyl-6-isopropenyl- phenol, 2,6-diisopropenylphenol and 2,2-dimethyl-4-isopropyl-l,3-benzodioxole.
- Jinno, M. Kataoka N. Sato and M. Honda describes a method of continuously separating components of a hydrous phenols mixture containing methanol by distillation.
- the method involves recovering methanol from the top ofa single distillation column, dragging water containing phenols as a side stream from the recovery section ofthe distillation column and the dehydrated phenols as a bottom product.
- This invention provides a new, economical and highly effective process for producing high purity 2,6-diisopropylphenol with the lower capital requirements of a batch distillation facility. More particularly, it has been found pursuant to this invention that washing impure 2,6-diisopropylphenol with aqueous alkali or alkaline earth metal hydroxide solution in an inert atmosphere prior to initiating distillation of the 2,6- diisopropylphenol completely eliminates the need for multi-column distillation procedures when seeking recovery of highly purified 2,6-diisopropylphenol.
- impure 2,6-diisopropylphenol for which the process is particularly well adapted.
- Such impure 2,6-diisopropylphenol is typically a reaction product from the catalytic ortho- alkylation of phenol with propylene, and especially where the catalyst used is an aluminum phenoxide catalyst in accordance with an ortho-alkylation process like that described in the previously cited patent to Ecke and Kolka.
- such impure or crude 2,6-diisopropylphenol comprises from 60 to 80 wt% of 2,6-diisopropylphenol, from 1 to 4 wt% of phenol, from 7 to 21 wt% of ortho-isopropylphenol, from 1 to 8 wt% of 2,4,6-triisopropylphenol, and from 0 to 4 wt% of one or more other phenolic compounds and/or phenolic ethers.
- DIP 2,6-diisopropylphenol
- inert environment means that, to the extent reasonably practicable, the material is kept free from exposure to air, oxygen or other oxidizing materials that would result in the formation of impurities in the material when subjected to elevated temperatures.
- this invention provides a process for the purification of an impure DIP mixture which contains at least one phenolic component having a boiling point below that of DIP and at least one phenolic component having a boiling point higher than that of DIP.
- Such process comprises washing the impure DIP mixture with aqueous alkali metal or alkaline earth metal hydroxide solution in an inert atmosphere and separating the aqueous and organic phases, washing the resulting organic phase with water, and then subjecting the water-washed organic phase to distillation in an inert environment to produce purified 2,6-diisopropylphenol.
- the phenolic components ofthe impure DIP mixture subjected to the process of this invention and having a boiling point below that of DIP may include, for example, phenol and/or one or more lower boiling mono-alkyl phenols.
- the higher boiling phenolic impurities include one or more triisopropyl phenols.
- any ofthe alkali or alkaline earth metal hydroxides may be used in the washing solution employed in the process of this invention.
- the alkali metal hydroxides will be sodium hydroxide or potassium hydroxide, or a combination of these, with sodium hydroxide being most preferred metal hydroxide for use in the practice of this invention.
- Calcium hydroxide is the preferred alkaline earth metal hydroxide. Mixtures of alkali metal hydroxide(s) and alkaline earth metal hydroxide(s) can also be used.
- alkali or alkaline earth metal oxide may be added to water to generate the alkali or alkaline earth metal hydroxide in situ.
- the aqueous alkali or alkaline earth metal solution will typically contain from 1 wt% to 50 wt% of the alkali metal hydroxide, and when using sodium hydroxide or potassium hydroxide, the solutions preferably will be 10 to 30 wt% solutions.
- the impure DIP mixture may be washed one or more times with aqueous alkali metal hydroxide solution, followed by one or more water washes, all in an inert atmosphere.
- the impure DIP is washed at least twice with an alkali metal hydroxide or alkaline earth metal hydroxide solution prior to washing of the separated organic phase with water.
- the inert atmosphere may consist of any ofthe inert gases, including but not limited to nitrogen, helium, argon, or neon. Nitrogen is the preferred inert atmosphere for economic reasons. The use of an inert atmosphere limits exposure to air and creation of undesirable impurities which result from oxidation reactions when the DIP is exposed to temperatures such as during the ensuing distillation.
- the order in which the impure DIP mixture and alkali or alkaline earth metal hydroxide solution are mixed to wash the impure DIP mixture is not crucial, permitting either the impure DIP mixture to be added to the metal hydroxide solution, or the metal hydroxide solution to be added to the impure DIP mixture, or the metal hydroxide solution and the impure DIP mixture to be added together simultaneously.
- separation ofthe aqueous and organic phases may be achieved by decantation, centrifugation or other similar separation techniques, with decantation being the preferred method.
- the resulting aqueous phase will contain alkali or alkaline earth metal salts ofthe low boiling phenolic impurities such as phenol, one or more monoisopropyl phenols and less sterically hindered phenols such as 2,4- diisopropylphenol. Acidification of the aqueous waste solution enables recovery of these phenolic values, including small amounts of DIP extracted during the washing. Accordingly, the aqueous waste may be utilized as a source of phenolic materials (for example, as recycle in the catalyzed phenol ortho-alkylation process) upon acidification and recovery ofthe phenols from the washing solutions.
- both the step of washing the impure DIP mixture with alkali metal hydroxide and/or alkaline earth metal hydroxide solution, and the washing of the resulting organic phase employ agitation of the materials.
- agitation may be employed, including but not limited to shaking or stirring.
- the temperature should be elevated to 25 °C to 100°C, preferably in the range of 50°C to 100°C.
- the water-washed organic phase is distilled by any conventional means.
- Such distillation may be conducted on either a batch, semi-continuous or continuous basis, with batch distillation being the preferred method for economic reasons.
- the distillation should be conducted in an inert environment to reduce, if not eliminate, formation of impurities in the DIP through oxidation reactions at elevated temperatures.
- caustic solution was collected into a beaker containing 10.4 gms of phosphoric acid and
- caustic solution consisting of 25 grams of sodium hydroxide and 125 grams of water
- the aqueous was between 7-8.
- Total weight ofthe organic phase was 53 grams.
- the process of this invention is well suited for producing DIP in purities of
- alkaline earth metal hydroxide or is an aqueous alkali metal hydroxide and/or aqueous alkaline earth metal hydroxide solution, means that the solution is formed (a) by
- alkali metal hydroxide or the alkaline earth metal hydroxide dissolves in the water and/or (b) by mixing at least one alkali metal oxide or alkaline earth metal oxide with water so that the alkali metal oxide or alkaline earth metal oxide goes into
- earth metal material in solution is probably, at least in part, in dissociated ionic form (e.g., as sodium cations and hydroxyl anions) is of no consequence.
- hydroxide and/or alkali metal oxide and/or alkaline earth metal hydroxide and/or alkaline earth metal oxide with water regardless of what inevitably takes place as a result of such mixing.
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)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69611459T DE69611459T2 (en) | 1995-10-26 | 1996-10-24 | METHOD FOR PURIFYING A 2, 6-DIALKYLPHENOL |
CA 2235843 CA2235843A1 (en) | 1995-10-26 | 1996-10-24 | Process for purifying a 2,6-dialkylphenol |
JP51680297A JP3901218B2 (en) | 1995-10-26 | 1996-10-24 | Purification method of 2,6-dialkylphenol |
EP96936959A EP0862544B1 (en) | 1995-10-26 | 1996-10-24 | Process for purifying a 2,6-dialkylphenol |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/548,788 | 1995-10-26 | ||
US08/548,788 US5591311A (en) | 1995-10-26 | 1995-10-26 | Process for purifying a 2,6-dialkylphenol |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997015542A1 true WO1997015542A1 (en) | 1997-05-01 |
Family
ID=24190402
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/017113 WO1997015542A1 (en) | 1995-10-26 | 1996-10-24 | Process for purifying a 2,6-dialkylphenol |
Country Status (5)
Country | Link |
---|---|
US (1) | US5591311A (en) |
EP (1) | EP0862544B1 (en) |
JP (1) | JP3901218B2 (en) |
DE (1) | DE69611459T2 (en) |
WO (1) | WO1997015542A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7097849B2 (en) * | 1998-08-19 | 2006-08-29 | Jagotec Ag | Injectable aqueous dispersions of propofol |
KR20000047871A (en) * | 1998-12-04 | 2000-07-25 | 강재헌 | A process for preparing high purity 2,6-diisopropylphenol |
WO2000034218A1 (en) * | 1998-12-04 | 2000-06-15 | Dong Kook Pharmaceutical Co., Ltd. | Process for purification of 2,6-diisopropyl phenol |
US8664452B2 (en) | 2010-06-23 | 2014-03-04 | Harman Finochem Limited | Process for preparing extra pure 2, 6-diisopropyl phenol |
EP2522651B1 (en) | 2011-05-12 | 2013-11-20 | Siegfried AG | Process for the purification of 2,6-diisopropyl phenol |
WO2021156776A1 (en) * | 2020-02-06 | 2021-08-12 | Nandkumar Chodankar | Simple manufacturing and purification technology for high purity propofol |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4897824A (en) * | 1972-03-22 | 1973-12-13 | ||
US3985812A (en) | 1968-10-02 | 1976-10-12 | Continental Oil Company | Caustic refining of 2,3,6-trimethylphenol |
US5175376A (en) | 1991-04-30 | 1992-12-29 | Leiras Oy | Process for the purification of 2,6-diisopropyl phenol |
US5264085A (en) | 1991-08-28 | 1993-11-23 | Mitsubishi Petrochemical Company, Ltd. | Method of separating components of phenols mixture by distillation |
JPH06256243A (en) * | 1993-03-08 | 1994-09-13 | Yotsukaichi Gosei Kk | Elimination of p-t-butylphenol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4634796A (en) * | 1985-03-25 | 1987-01-06 | Lummus Crest, Inc. | Production of high purity phenol |
US5091058A (en) * | 1990-02-20 | 1992-02-25 | Aristech Chemical Corporation | Purified para-cumylphenol |
US5487816A (en) * | 1994-06-24 | 1996-01-30 | Uop | Process for the reduction of phenol content in a crude organic stream recovered from a phenol stripper |
-
1995
- 1995-10-26 US US08/548,788 patent/US5591311A/en not_active Expired - Lifetime
-
1996
- 1996-10-24 JP JP51680297A patent/JP3901218B2/en not_active Expired - Fee Related
- 1996-10-24 EP EP96936959A patent/EP0862544B1/en not_active Expired - Lifetime
- 1996-10-24 WO PCT/US1996/017113 patent/WO1997015542A1/en active IP Right Grant
- 1996-10-24 DE DE69611459T patent/DE69611459T2/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3985812A (en) | 1968-10-02 | 1976-10-12 | Continental Oil Company | Caustic refining of 2,3,6-trimethylphenol |
JPS4897824A (en) * | 1972-03-22 | 1973-12-13 | ||
US5175376A (en) | 1991-04-30 | 1992-12-29 | Leiras Oy | Process for the purification of 2,6-diisopropyl phenol |
US5264085A (en) | 1991-08-28 | 1993-11-23 | Mitsubishi Petrochemical Company, Ltd. | Method of separating components of phenols mixture by distillation |
JPH06256243A (en) * | 1993-03-08 | 1994-09-13 | Yotsukaichi Gosei Kk | Elimination of p-t-butylphenol |
Non-Patent Citations (2)
Title |
---|
DATABASE WPI Section Ch Week 7410, Derwent World Patents Index; Class E14, AN 74-18283V, XP002023148 * |
DATABASE WPI Section Ch Week 9441, Derwent World Patents Index; Class E14, AN 94-329967, XP002023149 * |
Also Published As
Publication number | Publication date |
---|---|
JPH11513987A (en) | 1999-11-30 |
EP0862544A1 (en) | 1998-09-09 |
JP3901218B2 (en) | 2007-04-04 |
US5591311A (en) | 1997-01-07 |
DE69611459D1 (en) | 2001-02-08 |
EP0862544B1 (en) | 2001-01-03 |
DE69611459T2 (en) | 2001-05-31 |
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