WO2003018528A1 - Abtrennung von verunreinigungen und/oder wertstoffen aus diarylcarbonathaltigen lösungen durch lösungskristallisation - Google Patents
Abtrennung von verunreinigungen und/oder wertstoffen aus diarylcarbonathaltigen lösungen durch lösungskristallisation Download PDFInfo
- Publication number
- WO2003018528A1 WO2003018528A1 PCT/EP2002/009105 EP0209105W WO03018528A1 WO 2003018528 A1 WO2003018528 A1 WO 2003018528A1 EP 0209105 W EP0209105 W EP 0209105W WO 03018528 A1 WO03018528 A1 WO 03018528A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- diaryl carbonate
- crystals
- solution
- diaryl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
Definitions
- the present invention relates to a process for the separation of impurities and for the production of substantially adduct-free diaryl carbonate from reaction solutions containing diaryl carbonate by solution crystallization, a mother liquor and the pure diaryl carbonate (DAC) being obtained as crystals.
- the mother liquor contains the catalyst components and can be in the
- this treatment leads to an increase in the water content of the adduct crystals, which in the downstream distillation columns, i. for DPC isolation and water separation from the washing solution used, leads to DPC losses through hydrolysis.
- essential process parameters e.g. to the type of reactor, temperature control, stirrer geometry, stirring power, etc., not disclosed.
- EP-A 0 687 666 describes a process for the purification of diphenyl carbonate by fractional melt crystallization of highly concentrated reaction solutions in the temperature range from 45-85 ° C.
- the achievable diphenyl carbonate purities are between 97.5 and 99.5%.
- a disadvantage of this process is the restriction to reaction solutions with a diaryl carbonate content of greater than 70% by weight. Reaction solutions with diaryl carbonate contents below 70% by weight cannot be processed by this process and would therefore have to be concentrated to the required contents, for example by distillation. With this thermal load, the catalyst system causes side reactions and is deactivated itself. For these reasons, the process is uneconomical and cumbersome for reaction solutions with diphenyl carbonate contents below 70% by weight.
- the invention accordingly relates to a method for separating catalyst systems and essentially adduct-free diaryl carbonate, the catalyst systems being able to contain a platinum metal catalyst, a cocatalyst, a bromide salt and a base, from reaction solutions, the aromatic carbonates of the formula (I)
- R is a substituted or unsubstituted C 6 -C 24 aryl, and at least one aromatic hydroxy compound of the formula (II), RAW (II)
- a) a solution of hydroxyaromatic, diaryl carbonate and catalyst components is prepared in an aromatic solvent, b) solution crystallization is initiated by lowering the temperature and possibly inoculating, c) the catalyst-containing mother liquor is separated from the crystals, and optionally d) the mother liquor is fed into the reactor Production of diaryl carbonate is recycled or worked up to obtain valuable materials, and e) adhering catalyst residues and other impurities are removed from the crystals by washing.
- Preferred, particularly preferred or very particularly preferred are embodiments which make use of the parameters, compounds, definitions and explanations mentioned under preferred, particularly preferred or very particularly preferred.
- the platinum metal catalysts consist of at least one Group VIIIB noble metal, preferably palladium. It can be added in various forms in the process according to the invention.
- Palladium can be in metallic form, for example as palladium black or on a support such as Pd / C, Pd / Al 2 O 3 , Pd / SiO 2 or preferably in the form of palladium compounds with oxidation states 0 and +2, such as palladium (II) acetylacetonate, halides, carboxylates of C 2 -C 8 carboxylic acids, dicarboxylates such as oxalate, nitrate, sulfate, oxides or palladium complexes, for example carbon monoxide, olefins, amines, nitriles, phosphorus compounds and may contain halides can be used. Palladium bromide and palladium acetylacetonate are particularly preferred.
- the amount of platinum metal catalyst present is not restricted in the process according to the invention. Sufficient catalyst is preferably added such that the concentration of the metal in the reaction mixture is 1 to 3000 ppm, and concentrations of 5 to 500 ppm are particularly preferred.
- Periodic table of the elements (Mendeleev), possibly also mixtures thereof, before, whereby the metal can be used in different oxidation levels.
- Pb, Ti, Mn, Cu, Co, V are preferred Zn, Ce and Mo used.
- lead (II), manganese (II), manganese (III), copper®, copper (II), cobalt (II), cobalt (III), vanadium (III) and vanadium (IV) especially called manganese (II), manganese (III), cobalt (II), cobalt (III).
- the metals can be used, for example, as halides, oxides, carboxylates of C 2 -C 8 -carboxylic acids, diketonates or nitrates and as complex compounds which, for example, carbon monoxide, olefins, aromatic and aliphatic mono- or polyamines, phosphorus compounds, pyridines, bipyridines, Terpyridines, quinolines,
- Mn, Cu, Mo, Pb and Ce are particularly preferably used.
- Manganese compounds are very particularly preferably used in the process according to the invention, particularly preferably manganese (II) and manganese (III) complex, very particularly preferably manganese (II) acetylacetonate or manganese (III) acetylacetonate, and manganese (II) bromide.
- the cocatalyst is present in a concentration in the range from 0.0001 to 20% by weight of the reaction mixture, the concentration range from 0.001 to 5% by weight, particularly preferably 0.005 to 2% by weight, being preferred.
- the bromide compounds mentioned in the context of the present invention are, for example, the alkali bromides or alkaline earth bromides, but preferably the bromide salts of organic cations.
- the organic cations can be, for example, ammonium, guanidinium, phosphonium or sulfonium salts substituted with organic radicals, if appropriate also mixtures thereof.
- Ammonium, guanidinium, phosphonium and sulfonium salts are suitable for use in the process according to the invention, the organic radicals being C 6 to C 10 aryl, C 7 to C 2 aralkyl and / or d to C 20 -Alkyl residues contain.
- Ammonium salts are preferably present which carry C 6 to C 10 aryl, C to C ⁇ aralkyl and / or Ci to C 20 alkyl radicals as organic radicals, tetrabutylammonium bromide and tetrabutylphosphonium bromide are particularly preferred.
- the amount of such a quaternary salt can be, for example, 0.1-20% by weight, based on the weight of the reaction mixture. This amount is preferably 0.5-15% by weight, particularly preferably 1-5% by weight.
- Bases present in the process according to the invention are alkali metal hydroxides, alkali metal salts or quaternary salts of weak acids such as alkali tert-butylates or alkali metal salts or quaternary salts of aromatic hydroxy compounds of the formula (II), in which R has the meaning given above.
- An alkali metal salt or quaternary salt of the aromatic hydroxy compound is very particularly preferably
- Lithium, sodium, potassium, rubidium or cesium salts can be present as alkali salts.
- Lithium, sodium and potassium phenolates are preferably present, particularly preferably potassium phenolate.
- ammonium, phosphonium, pyridinium, sulfonium or guanidinium salts can be present which are organic radicals C 6 - to C 8 aryl, C 7 to C 8 aralkyl and / or Ci to C 20 - Possess alkyl radicals.
- the residues can all be the same or different, and mixtures of several quaternary salts can optionally be used.
- the same cation, which is also present as a bromide, is preferably present.
- Tetraphenylphosphonium, tetrabutylammonium, tetrabutylphosphonium are further preferred, and tetrabutylammonium is particularly preferred.
- trialkylamine bases such as tributylamine, diisopropylefhylamine,
- DBU, DBN are available.
- the base is present in an amount that is independent of the stoichiometry.
- the ratio of platinum metal, e.g. Palladium to base is preferably such that per mole of platinum metal, e.g. Palladium, 0.1 to 5000, preferably 1 to 1000, particularly preferably 10 to 300 equivalents of base are present.
- the aromatic hydroxy compounds ROH are preferably substituted monohydroxy compounds such as phenol, o-, m- or p-cresol, o-, m- or p-chlorophenol, o-, m- or p-ethylphenol, o- , m- or p-
- Propylphenol, o-, m- or p-methoxyphenol, 2,6-dimethylphenol, 2,4-dimethylphenol, 3,4-dimethylphenol, 1-naphthol, 2-naphthol, phenol and o-, m are particularly preferred - and p-cresol, very particularly preferably phenol.
- Di- or polyhydroxy compounds such as resorcinol and hydroquinone, and tris and bisphenols
- 2,2-bis (4-hydroxyphenyl) propane bisphenol A
- 2,2-bis (3,5-dimethyl-4 -hydroxyphenyl) propane 1,1-bis (4-hydroxyphenyl) -cyclohexane
- l'-spiro (bis) -indane 2,4 '-Hydroxybiphenyl or 4,4'-hydroxybiphenyl can be converted in a similar manner to oligoaryl carbonates.
- Solutions containing such oligocarbonates and catalyst components can also be worked up in accordance with the process according to the invention. Mixtures of oligocarbonates with diaryl carbonates and optionally catalysts can also be worked up accordingly and then reacted further in solid phase or melt reactions.
- the dilution of the reaction mixture in step a) can be omitted if the reaction is already carried out in an aromatic solvent.
- the solvent of the reaction is then preferably also used for crystallization, since separation and mixing operations can thus be avoided.
- Unsubstituted or mono- or polysubstituted mono- or polynuclear aromatic compounds can be used as aromatic solvents.
- Possible substituents are e.g. B. -CC 2 o-alkyl, C 7 -C 2 o-aralkyl, C 6 -C 30 aryl, alkoxy radicals, nitro groups, sulfonates, sulfones or halogens. Examples include benzene, toluene, anisole, chlorobenzene, dichlorobenzenes, fluorobenzene, xylenes, mesitylene, naphthalene and biphenyl.
- the aromatic solvent preferably has a boiling point of about 70 to 180 ° C, particularly preferably of about 80 to 150 ° C. Mixtures of aromatic solvents can also be used, but pure solvents are preferred. Chlorobenzene or chlorobenzene-containing solvent mixtures are particularly preferably used, very particularly preferably chlorobenzene.
- the solvent is used in step a) in a concentration of about 3 to 80%, preferably 10 to 60% by weight, particularly preferably 20 to 50% by weight, based on the entire reaction mixture.
- the desired concentration can be partially by dilution with solvent or vice versa by concentration steps known to the person skilled in the art
- Solvent separation for example by vacuum distillation, can be set. Part of the hydroxyaromatic compound ROH can optionally also be separated off.
- step b crystallization technologies can be used in step b), such as those used in chemical engineering. 57 (1985) 91 ff or J. W. Mullin in Ullmamf's Encyclopedia of Industrial Chemistry, 6th ed., 2001 electronic release: Crystallization and Precipitation.
- the frequently used stirred tank crystallizers can be used according to the regulations and recommendations of M. Zlokarnik, H.
- the solution crystallization can be carried out in a discontinuous agitator crystallizer with an anchor stirrer or cross-bar stirrer without a baffle.
- a specific stirring power P / N of about 0.02 to 5 W / 1 can be used. It is preferred to work with specific stirring powers of about 0.05 to 2 W / 1, particularly preferably with about 0.2 to 0.5 W / 1.
- the cooling in step b) can take place according to different temperature-time profiles. Linear profiles with a constant cooling rate and convex profiles in which the cooling rates are lower at the beginning of the crystallization than at the end of the crystallization are preferred.
- variable or fixed cooling rates that are run through are in the range of approximately
- the cooling rate is preferably always less than about 10 K h, particularly it is preferably in the range from about 0.5 to 8 K / h, very particularly preferably in the range from about 1 to about 6 K / h.
- the start temperature for cooling depends on the weighing concentration
- the final cooling temperature depends on the desired suspension concentration.
- the final cooling temperature is preferably set such that a solids content of approximately 10 to 40% by weight, particularly preferably approximately 15-30% by weight, is present at this temperature.
- the starting temperature is about 20 to 60 ° C., preferably about 25 to 40 ° C., particularly preferably about 28 to 38 ° C.
- the desired suspension concentration can then be achieved by cooling by a surprisingly small temperature difference of approximately 20 to 40 K to final temperatures of approximately -10 to 20 ° C., preferably approximately 0 to 15 ° C. This means that both the crystallization start and end temperatures are in a very favorable range for technical implementation.
- the system is preferably inoculated with a nucleating agent at the crystallization start temperature; the diaryl carbonate to be crystallized is particularly preferably used.
- the amount of nucleating agent is about 0.01 to 10%, preferably about 0.02 to 1%, based on the solids yield obtained after crystallization.
- a subsequent stirring time of about 1 to 2 hours is preferably maintained.
- step c) the resulting catalyst-containing mother liquor is separated from the crystals by known processes such as, for example, decanting, pressing, suction filtering, filtering, centrifuging, etc.
- the mother liquor obtained is optionally combined in step d) with further solutions obtained during washing and can be used for recycling the catalyst components directly or after further work-up steps, for. B. the complete or partial removal of the solvent can be returned to the reaction. Alternatively, some or all of the mother liquor can be worked up to obtain the valuable materials, for example platinum group metals. The return is the preferred variant.
- the resulting crystals also do not consist of an adduct (e.g. phenol-diphenyl carbonate adduct), but essentially of diphenyl carbonate, even with low diaryl carbonate contents.
- an adduct e.g. phenol-diphenyl carbonate adduct
- Adhesive impurities such as catalyst components, by-products or possibly also hydroxyaromatic ROH can be processed in a preferred processing variant e) by washing the crystals with an anhydrous washing solution, e.g. by
- Suitable washing solutions have the lowest possible (additional) solubility for diaryl carbonates, but a good one for the components which are otherwise present in the reaction mixture.
- Native substances are preferably used as a washing solution, e.g. B. the hydroxyaromatic ROH, the diaryl carbonate, the solvent or mixtures of these compounds. Washing with the essentially pure crystallization solvent is particularly preferred. Washing with a mixture consisting essentially of solvent / diaryl carbonate or solvent / diaryl carbonate / ROH is very particularly preferred, preference being given to using solutions which are saturated with diaryl carbonate and contain as little ROH as possible.
- the detergent preferably has a temperature of about -15 to 50 ° C, particularly preferably about -10 to 20 ° C, detergents not saturated with diaryl carbonate should be as cold as possible. It is very particularly preferred to wash with a saturated solution of the diaryl carbonate at about the final crystallization temperature.
- the washing process is carried out with an amount of about 20 to 500% by weight, preferably about 40 to 400% by weight, particularly preferably about 50 to 350% by weight, of the washing solution based on the filter cake.
- the crystals are preferably reacted with portions of the washing liquid in several processes, for example in such a way that the crystals are first suspended and filtered with 25 to 40% by weight of the total amount of the washing liquid and then with a further 60 to 75% by weight. -% the process is repeated.
- the washing solution then optionally contains catalyst components, hydroxy aromatic compound ROH and any by-products. It can be worked up in various ways to obtain or separate these components. Variants in which the detergent is wholly or partly returned to the reaction are preferred. The detergent is preferred, if necessary after working up, for. B. partial or complete separation of the solvent, combined with the mother liquor, possibly further processed and / or returned to the reaction.
- the crystals are further purified during washing and, surprisingly, consists of essentially adduct-free diaryl carbonate with adhering solvent residues.
- the diaryl carbonate can be adherent Solvent e.g. B. can be freed by applying a vacuum or washing with another, more volatile, washing liquid. The further washing liquid can then also be separated off by applying a vacuum. If necessary, a purity required for the intended application can already be achieved.
- Another object of the invention is the separation of diaryl carbonate R-O-CO-O-R from mixtures which, in addition to the diaryl carbonate, contain hydroxyaromatics ROH and possibly other impurities.
- the crystals obtained do not contain any adducts of ROH and R-O-CO-O-R even in the case of mixtures with far less than 70% by weight of phenol, but, as mentioned, on the contrary essentially consist of pure diaryl carbonate and solvent. It offers a cleaning process for diaryl carbonates that is efficient and less energy-intensive than distillation.
- a particular advantage of the process according to the invention is that reaction solutions whose diaryl carbonate content is in a wide range from about 25 to 95% by weight can be used.
- Mixtures of various diaryl carbonates, e.g. B. cresylphenyl carbonate and diphenyl carbonate can be contained in the reaction solutions which can be used and can be purified by the process according to the invention.
- the processes according to the invention are preferably used in the oxidative direct carbonylation of ROH to diaryl carbonates R-O-CO-OR, but are in no way limited to these.
- the method is also very well applicable.
- diaryl carbonates in the production of diaryl carbonates by transesterification of dialkyl carbo- nates or other diaryl carbonates or in the decarbonylation of diaryl oxalates. In principle, it can also be used in manufacturing processes that are based on the reaction of ROH with phosgene.
- a a solution of the mixture is prepared in an aromatic solvent
- Tetrabutylammomum bromide is considered in the examples as an example of an impurity or catalyst component to be recycled.
- TBAB is a key substance that occurs in the feed as the catalyst component with the highest concentration and whose cleaning factor is easiest to measure in the crystals.
- the reaction solutions can be obtained, for example, by the known processes for the preparation of diaryl carbonates, for example according to DE-A 19 605 167.
- the examples relate to the particularly preferred preparation of diphenyl carbonate from phenol; however, it is easy for a person skilled in the art to adapt the conditions to be set to the physical data of other diaryl carbonates.
- Reaction solutions which included phenol, diphenyl carbonate (DPC), monochlorobenzene (MCB) and tetrabutylammomum bromide (TBAB), were placed in a stirrer as feed;
- DPC diphenyl carbonate
- MB monochlorobenzene
- TBAB tetrabutylammomum bromide
- the mixture is inoculated with diphenyl carbonate at 34 ° C., cooled at a cooling rate of 5K / h and the solids content of the reaction mixture is determined. The result is shown in Tab. 1.
- a mass of 500 g of a mixture of the composition 35.1 wt .-% MCB, 16.2% phenol, 8.1% tetrabutylammonium bromide and 40.6% diphenyl carbonate is inoculated at 31 ° C. with 0.1 g DPC and with a stirred crystallization apparatus cooled at a cooling rate of 5K / h to a final crystallization temperature of 25 ° C. The crystals are filtered off and then washed with 100 ml of a saturated solution of DPC in MCB. 109.1 g of crystals are obtained.
- the composition of the samples is shown in Tab. 2.
- a quantity of 900 g of a mixture of the composition 35.1% by weight of MCB, 16.2% of phenol, 8.1% of tetrabutylammonium bromide and 40.6% of diphenyl carbonate is inoculated with 1% of diphenyl carbonate at 34 ° C. and then at a cooling rate cooled from 5K / h to a final crystallization temperature of 10 ° C.
- the crystals are filtered off and then washed with different amounts of a saturated solution of diphenyl carbonate in chlorobenzene and washed with 10 ml of cyclohexane.
- the results, expressed as the amount of detergent relative to the mass of the filter cake, are shown in Table 3.
- a reaction mixture of 900 g from the aromatic direct carbonylation of phenol with a composition of 35.6% by weight MCB, 17.0% phenol, 7.2% tetrabutylammonium bromide and 40.2% diphenyl carbonate is in a stirrer crystal with an anchor stirrer under the specific stirring power
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02796231A EP1425259A1 (de) | 2001-08-27 | 2002-08-14 | Abtrennung von verunreinigungen und/oder wertstoffen aus diarylcarbonathaltigen lösungen durch lösungskristallisation |
KR10-2004-7002844A KR20040041587A (ko) | 2001-08-27 | 2002-08-14 | 용액 결정화에 의한 디아릴카르보네이트 함유 용액의불순물 및(또는) 유용한 생성물의 분리 |
JP2003523193A JP2005501117A (ja) | 2001-08-27 | 2002-08-14 | ジアリールカーボネート含有溶液からの溶液結晶化による不純物および/または貴重な物質の分離 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10141829A DE10141829A1 (de) | 2001-08-27 | 2001-08-27 | Abtrennen von Verunreinigungen und/oder Wertstoffen aus diarylcarbonathaltigen Lösungen durch Lösungskristallisation |
DE10141829.9 | 2001-08-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003018528A1 true WO2003018528A1 (de) | 2003-03-06 |
Family
ID=7696691
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/009105 WO2003018528A1 (de) | 2001-08-27 | 2002-08-14 | Abtrennung von verunreinigungen und/oder wertstoffen aus diarylcarbonathaltigen lösungen durch lösungskristallisation |
Country Status (8)
Country | Link |
---|---|
US (2) | US6734319B2 (de) |
EP (1) | EP1425259A1 (de) |
JP (1) | JP2005501117A (de) |
KR (1) | KR20040041587A (de) |
CN (1) | CN1549807A (de) |
DE (1) | DE10141829A1 (de) |
TW (1) | TW574209B (de) |
WO (1) | WO2003018528A1 (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6173164B2 (ja) * | 2013-10-18 | 2017-08-02 | 三菱電機株式会社 | 照明制御装置 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5221798A (en) * | 1988-12-30 | 1993-06-22 | Amoco Corporation | Changing the regiopurity of mixtures containing 4,4'-disubstituted diphenyl carbonates |
EP0790231A1 (de) * | 1996-02-13 | 1997-08-20 | Bayer Ag | Verfahren zur extraktiven Abtrennung von Diarylcarbonaten und den zugrundeliegenden aromatischen Hydroxyverbindungen aus Reaktionslösungen |
JP2001288148A (ja) * | 2000-04-07 | 2001-10-16 | Teijin Ltd | 芳香族カーボネートの製造方法 |
JP2001288149A (ja) * | 2000-04-07 | 2001-10-16 | Teijin Ltd | ジアリールカーボネートの分離回収方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5239106A (en) | 1992-08-17 | 1993-08-24 | General Electric Company | Method of recovering and purifying diphenylcarbonate from phenolic solutions thereof |
DE4420778A1 (de) | 1994-06-15 | 1995-12-21 | Bayer Ag | Verfahren zur Reinigung von Diphenylcarbonat |
-
2001
- 2001-08-27 DE DE10141829A patent/DE10141829A1/de not_active Withdrawn
-
2002
- 2002-08-14 WO PCT/EP2002/009105 patent/WO2003018528A1/de active Application Filing
- 2002-08-14 EP EP02796231A patent/EP1425259A1/de not_active Withdrawn
- 2002-08-14 JP JP2003523193A patent/JP2005501117A/ja active Pending
- 2002-08-14 KR KR10-2004-7002844A patent/KR20040041587A/ko not_active Application Discontinuation
- 2002-08-14 CN CNA02816900XA patent/CN1549807A/zh active Pending
- 2002-08-21 US US10/224,874 patent/US6734319B2/en not_active Expired - Fee Related
- 2002-08-26 TW TW91119199A patent/TW574209B/zh not_active IP Right Cessation
-
2003
- 2003-12-18 US US10/739,710 patent/US6914149B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5221798A (en) * | 1988-12-30 | 1993-06-22 | Amoco Corporation | Changing the regiopurity of mixtures containing 4,4'-disubstituted diphenyl carbonates |
EP0790231A1 (de) * | 1996-02-13 | 1997-08-20 | Bayer Ag | Verfahren zur extraktiven Abtrennung von Diarylcarbonaten und den zugrundeliegenden aromatischen Hydroxyverbindungen aus Reaktionslösungen |
JP2001288148A (ja) * | 2000-04-07 | 2001-10-16 | Teijin Ltd | 芳香族カーボネートの製造方法 |
JP2001288149A (ja) * | 2000-04-07 | 2001-10-16 | Teijin Ltd | ジアリールカーボネートの分離回収方法 |
Non-Patent Citations (1)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 02 2 April 2002 (2002-04-02) * |
Also Published As
Publication number | Publication date |
---|---|
DE10141829A1 (de) | 2003-03-20 |
US6914149B2 (en) | 2005-07-05 |
JP2005501117A (ja) | 2005-01-13 |
US20030109738A1 (en) | 2003-06-12 |
KR20040041587A (ko) | 2004-05-17 |
US6734319B2 (en) | 2004-05-11 |
EP1425259A1 (de) | 2004-06-09 |
US20040127736A1 (en) | 2004-07-01 |
CN1549807A (zh) | 2004-11-24 |
TW574209B (en) | 2004-02-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0807619B1 (de) | Verfahren zur Herstellung von Diarylcarbonaten | |
EP0667336B1 (de) | Verfahren zur kontinuierlichen Herstellung von Diarylcarbonaten | |
DE60010929T2 (de) | Katalysatorcomposition und verfahren zur herstellung von diarylcarbonaten unter anwendung von biphosphinen | |
DE19614062A1 (de) | Verfahren zur kontinuierlichen Herstellung von Diarylcarbonaten | |
DE19523390A1 (de) | Verfahren zur Herstellung von Diarylcarbonaten | |
DE10332697A1 (de) | Methode zur Abtrennung von metallischen Katalysatorbestandteilen aus Reaktionsmischungen der Herstellung aromatischer Carbonate | |
WO2003018528A1 (de) | Abtrennung von verunreinigungen und/oder wertstoffen aus diarylcarbonathaltigen lösungen durch lösungskristallisation | |
EP0801053B1 (de) | Rückgewinnung von Katalysatorsystemen aus diarylcarbonathaltigen Reaktionslösungen durch Suspensionskristallisation | |
EP1140779B1 (de) | Verfahren zur herstellung von diarylcarbonaten | |
DE10196977T5 (de) | Verfahren und Katalysatorsystem zur Herstellung von aromatischen Carbonaten | |
EP3140279B1 (de) | Verfahren zur herstellung von diarylcarbonaten | |
EP1140782A1 (de) | Verfahren zur aufarbeitung von diarylcarbonathaltigen reaktionsmischungen | |
EP1140781B1 (de) | Verfahren zur aufarbeitung von diarylcarbonathaltigen reaktionsmischungen | |
EP0801052B1 (de) | Rückgewinnung von Katalysatorsystemen aus diarylcarbonathaltigen Reaktionsgemischen durch Schmelzkristallisation | |
DE10197050T5 (de) | Verfahren zur Herstellung von Diarylcarbonaten | |
EP1427693B1 (de) | Verfahren zur herstellung von diarylcarbonaten | |
EP0021211A1 (de) | Verfahren zur Herstellung von Dimethylcarbonat | |
DE10164143A1 (de) | Verfahren zur Auftrennung von Reaktionsgemischen und Rückführung von Quartärsalzen und Basen | |
EP1279659A2 (de) | Verfahren zur Herstellung von Diarylcarbonaten | |
DE10309954A1 (de) | Verfahren zur Herstellung eines Diarylcarbonats | |
DE10164142A1 (de) | Verfahren zur Herstellung von Quartärsalzphenolatlösungen und zur Regenerierung und Rückführung von Quartärsalzphenolatlösungen aus Reaktionsgemischen | |
DE19859289A1 (de) | Verfahren zur Herstellung von Oligocarbonaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VC VN YU ZA ZM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG AE AG AL AM AT AZ BA BB BG BR BY BZ CA CH CN CO CR CZ DE DK DM DZ EC EE ES FI GB GD GE GM HR HU ID IL IN IS JP KE KG KP KR KZ LK LR LS LT LU LV MA MD MG MK MN MX MZ NO NZ OM PH PL PT RO RU SD SE SI SK SL TJ TM TN TR TT TZ UA UG UZ VC YU ZA ZM ZW GH GM KE LS MW MZ SL SZ TZ UG ZM ZW |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2002796231 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020047002844 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2003523193 Country of ref document: JP Ref document number: 2002816900X Country of ref document: CN |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWP | Wipo information: published in national office |
Ref document number: 2002796231 Country of ref document: EP |