WO1996033965A1 - Procede de production d'acide acetique - Google Patents
Procede de production d'acide acetique Download PDFInfo
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- WO1996033965A1 WO1996033965A1 PCT/JP1996/001087 JP9601087W WO9633965A1 WO 1996033965 A1 WO1996033965 A1 WO 1996033965A1 JP 9601087 W JP9601087 W JP 9601087W WO 9633965 A1 WO9633965 A1 WO 9633965A1
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- distillation column
- acetic acid
- water
- liquid
- circulating
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- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
Definitions
- the present invention relates to a novel method for producing a diacid which is formed by the carbonylation of at least one selected from methanol, methyl acetate and dimethyl ether in the presence of a Group 8 metal-containing catalyst. More specifically, the present invention is directed to the production of acetic acid formed by a rhodium-catalyzed carbonylation process, and while significantly reducing the energy required for purification, an organic iodine compound and a terpionyl compound which are impurities in the product. The present invention relates to a novel method for producing high-purity acetic acid with reduced acetic acid.
- Acetic acid is most commonly used as a raw material for acetic esters, acetic anhydride, vinyl acetate, and terephthalic acid. It is a basic compound required for many industries, including the molecular and chemical industries.
- the crude acetic acid product has the following continuous 3 It is purified in two distillation steps. That is, (1) a low-boiling component separation column which separates the low-boiling component at the top and the high-boiling component at the bottom from the crude acetic acid in the sidestream of the column in order to circulate the component to the strong luponylation reactor; A dehydration tower for separating water from the sidestream crude acetic acid and circulating the separated water to the carbonylation reactor.
- a de-boiling tower for separating by-product propionic acid from dry acetic acid. In this type of process, the water concentration in the reactor is 14 to 15 wt%, which is relatively high, and the amount of by-products of probionic acid is large. Need.
- the impurities contained in the acetic acid thus obtained are, specifically, a carbonyl compound such as acetoaldehyde, crotonaldehyde and 2-ethylcrotonaldehyde and an iodine compound such as hexyl iodide. It is also known (Japanese Patent Laid-Open No. 1-121548, Japanese Patent Publication No. Hei 5-21031).
- carbonyl compounds such as acetoaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde are known as permanganic acid-substituted substances R test (permanganate thyme), which is a very small amount of permeate in sulfuric acid.
- R test permanganate thyme
- the analytical value of the quality poverty test which determines the amount of impurities present, is deteriorated (Japanese Patent Laid-Open No. 111548/1999). Many studies have been made to remove these trace impurities in the production of acetic acid by methanol carbonylation.
- the acetoaldehyde is concentrated by distillation, extraction, and reaction from the liquid in which the acetoaldehyde is concentrated in the process.
- a method in which the concentration of trace impurities in the product acid is reduced by removing the aldehyde Japanese Patent Application Laid-Open No. Hei 4-2646843.
- these patents do not mention anything in terms of simplifying the refining process and reducing refining energy.
- a serious problem occurs such that by-product ditolyl accumulates in the carbonylation reaction step accompanying the conversion reaction of aldehyde to oxime.
- the present invention relates to a method for producing acetic acid by carbonylating at least one selected from methanol, methyl peroxidate and dimethyl ether, wherein the acetic acid production is simplified while simplifying the purification process and reducing the purification energy.
- a method to efficiently reduce the concentration of carbonyl compounds such as brobionic acid, acetoaldehyde, crotonaldehyde and 2-ethylcrotonaldehyde and the organic iodine compounds such as hexyl iodide contained as impurities. provide.
- the inventors of the present invention have found that in the process of producing a sulphonic acid by methanol carbonylation, a carponyl compound such as propionic acid, acetoaldehyde, croton aldehyde, 2-ethyl chloro ton aldehyde and an organic iodine compound such as hexyl iodide are by-produced.
- a carponyl compound such as propionic acid, acetoaldehyde, croton aldehyde, 2-ethyl chloro ton aldehyde and an organic iodine compound such as hexyl iodide are by-produced.
- carbonyl compounds such as croton aldehyde and 2-ethyl croton aldehyde, and organic iodine such as hexyl iodide, among these by-products, are obtained. Attention was paid to the fact that compound by-products increased
- the present inventors have found that the water concentration in the carbonylation reaction solution is reduced, or the diluting rate of methyl sulphate in the reaction solution is increased, and the liquid separation property in the decanter at the top of the first distillation column is deteriorated.
- the present invention provides a method for continuously reacting one or more selected from methanol, methyl acetate and dimethyl ether with carbon monoxide in the presence of a Group 8 metal-containing catalyst, methyl iodide and water,
- An object of the present invention is to provide a method for producing drunk acid, which comprises maintaining a separated state of a decanter at the top of a tower.
- concentration mixed into a product can be reduced under the conditions which reduced the water density
- the group 8 metal-containing catalyst used in the present invention includes compounds such as rhodium, iridium, ruthenium, osmium, cobalt, and nickel.
- the catalyst can be used in any suitable form that can be dissolved under the reaction conditions or converted to a soluble form.
- the form of the rhodium catalyst may be any as long as it can form a rhodium complex in the reaction system, but non-limiting examples include RhX 3 (where X is Cl, Br or I), RhX 3 ⁇ 3H 20 (where X represents Cl, Br or I), Rh ⁇ CO ⁇ Rh (C0) X [(C «H B ) 3M] 2 ( Wherein X represents Cl, Br or I, M represents P, As or Sb), Rh (C0) 2 X [(C, H s ) 3 M] (wherein X represents Br or I, M represents P, As or Sb), HBh (C0) [ (C s H s) 3 P] 3, [Eh (C 2 H 4) 2 C1] 2, K 4 Eh 2 X 2 (Sn X 3 ) 4 (wherein, X represents Br or I) and the dime component described in JP-B-47-3334.
- the concentration of rhodium in the reaction solution is 200 to 1,000 ⁇
- Non-limiting examples of use forms of the iridium catalyst include IrX 3 (where X represents C 1, Br or I), [Ir (C0) 2 X] 2 (where X is Cl , Br or I), [Ir (C0) 2 X 2 ]-(where X represents Cl, Br or I), [Ir (CH 3 ) X 3 (C0) 2 ] — (wherein , X represents Cl, Br or I), Ir C0) 12 IrX 3 ⁇ 4H 20 (where X represents Cl, Br or I), IrX 3 ⁇ 4H 20 (where X represents Cl represents Br or I), IrX 3 ⁇ 4H 20 (where X represents Cl represents Br or I), Ir 3 (C0) 12, b Rijiumu metal, lr 2 0 3, Ir0 2 , Ir (acac) (C0) 2, Ir (acac) (C0) 3, acetic Lee Rijiumu [Ir 30 (0Ac) 6 (H 2 0
- Examples of the form of use of the ruthenium catalyst include, but are not limited to, ⁇ 3 (where X represents Cl, Br or I), HuX 3 ⁇ 3H 20 (where X represents Cl, Br or I) ), Ruthenium euthanasia
- the concentration of ruthenium in the reaction solution is 500 to 4,000 ppm, preferably 2,000 to 3,000 ⁇ .
- Examples of the use form of the osmium catalyst include, but are not limited to, OsX 3 (where X represents Cl, Br or I), 0sX 3 ⁇ 3H 20 (where X represents Cl, Br or I) ), Osmium metal, osmium tetroxide, trismium dodecapropionyl, pentachloro-1 / 2-dodiosmium, and mixed osmium halocarbonyl, such as tricarbodichloromethane osmium (II) dimer, and other organic osmium ⁇ Include.
- the concentration of osmium in the reaction solution is 500 to 4,000 ppm, preferably 2,000 to 3,000 ppm.
- an iodide salt is added particularly as a stabilizing agent and a co-catalyst of a rhodium catalyst under low moisture.
- This iodide salt may be any as long as it generates iodide ions in the reaction solution.
- Lil , Al, KI, fib I an alkali metal iodide salts such as Csl, Bel 2, Mgl 2, Cal 2 alkaline earth metal iodide salts such as, aluminum group metal «iodide such as BI 3, A1 I 3
- Organic iodide salts other than metal iodides may also be used.
- quaternary phosphonium iodides eg, methyl iodide adducts such as tributylphosphine and triphenylphosphine or hydrogen iodide adducts
- quaternary ammonium iodide salts eg, methyl iodide adducts such as tertiary amines, pyridines, imidazoles, imids and the like, and hydrogen iodide adducts.
- an alkali metal iodide salt such as Li 1 is preferable.
- iodide-rich i is 0.07 to 2.5 mol / liter as iodide ion in the reaction solution, and preferably 0.25 to 1.5 mol / liter as an iodide ion.
- methyl iodide is used as a catalyst promoter and is present in the reaction solution in an amount of 5 to 20% by weight, preferably 12 to 16% by weight.
- the water concentration in the reaction liquid in the present invention is 15 wt% or less, preferably 8 wt% or less, more preferably 5 wt% or less.
- Methyl acetate is present in an amount of 0.1 to 30% by weight, preferably 0.5 to 5% by weight, and the remaining main component in the reaction solution is a sulfuric acid which is both a product and a reaction solvent.
- a sulfuric acid which is both a product and a reaction solvent.
- the typical reaction temperature for methanol carbonylation in the present invention is about 150 to 250, preferably in the temperature range of about 180 to 220 ⁇ (.
- the total reaction pressure depends on the vapor of the liquid component contained in the reactor. The pressure is controlled within the range of about 15 to 40 atm for the pressure of carbon monoxide and the partial pressure of hydrogen.
- the crude reaction liquid obtained by the force ruponylation reaction in the presence of a catalyst, a cocatalyst, a catalyst stabilizer, and a reaction accelerator is withdrawn from the reactor and introduced into a flash region.
- the flash zone is preferably maintained at a pressure less than the pressure of the reaction reaction, typically 1 to 6 atmospheres.
- the flash area is maintained at a temperature of 100-200 ⁇ (: with or without heating and cooling.
- the catalyst circulating liquid containing the catalyst component that does not evaporate in the flash region is treated as it is, or if necessary, treated with hydrogen or carbon monoxide and circulated to the carboxylation reactor
- the vapor fraction evaporated in the flash area is supplied to the first distillation column as vapor and / or liquid.
- the first distillation column can preferably be operated at approximately the same pressure as the flash zone, but it is also possible to operate at higher or lower pressures.
- the operating temperature of the first distillation column depends on the composition of the components supplied, the operating pressure, the number of stages and the flow rate.
- the water concentration in the carbonylation reaction solution is preferably lower from the viewpoint that the amount of by-probionic acid by-product and the amount of carbon dioxide produced by the shift reaction are suppressed.
- the liquid separating property in the decanter at the top of the first distillation column deteriorates, and eventually the liquid does not separate.
- the impurities flowing into the top of the first distillation column due to the water flowing to the top of the first distillation column turn into water.
- the low concentration makes it easy to mix in the crude acetic acid extracted from the side stream at or near the bottom of the first distillation column.
- a phase mainly composed of methyl iodide (hereinafter, referred to as a methyl iodide phase) and a phase mainly composed of water (hereinafter, referred to as an aqueous phase)
- the methyl iodide phase which is separated into two phases and contains many impurities, was withdrawn as a low-boiling-point circulating stream. However, after the liquid was no longer separated, part of the liquid containing impurities was converted to a reflux liquid. Since it is supplied to the first distillation column, impurities are easily mixed into the crude acetic acid.
- the present invention relates to a method for reducing the concentration of water in a carbonylation reaction solution to such an extent that the liquid separation property at the top of the first distillation column is deteriorated.
- This method is used to reduce the concentration of impurities contained in crude acetic acid extracted from the bottom stream or a side stream near the bottom, especially when the water concentration in the carbonylation reaction solution is 8% or less.
- the following method can be used as a measure S for maintaining liquid separation.
- the flow rate of the upper phase (aqueous phase) from the decanter at the top of the first distillation column is such that the added water circulates between the first and second distillation columns.
- the side stream 11 at or near the bottom of the first distillation column is increased.
- the optimum cooling temperature can be selected in the range of -40 to 60'C, preferably in the range of 20 to 40'C.
- the above-mentioned method may be used alone or a plurality of means may be combined as a means for maintaining the liquid separating property in the decanter at the top of the first distillation column. Further, the liquid separation property may be maintained by increasing the number of stages of the distillation column or increasing the flow 11 of the decanter at the top of the first distillation column.
- the concentration of methyl acetate in the liquid supplied to the top decanter of the first distillation column is reduced to 40 wt% or less.
- a low-boiling-point circulating liquid or an overhead paper taken from the top of the first distillation column or acetic acid is used in the third and, if necessary, the fourth and fifth distillation columns. Separate the methyl mixture.
- the methyl acetate mixture is returned to the reaction step, and a liquid having a reduced concentration of methyl acetate is supplied to the decanter at the top of the column to maintain a liquid separation state.
- the liquid separating property at the top of the tower can be maintained.
- a low-boiling-point circulating stream consisting of an upper phase (aqueous phase) and a lower phase (methyl iodide phase) is withdrawn, or as it is or a conventionally known method, ie, distillation, extraction, After removal of the acetate from the system by reaction, it is circulated to the reactor.
- the crude acetic acid extracted from the side stream at or near the bottom of the second distillation column may be used directly as the product acetic acid, or may be subjected to a conventionally known distillation operation or a silver-exchanged strongly acidic cation exchange if necessary.
- the present invention provides a crude acetic acid product obtained by acetic acid production by carbonylation in three continuous distillation steps: (1) a low-boiling component separation column for separating a low-boiling component at the top of the column from crude acetic acid; (2) a dehydration tower that separates water from the crude acetic acid in the front tower, (3) a method of purifying by-produced propionic acid in a deboiling tower to separate it from dry acetic acid, and the above method. It can be applied to various methods such as a method of simplifying and purifying with one or two distillation columns.
- the purification energy can be conventionally achieved while keeping the purification energy low. It is possible to obtain high-quality drunk acid which was not present.
- a catalyst circulating liquid containing a catalyst component that did not evaporate in the flash region was withdrawn from the bottom of the flash region and circulated to the carbonylation reactor using a high-pressure pump.
- a component consisting mainly of acetic acid and co-catalyst methyl iodide, methyl acetate and water was extracted and introduced into the first distillation column, where low-boiling components methyl iodide and methyl acetate were extracted.
- water was separated from acetic acid, a high boiling component.
- the first distillation column used was an 20-stage Oldshaw distillation column. The liquid at the top of the first distillation column was not separated. Of the first distillation column The distillate was circulated to the forced luponylation reactor to obtain crude acetic acid from the side stream of the first distillation column. After the carbonyl impurity contained in the crude acetic acid was derivatized with dinitrophenylhydrazine and analyzed by liquid chromatography, it was found that the crude acetic acid contained a large amount of carbonyl impurities. The amount of impurities was so large that he did not confirm.
- Different flow rates ranged from 65 to 63 parts by weight per 100 parts by weight of the mixture fed to the first distillation column. That is, the added water circulates from the first distillation column to the second distillation column without being circulated to the reactor, so that the water can be circulated from the top of the first distillation column.
- Phase aqueous phase
- the flow rate was adjusted.
- the carbonyl impurities contained in the crude acetic acid obtained from the side stream of the first distillation column in this way were quantified by liquid chromatography after derivatization with dinitrate phenylhydrazine. Hexyl iodide was analyzed by SIM-GC.
- a crude reaction solution consisting of 175 ppm of acetoaldehyde, 5 wt% of methyl iodide, 7.0 wt% of water, 15 wt% of methyl acetate, 72 wt% of acid, iridium and ruthenium (4,000 ppm converted from Irl 3 and Rul 3 ) was used. Except for using, the procedure was performed in the same manner as in Comparative Example 1, and the liquid at the top of the first distillation column (decanter temperature was 40) was not separated. The amount of crotonaldehyde in the crude acetic acid obtained from the side stream of the first distillation column was 10 ppm or more.
- the decanter temperature was cooled down to 15'C, but liquid separation did not occur, and freezing began to occur at the point of further cooling, and operation became impossible.
- the crude acetic acid obtained from the side stream of the first distillation column shown in Comparative Example 3 (when the decanter temperature was 40) was supplied to the second distillation column, and the separated liquid at the top of the second distillation column was patched.
- Water (the amount of water added as a patch is equivalent to 2 parts by weight based on 100 parts by weight of the mixture supplied to the first distillation column from the top of the flash area) and the first distillation
- the top decanter of the first distillation column is circulated and supplied to the column so that the added water is circulated from the first distillation column to the second distillation column without being circulated to the carbonylation reactor.
- the reflux amount of the upper phase (aqueous phase) was adjusted.
- the amount of crotonaldehyde in crude acetic acid obtained from the side stream of the first distillation column was 3 ppm.
- Example 4 shows that liquid separation in the decanter is performed by reducing the concentration of methyl acetate in the liquid supplied to the top of the first distillation column at the top of the decanter.
- This distillate (low boiling point circulating liquid) was supplied to a third distillation column for treatment.
- the third distillation column used was an 20-stage Older Shore distillation column. With respect to the charged amount of 100 parts by weight, 35 parts by weight of a liquid containing methyl iodide as a main component was withdrawn from the top of the column and introduced into the decane overnight. The charge stage in the third distillation column is at the center and the reflux ratio is 1 Was. The remaining 65 parts by weight of the liquid was withdrawn from the bottom of the column and supplied to the fourth distillation column.
- the fourth distillation column used was an 20-stage Older Shore distillation column.
- the extraction of the methyl acetate mixed solution from the top of the column was reduced to 26 parts by weight while maintaining the flow ratio of 1. Is 30% by weight of methyl acetate, 35% by weight of methyl iodide, and 17% by weight of water. Separation was confirmed in a decanter at an operating temperature of 40%.
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Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP53234696A JP3927237B2 (ja) | 1995-04-27 | 1996-04-22 | 酢酸の製造法 |
DE69609796T DE69609796T2 (de) | 1995-04-27 | 1996-04-22 | Verfahren zur herstellung von essigsäure |
US08/765,344 US5723660A (en) | 1995-04-24 | 1996-04-22 | Process for producing acetic acid |
EP96910221A EP0768295B1 (en) | 1995-04-27 | 1996-04-22 | Process for producing acetic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7/104027 | 1995-04-27 | ||
JP10402795 | 1995-04-27 |
Publications (1)
Publication Number | Publication Date |
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WO1996033965A1 true WO1996033965A1 (fr) | 1996-10-31 |
Family
ID=14369773
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1996/001087 WO1996033965A1 (fr) | 1995-04-24 | 1996-04-22 | Procede de production d'acide acetique |
Country Status (9)
Country | Link |
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US (1) | US5723660A (ja) |
EP (1) | EP0768295B1 (ja) |
JP (1) | JP3927237B2 (ja) |
KR (1) | KR100403367B1 (ja) |
CN (3) | CN1067372C (ja) |
DE (1) | DE69609796T2 (ja) |
MY (1) | MY112751A (ja) |
TW (1) | TW339330B (ja) |
WO (1) | WO1996033965A1 (ja) |
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JP2000053609A (ja) * | 1998-07-29 | 2000-02-22 | Bp Chem Internatl Ltd | 酢酸の製造方法 |
JP2000086573A (ja) * | 1998-09-08 | 2000-03-28 | Bp Chem Internatl Ltd | カルボニル化方法 |
US6140535A (en) * | 1996-12-19 | 2000-10-31 | Bp Chemicals Limited | Iridium-catalyzed carbonylation process for the production of acetic acid |
KR100580075B1 (ko) * | 2002-12-10 | 2006-05-16 | 주식회사 엘지화학 | 이소부티릭산의 정제방법 |
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US10265639B2 (en) | 2016-07-07 | 2019-04-23 | Daicel Corporation | Process for producing acetic acid |
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WO2023225077A1 (en) | 2022-05-19 | 2023-11-23 | Lyondellbasell Acetyls, Llc | Methods for improved control of glacial acetic acid processes |
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- 1996-04-22 CN CN03145105.5A patent/CN1198781C/zh not_active Expired - Lifetime
- 1996-04-22 DE DE69609796T patent/DE69609796T2/de not_active Expired - Lifetime
- 1996-04-22 KR KR1019960707432A patent/KR100403367B1/ko not_active IP Right Cessation
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JP2010106045A (ja) * | 1998-07-29 | 2010-05-13 | Bp Chem Internatl Ltd | 酢酸の製造方法 |
JP2000053609A (ja) * | 1998-07-29 | 2000-02-22 | Bp Chem Internatl Ltd | 酢酸の製造方法 |
JP2000086573A (ja) * | 1998-09-08 | 2000-03-28 | Bp Chem Internatl Ltd | カルボニル化方法 |
KR100580075B1 (ko) * | 2002-12-10 | 2006-05-16 | 주식회사 엘지화학 | 이소부티릭산의 정제방법 |
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Also Published As
Publication number | Publication date |
---|---|
CN1136182C (zh) | 2004-01-28 |
CN1152301A (zh) | 1997-06-18 |
CN1473813A (zh) | 2004-02-11 |
EP0768295B1 (en) | 2000-08-16 |
EP0768295A1 (en) | 1997-04-16 |
EP0768295A4 (en) | 1997-07-16 |
KR100403367B1 (ko) | 2004-03-26 |
DE69609796T2 (de) | 2000-12-28 |
JP3927237B2 (ja) | 2007-06-06 |
CN1336360A (zh) | 2002-02-20 |
MY112751A (en) | 2001-08-30 |
CN1067372C (zh) | 2001-06-20 |
US5723660A (en) | 1998-03-03 |
TW339330B (en) | 1998-09-01 |
CN1198781C (zh) | 2005-04-27 |
DE69609796D1 (de) | 2000-09-21 |
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