CN1172076A - Method for reducing chemical oxygen consumption of acidified sewage of cyclohexane oxidation waste alkali liquor - Google Patents
Method for reducing chemical oxygen consumption of acidified sewage of cyclohexane oxidation waste alkali liquor Download PDFInfo
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- CN1172076A CN1172076A CN 96118281 CN96118281A CN1172076A CN 1172076 A CN1172076 A CN 1172076A CN 96118281 CN96118281 CN 96118281 CN 96118281 A CN96118281 A CN 96118281A CN 1172076 A CN1172076 A CN 1172076A
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- sewage
- acidifying
- extraction
- value
- cod
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- 239000010865 sewage Substances 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 25
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000002699 waste material Substances 0.000 title claims abstract description 17
- 230000003647 oxidation Effects 0.000 title claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 13
- 239000003513 alkali Substances 0.000 title claims abstract description 12
- 230000036284 oxygen consumption Effects 0.000 title description 2
- 239000000126 substance Substances 0.000 title description 2
- 238000000605 extraction Methods 0.000 claims abstract description 36
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 17
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 230000001590 oxidative effect Effects 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000000284 extract Substances 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002576 ketones Chemical class 0.000 abstract description 4
- 238000000638 solvent extraction Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 238000004821 distillation Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007520 diprotic acids Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 150000007518 monoprotic acids Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RDNVHQZCLORQEI-UHFFFAOYSA-N OS(O)(=O)=O.C1CCCCC1 Chemical compound OS(O)(=O)=O.C1CCCCC1 RDNVHQZCLORQEI-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GKRALBJDXHXFNB-UHFFFAOYSA-N butoxycyclohexane Chemical compound CCCCOC1CCCCC1 GKRALBJDXHXFNB-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- -1 lactone compound Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for reducing COD value of acidified sewage of cyclohexane oxidation waste alkali liquor, which is characterized in that cyclohexanone, cyclohexanol or ketone alcohol product mainly containing cyclohexanone and cyclohexanol generated in the cyclohexane oxidation process is adopted to extract and/or countercurrent multistage extract the acidified sewage, the content of inorganic salt in the acidified sewage is kept between 20 and 30 percent during extraction, the pH value of the sewage is kept between 1 and 3, the temperature is controlled between 40 and 60 ℃, the volume ratio of the sewage to a solvent is 1: 0.2 to 0.8, the solvent phase after extraction is distilled to recover the solvent to obtain an organic acid mixture, the COD value of the acidified sewage can be reduced to be below 15000mg/l after solvent extraction treatment, and the COD removal rate can reach more than 80 percent.
Description
The present invention relates to a kind of method that reduces the acidifying COD of sewage value of cyclohexane oxidizing waste alkali liquor.
Prepare in the pimelinketone process at cyclohexane oxidation, some hexanaphthene generation deep oxidation side reaction, produced by product based on carboxylic acid, with in the NaOH aqueous solution and the organic acid in the oxidation liquid, in the saponification oxidation liquid organic acid acetic and one waste liquid of obtaining is called cyclohexane oxidizing waste alkali liquor or saponification waste lye.It is a kind of brown thick liquid, the COD value is up to 500000-800000mg/l, its stereoplasm thing content is 20-50%, is mainly NaOH, carbon organic monoprotic acid, diprotic acid, alcohol acid and dehydroamino acid sodium salt thereof and a small amount of low mass molecule alcohol, ketone, lactone compound below six.Adopt hexanaphthene liquid phase non-catalyst oxidation technology, a kind of typical cyclohexane oxidizing waste alkali liquor is composed as follows:
The composition weight percentage, %
NaOH 17.46 diprotic acid (are mainly pentanedioic acid, hexanodioic acid etc.) 1.36 butyric acid, 1.8 valeric acids, 4.34 caproic acids, 3.56 butyrolactone, 2.65 cyclopentanone, 0.84 other low molecular acid, ketone, ester 2.35 various high boiling point dehydroamino acids, alcohol acid and ester class 13.17 water 52.88 thereof
At present, the domestic and international burning method that adopts is handled above-mentioned waste lye morely, and burning method moves can eliminate its pollution to environment when better once, still, has burnt considerable useful resources, deficiency in economic performance.In order to effectively utilize above-mentioned resource, can use inorganic acid (as sulfuric acid cyclohexane oxidizing waste alkali liquor, nitric acid, hydrochloric acid) neutralization, under salting out, obtain the two-phase product, upper oil phase is further separated utilization, lower floor's water is that the crystallization of acidifying sewage obtains inorganic salt, as sodium sulfate, but handle with this method dewater in the acidifying sewage that obtains and inorganic salt outside, also contain a certain amount of organism, COD of sewage is generally 60000-150000mg/l, the sewage color is pale yellow to orange, and its organism composition is mainly the diprotic acid of carbon below six, alcohol acid, water-soluble condensation acid and a small amount of monoprotic acid and ketone, ester etc.If above-mentioned acidifying sewage is not further handled, therefrom the inorganic salt quality of Hui Shouing is with very poor, and final COD value of waste water of discharging is also very high.To the processing of this acidifying sewage can adopt solvent extraction wherein organism and the COD of sewage value reduced as much as possible.
The saltcake hydromining that in the clear 47-35412 of Japan's special permission communique cyclohexane oxidizing waste alkali liquor is obtained behind sulfuric acid acidation extracts to reclaim hexanodioic acid wherein with hexone, but using this method to handle back COD of sewage value still has more than the 30000mg/l, and general pimelinketone made 5 families, the methyl iso-butyl ketone (MIBK) supply is also inconvenient, the lightweight oil that produces in the report employing cyclohexane oxidation process is also arranged, and (lightweight oil the typical case form and content: hexanaphthene 3%, pimelinketone 12%, primary isoamyl alcohol 5%, Pentyl alcohol 30%, epoxy cyclohexane 30%) extracts above-mentioned acidifying sewage as extraction agent, but lightweight oil is formed complicated, the boiling range wide ranges, effect of extracting reclaims product quality with extraction and all is restricted.
The object of the invention is lain in is providing a kind of raw material to be easy to get, and the acidifying sewage extracting process that extraction efficiency is high with contained various organism in the acidifying sewage that reclaims cyclohexane oxidizing waste alkali liquor, reduces this acidifying COD of sewage value as far as possible.
The present invention is achieved in that the H of cyclohexane oxidizing waste alkali liquor with 40-45%
2SO
4It is 1-3 that solution is neutralized to pH value, under the non-crystallizable temperature condition of separating out of assurance sodium sulfate, leave standstill and tell upper oil phase, obtaining lower floor's water is acidifying sewage, pimelinketone, the hexalin that acidifying sewage is produced with cyclohexane oxidation and the keto-alcohol product that mainly contains pimelinketone, hexalin extracts and or counter current multi-stage extraction, extraction temperature is 40-60 ℃, sewage is 1 with the solvent volume ratio: 0.1-0.8, several times or multi-stage solvent extraction, extraction back solvent phase reclaims solvent under the underpressure distillation condition, obtaining organic acid is main extraction product.
Implement the primary product that raw material of the present invention is cyclohexane oxidation, supply is convenient.According to raw material provided by the invention and processing condition, the acidifying sewage of cyclohexane oxidizing waste alkali liquor is extracted, the extraction efficiency height, extraction back COD of sewage value can be reduced to below the 15000mg/l, and the COD clearance can reach more than 80%.
Embodiment 1: hexanaphthene liquid phase non-catalyst oxidation is prepared the waste lye 1000g that produces in the Cyclohexanone Production process, with the H of concentration 45%
2SO
4It is 2 that solution is acidified to PH, consumes 45%H altogether
2SO
4Solution 567g, standing demix gets upper oil phase 255g, and lower floor's water is acidifying sewage 1312g.
Embodiment 2: the acidifying sewage 500ml by embodiment 1 described method obtains, measure its Na
2SO
4Content is 25.6%, and the COD value is 77200mg/l, and pH value is 2, extracts this acidifying sewage four times with pimelinketone (cyclohexanone content 99.8%), and the pimelinketone consumption of each extraction is 50ml, extraction temperature 42-45 ℃.After four extractions, acidifying COD of sewage value is reduced to 16830mg/l, COD clearance 78.2%, and extraction back sewage color is limpid colourless.At vacuum 92mmHg, pimelinketone 197ml is reclaimed in 120 ℃ of distillations down of temperature altogether, obtains distillation residue 19.7g with the gained extraction solvent, and this residue is cooled to yellow paste solids, and measuring its acid number is 496.61mgKOH/g.
Embodiment 3: the acidifying sewage 500ml by embodiment 1 described method obtains, measure its Na
2SO
4Content is 24.5%, the COD value is 69400mg/l, pH value is 2, (it consists of hexalin 85-90% with the intermediates hexalin in the Cyclohexanone Production process, pimelinketone 5-10%, butyl cyclohexyl ether 1-10%), extract this acidifying sewage four times, the hexalin consumption of each extraction is 50ml, extraction temperature 44-46 ℃.After four extractions, acidifying COD of sewage value is reduced to 15300mg/l, COD clearance 77.95%, and extraction back sewage color is limpid colourless.At vacuum 107mmHg, hexalin 196ml is reclaimed in 124 ℃ of distillations down of temperature altogether, gets distillation residue 21.6g with the gained extraction solvent, and this residue is cooled to deep yellow paste solids, and measuring its acid number is 427.39mgkoh/g.
Embodiment 4: the acidifying sewage 500ml by embodiment 1 described method obtains, measure its Na
2SO
4Content is 24.3%, and the COD value is 87900mg/l, and pH value is 2, extract this acidifying sewage four times with the keto-alcohol mixture that produces in the Cyclohexanone Production process (it consists of pimelinketone 52%, hexalin 45%, other is 3% years old), the keto-alcohol amount of mixture of each extraction is 50mg, extraction temperature 44-46 ℃.After four extractions, acidifying COD of sewage value is reduced to 19450mg/l, COD clearance 77.87%, and extraction back sewage color is limpid colourless.At vacuum 520mmhg, solvent 193.5mg is reclaimed in 150 ℃ of distillations down of temperature altogether, gets distillation residue 31.3g with the gained extraction solvent, and this residue is cooled to the black dope, and measuring its acid number is 199.08mgkoh/g.
Embodiment 5: by the acidifying sewage that embodiment 1 described method obtains, measure its Na
2SO
4Content is 24.3%, and the CDD value is 87900mg/l, and pH value is 2, press embodiment 2 described methods again and with pimelinketone this acidifying sewage is extracted eight times, extract the effluent solvent volume ratio is 10: 1 at every turn, after eight extractions, the acidifying COD of sewage is reduced to 7350mg/l, and the COD clearance is 91.64%.
Embodiment 6: by the acidifying sewage that embodiment 1 described method obtains, measure its Na
2SO
4Content is 24.3%, and the COD value is 87900mg/l, and pH value is 2, presses the intermediates hexalin (it is formed with embodiment 3) in the embodiment 2 described methods usefulness Cyclohexanone Production processes again.To this acidifying sewage extraction eight times, extract the effluent solvent volume ratio is 10: 1 at every turn, and after eight extractions, the acidifying COD of sewage is reduced to 9500mg/l, and it is 89.19% that COD removes rate.
Embodiment 7: by the acidifying sewage that embodiment 1 described method obtains, measure its Na
2SO
4Content is 24.3%, and the COD value is 87900mg/l, and pH value is 2.Adopt the adverse current method to extract to this acidifying sewage, the every wheel extracts four times, each effluent solvent volume ratio is 5: 1, but only fresh solvent is adopted in the 4th extraction, and the 3rd, two, single extraction adopts in the previous round test the 4th, three respectively, reextraction secret solvent phase, extraction solvent is the intermediates hexalin (it is formed with embodiment 3) in the Cyclohexanone Production process, extract other processing condition with embodiment 3, through four extractions, acidifying COD of sewage value is reduced to 13500mg/l, COD clearance 84.62%.
Claims (3)
1. method that reduces the acidifying COD of sewage value of cyclohexane oxidizing waste alkali liquor, it is characterized in that: with the waste lye that produces in the cyclohexane oxidation process with in the inorganic acid and the acidifying sewage that obtains of layering with pimelinketone, hexalin, or mainly contain pimelinketone or hexalin mixture extraction and or counter current multi-stage extraction reclaim the organic acid mixture, reduce the COD value of acidifying sewage.
2. want 1 described method according to right, it is characterized in that, during extraction acidifying sewage in the sewage inorganic salt content remain on 20%-30%, sewage PH value remains on 1-3, temperature is controlled at 40-60 ℃.
3. according to the described method of claim 1, when it is characterized in that extracting acidifying sewage, the volume ratio of sewage and solvent is 1: 0.2-0.8.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 96118281 CN1068299C (en) | 1996-07-25 | 1996-07-25 | Method for reducing chemical oxygen consumption of acidified sewage of cyclohexane oxidation waste alkali liquor |
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Application Number | Priority Date | Filing Date | Title |
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CN 96118281 CN1068299C (en) | 1996-07-25 | 1996-07-25 | Method for reducing chemical oxygen consumption of acidified sewage of cyclohexane oxidation waste alkali liquor |
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CN1172076A true CN1172076A (en) | 1998-02-04 |
CN1068299C CN1068299C (en) | 2001-07-11 |
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CN 96118281 Expired - Fee Related CN1068299C (en) | 1996-07-25 | 1996-07-25 | Method for reducing chemical oxygen consumption of acidified sewage of cyclohexane oxidation waste alkali liquor |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102276007A (en) * | 2010-06-12 | 2011-12-14 | 中国石油化工集团公司 | Method for treating sewage produced during cyclohexanone production by adopting extraction method |
CN103601328A (en) * | 2013-10-15 | 2014-02-26 | 内蒙古常盛制药有限公司 | Process for 6-APA or 7-ADCA production waste water recycling resource and biochemistry pretreatment |
CN107540523A (en) * | 2016-06-28 | 2018-01-05 | 中国石油化工股份有限公司 | A kind of method for reducing sodium salt content in the ketone material of crude glycol containing alkali lye |
CN111378467A (en) * | 2018-12-29 | 2020-07-07 | 中国石油天然气股份有限公司 | Method for treating cyclohexane oxidation by-products |
-
1996
- 1996-07-25 CN CN 96118281 patent/CN1068299C/en not_active Expired - Fee Related
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102276007A (en) * | 2010-06-12 | 2011-12-14 | 中国石油化工集团公司 | Method for treating sewage produced during cyclohexanone production by adopting extraction method |
CN102276007B (en) * | 2010-06-12 | 2013-04-03 | 中国石油化工集团公司 | Method for treating sewage produced during cyclohexanone production by adopting extraction method |
CN103601328A (en) * | 2013-10-15 | 2014-02-26 | 内蒙古常盛制药有限公司 | Process for 6-APA or 7-ADCA production waste water recycling resource and biochemistry pretreatment |
CN103601328B (en) * | 2013-10-15 | 2015-02-18 | 内蒙古常盛制药有限公司 | Process for 6-APA or 7-ADCA production waste water recycling resource and biochemistry pretreatment |
CN107540523A (en) * | 2016-06-28 | 2018-01-05 | 中国石油化工股份有限公司 | A kind of method for reducing sodium salt content in the ketone material of crude glycol containing alkali lye |
CN107540523B (en) * | 2016-06-28 | 2021-05-07 | 中国石油化工股份有限公司 | Method for reducing sodium salt content in crude alcohol ketone material containing alkali liquor |
CN111378467A (en) * | 2018-12-29 | 2020-07-07 | 中国石油天然气股份有限公司 | Method for treating cyclohexane oxidation by-products |
CN111378467B (en) * | 2018-12-29 | 2022-08-30 | 中国石油天然气股份有限公司 | Method for treating cyclohexane oxidation by-product |
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Publication number | Publication date |
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CN1068299C (en) | 2001-07-11 |
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