JPS6113691B2 - - Google Patents
Info
- Publication number
- JPS6113691B2 JPS6113691B2 JP12805183A JP12805183A JPS6113691B2 JP S6113691 B2 JPS6113691 B2 JP S6113691B2 JP 12805183 A JP12805183 A JP 12805183A JP 12805183 A JP12805183 A JP 12805183A JP S6113691 B2 JPS6113691 B2 JP S6113691B2
- Authority
- JP
- Japan
- Prior art keywords
- bismuth
- catalyst
- malachite
- copper
- carbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229910052797 bismuth Inorganic materials 0.000 claims description 50
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 47
- 239000002245 particle Substances 0.000 claims description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 30
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000010949 copper Substances 0.000 claims description 17
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 229910052802 copper Inorganic materials 0.000 claims description 14
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 claims description 8
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 59
- 241000907663 Siproeta stelenes Species 0.000 description 36
- 229940116318 copper carbonate Drugs 0.000 description 24
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 24
- 238000000034 method Methods 0.000 description 16
- 238000010899 nucleation Methods 0.000 description 14
- 230000006911 nucleation Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 235000019256 formaldehyde Nutrition 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000000476 acetylides Chemical class 0.000 description 4
- KBZSNAZVDVIXKL-UHFFFAOYSA-L bismuth copper carbonate Chemical compound [Cu+2].[Bi+3].[O-]C([O-])=O KBZSNAZVDVIXKL-UHFFFAOYSA-L 0.000 description 4
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NPKGQBIUYHHPOT-UHFFFAOYSA-N [Cu+2].[C-]#[C-] Chemical compound [Cu+2].[C-]#[C-] NPKGQBIUYHHPOT-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001621 bismuth Chemical class 0.000 description 3
- -1 butyne diol Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- KDKYADYSIPSCCQ-UHFFFAOYSA-N ethyl acetylene Natural products CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910000416 bismuth oxide Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- CBACFHTXHGHTMH-UHFFFAOYSA-N 2-piperidin-1-ylethyl 2-phenyl-2-piperidin-1-ylacetate;dihydrochloride Chemical compound Cl.Cl.C1CCCCN1C(C=1C=CC=CC=1)C(=O)OCCN1CCCCC1 CBACFHTXHGHTMH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229910000014 Bismuth subcarbonate Inorganic materials 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 239000012691 Cu precursor Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GACUIHAEKGVEIC-UHFFFAOYSA-L [Bi+2]=O.C([O-])([O-])=O Chemical compound [Bi+2]=O.C([O-])([O-])=O GACUIHAEKGVEIC-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- MGLUJXPJRXTKJM-UHFFFAOYSA-L bismuth subcarbonate Chemical compound O=[Bi]OC(=O)O[Bi]=O MGLUJXPJRXTKJM-UHFFFAOYSA-L 0.000 description 1
- 229940036358 bismuth subcarbonate Drugs 0.000 description 1
- YNCZNSWQAGQAJY-UHFFFAOYSA-N but-2-yne-1,1-diol Chemical compound CC#CC(O)O YNCZNSWQAGQAJY-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000005323 carbonate salts Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- DMRJVKOYZFHZJH-UHFFFAOYSA-L copper;hydrogen carbonate;hydroxide Chemical compound [OH-].[Cu+2].OC([O-])=O DMRJVKOYZFHZJH-UHFFFAOYSA-L 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012213 gelatinous substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2286—Alkynes, e.g. acetylides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G3/00—Compounds of copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond
- C07C33/044—Alkynediols
- C07C33/046—Butynediols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44547674A | 1974-02-25 | 1974-02-25 | |
| US445476 | 1995-05-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5931720A JPS5931720A (ja) | 1984-02-20 |
| JPS6113691B2 true JPS6113691B2 (nl) | 1986-04-15 |
Family
ID=23769056
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2250175A Expired JPS594380B2 (ja) | 1974-02-25 | 1975-02-25 | 塩基性炭酸銅の結晶性粒子集塊の製法 |
| JP12805183A Granted JPS5931720A (ja) | 1974-02-25 | 1983-07-15 | １，４−ブチンジオ−ルの製造法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2250175A Expired JPS594380B2 (ja) | 1974-02-25 | 1975-02-25 | 塩基性炭酸銅の結晶性粒子集塊の製法 |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS594380B2 (nl) |
| BE (1) | BE825446A (nl) |
| DE (2) | DE2560545C2 (nl) |
| FR (2) | FR2264034B1 (nl) |
| GB (2) | GB1501459A (nl) |
| IT (1) | IT1033129B (nl) |
| NL (1) | NL183087C (nl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1096134A (en) * | 1976-08-05 | 1981-02-24 | Joseph M. Fremont | Preparation of bismuth-modified spheroidal malachite |
| GB2039268B (en) | 1978-12-15 | 1983-01-19 | Exxon Research Engineering Co | Metal extraction by solid-liquid agglomerates |
| DE3417629C1 (de) * | 1984-05-12 | 1985-01-24 | Th. Goldschmidt Ag, 4300 Essen | Verfahren zur Herstellung von basischem Kupfercarbonat |
| JPS60252078A (ja) * | 1984-05-30 | 1985-12-12 | Mitsubishi Motors Corp | 車両のウインドガラス搬送位置決め装置 |
| JPH0311107Y2 (nl) * | 1986-02-21 | 1991-03-18 | ||
| JPH0447026Y2 (nl) * | 1986-03-10 | 1992-11-06 | ||
| DE102005042185A1 (de) * | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Abtrennung von polymeren Nebenprodukten aus 1,4-Butindiol |
| JP5379149B2 (ja) * | 2008-10-07 | 2013-12-25 | 日本曹達株式会社 | テトラフルオロ化合物の製造方法 |
| CN111589836B (zh) * | 2019-09-16 | 2021-10-26 | 徐光耀 | 含乙炔化物的废料处理方法 |
| CN111747439B (zh) * | 2020-07-13 | 2023-08-29 | 泰兴冶炼厂有限公司 | 一种超高纯碱式碳酸铜制备工艺 |
| CN115703647A (zh) * | 2021-08-06 | 2023-02-17 | 阮氏化工（常熟）有限公司 | 利用酸性蚀刻废液连续化生产碱式碳酸铜的方法 |
| CN114873653B (zh) * | 2022-05-11 | 2023-10-13 | 金驰能源材料有限公司 | 碱式碳酸钴及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2300969A (en) * | 1939-09-07 | 1942-11-03 | Gen Aniline & Film Corp | Production of alkinols |
| US3650985A (en) * | 1967-10-23 | 1972-03-21 | Du Pont | Ethynylation catalyst catalyst preparation and process |
-
1975
- 1975-02-12 BE BE153285A patent/BE825446A/xx not_active IP Right Cessation
- 1975-02-24 NL NL7502177A patent/NL183087C/nl not_active IP Right Cessation
- 1975-02-24 IT IT2058475A patent/IT1033129B/it active
- 1975-02-24 FR FR7505627A patent/FR2264034B1/fr not_active Expired
- 1975-02-25 DE DE19752560545 patent/DE2560545C2/de not_active Expired
- 1975-02-25 JP JP2250175A patent/JPS594380B2/ja not_active Expired
- 1975-02-25 GB GB787775A patent/GB1501459A/en not_active Expired
- 1975-02-25 DE DE19752508084 patent/DE2508084C2/de not_active Expired
- 1975-07-18 FR FR7522506A patent/FR2330647A1/fr active Granted
-
1978
- 1978-04-03 GB GB1296178A patent/GB1555297A/en not_active Expired
-
1983
- 1983-07-15 JP JP12805183A patent/JPS5931720A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE825446A (fr) | 1975-08-12 |
| FR2264034B1 (nl) | 1981-06-26 |
| JPS594380B2 (ja) | 1984-01-30 |
| JPS5931720A (ja) | 1984-02-20 |
| DE2508084C2 (de) | 1984-06-07 |
| NL7502177A (nl) | 1975-08-27 |
| JPS50119797A (nl) | 1975-09-19 |
| GB1555297A (en) | 1979-11-07 |
| GB1501459A (en) | 1978-02-15 |
| FR2330647B1 (nl) | 1981-06-26 |
| FR2264034A1 (nl) | 1975-10-10 |
| IT1033129B (it) | 1979-07-10 |
| NL183087B (nl) | 1988-02-16 |
| DE2508084A1 (de) | 1975-08-28 |
| DE2560545C2 (de) | 1986-05-07 |
| NL183087C (nl) | 1988-07-18 |
| FR2330647A1 (fr) | 1977-06-03 |
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