JP2008500395A - N−(ホスホノメチル)グリシンの精製 - Google Patents
N−(ホスホノメチル)グリシンの精製 Download PDFInfo
- Publication number
- JP2008500395A JP2008500395A JP2007527533A JP2007527533A JP2008500395A JP 2008500395 A JP2008500395 A JP 2008500395A JP 2007527533 A JP2007527533 A JP 2007527533A JP 2007527533 A JP2007527533 A JP 2007527533A JP 2008500395 A JP2008500395 A JP 2008500395A
- Authority
- JP
- Japan
- Prior art keywords
- pmg
- product
- weight percent
- purified
- acid
- 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.)
- Granted
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000746 purification Methods 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000005562 Glyphosate Substances 0.000 claims abstract description 14
- 229940097068 glyphosate Drugs 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001728 nano-filtration Methods 0.000 claims abstract description 7
- 239000002244 precipitate Substances 0.000 claims abstract description 6
- 239000012528 membrane Substances 0.000 claims abstract description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000004471 Glycine Substances 0.000 claims description 11
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 glyphosate triester Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 2
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- SGVDYFNFBJGOHB-UHFFFAOYSA-N 2-[methyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C)CP(O)(O)=O SGVDYFNFBJGOHB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- C07F9/02—Phosphorus compounds
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
-
- 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
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
1)PMGを含む物質を塩基の存在下で水に溶解または懸濁して、水性塩基におけるPMG塩を含む組成物を製造する工程;
2)前記組成物を、PMG塩が中和されるように酸と接触させて、PMGの沈殿を形成させる工程;および
3)PMGの沈殿を単離する工程
を含み、
ただし、工程1)の組成物は、ナノろ過膜を使用して濃縮またはろ過されない。
Claims (10)
- グリホサート(PMG)を精製するための方法であって、
1)PMGを含む物質を塩基の存在下で水に溶解または懸濁して、水性塩基におけるPMG塩を含む組成物を製造する工程;
2)前記組成物を、PMG塩が中和されるように酸と接触させて、PMGの沈殿を形成させる工程;および
3)PMGの沈殿を単離する工程
を含み、
ただし、工程1)の組成物は、ナノろ過膜を使用して濃縮またはろ過されない、方法。 - 塩基の量が、PMG物質のモル数に基づいて0.5モル当量から1.2モル当量である、請求項1に記載の方法。
- 中和のために利用される酸の量が、PMG物質のモル数に基づいて0.5モル当量から1.3モル当量である、請求項1に記載の方法。
- 塩基が水酸化ナトリウムである、請求項1に記載の方法。
- 酸が塩酸である、請求項1に記載の方法。
- 精製されたPMG生成物が、精製されたPMG生成物の総重量に基づいて0.1重量パーセント未満のグリシンを含有する、請求項1に記載の方法。
- 精製されたPMG生成物が、精製されたPMG生成物の総重量に基づいて0.1重量パーセント未満のMePMGを含有する、請求項1に記載の方法。
- 精製されたPMG生成物が、精製されたPMG生成物の総重量に基づいて0.2重量パーセント未満のグリホシンを含有する、請求項1に記載の方法。
- 工程2)の生成物が0.9から2.9のpHを有する、請求項1に記載の方法。
- 工程2)の生成物が0.9から1.25のpHを有する、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57325504P | 2004-05-21 | 2004-05-21 | |
US60/573,255 | 2004-05-21 | ||
PCT/US2005/017989 WO2005113567A1 (en) | 2004-05-21 | 2005-05-20 | Purification of n-(phosphonomethyl)glycine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008500395A true JP2008500395A (ja) | 2008-01-10 |
JP4896881B2 JP4896881B2 (ja) | 2012-03-14 |
Family
ID=35134799
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007527533A Expired - Fee Related JP4896881B2 (ja) | 2004-05-21 | 2005-05-20 | N−(ホスホノメチル)グリシンの精製 |
Country Status (21)
Country | Link |
---|---|
US (1) | US7683207B2 (ja) |
EP (1) | EP1756127B1 (ja) |
JP (1) | JP4896881B2 (ja) |
KR (1) | KR20070012828A (ja) |
CN (1) | CN1953986B (ja) |
AT (1) | ATE417854T1 (ja) |
AU (1) | AU2005245973B2 (ja) |
BR (1) | BRPI0511434A (ja) |
CA (1) | CA2564397A1 (ja) |
DE (1) | DE602005011797D1 (ja) |
DK (1) | DK1756127T3 (ja) |
ES (1) | ES2317251T3 (ja) |
IL (1) | IL178994A (ja) |
MX (1) | MXPA06013372A (ja) |
NZ (1) | NZ550781A (ja) |
PL (1) | PL1756127T3 (ja) |
RU (1) | RU2369611C2 (ja) |
TW (1) | TW200538459A (ja) |
UA (1) | UA84345C2 (ja) |
WO (1) | WO2005113567A1 (ja) |
ZA (1) | ZA200609230B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8026389B2 (en) * | 2006-12-15 | 2011-09-27 | Ricardo Amaral Remer | Solid and water-soluble active ingredient and herbicide formulation, production process therefor, and process for controlling weeds |
CN101434620B (zh) * | 2008-12-18 | 2011-11-09 | 杭州天创净水设备有限公司 | Ida法草甘膦母液取粉系统及取粉工艺 |
CN104151355A (zh) * | 2014-08-06 | 2014-11-19 | 四川省乐山市福华通达农药科技有限公司 | 一种甘氨酸法制备草甘膦的脏粉处理工艺 |
CN105692960A (zh) * | 2016-03-04 | 2016-06-22 | 安徽国星生物化学有限公司 | 一种草甘膦母液的处理方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS611695A (ja) * | 1984-06-04 | 1986-01-07 | ストウフアー ケミカル カンパニー | N‐ホスホノメチルグリシンの製造方法 |
JPH0386892A (ja) * | 1989-08-17 | 1991-04-11 | Monsanto Co | N―ホスホノメチルグリシンの精製法 |
JPH08134088A (ja) * | 1994-11-09 | 1996-05-28 | Showa Denko Kk | N−ホスホノメチルグリシンの単離方法 |
JP2004535438A (ja) * | 2001-06-22 | 2004-11-25 | ビーエーエスエフ アクチェンゲゼルシャフト | N−ホスホノメチルグリシンの回収方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
GB1436843A (en) | 1972-07-21 | 1976-05-26 | Ici Ltd | Preparation of n-phosphonomethyl-glycine |
CH647528A5 (fr) * | 1978-10-27 | 1985-01-31 | Bcap Biolog Chem Act Pat | Procede pour la preparation de n-phosphonomethylglycine. |
EP0806428B1 (en) * | 1994-11-09 | 2003-01-29 | Showa Denko Kabushiki Kaisha | Method for isolating N-phosphonomethylglycine |
AR027024A1 (es) * | 1999-12-23 | 2003-03-12 | Basf Ag | Procedimiento para la preparacion de n-fosfonometilglicina |
AR039201A1 (es) * | 2003-03-28 | 2005-02-09 | Atanor S A | Procedimiento para purificar soluciones de glifosato mediante nanofiltracion |
-
2005
- 2005-04-28 TW TW094113644A patent/TW200538459A/zh unknown
- 2005-05-20 RU RU2006145439/04A patent/RU2369611C2/ru not_active IP Right Cessation
- 2005-05-20 JP JP2007527533A patent/JP4896881B2/ja not_active Expired - Fee Related
- 2005-05-20 US US11/133,739 patent/US7683207B2/en not_active Expired - Fee Related
- 2005-05-20 CA CA002564397A patent/CA2564397A1/en not_active Abandoned
- 2005-05-20 EP EP05753118A patent/EP1756127B1/en not_active Not-in-force
- 2005-05-20 NZ NZ550781A patent/NZ550781A/en not_active IP Right Cessation
- 2005-05-20 ZA ZA200609230A patent/ZA200609230B/en unknown
- 2005-05-20 BR BRPI0511434-9A patent/BRPI0511434A/pt not_active IP Right Cessation
- 2005-05-20 DK DK05753118T patent/DK1756127T3/da active
- 2005-05-20 ES ES05753118T patent/ES2317251T3/es active Active
- 2005-05-20 UA UAA200613503A patent/UA84345C2/ru unknown
- 2005-05-20 WO PCT/US2005/017989 patent/WO2005113567A1/en active Application Filing
- 2005-05-20 MX MXPA06013372A patent/MXPA06013372A/es active IP Right Grant
- 2005-05-20 DE DE602005011797T patent/DE602005011797D1/de active Active
- 2005-05-20 AU AU2005245973A patent/AU2005245973B2/en not_active Ceased
- 2005-05-20 CN CN2005800151195A patent/CN1953986B/zh not_active Expired - Fee Related
- 2005-05-20 PL PL05753118T patent/PL1756127T3/pl unknown
- 2005-05-20 AT AT05753118T patent/ATE417854T1/de active
- 2005-05-20 KR KR1020067024021A patent/KR20070012828A/ko not_active Application Discontinuation
-
2006
- 2006-11-01 IL IL178994A patent/IL178994A/en not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS611695A (ja) * | 1984-06-04 | 1986-01-07 | ストウフアー ケミカル カンパニー | N‐ホスホノメチルグリシンの製造方法 |
JPH0386892A (ja) * | 1989-08-17 | 1991-04-11 | Monsanto Co | N―ホスホノメチルグリシンの精製法 |
JPH08134088A (ja) * | 1994-11-09 | 1996-05-28 | Showa Denko Kk | N−ホスホノメチルグリシンの単離方法 |
JP2004535438A (ja) * | 2001-06-22 | 2004-11-25 | ビーエーエスエフ アクチェンゲゼルシャフト | N−ホスホノメチルグリシンの回収方法 |
Also Published As
Publication number | Publication date |
---|---|
DE602005011797D1 (de) | 2009-01-29 |
EP1756127B1 (en) | 2008-12-17 |
US20060264655A1 (en) | 2006-11-23 |
JP4896881B2 (ja) | 2012-03-14 |
PL1756127T3 (pl) | 2009-06-30 |
EP1756127A1 (en) | 2007-02-28 |
AU2005245973B2 (en) | 2010-09-16 |
CN1953986B (zh) | 2011-04-06 |
DK1756127T3 (da) | 2009-03-02 |
MXPA06013372A (es) | 2007-03-01 |
ATE417854T1 (de) | 2009-01-15 |
AU2005245973A1 (en) | 2005-12-01 |
BRPI0511434A (pt) | 2007-12-26 |
IL178994A (en) | 2010-06-16 |
ZA200609230B (en) | 2008-06-25 |
WO2005113567A1 (en) | 2005-12-01 |
IL178994A0 (en) | 2007-03-08 |
US7683207B2 (en) | 2010-03-23 |
ES2317251T3 (es) | 2009-04-16 |
RU2369611C2 (ru) | 2009-10-10 |
TW200538459A (en) | 2005-12-01 |
KR20070012828A (ko) | 2007-01-29 |
NZ550781A (en) | 2009-06-26 |
CN1953986A (zh) | 2007-04-25 |
RU2006145439A (ru) | 2008-06-27 |
UA84345C2 (en) | 2008-10-10 |
CA2564397A1 (en) | 2005-12-01 |
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