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Sevoflurane → Propane, 2,2'-[methylenebis(oxy)]bis[1,1,1,3,3,3-hexafluoro-

HRID 1665901
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[CH2:1](F)[O:2][CH:3]([C:8]([F:11])([F:10])[F:9])[C:4]([F:7])([F:6])[F:5].[F-].[K+].[F:15][C:16]([F:24])([F:23])[CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19].[Cl-].[Cl-].[Cl-].[Al+3].O1COCOC1>>[CH2:1]([O:22][CH:17]([C:18]([F:21])([F:20])[F:19])[C:16]([F:24])([F:23])[F:15])[O:2][CH:3]([C:8]([F:11])([F:10])[F:9])[C:4]([F:7])([F:6])[F:5]
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HCID 5206SevofluraneHCID 80811,3,5-TrioxaneHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 522689Potassium FluorideHCID 6451240Aluminum(III) Chloride2회

생성물 1

HCID 9950185Propane, 2,2'-[methylenebis(oxy)]bis[1,1,1,3,3,3-hexafluoro-

실험 절차

U.S. Pat. No. 6,100,434 describes the synthesis of sevoflurane through the preparation of sevochlorane and subsequent fluorination of this intermediate with potassium fluoride in a high molecular weight solvent. Sevochlorane is prepared from hexafluoroisopropanol, aluminum trichloride and 1,3,5-trioxane. An excess of aluminum trichloride in the reaction medium results predominantly in the formation of 2,2′-[methylenebis(oxy)]bis-(1,1,1,3,3,3-hexafluoropropane)—hereinafter denominated P1. The reaction is interrupted by addition of a 6N HCl solution to decompose the gel of hydroxydichloroaluminate. The authors relate that the isolated product contained 95% sevochlorane, <5% of P1 and <1% of higher molecular weight polyacetals. The crude yield described was 87%. Among the disadvantages of this process is the fact that large quantities of aluminum trichloride must be handled, which is a highly hygroscopic solid and whose reaction with atmospheric humidity or with residual water present tends to be violent. The fact that this reagent easily reacts with water, resulting in the formation of acidic gasses, causes a reduction in its content, compromising considerably the yield of the reaction and the purity of the isolated product. The addition of 6N hydrochloric acid to interrupt the reaction is an additional disadvantage of the process, violently elevating the reaction temperature, resulting in partial product loss by decomposition, volatilization and polymerization. Finally, this reaction generates as a residue, an aqueous phase containing hydroxyaluminates that require incineration for disposal, incurring additional costs.

출처 및 근거

ORD 기록
ord-03e7f44a9ba84dfa866af2fed464f84d
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08039678B2

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