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

HRID 1667574
ノート
印刷プレビュー

反応式

HRID 1667574 の反応式
[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]
参加物実験手順出典と根拠反応ノート

参加物

6

反応物 5

HCID 5206SevofluraneHCID 80811,3,5-TrioxaneHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 522689Potassium FluorideHCID 6451240Aluminum(III) Chloride2 回

生成物 1

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

実験手順

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 polyacetals of higher molecular weight. 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 a 6N hydrochloric acid solution 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.

出典と根拠

ORDレコード
ord-da21dd5528d94ad1b1efa67563061a0b
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044247B2

反応ノート

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