Sulfuric acid, dibutyl ester → Tri-ethyl(n-butyl)phosphonium butylsulfate

HRID 1869613

Reaktionsgleichung

Reaktionsgleichung von HRID 1869613
[CH2:1]([P:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:8]([O:12][S:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:15])=[O:14])[CH2:9][CH2:10][CH3:11]>>[CH2:8]([O:12][S:13]([O-:16])(=[O:15])=[O:14])[CH2:9][CH2:10][CH3:11].[CH2:1]([P+:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:2]

Komponenten

3

Edukt 2

HCID 12239Sulfuric acid, dibutyl esterHCID 27365Triethylphosphine

Produkt 1

HCID 86609275Tri-ethyl(n-butyl)phosphonium butylsulfateAusbeute 85 %

Versuchsvorschrift

Triethylphosphine (7.2 g, 99%, 0.06 mol) was added dropwise to a 125 mL flask containing 12.6 (99%, 0.06 mol) di-n-butylsulfate at 80° C. under nitrogen and with stirring over a period of 75 minutes. The liquid was stirred at 140° C. for an additional 3.5 hours. The liquid was cooled, moved to a rotary evaporator and dried at 125° C./5 mm Hg for 6 hours. The product (16.73 g, yield 85%) was a wax-like solid at room temperature (m.p. from DSC measurement: 40.0° C.). 1H-NMR (CDCl3, 300.13 MHz, δ): 3.98 (t, 2H, CH3CH2CH2—CH2—O—), 2.34 (m, 8H, 3×CH3—CH2P+ and CH3CH2CH2—CH2P+), 1.54 (m, 8H, CH3—CH2CH2—CH2O— and CH3—CH2CH2—CH2P+), 1.25 (m, 3×CH3—CH2P+), 0.91 (m, 6H, CH3CH2CH2—CH2O— and CH3CH2CH2—CH2P+). 31P-NMR (CDCl31 81.015 MHz, δ): 38.88 (s, P+).

Aufarbeitung

  1. stirringThe liquid was stirred at 140° C. for an additional 3.5 hours
  2. temperatureThe liquid was cooled
  3. custommoved to a rotary evaporator
  4. customdried at 125° C./5 mm Hg for 6 hours

Quellen und Nachweise

ORD-Eintrag
ord-98b62acb5a7b470da9b91d33464d3993
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638636B2

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