Oxygen → Dibutyl Oxalate

HRID 1415493

Reaktionsgleichung

Reaktionsgleichung von HRID 1415493
C(N(CC)CC)C.S([O-])([O-])(=O)=O.C([NH+](CC)CC)C.C([NH+](CC)CC)C.C([O:31][C:32]1([O:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:37]CCCC1)CCC.[C:43]1(=[O:49])CC[CH2:46][CH2:45][CH2:44]1.[O:50]=O>[Pd](I)I.S([O-])([O-])(=O)=O.[Cu+2].[I-].[Li+].C(O)CCC>[C:32]([O:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:31])[C:37]([O:49][CH2:43][CH2:44][CH2:45][CH3:46])=[O:50]

Komponenten

10

Edukt 5

HCID 977OxygenHCID 7967Cyclohexanone2×HCID 8471TriethylamineHCID 2437181,1-DibutoxycyclohexaneHCID 23048603Triathylammoniumsulfat

Produkt 1

HCID 16306Dibutyl OxalateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24462Copper SulfateKatalysatorHCID 66321Lithium iodideKatalysatorHCID 424947Palladium diiodideKatalysatorHCID 2631-ButanolLösungsmittel3×

Versuchsvorschrift

The following materials were charged to the autoclave: a solution of 0.19 g. lithium iodide (1.41 mmoles), 2.34 g. triethylamine (23.0 mmoles), 6.96 g. triethylammonium sulfate (23.0 mmoles), 50 ml n-butanol (0.546 mole), and 61.7 g. of a mixture of 70.6 weight percent cyclohexanone di-n-butyl ketal (0.191 mole), 8.4 weight percent cyclohexanone, and 19.6 weight percent n-butanol (0.163 mole). The charged solids were 0.25 g. palladium (II) iodide (0.69 mmole) and 3.70 g. anhydrous copper (II) sulfate (23.0 mmoles). The reaction temperature was 100° C. The initial pressure at reaction temperature was 1500 psi. 100 psi oxygen was charged followed by 200 psi CO. An exotherm and pressure drop were noted. The oxygen/CO cycle was repeated seven more times. A total of 1870 psi pressure drop was observed during a reaction time of approximately 4.1 hours. The total pressure varied between 1500 and 2190 psi. According to gas-liquid chromatographic analysis, cyclohexanone and n-butanol were present while all of the ketal was consumed. Di-n-butyl oxalate (27.3 g.; 98 percent; 0.132 mole) was isolated by distillation and identified by spectroscopic analysis. Di-n-butyl carbonate was detected in the distillate.

Aufarbeitung

  1. additionThe following materials were charged to the autoclave
  2. customwas 100° C
  3. customThe initial pressure at reaction temperature
  4. customwas observed during a reaction time of approximately 4.1 hours
  5. customwas consumed

Quellen und Nachweise

ORD-Eintrag
ord-b033811091904c4691eef3cca25d82f4
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04005131

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