Water → Cyclohexanol

HRID 1007630Notes

Reaction equation

HRID 1007630 reaction equation
[K].[OH-].[K+].O.[CH:5]#[CH:6].[CH:7]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[CH:7]1([O:13][CH:5]=[CH2:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH:7]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 5

HCID 962WaterHCID 6326Acetylene2×HCID 7966Cyclohexanol2×HCID 14797Potassium HydroxideHCID 5462222Potassium

Product 2

HCID 7966CyclohexanolHCID 75129Cyclohexane, (ethenyloxy)-

Conditions

Temperature
159 °C

Procedure

A jet loop reactor having an internal volume of about 10.5 l and equipped with a jet nozzle fitted at the head of the reactor and an external circulation pump was charged with about 10.5 kg of a mixture of 5% by weight of potassium cyclohexoxide in cyclohexanol, which was prepared by reaction of cyclohexanol with potassium hydroxide and subsequent distillative removal of the water formed in the reaction. After heating to 159° C., the system was pressurized with ethyne to 2.0 MPa absolute. The reaction mixture was circulated through the jet nozzle by means of a circulation pump and the reacted ethyne was replaced while the total pressure was held constant. Any excess product was removed by a pressure control. The reactor was operated in the absence of a continuous gas phase. After the uptake of ethyne fell to zero, a sample was taken and analyzed by gas chromatography. 91.7% by weight of vinyl cyclohexyl ether and about 0.4% by weight of unconverted cyclohexanol were obtained. The residue was about 6% by weight, consisted predominantly of the potassium cyclohexoxide catalyst and was predominantly undissolved. The remainder is attributable to quantitatively insignificant materials, such as ethyne and ethyl vinyl ether. The conversion of cyclohexanol was 99.6%, based on the cyclohexanol used. The productivity rate was 0.10 kg of vinyl cyclohexyl ether per liter of reaction volume per hour.

Workup

  1. customA jet loop reactor having
  2. customan internal volume of about 10.5 l and equipped with a jet nozzle
  3. customfitted at the head of the reactor
  4. customformed in the reaction
  5. customAny excess product was removed by a pressure control

Sources & evidence

ORD record
ord-ece2d827b9e945fc8139319218db8761
Source dataset
uspto-grants-2004_09
Patent number
US06794546B2

Reaction notes

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