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Sulfuric Acid → Cyclohexanone Oxime

HRID 234110
Notes
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Reaction equation

HRID 234110 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([OH:11])[CH2:7][CH2:8][CH2:9][CH3:10].[C:12]1(=[N:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+]>[C:12]1(=[N:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[C:6]1(=[O:11])[CH2:12][CH2:10][CH2:9][CH2:8][CH2:7]1.[C:12]1(=[O:2])[NH:18][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 62761-PentanolHCID 7517Cyclohexanone Oxime

Product 3

HCID 7517Cyclohexanone OximeHCID 7768CaprolactamHCID 7967Cyclohexanone

Reagents, catalysts & solvents 1

HCID 3423265
Sodium Lauryl Sulfate
Solvent

Conditions

Temperature
25 °C

Procedure

Take 200 ml of aqueous solution of 3.0N sulfuric acid in a round bottom flask. Dissolve in this solution 16 grams of sodium dodecyl sulfate (SDS) and 5.3 gm 1-pentanol by mild stirring. A microemulsion is thus formed. Keep the flask in a water bath maintained at temperature of 25° C. To this microemulsion, add 10.0 gm of cyclohexanone oxime and stir the mixture mildly for 2 hours. Remove the flask from the water bath and neutralize the solution using aqueous solution of ammonia. Filter the solution using Whatman No. 1 filter paper. Measure the amount of filtrate and the residue and extract the filtrate with 100 ml of benzene in steps of 50, 25, and 25 ml respectively. Analyze the benzene layer, the aqueous layer and the residue obtained as above by Gas Chromatography for the amount of cyclohexanone oxime, cyclohexanone and caprolactam.

Workup

  1. customA microemulsion is thus formed
  2. customRemove the flask from the water bath
  3. filtrationFilter the solution
  4. filtration1 filter paper
  5. extractionMeasure the amount of filtrate and the residue and extract the filtrate with 100 ml of benzene in steps of 50, 25, and 25 ml respectively

Sources & evidence

ORD record
ord-5e46c52f020e44479e549eb560fcecaf
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05594137

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes