Hydrochloric Acid → HCID 54290234, compound

HRID 1578831Notes

Reaction equation

HRID 1578831 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1.[CH2:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(OOC(C)(C)C)(C)(C)C.Cl.C1OC1C.C(=O)([O-])[O-].[Na+].[Na+].S(=O)(=O)=O.[OH-].[Na+]>>[CH2:21]([C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:3]=1[CH2:2][OH:1])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

9

Reactant 8

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 8033Di-tert-butyl peroxideHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide3×HCID 155123-Cyclohexene-1-methanolHCID 170951-TrideceneHCID 24682Sulfur trioxide2×

Product 1

HCID 54290234HCID 54290234, compound

Conditions

Temperature
50 °C

Procedure

To prepare a desired anionic biodegradable detergent, 4-hydroxymethylcyclohexene which is prepared according to the method set forth in Example I above is treated in a similar manner by alkylating said substituted cyclohexene with 1-tridecene utilizing a catalyst comprising di-t-butyl peroxide and a promoter comprising concentrated hydrochloric acid in an autoclave under 30 atmospheres of nitrogen and a reaction temperature in the range of from 130° to 140° C. for a period of 1 hour. The n-tridecyl hydroxymethylcyclohexene which is prepared according to this method, after recovery from the reaction mixture, is alkoxylated by treatment with 3 moles of propylene oxide per mole of substituted cyclohexene, the alkoxylation step being effected in an autoclave in the presence of a catalytic amount of sodium carbonate, the autoclave being heated to a temperature of 50° C. and being maintained thereat for a period of 4 hours. Upon completion of the 4-hour period, the autoclave is allowed to return to room temperature, the excess pressure is discharged and the n-tridecyl hydroxypolypropoxymethylcyclohexene is recovered. This product is then placed in an autoclave provided with cooling means and a molar excess of sulfur trioxide is charged thereto. Upon completion of the addition of the sulfur trioxide, the mixture is again stirred for an additional period of 1 hour and neutralized by the addition of a sodium hydroxide solution, the addition of the sodium hydroxide accompanied by stirring and cooling of the reaction mixture during a 1 hour period. Upon completion of the addition of the sodium hydroxide and after an additional period of 1 hour during which the reaction mixture is continuously stirred, the desired product comprising the sodium sulfate ester of n-tridecyl hydroxypolypropoxymethylcyclohexene is separated and recovered.

Workup

  1. customis prepared
  2. additionabove is treated in a similar manner
  3. temperaturebeing maintained
  4. customUpon completion of the 4-hour period
  5. customto return to room temperature
  6. customthe n-tridecyl hydroxypolypropoxymethylcyclohexene is recovered
  7. customprovided with cooling means
  8. stirringby stirring
  9. temperaturecooling of the reaction mixture during a 1 hour period
  10. stirringafter an additional period of 1 hour during which the reaction mixture is continuously stirred
  11. customis separated
  12. customrecovered

Sources & evidence

ORD record
ord-ce17a81b6fa747aa99e8c2dffc22a4ca
Source dataset
uspto-grants-1976_02
Patent number
US03939197

Reaction notes

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