Phosphoric Acid → HCID 86586582, compound

HRID 348533Notes

Reaction equation

HRID 348533 reaction equation
C([CH:5]([OH:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]CC)CCC.[OH-].[K+].[CH2:16]1[O:19][CH:17]1C.P(=O)(O)(O)O.[CH2:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:26][CH2:27][CH3:28].C(C(CCCC)C(O)=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:17]([O:19][C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:16].[CH2:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 7

HCID 1004Phosphoric AcidHCID 6101p-Toluenesulfonic acidHCID 6378Propylene OxideHCID 86972-Ethylhexanoic AcidHCID 14797Potassium Hydroxide2×HCID 25046Dodecan-5-olHCID 10899376Octane, 1-butoxy-2×

Product 1

HCID 86586582HCID 86586582, compound

Conditions

Temperature
80 °C

Procedure

4 moles (744 grams) of Butyloctanol were charged to an autoclave, and 0.1% of Potassium Hydroxide was added as catalyst. The autoclave was purged with Nitrogen and 16 moles (928 grams) of Propylene Oxide were added at a temperature of 150–160° C. and a pressure of 30–40 psi. Upon completion, the batch was cooled to 80° C. and neutralized with Phosphoric Acid. The resultant product, PPG-4 Butyloctyl Ether, was a very pale yellow liquid. A four-neck flask was charged with 1,224 grams of the PPG-4 Butyloctyl Ether, along with 3 moles (432 grams) of 2-Ethyl Hexanoic Acid. A catalytic amount of p-Toluenesulfonic Acid was added and the reaction mixture was heated with agitation to 160° C. until an acid value of less than 5 mg KOH was obtained. The reaction mixture was cooled to 80° C., washed with a dilute Sodium Hydroxide solution sufficient to neutralize the residual acid present, followed by washing with water. The ester layer was separated and heated under vacuum until a moisture content of less than 0.2% was obtained, followed by vacuum filtration. The resultant product, PPG-4 Butyloctyl Ether Ethylhexanoate, was a clear very pale yellow liquid having an acid value of less than 0.1 mg KOH.

Workup

  1. additionwas added as catalyst
  2. additionwere added at a temperature of 150–160° C.
  3. customwas obtained
  4. washwashed with a dilute Sodium Hydroxide solution sufficient
  5. washby washing with water
  6. customThe ester layer was separated
  7. temperatureheated under vacuum until a moisture content of less than 0.2%
  8. customwas obtained
  9. filtrationfollowed by vacuum filtration

Sources & evidence

ORD record
ord-be2d0431263f4158a1f3251b22a2f7ec
Source dataset
uspto-grants-2007_02
Patent number
US07176329B2

Reaction notes

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