3-Chloro-1,2-propanediol → 1,2-Dihydroxypropane dodecyl sulfide

HRID 1654425

Reaktionsgleichung

Reaktionsgleichung von HRID 1654425
[OH-].[Na+].[CH2:3]([SH:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl[CH2:17][CH:18]([OH:21])[CH2:19][OH:20]>C(O)(C)C>[CH2:3]([S:15][CH2:17][CH2:18][CH2:19][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH:20][CH2:19][CH:18]([OH:21])[CH3:17]

Komponenten

5

Edukt 3

HCID 72903-Chloro-1,2-propanediolHCID 81951-DodecanethiolHCID 14798Sodium Hydroxide

Produkt 1

HCID 867397751,2-Dihydroxypropane dodecyl sulfide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Approximately 97 g of 50% aqueous sodium hydroxide solution was added dropwise over a period of 7 hours to a solution of n-dodecyl mercaptan (1000 g) and 1-chloropropane-2,3-diol (547 g) in isopropanol solvent (2000 cc) at ambient temperature. The reaction temperature rose from 21° to 56° C. during the addition. The reaction was refluxed for 5 hours at 80° C. and then filtered hot through paper to remove the precipitated salt. The isopropanol solvent was removed by distillation. The product residue was dissolved in about 4000 cc of toluene and washed with water several times. The toluene solution was dried over magnesium sulfate and filtered through diatomaceous earth. Toluene was removed by high speed rotary evaporation under reduced pressure to yield a white solid product.

Aufarbeitung

  1. additionThe reaction temperature rose from 21° to 56° C. during the addition
  2. filtrationfiltered hot through paper
  3. customto remove the precipitated salt
  4. customThe isopropanol solvent was removed by distillation
  5. dissolutionThe product residue was dissolved in about 4000 cc of toluene
  6. washwashed with water several times
  7. dry with materialThe toluene solution was dried over magnesium sulfate
  8. filtrationfiltered through diatomaceous earth
  9. customToluene was removed by high speed rotary evaporation under reduced pressure
  10. customto yield a white solid product

Quellen und Nachweise

ORD-Eintrag
ord-f9be3fbf01ef42c395a74006935bf358
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407451

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