Pentachlorophenol → HCID 86733449, compound

HRID 2419181Notes

Reaction equation

HRID 2419181 reaction equation
[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[CH2:24]([OH:28])[CH:25]([OH:27])[CH3:26].[Cl:29][C:30]1[C:35]([OH:36])=[C:34]([Cl:37])[C:33]([Cl:38])=[C:32]([Cl:39])[C:31]=1[Cl:40].[Al].[CH2:42]1[O:45][CH:43]1[CH3:44].[CH2:46]([N:48]([CH2:51][CH3:52])[CH2:49][CH3:50])[CH3:47]>[Fe]>[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[CH2:24]([OH:28])[CH:25]([OH:27])[CH3:26].[Cl:29][C:30]1[C:35]([OH:36])=[C:34]([Cl:37])[C:33]([Cl:38])=[C:32]([Cl:39])[C:31]=1[Cl:40].[CH2:42]1[O:45][CH:43]1[CH3:44].[CH2:46]([N:48]([CH2:51][CH3:52])[CH2:49][CH3:50])[CH3:47]

Participants

8

Reactant 6

HCID 992Pentachlorophenol2×HCID 1030Propylene GlycolHCID 5988SucroseHCID 6378Propylene Oxide3×HCID 8471TriethylamineHCID 5359268Aluminum

Product 1

HCID 86733449HCID 86733449, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
142 °C

Procedure

A 5-liter flask, standardly equipped, was charged with 535 grams of sucrose and 190 grams of propylene glycol. The mixture was stirred and heated for several hours at up to 142° C. at which time the last of the solid was in solution. Upon cooling the mixture to 28° C., the mixture was too viscous to stir. However, upon slight reheating the mixture stirred readily. At 137° C. 1330 grams of pentachlorophenol containing about 700 to 800 ppm of aluminum and iron compounds was added. During the addition of the pentachlorophenol the temperature dropped to 81° C. but the mixture still stirred readily. Propylene oxide was added at a temperature of up to 142° C. until the acid number was 1.5. The desired amount of propylene oxide had been added so 13 grams of triethylamine was introduced and then propylene oxide was added to the mixture until steady refluxing occurred. The mixture was heated to strip the volatiles at 82°-96° C./1-2 mm. Hg. The oxypropylated product weighed 2924 grams. It was filtered through coarse paper and 5.2 grams of unidentified solid was removed. The oxypropylated product had the following properties.

Workup

  1. customA 5-liter flask, standardly equipped
  2. temperatureUpon cooling the mixture to 28° C.
  3. stirringto stir
  4. stirringHowever, upon slight reheating the mixture stirred readily
  5. customAt 137° C
  6. additiondropped to 81° C.
  7. stirringthe mixture still stirred readily
  8. additionwas introduced
  9. temperatureuntil steady refluxing
  10. temperatureThe mixture was heated
  11. customat 82°-96° C.
  12. filtrationIt was filtered through coarse paper and 5.2 grams of unidentified solid
  13. customwas removed

Sources & evidence

ORD record
ord-27c82fa75f354c01928221eed3860cdd
Source dataset
uspto-grants-1978_08
Patent number
US04105597

Reaction notes

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