Pentachlorophenol → HCID 86733444, compound

HRID 1447714Notes

Reaction equation

[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[Cl:10][C:11]1[C:16]([OH:17])=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]([Cl:20])[C:12]=1[Cl:21].[Al].[C:23]1([O:29][P:30]([O:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:45]1[O:47][CH2:46]1>[Fe].C(N(CC)CC)C>[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:39]1([O:38][P:30]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Cl:10][C:11]1[C:16]([OH:17])=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]([Cl:20])[C:12]=1[Cl:21].[CH2:46]1[O:47][CH2:45]1

Participants

Conditions

Temperature: 135 °C

Procedure

A 1-gallon autoclave was charged with 478 grams of pentaerythritol and 1357 grams of pentachlorophenol containing about 750 ppm of aluminum and iron compounds and 442 grams of triphenylphosphite. After heating to 135° C. 870 grams of ethylene oxide was added at temperatures of up to 150° C. The mixture was reacted for about an hour and then, after cooling to 50° C., 30 grams of triethylamine was added followed by the addition of 345 grams more of ethylene oxide at up to 125° C. After reacting for approximately 2 hours, the mixture was cooled and discharged. The mixture was stripped for 2 hours at 79°-81° C./1-2 mm. Hg. A sample of the oxyethylated product had the following analyses.

Workup

customThe mixture was reacted for about an hour
temperatureafter cooling to 50° C.
temperaturethe mixture was cooled
waitThe mixture was stripped for 2 hours at 79°-81° C.

Sources & evidence

ORD record: ord-c37b7a6d529544a980460f9fec8c7426
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04177335

Reaction notes

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