Pentachlorophenol → HCID 86733442, compound

HRID 1388092Notes

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].[Br:23][C:24]1[C:25]([Br:37])=[C:26]([Br:36])[C:27]([Br:35])=[C:28]2[C:33](=[O:34])[O:32][C:30](=[O:31])[C:29]=12.[CH2:38]([O:40][P:41]([O:45][CH2:46][CH3:47])[O:42][CH2:43][CH3:44])[CH3:39].[CH2:48]1[O:51][CH:49]1[CH3:50]>[Fe].C(N(CC)CC)C>[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].[CH2:38]([O:40][P:41]([O:45][CH2:46][CH3:47])[O:42][CH2:43][CH3:44])[CH3:39].[Br:23][C:24]1[C:25]([Br:37])=[C:26]([Br:36])[C:27]([Br:35])=[C:28]2[C:33](=[O:34])[O:32][C:30](=[O:31])[C:29]=12.[CH2:48]1[O:51][CH:49]1[CH3:50]

Participants

Conditions

Temperature: 120 °C

Procedure

A 5-liter flask, standardly equipped, was charged with 411 grams of pentaerythritol, 699 grams of pentachlorophenol containing about 750 ppm of aluminum and iron compounds, 699 grams of tetrabromophthalic anhydride, and 290 grams of triethylphosphite. After heating to 120° C., 1100 ml. of propylene oxide was added over a 4-day period at a temperature of 100°-144° C. The acid number at this stage was approximately 6. Then 2.8 grams of triethylamine was added, followed by the addition of propylene oxide at a temperature of 118°-135° C. to reduce the acid number to less than 1. The mixture was stripped for approximately 35 hours at 90°-102° C./5 mm. Hg pressure. A sample of the oxypropylated polyol product analyzed as follows:

Workup

customA 5-liter flask, standardly equipped

Sources & evidence

ORD record: ord-c1ed5051b3a548e89e8793c22605fb20
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04430247

Reaction notes

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