Water → Mercury

HRID 261128Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10].C(=O)([O-])[O-].[Na+].[Na+].[F:17][C:18]1[C:19]([O:31][C:32]([F:60])=[C:33]([F:59])[C:34]([F:58])([F:57])[C:35]([F:56])([F:55])[C:36]([F:54])([F:53])[C:37]([F:52])([F:51])[C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])=[C:20]([S:27](Cl)(=[O:29])=[O:28])[C:21]([F:26])=[C:22]([F:25])[C:23]=1[F:24].[Hg:61].[C:62]([OH:85])(=O)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83].O>C1(C)C=CC=CC=1>[Hg:61].[C:62]([NH2:1])(=[O:85])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83].[F:17][C:18]1[C:19]([O:31][C:32]([F:60])=[C:33]([F:59])[C:34]([F:58])([F:57])[C:35]([F:56])([F:55])[C:36]([F:54])([F:53])[C:37]([F:52])([F:51])[C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])=[C:20]([S:27]([NH2:1])(=[O:29])=[O:28])[C:21]([F:26])=[C:22]([F:25])[C:23]=1[F:24].[F:17][C:18]1[C:19]([O:31][C:32]([F:60])=[C:33]([F:59])[C:34]([F:58])([F:57])[C:35]([F:56])([F:55])[C:36]([F:54])([F:53])[C:37]([F:52])([F:51])[C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])=[C:20]([S:27]([NH2:1])(=[O:29])=[O:28])[C:21]([F:26])=[C:22]([F:25])[C:23]=1[F:24].[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10]

Participants

Conditions

Temperature: 80 °C

Procedure

7.3 g of triethylenetetramine (0.05 mol) in 30 ml. of toluene was heated to 75° C. and a mixture of 5.3 g of sodium carbonate and 67.3 g of perfluorodecenyloxybenzene sulfonyl chloride was added over a period of 20 minutes while maintaining the temperature at 80° C. After half an hour of further reaction at 80°-90° C., the reaction mixture was stripped of solvent to a temperature of 150° C. and 45 mm mercury pressure. There was then added 16.4 g of behenic acid (0.05 mol) and 30 ml. of toluene and the mixture was reacted at 115°-120° C. until 0.05 mol of water had evolved (11/4 hours). The solvent was then stripped to a temperature of 100° C. and 30 mm. mercury pressure to yield the product, triethylenetetramine bis-(perfluorodecenyloxybenzene sulfonamide) monobehenamide, a tan, hard solid with good oil, water and soil repellancy.

Workup

additionwas added over a period of 20 minutes
customAfter half an hour of further reaction at 80°-90° C.
custom(11/4 hours)
customwas then stripped to a temperature of 100° C. and 30 mm

Sources & evidence

ORD record: ord-fdf9225ee80143cc89f931117c9140e7
Source dataset: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04163754

Reaction notes

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