Phosgene → C12H25S(CH2CH2O)10COCl

HRID 1462664

Reaction equation

HRID 1462664 reaction equation
[CH2:1]([S:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][OH:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CCCCC(CCC(OS([O-])(=O)=O)CC(C)C)CC.[Na+].[C:64](Cl)([Cl:66])=[O:65]>C(N(CC)CC)C>[CH2:1]([S:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][C:64]([Cl:66])=[O:65])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 9961026C12H25S(CH2CH2O)10HHCID 23665772Sodium Tetradecyl Sulfate

Product 1

HCID 131713586C12H25S(CH2CH2O)10COCl

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

For example, C12H25S(CH2CH2O)10H, such as Tergitol 12-M10, can be reacted with phosgene in the presence of triethyl amine to yield the corresponding acid chloride, C12H25S(CH2CH2O)10COCl, which in turn, is reacted with a fluoroaliphatic alcohol such as (CF3)2CFO--CF2CF2 --CH2CH2CONH(CH2)3OH, disclosed in U.S. Pat. No. 3,697,564, in the presence of triethylamine in diethyl ether to yield a product of the formula (CF3)2CFO--CF2CF2CH2CH2CONH(CH2)3OCO(OCH2CH2)10S--C12H25.

Sources & evidence

ORD record
ord-b0e8f681e4f747a8ad3dc6d8a6705aac
Source dataset
uspto-grants-1984_07
Patent number
US04460791

Linked notes

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