Sodium Bicarbonate → 1-Octanethiol

HRID 1073978Notes

Reaction equation

HRID 1073978 reaction equation
C(N([CH2:17][C:18](O)=O)CC(O)=O)C[N:3](CC(O)=O)CC(O)=O.[Na].[Na].[C:23](=O)(O)[O-].[Na+].[CH2:28](O[S:41]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=O)=O)[CH2:29][CH2:30]CCCCCCCCC.[Na]>O>[CH3:23][C:17]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[CH2:18].[C:28](#[N:3])[CH:29]=[CH2:30].[CH2:44]([SH:41])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 9949814Ethylenediaminetetraacetic acid disodiumHCID 57371080Sodium dodecylbenzene sulphonate

Product 2

HCID 81441-OctanethiolYield 1,572.1%HCID 168415Acrylonitrile alpha-methylstyrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A one-gallon, glass-lined latex reactor was charged with 1691 g of deionized water, 107 g of polystyrene seed latex (400 Angstrom number average particle size) (30% active), 0.2 g of disodium ethylene diaminetetraacetic acid, 1.0 g of sodium bicarbonate, and 20 g of 43% aqueous sodium n-dodecylbenzene sulfonate. The mixture was purged with nitrogen, and the reactor was then evacuated with a water aspirator three times at room temperature. After the final evacuation, the reactor was pressurized with 10 psi (69 KPa) of nitrogen. The reactor was heated to 85° C. and stirred at 150 rpm. An aqueous feed consisting of 154 g of water, 27.7 g of 43% aqueous sodium n-dodecylbenzene sulfonate, and 2.7 g of sodium persulfate and a monomer feed consisting of 750 g of α-methylstyrene, 187.5 g of acrylonitrile, (providing a ratio α-methylstyrene/acrylonitrile of 80/20) and 0.68 g of n-octyl mercaptan (first monomer feed stream) were started simultaneously and added at rates of 37.4 and 234.6 g per hour to the reaction, respectively. After four hours, addition of first monomer feed stream was halted and the second monomer feed stream consisting of 41.4 g of acrylonitrile and 0.53 g of n-octyl mercaptan was started at a rate of 20.7 g per hour. The aqueous feed rate was changed to 15.5 g per hour. The additions of aqueous feed and second monomer stream were continued for three additional hours. Total monomer feed resulted in a ratio, α-methylstyrene/acrylonitrile, of 77/23. The second monomer feed was then halted, the aqueous feed continued for an additional 15 minutes, and the mixture was retained at 85° C. for 15 minutes. An antifoaming agent (antifoam H-10, 15% active, available from Dow Corning Corporation) was added and volatile components were steam distilled from the mixture. The reaction went to 92% conversion.

Workup

  1. customThe mixture was purged with nitrogen
  2. customthe reactor was then evacuated with a water aspirator three times at room temperature

Sources & evidence

ORD record
ord-b567de45d08a4fa09752122d89795dea
Source dataset
uspto-grants-1990_11
Patent number
US04972032

Reaction notes

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