1,4-Dichlorobenzene → HCID 17864968, compound

HRID 2099599Notes

Reaction equation

HRID 2099599 reaction equation
[S-2:1].[Na+].[Na+].C([O-])(=O)C.[Na+].Cl[C:10]1[CH:15]=[CH:14][C:13](Cl)=[CH:12][CH:11]=1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Cl)[CH:19]=1>CN1C(=O)CCC1.O>[C:10]12[S:1][C:12](=[CH:13][CH:14]=[CH:15]1)[CH:11]=2.[C:18]12[S:1][C:21]([CH:22]=[CH:23]1)=[CH:20][CH:19]=2

Participants

8

Reactant 4

HCID 46851,4-DichlorobenzeneHCID 109431,3-DichlorobenzeneHCID 14804Sodium SulfideHCID 517045Sodium Acetate

Product 2

HCID 17864968HCID 17864968, compoundHCID 20508629HCID 20508629, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent3×

Conditions

Temperature
205 °C

Procedure

Sodium sulfide 9 hydrobase 6.005 kg (25 mol), sodium acetate 0.69 kg (98.25 mol) and NMP 4.1 kg are thrown in an autoclave with agitator, heated gradually to 205° C. introducing nitrogen, and water of 3.6 litter is distillated. Next, the reaction vessel is cooled to 180° C., p-dichlorobenzen 3.582 kg (24.4 mol), m-dichlorobenzen 0.188 kg (1.28 mol) and NMP 3.2 kg are added, sealed under nitrogen, heated to 270° C., and thereafter, let react at 270° C. for 2.5 hours. Next, the above is thrown in NMP 10 kg that is heated to 100° C., agitated continuously for about one hour and filtered, and washed three times for 30 minutes with hot water of 80° C. This is filtered, dried for 24 hours at 80° under reduced pressure, to obtain PPS-4 of 5 mol % in m-phenylene sulfide unit to the total of m-phenylene sulfide and p-phenylene sulfide, 180° in crystallization temperature during cooling, 0.5 weight % in chloroform-extractable content and 160 g/10 minutes in MFR.

Workup

  1. temperatureNext, the reaction vessel is cooled to 180° C.
  2. customsealed under nitrogen
  3. temperatureheated to 270° C.
  4. customlet react at 270° C. for 2.5 hours
  5. temperatureis heated to 100° C.
  6. filtrationfiltered
  7. washwashed three times for 30 minutes with hot water of 80° C
  8. filtrationThis is filtered
  9. customdried for 24 hours at 80° under reduced pressure

Sources & evidence

ORD record
ord-0437eceb54494d59b2484a31d0c03220
Source dataset
uspto-grants-2009_08
Patent number
US07569635B2

Reaction notes

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