Bisphenol A → 1,3-Bis(4-cyanophenyl)propane

HRID 839772Notes

Reaction equation

HRID 839772 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N:18]#[C:19]Cl.[CH2:21]([N:23](CC)CC)C>CC(C)=O>[O:1]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:19]#[N:18])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1)[C:21]#[N:23]

Participants

5

Reactant 3

HCID 6623Bisphenol AHCID 8471TriethylamineHCID 10477Cyanogen Chloride

Product 1

HCID 708721,3-Bis(4-cyanophenyl)propaneYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

According to Example 7 of U.S. Pat. No. 3,553,244, 228 parts by weight of 2,2-bis-(4-hydroxyphenyl)-propane are dissolved in 400 parts by weight of acetone and cooled to 0° C. 135 parts by weight of cyanogen chloride are added dropwise at that temperature. 120 parts by weight of triethylamine are then added with external cooling, the temperature being kept below 10° C. On completion of the dropwise addition, the mixture is stirred for 30 minutes, after which the triethylamine hydrochloride which has crystallized out is filtered off. After the acetone has been distilled off, 2,2-bis-(4-cyanatophenyl)-propane is obtained from the filtrate in the form of colorless crystals melting at 77° to 80° C in a quantity of 212 parts by weight (corresponding to a yield of 76%, based on the theoretical amount). The purity amounts to approximately 95% (as determined by IR-spectroscopy).

Workup

  1. custombeing kept below 10° C
  2. additionOn completion of the dropwise addition
  3. customafter which the triethylamine hydrochloride which has crystallized out
  4. filtrationis filtered off
  5. distillationAfter the acetone has been distilled off

Sources & evidence

ORD record
ord-f106ac6674e3443699de56478f512a3e
Source dataset
uspto-grants-1978_06
Patent number
US04097455

Reaction notes

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