Bisphenol A → 4,4'-{Isopropylidenediphenol} octylphosphite

HRID 25354

Reaction equation

HRID 25354 reaction equation
C1(C(C2C=CC=CC=2)([PH:15]([O-])([O-:17])[O-:16])C(CC)CCCC)C=CC=CC=1.[OH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)([CH3:34])[CH3:33])=[CH:28][CH:27]=1.[Na]>>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([OH:25])=[CH:31][CH:30]=1)([C:35]1[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=1)([CH3:34])[CH3:33].[CH2:26]([O:25][P:15]([O-:17])[O-:16])[CH2:27][CH2:28][CH2:29][CH2:32][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 3

HCID 6623Bisphenol AHCID 5360545SodiumHCID 178442637HCID 178442637, compound

Product 1

HCID 1317247464,4'-{Isopropylidenediphenol} octylphosphite

Procedure

In a round bottom flask, 34.6 g (0.1 mol) of diphenyl-(2-ethylhexyl)phosphite, 22.8 g (0.1 mol) of bisphenol-A, and a catalytic quantity of metallic sodium (or alcoholate of an alkali metal) was heated at 180° C. under an atmosphere of nitrogen for one hour. The temperature was reduced to 90-100° C. The phenol was then removed under vacuum (10 mm) over 2.5 hours. When the residual pressure dropped to 1 mm, the reaction mass was subjected to vacuum for two more hours. The yield was quantitative. The phosphorus-31 NMR showed a series of peaks from 126 to 131 ppm.

Workup

  1. customwas reduced to 90-100° C
  2. customThe phenol was then removed under vacuum (10 mm) over 2.5 hours
  3. additionWhen the residual pressure dropped to 1 mm

Sources & evidence

ORD record
ord-9d0d135e03344dec9f4be50c80bf0de4
Source dataset
uspto-grants-2005_02
Patent number
US06858662B2

Linked notes

Loading…