2,6-di-
tert
-butyl-4-vinylphenol %&'
( )* + * ,-
Preparation of 2,6-di-
tert
-butyl-4-vinylphenol antioxidant for grafting onto Natural Rubber
1
2*
3
! !
4
Anyarat Kiarttisarekul
1
, Pairote Klinpituksa
2*
, Azizan Kaesaman
3
and Charoen nakason
4
*67 8
9 : ;
: <= 9! >
?
@A B
CD
2,6-di-
tert
-butyl-4-vinylphenol
>
IA?
J
: J 9K A
2,6-di-
tert
-butyl-4-vinylphenol
@ =L Wittig
3,5-di-
tert
-butyl-4-
hydroxylbenzaldehyde J methyltriphenylphosphonium iodide I THF T I ?
J U
VWTX
0
˚
C
=Z
: 1
A: 9
30
3,5-di-
tert
-butyl-4-hydroxylbenzaldehyde B
@ C 2,6-di-
tert
-
butylphenol C I @
[?
[?
VWTX
107-109 9U
=Z
:
6 A: 9
?
@A @?
V =Z
[ 9 W : W >
9W >
@ U^
V _ [ 9 2,6-di-
tert
-butyl-4-
vinylphenol @?
: ! ! C @ =
=D
@ 9 J <J @X
@ >
9 [! >
3600
-1
, 1629
-1
, 1362
-1
1234
-1
^
9 @9<^
9W XB
O-H, -CH=CH
2
, -C(CH
3
)
3
C-O I ! 9 ?
9[ 9 2,6-di-
tert
-
butyl-4-vinylphenol
d
@J
79
9
7::
?
@A 9K A 2,6-di-
tert
-Butyl-4-vinylphenol
Abstract
This research was aimed to prepare the phenolic antioxidant 2,6-di-
tert
-butyl-4-vinylphenol (2,6-DBVP) for
grafting onto natural rubber as an internal antioxidant. The 2,6-DBVP was prepared by Wittig reaction from 3,5-di-
tert
-butyl-4-hydroxylbenzaldehyde and methyltriphenylphosphonium iodide in THF under nitrogen atmosphere at
0
˚
C for 1.30 hrs. The 3,5-di-
tert
-butyl-4-hydroxylbenzaldehyde was firstly prepared by reflux of 2,6-di-
tert
-
butylphenol and formalin in the glacial acetic acid and ammonium acetate at 107-109
˚
C for 6 hrs. The 2,6-DBVP
obtained was yellow viscous. The structure of 2,6-DBVP was characterized by IR spectroscopy. It was found that the
appearance of absorption bands at 3600 cm
-1
, 1629 cm
-1
, 1362 cm
-1
and 1234 cm
-1
corresponding to O-H , -
CH=CH
2
, -C(CH
3
)
3
and C-O in 2,6-DBVP structure, respectively.
Keywords:
Antioxidant, Natural rubber, 2,6-di-
tert
-Butyl-4-vinylphenol
1
=
!
!V : U
!
2
U.@ ., T !:A ! W !V : U
!
3
U., T !:A !
9
!V : U
!
