[•rawnEPWïTTiTâ ΕΙΜΙ Màff^ttMMmmÊS^^Km
Nov^^M)lè1rrB« We ran our first ad on oxalyl chloride some twelve years ago and have filled much of the world's research needs for it ever since. It was made in 50-L flasks from anhydrous oxalic acid and PCI 5 , a method that is difficult to scale up. Now we use a much better method and can supply ton lots q u i c k l y . O u r p r o d u c t is m u c h purer, higher than 99% with prac tically no heavy metal impurities.
include: s t a b i l i z e r f o r c o l o r photo g r a p h i c m a t e r i a l , f o r m a t i o n of m o n o m e r s of t h e r m a l l y s t a b l e p o l y m e r s , f o r m a t i o n of p o l y amides useful as UV absorbers, polymerization catalyst, polymer crosslinking agent, production of resins for affinity chromatography, production of photopolymerizable printing materials, and chemiluminescent formulations. Call our toll-free number800-5589160 and ask for a bulk quotation and data sheet.
Most uses of oxalyl chloride are well known (cf. Fieserand Fieser, Reagents for Organic Synthesis, 1,767 2,301 3,216 4,361 5,481 6,424 7,257 and Merck Index, 9,6745). Recent applications are given below. But oxalyl chloride is also finding many industrial applications, often as surprising as t h e y are i n t r i g u i n g . T h e s e
ΤΙΛ
aldricti chemical co. r.»'HM!i
940 West Saint Paul Avenue Milwaukee, Wisconsin 53233
Some recent applications are:
o-Formylation of phenols:
Formation of very reactive acid chlorides: CH3^ C6H5"
^C02H
c=c
^CH 3
r ^ >
CH3N^ _ ^ C O C I
(COC|)2
/
PhH
C=C
C CH
3
J^^l
Py
9
AICI,
OH
KI04
CHOHCH 2 OH
0 n0 RO£c oo-,-Bu
-ΕΞι_ Γ„Ί J
ο - CICH 2 C"N=C=0 + CO + 2HCI
^S
CH0
Preparation of chloroiminium chloride intermediates:
RCI + C 0 + C0 2
Conversion of amides to isocyanates: CICH 2 CNH 2 + (C0Cl) 2
OH
LiAIH4
Formation of alkyl chlorides: oo
I
C
vocococi
(CQC»2
X
C6H5
ROH4-(COC.)2-^ROC^C|100-125°
0 H
^
RC(
R2/N-C-R>
-
(C0CI) 2 —
R\* /R N=C CI
_ CI
Reduction of phosphine oxides to phosphines via the dichlorides: R3PO + ( C 0 C I ) 2
-R3PCI2
Et3N R'SH
R3P + (R'S) 2 + 2Et 9 N*HCI
