Method of making 3,5-dichloro-p-toluoyl chloride

Details Method of making 3,5-dichloro-p-toluoyl chloride Method of making 3,5-dichloro-p-toluoyl chloride

1999-11-05

2001-03-13

Killos, Paul J. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic halides

Reexamination Certificate

active

06201152

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a method of making 3,5-dichloro-p-toluoyl chloride (“DCTOC,” also called “3,5-dichloro-4-methylbenzoyl chloride”) by reacting 3,5-dichloromethyltoluate (“DCMT,” also called “methyl-3,5-dichloro-4-methylbenzoate”) with an &agr;,&agr;,&agr;-trichloromethylbenzene. In particular, it relates to the use of ammonium septamolybdate, (NH
4
)
6
Mo
7
O
24
.4H
2
O (ASM), or ammonium dimolybdate, (NH
4
)
2
Mo
2
O
7
.2H
2
O (ADM), as the catalyst in that reaction. (The amounts of water of hydration may vary.)
In U.S. Pat. No. 4,080,378 toluoyl chloride is made by reacting p-toluylic acid methyl ester with 1,4-bis-(trichloromethyl)-benzene and p-chlorobenzoyl chloride is made by reacting p-chlorobenzoic acid methyl ester with p-chlorobenzotrichloride. In both reactions, the catalyst is molybdenum trioxide (MoO
3
).
SUMMARY OF THE INVENTION
We have discovered that DCTOC can be made by reacting DCMT with an &agr;,&agr;,&agr;-trichloromethylbenzene at conversions of 99% and 96% if the catalyst is ASM or ADM, respectively. It is surprising that such high conversions can be achieved with these catalysts because closely related molybdenum catalysts, such as molybdenum trioxide, have much lower conversions.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
In this invention DCTOC is made by reacting DCMT with an &agr;,&agr;,&agr;-trichloromethylbenzene in the presence of a catalyst such as ASM, ADM, or a mixture thereof.
Examples of &agr;,&agr;,&agr;-trichloromethylbenzenes that can be used include benzotrichloride (BTC), o-chlorobenzotrichloride, m-chlorobenzotrichloride, p-chlorobenzotrichloride (PCBTC), m-bis(trichloromethyl)benzene, p-bis(trichloromethyl)benzene 1,3-bis(trichloromethyl)-5-chlorobenzene, bis(trichloromethyl)dichlorobenzenes, and o-dichloromethyltrichloromethylbenzene. The preferred &agr;,&agr;,&agr;-trichlormethylbenzenes are BTC and PCBTC as they are less expensive and the resulting coproduct (benzoyl chloride or p-chlorobenzoyl chloride, respectively) is commercially valuable. The amount of &agr;,&agr;,&agr;-trichloromethylbenzene used should be about 1 to about 1.4 equivalents as less will leave unreacted DCMT and more may result in the production of unwanted byproducts. Preferably, about 1 to about 1.1 equivalents of the &agr;,&agr;,&agr;-trichloromethylbenzene are used.
The amount of catalyst used should be about 0.01 to about 0.2 equivalents as less will result in a slower reaction and more is unnecessary and wasteful. The preferred amount of catalyst is about 0.02 to about 0.08 equivalents.
The general procedure is to charge the reactor with the DCMT, the &agr;,&agr;,&agr;-trichloromethylbenzene, and the catalyst and heat the mixture to about 150 to about 180° C.; the reaction is slower at lower temperatures and at higher temperatures unwanted byproducts may be produced. The preferred temperature is about 155 to about 165° C. No solvent is needed for the reaction. The reaction is usually complete in about 5 to about 12 hours. The product mixture contains DCTOC and a benzoyl chloride, which can be separated by distillation. DCTOC is used as an agricultural intermediate, benzoyl chloride is used to make plasticizers and peroxides, and methyl chloride is a valuable gas.


REFERENCES:
patent: 4080378 (1978-03-01), Zoche et al.

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