Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1987-12-01
1989-12-05
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568451, 568455, 568466, C07C 4550
Patent
active
048854000
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to an improved process for the production of 2-chloropropionaldehyde from vinyl chloride, carbon monoxide and hydrogen.
BACKGROUND ART
2-Chloropropionaldehyde can find applications as useful intermediates for chemicals, agricultural chemicals and medicines. It has been known to produce this compound from vinyl chloride, carbon monoxide and hydrogen as raw materials, as disclosed, for example, in French Patent No. 1,397,779 and HELVETICA CHIMICA ACTA, 48(5), 1151-1157. All of these processes employ cobalt carbonyl as a catalyst In French Patent No. 1,397,779 referred to above, for example, the raw materials are reacted for 90 minutes under the conditions of a reaction temperature of 110.degree. C. and a reaction pressure of 200 atm., thereby obtaining reaction results of a vinyl chloride conversion of 57.4% and a selectivity to 2-chloropropionaldehyde of 86.2%
However, these processes which employ cobalt carbonyl as a catalyst require cobalt carbonyl in a large amount and a reaction pressure as high as 160-200 atm. because the catalytic activity per unit amount of cobalt is extremely low. Moreover, the reaction is carried out at a reaction temperature of 75.degree.-125.degree. C. for 90-120 minutes.
The intended product, 2-chloropropionaldehyde, is a thermally-unstable material. Under the conditions of such a reaction temperature and reaction time, a substantial portion of 2-chloropropionaldehyde is consumed through a consecutive reaction and the reaction yield is thus reduced. Accordingly, these processes have poor reproducibility.
Further, hydrogen chloride is by-produced through the consecutive reaction or other side reactions. It causes the materials of reactor to suffer severe corrosion and it reacts with the cobalt carbonyl catalyst to form cobalt chloride. Therefore, the processes involve problems of developing an obstacle to the reutilization of the catalyst.
In these processes, no reference is made to the separation of the product, 2-chloropropionaldehyde, from a reaction solution containing the catalyst or to the recovery and recycle of the catalyst which is important in the industrial production of 2-chloropropionaldehyde.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to solve the above problems involved in the prior art processes and to provide a process for effecting efficient separation of the product, 2-chloropropionaldehyde, from a reaction solution containing the catalyst and performing the reaction stably over a long period of time upon the reutilization of the catalyst.
The above-described object of the present invention is achieved by the production process of 2-chloropropionaldehyde as described below.
In the production of 2-chloropropionaldehyde by reacting vinyl chloride, carbon monoxide and hydrogen in the presence of a rhodium compound and a base, a process for producing 2-chloropropionaldehyde which comprises maintaining the concentration of 2-chloropropionaldehyde in the liquid phase in the reaction system at not higher than 100 grams per liter of the liquid phase.
BRIEF DESCRIPTION OF THE DRAWING
The appended drawing is a flowsheet illustrating an embodiment of the present invention.
BEST MODE FOR CARRYING OUT THE INVENTION
In the production process of 2-chloropropionaldehyde of the present invention, the reaction proceeds in accordance with the following reaction formula:
In the process of the present invention, the term "base" generally signifies a Lewis base containing a Group VB element of the periodic law such as nitrogen, phosphorus or arsenic. In the absence of such a base, the rhodium compound does not exhibit any catalytic function to the aforesaid reaction.
As a preferred base useful in the process of the present invention may be mentioned, among the aforesaid bases, a base represented by the general formula P[R.sup.1 R.sup.2 R.sup.3 ] wherein P denotes a phosphorus atom and R.sub.1, R.sup.2 and R.sup.3 signify individually the same or different alkyl, aryl, cycloalkyl, alkoxy, aryloxy or cycloal
REFERENCES:
patent: 3239570 (1966-03-01), Slaugh et al.
patent: 4654445 (1987-03-01), Ono et al.
patent: 4740626 (1988-04-01), Bahrmann et al.
Kasuga Takaharu
Ono Hiroshi
Lone Werren B.
Mitsui Toatsu Chemicals Incorporated
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