DE937949C - Process for the production of organic compounds containing phosphorus and sulfur - Google Patents

Description

ISSUED JANUARY 19, 1956

B 27633 IVb112

It has been found that phosphines of the general formula R-PH ₂ , (R) ₂ PH and (R) ₃ P, in which R denotes organic radicals of the same type or of different types which are connected to the phosphorus via a carbon atom, are very good easily react with sultons.

As is known, sultones are understood to mean cyclic anhydrides of organic oxysulfonic acids, preferably five- and six-membered anhydrides. The simplest compound in this class, propane sultone, has the formula CH ₂ —CH ₂ —CH ₂ .

O-

SO ₂

Other representatives are e.g. B. butane sultone, the isobutane sultone and the like. The hydrocarbon chains can also contain substituents. Further suitable sultones, in which carbon atoms of a cycloaliphatic or aromatic ring are constituents of the Sulton ring, z. B. the ToIysulton, the 1,8-Naphthsulton etc.

The reaction of the sultones with phosphines probably takes place in such a way that a Alkylation takes place on the phosphorus atom. In the case of primary and secondary phosphines arise Sulfonic acids. Using the example of propane sultone, the implementation can be formulated as follows :

Cxi «· -

: ph

R ''

CH,

SO ₂

P-CH ₈ -CH ₂ -CH ₂ -SOoH

(R '= H or organic residue)

Since the phosphines are very weak bases, the addition of one is necessary to carry out the reaction acid binding agent, e.g. B. anhydrous soda required.

Of particular interest is the. Implementation of the sultones with tertiary phosphines. The very here

(C ₆ H ₅ ) ₃ P +

C Hn · - C Ho - "

SO ₂

Since neutral bodies are formed in the reaction with tertiary phosphines, the addition is unnecessary of .acid binding agents. The reaction is very easy and practically quantitative when the components are mixed and optionally heated. It can use organic solvents or diluents that are not involved in the reaction participate, be used.

As starting materials come for the process z. B. the following phosphines into consideration: Mono-, Di- or trialkylphosphines, mixed di- and trialkylarylphosphines, arylphosphines, cycloalkylphosphines and the like

The products thus obtained can, for. B. find use as a pesticide.

Example ι

26.2 g of triphenylphosphine (melting point 79 ^° ) are melted and mixed with 12.2 g of propane sultone (melting point 31 ^° ). The mixture is heated on an oil bath, the temperature being increased from 70 to 150 ^{0 over the course of} 2 hours. Then heated to an additional 2 hours at 150 to 170 ^0th Crystals of the high-melting reaction product separate out after just a few minutes. Gradually the whole substance turns into a solid crystal cake.

The reaction product, which is very easily soluble in water and alcohol, on the other hand, is insoluble in the most other organic solvents, easily formed products can have high melting points and are likely to be addressed as internal phosphonium salts. The implementation of For example, triphenylphosphine with propane sultone can be formulated as follows:

(C ₆ H _B ) ₃ P

-SO ₃

Claims (1)

PATENT CLAIM: Process for the preparation of organic compounds containing phosphorus and sulfur, characterized in that phosphines of the general formula R-PH ₂ , (R) ₂ PH and (R) ₃ P, in which R denotes organic radicals of the same or different types, which are above a carbon atom are bonded to the phosphorus atom, reacted with sultones, optionally in the presence of acid-binding agents and using inert solvents or diluents. be cleaned in such a way that the crushed crystal cake is dissolved in a little methanol and the solution is treated with a large excess of toluene, in which the starting materials are soluble. The precipitated crystals are filtered off with suction and washed with toluene. Melting point 320 ⁰ , yield 30 to 35 g. Example 2 26.2 g triphenylphosphine and 12.2 g propane sultone are dissolved in 50 ecm xylene and 6 hours refluxed. The precipitated crystals are filtered off with suction and washed with xylene. There Any unreacted starting material can be reused, the yield is practical quantitatively. © 509 620 1.56