JPH0276889A - Separation and preparation of alkyltin oxide - Google Patents

Abstract

PURPOSE:To readily separate tri, mono and dialkyltin oxide is turn from an oil phase, a water phase and a dialkyltin oxide phase by hydrolyzing an alkyltin halide by a specific method and subsequently allowing the product to stand for separating the product into the phases, respectively. CONSTITUTION:A mono, di or trialkyltin halide is continuously hydrolyzed with a 1-50% basic substance aqueous solution at 30-100omicronC for 10min-3hrs in the presence of a water-slightly soluble organic solvent having a boiling point of <=150 deg.C at atmospheric pressure and having a specific graving of <=1.1 when the alkyltin halide is solid, thereby producing a dialkyltin oxide having an average particle size of >=10mum in the reaction product. The product is allowed to stand for forming three phases consisting of an oil phase, a water phase and a dialkyltin oxide phase having a specific gravity difference of >=0.02 between the dialkyltin oxide and the water phase. Finally, a bis (trialkyltin) oxide, a monoalkyltin oxide and a dialkyltin oxide are isolated from the oil phase separated by a liquid-separating operation, the water phase and the remaining phase, respectively.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for separating and producing industrially useful mono-, di-, or tri-organotin oxide.

[Prior art/problems to be solved by the invention] Mono- and dialkyltin oxides have high industrial value and are widely used as stabilizers for polyvinyl chloride resins, organic synthesis catalysts, cationic electrodeposition coating catalysts, etc. (trialkyl tin)
oxide or trialkyltin hydroxide (
Hereinafter, collectively referred to as trialkyl tin oxide.)
occupies an important position in the field of antifouling paints. These alkyl tin oxides have conventionally been widely used, for example, as described in U.S. Pat. No. 2,718,522 and U.S. Pat. Hydrolyzed in a batch method with a strong basic substance,
Two phases are formed: an aqueous layer containing salts and, in some cases, an alkali metal salt of monoalkyltin oxide, and an organic layer containing di- and trialkyltin oxide, and the aqueous phase is separated, followed by filtration or centrifugation from the oil phase. It has been produced by separating di- or trialkyltin oxide by mechanical methods such as

However, such a method presents major problems in terms of occupational safety and health, environmental measures, and equipment economy, as described below. In other words, the average particle size of dialkyltin oxide in the oil phase is very fine, usually 10 μm or less, and it is easily compressed by pressure and cannot maintain an independent particle size, so it cannot be filtered or Separation using a pressure-based method such as centrifugation takes a long time, and during that time, the solvent or trialkyltin oxa.f-do volatilizes to a large extent. For example, when manufacturing trialkyl tin oxide, the by-product dialkyl tin oxide is produced in a suspended state as very fine particles in the liquid trialkyl tin oxide, so a filter aid such as acid clay is used. Separation is possible for the first time. Furthermore, since the separated dialkyltin oxide is mixed with a filter aid, it is impossible to reuse it as it is, and it is also difficult to dispose of it as industrial waste.

It is difficult to clearly separate the aqueous salt phase containing monoalkyltin oxide from the trialkyltin oxide phase.
It was necessary to remove some of the mixed trialkyltin compound by extracting it with an organic solvent. Since the effects of trialkyltin oxide on humans and the environment cannot be ignored,
The entire manufacturing process needs to be a closed system, but in conventional filtration or centrifugation operations, not only the equipment itself is extremely expensive, but also it cannot be carried out in a completely closed system.

In the case of di- or mono-alkyltin oxides, the drawbacks are essentially the same as the conventional methods for trialkyltin oxides, but they are more complicated due to the handling of large quantities of solids. That is, the hydrolysis reaction product of dialkyltin sybaride consists of two phases: an aqueous phase containing monoalkyltin oxide and an organic phase containing tri- and dialkyltin oxide, and the desired dialkyltin oxide is separated from the organic phase by centrifugation or The by-product trialkyl tin oxide can be removed by separating it by means such as filtration, suspending and washing the obtained dialkyl tin oxide with a solvent, and repeating the operation of filtration or centrifugation several times. can. However, in order to completely remove salts and alkali metal salts or salts of monoalkyltin oxide, which are reaction by-products, the dialkyltin oxide obtained as described above is washed again with a large amount of water. In each case, it was necessary to separate by means such as filtration and centrifugation.

[Means to solve the problem]

The present inventors believe that the biggest drawback of the conventional method is that it requires filtration or centrifugation operations, and as an alternative, the reaction product is separated from the aqueous phase in the middle and the mechanical phase at the top. As a result of repeated research, based on the idea that if three phases could be formed in which the dialkyl tin oxide could be separated downward, each phase could be easily separated by liquid separation, and furthermore, the operation could be performed in a completely closed system. The method of the present invention could be completed.

The basic concept of the present invention is (1) to increase the particle size of dialkyltin oxide in the reaction product and make it heavier by appropriately selecting the method and conditions of the hydrolysis reaction. (2) By adjusting the specific gravity of the aqueous phase, a liquid organic phase consisting of trialkyltin oxide and a lower phase substantially solely containing dialkyltin oxide are formed above the aqueous phase. (3) The three phases are separated by a liquid separation operation, and mono-, di-, and trialkyltin oxides are isolated from each separated phase.

The present invention provides mono-, di- or trialkyl tin halides.
~50% basic substance aqueous solution, if the alkyltin oxide is solid, in the presence of a poorly water-soluble organic solvent with a boiling point at normal pressure of 150°C or less and a specific gravity of 1.1 or less at 30-100°C Dialkyltin oxide with an average particle size of 10 μm or more is generated in the reaction product by continuously subjecting it to a hydrolysis reaction at a temperature of 10 minutes to 3 hours, and by leaving the obtained reaction product still. Three phases, ie, an oil phase, an aqueous phase, and a phase consisting essentially of dialkyltin oxide having a specific gravity of 0.02 or more, are formed in the aqueous phase, and then bis(
trialkyltin) oxide or trialkyltin hydroxide, monoalkyltin oxide from the aqueous phase,
and a method for separating and producing an alkyltin oxide compound, which comprises isolating dialkyltin oxide from a phase consisting essentially of dialkyltin oxide having a specific gravity difference of 0.02 or more with respect to an aqueous phase.

The alkyltin oxide produced by the method of the present invention is monoalkyltin oxide and/or dialkyltin oxide and/or bis(trialkyltin) oxide or trialkyltin hydroxide, and one or two types thereof may be used depending on the reaction conditions. The above can be obtained with high purity and high quality. Here, alkyl has 1 to 1 carbon atoms.
Eight alkyl groups, including methyl, ethyl, n-propyl, isopropyl, n-butyl, secondary butyl, tertiary butyl, pentyl, isopentyl, neopentyl, n-
Examples include hexyl, n-heptyl, n-octyl, 2-ethylhexyl, 1.1,3.3-tetramethylbutyl, and butyl and octyl are industrially useful. That is, mono-n-butyltin oxide, di-n-butyltin oxide, di-n-octyltin oxide, bis(tri-n-butyltin) oxide, and the like.

The mono-, di- or trialkyltin halide used as a raw material is monoalkyltin trihalide, dialkyltin civalide or trialkyltin halide, such as tri-n-butyltin chloride, di-n-butyltin dipromide, mono-n- Examples include, but are not limited to, butyltin triiodide, di-n-octyltin diiodide, and dimethyltin dichloride. This alkyltin halide usually contains other alkyltin halides and, in some cases, tetraalkyltin, but the amount may be as long as it does not substantially inhibit the reaction, and is generally about 10% by weight. It is as follows. That is, the purity of the alkyltin halide used as a raw material is usually about 90% or more for use.

Furthermore, the basic substances used in the present invention include alkali metal hydroxides, ammonium hydroxide, etc., including, but not limited to, sodium hydroxide, potassium hydroxide, and ammonium hydroxide. Industrially, sodium hydroxide is preferred. These basic substances are usually used as an aqueous solution, and their concentration is selected so that the specific gravity of the aqueous salt solution produced after the hydrolysis reaction is between that of the hydrolysis reaction phase, usually 1 to 50%.
, more preferably 5 to 30%.

The organic solvent is preferably one that dissolves the mono-, di-, or trialkyl tin halide as a raw material well, and does not contain water or the target solid alkyl tin oxide. Furthermore, since these solvents are collected and reused, their high boiling points are difficult to handle.
It is advantageous to have a normal pressure boiling point of about 150°C or less.

Further, it is desirable that the specific gravity is lower than the specific gravity of the aqueous salt solution after the hydrolysis reaction, and a specific gravity of 1.1 or less is used. Examples include, but are not limited to, benzene, toluene, xylene, pentane, hexane, isohexane, heptane, octane, isooctane, cyclohexane, methylcyclohexane, methyl isobutyl ketone, petroleum ether, petroleum benzine, ligroin, petroleum naphtha,
Ethylbenzene, n-butanol, isobutanol, 5
ec-butanol, tert-butanol, pentanol, isopentanol, hexanol, heptatool,
Examples include cyclohexanol, monochlorobenzene, dichloropropane, butyl chloride, amyl chloride, and preferably hydrocarbons such as hebutane, toluene, and xylene. These solvents may be used alone or in mixtures.

One of the basic concepts of the method of the present invention is to increase the particle size of the dialkyltin oxide in the hydrolysis reaction product and make it heavier, so that the diorganotin oxide is substantially isolated in the lower phase than the salt aqueous phase. In order to form a phase containing It is best to do this within one hour. The reaction temperature is preferably 30 to 100°C, preferably 50 to 80°C.

The average particle diameter of the dialkyltin oxide obtained by this method is 110l1 or more, and by selecting optimal conditions, it is possible to obtain a dialkyltin oxide having a diameter of 50 μm or more and a uniform particle size distribution. Such particles can never be obtained by conventional methods and are usually on the order of 10 μm or less.

Adjustment of the specific gravity between the three phases, which is another basic concept, can be done by adding water, basic substances, salts, etc. to the hydrolysis reaction product, or by adding sodium hydroxide, potassium hydroxide, or ammonium hydroxide to be used in the reaction in advance. This is done by adjusting the concentration of basic substances such as The specific gravity of the solvent phase is determined by selecting the type of solvent used in the reaction.

As the basic substance, it is most economical to use an aqueous sodium hydroxide solution. The specific gravity is adjusted. The specific gravity difference between the three phases is 0.02 or more.

In order to better understand the concept of the present invention, it will be further explained with reference to the drawings and compared with the method described in US Pat. No. 2,718,522. That is, as shown in FIG. 1(a), according to the method of the present invention, three-phase separation is performed by hydrolyzing mono-, di-, or trialkyltin halide under the specific conditions of the present invention. Screw (
trialkyltin) oxide or trialkyltin hydroxide by neutralizing 1. Monoalkyltin oxide is separated and produced from the lower phase, and dialkyltin oxide is separated and produced. The fact that the hydrolysis reaction product forms three phases by the method of the present invention is as shown in FIG. 2, and the particle state of the prepared di-n-butyltin oxide is shown in FIG. On the other hand, U.S. Patent No. 2.718.5
In the method No. 22, a crude mixture of butyltin trichloride, dibutyltin chloride, l-dibutyltin chloride and tetrabutyltin is treated with stannic chloride to react with tetrabutyltin to form a butyltin chloride compound, which is then extracted. This method produces diptyltin oxide by hydrolyzing the organic phase with an alkali and filtering it, and di-n-butyltin oxide produced in the same manner is
As shown in the figure, bis(tri-n-butyltin) oxide forms two phases (the lower phase is a saline aqueous layer) in a turbid state in the V phase, and the particle state of di-n-butyltin oxide is the fifth phase. As shown in the figure. To summarize this, the following 1~
It is as shown in Table 2.

- Below margin 1 + 14 Morphology of hydrolysis reaction product and relationship with average particle diameter of di-n-butyltin oxide: 1st
Form of surface material Lower phase: DBTO phase Lower phase: Salts Aqueous phase Reaction conditions: Raw material Nidi-n-butyltin dichloride Basic substance: 15% caustic soda aqueous solution Solvent: Toluene Reaction temperature near 0°C Margin 1 (2) Salts Relationship between specific gravity of aqueous phase and phase separation: Part 2
Table (specific gravity 1.1) (specific gravity 1.1) (specific gravity 1.1
) to 1.26) Larger) Smaller) Reaction conditions: Raw material nitri-n-butyltin chloride basic substance: Caustic soda aqueous solution* The average particle size of the by-product DBTO is 30 μm.

In Tables 1 and 2, DBTO and TBTO are respectively
Means n-butyltin oxide and bis(tIJ-n-butyltin) oxide.

When producing trialkyltin oxide by the method of the present invention, the target product is a liquid and there is no need to use a solvent. When the hydrolysis reaction product is allowed to stand still, it immediately separates into an aqueous salt phase and an oil phase consisting essentially of trialkyl tin oxide, and then the dialkyl tin oxide particles in the oil phase constantly open a small amount of the oil phase to form oil droplets. It passes through the saline aqueous phase and sinks to the bottom. Once the sedimentation is complete, the hydrolysis product is completely separated into three phases: the trialkyltin oxide phase is at the top, the aqueous phase is in the middle, and the dialkyltin oxide phase is at the bottom, and the interface between each phase is clear. The three phases can be easily separated by liquid separation. Although the lower phase contains about 50% or more of dialkyltin oxide, it has good fluidity and can be easily separated. Monoalkyltin oxide is dissolved in the intermediate aqueous phase as an alkali metal salt, and can be recovered as high-grade monoalkyltin oxide through acid precipitation.Also, if the amount is small, it can be directly subjected to biological treatment. can be discharged as industrial wastewater. Almost no dialkyl tin oxide remains in the upper phase of trialkyl tin oxide, and usually 20
00 ppm or less, and the two are almost completely separated. Therefore, in the upper phase, the small amount of water contained in the upper phase is removed by distillation, etc., and then the small amount of precipitated salts is removed.
High quality trialkyl tin oxide can be obtained directly through a simple filtration operation. Di- and trialkyltin oxides can be easily separated and recovered from the lower phase by filtration, or the corresponding di- and trialkyltin oxides can be removed by treating the lower phase with a hydrohalic acid such as hydrochloric acid in a conventional manner. When dialkyltin oxide is produced by the method of the present invention, which can be converted into a halide and then reacted with tetraalkyltin to obtain a high-grade trialkyltin halide, which can be used again as a raw material, the target product is Since it is a solid, it is essentially the same as the case of trialkyltin oxide except that an organic solvent is used for the hydrolysis reaction. In this case, when the hydrolysis reaction product is allowed to stand still, a solvent phase, an aqueous salt phase, and a dialkyltin oxide phase containing the solvent are clearly separated into three phases: upper, middle, and lower. After separating each phase by liquid separation, trialkyltin oxide is obtained by removing the solvent from the solvent phase. Moreover, monoalkyltin oxide is recovered from the salt aqueous phase by acid precipitation. The solvent content in the lower phase is usually 40% or less, and despite the high solids concentration, it is highly fluid. After removing the small amount of salts contained in it by washing with water, the organic solvent is removed by drying under reduced pressure or other means. By this process, high-grade dialkyltin oxide can be obtained. The recovered mono- or trialkyl tin oxide is
It can be used as it is depending on the purpose, but as mentioned in the case of manufacturing trialkyltin oxide, after forming it into an alkyltin halide, it is reacted with tetraalkyltin or tin tetrahalide by a conventional method to obtain a high quality product. dialkyltin halide, which can be used again as a raw material.

〔Example〕

EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these in any way.

Example 1 I in a neck flask with an overflow nozzle on the side.
'A Equipped with a stirrer, a thermometer and a reflux condenser, 3850 g of a 20% caustic soda aqueous solution and 1990 g of tri-n-butyltin chloride containing 4.8% di-n-butyltin dichloride were continuously fed, and under stirring. The mixture was heated to 50° C. and a hydrolysis reaction was carried out for 30 minutes. The overflowing reaction solution was allowed to stand still. The contents are clearly separated into three phases,
The upper phase is a bis(tri-n-butyltin) oxide phase, the middle phase is an aqueous salt phase, and the lower phase is a bis(tri-n-butyltin).
It was a di-n-butyltin oxide phase containing 48% oxide, and its average particle size was 30 μm. The specific gravity of each phase was 1.1.1.2 and 1.3, respectively. Each layer was separated by liquid separation, the upper phase was dehydrated under reduced pressure, and then a small amount of precipitated salts was filtered to obtain 1629 g of bis(tri-n-butyltin) oxide. The analysis value by hydrochloric acid titration was 98.5%, and the theoretical yield from the raw material was 89.
It was 4%.

Example 2 Using the same equipment as in Example 1, 30% caustic potassium water solution 4
50g and di~n-phytyl S easy sifluoromide3.
300 g of tri-n-butyltin bromide containing 5% was continuously fed, and a hydrolysis reaction was carried out at 60° C. for 60 minutes with stirring. 260 g of water was added to the reaction product in order to adjust the specific gravity.

A sedimentation phenomenon similar to that in Example 1 occurred, and the reaction product was separated into three distinct phases. As a result of measuring the specific gravity of the aqueous phase, it was 1.2
It was 5. Thereafter, by performing the same operation as in Example 1, 224.4 g (yield: 92.8%) of bis(tri-n-butyltin) oxide was obtained from the uppermost phase. As a result of the analysis, the purity was 98.3%, and the dissolved di-n-butyltin oxide was 300 ppm, indicating high quality.

12.5 g of the bottom phase is 45 g of di-n-butyltin oxide.
%, and 50% bis(tri-n-butyltin) oxide. This was filtered under vacuum, and the cake was washed with toluene and dried to obtain white di-n-butyltin oxide. The average particle diameter was 70 μm, and the analysis value by acid titration was 99.2%. After combining the mother liquor and the washing liquid and distilling off toluene, bis(tri-n-butyltin) oxide was obtained as a residual aroma. As a result of analysis, the purity was 96.
It was 3%. The total yield from the raw materials was 98.1%.

Example 3 Using the same apparatus as in Example 1, 220 g of a 20% aqueous sodium hydroxide solution and di-n-octyltin diiodide 6 were added.
% of tri-n-octyltin iodide was continuously supplied, and a hydrolysis reaction was carried out at 70° C. for 60 minutes with stirring. As a result of adjusting the specific gravity by adding 50 g of toluene and 148 g of water to the reaction product, a sedimentation phenomenon similar to that in Example 1 occurred, and the reaction product was separated into three distinct phases. Thereafter, toluene is distilled off from the upper phase by normal operations, and bis(tri-n-octyltin) oxide 141
．． 0 g (yield 88.5%) was obtained.

As a result of analysis, it was found to be of high quality with a purity of 98.1%.

Comparative Example 1 A neck flask was equipped with a stirrer, a thermometer, and a reflux condenser, and 385 g of a 20% aqueous solution of caustic soda was charged at 50°C.
heated to. 200 g of tri-n-butyltin chloride containing 4.8% of di-n-butyltin dichloride was added dropwise over 30 minutes, and the reaction was then carried out at the same temperature for 1 hour. When left to stand still, it separated into an emulsified organic phase and an aqueous phase, with specific gravity of 1.15 and 1.2, respectively, but because the particle size of the di-n-butyltin oxide produced was very small, The interface exhibited an emulsion-like appearance, and the interface between the two phases was unclear, making it difficult to separate the two phases. The organic phase was a mixture of bis(tri-n-butyltin) oxide and di-n-butyltin oxide with an average particle size of 2 μm, and could not be separated by vacuum filtration as it was. 5 g of acid clay was added as a filter aid and filtered. Add 100g of water to the mother liquor and wash with water.
After separation, the organic phase was dehydrated under reduced pressure to obtain 167 g of bis(tri-n-butyltin) oxide. The analysis value by hydrochloric acid titration was 96.3%, and the yield from the raw material was 92%. In the cake separated as a mixture with acid clay,
The total amount of di-n-butyltin oxide produced in the reaction and approximately the same amount of bis(tri-n-butyltin) oxide are included, but no economical method has been found to separate and recover them. There wasn't.

Example 4 Using the same apparatus as in Example 1, 30% caustic potassium aqueous solution 1
075g and tri-n-butyltin bromide 1.8%
, 750 g of di-n-butyltin dipromide containing 1.5% mono-n-butyltin tribromide to 750 g of cyclohexane? The dissolved solution was continuously supplied, and the hydrolysis reaction was carried out at 70° C. for 45 minutes with stirring. 3,600 g of water was added to the overflowing reaction solution, and when it was left to stand, it separated into three distinct phases. The specific gravity of the three phases is 0.9.1.
1 and 1.3. The separated lower phase was washed with water and then dried under reduced pressure to obtain 445 g of white di-n-butyltin oxide. Purity by acid titration method is 99.8%
The average particle diameter was 50 μm. The intermediate aqueous phase is clear, and after neutralization with carbon dioxide gas, the precipitated white crystals are washed with water and dried to yield 5.5 g of mono-n-butyltin oxide.
I got it. Its purity was 96.1%. From the upper phase, 10.5 g of liquid bis(trilobyl)tin oxide was obtained as a residue after cyclohexane was distilled off, and its purity was 95.8%. The total yield of all butyltin oxide from the raw materials was 99.0%.

Example 5 A 16% caustic soda aqueous solution 13 was added to the same apparatus as in Example 1.
00g and tri-n-butyltin chloride 1.5%,
di-containing 1.0% mono-n-butyltin trichloride
1912g of n-butyltin dichloride was added to 359g of toluene.
A solution containing 2 g of the solution was continuously supplied, and a hydrolysis reaction was carried out at 75° C. for 60 minutes while stirring. When the overflowing reaction product was allowed to stand still, it clearly separated into three phases, each having a specific gravity of 0.9.1.1.1.2. After separating each of the three phases, the same treatment as in Example 4 was carried out, and from the lower phase to
-1520 g of butyltin oxide was obtained. Its purity is 9
The particle size was 9.8%, and the particle size was 80 μm.

2.6 g of mono-n-butyltin oxide (purity 95.9%) was obtained from the intermediate phase, and 5.9 g of bis(tri-n-butyltin) oxide (purity 95.6%) was obtained from the upper phase.
The total yield from the raw materials was 99.2%.

Comparative Example 2 For comparison, Example 5 was carried out using a conventional method. 130 g of 16% caustic soda aqueous solution/Fj was heated to 75°C, and di-n containing 1.5% of tri□-n-butyltin chloride and 1.0% of mono-n-butyltin trichloride was heated at the same temperature. −
A solution of 192 g of butyltin dichloride dissolved in 360 g of toluene was added dropwise over 2 hours, and hydrolysis was carried out under stirring. When it was allowed to stand still, it formed two phases and the interface was unclear. The organic phase was separated and di-n-butyltin oxide and toluene were separated by vacuum filtration. Filtration was very difficult and took 2 hours. The average particle diameter of the obtained white di-n-butyltin oxide was 8 μm. In order to remove a large amount of contaminating salts and bis(tri-n-butyltin) oxide, 200 g of toluene and 300 g of water were stirred, and after separation, an attempt was made to filter the organic phase, but filtration was almost impossible. .

〔Effect of the invention〕

According to the method of the present invention, the hydrolysis reaction product of an alkyltin halide clearly separates into three phases containing substantially solely mono-, di-, and trialkyltin oxides. The phase containing the target alkyltin oxide is easily separated by liquid separation, and a highly purified product can be easily obtained from each separated phase by a simple means. As a result, it has become possible to omit mechanical separation operations such as centrifugation and filtration, which were previously indispensable for separating mono-, di-, and tri-organotin oxides from hydrolysis reaction products. All problems related to occupational safety and health, environment, and economy will be resolved.

[Brief explanation of the drawing]

FIG. 1(a) is a flow sheet showing an outline of each step of the method of the present invention, and FIG. 1(b) is a flow sheet showing the outline of each step of the method of the present invention.
22 is a flow sheet showing an outline of the steps of the method described in Specification No. 22. Figure 2 shows bis(tri-n-butyltin) oxide and di-n-butyltin oxide separated and produced by the method of the present invention, in which the upper phase is an aqueous bis(tri-salt) phase and the lower phase is a substantially di-n-butyltin oxide. The concave surface indicates that the phase (W) is composed of n-butyltin oxide. Figure 3 shows di-n-butyltin oxide produced by the method described in U.S. Pat. No. 2,718,522.
Upper phase bis(tri-n-butyltin) oxide phase ([)
(The lower phase is a saline aqueous phase). FIG. 4 is a micrograph showing the particle structure of di-n-butyltin oxide separated and produced by the method of the present invention (magnification: 1
00 times). FIG. 5 is a micrograph (100x magnification) showing the particle structure of di-n-butyltin oxide produced by the method described in US Pat. No. 2,718,522.

Claims (1)

[Claims] (1) 1 to 5 mono-, di-, or trialkyl tin halide
Using a 0% basic substance aqueous solution, if the alkyltin oxide is solid, in the presence of a poorly water-soluble organic solvent with a boiling point of 150 ° C. or less at normal pressure and a specific gravity of 1.1 or less,
By subjecting the hydrolysis reaction continuously at a temperature of 30 to 100°C within 10 minutes to 3 hours, dialkyltin oxide with an average particle size of 10 μm or more is produced in the reaction product, and the resulting reaction product is left to stand still. By placing the oil in the water phase, three phases consisting essentially of dialkyltin oxide having a specific gravity difference of 0.02 or more are formed, and then from the oil phase separated by a liquid separation operation, Bis(trialkyltin) oxide or trialkyltin hydroxide, monoalkyltin oxide from an aqueous phase, and dialkyltin oxide from a phase substantially consisting of dialkyltin oxide having a specific gravity difference of 0.02 or more with respect to the aqueous phase. 1. A method for separating and producing an alkyltin oxide compound, which comprises isolating an alkyltin oxide compound.