DE2707765A1 - PROCESS FOR SEPARATING CONTAMINATION FROM FREE SULPHONIC ACID OR SULFURIC ACID - Google Patents

Description

KRAUS & WEISERT 27U7765 PATENT LAWYERS

DR. WALTER KRAUS DIPLOMA CHEMIST DR.-ING. TO NEKÄTE WEISERT DIPL-ING. SPECIALIZATION CHEMISTRY R Μ GAR D STRAS SE 15 · D-8OOO MUNICH 71 · TELEPHONE 089/79 70 77-79 70 78 · TELEX Ο5-212156 kpat d

TELEGRAM CRAUS PATENT

1471 WK / rm

NIPPON OIL COMPANY, LTD., Tokyo / Japan

Process for the separation of impurities from free sulfonic acid or sulfuric acid

The invention relates to a method for removing undesirable acidic substances from reaction mixtures, which occur in reactions that are catalyzed by cation exchange resins of the sulfonic acid type.

Many reactions are already known which are caused by ration exchange resins of the sulfonic acid type. They are used for the technical production of chemical

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bindings applied. These catalytic reactions become acidic substances such as free aromatic sulfonic acid or sulfuric acid found in the sulfonic acid type exchange resins are included, introduced into the reaction product as a result of extraction or release operations, which leads to difficulties.

This is often the case with processes for the industrial production of compounds by means of such catalytic reactions before that the reaction is carried out under such conditions that the unreacted starting mixture in the Reaction system present in a considerably high concentration in order to increase the speed of the reaction or to prevent side reactions. The resulting reaction mixture is converted into the desired end product and unreacted by distillation, extraction or adsorption Separated starting mixture, the latter being returned to the reaction system. When the reaction mixture, containing the sulfonic acid type cation exchange resin in such a separation step by distillation is to be separated, then a reverse reaction or another side reaction takes place due to the heating. If on the other hand the separation is effected by extraction or adsorption, then the acidic substances affect the Extractants or adsorbents.

Strongly acidic substances are generally neutralized with strongly basic substances such as sodium hydroxide, Calcium oxide or calcium hydroxide. However, it is difficult to use salts as a result of the neutralization reaction are formed to separate. In addition, the

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Amount of basic substances to be added is quite difficult to determine because of the concentration of the effluent Acid strong according to, for example, the type of catalyst, the reaction temperature, the type of raw material, the flow rate the acid flowing out and the reaction time varies.

It is also possible to use ordinary adsorbents capable of adsorbing acids, such as activated carbon, activated kaolin or silica-alumina. However, these adsorbents have only a low adsorption capacity. A reduction in the concentration of the acid to be adsorbed leads to a marked reduction the acid adsorption capacity of the adsorbents.

The object of the invention is therefore to provide a method in which the disadvantages of the known methods are overcome and that is capable of essentially completely removing undesirable acidic substances a reaction product mixture containing these impurities to remove.

It has now been found that hydrotalcite has excellent suitability for removing acidic substances from reaction mixtures, which occur in reactions which are catalyzed with cation exchange resins of the sulfonic acid type.

The invention therefore relates to a process for the separation of impurities from free sulfonic acid or sulfuric acid from reaction mixtures obtained in reactions carried out by sulfonic acid type cation exchange resins are catalyzed and which the reaction product,

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unreacted starting materials, free sulfonic acid or sulfuric acid as an impurity from the ion exchange resin and a reaction solvent if this is used, which is characterized in that the reaction mixture is contacted with hydrotalcite, in order to transfer the free sulfonic acid or sulfuric acid into the hydrotalcite that the reaction mixture, from which the free sulfonic acid or sulfuric acid has been removed, separates and that one wins this.

The method according to the invention is completely free of the disadvantages of the prior art methods described above Technology free. Sulfonic acid or sulfuric acid extracted from a sulfonic acid type cation exchange resin or has been released, is completely transferred into the hydrotalcite and removed from the reaction mixture. Consequently a reaction mixture can be obtained which does not contain any undesired sulfonic acid or sulfuric acid. as As a result, expenses in the stage of obtaining the reaction product and subsequent stages can be eliminated will.

The mechanism by which the acidic substances are removed from the cation exchange resin of the sulfonic acid type migrate from the reaction mixture into the hydrotalcite, is still not fully elucidated. However, it is believed that these acidic substances are either adsorbed on the hydrotalcite or react with it, or that both processes take place side by side.

Examples of sulfonic acid type cation exchange resins as contemplated herein are e.g.

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Styrene-derived sulfonic acid type resins and phenol sulfonic acid type resins. The ion exchange resins derived from styrene of the sulfonic acid type are obtained by sulfonating resins which are present in the copolymerization of styrene with a compound that has at least two ethylenically unsaturated groups in the molecule, for example from divinylbenzene, and which are commonly obtained Have units of the following formulas:

The phenolsulfonic acid type resins are usually thereby obtained by condensing phenolsulfonic acid with formaldehyde. They have the following chemical structure:

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"V

(In this, η means the degree of polymerization).

The hydrotalcite used according to the invention is also described as manassite. It represents a mineral from a hydrous basic carbonate of magnesium and aluminum with impurities. It occurs in nature for example in small quantities in the Urals region of the USSR. Hydrotalcite usually has the following chemical structure:

or

Mg ₆ Al ₂ (OH) ₁₆ CO ₃ .4H ₂ O Al ₂ O ₃ • 6MgO.CO ₂ • 12H ₂ O

However, hydrotalcite can also be produced synthetically. An example of a synthesis method is in Nippon, for example Kagaku Kaishi, Vol. 92, p. 514, 1971. at The procedure for this process is to use an aqueous aluminum sulfate solution or an aqueous solution of magnesium chloride or magnesium sulfate and an aqueous solution of sodium carbonate are introduced into a reactor, the mixture is stirred and further introducing sodium hydroxide into the reactor so that the pH of the solution is maintained at 10-11. By

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Varying the rate of addition of the aqueous aluminum sulfate solution and the aqueous magnesium salt solution can contain double oxides with varying Mg / Al ratios in the suspended state. The double oxides are collected by filtration, washed with water and calcined at 500 to 700 ° C, whereby synthetic hydrotalcites are obtained.

Hy * rotalcite usually has a magnesium / aluminum molar ratio of about 3. It is characterized by the following peaks in the X-ray diffraction pattern (JCPD 14-191).

dX 1 / I ₁ 7.69 100 3.88 70 2.58 20th 2.30 20th 1.96 20th 1.85 10 1.75 10 1.65 10 1.53 20th 1.50 20th 1.28 10

Rad. FeKa, λ 1.93728, filter Mn.

The X-ray diffraction pattern of the hydrotalcite is shown in the drawing.

Synthetic hydrotalcites have a magnesium / aluminum molar ratio from 1 to 10, with considerable swan

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sound of about 3 point. Even so, some of them have an X-ray diffraction pattern similar to that for hydrotalcite with a Magnesium / aluminum molar ratio of about 3 is characteristic. Such synthetic hydrotalcites lie even within the definition for the hydrotalcite used in the present invention if the magnesium / aluminum molar ratio deviates from about 3. All of these products can be used to treat acidic substances according to the Invention to remove.

There are no particular restrictions on the types of reactions that can be carried out with cation exchange resins from Sulfonic acid catalyzed to reaction mixtures supply, from which undesired acidic substances can be .entfernt by the method according to the invention.

Some examples of such catalytic reactions are given below:

(1) Production of ethers from olefinically unsaturated hydrocarbons and alcohols.

(2) Production of alcohols by hydration of olefinically unsaturated hydrocarbons.

(3) Production of ethers of polyhydric alcohols, in particular of glycol monoethers, from olefinic unsaturated hydrocarbons and polyhydric alcohols.

(4) Production of cyclic ethers by dehydrocyclization of diglycols.

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(5) Production of alkyl aromatics by alkylation of aromatic compounds.

(6) Oligomerization of olefinic hydrocarbons.

(7) Isomerization of olefinic hydrocarbons by shifting their unsaturation.

(8) Isomerization of hydrocarbons to produce products with a skeleton with a higher degree of crosslinking to deliver.

(9) Aldol condensation of ketones and / or aldehydes.

All of the above exemplified reactions are essentially essential on the catalytic effect of the sulphone group (R-SO, H) of the catalyst built up. As a result of the contacting of the starting materials with the catalyst liberated free aromatic sulfonic acid or sulfuric acid in the reaction mixture or extracted into this. The amount of undesirable acidic substances present in the reaction mixture varies depending on the reaction conditions, but is generally about 100 to about 1000 ppm.

Raw materials which are used in the above-exemplified reactions are, for example, the following toffe ^ö: Reaction (1): Olefinically unsaturated hydrocarbons having 2 to 22 carbon atoms, preferably 3 to 10 carbonic

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fuel atoms, such as propylene, η-butene, i-butene, pentene, Hexene or octene, and alcohols having 1 to 32 carbon atoms, preferably 1 to 20 carbon atoms, such as methanol, Ethanol, n-propanol, i-propanol, n-butanol, sec.-butanol, Hexanol, octanol and oleyl alcohol. Implementation (2): The same olefinically unsaturated hydrocarbons as in the implementation (1). Implementation (3): The same olefinically unsaturated hydrocarbons as in the implementation (1) and polyhydric alcohols having 1 to 32 carbon atoms, preferably 1 to 20 carbon atoms, such as Ethylene glycol, 1,2-propylene glycol, glycerin, diethylene glycol or triethylene glycol. Implementation (4): diglycols with 1 to 32 carbon atoms, preferably 1 to 20 carbon atoms, such as diethylene glycol, dipropylene glycol or dibutylene glycol. Implementation (5): monocyclic or polycyclic aromatic compounds with 6 to 30 carbon atoms, such as benzene, toluene, xylene, cumene, tetralin, naphthalene, Anthracene, trimethylbenzene or tetramethylbenzene. Examples of alkylating agents used in the reaction (5) are olefinically unsaturated hydrocarbons having 2 to 22 carbon atoms, preferably 3 to 15 carbon atoms, such as propylene, η-butene, i-butene, pentene, hexene, decene or dodecene, and saturated halides with 1 up to 22 carbon atoms, preferably 1 to 15 carbon atoms, such as methyl chloride, methyl bromide, ethyl bromide, propyl chloride, Butyl chloride and dodecyl chloride. Implementation (6): The same olefinically unsaturated hydrocarbons. Implementation (7): Olefinic hydrocarbons with 4 to 22 Carbon atoms, preferably 4 to 10 carbon atoms, such as butene-1, pentene-1, or heptene-1. Implementation (8): Aliphatic or alicyclic saturated hydrocarbons with

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2 7 U 7 7 6 p

A to 22 carbon atoms, such as butane, pentane, or heptane Decane, and various petroleum fractions that contain these substances, particularly petroleum fractions that are used for gasoline be used. Implementation (9): ketones or aldehydes with 1 to 20 carbon atoms, preferably 2 to 8 carbon atoms, such as acetaldehyde, acetone, propionaldehyde and butyraldehyde.

The reaction conditions differ depending on the type of reaction. In view of the catalytic nature of the cation exchange resins of the sulfonic acid, the reaction is usually carried out at 0 to 250 ⁰ C, preferably 50 to 150 ⁰ C, performed. Temperatures outside this range are not preferred, since none of the aforementioned reactions take place effectively ^{at temperatures below 0 ° C.} On the other hand, at temperatures higher than 250 ° C., the starting materials and the sulfonic acid type cation exchange resins may be decomposed. The reaction can be carried out under reduced pressure, but it is generally carried out at normal atmospheric pressure to a pressure of 50 atmospheres, preferably at a pressure of atmospheric pressure to 10 atmospheres.

The materials that are contacted with the catalyst can be in the form of a gas or a liquid. Preferably the catalyst is packed in the form of a sheet and the materials become in flowable form guided by this. But it can also be used a method in which the catalyst in the fluidized Materials is suspended, or a process in which the fluidized materials are contacted with the catalyst blown up by the materials.

7 U a 8 J b / U 7 Q Λ

27ÜV765

The reaction mixtures produced by the reaction (1) to make from olefinically unsaturated hydrocarbons and ethers To produce alcohols, the reaction (2) to make alcohols by hydration of olefinically unsaturated hydrocarbons to produce, and the reaction (3) to produce ethers of polyhydric alcohols from olefinically unsaturated hydrocarbons and producing polyhydric alcohols are particularly good as starting materials suitable for the process according to the invention in order to remove undesired acidic substances therefrom.

Examples of implementation (1) are the implementation for production of diisopropyl ether from propylene and isopropyl alcohol, the reaction for producing methyl isobutyl ether from isobutylene and methyl alcohol; and the reaction for producing of isopropyl tert-butyl ether from isobutylene and Isopropy] alcohol.

These reactions are carried out in a manner that is usually, contacted the starting materials with a cation exchange resin SuIfonsäuretyp, at a temperature of 20 to 200 ⁰ C, preferably 50 to 180 ⁰ C and a pressure of 0 to 50 atmospheres.

Such implementations are described, for example, in GB-PS 957 000 and in DT-OS 2 403 196.

Examples of the reaction (2) are the reaction for producing isopropyl alcohol by reacting propylene with water and the reaction to produce tert-butyl alcohol by reacting isobutylene with water.

7 0 9 H 5 K / U 7 0 J

These reactions are carried out in such a way that one the starting materials with a cation exchange resin of the sulfonic acid type, usually at a temperature of 50 to 200 ° C and a pressure of 0 to 50 atmospheres.

These reactions are described, for example, in DT-PS 2 147 737.

Examples of the reaction (3) are the reaction for the preparation of ethylene glycol monoisopropyl ether from propylene and ethylene glycol, the reaction to produce ethyl englycol monoisobutyl ether from isobutylene and ethylene glycol and the reaction for the production of diethylene glycol monoisopropyl ether from propylene and diethylene glycol.

These reactions are carried out in the manner that is commonly contacted the starting materials with a cation exchange resin SuIfonsäuretyp, at a temperature of 0 to 150 ° C, preferably from 30 to 120 ⁰ C and a pressure of 0 to 20 atmospheres.

These reactions are described, for example, in DT-OS 2 450 667.

In the catalytic reactions exemplified above, in which the process according to the invention can be used, is usually a mixture that contains the unreacted Contains materials and a reaction solvent (if used) and the desired reaction product, removed from the reaction zone in a form which contains undesirable acidic substances that result from the catalysis

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tor have been released or extracted. According to the invention, the reaction mixture described above can be used directly contacted with hydrotalcite. If desired, can before contacting with hydrotalcite, any substances which can be easily removed by simple measures, for example by leaving to stand, are removed. if the reaction mixture contains the catalyst as a solid, then this is preferably removed before contact with the hydrotalcite.

In a preferred contact method, the reaction mixture to be treated is passed through a layer covered with hydrotalcite, as in the case of the catalytic layer described above Reactions, is packed. The hydrotalcite can also be contacted in suspended form or in a form that is swirled up by the fluidized reaction mixture.

Hydrotalcite can be used as a powder or in the form of particles with a particle diameter of up to about 10 mm. For example, it can be used in the form of spheres or cylinders (extrudate). There are no particular restrictions on the temperature at which the reaction mixture is contacted with hydrotalcite. For example, contacting temperatures of approximately 0 to 300 ^° C., preferably 0 to 150 ^° C., can be used. According to the invention, the contacting of the reaction mixture with hydrotalcite leads to a transfer of almost all acidic substances from the reaction mixture to the hydrotalcite. The amount of hydrotalcite can be adjusted depending on the acid concentration of the acidic solution containing the acidic substances to be removed. In batch processes, hydrotalcite is usually used in amounts from 0.1 to

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50% by weight, preferably 1 to 20% by weight , are added to the acidic solution. In a continuous or flowing process, the acidic solution is passed at a rate of 1 to 1000 g, preferably 10 to 100, per 1 g of hydrotalcite per hour.

The invention is illustrated in the examples. example 1

90 g of a propylene / propane mixture containing 50% by weight of propylene were liquefied under pressure and mixed with 1 mol of isopropyl alcohol. To the resulting solution, 10 g of a sulfonic acid type cation exchange resin derived from styrene (Amberlist 15 »from Rohm & Haas) was added. The mixture was left to stand in a stirred reactor ^{at 100 ° C. for 1 hour.} After the reaction, the cation exchange resin was removed by filtration. In this way, a solution of isopropyl alcohol and diisopropyl ether was obtained. The acid concentration of this solution was 1.0 10 Aeg / 1. 10.0 g of powdered hydrotalcite (synthetic hydrotalcite with the composition Mg ^ Al ₂ (OIi ₁ g «CO, .4HpO) were added to this solution. The solution was stirred for 10 minutes. The hydrotalcite was then filtered off, whereby a neutral solution with an acid concentration of 1.2x10 "eq / l. Distillation of the resulting neutral solution yielded 48.5 g of diisopropyl ether having a purity of 99.796. Unreacted isopropyl alcohol was recovered from the bottom of the distillation tower.

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Example 2

1 mole of propylene and 1 mole of methanol were liquefied and mixed under pressure. To the resulting solution were 15 g of a phenolsulfonic acid type ion exchange resin (Amberllte IR-1) and the mixture was allowed to stir for 2 h Left 85 ° C in a stirred reactor. After the reaction, the cation exchange resin was filtered off. on in this way 70 g of a mixture of methanol and methyl isopropyl ether were obtained. The acid concentration of this Solution was 2.1 χ 10. 0.8 g of hydrotalcite (synthetic hydrotalcite with the composition Mg ^ AIp (OH) -Jg «CO about 0.8 mm and a mean length of about 1 mm. The solution was stirred for 30 minutes. Hydrotalcite was then filtered off and a neutral solution was obtained which had an acid concentration of 2.2 10 ** 'Xq / 1. Simple distillation of the resulting solution also yielded 55 g of methyl isopropyl ether a purity of more than 99.5%.

Example 3

The unreacted isopropyl alcohol, which in Example 1 was recovered was reacted again under the conditions given in Example 1. It wasn't Deterioration of the catalyst observed. The same results as in Example 1 were obtained.

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Example 4

A cylindrical reactor having an inner diameter of 5 cm and a height of 20 cm was charged with 200 g of the same sulfonic acid type cation exchange resin derived from styrene as used in Example 1, charged. A starting mixture of 1 mol of isopropyl alcohol and 140 g of mixed butylene, which contained isobutylene with a purity of 4096, in a liquefied state under pressure was passed at a flow rate of 2000 g / h at 50 ^° C. through the reactor which was packed with the cation exchange resin . The effluent from the reactor was passed through a neutralization pot which was filled with 20 g of the same hydrotalcite as used in Example 2. The neutralized effluent was then distilled.

In the above procedure, the conversion of isopropyl alcohol was 9896. It became isopropyl tertiary butyl ether obtained with a purity of more than 99.7%.

In the above process, the acid concentration of the effluent of the reaction x was prior to passage through the neutralization pot 3 10 "* eq / 1 and after passing χ 1.1 10 ~ ⁷ eq /. 1

Example 5

A starting mixture consisting of 62 g of ethylene glycol and 1 mole of isobutylene was liquefied under pressure and poured into a Initiated reactor which had previously been filled with 15 g of a cation exchange resin derived from styrene

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(The catalyst was prepared by sulfonating a copolymer of styrene and 5% divinylbenzene and was in the form of particles with a particle diameter of 0.84 to 0.297 mm). The mixture was stirred for 5 hours at 5O ⁰ C allowed to stand. The cation exchange resin was then removed. 5 g of the same hydrotalcite as used in Example 1 was added to the remaining solution at an acid concentration of 1.0 10 eq / l, and the solution was stirred for 30 minutes. Then hydrotalcite was separated and the remaining new

neutral solution with an acid concentration of 3.0 χ 10 * "'eq / 1 was distilled. The conversion of ethylene glycol was 9896. It was ethylene glycol mono- (tert-butyl) ether with a Obtained purity greater than 99%.

Example 6

A starting mixture consisting of 1 mole of propylene glycol and 1 mol of propylene was liquefied under pressure and introduced at 90 ° C. and a rate of 2000 g / h into a cylindrical reactor having an internal diameter of 5 cm and a height of 20 cm. This was dated from 220 g of a cation exchange resin derived from styrene Sulfonic acid type (the cation exchanger was made by sulfonating a copolymer of styrene with 10% Divinylbenzene was produced and was in the form of particles with a particle diameter of 0.84 to 0.297 mm before). The effluent from the reactor was passed through a cylindrical neutralization pot containing 100 g of des the same hydrotalcite as used in Example 2 was packed. The subsequent distillation yielded propylene

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glycol monoisopropyl ether with a purity of 99.5 %. The recovery ratio of the product was 98%.

In the above procedure, the acid concentration of the effluent from the reactor was 5 x 10 ** ^ Xq / l before Rapid evaporation, A χ 10 "^ Xq / l after the rapid evaporation

TJ

fung and 1.1 χ 10 "Xq / l after neutralization. Comparative example

As the reaction mixture obtained by the reaction described in Example 6 without treatment was distilled with hydrotalcite, the yield rate of propylene glycol monoisopropyl ether formed as a result of the reaction was only 1796.

As a result of the distillation, there was about 4.8 moles of propylene obtained per mole of propylene glycol monoisopropyl ether recovered from the top of the distillation tower. At the bottom of the tower Propylene glycol was deposited in an amount almost equimolar to that of propylene.

Example 7

A starting mixture consisting of 1 mole of propylene and 20 moles of water was used at a flow rate of 300 g / h at 100 to 120 ° C through a cylindrical reactor with an internal diameter of 5 cm and a height of 20 cm passed, which had been packed with 220 g of the same cation exchange resin as used in Example 1 had been. The reaction solution had an acid concentration

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tion of 2.5 x 10 eq / 1. The reaction solution was with a flow rate of 2000 g / h through a cylindrical neutralization pot filled with 100 g of the same Hydrotalcite was packed, as it had been used in Example 2, passed. The acid concentration of the resulting solution was 1.6 10 "eq / l.

Example 8

A 200 ml stainless steel vessel equipped with a stirrer was charged with 80 g of diethylene glycol and 30 g of a sulfonic acid type cation exchange resin (Amberlist 15) derived from styrene. The reaction was carried out for 10 hours with stirring and at 130 ⁰ C. After the reaction, the reaction solution was filtered to remove the cation exchange resin. The resulting solution had an acid concentration of 5.7 x 10 eq / l. To the resulting solution, 10.0 g of the same hydrotalcite as used in Example 1 was added, and the solution was stirred for 15 minutes. The hydrotalcite was then removed by filtration, whereby a neutral solution was obtained which had an acid concentration of 1.1 10 'eq / l. The distillation of the resulting neutral solution yielded 52 g of p-dioxane with a purity of 99,

Example 9

A 200 ml glass flask fitted with a reflux condenser and was provided with a styrene 20 g of a sulfonic acid type cation exchange resin (Amberlist 15) and 60 g of p-xylene. Propylene

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gas was bubbled into the solution through a sparger at a flow rate of 400 ml / min and 3 hours long implemented. After the reaction, the reaction mixture was filtered to remove the cation exchange resin. As a result, 2,5-diisopropyl-1,4-dimethylbenzene was obtained in a yield of 9996 and a p-xylene conversion of 100%. The resulting solution had an acid concentration of 2.5 x 10 eq / 1. 5.0 g of the same hydrotalcite as used in Example 1 were added to this solution. The solution was for 15 minutes touched. The hydrotalcite was filtered off. It became a neutral solution with an acid concentration of 1.5 x 10 Eq / 1 obtained.

Example 10

A 1-1 stainless steel vessel fitted with a stirrer, was mixed with 125 g of a sulfonic acid type cation exchange resin (Amberlist-15) derived from styrene, 195 g Benzene and 86 g of a mixture of n-01efinen with 10 to 14 carbon atoms charged. The reaction. Was taking Stirring carried out at 120 ° C. for 6 hours. After the reaction, the reaction mixture was filtered to remove the cation exchange resin. A chromatographic analysis of the resulting solution indicated that 88.5% of the starting n-olefin mixture had been converted to alkylbenzenes. This solution had an acid concentration of 3.0 10 eq / l. 15.0 g of the same hydrotalcite as used in Example 1 were added to the solution, and the solution was stirred for 30 minutes. Then hydrotalcite was filtered off

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triert, creating a neutral solution with an acid concentration of 1.3 x 10 "eq / 1 was obtained.

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Claims (6)

Claims K ^ _X * s process for the separation of impurities from free sulfonic acid or sulfuric acid from reaction mixtures which are obtained in reactions which are catalyzed by cation exchange resins of the sulfonic acid type and which contain the reaction products unreacted starting materials, free sulfonic acid or sulfuric acid as an impurity from the ion exchange resin as well contain a reaction solvent, if this is used, characterized in that the reaction mixture is contacted with hydrotalcite in order to transfer the free sulfonic acid or sulfuric acid into the hydrotalcite, that the reaction mixture from which the free sulfonic acid or sulfuric acid has been removed, separates and that one wins this. 2. The method according to claim 1, characterized in that the unreacted starting materials and / or the reaction solvent is at least partially removed by stripping before the reaction mixture is brought into contact with hydrotalcite. 3. The method according to claim 1, characterized in that the amount of free sulfonic acid or sulfuric acid contained in the reaction mixture is 100% is up to 1000 ppm. 4. The method according to claim 1, characterized in that the reaction product is an aliphatic 709836/0703 ORIGINAL INSPECTED shear ether is formed by reacting an ethylenically unsaturated aliphatic hydrocarbon with 2 to 22 carbon atoms with an aliphatic monohydric alcohol having 1 to 32 carbon atoms is. 5. The method according to claim 1, characterized in that the reaction product is a glycol monoether is, the reaction of an ethylenically unsaturated aliphatic hydrocarbon with 2 to 22 Carbon atoms with an aliphatic glycol having 1 to 32 carbon atoms. 6. The method according to claim 1, characterized in that the reaction product is an aliphatic is monohydric alcohol, which is obtained by reacting an ethylenically unsaturated aliphatic hydrocarbon with 2 to 22 carbon atoms has been obtained with water. 709836/0703