JP5763734B2 - Method for producing polyoxyalkylene monool or polyol - Google Patents

Description

  The present invention relates to a method for producing a polyoxyalkylene monool or polyol.

  Polyoxyalkylene monools or polyols are used as polyurethane raw materials, cosmetic raw materials, and surfactants. This polyoxyalkylene monool or polyol is produced by adding an alkylene oxide to an active hydrogen group-containing compound such as alcohol, glycol, polyfunctional alcohol or amine compound. In this addition reaction, an alkali metal compound such as potassium hydroxide or a Lewis acid such as boron trifluoride is usually used as a catalyst.

  Among them, polyoxyalkylene monools or polyols produced using a Lewis acid catalyst may contain or release cyclic ethers such as dioxane and low-boiling volatile components such as low-molecular aldehydes as by-products. Are known. Polyurethane resins, cosmetics and surfactants produced using these have the problem of generating unpleasant odors.

  As a solution, it is known that the use of a specific Lewis acid catalyst can reduce odor (see Patent Document 1), but the effect of reducing odor is insufficient. In addition, odor can be further reduced by addition polymerization of an active hydrogen-containing compound with an alkylene oxide while continuously or intermittently removing a by-product low-boiling compound in the presence of a Lewis acid catalyst. Has been proposed (see Patent Document 2), but its effect is insufficient from the viewpoint of suppressing the generation of odor over time due to long-term storage. On the other hand, it has been proposed to reduce odors by distilling water and volatile substances while adding water to polyoxyalkylene polyol in the form of extremely small liquid particles (see Patent Document 3). However, the method of Patent Document 3 is intended to efficiently remove odor-causing substances present in a released state in a polyol by azeotropic action with water. It is insufficient to inactivate potential odor-causing substances that can generate odors. Therefore, although the method of Patent Document 3 gives a substantially odorless polyoxyalkylene polyol immediately after purification, the effect is insufficient from the viewpoint of suppressing the generation of odor over time due to long-term storage.

JP 2003-183383 A JP 2009-227978 A JP-A-9-59374

  An object of the present invention is to provide a method for producing a polyoxyalkylene monool or polyol which has no unpleasant odor and does not generate odor even after long-term storage.

As a result of intensive studies, the present inventor has reached the present invention.
That is, the method for producing the polyoxyalkylene monool or polyol of the present invention comprises at least one element (a1) selected from the group consisting of boron, aluminum, tin, antimony, iron, phosphorus, zinc, titanium, zirconium and beryllium. In the presence of at least one acidic catalyst (x1) selected from the group consisting of a halide of the above, an alkylated product of the element (a1), and a phenylated product of the element (a1), an alkylene oxide ( The polyoxyalkylene monool or polyol obtained by addition polymerization of d) is used without removing water and the acidic catalyst (x1) as they are, or further, Lewis acid or Bronsted acid is added. in a one of an acidic catalyst (x2) is either one, acidic catalyst (x2) Weight in the presence and pressure of the active hydrogen-containing compound (c) and the acid catalyst is 0.00001% by weight relative to the total weight of the alkylene oxide (d) (x2), at 100 ° C. to 180 ° C. After the treatment, the gist is to remove the volatile component under reduced pressure and not to remove the residue of the acidic catalyst (x2) .

  According to the production method of the present invention, it is possible to produce a polyoxyalkylene monool or polyol having a very low odor and no deterioration over time and a very low odor over the long term.

The present invention is described in detail below.
In the production method of the present invention, the alkylene oxide (d) is addition-polymerized to the active hydrogen-containing compound (c) in the presence of the Lewis acid catalyst (a).
In the present invention, the Lewis acid catalyst (a) used at the time of addition of the alkylene oxide (d) is not particularly limited as long as it is an acidic catalyst for ring-opening addition polymerization of a cyclic ether, but boron, aluminum, tin, antimony, iron, Examples include acidic catalysts containing at least one element (a1) selected from the group consisting of phosphorus, zinc, titanium, zirconium and beryllium.
Examples of the acidic catalyst containing the element (a1) include a halide of the element (a1) and an alkylated and / or phenylated product of (a1), and two or more kinds may be used in combination. Specific examples include the following.
(I) Halide of element (a1) Boron compounds such as boron trifluoride and boron trichloride; Aluminum compounds such as aluminum chloride and aluminum bromide; Tin compounds such as tin tetrafluoride and tin tetrachloride; Antimony fluoride And antimony compounds such as antimony chloride; iron compounds such as ferric chloride; phosphorus compounds such as phosphorus pentafluoride; zinc compounds such as zinc chloride; titanium compounds such as titanium tetrachloride; zirconium compounds such as zirconium chloride; (Ii) Alkylation and / or phenylation of element (a1) Triphenylboron, tri (t-butyl) boron, tris (pentafluorophenyl) boron, bis (pentafluorophenyl) -t- Butyl boron, bis (pentafluorophenyl) boron fluoride, di (t-butyl) Boron compounds, boron compounds such as (pentafluorophenyl) boron difluoride; triethylaluminum, triphenylaluminum, diphenyl-t-butylaluminum, tris (pentafluorophenyl) aluminum, bis (pentafluorophenyl) -t-butylaluminum Aluminum compounds such as bis (pentafluorophenyl) aluminum fluoride, di (t-butyl) aluminum fluoride, (pentafluorophenyl) aluminum difluoride and (t-butyl) aluminum difluoride; zinc such as diethyl zinc Compound; etc.

  Among these (i) and (ii), from the viewpoint of the reactivity during addition polymerization and the reactivity of the produced alkylene oxide adduct, boron trifluoride and the alkylated and / or phenylated product of element (a1) are Preferred are boron trifluoride, tris (pentafluorophenyl) borane and tris (pentafluorophenyl) aluminum, and particularly preferred are tris (pentafluorophenyl) borane and tris (pentafluorophenyl) aluminum.

  In the present invention, examples of the active hydrogen-containing compound (c) include compounds having a hydroxyl group, a carboxyl group, an amino group, a thiol group, and an acid amide group. Moreover, the compound (alkylene oxide adduct) of the structure where the below-mentioned alkylene oxide (d) was added to the compound (Water, alcohol, an amino group containing compound, carboxylic acid, etc.) which has active hydrogen is mentioned. Two or more of these may be used in combination. The alkylene oxide adduct used as the hydroxyl group-containing compound may be obtained using a catalyst other than the Lewis acid catalyst (a). Specific examples of the active hydrogen-containing compound (c) include the following (c1) to (c7). These may be one kind or a combination of two or more kinds.

(C1) Water (c2) Alcohol As the monohydric alcohol, an alcohol having 1 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and alkylene oxide adducts thereof. For example, methanol, ethanol, n-propanol, 2-propanol, n-butanol, 2-ethylhexanol, n-octanol, decyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, octadecyl alcohol , Diethylene glycol monomethyl ether, tripropylene glycol monomethyl ether, and alkylene oxide adducts thereof.
The dihydric alcohol includes a dihydric alcohol having 2 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and alkylene oxide adducts thereof, and ethylene glycol. , Propylene glycol, 1,3-propanediol, 1,4-butanediol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, and alkylene oxide adducts thereof.
Examples of the trihydric alcohol include trivalent alcohols having 3 to 80 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and alkylene oxide adducts thereof, glycerin, Examples include trimethylolpropane, triethanolamine, and alkylene oxide adducts thereof.
The 4- to 8-valent alcohol includes a 4- to 8-valent alcohol having 5 to 80 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and these alkylene oxide adducts. And pentaerythritol, sorbitol, xylit, mannitol, dipentaerythritol, glucose, fructose, sucrose and alkylene oxide adducts thereof.

(C3) Phenol Monohydric phenol includes monohydric phenol having 6 to 40 carbon atoms, and examples thereof include phenol and cresol. The polyhydric phenol includes polyhydric phenol having 6 to 40 carbon atoms, and examples include pyrogallol, catechol, hydroquinone, and bisphenol A.

(C4) Carboxylic acid The monovalent carboxylic acid includes a monovalent carboxylic acid having 1 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, formic acid, Examples include acetic acid, propionic acid, butyric acid, octanoic acid, lauric acid, oleic acid, and linoleic acid. Examples of the divalent carboxylic acid include divalent carboxylic acids having 4 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic, and aromatic, and include maleic acid, amber, and adipine. Examples include acid and phthalic acid. Examples of the 3 to 8 carboxylic acid include 3 to 8 carboxylic acid having 6 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and acrylic acid. A 3-8 mer etc. are mentioned.

(C5) Amine Monovalent amines include monovalent amines having 2 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and include diethylamine, diisopropylamine and And dioleylamine. Examples of the divalent amine include divalent amines having 1 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, methylamine, ethylamine, propylamine and n -Butylamine etc. are mentioned. Examples of the trivalent to pentavalent amine include ammonia and a trivalent to pentavalent amine having 2 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic. -Methylaminoethylamine, ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine and the like.
In addition, the valence of an amine means the number of active hydrogen which an amine has.

(C6) Thiol The thiol includes monovalent and polyvalent thiols having 1 to 80 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic, and the above (c2) 1-5 functional thiol obtained by the reaction of 1-5 pentahydric alcohol and thiourea, and 1-5 functional thiol obtained by the reaction of epichlorohydrin or 2-5 mer of epichlorohydrin and sodium hydrosulfide, etc. Can be mentioned.
(C7) Acid amide Examples of the acid amide include monovalent and polyvalent acid amides having 1 to 40 carbon atoms selected from the group consisting of linear, branched, saturated, unsaturated, alicyclic and aromatic. Examples thereof include dimers and pentamers of acid amides and unsaturated monocarboxylic acid amides (monocarboxylic acid amides such as acrylamide and methacrylamide).

  Among the active hydrogen-containing compounds (c), from the viewpoint of easy availability, the compounds (c1) to (c7) are preferable, more preferably (c1) to (c3), and particularly preferably (c2). is there. From the viewpoint that the viscosity of the resulting polyoxyalkylene monool or polyol does not become too high and is easy to handle, the number of active hydrogens in (c) is preferably 1-8, more preferably 1-4.

  Examples of the alkylene oxide (d) include ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, styrene oxide, cyclohexene oxide, epichlorohydrin, and glycidyl ether. Of these, ethylene oxide, propylene oxide, and mixtures thereof are preferable from the viewpoint of reactivity. The alkylene oxide (d) may be one type or a combination of two or more types. The addition reaction may be random addition or block addition.

  The number of moles of alkylene oxide (d) added to the active hydrogen-containing compound (c) is 0.5 to 300 with respect to 1 mole of active hydrogen from the viewpoint of easy removal of the by-product low-boiling compound (b). Mole is preferable, more preferably 0.7 to 150 mol, and particularly preferably 1 to 50 mol.

  The amount of (a) used when adding alkylene oxide (d) to active hydrogen-containing compound (c) in the presence of Lewis acid catalyst (a) is determined from the viewpoint of the reactivity of addition polymerization. Based on the weight of the adduct, it is preferably 0.00001 to 10% by weight, more preferably 0.0001 to 1% by weight.

In the method for producing a polyoxyalkylene monool or polyol of the present invention, the polyoxyalkylene mono obtained by addition polymerization of an alkylene oxide (d) to an active hydrogen-containing compound (c) in the presence of a Lewis acid catalyst (a). The oar or polyol is treated at 100-180 ° C. in the presence of water and acid and under pressure.
The production method of the present invention includes a step of mixing and reacting a Lewis acid catalyst (a), an active hydrogen group-containing compound (c) and an alkylene oxide (d) (step 1), and then a polyoxyalkylene monool or polyol. Water is added to the mixture to be processed, and a polyoxyalkylene monool or polyol is produced through a process of removing volatile components at 100 ° C. to 180 ° C. and under reduced pressure in the presence of an acid and under pressure (step 2). The method is preferably exemplified.

  In step 1, the mixing method of the Lewis acid catalyst (a), the active hydrogen group-containing compound (c) and the alkylene oxide (d) is not particularly limited. For example, the Lewis acid catalyst (a) is added to the active hydrogen group-containing compound (c). And a method of adding alkylene oxide (d). The method for adding the Lewis acid catalyst (a) is not particularly limited. For example, (a) alone may be added, or a solution of an inert solvent such as toluene or hexane may be added. It may be added after mixing with (d). In addition, (a) may be added all at once, or may be added in multiple portions. The addition method of alkylene oxide (d) is not specifically limited, The whole quantity may be added at once, and you may divide and add in multiple times. A block copolymer can also be obtained by sequentially adding different types of alkylene oxide (d) and completing the polymerization reaction each time it is added. The order of adding the Lewis acid catalyst (a) and the alkylene oxide (d) is not particularly limited, and either one may be added first or simultaneously.

  The conditions for the polymerization may be determined according to the types of the active hydrogen group-containing compound (c) and alkylene oxide (d), the type and amount of Lewis acid catalyst (a) used, the target molecular weight, and the like. The pressure at the time of superposition | polymerization can be performed on the conditions of the addition reaction of the conventional alkylene oxide. The temperature during the polymerization is preferably 0 to 180 ° C., more preferably 20 to 160 ° C. from the viewpoint of the thermal stability of the Lewis acid catalyst (a) to be used.

  After addition of the predetermined alkylene oxide (d), in step 2, the polyoxyalkylene monool or polyol is treated in the presence of water and acid and under pressure. The temperature of a process is 100 to 180 degreeC, Preferably it is 105 to 170 degreeC. When processing temperature is lower than 100 degreeC, a long-term odor suppression effect will become inadequate. Moreover, when it exceeds 180 degreeC, the polyoxyalkylene monool or polyol obtained will cause quality changes, such as coloring.

  In this treatment, it is essential to treat in the presence of a small amount of water. The amount of water used is 0.5 to 20 with respect to the total weight of the active hydrogen group-containing compound (A) and alkylene oxide (B) used in the reaction, from the viewpoint of long-term odor suppression effect and dehydration efficiency. % By weight is preferred, more preferably 1 to 10% by weight. The method of adding water is not particularly limited, and the whole amount may be added at once, or may be added in a plurality of divided portions.

  It is essential to perform the treatment in Step 2 in the presence of an acid. As the acid, the Lewis acid catalyst (a) used for the addition polymerization of alkylene oxide can be used without being removed, and a small amount of acid may be added separately. Examples of the acid to be added include Lewis acid and Bronsted acid.

Examples of the Lewis acid to be added include a Lewis acid catalyst (a) used for addition polymerization.
Examples of the Bronsted acid to be added include mineral acids represented by sulfuric acid, hydrochloric acid, and phosphoric acid, and organic acids represented by carboxylic acids and alkylsulfonic acids.
As the acid to be added, Lewis acid catalyst (a) and phosphoric acid are preferable from the viewpoint of the odor suppressing effect and ease of handling. These may be used alone or in combination of two or more. The method for adding the acid is not particularly limited, and for example, it may be added alone or as a solution of an inert solvent such as toluene or hexane. In addition, the acid may be added all at once, or may be added in multiple portions. There is no restriction | limiting in particular in the addition order of an acid and water, either one may be added first and you may add simultaneously.

  The total amount of acid to be added (including the Lewis acid catalyst (a) used in the addition polymerization) is the active hydrogen group used in the reaction from the viewpoint of treatment efficiency for odor control and prevention of adverse effects on product quality of the catalyst residue. 0.00001-10 weight% is preferable with respect to the total weight of a containing compound (A) and alkylene oxide (B), More preferably, it is 0.0001-1 weight%.

  The process in step 2 is performed under pressure. The pressure only needs to be a pressure at which water can exist in a liquid state during the treatment (that is, a pressure equal to or higher than the vapor pressure of water at the treatment temperature). . Moreover, from a viewpoint of the availability of a pressure vessel, the pressure is preferably 0.12 to 4 MPa.

  The treatment time after adding a small amount of water is preferably from 0.1 to 5 hours, more preferably from 0.2 to 4 hours, from the viewpoint of long-term odor suppression effect and production efficiency.

  According to the production method of the present invention, the low-boiling volatile substances that are by-produced during the reaction and cause odor are liberated from the polyoxyalkylene monool or polyol by the above treatment, and these are easily removed. it can.

  The liberated low-boiling volatile substances and water are preferably removed under reduced pressure. The temperature at the time of removal is preferably 100 ° C to 180 ° C, more preferably 105 ° C to 170 ° C. The pressure at the time of removal is preferably performed under a reduced pressure of 0.001 to 0.99 MPa. Furthermore, water can be added to make the removal under reduced pressure more efficient. The amount of water added is 0.5 to 20 from the viewpoint of the low boiling point volatile substance and the efficiency of distilling water with respect to the total weight of the active hydrogen group-containing compound (A) and alkylene oxide (B) used in the reaction. % By weight is preferred, more preferably 1 to 10% by weight. The method of adding water is not particularly limited, and the whole amount may be added at once, or may be added in a plurality of divided portions.

  The polyoxyalkylene monool or polyol obtained by the production method of the present invention has very little odor and can be maintained even during long-term storage.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. Hereinafter, unless otherwise specified, parts means parts by weight.

In addition, the odor evaluation of the obtained polyoxyalkylene monool or polyol was carried out by sensory evaluation based on the following criteria with 10 monitors. The evaluation criteria are as follows. The average value of 10 people (rounded to the first decimal place) was used as the odor evaluation.
4 points: Almost no odor 3 points: Slight odor 2 points: Slightly unpleasant odor 1 point: Unpleasant odor

  Further, the quantification of volatile components contained in the polyoxyalkylene monool or polyol (propionaldehyde content and the total amount of compounds that easily volatilize under the following heat retaining conditions) was analyzed by headspace gas chromatography. In the measurement, the vial was kept at a temperature of 70 ° C., and the vial was kept at a temperature of 30 minutes.

<Example 1>
An autoclave was charged with 400 parts of a propylene oxide adduct of glycerin (hydroxyl value 280) and 0.09 part of tris (pentafluorophenyl) borane, and then charged while controlling the propylene oxide reaction temperature at 70 to 75 ° C. . However, propylene oxide was charged 20 times, and after 10 minutes, the process of distilling off low-boiling volatile components under reduced pressure (0.01 MPa) for 15 minutes was repeated. After charging until the amount of liquid in the autoclave reached 2000 parts, the mixture was aged at the same temperature for 3 hours. After 100 parts of water and 0.03 part of tris (pentafluorophenyl) borane were added at the same time, the temperature was raised to 140 ° C., treated for 30 minutes at a pressure of 0.60 MPa, and reduced pressure (0.01 MPa) at the same temperature. The volatile component was distilled off for 2 hours to obtain a liquid polyoxyalkylene polyol (A-1). The odor evaluation was 4, the propionaldehyde content was 10 ppm, and the total amount of easily volatile compounds was 65 ppm.

<Example 2>
In Example 1, a liquid polyoxyalkylene polyol (A-2) was prepared in the same manner as in Example 1 except that 0.015 part of phosphoric acid was used instead of 0.03 part of tris (pentafluorophenyl) borane. Got. The odor evaluation was 4, the propionaldehyde content was 8 ppm, and the total amount of easily volatile compounds was 61 ppm.

<Example 3>
A liquid polyoxyalkylene polyol (A-3) was obtained in the same manner as in Example 1 except that 0.03 part of tris (pentafluorophenyl) borane was not added. The odor evaluation was 4, the propionaldehyde content was 12 ppm, and the total amount of easily volatile compounds was 72 ppm.

<Example 4>
In Example 1, it replaced with 100 parts of water, and except using 400 parts of water, operation similar to Example 1 was performed and the liquid polyoxyalkylene polyol (A-4) was obtained. The odor evaluation was 4, the propionaldehyde content was 8 ppm, and the total amount of easily volatile compounds was 60 ppm.

<Example 5>
In Example 1, it replaced with 100 parts of water, and except having used 20 parts of water, operation similar to Example 1 was performed and the liquid polyoxyalkylene polyol (A-5) was obtained. The odor evaluation was 3, the propionaldehyde content was 20 ppm, and the total amount of easily volatile compounds was 112 ppm.

<Example 6>
In Example 2, it replaced with 100 parts of water, and except using 40 parts of water, operation similar to Example 2 was performed and the liquid polyoxyalkylene polyol (A-6) was obtained. The odor evaluation was 4, the propionaldehyde content was 9 ppm, and the total amount of easily volatile compounds was 64 ppm.

<Example 7>
In Example 1, instead of heating to 140 ° C. and treating for 30 minutes at a pressure of 0.60 MPa, Example 1 was carried out except that the temperature was raised to 105 ° C. and treated for 2 hours at a pressure of 0.12 MPa. The same operation was carried out to obtain a liquid polyoxyalkylene polyol (A-7). The odor evaluation was 4, the propionaldehyde content was 14 ppm, and the total amount of easily volatile compounds was 87 ppm.

<Example 8>
A liquid polyoxyalkylene polyol (A-8) was obtained in the same manner as in Example 1 except that the treatment was performed under a pressure of 0.30 MPa in place of the pressure of 0.60 MPa. It was. The odor evaluation was 3, the propionaldehyde content was 25 ppm, and the total amount of easily volatile compounds was 98 ppm.

<Comparative Example 1>
A liquid polyoxyalkylene polyol (B-1) was obtained in the same manner as in Example 1, except that the operation for 30 minutes under the pressure of 0.60 MPa was not performed in Example 1. The odor evaluation was 3, the propionaldehyde content was 28 ppm, and the total amount of easily volatile compounds was 136 ppm.

<Comparative Example 2>
In Example 1, except having processed at 90 degreeC instead of 140 degreeC, operation similar to Example 1 was performed and the liquid polyoxyalkylene polyol (B-2) was obtained. The odor evaluation was 3, the propionaldehyde content was 30 ppm, and the total amount of easily volatile compounds was 144 ppm.

<Comparative Example 3>
In Example 3, before adding water, 5 parts of hydrotalcite-based adsorbent (KYOWARD 500) was added and stirred at 75 ° C. for 30 minutes, followed by filtration with filter paper to remove the acid catalyst. The same operation was performed to obtain a liquid polyoxyalkylene polyol (B-3). The odor evaluation was 3, the propionaldehyde content was 34 ppm, and the total amount of easily volatile compounds was 148 ppm.

  About the polyoxyalkylene polyol obtained in Examples 1-8 and Comparative Examples 1-3, the thermal stability test was done and the content of the odor after a test and a volatile component was analyzed. The results are shown in Table 1. The conditions for the thermal stability test are as follows.

[Conditions for thermal stability test]
200 mL of polyoxyalkylene polyol was put into a 220 mL glass container, the space inside the glass container was sealed with nitrogen, sealed, and stored in a thermostat at 50 ° C. for 90 days.

  As is clear from Table 1, the polyoxyalkylene polyols obtained in Examples 1 to 8 of the present invention have reduced odor and volatile component content immediately after production in comparison with Comparative Examples 1 to 3. It can be seen that there is almost no increase after the thermal stability test.

  Since the polyoxyalkylene monool or polyol obtained by the production method of the present invention does not generate an unpleasant odor over a long period of time, it is suitable for polyurethane raw materials, cosmetic raw materials, surfactants and the like.

Claims (2)

A halide of at least one element (a1) selected from the group consisting of boron, aluminum, tin, antimony, iron, phosphorus, zinc, titanium, zirconium and beryllium, an alkylated product of element (a1), and element (a1) A polyoxyalkylene monool or polyol obtained by addition polymerization of an alkylene oxide (d) to an active hydrogen-containing compound (c) in the presence of at least one acidic catalyst (x1) selected from the group consisting of phenylated compounds , water and either an acid catalyst (x1) are those used without directly removed, or even of an acidic catalyst (x2) is either one in which the addition of a Lewis acid or Bronsted acid The weight of the acidic catalyst (x2) is based on the total weight of the active hydrogen-containing compound (c) and the alkylene oxide (d). In the presence and pressure of 0.00001% by weight and is acidic catalyst (x2), was treated with 100 ° C. to 180 ° C., the volatiles removed under reduced pressure, the residue of an acid catalyst (x2) A method for producing a polyoxyalkylene monool or polyol which is not removed . The method for producing a polyoxyalkylene monool or polyol according to claim 1, wherein the alkylene oxide (d) is propylene oxide, ethylene oxide or a mixture thereof.