JP2005350402A - Monohydric alcohol alkylene oxide adduct and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a highly pure monohydric alcohol alkylene oxide adduct having a high mol. wt. diol content reduced to a level having no problem in practical applications, and to provide a method for producing the same. <P>SOLUTION: This monohydric alcohol alkylene oxide adduct (A) represented by the general formula (2): RO-(AO)m/(EO)n-H (2) [R is a 1 to 24C aliphatic hydrocarbon group or the like; A is a 3 to 8C alkylene; E is ethylene; (m) is 0 or an integer of 1 to 400; (n) is 0 or an integer of 1 to 400; (m)+(n) is 1 to 400] is characterized by satisfying the following relational expression (1) : 1.18≥A/(H×ΔM) (1) (L is a straight line obtained by binding an elution-starting point to an elution-finishing point; H is a height from the apex of the maximum peak to L; ΔM is a half-value width; A is the total peak area) in a chromatogram obtained with GPC, and a method for producing the same. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a monohydric alcohol alkylene oxide adduct.

Aliphatic alcohol alkylene oxide adducts obtained by addition polymerization of alkylene oxides to aliphatic alcohols in the presence of basic catalysts or acidic catalysts are known as various surfactants, solvents, chemical intermediates, etc. ing.
The monohydric alcohol alkylene oxide adduct is produced by subjecting a monohydric alcohol to an addition reaction of alkylene oxide in the presence of an alkali catalyst. At this time, if a substance having two hydroxyl groups per molecule such as water is present in the reaction system, alkylene oxide is added to the water molecule, and a diol component having a molecular weight approximately twice that of the target product is by-produced. For this reason, the manufacturing method of the alkylene oxide adduct of the monohydric alcohol which controlled the water | moisture content in the reaction system is proposed (for example, patent document 1).
Japanese Patent No. 3050228

  However, even if the water content in the reaction system is controlled, a high-molecular-weight diol component is produced as a by-product, causing a problem depending on the application, which is insufficient in practice. A highly pure monohydric alcohol alkylene oxide adduct having a high molecular weight diol component reduced to a level causing no practical problem and a method for producing the same have been desired.

As a result of intensive studies to solve the above problems, the present invention has been achieved.
That is, in the present invention, in the chromatogram obtained by GPC, L is a straight line connecting from the elution start point to the elution end point, H is the height from the apex of the maximum peak, L is the half width, and ΔM is the total peak area. The monohydric alcohol alkylene oxide adduct (A) represented by the general formula (2) characterized by satisfying the following relational expression (1) when A is assumed;
Relational expression
1.18 ≧ A / (H × ΔM) (1)
General formula
RO- (AO) m / (EO) n-H (2)
(In the formula, R represents an aliphatic hydrocarbon group having 1 to 24 carbon atoms, an alicyclic hydrocarbon group having 3 to 24 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms; A represents 3 to 8 carbon atoms. An alkylene group, E is an ethylene group, AO and EO may be a random bond or a block bond; m is 0 or an integer of 1 to 400, n is an integer of 0 or 1 to 400, and m + n is 1 to 400 .)
And it is a manufacturing method of the monohydric alcohol alkylene oxide adduct (A) which adds an alkylene oxide on the conditions with which a reaction system satisfy | fills the following relational expression (3).
Relational expression 20,000 ≧ [1.5 × P + 0.06 × S × X / W + 0.017 × C
+ 0.056 × D] × M (3)
[In the formula, P is a peroxide value (meq / kg) in a monohydric alcohol, S is a space capacity after charging the monohydric alcohol in a reaction vessel (liter: L), and X is a reaction system under normal temperature and normal pressure. O concentration (ppm), W is the amount of monohydric alcohol charged (g), C is the aldehyde content of monohydric alcohol (ppm), D is the water content in the reaction system (ppm), and M is the molecular weight of monohydric alcohol]

  The monohydric alcohol alkylene oxide adduct of the present invention is a high-purity monohydric alcohol alkylene oxide adduct having a low molecular weight diol component.

The monohydric alcohol alkylene oxide adduct (A) of the present invention satisfies the above relational expression (1). It preferably satisfies the relational expression (1 ′), and more preferably satisfies the relational expression (1 ″). If the relational expression (1) is not satisfied, many by-products other than the target product exist and the purity of the above (A) is lowered.
Relational expression
1.15 ≧ A / (H × ΔM) (1 ′)
Relational expression
1.12 ≧ A / (H × ΔM) (1 ″)

  In the general formula (2), R represents an aliphatic hydrocarbon group having 1 to 24 carbon atoms, an alicyclic hydrocarbon group having 3 to 24 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms. The aliphatic hydrocarbon group having 1 to 24 carbon atoms may be linear or branched. Specifically, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, lauryl, tridecyl, Examples include alkyl groups such as tetradecyl, pentadecyl, hexadecyl, octadecyl, nonadecyl, 2-ethylhexyl, and 2-ethyloctyl group; alkenyl groups such as octenyl, decenyl, dodecenyl, tridecenyl, pentadecenyl, oleyl, and gadryl groups. Examples of the alicyclic hydrocarbon group having 3 to 24 carbon atoms include ethylcyclohexyl, propylcyclohexyl, octylcyclohexyl group and the like. Examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms include phenol and alkylphenols having 1 to 18 carbon atoms (nonylphenol and the like). Among these, an aliphatic hydrocarbon group having 1 to 12 carbon atoms is preferable, and an aliphatic hydrocarbon group having 1 to 8 carbon atoms is more preferable.

  A is an alkylene group having 3 to 8 carbon atoms, specifically, 1,2-propylene group, 1,2-butylene group, 1,4-butylene group, 1-phenyl-1,2-ethylene group. Yes, preferably 1,2-propylene group. E is an ethylene group. AO and EO may be random bonds or block bonds. Random bond is preferable.

m is 0 or an integer of 1 to 400, preferably 1 to 300, and more preferably 1 to 200. When m exceeds 400, the viscosity becomes high and handling becomes difficult. n is 0 or an integer of 1 to 400, preferably 5 to 300, and more preferably 10 to 200. When n exceeds 400, the viscosity becomes high and handling becomes difficult.
m + n is 1 to 400, preferably 10 to 420, and more preferably 20 to 200. When m + n exceeds 400, the viscosity becomes high and handling becomes difficult.
The number average molecular weight is preferably 76 to 24,000, more preferably 252 to 18,000.

  The ratio n / (m + n) of n and m is preferably 0.95 or less, more preferably 0.90 or less. When n / (m + n) is 0.95 or less, it is easy to handle the alcohol alkylene oxide adduct at a low temperature.

A monohydric alcohol alkylene oxide adduct is produced by subjecting a monohydric alcohol to an alkylene oxide addition reaction in the presence of an alkali catalyst.
The monohydric alcohol can be expressed as ROH, and R is the same as R in the general formula (2). The preferred ones are the same.

The reaction is preferably performed while satisfying the relational expression (3).
The right side of the relational expression (3) represents the molar concentration of water molecules generated in the reaction system. The left side of the relational expression is 20,000, preferably 15,000, and more preferably 13,000 or less. When the left side of the relational expression (3) is 20,000 or less, it is difficult to generate water in the reaction system, and a high molecular weight component different from the target product is hardly generated as a by-product.

(Peroxide value measurement method)
The peroxide value is expressed in milliequivalents per gram of iodine that is liberated when potassium iodide is allowed to act on the sample. Peroxide value is obtained by dissolving a sample in a mixed solution of chloroform and glacial acetic acid, reacting with potassium iodide, and using a starch indicator, the iodine produced by reacting with the peroxide is an aqueous sodium thiosulfate solution with a known normality. It is analyzed by a titration method, and is calculated from the titration amount of sodium thiosulfate and converted to milliequivalents of iodine.

(Measurement method of aldehyde content)
Weigh sample accurately in a glass bottle with a lid. The sampling amount is 50 g when the expected aldehyde content is less than 100 ppm, 30 g when it is 100 or more and less than 300 ppm, and 20 g or less when it is 300 ppm or more. When the aldehyde content is unknown, measurement is first performed with a sampling amount of 20 g, and when the measured value is less than 300 ppm, the measurement is performed again with the above sample amount. After sampling, 50 ml (25 ° C.) of hydroxylamine hydrochloride solution (50 g of hydroxylamine hydrochloride dissolved in 150 ml of pure water and added with isopropanol to 1 L) was added with a whole pipette, mixed well, sealed, and sealed. Leave at ℃ 30 minutes. After cooling to room temperature, 50 mL of methanol is added immediately before titration, and potentiometric titration is performed with an N / 10 methanolic KOH standard solution. At the same time, a blank test is performed.
Aldehyde content (ppm) = (KB) × Y × 2900 / Z
K: Titration ml number of N / 10 methanolic KOH standard solution required for this test B: Titration ml number of N / 10 methanolic KOH standard solution required for blank test Y: Force of N / 10 methanolic KOH standard solution Value Z: Sampling amount (g)

Examples of the alkylene oxide having 3 to 8 carbon atoms include 1,2-propylene oxide (PO), 1,2- or 2,3-butylene oxide, tetrahydrofuran, styrene oxide and the like. Of these, PO is preferred. The addition form of PO and C2 alkylene oxide (ethylene oxide; EO) may be block or random. Random addition is preferable.
The number of added moles of alkylene oxide or EO having 3 to 8 carbon atoms is the same as m and n in the general formula (1). The preferred ones are the same.
Examples of the alkali catalyst include sodium hydroxide, potassium hydroxide, metallic sodium, metallic potassium, alkoxides of these compounds ROH, and solutions of these compounds ROH. In addition to the alkali catalyst described above, Lewis acid catalysts such as boron trifluoride and tin tetrachloride are usually used for the production of the alkylene oxide adduct, but cyclic monomers such as 1,4-dioxane using an acid catalyst are used. In addition, the cyclic polyether is produced as a by-product, and it is difficult to obtain a compound with the desired purity, which is not preferable.

  After drying the reaction system, adding an alkali catalyst and dehydrating the system, the alkylene oxide can be continuously reacted preferably at 80 to 200 ° C, more preferably at 100 to 180 ° C.

A monohydric alcohol alkylene oxide adduct having a molecular weight 10 times or more that of the above monohydric alcohol is usually produced by taking out the monohydric alcohol alkylene oxide adduct once subjected to the alkylene oxide addition reaction and adding the alkylene oxide again. be able to. In a normal monohydric alcohol alkylene oxide addition reaction, the minimum stirring capacity of the reaction vessel is limited, so the amount of monohydric alcohol charged is limited, and the amount of alkylene oxide that can be added in one reaction. Is limited. Therefore, as the raw alcohol, the monohydric alcohol alkylene oxide adduct (A) of the present invention may be used as the raw alcohol in addition to the above-mentioned alcohol. That is, the monohydric alcohol alkylene oxide adduct may be a one-step reaction or a two-step or more multi-step reaction. It is preferable to carry out the addition reaction of alkylene oxide under the condition that the sum of the values on the right side of the relational expression (3) in each stage is 20,000 or less.
Since the monohydric alcohol alkylene oxide adduct of the present invention is highly pure and has a low content of a high molecular weight diol component, when subjected to a reaction, side reactions such as a crosslinking reaction can be suppressed. It can be used as a reactive monomer by modifying a hydroxyl group to a reactive substituent.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. Below, a part shows a weight part.

The molecular weight measurement conditions by gel permeation chromatograph (hereinafter abbreviated as GPC) are as follows.
<< GPC measurement conditions >>
Model: HLC-8120 (manufactured by Tosoh Corporation)
Column TSK gel SuperH4000
TSK gel SuperH3000
TSK gel SuperH2000
(Both manufactured by Tosoh Corporation)
Column temperature: 40 ° C
Detector: RI
Solvent: Tetrahydrofuran Flow rate: 0.6 ml / min Sample concentration: 0.25%
Injection volume: 10 μl
Standard: Polyoxyethylene glycol
(Tosoh Corporation; TSK STANDARD
POLYETHYLENE OXIDE)
Data processor: SC-8020 (manufactured by Tosoh Corporation)

Example 1
In a 2 liter stainless steel autoclave with a stirring and temperature control function that was previously dried in a thermostatic bath at 150 ° C. for 8 hours, 162 parts of diethylene glycol monobutyl ether (trade name: butyl diglycol, manufactured by Nippon Emulsifier Co., Ltd.), 45% hydroxylation 4.0 parts of an aqueous potassium solution was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 50 ppm. Thereafter, dehydration was performed at 100 ° C. for 2 hours under reduced pressure (1 to 5 mmHg). The water content at this time was 200 ppm, the peroxide value of the used diethylene glycol monobutyl ether was 20 meq / kg, and the aldehyde content was 840 ppm. Next, 1496 parts of ethylene oxide (hereinafter abbreviated as EO) and 290 parts of propylene oxide (hereinafter abbreviated as PO) were introduced so as to be randomly added so that the gauge pressure was 1 to 3 kgf / cm ^2, and a monohydric alcohol alkylene oxide adduct was introduced. (A-1) was obtained. The right side of the relational expression (3) obtained from the reaction conditions was 8993. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-1) was 1.114.

Example 2
In a 2 liter stainless steel autoclave with stirring and temperature control function, which was previously dried in a thermostat at 150 ° C. for 8 hours, 202 parts of diethylene glycol monohexyl ether (trade name: HEDG, manufactured by Nippon Emulsifier Co., Ltd.), 45% potassium hydroxide 4.0 parts of an aqueous solution was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 60 ppm. Thereafter, dehydration was performed at 100 ° C. for 2 hours under reduced pressure (1 to 5 mmHg). The water content at this time was 160 ppm, the peroxide value of the used diethylene glycol monohexyl ether was 24 meq / kg, and the aldehyde content was 200 ppm. Next, 1508 parts of PO were introduced so that the gauge pressure was 1 to 3 kgf / cm ² to obtain a monohydric alcohol alkylene oxide adduct (A-2). The right side of the relational expression (3) obtained from the reaction conditions was 9775. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-2) was 1.115.

Example 3
In a 2 liter stainless steel autoclave with a stirring and temperature control function that was previously dried in a thermostat at 150 ° C. for 8 hours, 120 parts of diethylene glycol monomethyl ether (trade name: methyl diglycol, manufactured by Nippon Emulsifier Co., Ltd.), 45% hydroxylation 4.0 parts of an aqueous potassium solution was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 60 ppm. Thereafter, dehydration was performed at 100 ° C. for 2 hours under reduced pressure (1 to 5 mmHg). The water content at this time was 160 ppm, the peroxide value of the used diethylene glycol monomethyl ether was 5 meq / kg, and the aldehyde content was 60 ppm. Subsequently, 660 parts of EO was introduced so that the gauge pressure was 1 to 3 kgf / cm ² to obtain an alkylene oxide adduct (A-3) of a monohydric alcohol. The right side of the relational expression (3) obtained from the reaction conditions was 2104. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-3) was 1.099.

Example 4
Into a 2 liter stainless steel autoclave with stirring and temperature control function, which was dried in a constant temperature bath at 150 ° C. for 8 hours in advance, 78 parts of (A-3) and 4.0 parts of 45% aqueous potassium hydroxide solution were added and mixed. The system was replaced with nitrogen. The oxygen concentration at this time was 30 ppm. Thereafter, dehydration was performed at 100 ° C. for 2 hours under reduced pressure (1 to 5 mmHg). The water content at this time was 120 ppm, the peroxide value of (A-3) used was 2 meq / kg, and the aldehyde content was 30 ppm. Subsequently, 880 parts of EO and 580 parts of PO were introduced so as to be randomly added so that the gauge pressure was 1 to 3 kgf / cm ² , thereby obtaining an alkylene oxide adduct (A-4) of a monohydric alcohol. The right side of the relational expression (3) obtained from the reaction conditions was 7996, and the sum of the right side of the relational expression (3) obtained from the reaction conditions of (A-3) was 10100. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-4) was 1.117.

Comparative Example 1
Stirrer, rectifying tube, thermometer, cooling tube, nitrogen gas blowing tube fitted with calcium chloride drying tube, distillation thermometer, 2 liter four-necked flask, A distillation apparatus was assembled using a bifurcated tube and two eggplant-shaped flasks having a capacity of 1 liter. 1000 parts of diethylene glycol monomethyl ether (trade name: methyl diglycol, manufactured by Nippon Emulsifier Co., Ltd.) was placed in a four-necked flask of the assembled distillation apparatus. Next, 10 parts of metallic sodium was added and stirred under a nitrogen gas atmosphere until the metallic sodium was completely dissolved. While gradually flowing nitrogen gas, the temperature was gradually raised, and distillation was performed under a vacuum of 5 mmHg or less. After taking the first distillation, 500 copies of the main distillation were collected. The water content of dehydrated distilled diethylene glycol monomethyl ether obtained as the main distillate was 0.5 ppm. To 480 parts of the resulting dehydrated distilled diethylene glycol monomethyl ether, 46 parts of metallic sodium was added under a nitrogen gas atmosphere and stirred until completely dissolved, and a slight turbid substance precipitated was pressure filtered under a nitrogen gas atmosphere, A high purity sodium methoxide solution in diethylene glycol monomethyl ether (A′-5) was prepared.
Take 3 liters of dehydrated toluene (reagent: moisture 2.8 ppm) in a stainless steel autoclave with stirring and temperature control function, raise the temperature to 90 ° C and stir for 30 minutes, then blow line and preparation line attached to the autoclave Was thoroughly washed, and the whole amount was discharged under nitrogen gas pressure. Each line was sufficiently purged with nitrogen gas until toluene mist disappeared, and the reaction system was dried at 120 ° C. for 5 hours under a vacuum of 5 mmHg or less. Into a 2 liter autoclave, 1.6 liters of dehydrated toluene (moisture 3.9 ppm) was injected under nitrogen gas pressure, stirred for 30 minutes, and then the whole amount was put into a pressure vessel that had been dried in a constant temperature bath at 150 ° C for 3 hours in advance. Extracted. It was confirmed that the water content of the extracted toluene was 4.0 ppm and the calculated water value of the reaction system was 0.1 ppm. After each line was sufficiently purged with nitrogen gas until toluene mist disappeared, the reaction system was dried at 120 ° C. for 5 hours under a vacuum of 5 mmHg or less.
Nitrogen was substituted in the mixing system of a 2 liter stainless steel autoclave with a stirring and temperature control function that had been dried in a thermostatic bath at 150 ° C. for 8 hours in advance, and 123 parts of (A′-5) was charged with a syringe. The oxygen concentration at this time was 80 ppm. The peroxide value of (A′-5) used was 92 meq / kg, and the aldehyde content was 1600 ppm. Next, 1760 parts of EO was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and an alkylene oxide adduct (A-5) of a monohydric alcohol was obtained. The right side of the relational expression (3) obtained from the reaction conditions was 20356. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-5) was 1.188.

Comparative Example 2
In a stainless steel autoclave with stirring and temperature control function, which was previously dried in a thermostat at 150 ° C. for 8 hours, 162 parts of diethylene glycol monobutyl ether (trade name: butyl diglycol, manufactured by Nippon Emulsifier Co., Ltd.), 45% aqueous potassium hydroxide solution 4 0.0 part was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 60 ppm. Thereafter, dehydration was performed at 100 ° C. for 2 hours under reduced pressure (1 to 5 mmHg). The water content at this time was 220 ppm, the peroxide value of the used diethylene glycol monobutyl ether was 65 meq / kg, and the aldehyde content was 1000 ppm. Next, 1496 parts of EO and 290 parts of PO were introduced so as to be randomly added so that the gauge pressure was 1 to 3 kgf / cm ² , thereby obtaining an alkylene oxide adduct (A-6) of alcohol. The right side of the relational expression (3) obtained from the reaction conditions was 20551. The right side of the relational expression (1) obtained from the molecular weight measurement chart by the GPC method of (A-6) was 1.190.

  Table 1 summarizes the above values. As is apparent from this table, the alcohol alkylene oxides of Comparative Examples 1 and 2 have a high content of by-product diol. In contrast, the monohydric alcohol alkylene oxide adducts of Examples 1 to 4 have high purity.

Test example <Glycidyl etherification>
In a reaction vessel equipped with a stirrer, temperature control measures, and a wet pulverizer (attached to the outside of the reaction vessel), the above (A-1) and epichlorohydrin in a molar ratio of 1: 2 in total, 500 parts, 500 parts of toluene In a nitrogen atmosphere, granular sodium hydroxide is intermittently added dropwise at a temperature of 19 to 29 ° C. over a period of 9.5 hours. During this time, the sodium hydroxide in the reaction vessel is pulverized using a wet pulverizer. Thereafter, reaction aging was carried out at 25 to 29 ° C. for 5 hours, and (A-1) was glycidyl etherified to obtain (B-1).
The same operation was performed for (A-2) to (A-6), and glycidyl etherification was performed to synthesize (B-2) to (B-6).

<Polymerization test>
A flask equipped with a thermometer, nitrogen inlet tube, stirrer, water separator and reflux condenser was charged with 100 parts (0.51 mol) of dimethyl terephthalate, 62 parts (1 mol) of ethylene glycol, and 0.06 calcium acetate monohydrate. The mixture was heated with stirring under a nitrogen stream, the reaction temperature was raised to 220 ° C., and the ester exchange reaction was carried out for 4 hours while distilling off methanol. Thereafter, 0.1 part of trimethyl phosphate, 0.05 part of antimony trioxide and 50 parts of (B-1) were added, and polymerization was performed at 280 ° C. under reduced pressure of 1 mmHg or less for 3 hours. Was observed.
The same operation was performed for (B-2) to (B-6).

  Table 2 lists the results of the polymerization test. As is apparent from this table, gelation occurs when the reaction is carried out using (B-1) to (B-4) which are glycidyl ethers synthesized using (A-1) to (A-4) of the present invention. Has not caused. On the other hand, when the reaction is performed using (B-5) to (B-6) which are glycidyl luters synthesized using the comparative examples (A-5) to (A-5), there are many diol components. Therefore, gelation occurs during the polymerization.

The alcohol alkylene oxide adduct of the present invention has high purity and is useful as a reactive monomer by modifying the terminal hydroxyl group to a reactive substituent. It can be used as a reaction raw material such as polyester and epoxy resin.

Claims (4)

In the chromatogram obtained by GPC, the straight line connecting the elution start point to the elution end point is L, the height from the top of the maximum peak from L is H, the half-value width is ΔM, and the total peak area is A. A monohydric alcohol alkylene oxide adduct (A) represented by the general formula (2) characterized by satisfying the following relational expression (1).
Relational expression
1.18 ≧ A / (H × ΔM) (1)
General formula
RO- (AO) m / (EO) n-H (2)
(In the formula, R represents an aliphatic hydrocarbon group having 1 to 24 carbon atoms, an alicyclic hydrocarbon group having 3 to 24 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms; A represents 3 to 8 carbon atoms. An alkylene group, E is an ethylene group, AO and EO may be a random bond or a block bond; m is 0 or an integer of 1 to 400, n is an integer of 0 or 1 to 400, and m + n is 1 to 400 .) n / (m + n) is 0.95 or less, The monohydric alcohol alkylene oxide adduct (A) of Claim 1 characterized by the above-mentioned. The monovalent alcohol according to claim 1 or 2, wherein in the method for producing a monohydric alcohol alkylene oxide adduct (A) by adding an alkylene oxide to a monohydric alcohol, the addition is performed under a condition satisfying the following relational expression (3). A method for producing an alcohol alkylene oxide adduct (A).
Relational expression 20,000 ≧ [1.5 × P + 0.06 × S × X / W + 0.017 × C
+ 0.056 × D] × M (3)
[In the formula, P is a peroxide value (meq / kg) in a monohydric alcohol, S is a space capacity after charging the monohydric alcohol in a reaction vessel (liter: L), and X is a reaction system under normal temperature and normal pressure. O concentration (ppm), W is the amount of monohydric alcohol charged (g), C is the aldehyde content of monohydric alcohol (ppm), D is the water content in the reaction system (ppm), and M is the molecular weight of monohydric alcohol] In the production method of adding an alkylene oxide in multiple steps, an alkylene oxide is added to a monohydric alcohol to produce a monohydric alcohol alkylene oxide adduct (A), and the alkylene oxide is further added to the (A) after being taken out. The method for producing a monohydric alcohol alkylene oxide adduct (A) according to claim 3, wherein the sum of the values on the right side of the relational expression (3) at each stage is 20,000 or less.