JPH05214159A - Mixed alcohol for plasticizer and plasticizer produced therefrom - Google Patents

Abstract

PURPOSE:To provide a plasticizer exhibiting excellent low-volatility, oil- resistance and water-resistance when compounded to a resin and to provide a mixed IOC alcohol for plasticizer for getting the above plasticizer performance. CONSTITUTION:The objective mixed alcohol is composed of 95-98.5wt.% of 2-propyl-1-heptanol, 1.5-5wt.% of 2-methyl-2-ethyl-1-heptanol and <=0.5wt.% of 4-methyl-2-propyl-1-hexanol. A carboxylate plasticizer is produced by using the alcohol.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a mixed alcohol for a plasticizer having 10 carbon atoms and a plasticizer obtained by esterifying a mixed alcohol for a plasticizer with a carboxylic acid or a carboxylic acid anhydride. The plasticizer represented by phthalic acid diester and adipic acid diester is mainly used as a plasticizer for vinyl chloride resin.

[0002]

BACKGROUND ART Conventionally, decanol, which is an alcohol having 10 carbon atoms, is subjected to hydroformylation reaction of a C 4 fraction (hereinafter referred to as a BB fraction) obtained by thermal decomposition or catalytic cracking of hydrocarbon oil to give valeraldehyde. It is manufactured by producing a decane compound, then subjecting this to an aldol condensation reaction to produce a decenal compound, and further subjecting this to a hydrogenation reaction. Butene in the BB fraction is 1-butene, 2
-There are three types, butene and isobutene. Therefore, the valeraldehyde obtained by hydroformylating this is n-
Valeraldehyde, 2-methylbutyraldehyde, 3-
It is a mixture of methyl butyraldehyde and pivalaldehyde.

Therefore, the condensation product of valeraldehydes and the decanol product obtained by the hydroformylation reaction of the BB fraction are generally a mixture of various structural isomers. Regarding the oxo reaction of butenes, von Bernhard et al., Chemiker-Z
eitung) 99 Yehrgang (Jahrgan)
g) (1975), Nr. 11, P452-458, JP-A-55-127335 and the like, valeraldehyde can be produced under ordinary hydroformylation conditions, and
The hydroformylation conditions and the like for obtaining n-valeraldehyde in higher yield are described.

Further, EP Patent No. 213639, Japanese Patent Publication No. 61-501268, US Pat. No. 4,668,651,
JP-B-58-57413 discloses a suitable polyphosphite for producing various C5 aldehydes by hydroformylating butenes by using polyphosphite or triphenylphosphine as a ligand in the presence of a rhodium complex catalyst. And the hydroformylation conditions are described.

Further, in JP-A-58-206537, n-valeraldehyde and 2-substituted aldehyde in an alcohol containing 2-propylheptanol as a main component for producing decanol having good plasticizer performance from butenes. The composition of valeraldehyde and the condensation conditions are described so that the amount of alcohol derived from the product of the cross aldol condensation reaction with is less than 20% by weight of the product.

US Pat. Nos. 2,912,089 and 312
No. 1051 describes 2-propylheptanol derived from the condensation product of n-valeraldehyde and decanol derived from the product of the cross aldol condensation reaction of n-valeraldehyde with 2-methylbutyraldehyde. Therefore, the condensation and hydrogenation may be carried out by ordinary methods. 2-Propylheptanol means di-2-propylheptyl phthalate or di-2-adipate.
It shows excellent performance when converted to propylheptyl, and when decanol derived from the product of the cross aldol condensation reaction is used as a plasticizer, the plasticizer performance is 2-propylheptanol. Although it is inferior to the case of performing it, it is described that the performance is not so inferior when it is used as a mixture with up to 10% by weight with 2-propylheptanol.

Further, in JP-A-2-196741 and JP-A-2-209838, butenes are oxo-modified to give n-
Valeraldehyde, 2-methylbutyraldehyde, 3-
Conditions for producing a mixture of four aldehydes of methyl butyraldehyde and pivalaldehyde, and producing an alcohol mixture having a carbon number of 10 for a plasticizer through an aldol condensation reaction without isolation of the mixture and a subsequent hydrogenation reaction, It is described that when this mixed alcohol is converted into phthalic acid diester or adipic acid diester, the physical properties as a plasticizer are improved as compared with di-2-propylheptyl phthalate or di-2-propylheptyl adipate. Also, in “Plasticizer—Theory and Application”, edited by Koichi Murai, published by Koshobo (1973), when the carbon branching degree of the alcohol portion in the plasticizer molecule is large, electrical insulation, oil resistance, migration resistance and resistance to resistance are high. It is described that the stain resistance is improved, but the cold resistance, plasticizing efficiency, thermal stability, weather resistance and volatility resistance are decreased.

[0008]

In the hydroformylation of a C4 olefin (isomer of butene) mixture, the composition of the product valeraldehyde mixture can be controlled to some extent by appropriately selecting the reaction conditions, the catalyst and the like. It is known that When the resulting valeraldehyde mixture, that is, a mixture containing n-valeraldehyde, 2-methylbutyraldehyde, 3-methylbutyraldehyde and pivalaldehyde is used in the aldol condensation reaction, decanol produced by the subsequent hydrogenation reaction is isomerized. It becomes a body mixture. It is well known that when the decanol mixture is converted into a plasticizer for a vinyl chloride resin composition, the composition of the decanol mixture affects various physical properties of the resin composition.

However, in the above-mentioned prior art,
Although it is described that a decanol composition within a certain range may be used, it has not been found that a decanol composition with a certain composition gives the best physical properties as a vinyl chloride resin composition. Therefore, in the case of using the above decanol, it has been desired to elucidate the raw material decanol composition for obtaining a resin composition that gives excellent plasticizer performance. As a result of intensive research and development for solving the above problems, the present inventors have unexpectedly found the following facts.

That is, 2-propyl-1-heptanol (hereinafter referred to as 2PHO) is 95 to 98.5% by weight, and 4-methyl-2-propyl-1-hexanol (hereinafter referred to as MPHO) is 1.5 to 9% by weight. 5% by weight and 2-methyl-2-ethyl-1-heptanol (hereinafter referred to as MEHO
A mixed decanol containing 0.5% by weight or less of phthalic acid or an anhydride of phthalic acid is converted into phthalic acid diester, and the obtained phthalic acid diester is used as a plasticizer. When the vinyl chloride resin composition was subjected to a normal physical property evaluation test, it was found to be a 2PHO high purity product (99.7% by weight) in terms of cold resistance (low temperature flexibility), oil resistance and volatility resistance (heat aging resistance).
It has been found that it exhibits better physical properties than the vinyl chloride resin composition in which phthalic acid diester is used as a plasticizer. As is apparent from the above description, the object of the present invention is to provide a mixed alcohol for a plasticizer having 10 carbon atoms, which provides excellent plasticizer performance in volatility resistance, oil resistance and water resistance, and the above-mentioned mixed alcohol. To provide a plasticizer having excellent performance.

[0011]

The present invention has the following constitutional requirements. (1) In producing a plasticizer by esterifying an alcohol having 10 carbon atoms with a carboxylic acid or a carboxylic acid anhydride, 2PHO is 95 to 98.5 wt% as a composition of the alcohol to be subjected to the esterification reaction. %, MPHO is 1.5 to 5% by weight, and MEHO is 0.5
A mixed alcohol for a plasticizer characterized by being less than or equal to wt% (however, 2PHO is 2-propyl-1-heptanol, MPHO is 4-methyl-2-propyl-1-hexanol, and MEHO is 2-methyl-2. -Ethyl-1-heptanol, respectively). (2) A plasticizer obtained by subjecting the mixed alcohol for plasticizer according to the above 1 to esterification reaction with a carboxylic acid or a carboxylic acid anhydride. (3) carboxylic acid or carboxylic acid anhydride is phthalic acid,
The plasticizer according to the above item 2, which is phthalic anhydride, adipic acid, azelaic acid, sebacic acid, trimellitic acid, trimellitic anhydride, pyromellitic acid or pyromellitic anhydride.

The mixed alcohol for plasticizers of the present invention is not limited as long as its composition contains 95 to 98.5% by weight of 2PHO, 1.5 to 5% by weight of MPHO, and 0.5% by weight or less of MEHO. It does not choose the manufacturing method. That is, 1-
Butene, 2-butene, or a mixture of 1-butene and 2-butene is oxo-oxidized to obtain an aldehyde product having 5 carbon atoms, and the aldehyde product is subjected to an aldol condensation reaction under ordinary aldol condensation reaction conditions to obtain 10 carbon atoms. Alkenal product was obtained, followed by 2PH under normal hydrogenation reaction conditions.
A method of obtaining an alcohol mixture of O, MPHO, and MEHO may be used, and a method of obtaining the composition by distillation or 2PH
The method of separately preparing O, MPHO or MEHO and mixing them so as to give the composition of the alcohol mixture does not cause any disadvantage.

The oxidization method of the present invention comprises hydroformylating Spentspent BB fraction or 1-butene by using polyphosphite or triphenylphosphine as a ligand in the presence of a rhodium complex catalyst to form C5 aldehyde. To manufacture. The spent spent fraction is obtained by removing butadiene and isobutene from a BB fraction mainly containing butenes. Reaction pressure is atmospheric pressure to 300 kg / cm ² , reaction temperature is 50 to 150 ° C., H ₂ / C
The molar ratio of O is 0.5 to 10, the catalyst concentration is several ppm to several weight%, and the molar ratio of the ligand to the catalyst is usually 1 to 1000. The reaction may be either continuous type or batch type. Then, an aldehyde having 5 carbon atoms is obtained by distillation.

The aldol condensation reaction uses a conventional catalyst,
The reaction temperature is about 20 ° C to about 150 ° C, preferably 60 ° C to
It is performed under stirring conditions of 100 ° C. The reaction pressure may be carried out under a wide range of pressures from vacuum to pressure, preferably performed at ^{0.9kg / cm 2 A~1.5kg / cm 2} A. The reaction may be carried out at reflux. The catalyst may be a strong alkali catalyst such as sodium hydroxide, potassium hydroxide, sodium cyanide or potassium cyanide, or a weak alkali catalyst such as trimethylamine, dimethylamine or triethylamine. The concentration of the alkaline aqueous solution is in the range of about 1 to 20% by weight, and the amount of the alkaline aqueous solution is
It is carried out at 0.1 to 10 times, preferably 0.5 to 3 times. The reaction time can be finished at the time to obtain the desired conversion rate,
It is about several minutes to about 5 hours. The reaction may be either continuous or batch.

After completion of the reaction, oil / water is separated and the oil layer is directly or distilled to obtain alkenal having 10 carbon atoms. Then, a hydrogenation reaction is carried out using a usual hydrogenation catalyst such as Ni, Cu, Cr, Pd. Reaction pressure is normal pressure to 300 kg / cm
² G, preferably 20 to 150 kg / cm ² G, temperature is 3
It is carried out under conditions of 0 to 300 ° C, preferably 100 to 200 ° C. Hydrogenation leads to the reduction of unsaturated carbon bonds and aldehydes. The hydrogenation reaction may be either a suspension system using a powder catalyst or a fixed bed system using a molded catalyst, and may be a continuous system or a batch system. The reaction product is purified by ordinary distillation to obtain a target composition having 10 carbon atoms.
To obtain mixed alcohol.

In the case of the method for producing an aldehyde mixture as described above, the following four kinds of decanol are theoretically produced. That is, 2 as a product derived from the reaction between n-valeraldehyde (hereinafter referred to as nVLA) and nVLA.
As a product derived from the reaction of PHO, nVLA and 2-methylbutyraldehyde (hereinafter referred to as 2MBA), MPHO and MEHO, as a product derived from the reaction of 2MBA and 2MBA, 2,4-dimethyl-2-ethyl. It is -1-hexanol.

The mixed alcohol obtained as described above is then subjected to an esterification reaction with phthalic anhydride, adipic acid or the like in the presence of a titanium catalyst or an acidic catalyst such as P-toluenesulfonic acid by a conventional method, and a phthalic acid diester, Plasticizers such as adipic acid diesters, and corresponding plasticizers by esterification reaction with aromatic carboxylic acids such as trimellitic anhydride and pyromellitic anhydride, and aliphatic dibasic acids such as azelaic acid and sebacic acid. And

The vinyl chloride resin in the present invention is polyvinyl chloride and vinyl chloride copolymer, and the vinyl chloride copolymer mainly comprises vinyl chloride and other monomers such as ethylene, propylene, vinyl acetate, alkyl vinyl ether, and acrylic. Examples thereof include copolymers with acid esters, methacrylic acid esters and the like, but the present invention is not limited to the above resin types.

[0019]

EXAMPLES The present invention will be described in detail below based on examples. Moreover, the physical property values in the following examples were based on the following test methods. [Specific gravity] According to ASTM D792. [Tensile Test] Tensile strength, elongation and 100% modulus were measured according to JIS K 6723. [Heating weight change rate] A tensile test piece of JIS K 6723 is heated in an oven at a temperature of 100 ° C for 120 hours,
The weight change rate is measured. The weight change rate was calculated by the following formula. Weight change rate = (W ₂ −W ₁ ) / W ₁ × 100 Here, W ₁ represents the weight (g) of the test piece before the test, and W ₂ represents the weight (g) of the test piece after the test [ Flexible temperature] According to JIS K 6745. [Volume Specific Resistance] The temperature of the constant temperature bath was measured at 30 ° C. according to JIS K 6723.

[Oil resistance test weight change rate] JIS K 6
The tensile test piece of 723 was a Class 1 No. 2 insulating oil (J
Immerse in ISC 2320) for 4 hours and measure the rate of weight change. The weight change rate was calculated by the following formula. Weight change rate = (W ₂ −W ₁ ) / W ₁ × 100 Here, W ₁ represents the weight (g) of the test piece before the test, and W ₂ represents the weight (g) of the test piece after the test [ Water Resistance Test Weight Change Rate] A JIS K 7113 No. 2 test piece is immersed in warm water of 100 ° C. for 48 hours to measure the weight change rate. The weight change rate was calculated by the following formula. Weight change rate = (W ₂ −W ₁ ) / W ₁ × 100 Here, W ₁ represents the weight (g) of the test piece before the test, and W ₂ represents the weight (g) of the test piece after the test. [Hardness] According to JIS K 6301, a spring type hardness tester A type was used.

The composition analysis of the alcohol having 10 carbon atoms in the present invention was carried out by capillary gas chromatography analysis.
The gas chromatography analysis conditions are shown below. Analyzer: GC-14A (manufactured by Shimadzu Corporation) Column name: Capillary G-100 (manufactured by Chemicals Inspection Association) Column details: Length 40 m, inner diameter 1.2 mm, film thickness 1 μm Detector: FID Column temperature: 120 ° C Note Inlet temperature: 200 ° C. Detector temperature: 200 ° C. Carrier: Nitrogen 20 ml / min Calculation method: Internal standard method Sample for internal standard: 4-heptanone (manufactured by Chisso Corporation: C
S-7)

Dioctyl phthalate (DOP) used in the following comparative examples was a product manufactured by Chisso Corporation, and diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP) were products manufactured by Sekisui Chemical Co., Ltd.

Example 1 98.3% by weight as 2PHO and 1.6 as MPHO
%, And a mixed alcohol containing 0.002% by weight as MEHO was produced by the following method. (1) Hydroformylation An amount of rhodium dicarbonylacetylacetonate liberated into a precursor solution to give about 250 ppm of rhodium and a bisphosphite ligand represented by the following (formula 1) (about 8 per 1 mol equivalent of rhodium). 20 mol of a catalyst precursor solution containing 0.5 molar equivalent of about 2% by weight in the precursor solution) and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate as a solvent was replaced with nitrogen. The glass reactor was inserted into the glass reactor and the hydroformylation reaction was carried out under the following conditions.

[Chemical 1] The total gas pressure is about 11 kg / cm ² G, the partial pressures of hydrogen, carbon monoxide and 1-butene are 4.4 kg / cm ² A, respectively.
2.1 Kg / cm ² A and 0.21 Kg / cm ² A, the rest was carried out in nitrogen and aldehyde. The flow rates of the feed gases (carbon monoxide, hydrogen, 1-butene, nitrogen) were individually adjusted with a flow meter, and the reaction temperature was 71 ° C. Generated C
As a result of analyzing 5 aldehydes by capillary gas chromatography, n-valeraldehyde (hereinafter, n
VLA and 2-methylbutyraldehyde (hereinafter,
2MBA) was 35.2: 1.

(2) Aldol condensation In a 2 liter four-necked flask equipped with a magnetic stirrer, Dimroth condenser, thermocouple thermometer and dropping device (1)
C5 aldehyde solution (nVLA 97.
2 wt%, 2.8 wt% as 2MBA) 351.2 g
Was charged and stirred. 1.25 wt% NaOH aqueous solution 35
5.5g was prepared and this was dripped at 25 degreeC in the flask. The dropping was completed after 59 minutes, and the temperature in the system at this time was 6
It was 0 ° C. After that, heating was started, and stirring was continued for 4 hours after reaching 85 ° C. Next, after cooling to room temperature, stirring was stopped, oil-water separation was carried out, and 292.1 g (water content 0.5
An oil layer of 7% by weight) was obtained.

(3) Hydrogenation reaction In a 3 liter stainless steel autoclave equipped with a magnetic stirrer, hydrogen pressure regulator and thermocouple thermometer, under nitrogen atmosphere, 1602.5 g of oil layer of aldol condensation liquid prepared in the same manner as in (2). And Raney nickel 80.
4g was charged. After the system was replaced with hydrogen three times, the hydrogen pressure was set to 50 Kg / cm ² G and the mixture was stirred at 500 rpm. At the same time, when the electric furnace was heated to raise the temperature, hydrogen absorption started at an internal temperature of about 95 ° C. and continued for 3.5 hours thereafter (the maximum temperature reached during that time was 165 ° C.). ). After the hydrogen absorption was stopped, the stirring was continued at 130 to 148 ° C. for another 2 hours, and then the heating was stopped. After standing overnight, the catalyst was filtered off with a membrane filter to obtain an oil layer of 1617.3 g.
This oil layer was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. At the beginning of distillation, the operation was performed at a reduced pressure of 30 to 60 mmHg, then the reduced pressure was changed from 10 to 30 mmHg, and the tower top temperature was changed from 105 ° C / 15 mmHg to 106 ° C / 17 m.
A distillate of mHg was obtained. As a result of analysis by capillary gas chromatography, it was 98.
It was found that the mixed alcohol contained 3% by weight, 1.6% by weight as MPHO and 0.002% by weight as MEHO (hereinafter referred to as mixed alcohol (1)).

(4) Esterification In a 300-liter SUS reactor, 62 kg of phthalic anhydride as a raw material and the alcohol mixture (1) obtained above
163 kg was charged under a nitrogen atmosphere. The solution was heated with stirring, and when the temperature of the reaction solution reached 60 ° C., 1052 g of a 25 wt% decanol solution of tetraisopropoxy titanium as a catalyst was added, and then the temperature was further raised to 220 ° C. The produced water was removed to the outside of the system using an oil-water separator attached to the reactor, and the unreacted alcohol was returned to the inside of the system. Sampling was performed every hour after the temperature of the reaction solution reached 220 ° C, and when the acid value became 0.3 or less (about 5
After a lapse of time), heating was stopped, and after performing ordinary neutralization, washing with water, distillation under reduced pressure, and post-treatment operations, 174.7 kg of a target mixed phthalate (hereinafter referred to as DXP-1) was obtained.
At this time, the acid value is 0.021 and the residual alcohol content is 100 p.
It was pm or less and the water content was 0.07% by weight.

(5) Sheeting In order to evaluate the performance of the plasticizer of the present invention, the average degree of polymerization is 1
030 polyvinyl chloride homopolymer (Chisso Corporation; S
L) 100 parts by weight of DXP-1, 50 parts by weight, 4 parts by weight of tribasic lead sulfate and 1 part by weight of lead stearate were mixed with 100 parts by weight and kneaded with a test roll at 175 ° C. for 5 minutes. Then, make a sheet with a thickness of 1.3 mm, and
Preheat at 85 ° C for 2 minutes, then 150 kg / c for 3 minutes
A sheet having a thickness of 1 mm was prepared by pressurizing at a pressure of m ² , and each predetermined test piece was prepared using the sheet, and a tensile test, a heating weight change rate, a volume resistivity, an oil resistance test weight change rate,
Water resistance test Weight change rate, softening temperature, and hardness were measured. The measurement results are shown in Table-1.

Example 2 Regarding hydroformylation, the following (formula 2) was used as a ligand.
(1) of Example 1 except that the bisphosphite compound represented by (the molar ratio of the ligand and rhodium was 9.2) was used.
Hydroformylation of 1-butene was carried out according to

[Chemical 2] As a result, nVLA and 2MBA in the produced C5 aldehyde
It was found that the production ratio of and was 13.3: 1. The aldol condensation was carried out according to (2) of Example 1, and the hydrogenation reaction and vacuum distillation were carried out according to each of (3) of Example 1. However, the distillation temperature was 105.5 ° C / 16 mmHg to 106 ° C / 17 mmHg. The produced mixed decanol was analyzed by capillary gas chromatography, and as a result, 2PHO was 95.9% by weight, MP
Mixed alcohol containing 4.0% by weight of HO and 0.08% by weight of MEHO (hereinafter, mixed alcohol (2)
Say. ) Was found.

Then, (4) of Example 1 was repeated except that 163 kg of the mixed alcohol (2) obtained above was used.
Esterification was performed according to the above procedure to obtain 173.5 kg of a target mixed starate (hereinafter referred to as DXP-2).
Then, using DXP-2, a sheet was prepared according to (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Example 3 The oil layer after the hydrogenation reaction prepared according to Example 2 was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the tower top temperature is 102.9 ° C / 16 mmHg to 106 ° C
It was a distillate of / 17 mmHg. As a result of analyzing this by capillary gas chromatography, 25.9% by weight of PHO, 3.5% by weight of MPHO, M
It was found that the mixed alcohol contained 0.42% by weight as EHO (hereinafter referred to as mixed alcohol (3)). Esterification was carried out according to (4) of Example 1 except that 163 kg of the obtained mixed alcohol (3) was used, and mixed phthalate (hereinafter referred to as DXP-3) 17
2.7 kg was obtained. Then, using DXP-3, a sheet was prepared according to (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Example 4 A sheet was prepared in the same manner as in Example 1 except that 50 parts by weight of DXP-1 and 70 parts by weight of DXP-1 were used in (5) of Example 1 and the sheet was prepared. Various test pieces were prepared by using them, and various physical properties were measured. The results are shown in Table-1.

Example 5 A sheet was prepared in the same manner as in Example 1 except that 50 parts by weight of DXP-1 and 100 parts by weight of DXP-1 were used in (5) of Example 1 and the sheet was prepared. Various test pieces were prepared by using them, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 1 Regarding the hydroformylation, the following (formula 3) was used as a ligand.
(1) of Example 1 except that the bisphosphite compound represented by (the molar ratio of ligand to rhodium was 4.1) was used.
Hydroformylation of 1-butene was carried out according to

[Chemical 3] As a result, nVLA and 2MBA in the produced C5 aldehyde
It was found that the production ratio of and was 6.30: 1.

The aldol condensation, hydrogenation reaction and vacuum distillation were carried out according to (2) and (3) of Example 1. However,
Tower top temperature is 101.2 ℃ / 15mmHg to 106 ℃ / 1
It was a distillate of 7 mmHg. The produced mixed decanol was analyzed by capillary gas chromatography, and as a result, 84.7% by weight as 2PHO and 1 as MPHO.
Mixed alcohol containing 5.1% by weight and 0.18% by weight as MEHO (hereinafter referred to as mixed alcohol (4)).
I found out. (4) of Example 1 except that 163 kg of the mixed alcohol (4) obtained above was used.
176.3 kg of mixed phthalate (hereinafter referred to as DXP-4) was obtained according to the above. Then, using DXP-4, a sheet is prepared according to (5) of Example 1,
Various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 2 The oil layer after the hydrogenation reaction prepared according to Example 2 was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the tower top temperature is from 103 ° C / 16 mmHg to 106 ° C / 1
It was a distillate of 7 mmHg. As a result of analyzing this by capillary gas chromatography, 22.8% by weight of 2PHO, 6.6% by weight of MPHO, MEH
It was found to be a mixed alcohol containing 0.32% by weight of O (hereinafter referred to as mixed alcohol (5)).
Esterification was carried out according to (4) of Example 1 except that 163 kg of the obtained mixed alcohol (5) was used,
Mixed phthalate (hereinafter referred to as DXP-5) 171.
6 kg was obtained. Then, using DXP-5, a sheet was prepared in accordance with (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 3 The oil layer after hydrogenation reaction prepared according to (3) of Example 1 was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the distillation temperature was 104.5 ° C / 15 mmHg to 106 ° C / 17 mmHg. As a result of analyzing this by capillary gas chromatography, 2
It was found to be a mixed alcohol (hereinafter referred to as mixed alcohol (6)) containing 98.3% by weight of PHO, 1.2% by weight of MPHO, and 0.48% by weight of MEHO. Obtained mixed alcohol (6) 163k
Esterification was performed according to (4) of Example 1 except that g was used to obtain 177.5 kg of mixed phthalate (hereinafter referred to as DXP-6). Then, using DXP-6, a sheet is prepared according to (5) of Example 1,
Various test pieces were prepared using the obtained sheet, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 4 The oil layer after the hydrogenation reaction prepared according to Example 2 was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the tower top temperature is 103.5 ° C / 16mmHg to 106 ° C
It was a distillate of / 17 mmHg. As a result of analyzing this by capillary gas chromatography, 93.6 wt% as 2PHO, 6.2 wt% as MPHO, M
It was found to be a mixed alcohol containing 0.11% by weight of EHO (hereinafter referred to as mixed alcohol (7)). Esterification was carried out according to (4) of Example 1 except that 163 kg of the obtained mixed alcohol (7) was used, and mixed phthalate (hereinafter referred to as DXP-7) 1
73.2 kg was obtained. Then, using the DXP-7,
A sheet was prepared according to (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 5 The oil layer after the hydrogenation reaction prepared according to (3) of Example 1 was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the distillation temperature was 104.3 ° C / 15 mmHg to 106 ° C / 17 mmHg. As a result of analyzing this by capillary gas chromatography, 2
It was found that the mixed alcohol (hereinafter referred to as mixed alcohol (8)) contains 98.1% by weight of PHO, 1.1% by weight of MPHO, and 0.62% by weight of MEHO. Obtained mixed alcohol (8) 163k
172.9k of mixed phthalates (hereinafter referred to as DXP-8) based on (4) of Example 1 except that g was used.
g was obtained. Then, a sheet was prepared using the DXP-8 according to (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. Table of the results
Shown in 1.

Comparative Example 6 Rhodium dicarbonylacetylacetonate, (formula 1)
Approximately 15 ml of a catalyst precursor solution consisting of a bisphosphite ligand (molar ratio of ligand to rhodium is 8.6) and valeraldehyde trimer as a solvent (about 14 g, rhodium is the solution). 250 ppm, and the bisphosphite ligand is 2% by weight in the solution) with magnetic stirring 1
It was charged into a stainless steel reactor in which 00 ml of nitrogen had been replaced, and heated to 70 ° C. This reactor is 0.35
The pressure was reduced to Kg / cm ² G, and 25 ml of 1-butene (25 Kg / cm ² A) was introduced. Next, carbon monoxide and hydrogen (total pressure 7 Kg / cm ² A, CO (mol): H ₂
(Mol) = 1: 2} was introduced to hydroformylate 1-butene. The produced C5 aldehyde was analyzed by capillary gas chromatography to find that nVLA
And the production ratio of 2MBA was 50.5: 1. Then, aldol condensation and hydrogenation reaction were performed by the method according to (2) and (3) of Example 1, and the oil layer was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. However, the distillation temperature was 112 ° C. to 113 ° C./20 mmHg. As a result of analysis by capillary gas chromatography, this was 99.7% by weight as 2PHO, MP
Mixed alcohol containing 0.2% by weight as HO (hereinafter,
It is called mixed alcohol (9). ) Was found. Esterification was carried out according to (4) of Example 1 except that 163 kg of the obtained mixed alcohol (9) was used, and mixed phthalate (hereinafter referred to as DPHP) 17
0.8 kg was obtained. A sheet was prepared using the obtained DPHP in accordance with (5) of Example 1, and various test pieces were prepared using the sheet and various physical properties were measured. The results are shown in Table-1.

Comparative Example 7 A sheet was prepared according to (5) of Example 1 except that di-2-ethylhexyl phthalate (DOP: manufactured by Chisso Corporation) was used. Various test pieces were prepared using the sheet and various physical properties were measured. The results are shown in Table-1.

Comparative Example 8 A sheet was prepared in accordance with (5) of Example 1 except that diisononyl phthalate (DINP: manufactured by Sekisui Chemical Co., Ltd.) was used, and various test pieces were prepared using the sheet. Was prepared and various physical properties were measured. The results are shown in Table-1.

Comparative Example 9 A sheet was prepared according to (5) of Example 1 except that diisodecyl phthalate (DIDP: manufactured by Sekisui Chemical Co., Ltd.) was used. Various test pieces were prepared from the sheet and various physical properties were measured. The results are shown in Table-1.

Comparative Example 10 (1) Production of mixed alcohol of 2PHO and 2-isopropyl-1-heptanol and 5-methyl-2-propyl-1-heptanol n-valeraldehyde (manufactured by Tokyo Kasei Co., Ltd.) was used. Two
Fractionation was carried out using a 5-stage Oldershaw to obtain a product with a purity of 99.9% by weight. The reagent 3-methylbutyraldehyde (manufactured by Tokyo Chemical Industry Co., Ltd .: Isovaleraldehyde) was rectified by a 25-stage Oldershaw to obtain a product having a purity of 99.9% by weight. A 2 liter four-necked flask equipped with a magnetic stirrer, Dimroth condenser, thermocouple thermometer, and dropping device was charged with 316.1 g of rectified n-valeraldehyde and 35.1 g of rectified 3-methylvaleraldehyde. It was stirred. 1.
355.0 g of 25 wt% NaOH aqueous solution was prepared, and this was added dropwise to the flask at 25 ° C. The dropping was completed after 60 minutes, and the temperature in the system at this time was 59 ° C. After that, heating was started, and stirring was continued for 4 hours after reaching 85 ° C. Next, after cooling to room temperature, stirring was stopped and oil-water separation was performed to obtain 291.0 g (water content 0.61% by weight) of an oil layer.

Next, in a 500 ml stainless steel autoclave equipped with a magnetic stirrer, a hydrogen pressure regulator and a thermocouple thermometer, 267.1 g of an oil layer of the aldol condensation solution prepared above and 13.4 g of Raney nickel as a catalyst under a nitrogen atmosphere. Was charged, the inside of the system was replaced with hydrogen three times, and then the hydrogen pressure was set to 50 kg / cm ² G, and
It was stirred at 00 rpm. At the same time, when the electric furnace was heated to raise the temperature, hydrogen absorption started at an internal temperature of about 95 ° C., and hydrogen absorption continued for 4 hours thereafter (the highest temperature reached during that time was 160 ° C.). After the hydrogen absorption was stopped, the stirring was continued at 130 to 145 ° C. for another 2 hours, and then the heating was stopped. After standing overnight, the catalyst was filtered off with a membrane filter to obtain 269.3 g of an oil layer. This oil layer was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. Decompression degree 30 to 60 at the beginning of distillation
Operate at mmHg, then reduce pressure to 10 to 30 mmH
g to change the tower top temperature from 101 ° C / 15 mmHg to 10
A distillate of 6 ° C./17 mmHg was obtained. As a result of analyzing this by capillary gas chromatography, 2PHO
82.5% by weight, 2-isopropyl-1-heptanol. 9.0% by weight, 5-methyl-2-propyl-1-
A mixed decyl alcohol (hereinafter referred to as a mixed alcohol (10)) containing 8.3% by weight of heptanol and 0.09% by weight of 5-methyl-2-isopropyl-1-heptanol was obtained.

(2) 4,4-dimethyl-2-propyl-
Production of 1-pentanol 2 parts of reagent n-valeraldehyde (manufactured by Tokyo Kasei Co., Ltd.)
Fractionation was carried out using a 5-stage Oldershaw to obtain a product with a purity of 99.9% by weight. Reagent pivalaldehyde (Tokyo Kasei Co., Ltd.)
Was rectified with a 25-stage Oldershaw to obtain a product having a purity of 99.9% by weight. N-barrel aldehyde rectified in a 2-liter four-necked flask equipped with a magnetic stirrer, Dimroth condenser, thermocouple thermometer, and dropping device.
0 g and 35.2 g of rectified pivalaldehyde were charged and stirred. 355.0 g of a 1.25 wt% NaOH aqueous solution was prepared, and this was added dropwise to the flask at 25 ° C. 60
After a lapse of minutes, the dropping was completed, and the temperature in the system at this time was 55 ° C. After that, heating was started, and stirring was continued for 5 hours after reaching 85 ° C. Next, after cooling to room temperature, stirring was stopped and oil-water separation was performed to obtain 290.2 g (water content 0.55% by weight) of an oil layer. Next, in a 500 ml stainless steel autoclave equipped with a magnetic stirrer, a hydrogen pressure regulator and a thermocouple thermometer, 267.1 g of an oil layer of the prepared aldol condensate and 13.5 g of Raney nickel as a catalyst were charged under a nitrogen atmosphere. After the system was replaced with hydrogen three times, the hydrogen pressure was set to 50 Kg / cm ² G,
It was stirred at 500 rpm. At the same time, when the electric furnace was heated to start raising the temperature, hydrogen absorption started at an internal system temperature of around 95 ° C., and hydrogen absorption continued for 4 hours thereafter (the highest temperature reached during that time was 160 ° C.). After continuing the stirring at 130 to 145 ° C. for another 2 hours after the hydrogen absorption was stopped, the heating was stopped. After standing overnight, the catalyst was filtered off using a membrane filter, and the result was 269.3.
g oil layer was obtained. This oil layer was distilled under reduced pressure using a 25-stage Oldershaw distillation apparatus. At the beginning of distillation, the pressure reduction degree was 30 to 60 mmHg, and then the pressure reduction degree was 10 to 30 m.
The distillation temperature was changed to mHg to obtain a distillate having a tower top temperature of 101 ° C./15 mmHg to 108 ° C./16 mmHg. As a result of analyzing this by capillary gas chromatography, 2P
A mixed decyl alcohol having HO of 82.4% by weight and 4,4-dimethyl-2-propyl-1-pentanol of 17.5% by weight (hereinafter, referred to as mixed alcohol (11)) was obtained.

(3) Preparation of Mixed Alcohol Mixed alcohol (9) obtained according to Comparative Example 6, mixed alcohol (10) obtained in (1) above and mixed alcohol (11) obtained in (2) above. To 100: 0.0026:
When the composition of the alcohol prepared by mixing at a ratio of 0.0013 was analyzed by capillary gas chromatography, the following composition was obtained. 2PHO 99.7% by weight MPHO 0.23% by weight MEHO 0.001% by weight or less 2-isopropyl-1-heptanol 0.023 5-methyl-2-propyl-1-heptanol 0.022 4,4-dimethyl-2 -Propyl-1-pentanol 0.023 This mixed alcohol contains 0.23% by weight of alcohol derived from the condensation reaction of n-valeraldehyde and 2-methylbutyraldehyde, n-valeraldehyde and 3-methylbutyraldehyde. 0.045% by weight of the alcohol derived from the condensation reaction with, and 0.02% of the alcohol derived from the condensation reaction of n-valeraldehyde and pivalaldehyde.
3% by weight, other alcohol having 10 carbon atoms 0.001
It becomes weight%.

163 kg of the alcohol prepared above
170.4k of mixed phthalate (hereinafter referred to as D10P-1) according to (4) of Example 1 except that
g was obtained. Next, using the obtained D10P-1, a sheet was prepared according to (5) of Example 1, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

Comparative Example 11 Based on the mixed alcohol (9) obtained according to Comparative Example 6, the mixed alcohol (10) obtained according to (1) of Comparative Example 10 and the (2) of Comparative Example 10. The composition of the alcohol prepared by mixing the obtained mixed alcohol (11) in a ratio of 100: 0.026: 0.013 was analyzed by capillary gas chromatography. 2PHO 99.1% by weight MPHO 0.22% by weight MEHO 0.001% by weight or less 2-isopropyl-1-heptanol 0.23 5-methyl-2-propyl-1-heptanol 0.22 4,4-dimethyl-2 -Propyl-1-pentanol 0.23 This mixed alcohol contains 0.22% by weight of an alcohol having a skeleton of a condensation product of n-valeraldehyde and 2-methylbutyraldehyde, and n-valeraldehyde and 3-.
0.45% by weight of an alcohol having a skeleton of a condensation product with methylbutyraldehyde, 0.23% by weight of an alcohol having a skeleton of a condensation product of n-valeraldehyde and pivalaldehyde, and 10 other carbon atoms. It was found to be a mixed alcohol of 0.001% by weight.

163 kg of the mixed alcohol prepared above
Esterification was carried out according to (4) of Example 1 except that the above was used to obtain 170.2 kg of mixed phthalate (hereinafter referred to as D10P-2). Next, using the D10P-2, a sheet was prepared according to (5) of Example 1,
Various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-1.

[Table 1]

[Table 2]

Example 6 A 2-liter glass four-necked flask was charged with 438.3 g of adipic acid as a raw material and 1138.3 g of the mixed alcohol (1) obtained according to Example 1 under a nitrogen atmosphere.
This solution was heated with stirring, and when the temperature of the reaction solution reached 173 ° C., 1.8 g of tetraisopropoxy titanium as a catalyst was added, and then the temperature was further raised to 220 ° C.
The produced water was removed to the outside of the system using an oil-water separator attached to the reactor, and the unreacted alcohol was returned to the inside of the system. Sampling was performed every hour after the temperature of the reaction solution reached 220 ° C., heating was stopped when the acid value became 0.1 or less (after about 3.5 hours), and normal neutralization, Washing with water, vacuum distillation (9
After cutting a fraction of 0 ° C./50 mmHg to 210.5 ° C./1.5 mmHg) and a post-treatment operation, a mixed adipate (hereinafter referred to as DXA) 1130.
9 g was obtained. At this time, the acid value was 0.023, the residual alcohol content was 100 ppm or less, and the water content was 0.03% by weight.

Next, in order to evaluate the above DXA, polyvinyl chloride having an average degree of polymerization of 1030 (Chisso Corporation; S
L) 100 parts by weight, DXA 40 parts by weight and calcium-zinc-based stabilizer 2 parts by weight were blended, and this was kneaded with a test roll at 170 ° C. for 5 minutes to prepare a sheet having a thickness of 1.3 mm. The sheet was preheated at 180 ° C. for 4 minutes and then pressurized at a pressure of 180 kg / cm ² for 2 minutes and cooled at a pressure of 180 kg / cm ² for 3 minutes to prepare a sheet having a thickness of 1 mm. Various test pieces were prepared using the sheet, and specific gravity, heating weight change rate, oil resistance test weight change rate, softening temperature, and hardness were measured. The measurement results are shown in Table-2.

Comparative Example 12 Mixed alcohol (9) 113 obtained according to Comparative Example 6
Esterification was carried out in accordance with Example 6 except that 8.3 g was used to obtain 112.8 g of di-2-propylheptyl adipate (hereinafter referred to as DPHA). The DP
A sheet was formed using HA according to Example 6, and various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-2.

Comparative Example 13 Using commercially available di-2-ethylhexyl adipate (manufactured by Chisso Corporation; DOA), a sheet was prepared in accordance with Example 6, and various test pieces were prepared using the sheet. Various physical properties were measured. The results are shown in Table-2.

Example 7 Trimellitic anhydride (made by Wako Pure Chemical Industries, Ltd.) 384.
3 g and mixed alcohol (1) obtained according to Example 1
1138.8 g was charged under a nitrogen atmosphere, the solution was heated with stirring, and when the reaction solution temperature reached 173 ° C., 1.8 g of tetraisopropoxytitanium as a catalyst was added, and then the temperature was further raised to 220 ° C. The produced water was removed to the outside of the system using an oil-water separator attached to the reactor, and the unreacted alcohol was returned to the inside of the system. Sampling was carried out every hour after the temperature of the reaction solution reached 220 ° C., and when the acid value became 0.1 or less (after about 2.5 hours), heating was stopped and normal neutralization, Washing with water, vacuum distillation (80 ℃ / 20m
After performing mHg to 220 ° C./0.5 mmHg fraction) and post-treatment, 1166.8 g of mixed trimellitate (hereinafter referred to as TXTM), which is a target substance, was obtained. At this time, the acid value is 0.023 and the residual alcohol content is 15
The content was 0 ppm and the water content was 0.02% by weight.

Next, in order to evaluate the TXTM, polyvinyl chloride having an average degree of polymerization of 1030 (Chisso Corporation; S
L) 100 parts by weight, TXTM 50 parts by weight, tribasic lead sulfate 4 parts by weight, lead stearate 1 part by weight,
This was kneaded with a test roll at 170 ° C. for 5 minutes to prepare a sheet having a thickness of 1.3 mm, preheated at 180 ° C. for 4 minutes, and then pressurized at a pressure of 180 kg / cm ² for 2 minutes. The sheet was cooled for 3 minutes at a pressure of 180 kg / cm ² to prepare a sheet having a thickness of 1 mm. Various test pieces were prepared using the sheet, and specific gravity, heating weight change rate, oil resistance test weight change rate, softening temperature, and hardness were measured. The measurement results are shown in Table-3.

Comparative Example 14 Mixed alcohol (9) 113 obtained according to Comparative Example 6
Esterification was performed according to Example 6 except that 8.9 g was used to obtain 1165.7 g of tri-2-propylheptyl trimellitate (hereinafter referred to as TPHTM). The TPHTM was used to form a sheet according to Example 6, various test pieces were prepared using the sheet, and various physical properties were measured. The results are shown in Table-3.

Comparative Example 15 Using commercially available tri-2-ethylhexyl trimellitate (manufactured by Chisso Corporation; TOTM), a sheet was prepared in accordance with Example 6, and various test pieces were prepared using the sheet. Then
Various physical properties were measured. The results are shown in Table-3.

[Table 3]

Example 8 In a 2-liter glass four-necked flask, 505.7 g of the reagent sebacic acid (manufactured by Wako Pure Chemical Industries, Ltd.) as raw materials and the mixed alcohol (1) obtained according to Example 1 were contained. 94
9.2 g of the solution was charged under a nitrogen atmosphere, and the solution was heated with stirring. When the temperature of the reaction solution reached 173 ° C., 1.8 g of tetraisopropoxytitanium as a catalyst was added, and the temperature was further raised to 220 ° C. The produced water was removed to the outside of the system using an oil-water separator attached to the reactor, and the unreacted alcohol was returned to the inside of the system. After the temperature of the reaction solution reached 220 ° C, sampling was performed every hour, and the acid value was 0.1.
When the temperature falls below (after about 2.5 hours), stop heating and perform normal neutralization, washing with water, and vacuum distillation (90 ° C / 20 mmH).
After cutting off a fraction of g to 200 ° C./0.5 mmHg) and performing a post-treatment, 118.3 g of mixed sebacate (hereinafter referred to as DXS), which is the target substance, was obtained. At this time, the acid value was 0.031, the residual alcohol content was 100 ppm or less, and the water content was 0.03% by weight.

Next, in order to evaluate the DSX, polyvinyl chloride having an average degree of polymerization of 1030 (Chisso Corporation; SL)
50 parts by weight of DXS, calcium-based on 100 parts by weight
2 parts by weight of a zinc-based stabilizer was mixed, and this was kneaded with a test roll at 170 ° C. for 5 minutes to prepare a sheet having a thickness of 1.3 mm. Further, this was preheated at 180 ° C. for 4 minutes and then pressurized at a pressure of 180 kg / cm ² for 2 minutes and cooled at a pressure of 180 kg / cm ² for 3 minutes to prepare a sheet having a thickness of 1 mm. Various test pieces were prepared using the sheet, and specific gravity, heating weight change rate, oil resistance test weight change rate, softening temperature, and hardness were measured. The measurement results are shown in Table-4.

Comparative Example 16 Mixed alcohol (9) 949.
Esterification was performed according to Example 6 except that 3 g was used to obtain 1122.5 g of di-2-propylheptyl sebacate (hereinafter referred to as DPHS). The D
A sheet was prepared using PHS in accordance with Example 6, various test pieces were prepared using the sheet, and various physical properties were measured.
The results are shown in Table-4.

Comparative Example 17 Commercially available 2-ethylhexanol (Chisso Corporation; OA)
Esterification was performed according to Example 6 except that 841.3 g was used to obtain 1023.6 g of di-2-ethylhexyl sebacate (hereinafter referred to as DOS). The D
A sheet was formed using OS in accordance with Example 6, various test pieces were prepared from the sheet, and various physical properties were measured. The results are shown in Table-4.

Example 9 In a 2 liter glass four-necked flask, 470.6 g of azelaic acid as a raw material (manufactured by Wako Pure Chemical Industries, Ltd.) as a raw material and mixed alcohol (1) 94 obtained according to Example 1 were used.
9.3 g was charged under a nitrogen atmosphere, the solution was heated with stirring, and when the reaction solution temperature reached 173 ° C., 1.8 g of tetraisopropoxy titanium as a catalyst was added,
Furthermore, it heated up to 220 degreeC. The produced water was removed to the outside of the system using an oil-water separator attached to the reactor, and the unreacted alcohol was returned to the inside of the system. Sampling was carried out every hour after the temperature of the reaction solution reached 220 ° C., and when the acid value became 0.1 or less (after about 2.5 hours), heating was stopped and normal neutralization, Washing with water, distillation under reduced pressure (90 ° C / 20 mmHg-2
After performing a cutting treatment at 00 ° C./0.5 mmHg fraction) and a post-treatment operation, a mixed azelate (hereinafter,
1079.0 g was obtained. At this time, the acid value was 0.038, the residual alcohol content was 100 ppm or less, and the water content was 0.04% by weight.

Next, in order to evaluate the DXZ, polyvinyl chloride having an average degree of polymerization of 1030 (Chisso Corporation; SL)
50 parts by weight of DXZ and 3 parts by weight of calcium-zinc stabilizer were mixed with 100 parts by weight, and this was kneaded for 5 minutes with a test roll at 170 ° C. to prepare a sheet having a thickness of 1.3 mm. After preheating this at 180 ° C for 4 minutes,
Pressurized at a pressure of 180 kg / cm ² for ² minutes, 18 for 3 minutes
The sheet was cooled at a pressure of 0 kg / cm ² to prepare a sheet having a thickness of 1 mm. Various test pieces were prepared using the sheet, and specific gravity, heating weight change rate, oil resistance test weight change rate, softening temperature, and hardness were measured. The measurement results are shown in Table-5.

Comparative Example 18 Mixed alcohol (9) 949.
Esterification was carried out according to Example 6 except that 3 g was used to obtain 1074.1 g of di-2-propylheptyl azelate (hereinafter referred to as DPHZ). The D
A sheet was prepared using PHZ in accordance with Example 6, various test pieces were prepared using the sheet, and various physical properties were measured.
The results are shown in Table-5.

Comparative Example 19 Commercially available 2-ethylhexanol (Chisso Corporation; OA)
Esterification was performed according to Example 6 except that 841.1 g was used to obtain 1004.9 g of di-2-ethylhexyl azelate (hereinafter referred to as DOZ). The DO
A sheet was prepared by using Z in accordance with Example 6, various test pieces were prepared from the sheet, and various physical properties were measured. The results are shown in Table-5.

[Table 4]

[0066]

The plasticizer obtained by using the mixed alcohol for a plasticizer having the composition of the present invention has a heat resistance (heat aging resistance), an oil resistance and a cold resistance (low temperature flexibility) when the plasticizer is blended with a resin. ) Is an excellent plasticizer capable of obtaining a resin composition excellent in the above), and the mixed alcohol of the present invention is a mixed alcohol for a plasticizer which gives the above excellent plasticizer. .

Claims (3)

[Claims] 1. When a plasticizer is produced by esterifying an alcohol having 10 carbon atoms with a carboxylic acid or a carboxylic acid anhydride, 2PHO is 95 to 9 as the composition of the alcohol to be subjected to the esterification reaction.
8.5 wt%, MPHO 1.5-5 wt% and MEH
O is 0.5% by weight or less; mixed alcohol for plasticizers (however, 2PHO is 2-propyl-1-
As for heptanol, MPHO represents 4-methyl-2-propyl-1-hexanol, and MEHO represents 2-methyl-2-ethyl-1-heptanol. ). 2. A plasticizer obtained by subjecting the mixed alcohol for a plasticizer according to claim 1 to an esterification reaction with a carboxylic acid or a carboxylic acid anhydride. 3. The carboxylic acid or carboxylic acid anhydride is phthalic acid, phthalic acid anhydride, adipic acid, azelaic acid, sebacic acid, trimellitic acid, trimellitic acid anhydride, pyromellitic acid or pyromellitic acid anhydride. The plasticizer according to claim 2.