KR102520601B1 - Novel dicyclohexyl ester composition and preparation thereof - Google Patents

Abstract

The present invention relates to a novel dicyclohexyl ester composition (DCA) and a method for producing the same, and more particularly, to a cyclohexane-based compound, a by-product generated during the production of 1,4-cyclohexane dimethanol (CHDM), as a starting material. A novel di- A cyclohexyl ester composition (DCA) is provided, and the dicyclohexyl ester composition (DCA) thus provided can be widely applied as a plasticizer for PVC and adhesives or a plasticizer for paints and other resin additives.

Description

Novel dicyclohexyl ester composition and preparation method thereof {Novel dicyclohexyl ester composition and preparation thereof}

The present invention relates to a novel dicyclohexyl ester composition (DCA), and specifically, cyclohexane-based methyl ester, which is a by-product produced during the manufacturing process of 1,4-cyclohexane dimethanol (CHDM). A novel cyclohexane-based ester composition (DCB) is obtained through transesterification of the compound with a monohydric alcohol, and cyclohexane-based alcohol, a by-product produced in the process of obtaining the cyclohexane-based ester composition (DCB), is mixed with an organic acid. It relates to a novel dicyclohexyl ester composition (DCA) obtained through an ester reaction of and a method for preparing the same.

1,4-Cyclohexane dimethanol (CHDM) is a basic raw material for polyester or polyamide resin production, and is currently commercially available in Asia as a joint venture between SK Chemicals, Mitsubishi Corporation, and Shin Nippon Rika. Indorama [(former) Eastman] is preoccupying the entire market worldwide. In the CHDM market, demand for high value-added polyester resins is increasing, and is expected to increase in the future.

According to what is known in the literature, dimethyl terephthalate (DMT) is hydrogenated to dimethyl-β-cyclodextrin (DMCD) through 1,4-cyclohexane dimethanol (1,4- Cyclohexane dimethanol, CHDM) is produced (Scheme 1).

[Scheme 1]

In this process of producing 1,4-cyclohexane dimethanol (CHDM), low specific cyclohexane-based methyl esters and alcohol compounds are produced as by-products (FIG. 1).

Cyclohexane-based compounds, which are low-specific by-products generated in the CHDM manufacturing process, are substances containing cyclohexane-based methyl ester components and alcohol components in high concentrations. It is expected that the amount generated will increase further), and it is a material with high utilization value for the by-product cyclohexane-based compound, but the current situation is that the entire amount is incinerated.

If a commercially usable novel dicyclohexyl ester composition (DCA) can be produced using cyclohexane-based compounds, which are by-products that disappear by incineration, it can be used as plasticizers and other resin additives for PVC resins and adhesives or paints, It will be very useful in terms of recycling and development of new materials.

Korean Patent Registration No. 1731366 (2017.04.24)

Accordingly, the inventors of the present invention prepared a cyclohexane-based ester composition (DCB) by transesterifying a cyclohexane-based compound, which is a by-product of the 1,4-cyclohexanedimethanol (CHDM) manufacturing process (DMT hydrogenation process), with a monohydric alcohol. The present invention was completed by confirming that a dicyclohexyl ester composition (DCA) could be prepared through an esterification reaction of cyclohexane-based alcohol generated during the manufacturing process with an organic acid.

Accordingly, an object of the present invention is to provide a novel dicyclohexyl ester composition (DCA) that is commercially available and economically producible by utilizing a cyclohexane-based methyl ester compound, which is a by-product produced during the production of 1,4-cyclohexanedimethanol. And to provide a manufacturing method thereof.

In order to achieve the above object, the present invention utilizes a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol (CHDM), so that it can be commercially used and economically manufactured. A possible novel dicyclohexyl ester composition (DCA) and method for its preparation are provided.

The novel dicyclohexyl ester composition (DCA) according to the present invention uses a cyclohexane-based compound, which is a by-product generated during the production of 1,4-cyclohexane dimethanol (CHDM), as a starting material and undergoes a transesterification reaction with a monohydric alcohol. Provides a novel dicyclohexyl ester composition (DCA) that is economically and industrially usable through an esterification reaction of cyclohexane-based alcohol, a by-product generated in the process of manufacturing a cyclohexane-based ester composition (DCB), with an organic acid, , The dicyclohexyl ester composition (DCA) thus provided can be widely applied as a plasticizer for PVC and adhesives or a plasticizer for paints and other resin additives.

1 shows the generation of cyclohexane-based compounds, which are low specific by-products, and the dicyclohexyl ester composition (DCA) in the process of producing 1,4-cyclohexanedimethanol (CHDM) through hydrogenation of dimethyl terephthalate (DMT). It is a schematic diagram showing the manufacturing process.
Figure 2 shows the appearance of a transesterification reaction device for producing a cyclohexane-based ester composition (DCB).

Hereinafter, the present invention will be described in more detail.

The inventors of the present invention found that a cyclohexane-based compound, which is a low specific by-product produced as a by-product of the 1,4-cyclohexane dimethanol (CHDM) manufacturing process (DMT hydrogenation process), is transesterified with a monohydric alcohol to form a cyclohexane-based compound. Dicyclohexyl ester composition (DCA ) was found to be obtained and the present invention was completed.

Accordingly, the present invention provides a dicyclohexyl ester composition obtained by performing an esterification exchange reaction of a cyclohexane-based alcohol with an organic acid in the presence of a catalyst.

The cyclohexane-based alcohol produces a cyclohexane-based ester composition through a transesterification reaction of a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol (CHDM), with alcohol. It may be a by-product of the process.

The cyclohexane-based compound may include at least one selected from cyclohexane-based compounds represented by Formula 1:

[Formula 1]

In Formula 1, R ₁ is selected from hydrogen, methyl, hydroxyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl or methoxymethyl And, R ₂ may be selected from hydroxymethyl, acetoxymethyl, methoxycarbonyl or carboxyl.

More preferably, the cyclohexane-based compound is cyclohexane methanol (CHM), 4-methylcyclohexane methanol (MCHM), 4- (methoxymethyl) cyclohexylmethanol (4- At least one cyclohexane alcohol compound selected from the group consisting of (Methoxymethyl)cyclohexylmethanol (EMO) and 1,4-cyclohexane dimethanol (CHDM), and methyl 4-methylcyclohexanecarboxylate (Methyl 4-methylcyclohexanecarboxylate, 4-methyl methylate), Methyl 4-(hydroxymethyl)cyclohexanedcarboxylate (MOL) and dimethyl cyclohexane-1,4-dicarboxylate (Dimethyl 1,4-cyclohexanedicarboxylate, DMCD) may include one or more cyclohexane-based methyl ester compounds selected from the group consisting of.

In particular, the components of the cyclohexane-based compound used in the present invention are shown in Table 1.

Substance name CHM 4-methyl methylate MCHM EMO MOL DMCD CHDM total content(%) 3 to 8 1 to 5 25 to 40 20 to 35 15 to 25 5 to 15 0.5 to 5 100 1. CHM: Cyclohexane methanol
2. 4-methyl methylate : Methyl 4-methylcyclohexanecarboxylate
3. MCHM: 4-Methyl cyclohexane methanol
4. EMO: 4-(Methoxymethyl)cyclohexylmethanol
5. MOL: Methyl 4-(hydroxymethylcyclohexanedcarboxylate
6. DMCD: Dimethyl 1,4-cyclohexanedicarboxylate
7. CHDM: 1,4-Cyclohexane dimethanol

The cyclohexane-based compound is a cyclohexane-based alcohol component (CHM, MCHM, EMO, CHDM, content 70 _to 95%, alcohol- ₁ ) and a methyl ester component (Methyl ester, ME compound, 4- methyl methylate, MOL, DMCD, content 5 to 30%).

The alcohol used in the present invention is at least one C3 to C12 alcohol selected from the group consisting of propanol, isopropanol, butanol, isobutanol, octanol, isooctanol, nonanol, isononanol, decanol, isodecanol, and dodecanol. It may be, but is not limited thereto.

The cyclohexane-based ester composition may be obtained by including a cyclohexane-based alcohol compound and an alcohol in a molar ratio of 1: (1 to 10), preferably 1: (1 to 5), more preferably 1: It may be a molar ratio of (2.3 to 2.8).

The organic acid used in the present invention is a polybasic acid selected from adipic acid, oxalic acid, succinic acid, glutaric acid, sebacic acid, phthalic anhydride, isophthalic acid, terephthalic acid, maleic anhydride, citric acid or trimellitic acid; And it may be at least one selected from the group consisting of monobasic acids selected from benzoic acid and butyric acid, but is not limited thereto.

The dicyclohexyl ester composition may be obtained by including an organic acid and a cyclohexane-based alcohol compound in a molar ratio of 1: (1 to 10), preferably 1: (2.5 to 4).

The catalyst used in the present invention is tetra ethyl titanate, tetra N-propyl titanate, tetra isopropyl titanate, tetra N-butyl titanate, tetra isobutyl titanate, tetra 2-ethylhexyl titanate or a tin-based compound. selected organometallic catalysts; an organic or inorganic acid selected from paratoluene sulfonic acid, methane sulfonic acid, ethane sulfonic acid, dimethyl sulfate or sulfuric acid; And it may be at least one selected from the group consisting of ion exchange resins, but is not limited thereto.

In this regard, as a result of research on how to utilize cyclohexane-based compounds, which are CHDM by-products, the present inventors were able to prepare a cyclohexane-based ester composition (DCB) through transesterification with monohydric alcohol, and DCB production As a result of repeated examinations on the recycling of cyclohexane-based alcohol, which is a by-product generated in the process, a novel dicyclohexyl ester composition (DCA, Chemical Formula 2) can be obtained through an esterification reaction with an organic acid, and the dicyclohexyl The ester composition may include two or more dicyclohexyl ester compounds represented by Formula 2:

[Formula 2]

In Formula 2, R ₁ is selected from a straight-chain alkenyl group or phenyl group having 2 to 10 carbon atoms, R ₂ and R ₃ may be the same or different, and may be selected from hydrogen, methyl, methoxy or hydroxymethyl. .

In addition, a plasticizer composition for adhesives or paints containing the dicyclohexyl ester composition is provided.

In addition, the present invention comprises the steps of transesterifying a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol (CHDM), with alcohol; and performing an esterification reaction of cyclohexane-based alcohol generated as a by-product in the transesterification reaction with an organic acid in the presence of a catalyst.

More specifically, the present invention comprises the steps of (a) obtaining a cyclohexane-based compound as a by-product during the production of 1,4-cyclohexane dimethanol (CHDM); (b) treating the cyclohexane-based compound as a by-product with a monohydric alcohol to obtain cyclohexane-based alcohol generated while producing cyclohexane-based ester (DCB) through transesterification; (c) preparing a dicyclohexyl ester mixture through an esterification reaction of the cyclohexane-based alcohol with an organic acid under a catalyst; and (d) adding a neutralizing agent to the dicyclohexyl ester mixture obtained in step (c) to remove unreacted organic acid and catalyst through a neutralization reaction. A method for preparing a dicyclohexyl ester composition (DCA) using a by-product is provided.

First, the cyclohexane-based compound (Formula 1), which is a by-product used in step (a), is specifically cyclohexane methanol (CHM), methyl 4-methylcyclohexanecarboxylate (Methyl 4-methylcyclohexanecarboxylate, 4 -methyl methylate), 4-Methyl cyclohexane methanol (MCHM), 4-(Methoxymethyl)cyclohexylmethanol (EMO), methyl 4-(hydroxymethyl) Cyclohexanecarboxylate (Methyl 4-(hydroxymethyl) cyclohexanedcarboxylate (MOL), Dimethyl 1,4-cyclohexanedicarboxylate (DMCD), and 1,4-cyclohexane dimethanol (1 , 4-Cyclohexane dimethanol, CHDM) may include one or more selected from the group consisting of.

The esterification reaction between cyclohexane-based alcohol and organic acid in step (c) is a generally well-known esterification reaction, and the cyclohexane-based alcohol used in this step is cyclohexane-based alcohol (Table 1). At least one selected from the group consisting of basic acids adipic acid (AA), phthalic anhydride (PA), isophthalic acid (IPA), terephthalic acid (TPA), maleic anhydride (MA), and tribasic acid trimellitic acid (TMA). can be used

In particular, according to one embodiment, a dicyclohexane ester composition (DCA) may be prepared as shown in Scheme 2 below:

[Scheme 2]

In Scheme 2, R ₁ is selected from hydrogen, methyl, methoxy, or hydroxymethyl, and R ₂ may be selected from a straight-chain alkyl group having 2 to 10 carbon atoms, an alkenyl group, or a phenyl group.

As another example, the cyclohexane-based alcohol among the by-products may be 4-(Methoxymethyl)cyclohexnemethanol (MCHM). In other words, 4-(methoxymethyl)cyclohexylmethanol (MCHM), a cyclohexane-based alcohol, can produce dicyclohexyl adipate and water through an esterification reaction with an organic acid, adipic acid (Scheme 3).

[Scheme 3]

As shown in Reaction Scheme 3, the theoretical reaction molar ratio of adipic acid and alcohol is 1:2 and general esterification is 1:2.5 to 3, but in the present invention, the characteristics of the by-product cyclohexane alcohol (including mixed alcohol and some ester compounds) ) and mild reaction conditions (reaction time, reaction temperature), the molar ratio of adipic acid and by-product cyclohexane alcohol is 1: 4, and the reaction temperature is preferably carried out at 220 to 240 ° C. .

The catalyst includes tetra ethyl titanate, which is tetra alkyl titanate, tetra N-propyl titanate, tetra isopropyl titanate, and selected from tetra N-butyl titanate (TNBT), tetra isobutyl titanate (TIBT) or tetra 2-ethylhexyl titanate (TEHT), or sulfuric acid It may be an organic or inorganic acid selected from sulfuric acid, p-toluene sulfonic acid (PTSA), methane sulfonic acid, ethane sulfonic acid, dimethyl sulfate or sulfuric acid, which is a catalyst-based catalyst, and may be used in an amount of 0.05 to 1% by weight based on the total weight of by-products, but this depends on the reaction conditions. can be adjusted accordingly.

Step (d) is a step of removing unreacted adipic acid and catalyst through a neutralization reaction of the dicyclohexyl ester product obtained in step (c) using a neutralizing agent. The neutralizing agent used at this time is sodium hydroxide (NaOH), potassium hydroxide (KOH), calcium hydroxide [Ca(OH) ₂ ], sodium carbonate (Na ₂ CO ₃ ), sodium carbonate (Na ₂ CO ₃ ), potassium carbonate (K ₂ CO ₃ ), calcium carbonate (CaCO ₃ ), and the like. In addition, neutralization water may be used together to perform neutralization and layer separation. At this time, it is preferable to treat the neutralizer and neutralization water, raise the temperature to 90 to 95 ° C. while stirring, and neutralize for 1 to 2 hours by maintaining the temperature at 95 to 100 ° C. In addition, the product obtained after neutralization is distilled under reduced pressure to purify water and excess cyclohexane-based alcohol, and finally a novel dicyclohexyl ester composition (DCA) can be obtained through the process of decolorization and filtration.

Therefore, the novel dicyclohexyl ester composition (DCA) according to the present invention is a cyclohexane-based ester through a transesterification reaction of a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol, with a monohydric alcohol. The composition (DCB) can be prepared. Cyclohexane-based alcohol generated in this process can be obtained by esterification with an organic acid, and the dicyclohexyl ester composition (DCA) obtained in this way can be widely applied as a plasticizer for PVC and adhesives or paints and other resin additives.

Hereinafter, the present invention will be described in more detail by the following examples. However, the present invention is not limited by these examples.

Reference Example 1

As shown in FIG. 2, in a reaction apparatus equipped with a thermometer, a stirrer, and a cooler, 800 g (4.07 moles of alcohol-1 moles) of a by-product, cyclohexane-based compound, 693 g (9.36 moles) of butanol (alcohol-2), and 0.8 g of TNBT as a catalyst were added and heated. Stir. The closed system reaction (A) was carried out while the temperature of the reactor was raised, and when the reactor temperature reached 130 ° C., butanol was continuously introduced into the open system reaction (B), and the generated methanol was discharged out of the system together with excess butanol. Collected in a collector. Through the analysis of the reactants, the reaction was terminated when the ME content (excluding butanol) was 3%. Through this process, cyclohexane-based alcohol, a by-product generated during the production of a cyclohexane-based ester composition (DCB) using a cyclohexane-based compound, which is a by-product generated during the production of 1,4-cyclohexane dimethanol, was obtained.

Example 1

Thermometer, stirrer, cooler, separator [a device that is separated into a water layer (lower layer) and an alcohol layer (cyclohexane-based alcohol, upper layer) filled with water and cyclohexane-based alcohol, a by-product obtained in Reference Example 1, by half each] 365 g (2.5 mol) of adipic acid as a raw material, 1380 g (10.0 mol) of cyclohexane-based alcohol as a by-product, and 0.36 g of TNBT as a catalyst were put into a reaction apparatus equipped with heating and stirring. The temperature was raised to completely dissolve adipic acid, and then the esterification reaction proceeded while maintaining the reaction temperature at 220 to 240 °C. The reaction product water was discharged out of the system together with excess alcohol and collected in the separator, the product water was separated from the bottom of the separator, the alcohol was separated from the top, and the alcohol separated from the top was refluxed to the reactor. Through the analysis of reactants, the reaction was terminated when the acid value was 0.5 mg KOH/g.

The resulting dicyclohexyl ester product was purified by purification methods such as neutralization, dehydration and distillation, and activated carbon filtration. Table 1 below shows the composition of cyclohexane-based alcohol, which is a by-product used in Examples 1 to 3 and Comparative Examples 1 to 2.

Substance name CHM 4-methyl methylate MCHM EMO MOL DMCD CHDM total
(unit %) Example 1
Comparative Examples 1 and 2 10.4 1.0 59.2 24.2 2.9 1.3 1.0 100 Example 2 8.6 0.6 53.7 27.2 2.5 4.5 2.9 100 Example 3 6.2 0.4 42.6 41.0 7.4 1.4 1.0 100 1. CHM: Cyclohexane methanol
2. 4-methyl methylate : Methyl 4-methylcyclohexanecarboxylate
3. MCHM: 4-Methyl cyclohexane methanol
4. EMO: 4-(Methoxymethyl)cyclohexylmethanol
5. MOL: Methyl 4-(hydroxymethyl)cyclohexanedcarboxylate
6. DMCD: Dimethyl 1,4-cyclohexanedicarboxylate
7. CHDM: 1,4-Cyclohexane dimethanol

Example 2

The same procedure as in Example 1 was performed except that 365 g (2.5 mol) of adipic acid as a raw material, 1440 g (10.0 mol) of cyclic hexane alcohol as a by-product, and 0.36 g of TNBT as a catalyst were added to the reactor of Example 1.

Example 3

The same procedure as in Example 1 was performed except that 365 g (2.5 mol) of adipic acid as a raw material, 1450 g (10.0 mol) of cyclohexane alcohol as a by-product, and 0.36 g of TNBT as a catalyst were added to the reactor of Example 1.

Comparative Example 1

The same procedure as in Example 1 was performed except that 370 g (2.5 mol) of phthalic anhydride, 1380 g (10.0 mol) of cyclohexane alcohol as a by-product, and 0.37 g of TNBT as a catalyst were added to the reactor of Example 1 as raw materials.

Comparative Example 2

The same procedure as in Example 1 was performed except that 415 g (2.5 mol) of terephthalic acid as a raw material, 1440 g (10.0 mol) of cyclohexane alcohol as a by-product, and 0.42 g of TNBT as a catalyst were added to the reactor of Example 1.

Experimental example: measurement of physical properties

The alcohol content, color (APHA), acid value (mg KOH/g), and moisture content (%) of the dicyclohexyl ester compositions (DCA) prepared in Examples 1 to 3 and Comparative Examples 1 and 2 were measured. The results are shown in Table 2 below.

division Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 note Raw material organic acid adipic acid
365g phthalic anhydride
370g terephthalic acid
415g 2.5 moles cyclohex
acidic alcohol 1380g
(10.0 mol) 1440g
(10.0 mol) 1450g
(10.0 mol) 1380g
(10.0 mol) 1380g
(10.0 mol) usage 94.8% 92.4% 90.8% 94.8% 94.8% alcohol content organic acid:alcohol 1:4 mole ratio Catalyst (TNBT) 0.36g 0.37g 0.42g 0.1% compared to organic acid Reaction temperature (℃) 230 230 230 240 250 reaction final acid value
(mg KOH/g) 0.35 0.41 0.43 1.0 1.5 less than 0.5 reaction time 4 hours 5 hours 5 hours 8 hours 10 hours product sheep 1,058g 1,065g 1,070g 1,068g 1,063 yield 95.7 96.3 96.8 92.5 92.0 95% or more quality alcohol content 0.08 0.05 0.07 0.07 0.06 1% or less Color (APHA) 10 12 15 20 15 less than 20 Acid value (mg KOH/g) 0.05 0.04 0.03 0.05 0.- 0.1 or less Moisture content (%) 0.05 0.04 0.04 0.05 0.04 0.1 or less

As shown in Table 2, the dicyclosyl ester composition (DCA) obtained during the esterification reaction using the raw material cyclohexane-based alcohol and organic acid has color (APHA), acid value (mg KOH / g), moisture content ( %) was confirmed to satisfy the target physical property values, and when adipic acid was used as an organic acid, it was confirmed that it was advantageous in reaction time and yield.

Therefore, the present invention is an esterification reaction of cyclohexane-based alcohol generated during the production of a cyclohexane-based ester composition (DCB) using a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol, with an organic acid. A novel dicyclohexyl ester composition (DCA) that can be used industrially can be obtained economically and with high yield, and this dicyclohexyl ester composition (DCA) is also very useful as a plasticizer and other resin additives for PVC and adhesives or paints can be used

Having described specific parts of the present invention in detail above, it is clear to those skilled in the art that these specific descriptions are only preferred embodiments, and the scope of the present invention is not limited thereby. something to do. Accordingly, the substantial scope of the present invention will be defined by the appended claims and their equivalents.

Claims (10)

A dicyclohexyl ester composition obtained by performing an esterification reaction of a cyclohexane alcohol with an organic acid in the presence of a catalyst,
The dicyclohexyl-based ester composition, characterized in that the dicyclohexyl ester composition comprises two or more dicyclohexyl ester compounds represented by Formula 2:
[Formula 2]

In Formula 2, R ₁ is selected from a straight-chain alkyl group having 2 to 10 carbon atoms, an alkenyl group, or a phenyl group, and R ₂ and R ₃ may be the same or different, respectively, and selected from hydrogen, methyl, methoxy, or hydroxymethyl. The method of claim 1, wherein the cyclohexane-based alcohol is a cyclohexane-based compound produced during the production of 1,4-cyclohexane dimethanol (CHDM), which is a by-product, through a transesterification reaction with alcohol. A dicyclohexyl ester composition, characterized in that it is a by-product generated in the process of preparing a hexane-based ester composition. According to claim 2,
The cyclohexane-based compound is a dicyclohexyl ester composition, characterized in that it comprises at least one selected from the cyclohexane-based compounds represented by Formula 1:
[Formula 1]

In Formula 1, R ₁ is selected from hydrogen, methyl, hydroxyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl or methoxymethyl and R ₂ is selected from Hydroxymethyl, Acetoxymethyl, Methoxycarbonyl or Carboxyl. According to claim 2,
The cyclohexane-based compound is cyclohexane methanol (CHM), 4-methylcyclohexane methanol (MCHM), 4- (methoxymethyl) cyclohexylmethanol (4- (Methoxymethyl) cyclohexylmethanol, EMO) and at least one cyclohexane alcohol compound selected from the group consisting of 1,4-cyclohexane dimethanol (CHDM) and methyl 4-methylcyclohexanecarboxylate , 4-methyl methylate), methyl 4-(hydroxymethyl)cyclohexanedcarboxylate (MOL) and dimethyl cyclohexane-1,4-dicarboxylate (Dimethyl 1,4-cyclohexanedicarboxylate A dicyclohexyl ester composition comprising at least one cyclohexane-based methyl ester compound selected from the group consisting of DMCD). According to claim 1,
The organic acid is a polybasic acid selected from adipic acid, oxalic acid, succinic acid, glutaric acid, sebacic acid, phthalic anhydride, isophthalic acid, terephthalic acid, maleic anhydride, citric acid or trimellitic acid; and a monobasic acid selected from benzoic acid and butyric acid. According to claim 1,
The composition is a dicyclohexyl ester composition, characterized in that it comprises an organic acid and a cyclohexane-based alcohol compound in a molar ratio of 1: (1 to 10). According to claim 1,
The catalyst is an organometallic catalyst selected from tetra ethyl titanate, tetra N-propyl titanate, tetra isopropyl titanate, tetra N-butyl titanate, tetra isobutyl titanate, tetra 2-ethylhexyl titanate or a tin-based compound. ; an organic or inorganic acid selected from paratoluene sulfonic acid, methane sulfonic acid, ethane sulfonic acid, dimethyl sulfate or sulfuric acid; and an ion exchange resin. A dicyclohexyl ester composition comprising at least one selected from the group consisting of: delete A plasticizer composition for adhesives or paints comprising the dicyclohexyl-based ester composition of any one of claims 1 to 7. Performing a transesterification reaction with an alcohol for a cyclohexane-based compound, which is a by-product produced during the production of 1,4-cyclohexane dimethanol (CHDM); and
Performing an esterification reaction of cyclohexane-based alcohol generated as a by-product in the transesterification reaction with an organic acid in the presence of a catalyst
A method for preparing the dicyclohexyl ester composition according to claim 1, comprising:

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