WO2024232593A1 - Method for preparing mono-tert-butyl-esterified saturated hydrocarbon, and cyclic preparation method therefor - Google Patents

Abstract

The present application relates to a method for preparing a mono-tert-butyl-esterified saturated hydrocarbon, and a cyclic preparation method therefor. The method for preparing a mono-tert-butyl-esterified saturated hydrocarbon, according to embodiments of the present application, comprises processes that are easier than those of a conventional method and can be carried out under a mild condition. Unlike a conventional method, the method for preparing a mono-tert-butyl-esterified saturated hydrocarbon, according to embodiments of the present application does not generate impurities, and thus enables a mono-tert-butyl-esterified saturated hydrocarbon to be readily isolated and obtained.

Description

Method for producing mono-tert-butyl esterified saturated hydrocarbon and cyclical method for producing the same

The present invention relates to a method for producing a mono-tert-butyl esterified saturated hydrocarbon and a cyclic method for producing the same.

Semaglutide is a representative GLP-1 (glucagon-like peptide-1) analogue and is a medicine used for the treatment or prevention of diabetes. Octadecanedioic acid-mono-tert-butyl-ester (C ₂₂ H ₄₂ O ₄ ) is an intermediate for synthesizing semaglutide and is obtained by hydrolyzing di-tert-butyl-octadecanedioate (C ₂₆ H ₅₀ O ₄ ).

Various methods for hydrolysis of di-tert-butyl-esterified saturated hydrocarbons are known, but there are limitations such as low yield of the desired product, low purity due to formation of by-products, and high reaction temperature.

A previous literature, 'J. S. Yadav et al., "Montmorillonite Clay: A Novel Reagent for the Chemoselective Hydrolysis of t-Butyl Esters", Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India, 826-828', discloses a hydrolysis reaction using KSF clay as a catalyst. However, regardless of the amount of KSF clay used, all di-tert-butyl ester groups are hydrolyzed, making it difficult to synthesize the desired product.

Prior literature, 'Vassiliki Theodorou et al., "Mild alkaline hydrolysis of hindered esters in non-aqueous solution", Arkivoc 2018, part vii, 308-309', discloses a hydrolysis reaction using a strong base, but the target product is precipitated as a sodium salt, which hinders the progress of the reaction. In addition, after the completion of the reaction, the reaction solution becomes a slurry, making it difficult to isolate the target product, and there are disadvantages such as a long reaction time, low purity, and low conversion rate. US Patent Publication No. 2011-0306551 discloses a hydrolysis reaction using N,N-dimethylformamide di-tert-butylacetal and toluene as a solvent at 95°C, but due to the high reaction temperature, a large amount of impurities are generated, low purity, and it is difficult to recover the filtrate, so the yield is low. In the hydrolysis reaction disclosed in the previous literature, 'Giuseppe Bartoli et al., "Selective Deprotection of N-Boc-Protected tert-Butyl Ester Amino Acid by the CeCl ₃ 7H ₂ O-NaI System in Acetonitrile", J. Org. Chem. 2001, 66, 4430', the solvent in which the desired product is difficult to dissolve is used, so the reaction proceeds at a high temperature, resulting in low yield and purity.

U.S. Patent No. 1,026,6578 discloses a method using DMAP, 2-Me-THF, t-BuOH, and Boc ₂ O; a method using acetic anhydride, DMAP, and t-BuOH under an argon atmosphere; and a method using DMAP, Boc ₂ O, and toluene as a solvent. However, these methods have low purity due to the generation of a large amount of impurities due to the high reaction temperature, and the yield is low because it is difficult to recover the filtrate. In addition, it is difficult to apply it to a commercial process because silica gel chromatography is performed to purify the obtained product. European Patent No. 3,321,279 discloses a method using 1 equivalent each of DIC ( N,N′ -diisopropylcarbodiimide) and DMAP[4-(dimethylamino)pyridine]; and initiates a hydrolysis reaction using t-BuOH as a solvent, but is difficult to apply to a commercial process due to the column chromatography performed thereafter to purify the obtained product.

Therefore, there is a need for research on a method for producing octadecanedioic acid-mono-tert-butyl-ester in high yield and high purity, which is performed under mild reaction conditions, is applicable to industrialization, and is applicable to industrialization.

The present invention provides a method for producing a mono-tert-butyl esterified saturated hydrocarbon and a cyclic method for producing the same.

However, the problems that the present invention seeks to solve are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

The first aspect of the present invention provides a method for producing a mono-tert-butyl esterified saturated hydrocarbon, comprising subjecting a di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 to a hydrolysis reaction in the presence of a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 2, wherein the catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), zinc iodide (ZnI ₂ ), and hydrates thereof:

[Chemical Formula 1]

;

;

[Chemical formula 2]

;

;

In the above chemical formula 1 and the above chemical formula 2,

n is an integer greater than or equal to 1.

The second aspect of the present invention provides a cyclic method for producing a mono-tert-butyl esterified saturated hydrocarbon, comprising: performing a hydrolysis reaction of a di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 in the presence of a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula ₂ ; and performing the hydrolysis reaction in the presence of the catalyst on a filtrate of the hydrolysis reaction to additionally obtain a mono-tert-butyl esterified saturated hydrocarbon, at least once; wherein the catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl 2 ), zinc iodide (ZnI ₂ ), and hydrates thereof:

[Chemical Formula 1]

;

;

[Chemical formula 2]

;

;

In the above chemical formula 1 and the above chemical formula 2,

n is an integer greater than or equal to 1.

The method for producing a mono-tert-butyl esterified saturated hydrocarbon according to the embodiments of the present invention is easy to process and can be performed under mild conditions compared to conventional methods.

The method for producing a mono-tert-butyl esterified saturated hydrocarbon according to the embodiments of the present invention does not produce impurities compared to conventional methods, so that a mono-tert-butyl esterified saturated hydrocarbon can be easily separated and obtained.

In one embodiment of the present invention, the purity of the mono-tert-butyl esterified saturated hydrocarbon obtained by the method for producing a mono-tert-butyl esterified saturated hydrocarbon may be about 90% or more, about 95% or more, about 98% or more, or about 99% or more.

The method for producing a mono-tert-butyl esterified saturated hydrocarbon according to the embodiments of the present invention can be applied to a commercial process.

The cyclic production method of a mono-tert-butyl esterified saturated hydrocarbon according to the embodiments of the present invention is economical because the mono-tert-butyl esterified saturated hydrocarbon can be additionally obtained by performing the same hydrolysis reaction on the filtrate after the hydrolysis reaction.

The cumulative crystallization yield of the mono-tert-butyl esterified saturated hydrocarbon obtained by the cyclical production method of the mono-tert-butyl esterified saturated hydrocarbon according to the embodiments of the present disclosure can be about 40% or more, about 50% or more, about 60% or more, about 65% or more, about 70% or more, about 75% or more, about 80% or more, about 85% or more, or about 90% or more.

Figure 1 is a reaction scheme for a reaction of obtaining a mono-tert-butyl esterified saturated hydrocarbon by hydrolyzing a di-tert-butyl esterified saturated hydrocarbon in the presence of a zinc bromide catalyst, in one embodiment of the present invention, wherein n is an integer greater than or equal to 1.

Hereinafter, with reference to the attached drawings, the implementation examples and embodiments of the present invention will be described in detail so that those skilled in the art can easily practice the present invention. However, the present invention may be implemented in various different forms and is not limited to the implementation examples and embodiments described herein. In addition, in order to clearly explain the present invention in the drawings, parts that are not related to the description are omitted, and similar parts are assigned similar drawing reference numerals throughout the specification.

Throughout this specification, when a part is said to be "connected" to another part, this includes not only the case where it is "directly connected" but also the case where it is "electrically connected" with another element in between.

Throughout this specification, when it is said that an element is "on" another element, this includes not only cases where the element is in contact with the other element, but also cases where there is another element between the two elements.

Throughout this specification, whenever a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

The terms “about,” “substantially,” and the like, as used in this specification, are used in a meaning that is at or close to the numerical value when manufacturing and material tolerances inherent in the meanings mentioned are presented, and are used to prevent unscrupulous infringers from unfairly utilizing the disclosure in which exact or absolute values are mentioned to aid the understanding of the present application.

The terms “step of ~” or “step of ~” as used throughout this specification do not mean “step for ~.”

Throughout this specification, the term "combination(s) thereof" included in the expressions in the Makushi format means one or more mixtures or combinations selected from the group consisting of the components described in the Makushi format, and means including one or more selected from the group consisting of said components.

Throughout this specification, references to “A and/or B” mean “A or B, or A and B.”

Below, the implementation examples of the present invention are described in detail, but the present invention may not be limited thereto.

The first aspect of the present invention provides a method for producing a mono-tert-butyl esterified saturated hydrocarbon, comprising subjecting a di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 to a hydrolysis reaction in the presence of a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 2, wherein the catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), zinc iodide (ZnI ₂ ), and hydrates thereof:

[Chemical Formula 1]

;

;

[Chemical formula 2]

;

;

In the above chemical formula 1 and the above chemical formula 2,

n is an integer greater than or equal to 1.

In one embodiment of the present disclosure, n may be an integer from about 4 to about 22, but may not be limited thereto. In one embodiment of the present disclosure, n may be an integer from about 4 to about 22, from about 4 to about 18, from about 4 to about 14, from about 4 to about 10, from about 4 to about 6, from about 8 to about 22, from about 8 to about 18, from about 8 to about 14, from about 8 to about 10, from about 12 to about 22, from about 12 to about 18, from about 12 to about 16, from about 12 to about 14, from about 14 to about 22, from about 14 to about 18, or from about 20 to about 22. In one embodiment of the present disclosure, n may be about 6 to about 18. In one embodiment of the present disclosure, n may be 14. In one embodiment of the present invention, n may be 16.

In one embodiment of the present invention, the hydrolysis reaction may be performed in an environment including a catalyst selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), or zinc iodide (ZnI ₂ ); and water, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction may be performed in an environment including zinc bromide (ZnBr ₂ ) and water.

In one embodiment of the present invention, the hydrolysis reaction may be performed including a hydrate of zinc bromide (ZnBr ₂ ), a hydrate of zinc chloride (ZnCl ₂ ), or a hydrate of zinc iodide (ZnI ₂ ), but may not be limited thereto.

In one embodiment of the present invention, the catalyst may be zinc bromide (ZnBr ₂ ). In one embodiment of the present invention, the catalyst may be a hydrate of zinc bromide (as a non-limiting example, a dihydrate, ZnBr ₂ 2H ₂ O).

In one embodiment of the present invention, the catalyst may be used in an amount of more than about 0.2 equivalents and less than about 1 equivalent, but may not be limited thereto. In one embodiment of the present invention, the catalyst is present in an amount of from about 0.2 equivalents to about 1 equivalent or less, from about 0.2 equivalents to about 0.9 equivalents or less, from about 0.2 equivalents to about 0.8 equivalents or less, from about 0.2 equivalents to about 0.7 equivalents or less, from about 0.2 equivalents to about 0.6 equivalents or less, from about 0.3 equivalents to about 1 equivalent or less, from about 0.3 equivalents to about 0.9 equivalents or less, from about 0.3 equivalents to about 0.8 equivalents or less, from about 0.3 equivalents to about 0.7 equivalents or less, from about 0.3 equivalents to about 0.6 equivalents or less, from about 0.4 equivalents to about 1 equivalent or less, from about 0.4 equivalents to about 0.9 equivalents or less, from about 0.4 equivalents to about 0.8 equivalents or less, from about 0.4 equivalents to about It may be used in an amount of 0.7 equivalents or less, or from about 0.4 equivalents to about 0.6 equivalents or less. In one embodiment of the present invention, it may be preferable that the catalyst is used in an amount of about 0.5 equivalents.

In one embodiment of the present invention, when n is 14, about 100 mg to about 200 mg of zinc bromide may be used based on 1 mmol of the compound represented by the chemical formula 2. In one embodiment of the present invention, when the amount of zinc bromide is increased, the reaction time may be shortened, but all of the di-tert-butyl-ester groups of the compound represented by the chemical formula 1 may be hydrolyzed.

In one embodiment of the present invention, the hydrolysis reaction may be performed at a temperature range of about 0°C to about 40°C, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction is performed at a temperature of about 0°C to about 40°C, about 0°C to about 37°C, about 0°C to about 34°C, about 0°C to about 31°C, about 0°C to about 28°C, about 3°C to about 40°C, about 3°C to about 37°C, about 3°C to about 34°C, about 3°C to about 31°C, about 3°C to about 28°C, about 6°C to about 40°C, about 6°C to about 37°C, about 6°C to about 34°C, about 6°C to about 31°C, about 6°C to about 28°C, about 9°C to about 40°C, about 9°C to about 37°C, about 9°C to about 34°C, about 9°C to about 31°C, about 9°C to about 28°C, about 12°C to about 40°C, about 12°C to about 37°C, about 12°C to about 34°C, about 12°C to about 31°C, about 12°C to about 28°C, about 15°C to about 40°C, about 15°C to about 37°C, about 15°C to about 34°C, about 15°C to about 31°C, about 15°C to about 28°C, about 18°C to about 40°C, about 18°C to about 37°C, about 18°C to about 34°C, about 18°C to about 31°C, about 18°C to about 28°C, about 21°C to about 40°C, about 21°C to about 37°C, about 21°C to about 34°C, about 21°C to about 31°C, about 21°C to about 28°C, about 24°C to about 40°C, about It may be performed at a temperature range of from about 24° C. to about 37° C., from about 24° C. to about 34° C., from about 24° C. to about 31° C., or from about 24° C. to about 28° C. In one embodiment of the present disclosure, the hydrolysis reaction may be preferably performed at about 25° C.

In one embodiment of the present invention, the hydrolysis reaction may be performed for about 12 hours to about 36 hours, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction is carried out for about 12 hours to about 36 hours, about 12 hours to about 34 hours, about 12 hours to about 32 hours, about 12 hours to about 30 hours, about 12 hours to about 28 hours, about 12 hours to about 26 hours, about 14 hours to about 36 hours, about 14 hours to about 34 hours, about 14 hours to about 32 hours, about 14 hours to about 30 hours, about 14 hours to about 28 hours, about 14 hours to about 26 hours, about 16 hours to about 36 hours, about 16 hours to about 34 hours, about 16 hours to about 32 hours, about 16 hours to about 30 hours, about 16 hours to about 28 hours, about 16 hours to about 26 hours, about 18 hours to about 36 hours, about It can be performed for about 18 hours to about 34 hours, about 18 hours to about 32 hours, about 18 hours to about 30 hours, about 18 hours to about 28 hours, about 18 hours to about 26 hours, about 20 hours to about 36 hours, about 20 hours to about 34 hours, about 20 hours to about 32 hours, about 20 hours to about 30 hours, about 20 hours to about 28 hours, about 20 hours to about 26 hours, about 22 hours to about 36 hours, about 22 hours to about 34 hours, about 22 hours to about 32 hours, about 22 hours to about 30 hours, about 22 hours to about 28 hours, or about 22 hours to about 26 hours. In one embodiment of the present invention, when using about 0.5 equivalents of the catalyst, the hydrolysis reaction may be performed for about 12 hours to about 36 hours. In one embodiment of the present invention, when using about 0.5 equivalents of the catalyst, the hydrolysis reaction may be preferably performed for about 24 hours. In one embodiment of the present invention, when using about 1 equivalent of the catalyst, the hydrolysis reaction may be preferably performed for about 12 hours.

In one embodiment of the present invention, it may be performed under solution conditions including a solvent, but may not be limited thereto.

In one embodiment of the present invention, the solvent may be at least one selected from a hydrochloric organic solvent, an aliphatic hydrocarbon solvent, and an aromatic hydrocarbon solvent.

In one embodiment of the present invention, the hydrochloric organic solvent may be at least one selected from carbon tetrachloride, chloroform, dichloromethane, and dichloroethane.

In one embodiment of the present invention, the aliphatic hydrocarbon organic solvent may be at least one selected from n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane.

In one embodiment of the present invention, the aromatic hydrocarbon solvent may be at least one selected from benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, and n-amylnaphthalene.

In one embodiment of the present invention, the solvent may be at least one selected from dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, n-amylnaphthalene, n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane. Here, the toluene may be substituted or unsubstituted and may be selected from toluene, fluorotoluene, 1,2-difluorotoluene, 1,3-difluorotoluene, 1,4-difluorotoluene, trifluorotoluene, 1,2,4-trifluorotoluene, chlorotoluene, 1,2-dichlorotoluene, 1,3-dichlorotoluene, 1,4-dichlorotoluene, 1,2,4-trichlorotoluene, iodotoluene, 1,2-diiodotoluene, 1,3-diiodotoluene, 1,4-diiodotoluene, or 1,2,4-triiodotoluene. Here, the n-hexane may be substituted or unsubstituted and may be selected from n-hexane, 1-chlorohexane, 1-bromohexane, 1-iodohexane, 1,6-dichlorohexane, 1,6-dibromohexane, 1,6-diiodohexane, and 1-hydroxyhexane.

In one embodiment of the present invention, the solvent may be at least one selected from dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. In one embodiment of the present invention, it may be preferable that the solvent is dichloromethane or chloroform.

In one embodiment of the present invention, a crystallization process may be additionally included after the hydrolysis reaction, but may not be limited thereto.

In one embodiment of the present invention, the solvent used in the crystallization process may be at least one selected from an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent, and an alcohol solvent.

In one embodiment of the present invention, the aliphatic hydrocarbon solvent used in the crystallization process may be at least one selected from n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane.

In one embodiment of the present invention, the aromatic hydrocarbon solvent used in the crystallization process may be at least one selected from benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, and n-amylnaphthalene.

In one embodiment of the present invention, the alcohol solvent used in the crystallization process may be at least one selected from methanol, ethanol, iso-propyl alcohol, butanol, and octanol.

In one embodiment of the present invention, the solvent used in the crystallization process may be n-heptane.

In one embodiment of the present invention, it may further include, but is not limited to, performing a concentration process and a filtration process after the hydrolysis reaction. In one embodiment of the present invention, after the hydrolysis reaction, the mono-tert-butyl-esterified saturated hydrocarbon can be obtained as a solid compound using a conventional separation method.

In the embodiment of the present invention, since the hydrolysis reaction is a reaction in which no impurities are generated, a mono-tert-butyl esterified saturated hydrocarbon can be easily separated and obtained.

In one embodiment of the present invention, the purity of the mono-tert-butyl esterified saturated hydrocarbon obtained by the method for producing the mono-tert-butyl esterified saturated hydrocarbon may be about 90% or more, about 95% or more, about 98% or more, or about 99% or more.

In the embodiment of the present invention, the method for producing the mono-tert-butyl esterified saturated hydrocarbon can be applied to a commercial process.

The second aspect of the present invention provides a cyclic method for producing a mono-tert-butyl esterified saturated hydrocarbon, comprising: performing a hydrolysis reaction of a di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 in the presence of a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula ₂ ; and performing the hydrolysis reaction in the presence of the catalyst on a filtrate of the hydrolysis reaction to additionally obtain a mono-tert-butyl esterified saturated hydrocarbon, at least once; wherein the catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl 2 ), zinc iodide (ZnI ₂ ), and hydrates thereof:

[Chemical Formula 1]

;

;

[Chemical formula 2]

;

;

In the above chemical formula 1 and the above chemical formula 2,

n is an integer greater than or equal to 1.

Although detailed descriptions of parts that overlap with the first aspect of the present application have been omitted, the contents described for the first aspect of the present application may be equally applied even if the description is omitted in the second aspect of the present application.

In one embodiment of the present disclosure, n may be an integer from about 4 to about 22, but may not be limited thereto. In one embodiment of the present disclosure, n may be an integer from about 4 to about 22, from about 4 to about 18, from about 4 to about 14, from about 4 to about 10, from about 4 to about 6, from about 8 to about 22, from about 8 to about 18, from about 8 to about 14, from about 8 to about 10, from about 12 to about 22, from about 12 to about 18, from about 12 to about 16, from about 12 to about 14, from about 14 to about 22, from about 14 to about 18, or from about 20 to about 22. In one embodiment of the present disclosure, n may be about 6 to about 18. In one embodiment of the present disclosure, n may be 14. In one embodiment of the present invention, n may be 16.

In one embodiment of the present invention, the hydrolysis reaction may be performed in an environment including a catalyst selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), or zinc iodide (ZnI ₂ ); and water, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction may be performed in an environment including zinc bromide (ZnBr ₂ ) and water.

In one embodiment of the present invention, the hydrolysis reaction may be performed including a hydrate of zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), or zinc iodide (ZnI ₂ ), but may not be limited thereto.

In one embodiment of the present invention, the catalyst may be zinc bromide (ZnBr ₂ ). In one embodiment of the present invention, the catalyst may be a hydrate of zinc bromide (as a non-limiting example, a dihydrate, ZnBr ₂ 2H ₂ O).

In one embodiment of the present invention, the catalyst may be used in an amount of more than about 0.2 equivalents and less than about 1 equivalent, but may not be limited thereto. In one embodiment of the present invention, the catalyst is present in an amount of from about 0.2 equivalents to about 1 equivalent or less, from about 0.2 equivalents to about 0.9 equivalents or less, from about 0.2 equivalents to about 0.8 equivalents or less, from about 0.2 equivalents to about 0.7 equivalents or less, from about 0.2 equivalents to about 0.6 equivalents or less, from about 0.3 equivalents to about 1 equivalent or less, from about 0.3 equivalents to about 0.9 equivalents or less, from about 0.3 equivalents to about 0.8 equivalents or less, from about 0.3 equivalents to about 0.7 equivalents or less, from about 0.3 equivalents to about 0.6 equivalents or less, from about 0.4 equivalents to about 1 equivalent or less, from about 0.4 equivalents to about 0.9 equivalents or less, from about 0.4 equivalents to about 0.8 equivalents or less, from about 0.4 equivalents to about It may be used in an amount of 0.7 equivalents or less, or from about 0.4 equivalents to about 0.6 equivalents or less. In one embodiment of the present invention, it may be preferable that the catalyst is used in an amount of about 0.5 equivalents.

In one embodiment of the present invention, when n is 14, about 100 mg to about 200 mg of zinc bromide may be used based on 1 mmol of the compound represented by the chemical formula 2. In one embodiment of the present invention, when the amount of zinc bromide is increased, the reaction time may be shortened, but all of the di-tert-butyl-ester groups of the compound represented by the chemical formula 1 may be hydrolyzed.

In one embodiment of the present invention, the hydrolysis reaction may be performed at a temperature range of about 0°C to about 40°C, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction is performed at a temperature of about 0°C to about 40°C, about 0°C to about 37°C, about 0°C to about 34°C, about 0°C to about 31°C, about 0°C to about 28°C, about 3°C to about 40°C, about 3°C to about 37°C, about 3°C to about 34°C, about 3°C to about 31°C, about 3°C to about 28°C, about 6°C to about 40°C, about 6°C to about 37°C, about 6°C to about 34°C, about 6°C to about 31°C, about 6°C to about 28°C, about 9°C to about 40°C, about 9°C to about 37°C, about 9°C to about 34°C, about 9°C to about 31°C, about 9°C to about 28°C, about 12°C to about 40°C, about 12°C to about 37°C, about 12°C to about 34°C, about 12°C to about 31°C, about 12°C to about 28°C, about 15°C to about 40°C, about 15°C to about 37°C, about 15°C to about 34°C, about 15°C to about 31°C, about 15°C to about 28°C, about 18°C to about 40°C, about 18°C to about 37°C, about 18°C to about 34°C, about 18°C to about 31°C, about 18°C to about 28°C, about 21°C to about 40°C, about 21°C to about 37°C, about 21°C to about 34°C, about 21°C to about 31°C, about 21°C to about 28°C, about 24°C to about 40°C, about It may be performed at a temperature range of from about 24° C. to about 37° C., from about 24° C. to about 34° C., from about 24° C. to about 31° C., or from about 24° C. to about 28° C. In one embodiment of the present disclosure, the hydrolysis reaction may be preferably performed at about 25° C.

In one embodiment of the present invention, the hydrolysis reaction may be performed for about 12 hours to about 36 hours, but may not be limited thereto. In one embodiment of the present invention, the hydrolysis reaction is carried out for about 12 hours to about 36 hours, about 12 hours to about 34 hours, about 12 hours to about 32 hours, about 12 hours to about 30 hours, about 12 hours to about 28 hours, about 12 hours to about 26 hours, about 14 hours to about 36 hours, about 14 hours to about 34 hours, about 14 hours to about 32 hours, about 14 hours to about 30 hours, about 14 hours to about 28 hours, about 14 hours to about 26 hours, about 16 hours to about 36 hours, about 16 hours to about 34 hours, about 16 hours to about 32 hours, about 16 hours to about 30 hours, about 16 hours to about 28 hours, about 16 hours to about 26 hours, about 18 hours to about 36 hours, about It can be performed for about 18 hours to about 34 hours, about 18 hours to about 32 hours, about 18 hours to about 30 hours, about 18 hours to about 28 hours, about 18 hours to about 26 hours, about 20 hours to about 36 hours, about 20 hours to about 34 hours, about 20 hours to about 32 hours, about 20 hours to about 30 hours, about 20 hours to about 28 hours, about 20 hours to about 26 hours, about 22 hours to about 36 hours, about 22 hours to about 34 hours, about 22 hours to about 32 hours, about 22 hours to about 30 hours, about 22 hours to about 28 hours, or about 22 hours to about 26 hours. In one embodiment of the present invention, when using about 0.5 equivalents of the catalyst, the hydrolysis reaction may be performed for about 12 hours to about 36 hours. In one embodiment of the present invention, when using about 0.5 equivalents of the catalyst, the hydrolysis reaction may be preferably performed for about 24 hours. In one embodiment of the present invention, when using about 1 equivalent of the catalyst, the hydrolysis reaction may be preferably performed for about 12 hours.

In one embodiment of the present invention, it may be performed under solution conditions including a solvent, but may not be limited thereto.

In one embodiment of the present invention, the solvent may be at least one selected from a hydrochloric organic solvent, an aliphatic hydrocarbon solvent, and an aromatic hydrocarbon solvent.

In one embodiment of the present invention, the hydrochloric organic solvent may be at least one selected from carbon tetrachloride, chloroform, dichloromethane, and dichloroethane.

In one embodiment of the present invention, the aliphatic hydrocarbon organic solvent may be at least one selected from n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane.

In one embodiment of the present invention, the aromatic hydrocarbon solvent may be at least one selected from benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, and n-amylnaphthalene.

In one embodiment of the present invention, the solvent may be at least one selected from dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, n-amylnaphthalene, n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane. Here, the toluene may be substituted or unsubstituted and may be selected from toluene, fluorotoluene, 1,2-difluorotoluene, 1,3-difluorotoluene, 1,4-difluorotoluene, trifluorotoluene, 1,2,4-trifluorotoluene, chlorotoluene, 1,2-dichlorotoluene, 1,3-dichlorotoluene, 1,4-dichlorotoluene, 1,2,4-trichlorotoluene, iodotoluene, 1,2-diiodotoluene, 1,3-diiodotoluene, 1,4-diiodotoluene, or 1,2,4-triiodotoluene. Here, the n-hexane may be substituted or unsubstituted and may be selected from n-hexane, 1-chlorohexane, 1-bromohexane, 1-iodohexane, 1,6-dichlorohexane, 1,6-dibromohexane, 1,6-diiodohexane, and 1-hydroxyhexane.

In one embodiment of the present invention, the solvent may be at least one selected from dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. In one embodiment of the present invention, it may be preferable that the solvent is dichloromethane or chloroform.

In one embodiment of the present invention, it may further include, but is not limited to, performing a crystallization process after the hydrolysis reaction.

In one embodiment of the present invention, the solvent used in the crystallization process may be at least one selected from an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent, and an alcohol solvent.

In one embodiment of the present invention, the aliphatic hydrocarbon solvent used in the crystallization process may be at least one selected from n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane.

In one embodiment of the present invention, the aromatic hydrocarbon solvent used in the crystallization process may be at least one selected from benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, and n-amylnaphthalene.

In one embodiment of the present invention, the alcohol solvent used in the crystallization process may be at least one selected from methanol, ethanol, iso-propyl alcohol, butanol, and octanol.

In one embodiment of the present invention, the solvent used in the crystallization process may be n-heptane.

In one embodiment of the present invention, it may further include, but is not limited to, performing a concentration process and a filtration process after the hydrolysis reaction. In one embodiment of the present invention, after the hydrolysis reaction, the mono-tert-butyl-esterified saturated hydrocarbon can be obtained as a solid compound using a conventional separation method.

In the embodiment of the present invention, since the hydrolysis reaction is a reaction in which no impurities are generated, a mono-tert-butyl esterified saturated hydrocarbon can be easily separated and obtained.

In one embodiment of the present invention, the purity of the mono-tert-butyl esterified saturated hydrocarbon obtained by the cyclic production method of the mono-tert-butyl esterified saturated hydrocarbon may be about 90% or more, about 95% or more, about 98% or more, or about 99% or more.

In the embodiment of the present invention, the cyclic production method of the mono-tert-butyl esterified saturated hydrocarbon can be applied to a commercial process.

In an embodiment of the present invention, the cumulative crystallization yield of the mono-tert-butyl esterified saturated hydrocarbon obtained by the cyclical production method of the mono-tert-butyl esterified saturated hydrocarbon may be about 40% or more, about 50% or more, about 60% or more, about 65% or more, about 70% or more, about 75% or more, about 80% or more, about 85% or more, or about 90% or more.

Hereinafter, the present invention will be described in more detail using examples. However, the following examples are provided only to help understand the present invention, and the contents of the present invention are not limited to the following examples.

[Example]

<Production of mono-tert-butyl esterified saturated hydrocarbons>

1. Selection of solvent

To select an appropriate solvent for the hydrolysis reaction of di-tert-butyl-octadecandioate, the reaction was carried out using dichloromethane, chloroform, dimethylformaldehyde, toluene, tetrahydrofuran, acetone, ethyl acetate, and n-hexane, respectively, as solvents.

1 mmol of di-tert-butyl-octadecanedioic acid and 0.5 mmol of zinc bromide (ZnBr ₂ ) were each added to the above solvent and stirred at room temperature for 24 hours to obtain octadecanedioic acid mono-tert-butyl ester. The conversion and purity of the octadecanedioic acid mono-tert-butyl ester were measured through high performance liquid chromatography (HPLC) analysis and are shown in Table 1 below. The conversions shown in Tables 1 to 5 below were calculated by the following calculation formula 1:

[Calculation formula 1]

Conversion rate (%) =

In the above calculation formula 1, the conversion rate represents the HPLC area at the end of the reaction.

menstruum Conversion rate (%) Purity (%) of octadecanedioic acid-mono-tert-butyl ester Example 1-1 Dichloromethane
(dichloromethane) 48 99.5 Example 1-2 chloroform
(chloroform) 43 99.4 Example 1-3 toluene
(toluene) 39 98.3 Example 1-4 Normal hexane
(n-hexane) 26 96.2 Comparative Example 1-1 N,N-Dimethylformaldehyde
(N,N-dimethylformaldehyde) 0 - Comparative Example 1-2 Tetrahydrofuran
(tetrahydrofuran) 0 - Comparative Example 1-3 Acetone
(acetone) 0 - Comparative Example 1-4 Ethyl acetate
(ethyl acetate) 0 -

Referring to Table 1 above, Comparative Examples 1-1 to 1-4 were unsuitable as reaction solvents because hydrolysis into octadecanedioic acid-mono-tert-butyl ester did not occur. On the other hand, Examples 1-1 and 1-2 showed a high conversion rate of about 40% or more compared to Comparative Examples 1-1 to 1-4, and it was confirmed that products with a purity of about 99% or more were obtained, thereby confirming their suitability as solvents. In Examples 1-3 and 1-4, although the hydrolysis reaction proceeded, the respective conversion rates were 39% and 26%, which were lower values than Examples 1-1 and 1-2. Accordingly, it was confirmed that chloride-based organic solvents, aromatic hydrocarbon-based solvents, and aliphatic hydrocarbon-based solvents are suitable as solvents for hydrolysis reactions, while ketone-based solvents, amide-based solvents, ester-based solvents, and ether-based solvents are unsuitable.

2. Selection of catalyst

In order to select a suitable catalyst for the hydrolysis reaction of 1 mmol of di-tert-butyl-octadecanedioate, 0.5 mol of zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), zinc iodide (ZnI ₂ ), and zinc bromide dihydrate (ZnBr ₂ 2H ₂ O) were each added, and the reaction was performed at room temperature for 12 to 24 hours to obtain octadecanedioic acid-mono-tert-butyl ester, and the conversion and yield at this time were as follows. Here, the yield was calculated by the following calculation formula 2:

[Calculation formula 2]

In the above calculation formula 2, the yield represents the actual mass% of octadecanedioic acid-mono-tert-butyl-ester obtained through the post-treatment process after the reaction is completed.

Catalyst type Conversion rate
(%) Chemical Purity of Octadecane Dioic Acid Mono-Tert-Butyl Ester (%) Reaction time
(hr) transference number
(%) Example 2-1 Zinc Bromide
(ZnBr ₂ ) 48 99.5 24 45 Example 2-2 Zinc chloride
(ZnCl ₂ ) 46 99.3 14 44 Example 2-3 Zinc iodide
(ZnI ₂ ) 44 98.9 16 42 Example 2-4 zinc bromide dihydrate
(ZnBr _2· 2H ₂ O) 42 99.1 6 40

Referring to Table 2 above, Examples 2-2, 2-3, and 2-4 showed relatively fast reactions compared to Example 2-1; however, in Example 2-3, the solution discolored during the reaction, and the product obtained was not decolorized. Examples 2-2 and 2-4 had relatively fast reaction rates, and if the analysis time during the reaction is long, a lot of by-products are generated, so the process risk is high compared to Example 2-1. The conversion rate, yield, and purity of the product obtained in Example 2-1 were 48%, 45%, and 99.5%, respectively, confirming that the zinc bromide of Example 2-1 was the most suitable catalyst for the hydrolysis reaction.

3. Selection of ZnBr ₂ usage amount and reaction time

In order to select the appropriate amount of ZnBr ₂ and reaction time for the hydrolysis reaction of 1 mmol of di-tert-butyl-octadecanedioate, the reaction was performed by controlling each condition differently.

Here, ZnBr ₂ was used in amounts of 0.2 mmol, 0.5 mmol, and 1.0 mmol, respectively, and the reaction was carried out for 12 hours, 24 hours, and 36 hours, respectively, for each amount of ZnBr ₂ . The reaction temperature was 25°C, and 3.1 mL of dichloromethane was used as a solvent. After the reaction, the obtained octadecanedioic acid-mono-tert-butyl ester was analyzed by HPLC to measure the conversion rate and purity, which are shown in Table 3 below:

Zinc Bromide
(mmol, equivalent) Reaction time
(hr) Conversion rate
(%) Chemical Purity of Octadecane Dioic Acid Mono-Tert-Butyl Ester (%) transference number (%) Example 3-1 0.5 12 34 99.4 30 Example 3-2 0.5 24 48 99.5 45 Example 3-3 0.5 36 35 92.5 28 Example 3-4 1.0 12 27 91.0 22 Comparative Example 3-1 0.2 12 12 95.0% or more 10 Comparative Example 3-2 0.2 24 17 95.0% or more 13 Comparative Example 3-3 0.2 36 20 95.0% or more 15 Comparative Example 3-4 1.0 24 9 80.0% or less 5 Comparative Example 3-5 1.0 36 N/D - -

Referring to Table 3 above, Examples 3-1 to 3-4 all showed a purity of 90% or higher, and among these, Example 3-2 showed the best hydrolysis activity with a conversion rate of 48% and a purity of 99.5%, whereas Comparative Examples 3-1 to 3-5 showed very low conversion rates of 20% or less. Accordingly, it was experimentally confirmed that the appropriate amount and reaction time of ZnBr ₂ used in the hydrolysis reaction were 0.5 equivalents and 24 hours, respectively.

When using the same amount of catalyst in the above hydrolysis reaction, if the reaction time becomes excessively long, both esters included in the reactant, di-tert-butyl-octadecanedioate, are decomposed, lowering the yield and purity of the desired product. Therefore, it is very important to use an appropriate equivalent amount of catalyst.

4. Preparation of mono-tert-butyl-esterified long-chain hydrocarbon carboxylic acids

1 mmol of compounds represented by the following chemical formula 1 and having n values of 12 to 16 were each hydrolyzed for 24 hours in the presence of a ZnBr ₂ catalyst to obtain mono-tert-butyl-esterified long-chain hydrocarbon carboxylic acids represented by the following chemical formula 2 and having n values of 12 to 16. The conversion, chemical purity of the desired product, and yield for each hydrolysis reaction are shown in Table 4 below:

[Chemical Formula 1]

;

;

[Chemical formula 2]

.

.

n Conversion rate
(%) Chemical purity of target product (%) transference number
(%) Example 4-1 12 47 99.4 42 Example 4-2 13 46 99.3 43 Example 4-3 14 48 99.5 45 Example 4-4 15 47 99.6 44 Example 4-5 16 46 99.5 45

The method for producing octadecanedioic acid-mono-tert-butyl ester obtained in the above Example 4-3 and represented by the following chemical formula 3 is as follows:

[Chemical Formula 3]

;

;

100 g of di-tert-butyl-octadecanedioate (0.234 mol) and 26.3 g of ZnBr ₂ (0.117 mol, 0.5 equivalents) were added to 1,000 mL of dichloromethane and stirred at 25°C for 24 hours to perform a hydrolysis reaction. After confirming the completion of the reaction through HPLC, 500 mL of purified water was added and stirred for 1 hour. Thereafter, the layers were separated to remove the aqueous solution layer, and 20 g of anhydrous sodium sulfate was added to the organic layer, dehydrated, and filtered. The filtrate was concentrated under reduced pressure, and n-heptane was added and stirred for 1 hour to obtain a crystal, which was then cooled to 10°C and filtered. Afterwards, after washing with n-heptane and drying under reduced pressure at 40°C, 39.1 g of white octadecanedioic acid-mono-tert-butyl ester (0.105 mol and chemical purity 99.5%) was obtained.

<Cyclic production of mono-tert-butyl esterified saturated hydrocarbons>

5. Recovery process of hydrolysis reaction residue

After concentrating the filtrate of Example 4-3, the HPLC analysis result showed that the ratio of the starting material (di-tert-butyl-octadecanedioate) of the hydrolysis reaction and the target product (octadecanedioic acid-mono-tert-butyl ester) in the filtrate was measured to be 95:5. The mass of the filtrate was measured to be 55 g, and accordingly, the mass of the starting material contained in the filtrate was confirmed to be 52.3 g (0.123 mol). 13.8 g of ZnBr ₂ (0.061 mol) corresponding to 0.5 equivalents and 523 mL of dichloromethane were added to the filtrate, and the mixture was stirred at 25°C for 24 hours to perform a recovery reaction. After confirming the completion of the above recovery reaction by HPLC, a crystallization process was performed to additionally obtain 20 g of octadecanedioic acid-mono-tert-butyl ester (0.054 mol and chemical purity 99.6%) (Example 5-1).

Thereafter, the hydrolysis reaction was performed on the filtrate of Example 5-1 in the same manner as in Example 4-3 to additionally obtain the target product (Example 5-2). The hydrolysis reaction was performed in the same manner on the filtrate of Example 5-2 (Example 5-3), and the hydrolysis reaction was performed in the same manner on the filtrate of Example 5-3 (Example 5-4). As described above, a recovery process of repeatedly performing the same hydrolysis reaction on the filtrate generated after each hydrolysis reaction was performed, and a total of four recovery processes were performed on the filtrate of Example 4-3. The yields and purities of Example 4-3 and Examples 5-1 to 5-4 are as shown in Table 5 below:

The remainder
Number of recoveries Crystallization yield
(At each recovery stage
Cumulative yield including target product) Purity of target product (%) Example 4-3 0 45% (45%) 99.5 Example 5-1 1 23% (68%) 99.6 Example 5-2 2 14% (82%) 99.5 Example 5-3 3 7% (89%) 99.4 Example 5-4 4 3% (92%) 99.5

Since the hydrolysis reaction above did not generate by-products and thus had a high purity, recovery of the filtrate was easy, and referring to Table 5 above, the crystallization yield increased from 45% to 92% as the recovery process was performed four times for the filtrate of Example 4-3. The crystallization yield, average chemical purity range, and NMR analysis results of the products obtained after performing the recovery process four times for each of the compounds prepared from Examples 4-1, 4-2, 4-3, 4-4, and 4-5 are shown in Table 6 below:

[Chemical Formula 1]

;

;

[Chemical formula 2]

;

;

n product
(CAS No.) transference number (%) Average chemical purity
Range (%) ¹ H-NMR (CDCl ₃ ) Example
6-1 12 16-(tert-butoxy)-16-oxohexadecanoic acid
(CAS No. 843666-27-3) 89 99.3% to 99.9% D 1.25(m, 20 H); 1.44(s, 8 H); 1.59(m, 4H), 2.27(m, 4H) Example
6-2 13 17-(tert-butoxy)-17-oxoheptadecanoic acid
(CAS No. 905302-44-5) 90 99.3% to 99.9% D 1.25(m, 22 H); 1.44(s, 9 H); 1.59(m, 4H), 2.27(m, 4H) Example
6-3 14 18-(tert-butoxy)-18-oxooctadecanoic acid
(CAS No. 843666-40-0) 92 99.3% to 99.9% D 1.25(m, 24 H); 1.44(s, 9 H); 1.59(m, 4H), 2.27(m, 4H) Example
6-4 15 19-(tert-butoxy)-19-oxononadecanoic acid
(CAS No.1643852-37-2) 90 99.3% to 99.9% D 1.25(m, 26 H); 1.44(s, 9 H); 1.59(m, 4H), 2.27(m, 4H) Example
6-5 16 20-(tert-butoxy)-20-oxoicosanoic acid
(CAS No. 683239-16-9) 91 99.3% to 99.9% D 1.25(m, 28 H); 1.44(s, 9 H); 1.59(m, 4H), 2.27(m, 4H)

The above description of the present invention is for illustrative purposes only, and those skilled in the art will understand that the present invention can be easily modified into other specific forms without changing the technical idea or essential features of the present invention. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive. For example, each component described as a single component may be implemented in a distributed manner, and likewise, components described as distributed may be implemented in a combined manner.

Claims (25)

A method comprising: subjecting a di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 to a hydrolysis reaction under a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 2; The above catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), zinc iodide (ZnI ₂ ), and hydrates thereof. Process for producing mono-tert-butyl esterified saturated hydrocarbons: [Chemical Formula 1]

; [Chemical formula 2]

; In the above chemical formula 1 and the above chemical formula 2, n is an integer greater than or equal to 1. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein n is an integer from 4 to 22. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above n is 14. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above n is 16. In paragraph 1, A method for producing a mono-tert-butyl-esterified saturated hydrocarbon, wherein the catalyst is zinc bromide (ZnBr ₂ ) or a hydrate thereof. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the catalyst is used in an amount of more than 0.2 equivalents and less than or equal to 1 equivalent. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the catalyst is used in an amount of 0.4 to 0.6 equivalents. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above hydrolysis reaction is performed at a temperature range of 0°C to 40°C. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above hydrolysis reaction is performed at a temperature range of 20°C to 30°C. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above hydrolysis reaction is performed for 12 to 36 hours. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above hydrolysis reaction is performed under solution conditions containing a solvent. In Article 11, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent is at least one selected from a hydrochloric organic solvent, an aliphatic hydrocarbon solvent, and an aromatic hydrocarbon solvent. In Article 11, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent is at least one selected from dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, n-amylnaphthalene, n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane. In Article 11, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent is at least one selected from dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. In paragraph 1, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, further comprising a crystallization process after the above hydrolysis reaction. In Article 15, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent used in the above crystallization process is at least one selected from an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent, and an alcohol solvent. In Article 15, A method for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent used in the above crystallization process is n-heptane. A di-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 1 is hydrolyzed in the presence of a catalyst to obtain a mono-tert-butyl esterified saturated hydrocarbon represented by the following chemical formula 2, It includes performing the hydrolysis reaction on the residue of the above hydrolysis reaction under the above catalyst at least once to additionally obtain a mono-tert-butyl esterified saturated hydrocarbon, The above catalyst is at least one selected from zinc bromide (ZnBr ₂ ), zinc chloride (ZnCl ₂ ), zinc iodide (ZnI ₂ ), and hydrates thereof. Cyclic process for the production of mono-tert-butyl esterified saturated hydrocarbons: [Chemical Formula 1]

; [Chemical formula 2]

; In the above chemical formula 1 and the above chemical formula 2, n is an integer greater than or equal to 1. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein n is 14. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein n is 16. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the catalyst is zinc bromide (ZnBr ₂ ) or a hydrate thereof. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the catalyst is used in an amount of 0.4 to 0.6 equivalents. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the hydrolysis reaction is performed at a temperature range of 20°C to 30°C. In Article 18, A cyclic process for producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the above hydrolysis reaction is performed for 12 to 36 hours. In Article 18, A method for cyclically producing a mono-tert-butyl esterified saturated hydrocarbon, wherein the solvent used in the above hydrolysis reaction is at least one selected from dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, iso-propylbenzene, diethylbenzene, iso-butylbenzene, triethylbenzene, di-iso-propylbenzene, n-amylnaphthalene, n-pentane, iso-pentane, n-hexane, iso-hexane, n-heptane, iso-heptane, 2,2,4-trimethylpentane, n-octane, iso-octane, cyclohexane, and methylcyclohexane.

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