KR101518308B1 - Method for manufacturing high-purity vegetable fatty alcohol - Google Patents
Method for manufacturing high-purity vegetable fatty alcohol Download PDFInfo
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- KR101518308B1 KR101518308B1 KR1020130020035A KR20130020035A KR101518308B1 KR 101518308 B1 KR101518308 B1 KR 101518308B1 KR 1020130020035 A KR1020130020035 A KR 1020130020035A KR 20130020035 A KR20130020035 A KR 20130020035A KR 101518308 B1 KR101518308 B1 KR 101518308B1
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- C07—ORGANIC CHEMISTRY
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
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Abstract
본 발명은 이소스테아린산으로부터 이소스테아릴알코올을 제조하는 방법으로, (A) 탄소수 16 또는 18의 포화지방산의 혼합물을 지방산메틸에스테르화하는 단계; (B) (A)단계에서 수득된 지방산메틸에스테르 혼합물을 0 ~ 30℃로 냉각하여 이소스테아린산메틸에스테르를 분리하는 단계; 및 (C) 상기 (B)단계에서 분리된 이소스테아린산메틸에스테르를 수소화 공정을 거쳐 이소스테아릴알코올로 제조하는 단계;를 포함하는 것을 특징으로 하는 고순도의 이소스테아릴알코올의 제조방법을 개시한다. The present invention relates to a process for preparing isostearyl alcohol from isostearic acid, comprising the steps of: (A) subjecting a mixture of saturated fatty acids having 16 or 18 carbon atoms to fatty acid methyl esterification; (B) isolating the isostearic acid methyl ester by cooling the fatty acid methyl ester mixture obtained in step (A) to 0 to 30 占 폚; And (C) preparing isostearyl alcohol by hydrogenating the isostearic acid methyl ester isolated in the step (B) to prepare isostearyl alcohol.
Description
본 발명은 안정성이 뛰어난 식물성 지방산 알코올의 제조방법에 관한 것으로, 다단계 분리공정을 거치지 않고 단순한 공정으로 고순도의 식물성 지방산 알코올을 제조하는 방법에 관한 것이다.
The present invention relates to a method for producing a vegetable fatty acid alcohol having excellent stability and a method for producing a vegetable fatty acid alcohol having a high purity by a simple process without a multistage separation process.
고급지방산이란 탄소수 6 이상의 지방족 카르복실산으로, 그 종류에는 포화지방산과 불포화지방산이 있다. 각종 유지에 함유되어 있으며 비누·계면활성제·금속비누 등의 합성원료로 사용된다. 고급 알코올이란, 분자에 함유되어 있는 탄소수가 6 이상인 지방족 알코올을 의미하는 것으로, 천연유지를 원료로 하는 것와 석유화학에서 합성한 것으로 나눌 수 있다. 탄소수가 증가함에 따라 또는 포화도가 높아짐에 따라 유상(油狀)에서 고체로 된다. 물에는 거의 녹지 않으며 중성이다. 탄소수 6 ∼ 12의 것은 용제 및 가소제, 12 ∼ 16의 것은 세제나 계면활성제(界面活性劑), 16 이상의 것은 화장품·의약품 등에 주로 사용된다. 예를 들면, 화장품에서의 고급알코올의 사용은 크림 및 로션류의 경도나 점도를 조절하고 유화를 완정화하기 위해 사용된다.Higher fatty acids are aliphatic carboxylic acids having 6 or more carbon atoms, and there are saturated fatty acids and unsaturated fatty acids. It is contained in various kinds of oils and is used as a raw material for synthesis of soap, surfactant, metal soap and the like. The term "higher alcohol" means an aliphatic alcohol having 6 or more carbon atoms contained in a molecule, and can be divided into a mixture of natural fat as a raw material and petroleum chemistry. As the carbon number increases or as the degree of saturation increases, it becomes solid from oil. It is almost insoluble in water and neutral. Solvents and plasticizers having 6 to 12 carbon atoms, detergents and surfactants (surfactants) having 12 to 16, and cosmetic and pharmaceutical products having 16 or more are mainly used. For example, the use of higher alcohols in cosmetics is used to control the hardness and viscosity of creams and lotions and to stabilize emulsions.
한편, 이소스테아린산(isostearic acid)은 지방산을 원료로 하여 고온고압하에서 다단계의 분리 정제 과정을 통하여 제조된다. 이렇게 다단계를 통하여 제조된 혼합 이소스테아린산은 고순도를 요하며 이소스테아린산 자체로 사용되기 보다는 이소스테아릴알코올로 제조되어 사용되는 것이 일반적이며, 주요한 용도로는 화장품, 윤활제, 솔벤트, 금속처리제 등에 사용된다.On the other hand, isostearic acid is produced by a multi-stage separation and purification process under high temperature and high pressure using fatty acid as a raw material. Mixed isostearic acid produced through such a multistage process requires high purity. It is generally used in isostearyl alcohol rather than isostearic acid itself, and is mainly used for cosmetics, lubricants, solvents, and metal treating agents.
[이소스테아린산의 구조식의 일예][Example of structural formula of isostearic acid]
한편, 이소스테아릴알코올(isostearyl alcohol, C18H38O)은 탄소 18개의 분지형 지방족 알코올의 혼합물이다. On the other hand, isostearyl alcohol (C 18 H 38 O) is a mixture of 18 branched aliphatic alcohols.
[이소스테아릴알코올의 구조식의 일예][Example of Structural Formula of Isostearyl Alcohol]
이소스테아릴알코올은 앞서 언급한 바와 같이 이소스테아린산으로부터 합성되는데, 고온고압하에서 다단계의 분리 정제 과정을 거친 후 알코올로 합성하게 되는 것이다. 그런데, 이소스테아린산의 고온고압 합성시에는 이소스테아린산이 약 20 ~ 50% 정도 합성되고 그 외에 스테아린산과 팔미틴산이 함유하게 된다. 따라서 고순도의 이소스테아린산을 제조하기 위해서는 이소스테아린산과 함께 함유되어 있는 스테아린산, 팔미틴산 등을 분리하여야 하는데, 이때 융점을 이용한 저온분리기술을 이용하거나, 비점을 이용한 분별 증류법을 이용하여 이소스테아린산을 고순도화하는 것이 일반적이다. 하지만, 이소스테아린산과 팔미틴, 스테아린산의 융점의 차이는 약 30℃, 비점의 경우 15 ~ 20℃에 불과하여, 일단계 분리과정으로 분리하기에는 매우 어려울 뿐만 아니라 이소스테아린산의 순도를 높이는 것이 매우 어려운 실정이다. Isostearyl alcohol is synthesized from isostearic acid as described above, which is subjected to a multi-stage separation and purification process under high temperature and high pressure and then synthesized with alcohol. When isostearic acid is synthesized at high temperature and high pressure, about 20 to 50% of isostearic acid is synthesized. In addition, stearic acid and palmitic acid are contained. Therefore, in order to produce high purity isostearic acid, stearic acid, palmitic acid, and the like, which are contained together with isostearic acid, must be separated. At this time, by using a low temperature separation technique using a melting point or by fractionation using boiling point, isostearic acid is highly purified It is common. However, the difference in melting point between isostearic acid, palmitic acid and stearic acid is only about 30 ° C and the boiling point is only 15 to 20 ° C, which is very difficult to separate by a one-step separation process, and it is very difficult to increase the purity of isostearic acid .
그런데, 이소스테아릴알코올은 열 안정성과 산화 안정성이 매우 우수하여 화장품 등의 원료에 다양하게 사용될 있는바, 고순도의 이소스테아릴알코올을 쉽게 얻을 수 있는 기술의 개발이 강력하게 요구되고 있는 실정이다. However, since isostearyl alcohol has excellent thermal stability and oxidation stability, it is widely used in raw materials for cosmetics and the like, and thus it is strongly desired to develop a technique for easily obtaining high purity isostearyl alcohol.
한편, 고급 알코올의 제조기술로는 대한민국 공개특허 제1020040024279호(화분으로부터 고급알콜을 제조하는 방법), 대한민국 공개특허 제1019940014281호(거의직쇄인고급1급알콜의제조방법), 대한민국 공개특허 제1019960022417호(고급알콜의제조방법) 등이 있다. 하지만, 아직까지 고순도의 이소스테아릴알코올을 다단계 분리 공정을 거치지 않고 단순한 공정으로 얻기 위한 기술은 전혀 알려지지 않은 실정이다.
On the other hand, Korean Patent Laid-Open Publication No. 1020040024279 (a method for producing a higher alcohol from a flowerpot), Korean Patent Publication No. 1019940014281 (a method for producing a substantially linear high-grade alcohol), Korean Patent Publication No. 1019960022417 (A method for producing higher alcohols). However, the technology for obtaining a high purity isostearyl alcohol by a simple process without a multistage separation process is not yet known.
본 발명은 기존의 다단 분리 고순도화 공정을 거치지 않고도 매우 간단히 고순도의 이소스테아릴알코올을 수득하는 방법을 제공하는 것을 목적으로 한다.
It is an object of the present invention to provide a method for obtaining isostearyl alcohol of high purity in a very simple manner without going through a conventional multi-stage separation high purification process.
상기 목적을 달성하기 위하여, 본 발명은 이소스테아린산으로부터 이소스테아릴알코올을 제조하는 방법으로, (A) 탄소수 16 또는 18의 포화지방산의 혼합물을 지방산메틸에스테르화하는 단계; (B) (A)단계에서 수득된 지방산메틸에스테르 혼합물을 0 ~ 30℃로 냉각하여 이소스테아린산메틸에스테르를 분리하는 단계; 및 (C) 상기 (B)단계에서 분리된 이소스테아린산메틸에스테르를 수소화 공정을 거쳐 이소스테아릴알코올로 제조하는 단계;를 포함하는 것을 특징으로 하는 고순도의 이소스테아릴알코올의 제조방법을 제공한다.
In order to achieve the above object, the present invention provides a method for producing isostearyl alcohol from isostearic acid, comprising the steps of (A) subjecting a mixture of saturated fatty acids having 16 or 18 carbon atoms to fatty acid methyl esterification; (B) isolating the isostearic acid methyl ester by cooling the fatty acid methyl ester mixture obtained in step (A) to 0 to 30 占 폚; And (C) preparing isostearyl alcohol by hydrogenating the isostearic acid methyl ester isolated in the step (B). The present invention also provides a process for preparing isostearyl alcohol having high purity.
이하에서는, 본 발명의 고순도의 이소스테아릴알코올의 제조방법을 각 단계별로 자세히 설명하겠다.
Hereinafter, the method for producing high purity isostearyl alcohol of the present invention will be described in detail in each step.
(A) 탄소수 16 또는 18의 포화지방산의 혼합물을 지방산메틸에스테르화하는 단계(A) a step of fatty acid methyl esterification of a mixture of saturated fatty acids having 16 or 18 carbon atoms
본 발명은 이소스테아린산으로부터 고순도의 이소스테아릴알코올을 제조하기 위하여, 탄소수 16 또는 18의 포화지방산의 혼합물을 지방산메틸에스테르화하는 것을 특징으로 한다. The present invention is characterized by a fatty acid methyl esterification of a mixture of saturated fatty acids having 16 or 18 carbon atoms in order to produce isostearyl alcohol of high purity from isostearic acid.
본 발명의 이소스테아릴알코올은 이소스테아린산으로부터 제조되는데, 지방산으로부터 수득된 이소스테아린산은 일반적으로 스테아린산과 팔미트산이 혼합되어 있다. 그런데, 이소스테아린산과 스테아린산, 팔미틴산은 융점의 차이가 약 30℃, 비점의 차이는 약 15 ~ 20℃에 불과하여 일단계로 이소스테아린산을 분리해내는 것은 매우 어렵다. 이에 본 발명은 지방산으로부터 수득된 이소스테아린산, 스테아린산 또는 팔미트산의 혼합물을 지방산메틸에스테르화하는데, 이러한 지방산의 메틸에스테르화를 통하여 융점의 차이를 현격하게 나게 할 수 있다. 구체적으로, 스테아린산메틸에스테르와 팔미틴산메틸에스테르의 융점은 약 30 ~ 40℃ 정도인데 반하여, 이소스테아린산메틸에스테르의 경우는 약 -50 ~ -10℃로써 융점의 차이가 대략 40 ~ 90℃ 정도나 되어 저온 분리법으로 쉽게 이소스테아린산메틸에스테르를 분리해낼 수 있게 된다.The isostearyl alcohol of the present invention is prepared from isostearic acid. Isostearic acid obtained from fatty acids is generally a mixture of stearic acid and palmitic acid. However, isostearic acid, stearic acid and palmitic acid are difficult to separate isostearic acid in one step because the difference in melting point is about 30 ° C and the difference in boiling point is only about 15 to 20 ° C. Accordingly, the present invention provides a fatty acid methyl esterification of a mixture of isostearic acid, stearic acid or palmitic acid obtained from a fatty acid. The methyl esterification of such a fatty acid makes the difference in melting point remarkable. Specifically, the melting point of stearic acid methyl ester and palmitic acid methyl ester is about 30 to 40 ° C., whereas in the case of isostearic acid methyl ester, the melting point difference is about 40 to 90 ° C. at about -50 to -10 ° C., Separation can easily separate the methyl ester of isostearic acid.
이때, 바람직하게는 탄소수 16 또는 18의 포화지방산의 혼합물에 촉매로 황산 또는 황화백금(Platinum sulfide, PtS)를 첨가한 후, 과량의 메탄올(20 ~ 30%)을 첨가하여 150 ~ 180℃에서 1 ~ 3시간 동안 반응을 수행하여 지방산메틸에스테르화함으로써, 지방산메틸에스테르의 혼합물을 얻을 수 있다. At this time, sulfuric acid or platinum sulfide (PtS) is preferably added as a catalyst to a mixture of saturated fatty acids having 16 or 18 carbon atoms, and excess methanol (20 to 30%) is added. The reaction is carried out for ~ 3 hours to give a fatty acid methyl esterification, whereby a mixture of fatty acid methyl esters can be obtained.
여기서, 상기 탄소수 16 또는 18의 포화지방산의 혼합물은 이소스테아린산, 스테아린산 또는 팔미트산의 혼합물이며, 바람직하게는 올레인산 또는 대두지방산을 이성화반응시킨 후, 수소화 반응을 거쳐 수득된 것이 좋다. 예를 들면, 올레인산을 150 ~ 250℃에서 3 ~ 20kgf/cm2의 압력으로 촉매로써 백토를 1 ~ 10% 첨가하여 올레인산을 분지지방산으로 전환한다. 이 전환 과정에서 생긴 부산물은 증류기를 통하여 제거하여 지방산의 함량을 높인다. 이렇게 해서 얻어진 지방산에 수소를 첨가하고 백금 또는 팔라디움을 촉매로 첨가하여 약 100 ~ 250℃에서 5 ~ 20kgf/cm2의 압력으로 30분에서 3시간 동안 반응하여 지방산 중에 함유된 이중결합을 단일결합으로 전환시켜 불포화지방산을 포화지방산으로 전환시킨다. 이렇게 전환되어 얻어진 포화지방산은 이소스테아린산, 스테아린산 또는 팔미트산의 혼합물이다. 따라서 이를 지방산메틸에스테르화하면 이소스테아린산메틸에스테르, 스테아린산메틸에스테르, 팔미트산메틸에스테르를 얻을 수 있다.
Here, the mixture of saturated fatty acids having 16 or 18 carbon atoms is a mixture of isostearic acid, stearic acid or palmitic acid, preferably oleic acid or soybean fatty acid isomerized and hydrogenated. For example, oleic acid is converted into branched fatty acids by adding 1 to 10% of clay with a catalyst at a pressure of 3 to 20 kgf / cm 2 at 150 to 250 ° C. By-products from this conversion process are removed through a distiller to increase the fatty acid content. Hydrogen is added to the fatty acid thus obtained, and platinum or palladium is added as a catalyst, and the reaction is carried out at a temperature of about 100 to 250 ° C at a pressure of 5 to 20 kgf / cm 2 for 30 minutes to 3 hours to form a double bond contained in the fatty acid as a single bond Conversion of unsaturated fatty acids to saturated fatty acids. The saturated fatty acid thus obtained is a mixture of isostearic acid, stearic acid or palmitic acid. Thus, when it is converted into fatty acid methyl ester, isostearic acid methyl ester, stearic acid methyl ester and palmitic acid methyl ester can be obtained.
(B) (A)단계에서 수득된 지방산메틸에스테르 혼합물을 0 ~ 30℃로 냉각하여 이소스테아린산메틸에스테르를 분리하는 단계(B) separating the methyl ester of isostearic acid by cooling the fatty acid methyl ester mixture obtained in the step (A) to 0 to 30 DEG C,
본 단계는 상기 수득된 지방산메틸에스테르 혼합물을 0 ~ 30℃로 냉각하여 저온분리법으로 이소스테아린산메틸에스테르를 분리해내는 것이다. In this step, the obtained fatty acid methyl ester mixture is cooled to 0 to 30 DEG C and the isostearic acid methyl ester is separated by low temperature separation.
앞서 설명한 바와 같이, 스테아린산메틸에스테르와 팔미틴산메틸에스테르의 융점은 약 30 ~ 40℃ 정도인데 반하여, 이소스테아린산메틸에스테르의 경우는 약 -50 ~ -10℃로써 융점의 차이가 대략 40 ~ 90℃ 정도나 되므로, 본 발명은 이소스테아린산메틸에스테르, 스테아린산메틸에스테르, 팔미트산메틸에스테르의 혼합물을 0 ~ 30℃로 냉각하여 스테아린산메틸에스테르와 팔미트산메틸에스테르를 완전히 제거함으로써, 이소스테아린산메틸에스테르를 일단계로 쉽게 분리해낼 수 있다.
As described above, the melting point of stearic acid methyl ester and palmitic acid methyl ester is about 30 to 40 DEG C, whereas the isostearic acid methyl ester has a melting point of about -50 to -10 DEG C and the difference in melting point is about 40 to 90 DEG C Thus, the present invention is a process for producing isostearic acid by cooling a mixture of isostearic acid methyl ester, stearic acid methyl ester and palmitic acid methyl ester to 0 to 30 DEG C to completely remove stearic acid methyl ester and palmitic acid methyl ester, Can be easily separated.
(C) 상기 (B)단계에서 분리된 이소스테아린산메틸에스테르를 수소화 공정을 거쳐 이소스테아릴알코올로 제조하는 단계(C) preparing isostearic acid methyl ester from the step (B) through isomerization with isostearyl alcohol through hydrogenation
본 단계는 상기 분리된 이소스테아린산메틸에스테르를 수소화 공정을 거쳐 이소스테아릴알코올로 제조하는 것이다. In this step, the isolated methyl isostearate is hydrogenated to prepare isostearyl alcohol.
이때, 촉매를 이용한 수소화반응을 시키는 것이 바람직하며, 예를 들면, 상기 분리된 고순도의 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180 ~ 250℃에서 수소를 투입하여 50 ~ 200kgf/cm²의 압력으로 수소화를 시킴으로써, 이소스테아릴알코올을 얻을 수 있다.
At this time, it is preferable to carry out a hydrogenation reaction using a catalyst. For example, hydrogen is introduced at 180 to 250 ° C using Cr 2 O 3 as a catalyst in the separated high-purity isostearic acid methyl ester, Isostearyl alcohol can be obtained.
본 발명은 상기 단계를 거침으로써, 고순도의 이소스테아릴알코올을 다단계의 분리공정을 거치지 않고도 쉽게 제조할 수 있으며, 이와 같이 수득된 이소스테아릴알코올은 열안정성과 산화안정성이 매우 우수하여 화장품, 윤활제 등의 원료로 다양하게 사용될 수 있다.
The isostearyl alcohol of the present invention can be easily produced without going through a multi-step separation step by passing the above step, and the isostearyl alcohol thus obtained is excellent in thermal stability and oxidation stability, And the like.
본 발명은 고순도의 이소스테아릴알코올을 다단계의 분리공정을 거치지 않고도 매우 쉽게 제조할 수 있으며, 이와 같이 수득된 이소스테아릴알코올은 열안정성과 산화안정성이 매우 우수하여 화장품, 윤활제 등의 원료로 다양하게 사용될 수 있다.
The present invention can very easily produce isostearyl alcohol having a high purity without going through a multistage separation step. The isostearyl alcohol thus obtained is excellent in thermal stability and oxidation stability and can be used as a raw material for cosmetics and lubricants Lt; / RTI >
이하, 본 발명의 구성을 하기 실시예를 통해 구체적으로 설명하지만, 본 발명의 권리범위가 하기 실시예에만 한정되는 것은 아니고 이와 등가의 기술적 사상의 변형까지를 포함한다.
Hereinafter, the structure of the present invention will be described in detail with reference to the following examples, but the scope of the present invention is not limited to the following examples, but includes modifications of equivalent technical ideas.
실시예Example 1 : 고순도 이소스테아릴 알코올의 제조 1: Preparation of high purity isostearyl alcohol
올레인산 100g에 촉매로 백토 10g 첨가하고 150℃에서 20kgf/cm²의 압력으로 7시간 동안 반응시켜 올레인산을 분지지방산(branched fatty acid)으로 전환하였다. 이 전환 과정에서 생긴 부산물은 증류기를 통하여 제거하고 지방산의 함량을 높였다. 이렇게 해서 얻어진 지방산 30g에 수소를 첨가하고 촉매로 백금 3g 첨가하여 200℃에서 20kgf/cm²의 압력으로 2시간 동안 반응하여 지방산 중에 함유된 이중결합을 단일결합으로 전환시켜 불포화지방산을 포화지방산으로 전환하였다. 이렇게 경화반응을 거친 포화지방산에는 팔미틴산, 스테아린산, 아이소스테아린산이 혼합되어 있다. 이들 포화지방산에 100℃에서 촉매로 황산 2g 첨가하고, 메탄올 50g을 첨가하여 150℃에서 1시간 동안 반응시켜 지방산메틸에스테르를 얻었다. 이렇게 얻어진 혼합 지방산메틸에스테르를 20℃로 냉각하여 팔미틴산메틸에스테르와 스테아린산메틸에스테를 완전히 제거하고, 고순도의 이소스테아린산메틸에스테르 20g을 얻었다. 이러한 고순도의 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180~ 250℃에서 수소를 투입하여 50 ~ 200kgf/cm²의 압력으로 수소화를 시켜서 이소스테아릴알코올을 얻게 되었다. 10 g of white clay was added as a catalyst to 100 g of oleic acid, and the mixture was reacted at 150 ° C. under a pressure of 20 kgf / cm 2 for 7 hours to convert oleic acid to branched fatty acid. By-products from this conversion process were removed through the distiller and the fatty acid content was increased. Hydrogen was added to 30 g of the fatty acid thus obtained, 3 g of platinum was added as a catalyst, and the resulting mixture was reacted at 200 ° C. under a pressure of 20 kgf / cm 2 for 2 hours to convert the double bond contained in the fatty acid into a single bond to convert the unsaturated fatty acid into a saturated fatty acid . Saturated fatty acids that have undergone this curing reaction are mixed with palmitic acid, stearic acid, and isostearic acid. To these saturated fatty acids, 2 g of sulfuric acid was added as a catalyst at 100 ° C., and 50 g of methanol was added and reacted at 150 ° C. for 1 hour to obtain a fatty acid methyl ester. The mixed fatty acid methyl ester thus obtained was cooled to 20 DEG C to completely remove the palmitic acid methyl ester and the stearic acid methyl ester, and 20 g of high purity isostearic acid methyl ester was obtained. Hydrogen was introduced at such a high purity isostearic acid methyl ester as Cr 2 O 3 as a catalyst at 180 to 250 ° C. and hydrogenated at a pressure of 50 to 200 kgf / cm 2 to obtain isostearyl alcohol.
얻어진 이소스테아릴알코올은 탄소수 18, 수산기가 210, 융점 -25℃이다.
The isostearyl alcohol thus obtained has a carbon number of 18, a hydroxyl value of 210, and a melting point of -25 캜.
실시예 2 : 고순도 이소스테아릴 알코올의 제조Example 2: Preparation of high purity isostearyl alcohol
올레인산 100g에 촉매로 백토 10g 첨가하고 200℃에서 20kgf/cm²의 압력으로 7시간 동안 반응시켜 올레인산을 분지지방산(branched fatty acid)으로 전환하였다. 이 전환 과정에서 생긴 부산물은 증류기를 통하여 제거하고 지방산의 함량을 높였다. 이렇게 해서 얻어진 지방산 30g에 수소를 첨가하고 촉매로 팔라디움 3g 첨가하여 200℃에서 20kgf/cm²의 압력으로 2시간 동안 반응하여 지방산 중에 함유된 이중결합을 단일결합으로 전환시켜 불포화지방산을 포화지방산으로 전환하였다. 이렇게 경화반응을 거친 포화지방산에는 팔미틴산, 스테아린산, 아이소스테아린산이 혼합되어 있다. 이들 포화지방산에 100℃에서 촉매로 PtS 2g 첨가하고, 메탄올 50g을 첨가하여 150℃에서 1시간 동안 반응시켜 지방산메틸에스테르를 얻었다. 이렇게 얻어진 혼합 지방산메틸에스테르를 20℃로 냉각하여 팔미틴산메틸에스테르와 스테아린산메틸에스테를 완전히 제거하고, 고순도의 이소스테아린산메틸에스테르 20g을 얻었다. 이러한 고순도의 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180~ 250℃에서 수소를 투입하여 50 ~ 100kgf/cm²의 압력으로 수소화를 시켜서 이소스테아릴알코올을 얻게 되었다. 10 g of white clay as a catalyst was added to 100 g of oleic acid, and the resulting mixture was reacted at 200 ° C. under a pressure of 20 kgf / cm 2 for 7 hours to convert oleic acid to branched fatty acid. By-products from this conversion process were removed through the distiller and the fatty acid content was increased. Hydrogen was added to 30 g of the fatty acid thus obtained, 3 g of palladium was added as a catalyst, and the resulting mixture was reacted at 200 DEG C under a pressure of 20 kgf / cm < 2 > for 2 hours to convert the double bond contained in the fatty acid into a single bond to convert the unsaturated fatty acid into a saturated fatty acid . Saturated fatty acids that have undergone this curing reaction are mixed with palmitic acid, stearic acid, and isostearic acid. To these saturated fatty acids, 2 g of PtS was added as a catalyst at 100 DEG C, and 50 g of methanol was added and reacted at 150 DEG C for 1 hour to obtain fatty acid methyl esters. The mixed fatty acid methyl ester thus obtained was cooled to 20 DEG C to completely remove the palmitic acid methyl ester and the stearic acid methyl ester, and 20 g of high purity isostearic acid methyl ester was obtained. Hydrogen was introduced at such a high purity isostearic acid methyl ester as Cr 2 O 3 as a catalyst at 180 to 250 ° C. and hydrogenated at a pressure of 50 to 100 kgf / cm 2 to obtain isostearyl alcohol.
얻어진 이소스테아릴알코올은 탄소수 18, 수산기가 210, 융점 -23℃이다.
The obtained isostearyl alcohol had 18 carbon atoms, 210 hydroxyl groups, and a melting point of -23 캜.
실시예 3 : 고순도 이소스테아릴 알코올의 제조Example 3: Preparation of high purity isostearyl alcohol
대두지방산 100g에 촉매로 백토 10g 첨가하고 150℃에서 20kgf/cm²의 압력으로 7시간 동안 반응시켜 올레인산을 분지지방산(branched fatty acid)으로 전환하였다. 이 전환 과정에서 생긴 부산물은 증류기를 통하여 제거하고 지방산의 함량을 높였다. 이렇게 해서 얻어진 지방산 50g에 수소를 첨가하고 촉매로 백금 5g 첨가하여 200℃에서 20kgf/cm²의 압력으로 2시간 동안 반응하여 지방산 중에 함유된 이중결합을 단일결합으로 전환시켜 불포화지방산을 포화지방산으로 전환하였다. 이렇게 경화반응을 거친 포화지방산에는 팔미틴산, 스테아린산, 아이소스테아린산이 혼합되어 있다. 이들 포화지방산에 100℃에서 촉매로 황산 2g 첨가하고, 메탄올 50g을 첨가하여 150℃에서 1시간 동안 반응시켜 지방산메틸에스테르를 얻었다. 이렇게 얻어진 혼합 지방산메틸에스테르를 20℃로 냉각하여 팔미틴산메틸에스테르와 스테아린산메틸에스테를 완전히 제거하고, 고순도의 이소스테아린산메틸에스테르 10g을 얻었다. 이러한 고순도의 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180~ 250℃에서 수소를 투입하여 50 ~ 100kgf/cm²의 압력으로 수소화를 시켜서 이소스테아릴알코올을 얻게 되었다. 10 g of white clay was added as a catalyst to 100 g of soybean fatty acid, and oleic acid was converted to branched fatty acid by reaction at 150 ° C. under a pressure of 20 kgf / cm 2 for 7 hours. By-products from this conversion process were removed through the distiller and the fatty acid content was increased. Hydrogen was added to 50 g of the fatty acid thus obtained, and 5 g of platinum was added as a catalyst. The resulting mixture was reacted at 200 ° C. under a pressure of 20 kgf / cm 2 for 2 hours to convert the double bond contained in the fatty acid into a single bond to convert the unsaturated fatty acid into a saturated fatty acid . Saturated fatty acids that have undergone this curing reaction are mixed with palmitic acid, stearic acid, and isostearic acid. To these saturated fatty acids, 2 g of sulfuric acid was added as a catalyst at 100 ° C., and 50 g of methanol was added and reacted at 150 ° C. for 1 hour to obtain a fatty acid methyl ester. The mixed fatty acid methyl ester thus obtained was cooled to 20 DEG C to completely remove the palmitic acid methyl ester and stearic acid methyl ester, and 10 g of high purity isostearic acid methyl ester was obtained. Hydrogen was introduced at such a high purity isostearic acid methyl ester as Cr 2 O 3 as a catalyst at 180 to 250 ° C. and hydrogenated at a pressure of 50 to 100 kgf / cm 2 to obtain isostearyl alcohol.
얻어진 이소스테아릴알코올은 탄소수 18, 수산기가 210, 융점 -20℃이다.
The isostearyl alcohol thus obtained had a carbon number of 18, a hydroxyl value of 210, and a melting point of -20 캜.
실시예 4 : 고순도 이소스테아릴 알코올의 제조Example 4: Preparation of high purity isostearyl alcohol
대두지방산 100g에 촉매로 백토 10g 첨가하고 200℃에서 20kgf/cm²의 압력으로 7시간 동안 반응시켜 올레인산을 분지지방산(branched fatty acid)으로 전환하였다. 이 전환 과정에서 생긴 부산물은 증류기를 통하여 제거하고 지방산의 함량을 높였다. 이렇게 해서 얻어진 지방산 50g에 수소를 첨가하고 촉매로 팔라디움 5g 첨가하여 200℃에서 20kgf/cm²의 압력으로 2시간 동안 반응하여 지방산 중에 함유된 이중결합을 단일결합으로 전환시켜 불포화지방산을 포화지방산으로 전환하였다. 이렇게 경화반응을 거친 포화지방산에는 팔미틴산, 스테아린산, 아이소스테아린산이 혼합되어 있다. 이들 포화지방산에 100℃에서 촉매로 PtS 2g 첨가하고, 메탄올 50g을 첨가하여 150℃에서 1시간 동안 반응시켜 지방산메틸에스테르를 얻었다. 이렇게 얻어진 혼합 지방산메틸에스테르를 20℃로 냉각하여 팔미틴산메틸에스테르와 스테아린산메틸에스테를 완전히 제거하고, 고순도의 이소스테아린산메틸에스테르 10g을 얻었다. 이러한 고순도의 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180~ 250℃에서 수소를 투입하여 50 ~ 200kgf/cm²의 압력으로 수소화를 시켜서 이소스테아릴알코올을 얻게 되었다. 10 g of white clay was added as a catalyst to 100 g of soybean fatty acid, and the reaction was carried out at 200 ° C. under a pressure of 20 kgf / cm 2 for 7 hours to convert oleic acid to branched fatty acid. By-products from this conversion process were removed through the distiller and the fatty acid content was increased. Hydrogen was added to 50 g of the thus-obtained fatty acid, and 5 g of palladium was added as a catalyst. The resulting mixture was reacted at 200 ° C. under a pressure of 20 kgf / cm 2 for 2 hours to convert the double bond contained in the fatty acid into a single bond to convert the unsaturated fatty acid into a saturated fatty acid . Saturated fatty acids that have undergone this curing reaction are mixed with palmitic acid, stearic acid, and isostearic acid. To these saturated fatty acids, 2 g of PtS was added as a catalyst at 100 DEG C, and 50 g of methanol was added and reacted at 150 DEG C for 1 hour to obtain fatty acid methyl esters. The mixed fatty acid methyl ester thus obtained was cooled to 20 DEG C to completely remove the palmitic acid methyl ester and stearic acid methyl ester, and 10 g of high purity isostearic acid methyl ester was obtained. Hydrogen was introduced at such a high purity isostearic acid methyl ester as Cr 2 O 3 as a catalyst at 180 to 250 ° C. and hydrogenated at a pressure of 50 to 200 kgf / cm 2 to obtain isostearyl alcohol.
얻어진 이소스테아릴알코올은 탄소수 18, 수산기가 215, 융점 -15℃이다.The isostearyl alcohol thus obtained had a carbon number of 18, a hydroxyl value of 215, and a melting point of -15 캜.
Claims (5)
(A) 탄소수 16 또는 18의 포화지방산의 혼합물을 지방산메틸에스테르화하는 단계;
(B) (A)단계에서 수득된 지방산메틸에스테르 혼합물을 0 ~ 30℃로 냉각하여 이소스테아린산메틸에스테르를 분리하는 단계; 및
(C) (B)단계에서 분리된 이소스테아린산메틸에스테르를 수소화 공정을 거쳐 이소스테아릴알코올로 제조하는 단계;를 포함하고,
(C)단계는,
상기 이소스테아린산메틸에스테르에 촉매로 Cr2O3를 사용하여 180 ~ 250℃에서 수소를 투입하여 50 ~ 200kgf/cm²의 압력으로 수소화시키는 것을 특징을 하는 이소스테아릴알코올의 제조방법.
As a method for producing isostearyl alcohol from isostearic acid,
(A) fatty acid methyl esterification of a mixture of saturated fatty acids having 16 or 18 carbon atoms;
(B) isolating the isostearic acid methyl ester by cooling the fatty acid methyl ester mixture obtained in step (A) to 0 to 30 占 폚; And
(C) preparing isostearic acid methyl ester isolated in step (B) from isostearyl alcohol through a hydrogenation process,
(C)
Wherein the isostearic acid methyl ester is hydrogenated using Cr 2 O 3 as a catalyst at 180 to 250 ° C. under a pressure of 50 to 200 kgf / cm 2.
상기 (A)단계에서,
탄소수 16 또는 18의 포화지방산의 혼합물은 이소스테아린산, 스테아린산 또는 팔미트산의 혼합물인 것을 특징으로 하는 이소스테아릴알코올의 제조방법.
The method according to claim 1,
In the step (A)
Wherein the mixture of saturated fatty acids having 16 or 18 carbon atoms is a mixture of isostearic acid, stearic acid or palmitic acid.
상기 (A)단계에서,
탄소수 16 또는 18의 포화지방산의 혼합물은,
올레인산 또는 대두지방산을 이성화반응시킨 후, 수소화 반응을 거쳐 수득된 것을 특징으로 하는 이소스테아릴알코올의 제조방법.
The method according to claim 1,
In the step (A)
A mixture of saturated fatty acids having 16 or 18 carbon atoms,
A process for producing isostearyl alcohol characterized by being obtained by subjecting an oleic acid or a soybean fatty acid to an isomerization reaction followed by hydrogenation.
상기 (A)단계에서,
탄소수 16 또는 18의 포화지방산의 혼합물에, 촉매로 황산 또는 황화백금(Platinum sulfide, PtS)의 존재하에 메탄올을 첨가하여 150 ~ 180℃에서 1 ~ 3시간 동안 반응을 수행하는 것을 특징으로 하는 이소스테아릴알코올의 제조방법.The method according to claim 1,
In the step (A)
Characterized in that methanol is added to a mixture of saturated fatty acids having 16 or 18 carbon atoms in the presence of sulfuric acid or platinum sulfide (PtS) as a catalyst and the reaction is carried out at 150 to 180 ° C for 1 to 3 hours. A method for producing an aryl alcohol.
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