KR101620925B1 - Process for preparing 1,2-hexanediol - Google Patents
Process for preparing 1,2-hexanediol Download PDFInfo
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- KR101620925B1 KR101620925B1 KR1020140048717A KR20140048717A KR101620925B1 KR 101620925 B1 KR101620925 B1 KR 101620925B1 KR 1020140048717 A KR1020140048717 A KR 1020140048717A KR 20140048717 A KR20140048717 A KR 20140048717A KR 101620925 B1 KR101620925 B1 KR 101620925B1
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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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C29/94—Use of additives, e.g. for stabilisation
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- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
Abstract
본 발명은 산화제로서 과산화수소 및 촉매로서 특정 철염을 사용하여, 고순도의 1,2-헥산다이올을 높은 수율로 제조하는 방법을 제공한다.The present invention provides a method for producing high purity 1,2-hexanediol in high yield by using hydrogen peroxide as an oxidizing agent and a specific iron salt as a catalyst.
Description
본 발명은 1,2-헥산다이올의 제조방법에 관한 것으로, 더욱 상세하게는 1-헥센을 특정 산화제 및 촉매와 반응시키는 것을 포함하는 1,2-헥산다이올의 제조방법에 관한 것이다.The present invention relates to a process for the preparation of 1,2-hexanediol, and more particularly to a process for preparing 1,2-hexanediol comprising reacting 1-hexene with a specific oxidizing agent and catalyst.
1,2-헥산다이올은 우수한 보습작용과 향균작용을 가지고 있어 방부제의 대체품으로 유용하게 사용되고 있다. 화장품 업계에서는 통상적으로 메틸파라벤, 프로필파라벤 등의 방부제가 사용되고 있으나, 이들은 유해 화학물질로 등재되어 사용이 규제되고 있다. 예를 들어, 한국 특허공개 제2005-41745호는 1,2-헥산다이올을 포함하는 화장료를 개시하고 있다. 상기 1,2-헥산다이올은 하기 화학식 1의 구조식을 갖는다.1,2-Hexanediol has excellent moisturizing and antibacterial activity and is useful as a substitute for preservatives. Preservatives such as methylparaben and propylparaben are commonly used in the cosmetics industry, but they are listed as hazardous chemicals and their use is regulated. For example, Korean Patent Publication No. 2005-41745 discloses a cosmetic comprising 1,2-hexanediol. The 1,2-hexanediol has the following structural formula.
<화학식 1>≪ Formula 1 >
1,2-헥산다이올은 1-헥센의 이중결합을 산화제로 산화시킴으로써 제조할 수 있다. 예를 들어, Tetrahedron Letters (2006), 47, (30), 5285-5288 혹은 J. Org. Chem, Vol. 69, No. 13, 2004 4381-4389에 개시된 산화반응을 응용하여 제조할 수 있다. 그러나, 상기 논문에 개시된 산화반응을 이용한 제조방법은 고가의 산화제를 사용하여야 하므로 산업적인 생산에 적용하기가 곤란하다. 또한, 상대적으로 저가의 산화제를 이용하여 1-헥센의 이중결합을 산화시킬 경우에는 1,2-헥산다이올이 매우 낮은 수율로 얻어지게 된다. 1,2-Hexanediol can be prepared by oxidizing the double bond of 1-hexene with an oxidizing agent. For example, Tetrahedron Letters (2006), 47, (30), 5285-5288 or J. Org. Chem., Vol. 69, No. 13, 2004, 4381-4389. However, since the production method using the oxidation reaction disclosed in the above-mentioned paper requires the use of an expensive oxidizing agent, it is difficult to apply it to industrial production. Further, when a double bond of 1-hexene is oxidized using a relatively inexpensive oxidizing agent, 1,2-hexanediol can be obtained in a very low yield.
또한, 1,2-헥산다이올은 제조과정에서 함유되는 불순물에 의해 특유의 냄새를 가지고 있는 문제가 있다. 따라서, 화장품 등의 원료로서 사용하기 위하여는, 합성된 1,2-헥산다이올을 고순도로 정제하거나, 별도의 탈취공정을 수행하여야 하며, 이는 제조비용을 상승시키는 원인이 된다.Further, 1,2-hexanediol has a problem that it has a characteristic odor due to the impurities contained in the manufacturing process. Therefore, for use as a raw material for cosmetics and the like, the synthesized 1,2-hexanediol must be purified with high purity or a separate deodorization step, which causes a rise in manufacturing cost.
이와 같은 제조방법의 한계로 인하여, 1,2-헥산다이올의 대량 생산이 곤란하며, 현재 국외에서 무색 무취의 고순도 1,2-헥산다이올을 고가로 수입하여 사용하고 있는 실정이다 (예를 들면 Ube Industries. Ltd. 의 제품명 KMO-6).Due to the limitations of such a production method, it is difficult to mass-produce 1,2-hexanediol, and at present, colorless odorless high-purity 1,2-hexanediol is imported at high prices and used (Product name KMO-6 from Ube Industries. Ltd.).
본 발명자들은 무색 무취의 고순도 1,2-헥산다이올을 높은 수율로 제조할 수 있는 방법을 개발하고자 다양한 연구를 수행하였다. 놀랍게도, 본 발명자들 저가의 산화제인 과산화수소를 사용하고, 특정 철염을 촉매로서 사용하여 1-헥센의 산화반응을 수행하였을 때, 고순도의 1,2-헥산다이올을 높은 수율로 제조할 수 있다는 것을 발견하였다. 특히, 이와 같이 얻어진 1,2-헥산다이올은 간단한 증류를 통하여 고순도로 단리됨으로써, 별도의 탈취공정 및/또는 정제공정을 수행할 필요가 없다는 것을 발견하였다.The present inventors have conducted various studies in order to develop a method for producing colorless odorless high-purity 1,2-hexanediol in high yield. Surprisingly, it has been found that high purity 1,2-hexanediol can be produced in a high yield when hydrogen peroxide, which is a low-cost oxidizing agent, is used and the oxidation reaction of 1-hexene is carried out using a specific iron salt as a catalyst Respectively. In particular, it has been found that 1,2-hexanediol thus obtained is isolated at a high purity through simple distillation, so that there is no need to carry out a separate deodorization process and / or purification process.
따라서, 본 발명은 산화제로서 과산화수소 및 촉매로서 특정 철염을 사용하여, 고순도의 1,2-헥산다이올을 높은 수율로 제조하는 방법을 제공하는 것을 목적으로 한다.Accordingly, it is an object of the present invention to provide a method for producing 1,2-hexanediol of high purity at a high yield by using hydrogen peroxide as an oxidizing agent and a specific iron salt as a catalyst.
본 발명의 일 태양에 따라, 1-헥센을 과산화수소 및 3가철 염과 반응시키는 것을 포함하는, 1,2-헥산다이올의 제조방법이 제공된다.According to one aspect of the present invention, there is provided a process for preparing a 1,2-hexane diol comprising reacting 1-hexene with hydrogen peroxide and a trivalent salt.
본 발명의 제조방법에 있어서, 상기 3가철 염(ferric salt)은 염화 철(Iron(II) chloride) 또는 이의 수화물 혹은 파라톨루엔설폰산 철(Iron(III) p-toluenesulfonate) 또는 이의 수화물일 수 있다. 상기 3가철염은 1-헥센 1 당량에 대하여 0.02 ∼ 0.05 당량의 비율로 사용될 수 있다. 또한, 상기 과산화수소는 1-헥센 1 당량에 대하여 1.5 ∼ 1.8 당량의 비율로 사용될 수 있다. 또한, 상기 반응은 30 ∼ 40 ℃에서 수행될 수 있다. In the preparation method of the present invention, the ferric salt may be iron (II) chloride or a hydrate thereof or iron (III) p-toluenesulfonate or a hydrate thereof . The trivalent salt may be used in a proportion of 0.02 to 0.05 equivalent based on 1 equivalent of 1-hexene. The hydrogen peroxide may be used in a proportion of 1.5 to 1.8 equivalents based on 1 equivalent of 1-hexene. In addition, the reaction can be carried out at 30 to 40 ° C.
일 구현예에서, 본 발명의 제조방법은 상기 1-헥센과 과산화수소과의 반응 혼합물에 상기 3가철 염을 가하여 반응시킴으로써 수행된다. In one embodiment, the process of the invention is carried out by reacting the trivalent salt with a reaction mixture of 1-hexene and hydrogen peroxide.
다른 구현예에서, 본 발명의 제조방법은 용매로서 포름산 존재하에서 수행된다.In another embodiment, the process of the present invention is carried out in the presence of formic acid as a solvent.
저가의 산화제인 과산화수소를 사용하고, 특정 철염(즉, 3가철 염)을 촉매로서 사용하여 1-헥센의 산화반응을 수행할 경우, 고순도의 1,2-헥산다이올을 96% 이상의 높은 수율로 제조할 수 있다는 것이 본 발명에 의해 밝혀졌다. 특히, 본 발명의 제조방법에 따라 얻어지는 1,2-헥산다이올은 간단한 증류를 통하여 고순도(99.7% 또는 99.8%의 HPLC 순도)로 단리됨으로써, 별도의 탈취공정 및/또는 정제공정을 수행할 필요가 없다는 것이 본 발명에 의해 밝혀졌다. 따라서, 본 발명에 따른 제조방법은 산업적 규모의 대량생산, 예를 들어 1 뱃치당 500 kg 이상의 산업적 규모의 대량생산에 유용하게 적용될 수 있다.When the oxidation reaction of 1-hexene is carried out using hydrogen peroxide as a low-cost oxidizing agent and a specific iron salt (i.e. trivalent salt) as a catalyst, 1,2-hexanediol having a high purity is obtained at a yield of 96% It can be produced by the present invention. In particular, the 1,2-hexanediol obtained according to the production process of the present invention is isolated by high purity (99.7% or 99.8% HPLC purity) through simple distillation, so that a separate deodorization process and / It was found by the present invention. Therefore, the manufacturing method according to the present invention can be advantageously applied to mass production on an industrial scale, for example, mass production on an industrial scale of 500 kg or more per batch.
본 발명은 1-헥센을 과산화수소 및 3가철 염과 반응시키는 것을 포함하는, 1,2-헥산다이올의 제조방법을 제공한다.The present invention provides a process for preparing a 1,2-hexanediol comprising reacting 1-hexene with hydrogen peroxide and a trivalent salt.
본 발명의 제조방법에 사용되는 1-헥센은 하기 화학식 2의 구조를 가지며, 상업적으로 구입가능하다. The 1-hexene used in the production process of the present invention has a structure represented by the following formula (2) and is commercially available.
<화학식 2>(2)
본 발명의 제조방법은 저가의 산화제인 과산화수소를 이용하여 수행되며, 따라서 제조비용을 최소화할 수 있다. 상기 과산화수소는 출발물질인 1-헥센에 대하여 과량으로 사용되는 것이 바람직하다. 예를 들어, 상기 과산화수소는 1-헥센 1 당량에 대하여 1.5 ∼ 1.8 당량의 비율로 사용될 수 있다.The production process of the present invention is carried out using hydrogen peroxide, which is a low-cost oxidizing agent, and thus the manufacturing cost can be minimized. The hydrogen peroxide is preferably used in an excess amount relative to the starting material, 1-hexene. For example, the hydrogen peroxide may be used in a ratio of 1.5 to 1.8 equivalents based on 1 equivalent of 1-hexene.
본 발명의 제조방법은 통상의 유기용매 중에서 수행될 수 있으며, 바람직하게는 포름산을 사용하여 수행될 수 있다.The production process of the present invention can be carried out in a conventional organic solvent, preferably using formic acid.
상기 3가철 염(ferric salt)은 3가철(Fe3 +)을 함유하는 무기염 또는 유기염을 포함하며, 또한 이들의 수화물을 포함한다. 예를 들어, 상기 3가철 염은 염화 철(Iron(II) chloride) 또는 이의 수화물(예를 들어, 6수화물) 혹은 파라톨루엔설폰산 철(Iron(III) p-toluenesulfonate) 또는 이의 수화물(예를 들어, 6수화물)일 수 있다. 상기 3가철 염은 1-헥센 1 당량에 대하여 0.02 ∼ 0.05 당량의 비율로 사용될 수 있다. 바람직하게는, 염화 철 또는 이의 수화물은 1-헥센 1 당량에 대하여 약 0.05 당량의 비율로 사용될 수 있다. 또한, 바람직하게는, 파라톨루엔설폰산 철은 1-헥센 1 당량에 대하여 약 0.02 당량의 비율로 사용될 수 있다. The 3 gacheol salt (ferric salt) and 3 gacheol is an inorganic salt or an organic salt containing the (Fe + 3), also comprises the hydrates thereof. For example, the trivalent salt may be prepared from iron (II) chloride or a hydrate thereof (e.g., hexahydrate) or iron (III) p-toluenesulfonate or a hydrate thereof For example, hexahydrate). The trivalent salt may be used in a proportion of 0.02 to 0.05 equivalent based on 1 equivalent of 1-hexene. Preferably, iron chloride or its hydrate can be used in a ratio of about 0.05 equivalents to 1 equivalent of 1-hexene. Also, preferably, iron para-toluenesulfonate can be used in a proportion of about 0.02 equivalent based on 1 equivalent of 1-hexene.
상기한 바와 같이, 촉매로서 3가철 염의 존재하에서 1-헥센의 산화반응을 수행할 경우, 촉매를 사용하지 않은 경우에 비하여, 낮은 온도에서 반응을 수행할 수 있을 뿐만 아니라, 용매의 사용량을 크게 낮출 수 있으며, 특유의 향이 나는 부산물의 생성을 최소화할 수 있다. 즉, 촉매 비존재하에서 반응을 수행할 경우 50∼80℃의 온도로의 가온이 필요하다. 그러나, 본 발명에서와 같이 촉매로서 3가철 염의 존재하에서 반응을 수행할 경우, 반응의 활성화 에너지를 낮춰 30∼40℃의 온도에서도 반응을 수행할 수 있다. 따라서, 일 구현예에서, 본 발명의 제조방법은 30 ∼ 40 ℃에서 수행된다. As described above, when the oxidation reaction of 1-hexene is carried out in the presence of a trivalent salt as a catalyst, the reaction can be performed at a lower temperature as compared with the case where a catalyst is not used, And can minimize the production of unique scented by-products. That is, when the reaction is carried out in the absence of a catalyst, heating to a temperature of 50 to 80 ° C is required. However, when the reaction is carried out in the presence of a trivalent salt as a catalyst as in the present invention, the reaction can be carried out at a temperature of 30 to 40 캜 by lowering the activation energy of the reaction. Thus, in one embodiment, the preparation method of the present invention is carried out at 30 to 40 占 폚.
또한, 본 발명에서와 같이 촉매로서 3가철 염의 존재하에서 반응을 수행할 경우, 용매(예를 들어, 포름산)의 사용량을 약 절반으로 줄일 수 있고 또한 특유의 향이 나는 부산물의 생성을 최소화할 수 있다. 용매의 사용량 감소는 반응 장치의 부식 가능성이 줄일 수 있을 뿐만 아니라, 폐수 처리과정에서 사용되는 중화제의 양도 줄일 수 있으므로, 산업적 규모의 대량생산에 적합하다. In addition, when the reaction is carried out in the presence of a trivalent iron salt as a catalyst as in the present invention, the amount of the solvent (for example, formic acid) can be reduced to about half and the production of unique fragrant by-products can be minimized . Decreasing the amount of solvent used not only reduces the possibility of corrosion of the reactor, but also reduces the amount of neutralizing agent used in the wastewater treatment process, making it suitable for mass production on an industrial scale.
일 구현예에서, 본 발명의 제조방법은 상기 1-헥센과 과산화수소과의 반응 혼합물에 상기 3가철염을 가하여 반응시킴으로써 수행된다. In one embodiment, the process of the invention is carried out by reacting the trivalent salt with a reaction mixture of 1-hexene and hydrogen peroxide.
이하, 본 발명을 실시예를 통하여 더욱 상세히 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명이 하기 실시예에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to examples. However, the following examples are for the purpose of illustrating the present invention and the present invention is not limited by the following examples.
실시예 1.Example 1.
1-헥센(5g, 0.0594mole) 및 30% 과산화수소수(10.7mL, 1.5eq.)를 포름산(65mL)에 가하였다. 상기 반응 혼합물을 30℃에서 교반하면서, 파라톨루엔설폰산 철 6수화물(0.8g, 0.02eq.)을 물(5ml)에 용해시킨 용액을 적가하였다. 상기 반응 혼합물을 4시간 동안 교반한 후, 증류하여 1,2-헥산다이올 6.81g을 수득하였다. (수율: 97%, GC 순도: 99.8%)1-Hexene (5 g, 0.0594 mole) and 30% aqueous hydrogen peroxide (10.7 mL, 1.5 eq.) Were added to formic acid (65 mL). A solution of iron paratoluenesulfonate hexahydrate (0.8 g, 0.02 eq.) In water (5 ml) was added dropwise while stirring the reaction mixture at 30 占 폚. The reaction mixture was stirred for 4 hours and then distilled to obtain 6.81 g of 1,2-hexanediol. (Yield: 97%, GC purity: 99.8%).
실시예 2.Example 2.
1-헥센(5g, 0.0594mole) 및 30% 과산화수소수(10.7mL, 1.5eq.)를 포름산(65mL)에 가하였다. 상기 반응 혼합물을 30℃에서 교반하면서, 염화 철(0.48g 0.05eq.)을 물(5ml)에 용해시킨 용액을 적가하였다. 상기 반응 혼합물을 6시간 동안 교반한 후, 증류하여 1,2-헥산다이올 6.75g을 수득하였다. (수율: 96.2%, GC 순도: 99.8%)1-Hexene (5 g, 0.0594 mole) and 30% aqueous hydrogen peroxide (10.7 mL, 1.5 eq.) Were added to formic acid (65 mL). A solution of iron chloride (0.48 g 0.05 eq.) In water (5 ml) was added dropwise while stirring the reaction mixture at 30 占 폚. The reaction mixture was stirred for 6 hours and then distilled to obtain 6.75 g of 1,2-hexanediol. (Yield: 96.2%, GC purity: 99.8%)
실시예 3.Example 3.
1-헥센(5g, 0.0594mole) 및 30% 과산화수소수(12.83mL, 1.8eq.)를 포름산(65mL)에 가하였다. 상기 반응 혼합물을 30℃에서 교반하면서, 염화 철(0.48g 0.05eq.)을 물(5ml)에 용해시킨 용액을 적가하였다. 상기 반응 혼합물을 6시간 동안 교반한 후, 증류하여 1,2-헥산다이올 6.78g을 수득하였다. (수율: 97.6%, GC 순도: 99.7%)1-Hexene (5 g, 0.0594 mole) and 30% hydrogen peroxide water (12.83 mL, 1.8 eq.) Were added to formic acid (65 mL). A solution of iron chloride (0.48 g 0.05 eq.) In water (5 ml) was added dropwise while stirring the reaction mixture at 30 占 폚. The reaction mixture was stirred for 6 hours and then distilled to obtain 6.78 g of 1,2-hexanediol. (Yield: 97.6%, GC purity: 99.7%).
실시예 4.Example 4.
1-헥센(5g, 0.0594mole) 및 30% 과산화수소수(10.7mL, 1.5eq.)를 포름산(65mL)에 가하였다. 상기 반응 혼합물을 40℃에서 교반하면서, 염화 철(0.48g 0.05eq.)을 물(5ml)에 용해시킨 용액을 적가하였다. 상기 반응 혼합물을 6시간 동안 교반한 후, 증류하여 1,2-헥산다이올 6.83g을 수득하였다. (수율: 98.3%, GC 순도: 99.8%)1-Hexene (5 g, 0.0594 mole) and 30% aqueous hydrogen peroxide (10.7 mL, 1.5 eq.) Were added to formic acid (65 mL). While stirring the reaction mixture at 40 占 폚, a solution of iron chloride (0.48 g, 0.05 eq.) Dissolved in water (5 ml) was added dropwise. The reaction mixture was stirred for 6 hours and then distilled to obtain 6.83 g of 1,2-hexanediol. (Yield: 98.3%, GC purity: 99.8%).
Claims (7)
상기 3가철 염이 1-헥센 1 당량에 대하여 0.02 ∼ 0.05 당량의 비율로 사용되고, 상기 과산화수소가 1-헥센 1 당량에 대하여 1.5 ∼ 1.8 당량의 비율로 사용되고, 상기 반응이 30 ∼ 40 ℃에서 4시간 내지 6시간 동안 수행되는 것을 특징으로 하는 1,2-헥산다이올의 제조방법.Claims 1. Process for the preparation of 1,2-hexanediol comprising reacting 1-hexene with hydrogen peroxide and trivalent salt,
Hexene is used in a proportion of 0.02 to 0.05 equivalent per 1 equivalent of 1-hexene, the hydrogen peroxide is used in a ratio of 1.5 to 1.8 equivalent per 1 equivalent of 1-hexene, the reaction is carried out at 30 to 40 DEG C for 4 hours ≪ / RTI > to < RTI ID = 0.0 > 6 hours. ≪ / RTI >
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| KR20210125222A (en) | 2020-04-08 | 2021-10-18 | 주식회사 글로우웨일 | A method for preparing 1,2-hexanediol |
| KR20230027499A (en) | 2021-08-19 | 2023-02-28 | 주식회사 산하첨단소재 | A method for producing colorless, odorless, high-purity 1,2-hexanediol |
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| EP4331684A2 (en) * | 2017-08-09 | 2024-03-06 | Symrise AG | 1,2-alkanediols |
| CN107903146B (en) * | 2017-11-23 | 2020-06-16 | 大连理工大学 | Method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene |
| EP3878833A1 (en) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Method for deodorizing 1,2-alkanediols by distillation |
| EP3878834A1 (en) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Method for deodorizing 1,2-alkanediols by distillation |
| EP3878832A1 (en) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Method for deodorizing 1,2-alkanediols by distillation |
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| US4479021A (en) | 1983-08-30 | 1984-10-23 | Ciba-Geigy Corporation | Continuous process for producing 1,2-alkanediols |
| US7385092B2 (en) | 2004-12-15 | 2008-06-10 | Degussa Ag | Process for preparing alkanediols and alkanetriols having a vicinal diol group |
| US20130211168A1 (en) | 2012-02-10 | 2013-08-15 | IFP Energies Nouvelles | Catalytic composition and process for oligomerization of olefins using said catalytic composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4479021A (en) | 1983-08-30 | 1984-10-23 | Ciba-Geigy Corporation | Continuous process for producing 1,2-alkanediols |
| US7385092B2 (en) | 2004-12-15 | 2008-06-10 | Degussa Ag | Process for preparing alkanediols and alkanetriols having a vicinal diol group |
| US20130211168A1 (en) | 2012-02-10 | 2013-08-15 | IFP Energies Nouvelles | Catalytic composition and process for oligomerization of olefins using said catalytic composition |
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| KR20210125222A (en) | 2020-04-08 | 2021-10-18 | 주식회사 글로우웨일 | A method for preparing 1,2-hexanediol |
| KR20230027499A (en) | 2021-08-19 | 2023-02-28 | 주식회사 산하첨단소재 | A method for producing colorless, odorless, high-purity 1,2-hexanediol |
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