KR20040024279A - The method of preparing high class alcohol from pollen - Google Patents

The method of preparing high class alcohol from pollen Download PDF

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KR20040024279A
KR20040024279A KR1020020055832A KR20020055832A KR20040024279A KR 20040024279 A KR20040024279 A KR 20040024279A KR 1020020055832 A KR1020020055832 A KR 1020020055832A KR 20020055832 A KR20020055832 A KR 20020055832A KR 20040024279 A KR20040024279 A KR 20040024279A
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alcohol
pollen
filtrate
hydrolysis
filtration
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박유석
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols

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Abstract

PURPOSE: Provided is a process for producing high-grade alcohol from pollen having much free state high-grade alcohol by hydrolysis, neutralization, filtration, distillation, and recrystallization. CONSTITUTION: The process for producing the high-grade alcohol from the pollen comprises the steps of: injecting the pollen into a mixture solution of caustic soda and alcohol and performing the hydrolysis for 1-3 hours; adding a mixture solution of hydrochloric acid and alcohol to neutralize excessive alkali; performing centrifugation or filtration to obtain a filtrate; distilling the filtrate to remove the alcohol; performing the recrystallization by adding acetone; and washing with water.

Description

화분으로부터 고급알콜을 제조하는 방법{THE METHOD OF PREPARING HIGH CLASS ALCOHOL FROM POLLEN}How to make high quality alcohol from pollen {THE METHOD OF PREPARING HIGH CLASS ALCOHOL FROM POLLEN}

본 발명은 화분에 포함되어 있는 에스테르형태의 고급알콜을 수산화나트륨·알콜용액으로 과량의 알카리를 가수분해시키고 염산·알콜용액으로 과량의 알카리를 중화시켜 증류시킨 다음 아세톤을 이용한 재결정을 통해 탄소수 18∼28의 고급알콜을 제조하는 방법에 관한 것이다.The present invention hydrolyzes the excess alkali of the ester type contained in the pollen with sodium hydroxide and alcohol solution, and neutralizes the excess alkali with hydrochloric acid and alcohol solution to distill and then recrystallize with acetone. It relates to a method for producing a higher alcohol of 28.

최근들어 옥타코사놀(C28H57OH)등 고급알콜이 인체에 대한 효능이 입증되면서 건강보조식품에서 고급알콜에 관한 관심이 점차 높아지고 있다. 따라서 현재 미국, 일본에서 옥타코사놀은 주원료로 하여 시판되고 있는 신제품들이 수백종에 이르며 체력증강, 지구력향상을 위한 식품소재로서 많은 연구가 진행되고 있다.Recently, as high-quality alcohols such as octacosanol (C 28 H 57 OH) have been proved to be effective for the human body, interest in high-grade alcohol in health supplements is gradually increasing. Therefore, there are hundreds of new products marketed as octacosanol as the main ingredient in the United States and Japan, and many studies are being conducted as food materials for physical strength improvement and endurance improvement.

특히, 옥타코사놀은 수천㎞ 이정을 쉬지 않고 날아가는 철새들의 에너지원으로 소맥배아 등 각종 곡물배아 또는 과일껍질에 들어 있지만 극히 미량밖에 존재하지 않기 때문에 추출하기 어렵고 가격도 엄청난 고가이다. 이와 같은 이유로 본 발명자는 옥타코사놀 등 고급알콜의 제조기술 개발을 위해 많은 천연물질을 대상으로 연구를 계속하여 온 결과 종래 고급알콜제조(추출)에 이용되고 있는 원료물질에 비해 화분에서 많은 양의 고급알콜 특히 옥타코사놀을 얻을 수 있음에 착안 이에 맞는 제조방법을 완성하게 되었다.In particular, octacosanol is an energy source for migratory birds that fly without stopping for thousands of kilometers, but is contained in various grain embryos or fruit skins such as wheat embryos, but it is difficult to extract because it is extremely small, and the price is enormously expensive. For this reason, the present inventors have continued to research many natural materials for the development of advanced alcohol manufacturing technology, such as octacosanol, and as a result, a large amount of high-grade alcohol in pollen compared to the raw materials used in the conventional high-grade alcohol production (extraction) In particular, since octacosanol can be obtained, a manufacturing method suitable for the present invention has been completed.

현재까지 개발된 방법은 주로 밀납으로부터 고급알콜을 추출하는 방법으로 미국특허 6,225,354호 및 6,235,795호가 알려져 있고 사탕수수로부터 고급알콜을 추출하는 방법으로 미국특허번호 5,633,156호 및 5,856,316호로 알려져 있으며 이들은 탄소수가 24∼34의 고급알콜을 얻는 방법이다.The methods developed to date are mainly US Pat. How to get 34 high alcohol.

그러나 사탕수수에는 유리(Free)상태의 고급알콜이 매우 적기 때문에 충분한 양의 고급알콜을 얻기위하여 강알카리조건에서 에스테르형태의 고급알콜을 가수분해(비누화반응)시켰다.However, because sugarcane has very few free alcohols in the free state, hydrolyzed (saponified) ester type alcohols under strong alkaline conditions to obtain a sufficient amount of higher alcohols.

또 밀납에는 미국특허 6,225,354호에서와같이 유리상태의 고급알콜이 존재하므로서 비누화반응을 거치지 않고 직접 추출하기도 하지만 어느 것이나 고급알콜의 함유량이 매우 적어 추출에 큰 어려움이 있다.In the beeswax, there is a high level of alcohol in the glass state, as in the US Patent No. 6,225,354, because it is directly extracted without undergoing a saponification reaction, but any of the very high content of alcohol is very difficult to extract.

본 발명을 먼저 많은 양의 고급알콜을 함유하고 있는 천연물질 특히 유리상태의 고급알콜이 많은 천연물질인 화분을 대상으로 이에 적절한 추출방법 등을 포함한 제조방법을 제공함에 목적이 있다.The present invention aims to provide a manufacturing method including an extraction method and the like suitable for a natural substance containing a large amount of higher alcohol, in particular, a pollen which is a natural substance having a lot of higher alcohol in a glass state.

본 발명은 화분에서 고급알콜을 제조하는 방법으로 먼저 여기에서 사용되는화분에는 밀남의 수십배에 달하는 높은 함량의 고급알콜을 있으며 60%이상의 고급알콜이 유리상태로 존재하기 때문에 높지 않은 온도에서도 가수분해 반응이 가능하며 추출만으로도 많은 양의 고급알콜을 얻을 수 있는 장점이 있으나 가장 효과적인 제조방법을 설명하면 화분을 가성소다·알콜용액에 넣고 1∼3시간 가수분해시킨 다음 여기에 염산·알콜용액을 첨가 중화시키고 이를 여과 또는 원심 분리하여 여액을 얻는다. 이 여액(알콜용액)을 증류하여 알콜을 제거한 다음 여기에 적량의 아세톤을 넣어 재결정화시키고 재결정화된 것을 물로 세정하므로서 유기용매를 완전히 제거하므로서 이취미가 없는 고급알콜을 얻게 된다.The present invention is a method for producing a high alcohol in a potted plant first used in the potted here is a high content of high-grade alcohol up to several tens of times of wheat, and since 60% or more high-quality alcohol is present in a glass state hydrolysis reaction even at high temperatures Although it is possible to obtain a large amount of high-quality alcohol by extraction alone, the most effective method of manufacturing is described in the potted caustic soda and alcohol solution, hydrolyzed for 1 to 3 hours, and then hydrochloric acid and alcohol solution are added to neutralization. The filtrate is obtained by filtration or centrifugation. The filtrate (alcohol solution) is distilled to remove alcohol, and then a moderate amount of acetone is added thereto to recrystallize and washed with water to completely remove the organic solvent to obtain a tasteless alcohol.

이상의 방법에서 여액을 증류하기전 여액에 탈수제(무수황산나트륨)을 넣어 완전 탈수한 다음 알콜을 증류하면 증류작업이 용이하다. 또 여기에서 혼합액으로 사용하는 알콜은 식용의 알콜을 사용한다.In the above method, before distilling the filtrate, a dehydrating agent (sodium sulphate anhydride) is added to the filtrate to completely dehydrate and distill the alcohol to facilitate distillation. In addition, the alcohol used as a mixed liquid here uses an edible alcohol.

상기방법의 이해를 돕기 위해 아래와 같이 구체적인 실시예를 들기로 한다.To help understand the method, specific examples will be given below.

(실시예 1)(Example 1)

화분 10g을 250ml 둥근밑 플라스크에 넣고 1N NaOH·알콜용액 100ml를 넣고 냉각기를 부착하여 85℃의 수욕(水浴)에서 비등시키면서 1시간 가수분해시킨다. 가수분해가 끝나면 6N HCI·알콜용액 20ml를 넣어 중화시키고 그 다음 여과 (또는 원심분리)하여 여액을 얻는다. 분리된 고형물은 50ml 의 알콜로 2회이상 씻고 세척액은 위의 여액과 합친다. 위에서 얻은 알콜용액(여액)을 미리 준비한 250ml 플라스크에 넣고 증류하여 알콜을 제거한다. 대부분의 알콜이 제거되면 적당한 양의 아세톤을 넣어 결정화시키고 결정화물을 물로 세척하여 잔류 유기용매를 완전히 제거하므로서 최종산물 5.1g을 얻었다.10 g of pollen is placed in a 250 ml round bottom flask, 100 ml of 1N NaOH and alcohol solution are added, and a cooler is attached and hydrolyzed for 1 hour while boiling in an 85 ° C. water bath. After hydrolysis, neutralize 20 ml of 6N HCI alcohol solution, and then filter (or centrifuge) to obtain a filtrate. The separated solids are washed twice with 50 ml of alcohol and the washings are combined with the filtrate above. The alcohol solution (filtrate) obtained above is placed in a 250 ml flask prepared in advance and distilled to remove alcohol. When most of the alcohol was removed, an appropriate amount of acetone was added to crystallize and the crystallized product was washed with water to completely remove the residual organic solvent, thereby obtaining 5.1 g of the final product.

(실시예 2)(Example 2)

화분 10g을 250ml 둥근밑 플라스크에 넣고 1N NaOH·알콜용액 150ml를 넣고 냉각기를 부착하여 85℃의 수욕(水浴)에서 비등시키면서 1시간 가수분해시킨다. 가수분해가 끝나면 6N HCI·알콜용액 20ml를 넣어 중화시키고 그 다음 여과 (또는 원심분리)하여 여액을 얻는다. 분리된 고형물은 50ml 의 알콜로 2회이상 씻고 세척액은 위의 여액과 합친다. 위에서 얻은 얼은 알콜용액(여액)에 무수황산 나트륨을 넣어 탈수시킨 후 미리 준비한 250ml 플라스크에 넣고 증류하여 알콜을 제거한다. 대부분의 알콜이 제거되면 적당한 양의 아세톤을 넣어 결정화시키고 이 결정화물을 물로 세척하여 잔류유기용매를 완전히 제거하고 최종산물 4g을 얻었다.10 g of pollen is placed in a 250 ml round bottom flask, 150 ml of 1N NaOH and alcohol solution are added, and a cooler is attached and hydrolyzed for 1 hour while boiling in an 85 ° C. water bath. After hydrolysis, neutralize 20 ml of 6N HCI alcohol solution, and then filter (or centrifuge) to obtain a filtrate. The separated solids are washed twice with 50 ml of alcohol and the washings are combined with the filtrate above. The ice obtained above is dehydrated by adding anhydrous sodium sulfate to an alcohol solution (filtrate), and then distilled into a 250 ml flask prepared in advance to remove alcohol. After most of the alcohol was removed, an appropriate amount of acetone was added to crystallize and the crystallized product was washed with water to completely remove the residual organic solvent to obtain 4 g of the final product.

(실시예 3)(Example 3)

화분 10g과 1N NaOII·알콜용액 150ml를 250ml 둥근밑 플라스크에 넣고 실온에서 3시간 가수분해시킨다. 가수분해가 끝나면 6N HCI·알콜용액 20ml를 넣어 중화시키고, 그다음 여과 (또는 원심분리)하여 여액을 얻는다. 분리된 고형물은 50ml의 알콜로 2회이상 씻고 세척액은 위의 여액과 합친다. 위에서 얻은 알콜용액(여액)에 무수황산 나트륨을 넣어 탈수시킨 후 미리 준비한 250ml 플라스크에 넣고 증류하여 알콜을 제거한다. 대부분의 알콜이 제거되면 적당한 양의 아세톤을 넣어 결정화시킨 다음 결정화물을 물로 세척하여 잔류유기용매를 완전히 제거하므로서 최종산물 4.6g을 얻었다.10 g of pollen and 150 ml of 1N NaOII alcohol solution are placed in a 250 ml round bottom flask and hydrolyzed at room temperature for 3 hours. After hydrolysis, neutralize with 20 ml of 6N HCI alcohol solution, and then filter (or centrifuge) to obtain a filtrate. The separated solids are washed twice with 50 ml of alcohol and the washings are combined with the filtrate above. Anhydrous sodium sulfate is added to the alcohol solution (filtrate) obtained above, dehydrated, and then distilled into a 250 ml flask prepared in advance to remove alcohol. When most of the alcohol was removed, an appropriate amount of acetone was added to crystallize, and then the crystallized product was washed with water to completely remove the residual organic solvent, thereby obtaining 4.6 g of the final product.

상기 실시예 (1)∼(3)에서 화분으로부터 얻어진 고급알콜의 가스크로마토그래프를 그림1로 나타냈다.Fig. 1 shows the gas chromatograph of the higher alcohol obtained from pollen in Examples (1) to (3).

그림1. 본 발명에서 얻어진 고급알콜의 가스크로마토그래프Figure 1. Gas chromatograph of higher alcohol obtained in the present invention

이상의 그림1에서 나타난 바와 같이 본 발명에 의한 방법으로 화분으로부터 얻어진 고급알콜은 탄소수 18∼28의 고급알콜 (CnH2n+1OH, n=18-28) 임을 알 수 있다.As shown in Figure 1 above, it can be seen that the higher alcohol obtained from pollen by the method according to the present invention is a higher alcohol having 18 to 28 carbon atoms (C n H 2n + 1 OH, n = 18-28).

본 발명에 의한 방법으로 제조된 고급알콜은 탄소수 18∼28인 고급알콜들로서 최근 고급알콜이 인체에 대한 효능이 입증되면서 건강보조식품에서 고급알콜에 관한 관심이 높아지고 있다.Higher alcohols produced by the method according to the present invention are higher alcohols having 18 to 28 carbon atoms, and as recent high alcohols have been demonstrated to be effective on the human body, interest in higher alcohols in health foods is increasing.

특히 상기 고급알콜 중 상당량의 함량을 차지하는 옥타코사놀은 근글리코겐의 저장량을 증가시켜 근력 및 근 지구력 효과가 있고 에너지의 저장량을 증가시킴은 물론 순발력을 향상시키며 근육의 지방 이용률을 증가시키고 최대 산소습취량을 증가시키며 심부담도를 감소시키는 작용과 그밖에도 심장기능 강화효능이 있다는 사실이 입증되므로서 향후 건강식품으로의 이용률이 크게 기대되는 고급알콜제품이라 할 수 있다.In particular, octacosanol, which occupies a considerable amount of the higher alcohols, increases muscle glycogen storage, increases muscle and endurance effect, increases energy storage, improves quickness, increases muscle fat utilization, and maximizes oxygen uptake. It is a high-quality alcohol product that is expected to increase the utilization of the health food in the future as it is proved that there is an effect to increase the heart burden and increase the heart function.

Claims (1)

화분을 가성소다·알콜 혼합용액에 넣고 1∼3시간 가수분해시킨 다음 여기에 염산·알콜 혼합용액을 첨가, 과량의 알카리를 중화시키고 이를 원심분리 또는 여과로 여액을 얻은 후 이 여액을 증류하여 알콜을 제거하고 여기서 적량의 아세톤을 넣어 재결정화 시키고 재결정화된 것을 물로 세정함을 특징으로 하는 화분으로부터 고급알콜을 제조하는 방법Put the pollen in a caustic soda-alcohol mixture solution and hydrolyze for 1 to 3 hours, add hydrochloric acid and alcohol mixture to neutralize the excess alkali, and obtain the filtrate by centrifugation or filtration. To prepare a higher alcohol from the potted plant, characterized in that a suitable amount of acetone is added to recrystallize and the recrystallized is washed with water.
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KR100685681B1 (en) * 2005-07-26 2007-02-26 전북대학교산학협력단 Method for preparing long-chained lipids with the high concentration of policosanol or octacosanol from grain sorghum

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* Cited by examiner, † Cited by third party
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CU22229A1 (en) * 1992-09-29 1996-01-31 Dalmer Lab Sa Polycosanol, a mixture of superior primary aliphatic as platelet hyperclumping, ischemic accidents, thrombosis and also effective against chemically induced gastric and procedure for its preparation from sugar cane.alcohols for treating atherosclerotic complications such
US20020058713A1 (en) * 1999-06-21 2002-05-16 Gamble William R. High molecular weight primary aliphatic alcohols obtained from natural products and uses thereof
US6225354B1 (en) * 1999-06-21 2001-05-01 Cholesterol Control Laboratories, Inc. High molecular weight primary aliphatic alcohols obtained from beeswax and pharmaceutical use thereof

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KR100685681B1 (en) * 2005-07-26 2007-02-26 전북대학교산학협력단 Method for preparing long-chained lipids with the high concentration of policosanol or octacosanol from grain sorghum

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