JPH0256442A - Production of higher alcohol - Google Patents
Production of higher alcoholInfo
- Publication number
- JPH0256442A JPH0256442A JP20724188A JP20724188A JPH0256442A JP H0256442 A JPH0256442 A JP H0256442A JP 20724188 A JP20724188 A JP 20724188A JP 20724188 A JP20724188 A JP 20724188A JP H0256442 A JPH0256442 A JP H0256442A
- Authority
- JP
- Japan
- Prior art keywords
- water
- higher alcohols
- alcohol
- wax
- natural wax
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 5
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001298 alcohols Chemical class 0.000 abstract description 13
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 11
- 239000000194 fatty acid Substances 0.000 abstract description 11
- 229930195729 fatty acid Natural products 0.000 abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 10
- -1 fatty acid salts Chemical class 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000000638 solvent extraction Methods 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003208 petroleum Substances 0.000 abstract description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 abstract description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract description 2
- 235000013402 health food Nutrition 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract description 2
- 239000008096 xylene Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000001993 wax Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012164 animal wax Substances 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012183 esparto wax Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012176 shellac wax Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、天然ワックス中に含まれている高級アルコー
ルを分離、精製する方法に関し、詳し、くは天然ワック
スを鹸化分解した後、特定の混合溶媒によって液々抽出
することにより高級アルコールを得る方法に関する。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a method for separating and refining higher alcohols contained in natural wax, and more particularly, relates to a method for separating and purifying higher alcohols contained in natural wax, and more specifically, for separating and purifying higher alcohols contained in natural wax. This invention relates to a method for obtaining higher alcohols by liquid-liquid extraction with mixed solvents.
（従来の技術）
天然ワックスは炭素数２２から３８の高級アルコールと
高級脂肪酸とからなるエステルを含んでいる。(Prior Art) Natural wax contains an ester consisting of a higher alcohol having 22 to 38 carbon atoms and a higher fatty acid.
この高級アルコール中にはへキサコサノール、オクタコ
サノール、トリアコンタノールなどその生理活性が注目
され、医薬の前駆体または健康食品として期待されるも
のが含まれている。These higher alcohols include hexacosanol, octacosanol, and triacontanol, which are attracting attention for their physiological activity and are expected to be used as pharmaceutical precursors or health foods.
従来、これらの天然ワックスを分解し高級アルコールを
得る方法としては、鹸化分解後にシリカゲル、アルミナ
、活性炭などに脂肪酸塩を吸着させて除去する方法（例
えば特開昭６１−２２７５４３号、特開昭６３−８３４
７号など）、あるいは分子蒸留によって脂肪酸メチルエ
ステルを除く方法などがあった。Conventionally, as a method of decomposing these natural waxes to obtain higher alcohols, a method of removing fatty acid salts by adsorbing them to silica gel, alumina, activated carbon, etc. after saponification and decomposition (for example, JP-A-61-227543, JP-A-63 -834
No. 7), or methods to remove fatty acid methyl esters by molecular distillation.
（発明が解決しようとする課題）
しかしながら、このような吸着法では吸着処理、濾過工
程など効率が十分とは言えず、また分子蒸留法は装置全
体を９０℃以上に保温できるような特別の装置が必要で
あるので、コストが高くなるという問題点があった。(Problem to be solved by the invention) However, such adsorption methods cannot be said to have sufficient efficiency in adsorption treatment and filtration processes, and molecular distillation methods require special equipment that can keep the entire equipment at a temperature of 90°C or higher. Since this method requires
本発明の目的は、天然ワックスから、高級アルコールを
簡便な方法で高収率で得る方法を提供することである。An object of the present invention is to provide a method for obtaining higher alcohols from natural waxes in a simple manner and in high yield.
（課題を解決するための手段）
本発明は、天然ワックスをアルカリ金属の水酸化物で鹸
化分解した後、無極性有機溶剤／アルコール／水系の混
合溶媒を用いて液々抽出することを特徴とする高級アル
コールの製造方法である。(Means for Solving the Problems) The present invention is characterized in that natural wax is saponified and decomposed with an alkali metal hydroxide and then liquid-liquid extracted using a non-polar organic solvent/alcohol/water mixed solvent. This is a method for producing higher alcohol.
本発明に用いる天然ワックスとしてはライスワックス、
キャンデリラワックス、エスパルトワックス、カルナウ
バワックスなどの植物ワックス、鯨油ワックス、虫白ろ
う、シェラツクワックスなどの動物ワックスが挙げられ
る。The natural waxes used in the present invention include rice wax,
Examples include vegetable waxes such as candelilla wax, esparto wax, and carnauba wax, and animal waxes such as whale oil wax, insect white wax, and shellac wax.
アルカリ金属の水酸化物としては、例えば水酸化カリウ
ム、水酸化ナトリウムが使用できる。その使用量は天然
ワックス１モル当たり１〜２モルである。As the alkali metal hydroxide, for example, potassium hydroxide and sodium hydroxide can be used. The amount used is 1 to 2 mol per mol of natural wax.
上記の天然ワックスは、アルコール；水（例えばエタノ
ール：水−Ｉ：ｌν／ν）溶媒中で、または無溶媒系で
アルカリ金属の水酸化物を加えて鹸化分解する。反応温
度は溶媒系で５０から１００℃、無溶媒系で１５０から
３００℃で行われる。反応時間は溶媒系で２０分から５
時間、無溶媒系で１０から６０分である。このようにし
て得た鹸化分解物を前記混合溶媒を用いて液々抽出する
。The above natural wax is saponified and decomposed in an alcohol; water (for example, ethanol:water-I:lv/v) solvent or in a solvent-free system by adding an alkali metal hydroxide. The reaction temperature is 50 to 100°C in a solvent system, and 150 to 300°C in a solvent-free system. Reaction time is 20 minutes to 5 minutes in solvent system.
The time is 10 to 60 minutes in a solvent-free system. The saponified decomposition product obtained in this way is extracted in a liquid manner using the above-mentioned mixed solvent.
本発明に用いる無極性有機溶剤としては、例えばヘキサ
ン、ヘプタン、オクタン、イソオクタン、石油エーテル
、石油ベンジン、ベンゼン、トルエン、キシレンなどの
炭化水素があり、アルコールとしてはメタノール、エタ
ノール、プロパツール等がある。Examples of non-polar organic solvents used in the present invention include hydrocarbons such as hexane, heptane, octane, isooctane, petroleum ether, petroleum benzene, benzene, toluene, and xylene; examples of alcohols include methanol, ethanol, propatool, etc. .
本発明において混合溶媒の混合比は無極性有機溶剤／ア
ルコール／水＝ｔ：Ｏ，３〜３：０．３〜３Ｖ／ν／ν
）であり２Ｎに分店するように調製する。In the present invention, the mixing ratio of the mixed solvent is nonpolar organic solvent/alcohol/water = t:O, 3-3:0.3-3V/ν/ν
) and prepared so that it is divided into 2N.
液々抽出は、例えば分解物１００ｇ当たりヘキサン２０
．０〜６００ ｍｌ、６０℃の温水２００〜６００ｍ１
、エタノール２００〜６００ ｍｌを順次加えて処理す
る。その結果、高級アルコールの濃縮された上層と脂肪
酸塩のね：縮された下層に分層するので、下層を除き、
更に同様の操作を繰り返すと、上層には極微量の脂肪酸
塩を含み、大部分が高級アルコールである区分が得られ
る。これを６０℃の温水１０１００Ｏで３回洗浄してｍ
ｆｆ１の脂肪酸塩をのぞいた後、約０．２から０．５ｇ
の活性炭で処理して着色物を吸収させ、これを濾過して
除き、この後１０℃で１２時間、晶析処理して生じた結
晶を濾過し、減圧乾燥すると白色の高級アルコールが約
２０〜３２ｇ得られる。Liquid-liquid extraction is performed using, for example, 20 g of hexane per 100 g of decomposed product.
．． 0~600ml, 60℃ hot water 200~600ml
, 200 to 600 ml of ethanol were added sequentially. As a result, the upper layer is concentrated with higher alcohols and the lower layer is concentrated with fatty acid salts, so the lower layer is removed.
Further repeating the same operation yields a fraction in which the upper layer contains a very small amount of fatty acid salt and is mostly higher alcohol. Wash this three times with 60℃ warm water 10100O.
Approximately 0.2 to 0.5 g after excluding the fatty acid salt of ff1
The colored substances are absorbed by treatment with activated carbon, which is removed by filtration, and then crystallized at 10°C for 12 hours. The resulting crystals are filtered and dried under reduced pressure, resulting in a white higher alcohol of about 20~ 32g obtained.
（発明の効果）
本発明によれば、特定の混合溶媒を用いて液々抽出を行
うので、これまで分離することが困難であった脂肪酸塩
と高級アルコールとを精度良く分離でき、前便な方法に
もかかわらす高収率で高純度の目的物を得ることができ
る。(Effects of the Invention) According to the present invention, since liquid-liquid extraction is performed using a specific mixed solvent, fatty acid salts and higher alcohols, which have been difficult to separate, can be separated with high accuracy, and pre-extraction is possible. Regardless of the method used, the desired product can be obtained in high yield and with high purity.
（実施例）
以下、実施例及び比較例を用いて本発明を具体的に説明
する。(Example) Hereinafter, the present invention will be specifically described using Examples and Comparative Examples.
実施例１
ライスワックス５０ｇ（野田ワックス■製晶、約４０％
の高級アルコールを含む）に水酸化カリウム７ｇを溶解
させた水５０−とエタノール５０ｍ１を加え、還流下（
８９〜９０℃）で反応させる。３０分で鹸化分解が終了
し、透明な褐色溶液となる。この溶液を６０℃まで冷却
し、ヘキサン２００ ｍｌ、水１００ ｄ、エタノール
２００ ｄを順次加え、還流下（６３℃）で１０分間攪
拌すると二層に分離する。下層を除き、同様にヘキサン
１００−１水５０−、エタノール１００ ｒｎｌを順次
添加し、１０分間攪拌の後、下層を除く。残った層には
極微量の脂肪酸カリウムが含まれているので、６０℃の
温水５００−で３回洗浄して、これを完全に除く。次に
０．２ｇの活性炭を加え、約１０分間撹拌して着色物を
吸着させ濾過して除く。この後１０℃で１２時間放置し
て晶析させ、結晶を濾別して後、減圧乾燥して１６ｇの
高級アルコールを得た。Example 1 Rice wax 50g (Noda wax ■ crystallized, about 40%
50ml of water containing 7g of potassium hydroxide and 50ml of ethanol were added to the solution (containing higher alcohol), and the mixture was heated under reflux (
89-90°C). Saponification and decomposition are completed in 30 minutes, resulting in a transparent brown solution. This solution is cooled to 60° C., 200 ml of hexane, 100 d of water, and 200 d of ethanol are sequentially added, and the mixture is stirred under reflux (63° C.) for 10 minutes to separate into two layers. After removing the lower layer, 100 parts of hexane, 50 parts of water, and 100 rnl of ethanol were sequentially added in the same manner, and after stirring for 10 minutes, the lower layer was removed. Since the remaining layer contains a very small amount of potassium fatty acid, it is washed three times with 500°C of warm water at 60°C to completely remove this. Next, 0.2 g of activated carbon is added and stirred for about 10 minutes to adsorb colored substances and remove them by filtration. Thereafter, the mixture was allowed to stand at 10° C. for 12 hours to crystallize, and the crystals were filtered and dried under reduced pressure to obtain 16 g of higher alcohol.
このものをガスクロマトグラフィー質■分析計により分
析した結果、脂肪酸はほとんど含まれていなかった。高
級アルコールの純度は９５％以上であり、収率は約８０
％であった。Analysis of this product using a gas chromatography quality analyzer revealed that it contained almost no fatty acids. The purity of the higher alcohol is over 95%, and the yield is about 80%.
%Met.
実施例２
実施例１においてライスワックス５０ｇを、カルナウバ
ワックス（野田ワックス０１製品、約４０％の高級アル
コールを含む）５０ｇに変えた以外は同様に行った。１
４ｇの高級アルコールが得られ、収率は７０％であった
。Example 2 The same procedure as in Example 1 was carried out except that 50 g of rice wax was replaced with 50 g of carnauba wax (Noda Wax 01 product, containing about 40% higher alcohol). 1
4 g of higher alcohol was obtained, with a yield of 70%.
実施例３
実施例１において水酸化カリウム７ｇを、水酸化ナトリ
ウム５ｇに変えた以外は同様に行った。Example 3 The same procedure as in Example 1 was carried out except that 7 g of potassium hydroxide was replaced with 5 g of sodium hydroxide.
１５ｇの高級アルコールが得られ、収率は７５％であっ
た。15 g of higher alcohol was obtained, with a yield of 75%.
実施例４
実施例１においてヘキサンの代わりにオクタンを、また
エタノールの代わりにメタノールを用いた以外は、実施
例１と同様に行った。Example 4 The same procedure as in Example 1 was carried out except that octane was used instead of hexane and methanol was used instead of ethanol.
高級アルコールが１４ｇ得られ、収率は７５％であった
。14g of higher alcohol was obtained, with a yield of 75%.
比較例１
ライスワックス５０ｇをＩｇの水酸化ナトリウムを溶解
させたメタノール５００−に加え、還流下で１時間エス
テル交換反応を行った。その後、減圧下で濃縮してメタ
ノールを除き、分子蒸留にかけた。温度は２４０℃、減
圧度は０．０１ｍｍ１１ｇで行った。Comparative Example 1 50 g of rice wax was added to 500 g of methanol in which Ig of sodium hydroxide was dissolved, and a transesterification reaction was carried out under reflux for 1 hour. Thereafter, it was concentrated under reduced pressure to remove methanol and subjected to molecular distillation. The temperature was 240° C., and the degree of vacuum was 0.01 mm and 11 g.
その際、リボンヒーターによってガラス部分を加熱して
装置全体が９０℃以上になるように保った。At that time, the glass portion was heated by a ribbon heater to maintain the temperature of the entire apparatus at 90° C. or higher.
脂肪酸メチルが蒸留され、高級アルコールが残部として
濃縮された。しかし、高級アルコールの収率は約６０％
と低く、その中には不純物としておよそ３０％の脂肪酸
メチルが含まれていた。The fatty acid methyl was distilled and the higher alcohol was concentrated as the remainder. However, the yield of higher alcohol is about 60%.
It contained approximately 30% fatty acid methyl as an impurity.
Claims (1)
た後、無極性有機溶剤／アルコール／水系の混合溶媒を
用いて液々抽出することを特徴とする高級アルコールの
製造方法。A method for producing a higher alcohol, which comprises saponifying and decomposing natural wax with an alkali metal hydroxide, and then extracting the wax using a non-polar organic solvent/alcohol/water mixed solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20724188A JPH0256442A (en) | 1988-08-23 | 1988-08-23 | Production of higher alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20724188A JPH0256442A (en) | 1988-08-23 | 1988-08-23 | Production of higher alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0256442A true JPH0256442A (en) | 1990-02-26 |
Family
ID=16536554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20724188A Pending JPH0256442A (en) | 1988-08-23 | 1988-08-23 | Production of higher alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0256442A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006517583A (en) * | 2003-01-31 | 2006-07-27 | ユニゲン・ファーマシューティカルス・インコーポレーテッド | Policosanol from Elycerus pellawax |
-
1988
- 1988-08-23 JP JP20724188A patent/JPH0256442A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006517583A (en) * | 2003-01-31 | 2006-07-27 | ユニゲン・ファーマシューティカルス・インコーポレーテッド | Policosanol from Elycerus pellawax |
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