JPH0461856B2 - - Google Patents
Info
- Publication number
- JPH0461856B2 JPH0461856B2 JP59042863A JP4286384A JPH0461856B2 JP H0461856 B2 JPH0461856 B2 JP H0461856B2 JP 59042863 A JP59042863 A JP 59042863A JP 4286384 A JP4286384 A JP 4286384A JP H0461856 B2 JPH0461856 B2 JP H0461856B2
- Authority
- JP
- Japan
- Prior art keywords
- wax
- alcohol
- higher alcohol
- producing
- alcohols
- 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.)
- Expired - Lifetime
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000001993 wax Substances 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 244000020551 Helianthus annuus Species 0.000 claims description 4
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 4
- 239000004170 rice bran wax Substances 0.000 claims description 4
- 235000019384 rice bran wax Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 241000209140 Triticum Species 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 235000013871 bee wax Nutrition 0.000 claims description 2
- 239000012166 beeswax Substances 0.000 claims description 2
- 229940092738 beeswax Drugs 0.000 claims description 2
- 239000012170 montan wax Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、主として高級脂肪酸と高級アルコー
ルからなるワツクスを低級アルコールとエステル
交換することにより、高級アルコールを製造する
方法に関する。
近年、オクタコサノール等の高級アルコールが
いわゆる健康食品等として注目され、その需要が
高まつている。
従来、エステル構造を有するワツクス類からア
ルコールを得るにはNaOH、KOH等のアルカリ
によつてけん化分解し、生成した石けんを水洗い
して除くことによつてアルコールを得るのが一般
的な方法であつた。しかし、ひまわりワツクスや
米ぬかワツクのように高級飽和アルコールと高級
飽和脂肪酸を含むワツクスは、生成した石けんが
高融点であり、かつ水に対する溶解性が乏しい上
に乳化が激しいため、高級アルコールの分離が困
難である。この乳化液から石けんを除くには、遠
心分離や脱水後の分子蒸留といつた手段が可能で
あるものの、いずれも高級アルコールを高純度で
しかも高収率で得るには手間とコストがかかる。
また、石けんを分解した後に脂肪酸とアルコール
を分離することも可能であるが、融点・沸点等の
物性が高級アルコールと高級脂肪酸では似てお
り、両者の分離がきわめて困難である。
本発明者らは、このようにけん化分解法による
の分解後の乳化が激しく、分離が難しいワツクス
から高級アルコールを得る方法について鋭意研究
を重ねた結果、低級アルコールを用いてエステル
交換を行い、これを溶剤で再結晶することにより
容易かつ高収率で高純度の高級アルコールを製造
し得ることを見出し、本発明を完成したものであ
る。
以下本発明の構成について詳しく説明する。
本発明でいうワツクスとは、ひまわりワツク
ス、米ぬかワツクス、モンタンワツクス、ビーズ
ワツクス、小麦胚芽ワツクス等の高級アルコール
と高級脂肪酸のエステルからなるワツクスであ
る。
本発明はこれらのワツクスをメタノール、エタ
ノール、プロパノール、ブタノール等の低級アル
コールでエステル交換する。
エステル交換の条件は、通常のNaOH、
KOH、ソジウムメトキシド等のアルカリ触媒や
HCl、H2SO4等の酸触媒をもちいることができ、
使用した低級アルコールの沸点近くで数時間反応
させれば良い。
得られた反応液を溶剤で処理して目的の高級ア
ルコールを得るのであるが、その方法として例え
ば次の様な手段を用いる。即ちその一つは反応液
を、冷却後濾過し、触媒が除かれるまでケーキを
水洗後、メタノール、エタノール、プロパノー
ル、ブタノールなどの低級アルコールで再結晶を
繰り返すことによつて高純度の高級アルコールを
得るものである。また、他の一つは反応後にキシ
レン、クロロホルム等の非極性有機溶媒を加えて
反応物を溶解させたのち、触媒がなくなるまで水
洗し、溶媒層を冷却後折出した結晶物を濾過し、
この結晶物をキシレン、クロロホルム等を用いて
再結晶を繰り返すことによつて高純度の高級アル
コールを得るものである。
上記の本発明による高級アルコールの製造法
は、従来法例えばNaOHでけん化分解した後、
遠心分離を用いて水洗する方法に比べると、操作
の容易さ、収率、純度において明らかに優れてい
る。
以下実施例で説明する。
実施例 １
米ぬかワツクス400ｇにメタノール３と
NaOH1.6ｇを加え、４〜６時間還流撹拌する。
室温まで冷却後、濾過する。ケーシに温水を加
え、しばらく撹拌した後、濾過する。再びケーキ
を温水で洗浄する。この操作を濾液の洗浄水から
触媒に用いたアルカリが検出できなくなるまで３
〜４回繰り返す。このケーキを１の熱メタノー
ルに溶かし、再結晶を行うと、白色粉末約70ｇが
得られる。この白色粉末の性状は、次の通りであ
る。
融点：70〜74℃
アルコール純度：92.3％
アルコール組成（ガスクロマトグラフイーによ
る）
The present invention relates to a method for producing a higher alcohol by transesterifying a wax mainly composed of a higher fatty acid and a higher alcohol with a lower alcohol. In recent years, higher alcohols such as octacosanol have attracted attention as so-called health foods, and the demand for them has been increasing. Conventionally, the common method for obtaining alcohol from waxes having an ester structure has been to saponify and decompose them with an alkali such as NaOH or KOH, and to remove the soap produced by washing with water. Ta. However, waxes containing higher saturated alcohols and higher saturated fatty acids, such as sunflower wax and rice bran wax, produce soap with a high melting point, poor solubility in water, and strong emulsification, making it difficult to separate the higher alcohols. Have difficulty. Although it is possible to remove soap from this emulsion by centrifugation or molecular distillation after dehydration, both methods require time and cost to obtain higher alcohols with high purity and high yield.
It is also possible to separate fatty acids and alcohols after decomposing soap, but higher alcohols and higher fatty acids have similar physical properties such as melting point and boiling point, making it extremely difficult to separate the two. The inventors of the present invention have conducted extensive research on a method for obtaining higher alcohols from wax that is difficult to separate due to its intense emulsification after decomposition by the saponification method. The present invention has been completed based on the discovery that a highly pure higher alcohol can be easily produced in high yield by recrystallizing it with a solvent. The configuration of the present invention will be explained in detail below. The wax used in the present invention is a wax made of an ester of higher alcohol and higher fatty acid, such as sunflower wax, rice bran wax, montan wax, bees wax, and wheat germ wax. In the present invention, these waxes are transesterified with lower alcohols such as methanol, ethanol, propanol, and butanol. The conditions for transesterification are normal NaOH,
Alkaline catalysts such as KOH and sodium methoxide
Acid catalysts such as HCl and H 2 SO 4 can be used,
The reaction can be carried out for several hours near the boiling point of the lower alcohol used. The obtained reaction solution is treated with a solvent to obtain the desired higher alcohol, for example, the following method is used. One method is to filter the reaction solution after cooling, wash the cake with water until the catalyst is removed, and repeat recrystallization with lower alcohols such as methanol, ethanol, propanol, butanol, etc. to obtain a highly pure higher alcohol. It's something you get. The other method is to add a non-polar organic solvent such as xylene or chloroform after the reaction to dissolve the reactants, then wash with water until the catalyst disappears, cool the solvent layer, and then filter the precipitated crystals.
A highly pure higher alcohol is obtained by repeatedly recrystallizing this crystal using xylene, chloroform, etc. The above-mentioned method for producing higher alcohol according to the present invention involves a conventional method such as saponification and decomposition with NaOH.
Compared to the method of centrifugation and washing with water, it is clearly superior in terms of ease of operation, yield, and purity. This will be explained below using examples. Example 1 400g of rice bran wax and 3 methanol
Add 1.6 g of NaOH and stir under reflux for 4 to 6 hours.
After cooling to room temperature, filter. Add warm water to the case, stir for a while, and then filter. Wash the cake again with warm water. Repeat this operation 3 times until the alkali used for the catalyst can no longer be detected in the filtrate wash water.
Repeat ~4 times. When this cake is dissolved in hot methanol (1) and recrystallized, about 70 g of white powder is obtained. The properties of this white powder are as follows. Melting point: 70-74℃ Alcohol purity: 92.3% Alcohol composition (by gas chromatography)
【表】
実施例 ２
ひまわりワツクス400ｇにエタノール３ｇと
NaOH1.6ｇを加え、４〜６時間還流撹拌する。
反応液に熱キシレン３と温水６を加え撹拌す
る。水層除去後、さらに温水６を加え、水洗を
接触に用いたアルカリが除かれるまで２〜３回繰
り返す。キシレン層を10℃まで冷却後、濾過す
る。ケーシを500mlのキシレンで再結晶すると、
白色粉末約100ｇが得られる。この白色粉末の性
状は次の通りである。
融点：70〜72℃
アルコール含量：92.3％
アルコール組成（ガスクロマトグラフイーによ
る）[Table] Example 2 400g of sunflower wax and 3g of ethanol
Add 1.6 g of NaOH and stir under reflux for 4 to 6 hours.
3 of hot xylene and 6 of warm water are added to the reaction solution and stirred. After removing the aqueous layer, further warm water 6 is added and the water washing is repeated 2 to 3 times until the alkali used for contacting is removed. After cooling the xylene layer to 10°C, filter it. When you recrystallize the cassava in 500ml of xylene,
Approximately 100 g of white powder is obtained. The properties of this white powder are as follows. Melting point: 70-72℃ Alcohol content: 92.3% Alcohol composition (by gas chromatography)
Claims (1)
らなるワツクスを低級アルコールとエステル交換
した後、反応物を溶剤で再結晶することにより高
級アルコールを得ることを特徴とする高級アルコ
ールの製造法。 ２ ワツクスがひまわりワツクス、米ぬかワツク
ス、モンタンワツクス、ビーズワツクスまたは小
麦胚芽ワツクスである特許請求の範囲第１項記載
の高級アルコールの製造法。 ３ エステル交換に使用する低級アルコールが、
メタノール、エタノール、プロパノールまたはブ
タノールである特許請求の範囲第１項記載の高級
アルコールの製造法。[Scope of Claims] 1. A method for producing a higher alcohol, which comprises transesterifying a wax mainly consisting of a higher fatty acid and a higher alcohol with a lower alcohol, and then obtaining a higher alcohol by recrystallizing the reactant with a solvent. 2. The method for producing a higher alcohol according to claim 1, wherein the wax is sunflower wax, rice bran wax, Montan wax, bees wax, or wheat germ wax. 3 The lower alcohol used for transesterification is
The method for producing a higher alcohol according to claim 1, which is methanol, ethanol, propanol or butanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4286384A JPS60188334A (en) | 1984-03-08 | 1984-03-08 | Preparation of higher alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4286384A JPS60188334A (en) | 1984-03-08 | 1984-03-08 | Preparation of higher alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188334A JPS60188334A (en) | 1985-09-25 |
| JPH0461856B2 true JPH0461856B2 (en) | 1992-10-02 |
Family
ID=12647866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4286384A Granted JPS60188334A (en) | 1984-03-08 | 1984-03-08 | Preparation of higher alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188334A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU641630B2 (en) * | 1989-01-17 | 1993-09-30 | Davy Mckee (London) Limited | Process for the production of fatty alcohols |
| GB8900993D0 (en) * | 1989-01-17 | 1989-03-08 | Davy Mckee London | Process |
| DE102004055858A1 (en) * | 2004-11-19 | 2006-05-24 | Clariant Gmbh | Use of long-chain alcohols to effectively lower elevated cholesterol levels |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60155143A (en) * | 1984-01-24 | 1985-08-15 | Nippon Oil & Fats Co Ltd | Method for separating aliphatic higher alcohol from natural wax |
-
1984
- 1984-03-08 JP JP4286384A patent/JPS60188334A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60155143A (en) * | 1984-01-24 | 1985-08-15 | Nippon Oil & Fats Co Ltd | Method for separating aliphatic higher alcohol from natural wax |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188334A (en) | 1985-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2494366A (en) | Production of fatty esters | |
| US4164506A (en) | Process for producing lower alcohol esters of fatty acids | |
| JPS6151000B2 (en) | ||
| JP4796695B2 (en) | Method for recovering plant sterols | |
| US4104464A (en) | Purification of sucrose esters | |
| JPH0461856B2 (en) | ||
| US7560578B2 (en) | Palm-based hydroxy fatty acid | |
| JPS6046104B2 (en) | Method for producing butene derivatives | |
| US2079403A (en) | Reduction of acyloins | |
| EP1625105B1 (en) | Method of making alkyl esters using pressure | |
| US5117017A (en) | Process for preparing high purity 3-α-7-β-dihydroxycholanic acid | |
| RU1836348C (en) | Method for obtaining higher alkyl ethers of (4-amino-3,5-dichloro-6-fluoro-2-pyridinyloxy) acetic acid | |
| US2729655A (en) | Production of sterols | |
| US2399959A (en) | Process of producing esters | |
| EP1672053B1 (en) | High purity palm monoglycerides | |
| JP4393640B2 (en) | Production of plant sterols | |
| JPS5917120B2 (en) | Method for producing sucrose ester | |
| JP2957273B2 (en) | Purification method of 7-chloro-quinoline-8-carboxylic acid | |
| JPS62142141A (en) | Production of sorbitan oleate | |
| JPH01108990A (en) | Production of oil and fat | |
| SU622817A1 (en) | Method of obtaining 7-dehydrocholesterin | |
| KR0180607B1 (en) | Process for production and purification of sucrose fatty acid esters | |
| SU583128A1 (en) | Method of preparing 4-methoxy-n-methylnaphthalimide | |
| JPH029572B2 (en) | ||
| JPH0291071A (en) | Production of quinacridine-3-methanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |