JPH0631395B2 - Refining method of oily substances - Google Patents
Refining method of oily substancesInfo
- Publication number
- JPH0631395B2 JPH0631395B2 JP24495586A JP24495586A JPH0631395B2 JP H0631395 B2 JPH0631395 B2 JP H0631395B2 JP 24495586 A JP24495586 A JP 24495586A JP 24495586 A JP24495586 A JP 24495586A JP H0631395 B2 JPH0631395 B2 JP H0631395B2
- Authority
- JP
- Japan
- Prior art keywords
- oily substance
- hydroxyapatite
- free fatty
- oily substances
- refining method
- 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
- 239000000126 substance Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 21
- 238000007670 refining Methods 0.000 title 1
- 150000002978 peroxides Chemical class 0.000 claims description 16
- 235000021588 free fatty acids Nutrition 0.000 claims description 10
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 9
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 9
- 239000003463 adsorbent Substances 0.000 claims description 7
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 11
- 238000000746 purification Methods 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940057995 liquid paraffin Drugs 0.000 description 5
- 239000004006 olive oil Substances 0.000 description 5
- 235000008390 olive oil Nutrition 0.000 description 5
- 238000004042 decolorization Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008159 sesame oil Substances 0.000 description 4
- 235000011803 sesame oil Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000001877 deodorizing effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010517 refined sesame oil Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910014497 Ca10(PO4)6(OH)2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 239000000853 adhesive Substances 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052587 fluorapatite Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 239000010464 refined olive oil Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Fats And Perfumes (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は油性物質の精製法に関する。更に詳しくは、油
性物質に含有される遊離脂肪酸および／または過酸化物
を除去するためにハイドロキシアパタイトを用いること
を特徴とする油性物質の精製法に関する。尚、本発明で
いう油性物質とは、動植物あるいは鉱物から採取される
グリセリド、ワックスエステル、炭化水素油など、およ
び合成油を含むものとする。TECHNICAL FIELD The present invention relates to a method for purifying an oily substance. More specifically, it relates to a method for purifying an oily substance, characterized in that hydroxyapatite is used to remove free fatty acids and / or peroxides contained in the oily substance. The oily substance as used in the present invention includes glycerides, wax esters, hydrocarbon oils and the like collected from animals and plants or minerals, and synthetic oils.
［従来の技術］ 動植物や鉱物から採取された原油は種々の不純物を含ん
でいる。これら不純物の中には、油性物質を着色させた
り、発煙させたり、変臭を生じさせたり、泡立ちの原因
となったり、味を悪くしたり、あるいは生体に対する毒
性や刺激の原因となるものが含まれている。このため、
工業的には油性物質の精製が行なわれている。[Prior Art] Crude oil collected from animals and plants and minerals contains various impurities. Among these impurities, some may cause coloring of oily substances, smoking, causing odor, causing foaming, bad taste, or causing toxicity or irritation to the living body. include. For this reason,
Oily substances are industrially refined.
例えば、食用油脂の精製は蛋白質分解物や粘質物を除く
脱ガム工程、遊離脂肪酸を取り除く脱酸工程、着色の原
因となる色素などを除く脱色工程、不快な臭いの原因と
なる酸化生成物を除く脱臭工程がとられている。これら
の過程で吸着剤が用いられるのは脱色工程であるが、そ
の場合の吸着剤としては酸性白土、活性白土、活性炭、
活性アルミナ、ベントナイトなどが使用されている。ま
た、合成油の場合にも蒸留後、脱色、脱臭のために同様
の吸着剤が使用される。For example, edible oils and fats are purified by degumming process to remove proteolytic products and mucilages, deoxidation process to remove free fatty acids, decolorization process to remove pigments that cause coloring, and oxidation products that cause unpleasant odors. The deodorizing process to remove is taken. The adsorbent is used in these processes in the decolorization step, but in that case, as the adsorbent, acid clay, activated clay, activated carbon,
Activated alumina and bentonite are used. Also in the case of synthetic oil, the same adsorbent is used for decolorization and deodorization after distillation.
［発明が解決しようとする問題点］ しかしながら、前記した精製工程を経たとしても、油性
物質から遊離脂肪酸や過酸化物を完全に除去することは
難しく、それらの残存不純物を足がかりとして、さらに
油性物質の劣化が進行する。その結果、変臭、色の戻
り、揚油の発煙、揚物の品質低下、生体に対する毒性や
刺激性の発現など食品、医薬品、化粧品、クレヨン、光
沢剤といったさまざまな分野で実用上の問題点を引き起
こす。このため、油性物質から微量の遊離脂肪酸および
／または過酸化物を除去することは重要な問題である。[Problems to be Solved by the Invention] However, it is difficult to completely remove free fatty acids and peroxides from the oily substance even after the above-mentioned purification step, and the residual impurities are used as a foothold to further remove the oily substance. Deterioration progresses. As a result, it causes practical problems in various fields such as food, pharmaceuticals, cosmetics, crayons, brighteners, etc. such as foul odor, color return, frying of frying oil, deterioration of frying quality, expression of toxicity and irritation to living body. . For this reason, the removal of traces of free fatty acids and / or peroxides from oily substances is an important issue.
［問題点を解決するための手段］ 本発明者等は、こうした従来技術の事情に鑑み、遊離脂
肪酸および過酸化物に対して特異的な吸着能を有する吸
着剤を開発すべく研究を重ねてきたが、今般、リン酸カ
ルシウムの一種であるハイドロキシアパタイトが油性物
質の遊離脂肪酸および過酸化物を選択的に吸着すること
を見出し、この知見に基づいて本発明を完成するに至っ
た。すなわち、本発明は油性物質に含有される遊離脂肪
酸および／または過酸化物を除去する工程において、ハ
イドロキシアパタイトを用いることを特徴とする油性物
質の精製法を提供するものである。[Means for Solving Problems] In view of the circumstances of the prior art, the present inventors have conducted extensive research to develop an adsorbent having a specific adsorption capacity for free fatty acids and peroxides. However, recently, it was found that hydroxyapatite, which is a kind of calcium phosphate, selectively adsorbs free fatty acids and peroxides of an oily substance, and the present invention has been completed based on this finding. That is, the present invention provides a method for purifying an oily substance, which comprises using hydroxyapatite in the step of removing free fatty acid and / or peroxide contained in the oily substance.
本発明において使用されるハイドロキシアパタイトは鉱
物名で、その化学式はCa10(PO4)6(OH)2で表され、脊椎
動物の骨格を構成する無機成分としても知られている。
天然に産するアパタイト鉱物はほとんどがフッ素アパタ
イトCa10(PO4)6F2であるため、通常ハイドロキシアパタ
イトは、例えば以下のような湿式法あるいは乾式法によ
って合成される。湿式法による合成の一例を挙げれば、
水酸化カルシウムとリン酸を水溶液中で室温から60℃程
度の温度で反応させてハイドロキシアパタイト粉末を得
る。一方、乾式法による合成の一例を挙げると、炭酸カ
ルシウムとリン酸カルシウムを空気中あるいは水蒸気雰
囲気中で900〜1200℃の高温下で固相反応によりハイド
ロキシアパタイト粉末を得る。吸着剤は比表面積が大き
い方が好ましいので、より微粒子の得られる湿式方によ
る合成方が好ましい。また得られたハイドロキシアパタ
イト粉末を焼成して用いることもできる。Hydroxyapatite used in the present invention is a mineral name, and its chemical formula is represented by Ca 10 (PO 4 ) 6 (OH) 2 and is also known as an inorganic component constituting a vertebrate skeleton.
Since most of the naturally occurring apatite minerals are fluoroapatite Ca 10 (PO 4 ) 6 F 2 , hydroxyapatite is usually synthesized by the wet method or dry method as described below. To give an example of the synthesis by the wet method,
Hydroxyapatite powder is obtained by reacting calcium hydroxide and phosphoric acid in an aqueous solution at a temperature from room temperature to about 60 ° C. On the other hand, as an example of the synthesis by the dry method, hydroxyapatite powder is obtained by solid phase reaction of calcium carbonate and calcium phosphate in air or in a steam atmosphere at a high temperature of 900 to 1200 ° C. Since it is preferable that the adsorbent has a large specific surface area, it is preferable to use a wet method for synthesizing fine particles. Further, the obtained hydroxyapatite powder can be used after being calcined.
本発明の油性物質の精製法は、従来の精製工程である脱
ガム、脱酸、脱色、脱臭工程、あるいは一般的な蒸留工
程を行った後、ハイドロキシアパタイトを吸着剤として
使用して最終的に高度な精製を行うと効果的である。そ
の結果、油性物質に含有される遊離脂肪酸や過酸化物が
除去される。この際、従来知られているハイドロキシア
パタイトの吸着能（蛋白質吸着能、陽イオン、フッ素交
換能等）も作用することはいうまでもない。その方法と
して、油性物質を有機溶剤に溶解し、ハイドロキシアパ
タイト粉末を充填した吸着塔に通して不純物を吸着させ
た後、流出液から精製油性物質を得る方法、油性物質の
中にハイドロキシアパタイト粉末を添加、分散し不純物
を吸着させた後、濾過によって精製油性物質を得る方
法、ハイドロキシアパタイト粉末を成型し、焼成した多
孔質焼結体をフィルターとして用い、そこに油性物質を
通し精製する方法などがある。The purification method of the oily substance of the present invention is a conventional purification step such as degumming, deoxidation, decolorization, deodorizing step, or general distillation step, and finally using hydroxyapatite as an adsorbent. It is effective to perform a high degree of purification. As a result, free fatty acids and peroxides contained in the oily substance are removed. In this case, needless to say, the conventionally known adsorption ability of hydroxyapatite (protein adsorption ability, cation, fluorine exchange ability, etc.) also acts. As its method, an oily substance is dissolved in an organic solvent, and after adsorbing impurities through an adsorption tower filled with hydroxyapatite powder, a method of obtaining a purified oily substance from the effluent, a hydroxyapatite powder in the oily substance After adding, dispersing and adsorbing impurities, there is a method of obtaining a purified oily substance by filtration, a method of molding hydroxyapatite powder and using a fired porous sintered body as a filter, and purifying the oily substance by passing therethrough. is there.
［効果］ このようにして得られる油性物質は、不純物として含有
される遊離脂肪酸や過酸化物が高度に精製され、今まで
の方法によって精製された油性物質に比べて、におい、
色の戻り、揚物の品質低下、生体に対する毒性や刺激
性、また経時での安定性などが著しく改良される。[Effect] The oily substance thus obtained has a scent that is higher than that of the oily substance refined by the conventional methods because the free fatty acids and peroxides contained as impurities are highly purified,
Color reversion, deterioration of the quality of frying, toxicity and irritation to living organisms, and stability over time are remarkably improved.
［実施例］ 次に実施例を挙げて本発明をさらに詳しく説明するが、
本発明の技術的範囲をこれらの実施例に限定するもので
はないことはいうまでもない。EXAMPLES Next, the present invention will be described in more detail with reference to Examples.
It goes without saying that the technical scope of the present invention is not limited to these examples.
実施例１ ハイドロキシアパタイト粉末100部を吸着塔に充填し、
ｎ−ヘキサン40部にオリーブ油（日本油脂製）20部を溶
解した液を上記吸着塔に通し、さらにｎ−ヘキサン100
部を流出した後、流出液からｎ−ヘキサンを留去して精
製オリーブ油を得た。このオリーブ油の過酸化物値をヨ
ウ素滴定法により測定した結果、もとのオリーブ油の過
酸化物価が14.3meq／kgであったのに対し、ハイドロキ
シアパタイトの吸着塔を通したオリーブ油の過酸化物価
は０であった。この精製オリーブ油はにおいがなく、経
時での安定性も著しく向上した。Example 1 An adsorption tower was filled with 100 parts of hydroxyapatite powder,
A liquid obtained by dissolving 20 parts of olive oil (made by NOF CORPORATION) in 40 parts of n-hexane was passed through the adsorption tower, and then n-hexane 100 was added.
After flowing out of the solution, n-hexane was distilled off from the effluent to obtain a purified olive oil. As a result of measuring the peroxide value of this olive oil by the iodometric titration method, the peroxide value of the original olive oil was 14.3 meq / kg, whereas the peroxide value of the olive oil passed through the adsorption tower of hydroxyapatite was It was 0. This refined olive oil had no odor and the stability over time was significantly improved.
実施例２ ゴマ油100部に対し、10部のハイドロキシアパタイト粉
末を添加し、10時間分散後、濾過により精製したゴマ油
を得た。もとのゴマ油の酸価が0.2であったのに対し、
精製ゴマ油の酸価は０であった。また実施例１と同じ方
法で過酸化物価を測定した結果、もとの価が30.2meq／k
gであったのに対し、精製ゴマ油の過酸化物価は０であ
った。この精製ゴマ油は風味にすぐれ、経時での安定性
も著しく向上した。Example 2 10 parts of hydroxyapatite powder was added to 100 parts of sesame oil, dispersed for 10 hours, and then sesame oil purified by filtration was obtained. Whereas the original sesame oil had an acid value of 0.2,
The acid value of the refined sesame oil was 0. Moreover, as a result of measuring the peroxide value by the same method as in Example 1, the original value was 30.2 meq / k.
The sesame oil, however, had a peroxide value of 0. This refined sesame oil had excellent flavor and significantly improved stability over time.
実施例３ ハイドロキシアパタイト粉末100部をプレスし、1000〜1
250℃で焼成した焼成体をフィルターとして用い、これ
に流動パラフィン100部を通過させた。もとの流動パラ
フィンの過酸化物価は115meq／kgであったのに対し、濾
過した流動パラフィンの過酸化物価は０であった。精製
前と精製後の流動パラフィンをウサギ皮膚に繰返し塗布
試験を行った結果、精製前の流動パラフィンは皮膚刺激
性が認められたが、精製後のものは認められなかった。Example 3 100 parts of hydroxyapatite powder was pressed to 1000-1
The calcined product calcined at 250 ° C. was used as a filter, and 100 parts of liquid paraffin was passed through the filter. The original liquid paraffin had a peroxide value of 115 meq / kg, whereas the filtered liquid paraffin had a peroxide value of 0. As a result of repeatedly applying the liquid paraffin before and after purification to rabbit skin, the liquid paraffin before purification showed skin irritation, but did not after purification.
フロントページの続き (56)参考文献 実開 昭59−70734（ＪＰ，Ｕ) 特表 昭58−501950（ＪＰ，Ａ)Continuation of front page (56) Bibliographic references Sho 59-70734 (JP, U) Special table Sho 58-501950 (JP, A)
Claims (1)
または過酸化物を吸着除去する工程において、吸着剤と
してハイドロキシアパタイトを用いることを特徴とする
油性物質の精製法。1. Free fatty acid and / or contained in oily substance
Alternatively, a method for purifying an oily substance, wherein hydroxyapatite is used as an adsorbent in the step of adsorbing and removing the peroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24495586A JPH0631395B2 (en) | 1986-10-15 | 1986-10-15 | Refining method of oily substances |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24495586A JPH0631395B2 (en) | 1986-10-15 | 1986-10-15 | Refining method of oily substances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6397696A JPS6397696A (en) | 1988-04-28 |
| JPH0631395B2 true JPH0631395B2 (en) | 1994-04-27 |
Family
ID=17126438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24495586A Expired - Lifetime JPH0631395B2 (en) | 1986-10-15 | 1986-10-15 | Refining method of oily substances |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0631395B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2743178B2 (en) * | 1988-06-14 | 1998-04-22 | 株式会社アドバンス | How to use adsorbent for lipid |
| JP2014121297A (en) * | 2012-12-21 | 2014-07-03 | Yuko Moriyama | Edible oil |
| EP3487959A4 (en) * | 2016-07-25 | 2020-02-19 | The Governors of the University of Alberta | METHOD FOR PRODUCING HYDROCARBON COMPOSITIONS WITH A REDUCED NUMBER OF ACID AND FOR INSULATING SHORT-CHAIN FATTY ACIDS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5770734U (en) * | 1980-10-15 | 1982-04-28 |
-
1986
- 1986-10-15 JP JP24495586A patent/JPH0631395B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6397696A (en) | 1988-04-28 |
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