JPH02194099A - Preparation of high-purity hydroxystearic acid - Google Patents
Preparation of high-purity hydroxystearic acidInfo
- Publication number
- JPH02194099A JPH02194099A JP1482989A JP1482989A JPH02194099A JP H02194099 A JPH02194099 A JP H02194099A JP 1482989 A JP1482989 A JP 1482989A JP 1482989 A JP1482989 A JP 1482989A JP H02194099 A JPH02194099 A JP H02194099A
- Authority
- JP
- Japan
- Prior art keywords
- purity
- hydroxystearic acid
- acid
- oxystearic acid
- castor oil
- 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
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims abstract description 6
- 239000004359 castor oil Substances 0.000 claims abstract description 6
- 235000019438 castor oil Nutrition 0.000 claims abstract description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 6
- 238000000956 solid--liquid extraction Methods 0.000 claims abstract description 6
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract 4
- VLHZUYUOEGBBJB-UHFFFAOYSA-N hydroxy stearic acid Natural products OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 6
- 235000021355 Stearic acid Nutrition 0.000 abstract description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000008117 stearic acid Substances 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- 235000021314 Palmitic acid Nutrition 0.000 abstract description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 240000008570 Digitaria exilis Species 0.000 description 1
- 235000019715 Fonio Nutrition 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- -1 methyl ethyl ketone Chemical compound 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、ヒマシ油より得られるオキシステアリン酸に
有機溶剤を加え、固液抽出を行なう事により、１２−ヒ
ドロキシステアリン酸以外の成分、例えば、バルミチン
酸、ステアリン酸等の不純物を抽出除去し、高純度のオ
キシステアリン酸を得る事にある。Detailed Description of the Invention (Industrial Application Field) The present invention involves adding an organic solvent to oxystearic acid obtained from castor oil and performing solid-liquid extraction to extract components other than 12-hydroxystearic acid, such as The objective is to extract and remove impurities such as valmitic acid and stearic acid to obtain highly pure oxystearic acid.
オキシステアリン酸の純度を上げることにより、油脂類
に対するゲル化力を著しく向上させることができる。By increasing the purity of oxystearic acid, the gelling power for oils and fats can be significantly improved.
〈従来技術及びその問題点）
脂肪酸の一般的な高純度化法としては、精密分留法や分
別結晶法などがある。精密分留法は、高温・減圧下で脂
肪酸く又はその誘導体）を蒸気とし、固有の蒸気圧の差
を利用して精留塔内で分留する方法であり、分別結晶法
は溶剤に対する溶解度の差を利用して結晶を析出させ、
分別する方法であるが、１２−ヒドロキシステアリン酸
（オキシステアリン酸の主成分）の場合は、分子内に水
酸基とカルボキシル基を有しているので、加熱するだけ
で、分子内や分子間でエステル化反応が起こリ、分子内
縮合物や環状ダイマー 分子閉縮合物などの複雑な混合
物が生じ、又ｎ−ヘキサンの様な非極性溶剤、又はメチ
ルエチルケトンの様な中程度の極性溶剤で再結晶を行な
うと弱いゲルを形成し、ろ過不可能な状態となる等の特
性のためにこれらの高純度化法を適用するのは困難であ
った。<Prior Art and its Problems> General methods for high purification of fatty acids include precision fractional distillation and fractional crystallization. The precision fractionation method is a method in which fatty acids (or their derivatives) are converted into vapor at high temperature and reduced pressure, and fractionated in a rectification column using the inherent difference in vapor pressure. Precipitate crystals using the difference in
In the case of 12-hydroxystearic acid (the main component of oxystearic acid), 12-hydroxystearic acid (the main component of oxystearic acid) has a hydroxyl group and a carboxyl group in its molecule, so simply by heating it, esters can be separated within and between molecules. A complex mixture of intramolecular condensates, cyclic dimers, and closed molecular condensates is formed, and recrystallization in non-polar solvents such as n-hexane or moderately polar solvents such as methyl ethyl ketone is necessary. It has been difficult to apply these high purification methods due to characteristics such as forming a weak gel and making it impossible to filter.
（解決手段）
本発明者は、オキシステアリン酸の高純度化法を検討し
た結果、原料オキシステアリン酸に有機溶剤、例えばｎ
−ヘキサン、トルエンなどの炭化水素類、四塩化炭素等
の塩素化炭化水素類、ジエチルエーテルなとのエーテル
類、メチルエチルケトンなどのケトン類、酢酸エチルな
どのエステル類を単独、又は混液として加え、オキシス
テアリン酸を溶解する事なく一１０〜５０℃で固液抽出
を行なうと、オキシステアリン酸中に含まれるパルミチ
ン酸、ステアリン酸、及びその他の不純物が選択的に溶
出する事を発見し、本発明を完成した。(Solution Means) As a result of studying a method for highly purifying oxystearic acid, the present inventor discovered that organic solvents such as n
- Hydrocarbons such as hexane and toluene, chlorinated hydrocarbons such as carbon tetrachloride, ethers such as diethyl ether, ketones such as methyl ethyl ketone, and esters such as ethyl acetate are added alone or as a mixture; It was discovered that when solid-liquid extraction is performed at -10 to 50°C without dissolving stearic acid, palmitic acid, stearic acid, and other impurities contained in oxystearic acid are selectively eluted, and the present invention is based on this discovery. completed.
有機溶剤の添加量は原料オキシステアリン酸が完全に覆
われる量以上であれば良く通常は１〜３倍量（重量比）
である。又、抽出回数は通常１〜５回で、抽出時間は１
０分程度以上であれば良い。原料オキシステアリン酸の
形状やその大きさについては特に限定はしないが、細か
すぎるとろ過に時間がかかり、大きすぎると抽出に時間
がかかるため、好ましくは、長径５−２０ｍｍ、厚さ１
−２ｍｍ程度の薄片が効率良く使用できる。固液抽出は
有機溶剤を添加後、−１０〜５０℃て静置、攪はん又は
液を循環する等の方法により行なう、抽出、ろ過積の残
金は、溶融しない程度の温度で乾燥する。これにより例
えば純度８５．７％、水酸基価１５Ｂ、７、エステル価
４．１の原料オキシステアリン酸から、純度９０％以上
、水酸基価１６５以上、エステル価２．５以下の高純度
オキシステアリン酸が得られる。The amount of organic solvent added should be at least the amount that completely covers the raw material oxystearic acid, and is usually 1 to 3 times the amount (weight ratio).
It is. In addition, the number of extractions is usually 1 to 5 times, and the extraction time is 1 to 5 times.
It is sufficient if the time is about 0 minutes or more. There are no particular restrictions on the shape or size of the raw material oxystearic acid, but if it is too fine, it will take time to filter, and if it is too large, it will take time to extract, so it is preferably 5-20 mm in major axis and 1 in thickness.
- Thin pieces of about 2 mm can be used efficiently. Solid-liquid extraction is carried out by adding an organic solvent and then allowing it to stand at -10 to 50°C, stirring, or circulating the liquid.The residue of the extraction and filtration product is dried at a temperature that does not melt. As a result, for example, high purity oxystearic acid with a purity of 90% or more, a hydroxyl value of 165 or more, and an ester value of 2.5 is obtained from the raw material oxystearic acid with a purity of 85.7%, a hydroxyl value of 15B.7, and an ester value of 4.1. can get.
（オキシステアリン酸の定量法）
試料約５０ｍｇをフラスコにとり、三フッ化ホウ素−メ
タノール試薬１ ｍ ｌを加える。(Method for quantifying oxystearic acid) Approximately 50 mg of a sample is placed in a flask, and 1 ml of boron trifluoride-methanol reagent is added.
冷却器を付けて２分間、沸騰させた後、ｎ −ヘキサン
５ｍｌを冷却器上部から加え、さらに１分間沸騰させる
。加熱を止め、フラスコを冷却器から外し、ｎ−ヘキサ
ン溶液がフラスコの首に達するまで塩化ナトリウム飽和
水溶液を加える。約１ ｍ ｌのｎ−ヘキサン溶液を試
験管に移し、少量の無水硫酸ナトリウムを加えて乾燥し
、試料溶液とする。この液につき、次の条件でガスクロ
マトグラフィーを行ない、保持時間１分以後の各々のピ
ークの合計面積に対する１２−ヒドロキシステアリン酸
のピーク面積百分率を求めこれを純度とすくガスクロマ
トグラフ条件〉
カラム： ＦＯＮＩＯ％ （消和化工（株）製）１
ｍ Ｘ ３ ｍ ｍφ
カラム温度＝ ２４５℃
キャリヤーガス： Ｎ２ ５０ｍ１／ｍｉｎ検出器：
ＦＩＤ
注入量＝ ２μｌ
以下に本発明の実施例を示す。After boiling for 2 minutes with a condenser attached, 5 ml of n-hexane was added from the top of the condenser and boiled for another minute. Turn off the heat, remove the flask from the condenser, and add saturated aqueous sodium chloride solution until the n-hexane solution reaches the neck of the flask. Transfer about 1 ml of the n-hexane solution to a test tube, add a small amount of anhydrous sodium sulfate, dry it, and use it as a sample solution. This liquid was subjected to gas chromatography under the following conditions, and after a retention time of 1 minute, the peak area percentage of 12-hydroxystearic acid was calculated based on the total area of each peak, and this was determined as purity. Gas chromatography conditions> Column: FONIO % (manufactured by Saewa Kako Co., Ltd.) 1
m x 3 m mφ Column temperature = 245°C Carrier gas: N2 50ml/min Detector:
FID injection volume = 2 μl Examples of the present invention are shown below.
実施例−１
原料オキシステアリン酸（純度８５．７％、水酸基価１
５Ｂ、７、エステル価４．１）１００ｇを５００ ｍ
ｌのビーカーにとり、これに１２０ｇのｎ−ヘキサンを
加え、３５℃にて１時間放置後、ろ過をする。得られた
残金を風乾し、高純度オキシステアリン酸８５．２ｇを
得た。この物の純度をガスクロマトグラフ法により定量
した結果は９３．９％であった。又、水酸基価は１７Ｂ
、６、エステル価は０．９５であった。Example-1 Raw material oxystearic acid (purity 85.7%, hydroxyl value 1
5B, 7, ester value 4.1) 100g to 500m
120 g of n-hexane was added to this, and after standing at 35° C. for 1 hour, it was filtered. The obtained residue was air-dried to obtain 85.2 g of high purity oxystearic acid. The purity of this product was determined by gas chromatography and was 93.9%. Also, the hydroxyl value is 17B
, 6, and the ester value was 0.95.
実施例−２
原料オキシステアリン酸（純度８５．７％、水酸基価１
５Ｂ、７、エステル価４．１）１００ｇを５００ｍ１の
ビーカーにとり、これに２００ｇのジエチルエーテルを
加え、５℃にて３時閏攪はん、以下実施例１と同様に操
作し、高純度オキシステアリン＠８０．６ｇを得た。こ
の物は純度９７．２％、水酸基価１７５．８、エステル
価０．８９であった。Example-2 Raw material oxystearic acid (purity 85.7%, hydroxyl value 1
5B, 7, ester value 4.1) 100g was placed in a 500ml beaker, 200g of diethyl ether was added thereto, and the mixture was interstitially stirred at 5°C for 3 hours. Stearin@80.6g was obtained. This product had a purity of 97.2%, a hydroxyl value of 175.8, and an ester value of 0.89.
実施例−３
原料オキシステアリン酸（純度８６．６％、水酸基価１
５Ｂ、２、エステル価４．７）１００ｇを５００ ｍ
ｌのビーカーにとり、これに１５０ｇのメチルエチルケ
トンを加え、２０〜２８℃で２４時間放置後、ろ過する
。残金を先のビーカーにもどしこれに１６０ｇのｎ−ヘ
キサンを添加し、再度同様の操作を行なった後風乾し、
高純度オキシステアリン酸７６．７ｇを得た。この物は
純度９９．０％、水酸基価１７９．３、エステル価０．
４４であった。Example-3 Raw material oxystearic acid (purity 86.6%, hydroxyl value 1
5B, 2, ester value 4.7) 100g to 500m
150 g of methyl ethyl ketone was added to this, and after standing at 20 to 28° C. for 24 hours, it was filtered. Return the remaining money to the beaker, add 160g of n-hexane to it, repeat the same operation, and air dry.
76.7 g of high purity oxystearic acid was obtained. This product has a purity of 99.0%, a hydroxyl value of 179.3, and an ester value of 0.
It was 44.
実施例−４
原料オキシステアリン酸く純度８６．６％、水酸基価１
５８．２、エステル価４．７）５０ｇを５００ｍ１のビ
ーカーにとり、これに３００ｇのｎ−へブタン・酢酸エ
チル等容量混合液を加え、２３℃で２時間液を循環させ
て抽出する。以下実施例１と同様に操作し、高純度オキ
システアリン酸４１．３ ｇを得た。Example-4 Raw material oxystearic acid, purity 86.6%, hydroxyl value 1
58.2, ester value 4.7) in a 500 ml beaker, add 300 g of an equal volume mixture of n-hebutane and ethyl acetate, and extract by circulating the liquid at 23°C for 2 hours. Thereafter, the same procedure as in Example 1 was carried out to obtain 41.3 g of high purity oxystearic acid.
この物は純度９５．４％、水酸基価１７６．１、エステ
ル価１．２であった。This product had a purity of 95.4%, a hydroxyl value of 176.1, and an ester value of 1.2.
比較例−１
原料オキシステアリン酸（純度８５．７％、水酸基価１
５Ｂ、７、エステル価４．１）１００ｇを２Ｌのビーカ
ーにとり、ｎ−へブタン４００ ｍ ｌを加えて溶かし
た後、５５℃に保ちながら７０％（重１）メタノール水
溶液４００ｇで１回２００ｇで４回抽出を行なう。Comparative Example-1 Raw material oxystearic acid (purity 85.7%, hydroxyl value 1
Take 100 g of 5B, 7, ester value 4.1) in a 2 L beaker, add 400 ml of n-hebutane to dissolve it, and add 400 g of a 70% (weight 1) aqueous methanol solution at 200 g at a time while keeping it at 55°C. Perform four extractions.
抽出液は合わせて、減圧下で溶剤を留去しオキシステア
リン酸６７．６ｇを得た。この物は純度８８．２％、水
酸基価１Ｂ４．２、エステル価１２．５であった。The extracts were combined and the solvent was distilled off under reduced pressure to obtain 67.6 g of oxystearic acid. This product had a purity of 88.2%, a hydroxyl value of 1B4.2, and an ester value of 12.5.
以上、本発明により得られるオキシステアリン酸は比較
例にくらべて高純度であることが判る。As described above, it can be seen that the oxystearic acid obtained by the present invention has a higher purity than that of the comparative example.
Claims (1)
接触還元して得られるオキシステアリン酸に有機溶剤を
加えて固液抽出を行ない、水酸基価が１６５以上、エス
テル価２．５以下、及び１２−ヒドロキシステアリン酸
の含量が９０％以上のオキシステアリン酸を得る事を特
徴とするオキシステアリン酸の高純度化法。[Claims] Castor oil or a derivative thereof is subjected to catalytic reduction and then hydrolyzed, or after hydrolyzing castor oil,
An organic solvent is added to oxystearic acid obtained by catalytic reduction and solid-liquid extraction is performed to obtain oxystearic acid with a hydroxyl value of 165 or more, an ester value of 2.5 or less, and a 12-hydroxystearic acid content of 90% or more. A method for highly purifying oxystearic acid characterized by obtaining the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1482989A JPH02194099A (en) | 1989-01-24 | 1989-01-24 | Preparation of high-purity hydroxystearic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1482989A JPH02194099A (en) | 1989-01-24 | 1989-01-24 | Preparation of high-purity hydroxystearic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02194099A true JPH02194099A (en) | 1990-07-31 |
Family
ID=11871929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1482989A Pending JPH02194099A (en) | 1989-01-24 | 1989-01-24 | Preparation of high-purity hydroxystearic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02194099A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006274156A (en) * | 2005-03-30 | 2006-10-12 | Kao Corp | Manufacturing method of high purity anion surfactant powder (bead) |
| CN110386872A (en) * | 2018-04-16 | 2019-10-29 | 希锐科技(武汉)有限公司 | A kind of refining methd of 12- hydroxy stearic acid or its ester |
-
1989
- 1989-01-24 JP JP1482989A patent/JPH02194099A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006274156A (en) * | 2005-03-30 | 2006-10-12 | Kao Corp | Manufacturing method of high purity anion surfactant powder (bead) |
| CN110386872A (en) * | 2018-04-16 | 2019-10-29 | 希锐科技(武汉)有限公司 | A kind of refining methd of 12- hydroxy stearic acid or its ester |
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