JPS6210040A - Production of aryl fatty acid - Google Patents

Production of aryl fatty acid

Info

Publication number
JPS6210040A
JPS6210040A JP60149250A JP14925085A JPS6210040A JP S6210040 A JPS6210040 A JP S6210040A JP 60149250 A JP60149250 A JP 60149250A JP 14925085 A JP14925085 A JP 14925085A JP S6210040 A JPS6210040 A JP S6210040A
Authority
JP
Japan
Prior art keywords
acid
unsaturated fatty
aryl
fatty acids
activated clay
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.)
Granted
Application number
JP60149250A
Other languages
Japanese (ja)
Other versions
JPH0260654B2 (en
Inventor
Hitoshi Kobashi
小橋　仁
Yoshihito Kadoma
義仁 門磨
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NOF Corp
Original Assignee
Nippon Oil and Fats Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd
Priority to JP60149250A priority Critical patent/JPS6210040A/en
Publication of JPS6210040A publication Critical patent/JPS6210040A/en
Publication of JPH0260654B2 publication Critical patent/JPH0260654B2/ja
Granted legal-status Critical Current

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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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

PURPOSE:To obtain the titled compound useful as an antioxidant and an anticorrosion agent, etc., in high quality and purity, by using an oxyacid of phosphorus in combination with active clay used as a catalyst in the addition reaction of an aryl compound and an unsaturated fatty acid, thereby improving the catalytic effect of the clay. CONSTITUTION:The objective compound can be produced by the addition reaction of an aryl compound and an unsaturated fatty acid in the presence of a catalyst consisting of 1-12wt% (based on the unsaturated fatty acid) active clay and 0.05-0.75wt% oxyacid of phosphorus, in an autoclave at 125-225 deg.C, preferably 160-200 deg.C. It is preferable to use the aryl compound in excess to the unsaturated fatty acid to complete the reaction, and distill off the excess aryl compound after the reaction. The oxyacid of phosphorus is hypophosphorous acid, pyrophosphoric acid, etc., and is used as it is or in the form of aqueous solution.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明はアリール化合物と不飽和脂肪酸類との付加反応
に関し、詳しくは触媒として活性白土とリンの酸素酸と
を用いるアリール脂肪酸の製造法である。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an addition reaction between an aryl compound and an unsaturated fatty acid, and more specifically, a method for producing an aryl fatty acid using activated clay and a phosphorus oxygen acid as a catalyst. be.

〔従来の技術〕[Conventional technology]

不飽和脂肪酸類に、フェノール、クレゾール、アニソー
ル、ベンゼン、トルエンなどのアリール化合物を付加し
て得られるアリール脂肪酸は、抗酸化剤、腐食防止剤な
どとして巾広く用いられている。このアリール脂肪酸を
得るアリール化合物と不飽和脂肪酸類との付加反応に際
しては、従来触媒として塩化アルミニウム、硫酸、メタ
ンスルホン酸、強酸性イオン交換樹脂などの酸触媒が用
いられている。塩化アルミニウム、硫酸およびメタンス
ルホン酸の場合には触媒の分離が困難であったり、装置
の腐食の原因となるばかりでなく、副反応が起こりやす
く、また強酸性イオン交換樹脂の場合には付加化合物の
収率が低いといった問題点がある。Aryl fatty acids obtained by adding aryl compounds such as phenol, cresol, anisole, benzene, and toluene to unsaturated fatty acids are widely used as antioxidants, corrosion inhibitors, and the like. In addition reactions between aryl compounds and unsaturated fatty acids to obtain aryl fatty acids, acid catalysts such as aluminum chloride, sulfuric acid, methanesulfonic acid, and strongly acidic ion exchange resins have conventionally been used as catalysts. In the case of aluminum chloride, sulfuric acid, and methanesulfonic acid, it is difficult to separate the catalyst, which not only causes corrosion of the equipment, but also tends to cause side reactions, and in the case of strongly acidic ion exchange resins, it may cause addition compounds. There is a problem that the yield is low.

フェノールに代表されるヒドロキシアリール化合物と不
飽和脂肪酸類との付加化合物を製造するに際して触媒と
して活性白土を使用することが特公昭４１−６５８１号
公報に示されている。この特許公報において使用されて
いる活性白土はアメリカ会衆国産の活性白土であり、日
本国内産の活性白土を用いて公報の記載に準じて実験を
行った場合には付加化合物を収率良く得ることができな
い。活性白土は天然の鉱物質を原料としており、産地お
よび成分組成の差によって触媒活性が異なシ、特に日本
国内産活性白土の触媒活性の低いことが知られている。Japanese Patent Publication No. 41-6581 discloses the use of activated clay as a catalyst in producing addition compounds of hydroxyaryl compounds such as phenol and unsaturated fatty acids. The activated clay used in this patent publication is a domestically produced activated clay produced in the United States, and when an experiment is conducted using activated clay produced in Japan according to the description in the publication, the addition compound can be obtained in good yield. I can't. Activated clay is made from natural minerals, and its catalytic activity varies depending on the region of production and the composition of the ingredients, and it is known that activated clay produced in Japan has particularly low catalytic activity.

また、ヒドロキシアリール化合物と不飽和脂肪酸類との
付加反応圧際し、活性白土とパラトルエンスルホン酸と
を用いて、常圧下で反応する方法が特公昭５０−５７０
４号公報に開示されている。In addition, during the addition reaction between hydroxyaryl compounds and unsaturated fatty acids, a method of reacting under normal pressure using activated clay and para-toluenesulfonic acid was published in Japanese Patent Publication No. 50-570.
It is disclosed in Publication No. 4.

この方法においては活性白土の使用量が不飽和脂肪酸類
に対して５〜２５係と多いために、得られたヒドロキシ
アリール脂肪酸の活性白土への付着ロスが著しいだけで
なく、活性白土の分離に余分な時間を必要として経済的
な方法ではない。そのうえ、常圧下で反応を行うために
水分の蒸発が起こり、フェノールと脂肪酸とのエステル
が生成して反応生成物中のヒドロキシアリール脂肪酸の
純度が低いものとなる。In this method, since the amount of activated clay used is 5 to 25 times higher than that of unsaturated fatty acids, not only is there a significant loss of adhesion of the obtained hydroxyaryl fatty acids to the activated clay, but also the separation of the activated clay is difficult. It is not an economical method as it requires extra time. Moreover, since the reaction is carried out under normal pressure, water evaporates and esters of phenol and fatty acids are produced, resulting in a low purity hydroxyaryl fatty acid in the reaction product.

さらに、活性白土と炭素数８以上の炭化水素基をもつス
ルホン酸とを用いるアリール脂肪酸の製造法について本
発明者らが提案している（特願昭５９−１７３４２０号
）。この方法においてはアリール脂肪酸を高収率で得る
ことができるが、生成したアリール脂肪酸から炭素数８
以上の炭化水素基をもつスルホン酸の分離が困難であり
、得られたアリール脂肪酸の色相が濃色である。特に、
スルホン酸基をもつ化合物がアリール脂肪酸中に微量で
も残存すると、そのアリール脂肪酸を利用した誘導体の
品質が悪くなり好ましくない。Furthermore, the present inventors have proposed a method for producing aryl fatty acids using activated clay and a sulfonic acid having a hydrocarbon group having 8 or more carbon atoms (Japanese Patent Application No. 173,420/1982). In this method, aryl fatty acids can be obtained in high yield, but the aryl fatty acids produced have 8 carbon atoms.
It is difficult to separate sulfonic acids having the above hydrocarbon groups, and the obtained aryl fatty acid has a dark hue. especially,
If even a trace amount of a compound having a sulfonic acid group remains in the aryl fatty acid, the quality of the derivative using the aryl fatty acid deteriorates, which is not preferable.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

アリール化合物と不飽和脂肪酸類との付加反応の触媒と
して、触媒活性の低いとされる日本国内産活性白土を用
いて、アリール脂肪酸を高純度、高収率で得ようとする
ものである。The aim is to obtain aryl fatty acids with high purity and high yield by using activated clay produced in Japan, which is said to have low catalytic activity, as a catalyst for addition reactions between aryl compounds and unsaturated fatty acids.

さらに、活性白土の触媒活性を高めるために併用する酸
性成分が残存しない淡色々アリール脂肪酸を得ることも
目的としている。Furthermore, the aim is to obtain a variety of light aryl fatty acids in which no acidic components remain, which are used in combination to enhance the catalytic activity of activated clay.

〔問題点を解決するだめの手段〕[Failure to solve the problem]

本発明は、微量のある種の鉱酸を少量の活性白土と組合
せて使用すれば、国内産、外国産を問わず、また活性白
土の種類に関係なくアリール脂肪酸が効率よく得られる
ことを゛見出して完成されたもので、市販の活性白土の
使用で十分な効果を発揮する。The present invention shows that by using a trace amount of a certain type of mineral acid in combination with a small amount of activated clay, aryl fatty acids can be efficiently obtained regardless of whether it is domestically produced or foreign, and regardless of the type of activated clay. It was discovered and perfected, and it is fully effective when used with commercially available activated clay.

本発明は、アリール化合物と不飽和脂肪酸類との付加反
応に際し、触媒として不飽和脂肪酸類に対して１〜１２
重量％の活性白土と０．０５〜０．７５重量％のリンの
酸素酸とを用いることを特徴とするアリール脂肪酸の製
造法である。In the addition reaction between an aryl compound and an unsaturated fatty acid, the present invention uses 1 to 12
This is a method for producing aryl fatty acids characterized by using 0.05 to 0.75 weight % of activated clay and 0.05 to 0.75 weight % of phosphorus oxyacid.

本発明において用いられるアリール化合物としては、ベ
ンゼン、トルエン、ナフタリン、アニソール、フェノー
ル、クレゾール、ナフトールあるいはそれらの核置換化
合物などがある。Aryl compounds used in the present invention include benzene, toluene, naphthalene, anisole, phenol, cresol, naphthol, and nuclear substituted compounds thereof.

本発明における不飽和脂肪酸類とは、不飽和脂肪酸およ
びその１価ないし２：１ｌＩｉ以上の多価アルコールエ
ステルをいい、不飽和′脂肪酸としては炭素数８以上の
不飽和酸であればよく、二重結合の数も１つとは限らず
、パルミトレイン・浚、オレイン酸、エライジン酸、リ
ノール酸、リルン酸、エルカ酸など各種のものがある。The unsaturated fatty acids in the present invention refer to unsaturated fatty acids and their monohydric to 2:1lIi or higher polyhydric alcohol esters, and the unsaturated fatty acids may be any unsaturated acids having 8 or more carbon atoms; The number of double bonds is not limited to one, and there are various types such as palmitoleic acid, oleic acid, elaidic acid, linoleic acid, lylunic acid, and erucic acid.

本発明において用いることのできる活性白土としては、
とく（モンモリロナイト、ハｐイサイト、セピオライト
、アタパルジャイトなどを主成分とする日本国内産活性
白土が適している。活性白土の使用量は不飽和脂肪−稜
類に対して１〜１２重量％が好ましい。活性白土の使用
量は少ないほうが望ましいが、１重ｔ　％より少量では
その触媒効果が不十分である。また、１２重量％より多
量に活性白土を使用しても反応の転化率は向上しないし
、生成物の回収ロスが増大して経済的でない。Activated clay that can be used in the present invention includes:
Activated clay produced in Japan containing montmorillonite, hapisite, sepiolite, attapulgite, etc. as a main component is suitable. The amount of activated clay used is preferably 1 to 12% by weight based on the unsaturated fat-like substances. It is desirable to use a smaller amount of activated clay, but if it is less than 1% by weight, the catalytic effect will be insufficient.Also, if activated clay is used in an amount greater than 12% by weight, the conversion rate of the reaction will not improve. , the loss of product recovery increases, making it uneconomical.

本発明において用いられるリンの酸素酸としてｉよ、次
亜リン酸、亜リン酸、次リン酸、リン酸、ピロリン酸、
メタリン酸、ポリリン酸などがあげられる。これらのリ
ンの酸素酸はそのものを用いてもよいし、水溶液にして
用いることもできる。The phosphorous oxygen acids used in the present invention include hypophosphorous acid, phosphorous acid, hypophosphoric acid, phosphoric acid, pyrophosphoric acid,
Examples include metaphosphoric acid and polyphosphoric acid. These phosphorus oxyacids may be used as such or may be used in the form of an aqueous solution.

リンの酸素酸の使用量は、不飽和脂肪酸類に対して０．
０５〜０．７．５重量％が好ましく、これより少ない量
では触媒効果が少なく、また、これより多く使用しても
反応の転化率は向上しないばかりでなく、生成したアリ
ール脂肪酸中にリン化合物が残存するようになり好まし
くない。The amount of phosphorus oxygen acid used is 0.0% relative to unsaturated fatty acids.
05 to 0.7.5% by weight is preferable; if the amount is less than this, the catalytic effect will be low, and if the amount is more than this, the conversion rate of the reaction will not improve, and the phosphorus compound will not be present in the produced aryl fatty acid. remains, which is undesirable.

本発明の７リール脂肪酸の製造法は、活性白土とリンの
＋Ｊ素酸とを触媒として７リ一ル化合物と不飽和脂肪酸
類をオートクレーブ中にて１２５〜２２５Ｃ，好ましく
は１６０〜２００Ｃに加熱して反応させるものである。The method for producing 7-lyl fatty acids of the present invention involves heating a 7-lyl compound and unsaturated fatty acids in an autoclave to 125-225C, preferably 160-200C using activated clay and phosphorus +J basic acid as catalysts. The reaction is caused by a reaction.

反応に際してアリール化合物を不飽和脂肪酸類に対して
過剰に用いて反応を完結させ、反応終了後に過剰の７リ
一ル化合物を留去することが好ましい。It is preferable that the aryl compound is used in excess of the unsaturated fatty acid during the reaction to complete the reaction, and that the excess 7lyl compound is distilled off after the reaction is completed.

〔発明の効果〕〔Effect of the invention〕

本発明の方法においては、リンの酸素酸を使用したこと
により、活性白土の触媒効果を高めて高品質の７リール
脂肪酸を高純度だ得ることができる。In the method of the present invention, by using phosphorus oxyacid, the catalytic effect of activated clay can be enhanced, and high-quality 7-reel fatty acids can be obtained with high purity.

得られるアリール脂肪酸は品質的に優れているので、抗
酸化剤、腐食防止剤、潤滑油添加剤をはじめとする巾広
い用途に使用することができる。The resulting aryl fatty acids are of excellent quality and can be used in a wide range of applications including antioxidants, corrosion inhibitors, and lubricating oil additives.

〔実施例〕〔Example〕

次に本発明を実施例により説明する。以下の実施例にお
いてチは重量％を示す。Next, the present invention will be explained by examples. In the following examples, q indicates weight %.

実施例１゜ オレイン酸（純度７５％、リノール酸９チ、炭素数１４
〜１６の不飽和酸８％、炭素数１４〜１８の飽和酸８チ
）　１６６ｙ、フェノール１６９ｙ。Example 1 Oleic acid (75% purity, 9% linoleic acid, 14 carbon atoms)
166y, phenol 169y.

活性白土（日本活性白土■製）　６．６　ｙ　（不飽和
脂肪酸に対して４゜３％）および８５係リン酸水溶液０
、１３　ｙ（不飽和脂肪酸に対してリン酸として０゜０
７２チ）を５００ｍ／のオートクレーブに仕込み、窒素
ガス置換したのち、２００Ｃで４時間反応した。反応終
了後触媒を戸別し、未反応フェノールｋ　８０〜１００
　Ｃ，３ｍｍＨｇ　で留去して黄色の粘稠な生成物２２
４ｙを得た。生成物の分析値は表−１にまとめて示す。Activated clay (manufactured by Japan Activated Clay) 6.6 y (4°3% based on unsaturated fatty acids) and 85 group phosphoric acid aqueous solution 0
, 13 y (0°0 as phosphoric acid for unsaturated fatty acids
72 ml) was placed in a 500 m/autoclave, the atmosphere was purged with nitrogen gas, and then reacted at 200 C for 4 hours. After the reaction is completed, remove the catalyst from door to door and remove unreacted phenol K from 80 to 100.
C, distilled off at 3 mmHg to give a yellow viscous product 22
Got 4y. The analytical values of the product are summarized in Table 1.

実施例２〜８および比較例１〜６ 活性白土の使用量およびり／の酸素酸の種類と使用量を
変化させる以外は実施例１と全く同じに試験した。結果
を表−ＩＫまとめて示す。Examples 2 to 8 and Comparative Examples 1 to 6 Tests were carried out in exactly the same manner as in Example 1, except that the amount of activated clay used and the type and amount of oxyacid used were changed. The results are summarized in Table IK.

比較例７゜ リンの酸素酸の代りに直鎖アルキル（炭素数１２）ベン
ゼンスルホン酸ｏ、　ｓ　ｙ　（不飽和脂肪酸に対して
０．５２　％　）を用いる以外は実施例１と同様に試験
した。結果を表−１にまとめて示す。Comparative Example 7 The test was carried out in the same manner as in Example 1, except that straight-chain alkyl (12 carbon atoms) benzenesulfonic acid o, sy (0.52% based on unsaturated fatty acid) was used instead of phosphorus oxygen acid. . The results are summarized in Table-1.

放物の収量および性状が優れているばかりでなくリン化
合物がほとんど残存していないことが判る。It can be seen that not only the yield and properties of the parabolites are excellent, but also that almost no phosphorus compounds remain.

これに対して、活性白土またはリンの酸素酸を単独で用
いた場合には反応が完結しないし、また使用猾が少なす
ぎたり、多すぎる場合には生成物の収量や性状において
劣っているだけでな（リン化合物が残存していることが
判る。On the other hand, if activated clay or phosphorus oxygen acid is used alone, the reaction will not be completed, and if too little or too much is used, the yield and properties of the product will be inferior. (It can be seen that phosphorus compounds remain.

実施例９゜ オレイン酸の代りにオレイン酸メチル（実施例１０オレ
イン酸と同じ組成）１７４ｙを用いて実施例１と同様に
反応し、処理なして生成物２３１１を得た。結果を表−
２に示す。Example 9 A reaction was carried out in the same manner as in Example 1 using methyl oleate (same composition as oleic acid in Example 10) 174y instead of oleic acid, and product 2311 was obtained without treatment. Display the results -
Shown in 2.

比較例８ 触媒として活性白土のみを用いる以外は実施例９と同様
に反応し、処理をして生成物２２１りを得た。結果を表
−２に示す。Comparative Example 8 The reaction and treatment were carried out in the same manner as in Example 9 except that only activated clay was used as a catalyst to obtain product 221. The results are shown in Table-2.

表−２生成物の性状 表−２の結果から、オレイン酸の代りにオレイン酸メチ
ルを用いた場合においても、本発明の方法が優れている
ことが判る。Table 2 Product Properties The results in Table 2 show that the method of the present invention is superior even when methyl oleate is used in place of oleic acid.

実施例１０゜ オレイン酸（実施例１と同じ組成）１６６ｙ、トルエン
１６９１、活性白土１６．６　Ｆ　（不飽和脂肪酸に対
して１０．９　％　）、８５ｑ６リン酸水溶液１゜３９
１（不飽和脂肪酸に対して０．７２　％　）を５００４
オートクレーブに仕込み、窒素ガス置換したのち、２０
０Ｃで２０時間反応した。反応終了後、実施例１と同様
に処理して生成物を得た。結果を表−３にまとめて示す
。Example 10 Oleic acid (same composition as Example 1) 166y, toluene 1691, activated clay 16.6F (10.9% based on unsaturated fatty acid), 85q6 phosphoric acid aqueous solution 1°39
1 (0.72% based on unsaturated fatty acids) to 5004
After putting it in an autoclave and replacing it with nitrogen gas,
The reaction was carried out at 0C for 20 hours. After the reaction was completed, the same treatment as in Example 1 was carried out to obtain a product. The results are summarized in Table 3.

実施例１１゜ トルエンの代りにアニソール１９５ｊ！を用いる以外は
実施例１０と同様に行った。結果を表−３にまとめて示
す。Example 11 Anisole 195j instead of toluene! The same procedure as in Example 10 was carried out except that . The results are summarized in Table 3.

比較例９゜ 実施例１０においてリン酸を用いない以外は同じ条件で
反応した。Comparative Example 9 A reaction was carried out under the same conditions as in Example 10 except that phosphoric acid was not used.

比較例１Ｏ 実施例１１においてリン酸を用いない以外は同じ条件で
反応した。Comparative Example 1O The reaction was carried out under the same conditions as in Example 11 except that phosphoric acid was not used.

これらの結果を表−３にまとめて示す。These results are summarized in Table 3.

（以下余白） 表−３の結果から、本発明の活性白土とリン酸とを用い
る場合には、トルエンおよびアニソールのオレイン酸へ
の付加反応率が高いのに対して。(The following is a blank space) From the results of Table 3, when using the activated clay of the present invention and phosphoric acid, the addition reaction rate of toluene and anisole to oleic acid is high.

活性白土単独では付加反応率の低いことが認められる。It is recognized that the addition reaction rate is low when activated clay alone is used.

本発明の方法はヒドロキシアリール脂肪酸を収率よ〈製
造できるだけでなく、従来、活性白土単独では不可能で
あったトルエン、アニソールなどのヒドロキシ基を持た
ない、反応性の低いアリール化合物の不飽和脂肪酸への
付加を可能としていることが判る。The method of the present invention not only enables the production of hydroxyaryl fatty acids with a high yield, but also unsaturated fatty acids of aryl compounds with low reactivity that do not have hydroxyl groups such as toluene and anisole, which was previously impossible with activated clay alone. It can be seen that it is possible to add

実施例１２および１３ オレイン酸に対するフェノールの使用量を変化させて、
その他は実施例２と同様に反応し、処理した。結果を表
−４に示す。Examples 12 and 13 By varying the amount of phenol used relative to oleic acid,
The reaction and treatment were otherwise the same as in Example 2. The results are shown in Table 4.

（以下余白） 表−４の結果から、本発明のアリール脂肪酸の製造法は
アリール化合物と不飽和脂肪酸類の巾広い比率において
有効であることが判る。(The following is a blank space) From the results in Table 4, it can be seen that the method for producing aryl fatty acids of the present invention is effective in a wide range of ratios of aryl compounds and unsaturated fatty acids.

Claims (1)

【特許請求の範囲】[Claims] １　アリール化合物と不飽和脂肪酸類との付加反応に際
し、触媒として不飽和脂肪酸類に対して１〜１２重量％
の活性白土と０．０５〜０．７５重量％のリンの酸素酸
とを用いることを特徴とするアリール脂肪酸の製造法。1. 1 to 12% by weight of the unsaturated fatty acids as a catalyst during the addition reaction between the aryl compound and the unsaturated fatty acids.
1. A method for producing an aryl fatty acid, which comprises using activated clay and 0.05 to 0.75% by weight of phosphorus oxyacid.
JP60149250A 1985-07-09 1985-07-09 Production of aryl fatty acid Granted JPS6210040A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60149250A JPS6210040A (en) 1985-07-09 1985-07-09 Production of aryl fatty acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60149250A JPS6210040A (en) 1985-07-09 1985-07-09 Production of aryl fatty acid

Publications (2)

Publication Number Publication Date
JPS6210040A true JPS6210040A (en) 1987-01-19
JPH0260654B2 JPH0260654B2 (en) 1990-12-17

Family

ID=15471153

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60149250A Granted JPS6210040A (en) 1985-07-09 1985-07-09 Production of aryl fatty acid

Country Status (1)

Country Link
JP (1) JPS6210040A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5840942A (en) * 1993-12-02 1998-11-24 Baker Hughes Incorporated Catalyzed synthesis of aryl-substituted fatty acids and fatty esters and compositions related thereto
JP2016216488A (en) * 2010-09-30 2016-12-22 ハンツマン ペトロケミカル エルエルシーＨｕｎｔｓｍａｎ Ｐｅｔｒｏｃｈｅｍｉｃａｌ ＬＬＣ Surface active agent derived from biodiesel-based alkylated aromatic compound

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5840942A (en) * 1993-12-02 1998-11-24 Baker Hughes Incorporated Catalyzed synthesis of aryl-substituted fatty acids and fatty esters and compositions related thereto
JP2016216488A (en) * 2010-09-30 2016-12-22 ハンツマン ペトロケミカル エルエルシーＨｕｎｔｓｍａｎ Ｐｅｔｒｏｃｈｅｍｉｃａｌ ＬＬＣ Surface active agent derived from biodiesel-based alkylated aromatic compound

Also Published As

Publication number Publication date
JPH0260654B2 (en) 1990-12-17

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