JPH0765068B2 - Method for producing saturated fatty acid - Google Patents
Method for producing saturated fatty acidInfo
- Publication number
- JPH0765068B2 JPH0765068B2 JP31519786A JP31519786A JPH0765068B2 JP H0765068 B2 JPH0765068 B2 JP H0765068B2 JP 31519786 A JP31519786 A JP 31519786A JP 31519786 A JP31519786 A JP 31519786A JP H0765068 B2 JPH0765068 B2 JP H0765068B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- acid
- saturated
- carbon atoms
- unsaturated
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は極めて簡単な処理を行うことによって出発原料
である不飽和脂肪酸エステルよりも脂肪酸部分の炭素数
が２個少ない飽和脂肪酸を製造する方法に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention is a method for producing a saturated fatty acid in which the number of carbon atoms in the fatty acid portion is 2 less than that of the unsaturated fatty acid ester as a starting material by performing an extremely simple treatment. It is about.
出発原料である直鎖不飽和脂肪酸よりも炭素数が２つ少
ない直鎖飽和脂肪酸を製造する方法としては、バーレン
トラップ反応が知られている（アックマン（R.G.ACKMAN
et al）、テトラヘドロン（Tetra hedron）Vol 8,P221
〜238（1960））。この方法では、融溶水酸化カリウム
などの強アルカリを用い、窒素気流下、300〜380℃の高
温で１〜５時間不飽和脂肪酸を処理し、該脂肪酸を炭素
数が２つ少ない飽和脂肪酸と酢酸とに分解するのであ
る。この方法によれば、高収率で飽和脂肪酸を製造でき
るとされているが、この方法は強アルカリ下、高温圧力
で反応を行う為に、装置が大型化、複雑化するととも
に、安全上問題があり、又、エネルギー収支上からも経
済的でないという問題があった。The Barren trap reaction is known as a method for producing a linear saturated fatty acid having two carbon atoms less than that of the starting linear unsaturated fatty acid (RGACKMAN
et al), Tetra hedron Vol 8, P221
~ 238 (1960)). In this method, an unsaturated fatty acid is treated with a strong alkali such as melted potassium hydroxide at a high temperature of 300 to 380 ° C. for 1 to 5 hours under a nitrogen stream to convert the fatty acid into a saturated fatty acid having two fewer carbon atoms. It decomposes into acetic acid. According to this method, saturated fatty acids can be produced in high yield, but since this method carries out the reaction at high temperature and pressure under strong alkali, the equipment becomes large and complicated, and it is a safety problem. However, there was a problem that it was not economical in terms of energy balance.
従って、本発明は、温和な条件下で簡単な装置を用い
て、不飽和，飽和混合脂肪酸エステルから飽和脂肪酸を
効率よく製造できる方法を提供することを目的とする。Therefore, an object of the present invention is to provide a method capable of efficiently producing a saturated fatty acid from an unsaturated saturated fatty acid ester using a simple apparatus under mild conditions.
本発明は、不飽和，飽和混合脂肪酸エステルを、特定量
の酸及び過酸化水素と混合するだけで、原料中の不飽和
脂肪酸エステル部分の炭素鎖の切断が容易に起り、原料
の脂肪酸部分より炭素数が２つ少ない飽和脂肪酸が得ら
れるとの知見に基づいてなされたものである。The present invention easily mixes an unsaturated and saturated mixed fatty acid ester with a specific amount of acid and hydrogen peroxide to easily cut the carbon chain of the unsaturated fatty acid ester portion in the raw material, This was done based on the finding that a saturated fatty acid having two carbon atoms is obtained.
すなわち、本発明は、炭素数８〜30の不飽和，飽和混合
脂肪酸と炭素数１〜８のアルコールとのエステル化物10
0重量部当りに、酸１〜50重量部及び過酸化水素0.1〜10
重量部を加えて20〜100℃で反応させ、不飽和脂肪酸エ
ステルの脂肪酸部分より炭素数が２つ少ない飽和脂肪酸
を得ることを特徴とする飽和脂肪酸の製造方法を提供す
る。That is, the present invention relates to an esterified product of an unsaturated and saturated mixed fatty acid having 8 to 30 carbon atoms and an alcohol having 1 to 8 carbon atoms.
0 to 50 parts by weight of acid and 0.1 to 10 parts by weight of hydrogen peroxide
Provided is a method for producing a saturated fatty acid, which comprises adding a part by weight and reacting at 20 to 100 ° C. to obtain a saturated fatty acid having 2 carbon atoms less than the fatty acid portion of the unsaturated fatty acid ester.
本発明で処理の対象となる不飽和，飽和混合脂肪酸エス
テルの脂肪酸部分としては、炭素数が８〜30、好ましく
は10〜20であり、分子内に不飽和結合が少なくとも１
個、好ましくは１〜３個有する不飽和，飽和混合脂肪酸
があげられ、特に、直鎖不飽和，飽和混合脂肪酸を用い
るのがよい。また、該不飽和，飽和混合脂肪酸とアルコ
ールとのエステル化物としては、炭素数１〜８の１価ア
ルコールとのエステル化物、エチレングリコール、プロ
ピレングリコールなどの２価アルコールとのモノ又はジ
エステル化物、グリセリンとのモノ、ジ、トリエステ
ル、ペンタエリスリトール、ソルビタンなどの多価アル
コールとの部分又は全エステル化物があげられる。具体
的には、パーム脂肪酸、牛脂脂肪酸、ヤシ脂肪酸などの
天然脂肪酸と１価アルコールや多価アルコールとのエス
テルなどが例示される。The fatty acid portion of the unsaturated and saturated mixed fatty acid ester to be treated in the present invention has 8 to 30 carbon atoms, preferably 10 to 20 carbon atoms and at least 1 unsaturated bond in the molecule.
Unsaturated and saturated mixed fatty acids having one, preferably one to three, can be mentioned, and it is particularly preferable to use straight chain unsaturated and saturated mixed fatty acids. As the esterification product of the unsaturated and saturated mixed fatty acids and alcohol, esterification product of monohydric alcohol having 1 to 8 carbon atoms, mono- or diesterification product of dihydric alcohol such as ethylene glycol and propylene glycol, glycerin And partial or total esterification products with polyhydric alcohols such as mono-, di-, triesters, pentaerythritol and sorbitan. Specific examples thereof include esters of natural fatty acids such as palm fatty acids, beef tallow fatty acids, and coconut fatty acids with monohydric alcohols and polyhydric alcohols.
尚、これらのうち、理由は不明であるが、不飽和脂肪酸
エステルに飽和脂肪酸エステルを混合し、全体のIV（ヨ
ウ素価）が0.6〜50、好ましくは0.6〜30となるようにし
たものを原料として用いると反応が穏やかに行なわれ
て、不飽和脂肪酸エステルから飽和脂肪酸が高収率で得
られる。そして、この際、混合する飽和脂肪酸エステル
として、不飽和脂肪酸エステルよりも炭素数が２つ少な
いものを用いると、単一鎖長の脂肪酸が得られるので有
利である。Of these, for unknown reasons, unsaturated fatty acid ester is mixed with saturated fatty acid ester so that the total IV (iodine value) is 0.6 to 50, preferably 0.6 to 30 When used as, the reaction is carried out gently, and saturated fatty acid can be obtained in high yield from unsaturated fatty acid ester. Then, in this case, it is advantageous to use a saturated fatty acid ester having two carbon atoms less than that of the unsaturated fatty acid ester, since a fatty acid having a single chain length can be obtained.
本発明では、上記不飽和，飽和混合脂肪酸エステル100
重量部に対して、酸１〜50重量部（以下、部と略称す
る。）好ましくは10〜30部及び過酸化水素を100％過酸
化水素として、0.1〜10部、好ましくは0.2〜５部を添加
する。ここで用いる酸としては、硫酸、リン酸、塩酸な
どの無機酸やベンゼンスルホン酸、アルキル基の炭素数
が１〜14のアルキルベンゼンスルホン酸などの有機酸を
あげることができる。これらのうち、好ましい酸は、硫
酸、アルキルベンゼンスルホン酸である。In the present invention, the unsaturated and saturated mixed fatty acid ester 100
1 to 50 parts by weight of acid (hereinafter abbreviated as "parts"), preferably 10 to 30 parts, and hydrogen peroxide as 100% hydrogen peroxide, 0.1 to 10 parts, preferably 0.2 to 5 parts. Is added. Examples of the acid used here include inorganic acids such as sulfuric acid, phosphoric acid and hydrochloric acid, and organic acids such as benzenesulfonic acid and alkylbenzenesulfonic acid having an alkyl group having 1 to 14 carbon atoms. Of these, preferred acids are sulfuric acid and alkylbenzene sulfonic acid.
本発明では、上記成分を添加、混合して、脂肪酸エステ
ル中の脂肪酸部分の炭素鎖をアルキル基末端から２番目
と３番目の炭素結合の間で切断する。この際、混合を20
〜100℃、好ましくは40〜80℃で、10分〜２時間、好ま
しくは30分〜１時間行うのが望ましい。すなわち20℃未
満で反応を行うと反応がほとんど進まず目標とする飽和
脂肪酸が得られず、一方100℃を越えて行うと、得られ
る飽和脂肪酸の色や臭いなどを劣化させ好ましくないか
らである。In the present invention, the above components are added and mixed to cut the carbon chain of the fatty acid portion in the fatty acid ester between the second and third carbon bonds from the end of the alkyl group. At this time, mix 20
It is desirable to carry out at -100 ° C, preferably 40-80 ° C for 10 minutes to 2 hours, preferably 30 minutes to 1 hour. That is, when the reaction is carried out at less than 20 ° C, the reaction hardly proceeds and the target saturated fatty acid cannot be obtained, while when it is carried out at more than 100 ° C, the color and odor of the obtained saturated fatty acid are deteriorated, which is not preferable. .
本発明によれば、装置の大型化、複雑化及び安全性、エ
ネルギーロス等の問題を伴うことなく、極めて簡単な方
法で、原料の不飽和脂肪酸エステルよりも炭素数が２つ
少ない飽和脂肪酸を製造することができる。According to the present invention, a saturated fatty acid having two carbon atoms less than that of the unsaturated fatty acid ester as a raw material can be obtained by a very simple method without problems such as an increase in size of the device, complication and safety, and energy loss. It can be manufactured.
さらに、酸／過酸化水素の添加割合を変えることにより
飽和／不飽和脂肪酸及びエステルの比率を簡単かつ自由
にコントロールできるので希望する性状の油脂を得やす
く、界面活性剤原料としての界面張力、浸透力、起泡
力、すすぎ性などの基礎性能を容易に調整でき、本発明
により製造される脂肪酸及びそのエステル化物は、洗剤
工業などの多くの分野での幅広い展開が期待できる。特
に、洗剤原料としてはIVが３以下のものが好ましいが、
このようなものは本発明により容易に製造できる。In addition, the ratio of saturated / unsaturated fatty acids and esters can be easily and freely controlled by changing the ratio of acid / hydrogen peroxide addition, which makes it easy to obtain fats and oils with the desired properties, and the interfacial tension and penetration as a surfactant raw material. The basic properties such as strength, foaming power and rinsing property can be easily adjusted, and the fatty acid and its esterified product produced by the present invention can be expected to be widely developed in many fields such as the detergent industry. Particularly, as the detergent raw material, IV having 3 or less is preferable,
Such a thing can be easily manufactured by the present invention.
次に本発明を実施例により説明するが、本発明はこれら
に限定されるものではない。Next, the present invention will be described with reference to examples, but the present invention is not limited thereto.
実施例１ オレイン酸メチルエステル（IV＝84）59gとステアリン
酸メチルエステル（IV＜0.1）941gを2lの混合容器に入
れ、この中に35％H2O235gと濃硫酸50gを加え温度80℃で
約１時間攪拌しながら混合を行なった。次に、得られた
混合物を静置分離後油層を温水洗浄し、次いで水をトッ
ピング除去した後、芒硝脱水して、所望の直鎖飽和脂肪
酸及びそのエステルを得た。主生成物のIVをウィス法で
測定したところ0.3に減少しており、更にGC法で測定し
た所、パルミチン酸が４モル％生成した（オレイン酸メ
チルエステルに対する収率は80％）。Example 1 59 g of oleic acid methyl ester (IV = 84) and 941 g of stearic acid methyl ester (IV <0.1) were placed in a 2 liter mixing vessel, to which 35% H 2 O 2 35 g and concentrated sulfuric acid 50 g were added, and the temperature was adjusted to 80 Mixing was carried out while stirring at ℃ for about 1 hour. Next, after the resulting mixture was allowed to stand and separate, the oil layer was washed with warm water, water was removed by topping, and then sodium sulfate was dehydrated to obtain a desired straight chain saturated fatty acid and its ester. The main product IV was reduced to 0.3 when measured by the Wis method, and further 4 mol% of palmitic acid was generated when measured by the GC method (yield to oleic acid methyl ester was 80%).
実施例２ 実施例１で用いたオレイン酸メチルエステルとステアリ
ン酸メチルエステルの混合比を種々を変えたものについ
て、酸と過酸化水素を加えて反応を行った。反応条件及
び結果をまとめて表−１に示す。尚、表中の酸及び過酸
化水素の添加量は、原料エステル100重量部当りの重量
部である。又、収率は減少したオレイン酸メチルエステ
ルに対する生成したパルミチン酸の量（％）で示した。Example 2 With respect to the oleic acid methyl ester and the stearic acid methyl ester used in Example 1 having different mixing ratios, an acid and hydrogen peroxide were added to carry out the reaction. The reaction conditions and results are summarized in Table 1. The addition amounts of acid and hydrogen peroxide in the table are parts by weight per 100 parts by weight of the raw material ester. The yield was expressed as the amount (%) of palmitic acid produced with respect to the reduced oleic acid methyl ester.
表−１の結果から本発明によればオレイン酸エステルを
炭素数の２個少いパルミチン酸に好収率で転換すること
ができる。 According to the present invention, it is possible to convert the oleic acid ester to palmitic acid having two less carbon atoms in good yield from the results shown in Table 1.
Claims (2)
炭素数１〜８のアルコールとのエステル化物100重量部
当りに、酸１〜50重量部及び過酸化水素0.1〜10重量部
を加えて20〜100℃で反応させ、不飽和脂肪酸エステル
の脂肪酸部分より炭素数が２つ少ない飽和脂肪酸を得る
ことを特徴とする飽和脂肪酸の製造方法。1. 1 to 50 parts by weight of an acid and 0.1 to 10 parts by weight of hydrogen peroxide per 100 parts by weight of an esterified product of an unsaturated or saturated mixed fatty acid having 8 to 30 carbon atoms and an alcohol having 1 to 8 carbon atoms. A method for producing a saturated fatty acid, which comprises adding saturated carboxylic acid and reacting at 20 to 100 ° C. to obtain a saturated fatty acid having 2 carbon atoms less than the fatty acid portion of the unsaturated fatty acid ester.
コールである特許請求の範囲第（１）項記載の製造方
法。2. The production method according to claim 1, wherein the alcohol is a monohydric alcohol or a polyhydric alcohol.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31519786A JPH0765068B2 (en) | 1986-12-26 | 1986-12-26 | Method for producing saturated fatty acid |
| EP87111902A EP0257510A3 (en) | 1986-08-21 | 1987-08-17 | Method for modifying unsaturated fatty acid or ester thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31519786A JPH0765068B2 (en) | 1986-12-26 | 1986-12-26 | Method for producing saturated fatty acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63165339A JPS63165339A (en) | 1988-07-08 |
| JPH0765068B2 true JPH0765068B2 (en) | 1995-07-12 |
Family
ID=18062577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31519786A Expired - Lifetime JPH0765068B2 (en) | 1986-08-21 | 1986-12-26 | Method for producing saturated fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0765068B2 (en) |
-
1986
- 1986-12-26 JP JP31519786A patent/JPH0765068B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63165339A (en) | 1988-07-08 |
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