JPH11335340A - Production of fatty acid amide ether - Google Patents
Production of fatty acid amide etherInfo
- Publication number
- JPH11335340A JPH11335340A JP13979098A JP13979098A JPH11335340A JP H11335340 A JPH11335340 A JP H11335340A JP 13979098 A JP13979098 A JP 13979098A JP 13979098 A JP13979098 A JP 13979098A JP H11335340 A JPH11335340 A JP H11335340A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- reaction
- alkanolamine
- carbon atoms
- hydrogen atom
- 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
Links
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- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は高純度の脂肪酸アミ
ドエーテルの効率的な製造法に関する。The present invention relates to an efficient method for producing a high-purity fatty acid amide ether.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】脂肪酸
アミドエーテルは起泡力が良好で溶解性に優れ、洗浄力
が高いため、洗浄剤の主剤や補助剤として広く用いられ
ている。従来、脂肪酸アミドエーテルの製造は、脂肪酸
メチルエステルとアルカノールアミンをアルカリ触媒下
で反応させて脂肪酸アルカノールアミドを製造し、さら
にアルキレンオキサイドを付加させて行われていた。こ
の方法では、短い反応時間で高純度の脂肪酸アルカノー
ルアミドが得られ、そこから誘導される脂肪酸アミドエ
ーテルも純度が高いものが得られる。しかしながら、脂
肪酸メチルエステルは脂肪酸に比べ高価であり、経済的
に不利である上、アミド化反応でメタノールを等モル副
生し、後処理などに負荷がかかる。2. Description of the Related Art Fatty acid amide ethers are widely used as a base agent and an auxiliary agent of detergents because of their good foaming power, excellent solubility, and high detergency. Conventionally, fatty acid amide ethers have been produced by reacting a fatty acid methyl ester with an alkanolamine under an alkaline catalyst to produce a fatty acid alkanolamide, and further adding an alkylene oxide. In this method, high-purity fatty acid alkanolamide is obtained in a short reaction time, and fatty acid amide ether derived therefrom is also obtained with high purity. However, fatty acid methyl esters are more expensive than fatty acids, are economically disadvantageous, and produce an equimolar amount of methanol as a by-product of the amidation reaction, which imposes a burden on post-treatment and the like.
【０００３】一方、脂肪酸アミドエーテルを製造するた
めの中間体である脂肪酸アルカノールアミドを得る方法
として、安価な脂肪酸とアルカノールアミンを一括して
反応系に仕込み、反応させる方法が知られている。しか
しこの方法は原材料費は安価であるが、反応で生じる水
の除去が難しいため、反応が効率的に進行せず、未反応
の脂肪酸やアルカノールアミンが残存し、また脂肪酸ア
ミドエステル、エステルアミンなどの反応副生成物も多
く存在する。こうした種々の不純物が、得られた脂肪酸
アルカノールアミドにアルキレンオキサイドを付加する
際に悪影響を及ぼし、大量のポリエチレングリコールな
どの副生成物ができるばかりでなく、匂い、溶解性、洗
浄力などにも悪影響を及ぼすなど問題がある。また、反
応温度を高くして反応を行う方法もあるが、この場合、
反応水の効率的な除去は可能であるが、水と同時に未反
応のアルカノールアミンが留出し、反応系内のアルカノ
ールアミンが不足するため反応が十分に進行しない。On the other hand, as a method for obtaining a fatty acid alkanolamide which is an intermediate for producing a fatty acid amide ether, a method is known in which inexpensive fatty acids and alkanolamines are collectively charged into a reaction system and reacted. However, this method has a low raw material cost, but it is difficult to remove water generated by the reaction, so the reaction does not proceed efficiently, unreacted fatty acids and alkanolamines remain, and fatty acid amide esters, ester amines, etc. Many reaction by-products also exist. These various impurities adversely affect the addition of the alkylene oxide to the obtained fatty acid alkanolamide, which not only produces a large amount of by-products such as polyethylene glycol, but also has an adverse effect on odor, solubility, detergency, and the like. There is a problem. There is also a method in which the reaction is carried out at a high reaction temperature.
Although the reaction water can be efficiently removed, unreacted alkanolamine is distilled off at the same time as the water, and the reaction does not proceed sufficiently due to a shortage of alkanolamine in the reaction system.
【０００４】従って、本発明の課題は、安価な脂肪酸を
原料として高純度の脂肪酸アミドエーテルを効率良く製
造する方法を提供することである。Accordingly, an object of the present invention is to provide a method for efficiently producing high-purity fatty acid amide ethers using inexpensive fatty acids as raw materials.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、脂肪酸中
にアルカノールアミンを添加しながら反応させることに
より、反応時間が短く、アルカノールアミンを大過剰に
使用することなく、効率良く高純度の脂肪酸アミドエー
テルを製造できることを見出した。Means for Solving the Problems The inventors of the present invention made it possible to carry out a reaction while adding an alkanolamine to a fatty acid so that the reaction time was short, the alkanolamine was not used in a large excess, and the fatty acid was efficiently and highly purified. It has been found that fatty acid amide ethers can be produced.
【０００６】即ち、本発明は、脂肪酸中にアルカノール
アミンを添加しながら反応させて脂肪酸アルカノールア
ミドを製造し、次いでアルキレンオキサイドを付加させ
る脂肪酸アミドエーテルの製造法である。That is, the present invention is a process for producing a fatty acid amide ether by producing a fatty acid alkanolamide by reacting while adding an alkanolamine to a fatty acid, and then adding an alkylene oxide.
【０００７】[0007]
【発明の実施の形態】本発明に用いられる脂肪酸は、炭
素数６〜22の飽和又は不飽和の脂肪酸が好ましく、例え
ば、ヘキサン酸、ヘプタン酸、カプリン酸、カプリル
酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステア
リン酸、オレイン酸、ノナデカン酸、ベヘニン酸、エル
カ酸、或いは牛脂等の動物油又はヤシ油等の植物油から
誘導される脂肪酸等が挙げられ、これらの１種以上を用
いることができる。炭素数６〜14の脂肪酸が更に好まし
い。BEST MODE FOR CARRYING OUT THE INVENTION The fatty acid used in the present invention is preferably a saturated or unsaturated fatty acid having 6 to 22 carbon atoms, for example, hexanoic acid, heptanoic acid, capric acid, caprylic acid, lauric acid, myristic acid, Examples thereof include palmitic acid, stearic acid, oleic acid, nonadecanoic acid, behenic acid, erucic acid, and fatty acids derived from animal oils such as tallow or vegetable oils such as coconut oil, and one or more of these can be used. C6-14 fatty acids are more preferred.
【０００８】本発明に用いられるアルカノールアミン
は、一般式（II）The alkanolamine used in the present invention has the general formula (II)
【０００９】[0009]
【化２】 Embedded image
【００１０】〔式中、X は水素原子又は炭素数１〜３の
直鎖又は分岐鎖のアルキル基、Z は水素原子又は水酸基
で置換されていてもよい炭素数１〜３の直鎖又は分岐鎖
のアルキル基を示す。〕で表される化合物が挙げられ
る。Wherein X is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and Z is a linear or branched alkyl group having 1 to 3 carbon atoms which may be substituted with a hydrogen atom or a hydroxyl group. Shows the alkyl group of the chain. ] The compound represented by this is mentioned.
【００１１】一般式（II）で表される化合物の具体例
は、モノエタノールアミン、イソプロパノールアミン、
ジエタノールアミン、２−（メチルアミノ）エタノー
ル、２−（エチルアミノ）エタノール、２−（プロピル
アミノ）エタノール等であり、モノエタノールアミン、
イソプロパノールアミノが更に好ましい。Specific examples of the compound represented by the general formula (II) include monoethanolamine, isopropanolamine,
Diethanolamine, 2- (methylamino) ethanol, 2- (ethylamino) ethanol, 2- (propylamino) ethanol, etc., and monoethanolamine,
Isopropanolamino is more preferred.
【００１２】脂肪酸とアルカノールアミンとの反応は、
脂肪酸を反応槽に仕込み、所定の反応温度まで加熱した
ところで、アルカノールアミンを添加しなから反応させ
ることで行う。そのため、アルカノールアミンの留出速
度よりアミド化反応が速くなり、アミド化反応が十分に
進行して純度が高くなる。The reaction of a fatty acid with an alkanolamine is
The reaction is carried out by charging the fatty acid into a reaction vessel and heating it to a predetermined reaction temperature, and then adding alkanolamine to the reaction. Therefore, the amidation reaction becomes faster than the distillation rate of the alkanolamine, and the amidation reaction proceeds sufficiently to increase the purity.
【００１３】アルカノールアミンの添加は反応槽内部の
気相部からの添加（液量が少ないときは滴下となること
がある）、又は液相中に直接添加のいずれでもかまわな
い。添加はポンプで一定速度で行うのが好ましい。反応
に用いるアルカノールアミンの全量を添加する時間（以
下添加時間という）は 0.5時間〜４時間が好ましく、１
〜３時間が更に好ましい。添加時間が0.5 時間以上で
は、アルカノールアミンの留出量を少なくでき、その結
果、反応に用いるアルカノールアミンの量を低減するこ
とができる。また、添加時間が４時間以下では、反応時
間を短くし、色相を良好にし、生産効率を良くすること
ができる。The alkanolamine may be added from the gas phase inside the reaction vessel (it may be dropped when the amount of liquid is small) or directly into the liquid phase. The addition is preferably performed at a constant rate with a pump. The time for adding the total amount of the alkanolamine used for the reaction (hereinafter referred to as the addition time) is preferably 0.5 to 4 hours,
３3 hours are more preferred. When the addition time is 0.5 hours or more, the amount of alkanolamine distilled out can be reduced, and as a result, the amount of alkanolamine used in the reaction can be reduced. When the addition time is 4 hours or less, the reaction time can be shortened, the hue can be improved, and the production efficiency can be improved.
【００１４】脂肪酸とアルカノールアミンとの反応モル
比は、アルカノールアミン／脂肪酸＝0.9〜1.2の範囲
が、アミド化反応が効率良く、収率も高いため好まし
い。脂肪酸とアルカノールアミンとの反応時の圧力は常
圧が、アルカノールアミンの留出を抑え、収率や生産効
率を良好にし、得られる脂肪酸アルカノールアミドの純
度を高くし、そこから誘導される脂肪酸アミドエーテル
の純度を高くするため好ましい。The reaction molar ratio of the fatty acid to the alkanolamine is preferably in the range of alkanolamine / fatty acid = 0.9 to 1.2 because the amidation reaction is efficient and the yield is high. The pressure during the reaction between the fatty acid and the alkanolamine is normal pressure, which suppresses the distillation of the alkanolamine, improves the yield and production efficiency, increases the purity of the obtained fatty acid alkanolamide, and increases the fatty acid amide derived therefrom. It is preferable to increase the purity of the ether.
【００１５】反応温度は、反応速度を早め、反応物の着
色を抑える点で 150〜250 ℃が好ましく、より好ましく
は 160〜200 ℃である。従来の製造方法においては、ア
ルカノールアミン全量を一度に仕込むため、160 ℃を超
える反応温度ではアルカノールアミンの沸点以上である
ため、アルカノールアミンが留出し、系内のアルカノー
ルアミンが不足して未反応の脂肪酸が大量に残存してし
まうため好ましくないとされてきた。しかし、本発明に
おいては高い反応温度下で脂肪酸中にアルカノールアミ
ンを添加することにより、反応に関与しないまま留出す
るアルカノールアミン量を抑制すること、すなわち、ア
ルカノールアミンの使用量の低減が可能となり、また、
高い温度で反応できることから、効率的に反応水を除去
でき、好適に反応を進行させることが可能となる。[0015] The reaction temperature is preferably from 150 to 250 ° C, more preferably from 160 to 200 ° C, in order to increase the reaction rate and suppress the coloring of the reaction product. In the conventional production method, since the entire amount of alkanolamine is charged all at once, the reaction temperature exceeding 160 ° C. is higher than the boiling point of alkanolamine. It has been considered undesirable because fatty acids remain in large quantities. However, in the present invention, by adding alkanolamine to the fatty acid at a high reaction temperature, it is possible to suppress the amount of alkanolamine distilled out without participating in the reaction, that is, it is possible to reduce the amount of alkanolamine used. ,Also,
Since the reaction can be performed at a high temperature, the reaction water can be efficiently removed, and the reaction can be favorably advanced.
【００１６】以上の方法で高純度の脂肪酸アルカノール
アミドが得られるが、より純度を高くするためにごく少
量含まれる不純物を減少させる必要がある時は、さらに
金属アルコラートの添加による処理を行なうことができ
る。この場合、加えた金属アルコラートは、次工程のア
ルキレンオキサイドの付加反応の触媒作用と、副生成物
をアルカノールアミドに転化する効果の両方を備えてい
るため、脂肪酸アミドエーテルの純度を上げることがで
きる上、経済的でもある。Although a high-purity fatty acid alkanolamide can be obtained by the above method, when it is necessary to reduce impurities contained in a very small amount in order to further increase the purity, a treatment by adding a metal alcoholate may be further performed. it can. In this case, since the added metal alcoholate has both the catalytic action of the addition reaction of the alkylene oxide in the next step and the effect of converting the by-product to alkanolamide, the purity of the fatty acid amide ether can be increased. It is also economical.
【００１７】以上の方法で得られた脂肪酸アルカノール
アミドは高純度で、水や副生成物をほとんど含まない。
このものに加圧下でアルキレンオキサイドを付加するこ
とにより高純度、高品質の脂肪酸アミドエーテルを製造
することができる。また脂肪酸メチルエステルより安価
な原料である脂肪酸を使用することにより経済的にも優
れたものである。The fatty acid alkanolamide obtained by the above method has high purity and contains almost no water or by-products.
By adding an alkylene oxide to this under pressure, a high-purity and high-quality fatty acid amide ether can be produced. The use of fatty acids, which are cheaper than fatty acid methyl esters, is economically superior.
【００１８】本発明に用いられるアルキレンオキサイド
は炭素数２〜３のアルキレンオキサイド、即ちエチレン
オキサイド、プロピレンオキサイド（以下それぞれをＥ
Ｏ,ＰＯという）のいずれか、もしくはその双方の混合
物である。アルキレンオキサイドの付加反応は、例え
ば、0.2〜10.0Paの加圧下で80〜130℃で行えばよい。The alkylene oxide used in the present invention is an alkylene oxide having 2 to 3 carbon atoms, that is, ethylene oxide and propylene oxide.
O, PO) or a mixture of both. The addition reaction of the alkylene oxide may be performed, for example, at 80 to 130 ° C. under a pressure of 0.2 to 10.0 Pa.
【００１９】本発明の方法により得られる脂肪酸アミド
エーテルには、下記一般式（Ｉ）で表されるものが挙げ
られる。The fatty acid amide ether obtained by the method of the present invention includes those represented by the following general formula (I).
【００２０】[0020]
【化３】 Embedded image
【００２１】〔式中、R は炭素数５〜21、好ましくは５
〜13の直鎖もしくは分岐鎖のアルキル基又はアルケニル
基、A は炭素数２〜３のアルキレン基、n はアルキレン
オキサイドの平均付加モル数を示す０を超え30以下の
数、X は水素原子又は炭素数１〜３の直鎖又は分岐鎖の
アルキル基、好ましくは水素原子又はメチル基、W は水
素原子、炭素数１〜３の直鎖又は分岐鎖のアルキル基、
あるいは式 -B-O-(AO)m-H（ここで Aは前記の意味を示
し、B は炭素数１〜３の直鎖又は分岐鎖のアルキレン
基、m はアルキレンオキサイドの平均付加モル数を示す
０を超え30以下の数である。）で表される基、好ましく
は水素原子を示す。〕[Wherein, R is a group having 5 to 21 carbon atoms, preferably 5 to 21 carbon atoms.
~ 13 linear or branched alkyl or alkenyl groups, A is an alkylene group having 2 to 3 carbon atoms, n is an average number of moles of alkylene oxide which is more than 0 and 30 or less, X is a hydrogen atom or A linear or branched alkyl group having 1 to 3 carbon atoms, preferably a hydrogen atom or a methyl group, W is a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms,
Or a formula -BO- (AO) m -H (where A represents the above-mentioned meaning, B represents a linear or branched alkylene group having 1 to 3 carbon atoms, and m represents an average addition mole number of the alkylene oxide. A number greater than 0 and not more than 30), preferably a hydrogen atom. ]
【００２２】[0022]
【実施例】以下の実施例において脂肪酸アルカノールア
ミド及び脂肪酸アミドエーテルの純度は液体クロマトグ
ラフィ（UV検出器、Cica-MERCK RP-18型カラム）によっ
て測定し、ピーク面積値と検量線から求めた。EXAMPLES In the following examples, the purity of fatty acid alkanolamides and fatty acid amide ethers was measured by liquid chromatography (UV detector, Cica-MERCK RP-18 type column) and determined from the peak area value and the calibration curve.
【００２３】実施例１ 反応容器にラウリン酸 200ｇ(1.0モル）を仕込み、180
℃まで昇温した後、モノエタノールアミン67ｇ(1.1モ
ル）を添加時間２時間で生成する水を除去しながら反応
させ、続いてさらに熟成時間４時間で反応を熟成させ
た。冷却後、温度が100 ℃以下になったときにナトリウ
ムメチラート２ｇを添加し30分撹拌した後、未反応モノ
エタノールアミンを減圧除去し、反応生成物を得た。こ
のラウリン酸モノエタノールアミドの純度は98.7％であ
った。これにＥＯ88ｇを加え、オートクレーブ中で反応
温度 110℃で１時間反応させ、ラウリン酸モノエタノー
ルアミドのＥＯ付加物（ｎ（平均付加モル数）＝２）を
得た。この純度は 95.8 ％であった。Example 1 A reaction vessel was charged with 200 g (1.0 mol) of lauric acid,
After the temperature was raised to 70 ° C., 67 g (1.1 mol) of monoethanolamine was reacted while removing water generated in an addition time of 2 hours, followed by aging the reaction for an additional aging time of 4 hours. After cooling, when the temperature became 100 ° C. or less, 2 g of sodium methylate was added and stirred for 30 minutes, and then unreacted monoethanolamine was removed under reduced pressure to obtain a reaction product. The purity of this lauric acid monoethanolamide was 98.7%. 88 g of EO was added thereto and reacted in an autoclave at a reaction temperature of 110 ° C. for 1 hour to obtain an EO adduct of lauric acid monoethanolamide (n (average number of moles added) = 2). Its purity was 95.8%.
【００２４】実施例２ モノエタノールアミン67ｇ(1.1モル）をイソプロパノー
ルアミン81ｇ(1.1モル）に、熟成時間４時間を５時間
に、ＥＯ88ｇを132 ｇに、オートクレーブでの反応温度
110 ℃を120 ℃に変えた以外は実施例１と同様の条件で
反応させた。アミド化反応の生成物であるラウリン酸イ
ソプロパノールアミドの純度は98.2％、ＥＯ付加反応の
生成物であるラウリン酸イソプロパノールアミドのＥＯ
付加物（ｎ＝３）の純度は 94.9 ％であった。EXAMPLE 2 67 g (1.1 mol) of monoethanolamine was added to 81 g (1.1 mol) of isopropanolamine, aging time was 4 hours to 5 hours, 88 g of EO was 132 g, reaction temperature in an autoclave.
The reaction was carried out under the same conditions as in Example 1 except that 110 ° C. was changed to 120 ° C. The purity of lauric acid isopropanolamide as a product of the amidation reaction is 98.2%, and the EO of lauric acid isopropanolamide as a product of the EO addition reaction is EO.
The purity of the adduct (n = 3) was 94.9%.
【００２５】実施例３ 添加時間２時間を１時間に、熟成時間４時間を３時間
に、オートクレーブでの反応温度110 ℃を120 ℃に変
え、ナトリウムメチラートを添加しなかった以外は実施
例１と同様の条件で反応させた。アミド化反応の生成物
であるラウリン酸モノエタノールアミドの純度は97.1
％、ＥＯ付加反応の生成物であるラウリン酸モノエタノ
ールアミドのＥＯ付加物（ｎ＝２）の純度は 94.0 ％で
あった。Example 3 Example 1 was repeated except that the addition time was changed from 2 hours to 1 hour, the aging time from 4 hours to 3 hours, the reaction temperature in the autoclave from 110 ° C. to 120 ° C., and sodium methylate was not added. The reaction was carried out under the same conditions as described above. The product of the amidation reaction, lauric acid monoethanolamide, has a purity of 97.1.
%, The purity of the EO adduct of lauric acid monoethanolamide (n = 2) as a product of the EO addition reaction was 94.0%.
【００２６】実施例４ モノエタノールアミン67ｇ(1.1モル）を62.3ｇ(1.02 モ
ル）に、添加時間２時間を１時間に、オートクレーブで
の反応温度110 ℃を120 ℃に変えた以外は実施例１と同
様の条件で反応させた。アミド化反応の生成物であるラ
ウリン酸モノエタノールアミドの純度は98.6％、ＥＯ付
加反応の生成物であるラウリン酸モノエタノールアミド
のＥＯ付加物（ｎ＝２）の純度は 95.9 ％であった。Example 4 Example 1 was repeated except that 67 g (1.1 mol) of monoethanolamine was added to 62.3 g (1.02 mol), the addition time was changed from 2 hours to 1 hour, and the autoclave reaction temperature was changed from 110 ° C. to 120 ° C. Reaction was carried out under the same conditions as in The product of the amidation reaction, lauric acid monoethanolamide, had a purity of 98.6%, and the product of the EO addition reaction, EO adduct of lauric acid monoethanolamide (n = 2), had a purity of 95.9%.
【００２７】実施例５ 反応容器にミリスチン酸 228ｇ(1.0モル）を仕込み、20
0 ℃まで昇温した後、モノエタノールアミン73ｇ(1.2モ
ル）を３時間かけて生成する水を除去しながら添加し反
応させ、続いてさらに３時間かけて反応を熟成させた。
冷却後、温度が100 ℃以下になったときにナトリウムメ
チラート２ｇを添加し30分撹拌した後、未反応のモノエ
タノールアミンを減圧除去し、反応生成物を得た。この
ミリスチン酸モノエタノールアミドの純度は98.2％であ
った。これにＰＯ 116ｇを加え、オートクレーブ中で 1
30℃、２時間反応させ、ミリスチン酸モノエタノールア
ミドのＰＯ付加物（ｎ＝２）を得た。この純度は 95.2
％であった。Example 5 A reaction vessel was charged with 228 g (1.0 mol) of myristic acid.
After the temperature was raised to 0 ° C., 73 g (1.2 mol) of monoethanolamine was added thereto over 3 hours while removing formed water, followed by a reaction, followed by aging of the reaction for another 3 hours.
After cooling, when the temperature became 100 ° C. or lower, 2 g of sodium methylate was added and stirred for 30 minutes, and unreacted monoethanolamine was removed under reduced pressure to obtain a reaction product. The purity of this myristic acid monoethanolamide was 98.2%. Add 116g of PO to this, and in an autoclave 1
The mixture was reacted at 30 ° C. for 2 hours to obtain a PO adduct of myristic acid monoethanolamide (n = 2). This purity is 95.2
%Met.
【００２８】比較例１ 反応容器にラウリン酸 200ｇ(1.0モル）とモノエタノー
ルアミン61ｇ(1.0モル）を一括して仕込み、生成する水
を除去しながら180 ℃で５時間反応させた。冷却後、温
度が100 ℃以下になったときにナトリウムメチラート２
ｇを添加し30分撹拌した後、未反応のモノエタノールア
ミンを減圧除去し、反応生成物を得た。このラウリン酸
モノエタノールアミドの純度は91.1％であった。これに
ＥＯ88ｇを加え、オートクレーブ中で 100℃、２時間反
応させ、ラウリン酸モノエタノールアミドのＥＯ付加物
（ｎ＝２）を得た。この純度は 83.9 ％であった。Comparative Example 1 A reaction vessel was charged with 200 g (1.0 mol) of lauric acid and 61 g (1.0 mol) of monoethanolamine all at once, and reacted at 180 ° C. for 5 hours while removing generated water. After cooling, when the temperature drops below 100 ° C, sodium methylate 2
After adding g and stirring for 30 minutes, unreacted monoethanolamine was removed under reduced pressure to obtain a reaction product. The purity of this lauric acid monoethanolamide was 91.1%. 88 g of EO was added thereto and reacted in an autoclave at 100 ° C. for 2 hours to obtain an EO adduct of lauric acid monoethanolamide (n = 2). Its purity was 83.9%.
【００２９】上記実施例１〜５で製造した脂肪酸アミド
エーテルは高純度なものであり、これらは安価な原料で
ある脂肪酸から製造したにも関わらず、高品質であっ
た。The fatty acid amide ethers produced in Examples 1 to 5 were of high purity, and were of high quality despite being produced from fatty acids which were inexpensive raw materials.
【００３０】[0030]
【発明の効果】本発明の脂肪酸アミドエーテルの製造方
法によれば、安価な脂肪酸を原料として用い、反応時間
が短く、脂肪酸に対するアルカノールアミンのモル比を
低減でき、脂肪酸アミドエーテルを効率良く高純度で製
造することができる。According to the method for producing a fatty acid amide ether of the present invention, an inexpensive fatty acid is used as a raw material, the reaction time is short, the molar ratio of alkanolamine to the fatty acid can be reduced, and the fatty acid amide ether can be efficiently purified with high purity. Can be manufactured.
─────────────────────────────────────────────────────
────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成１１年１月６日[Submission date] January 6, 1999
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】特許請求の範囲[Correction target item name] Claims
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【特許請求の範囲】[Claims]
【化１】 〔式中、R は炭素数５〜21の直鎖もしくは分岐鎖のアル
キル基又はアルケニル基、A は炭素数２〜３のアルキレ
ン基、n はアルキレンオキサイドの平均付加モル数を示
す０を超え30以下の数、X は水素原子又は炭素数１〜３
の直鎖又は分岐鎖のアルキル基、W は水素原子、炭素数
１〜３の直鎖又は分岐鎖のアルキル基、あるいは式 -B
-O-(AO)m-H（ここで Aは前記の意味を示し、B は炭素数
１〜３の直鎖又は分岐鎖のアルキレン基、m はアルキレ
ンオキサイドの平均付加モル数を示す０を超え30以下の
数である。）で表される基を示す。〕Embedded image [Wherein, R is a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, and n is an average number of added alkylene oxide moles of more than 0 and 30 or more. The following number, X is a hydrogen atom or carbon number 1-3
Linear or branched alkyl group, W is hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms or an expression -B,
-O- (AO) m -H (where A represents the above-mentioned meaning, B represents a linear or branched alkylene group having 1 to 3 carbon atoms, and m represents 0 representing the average number of moles of alkylene oxide added. beyond showing a group represented by 30 is the number below.). ]
【請求項４】 脂肪酸中にアルカノールアミンを添加し
ながら反応させる際の温度が 150〜250 ℃である請求項
１〜３のいずれか一項に記載の製造法。 4. A process according to any one of claims 1 to 3 Temperature of time of the reaction with the addition of alkanolamine in the fatty acid is 150 to 250 ° C..
【請求項５】 脂肪酸とアルカノールアミンとの反応モ
ル比がアルカノールアミン／脂肪酸＝0.9 〜1.2 である
請求項１〜４のいずれか一項に記載の製造法。 ─────────────────────────────────────────────────────
5. A fatty acid and process according to any one of claims 1-4 reaction molar ratio of alkanolamine is an alkanolamine / fatty acid = 0.9 to 1.2. ────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成１１年８月２日[Submission date] August 2, 1999
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】特許請求の範囲[Correction target item name] Claims
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【特許請求の範囲】[Claims]
【化１】 〔式中、R は炭素数５〜21の直鎖もしくは分岐鎖のアル
キル基又はアルケニル基、A は炭素数２〜３のアルキレ
ン基、n はアルキレンオキサイドの平均付加モル数を示
す０を超え30以下の数、X は水素原子又は炭素数１〜３
の直鎖又は分岐鎖のアルキル基、W は水素原子、炭素数
１〜３の直鎖又は分岐鎖のアルキル基、あるいは式 -B
-O-(AO)m-H（ここで Aは前記の意味を示し、B は炭素数
１〜３の直鎖又は分岐鎖のアルキレン基、m はアルキレ
ンオキサイドの平均付加モル数を示す０を超え30以下の
数である。）で表される基を示す。〕Embedded image [Wherein, R is a linear or branched alkyl group or alkenyl group having 5 to 21 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, and n is an average number of added moles of alkylene oxide. The following number, X is a hydrogen atom or carbon number 1-3
W is a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, or a compound of the formula -B
-O- (AO) m -H (where A represents the above-mentioned meaning, B represents a linear or branched alkylene group having 1 to 3 carbon atoms, and m represents 0 representing the average number of moles of alkylene oxide added. Greater than 30). ]
【請求項４】 脂肪酸とアルカノールアミンとの反応モ
ル比がアルカノールアミン／脂肪酸＝0.9 〜1.2 である
請求項１〜３のいずれか一項に記載の製造法。 4. A fatty acid and process according to any one of claims 1 to 3 reaction molar ratio of the alkanolamine is an alkanolamine / fatty acid = 0.9 to 1.2.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 鐵 真希男 和歌山県和歌山市湊1334 花王株式会社研 究所内 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Makio Tetsu 1334 Minato, Wakayama-shi, Wakayama Pref.
Claims (6)
ながら反応させて脂肪酸アルカノールアミドを製造し、
次いでアルキレンオキサイドを付加させる脂肪酸アミド
エーテルの製造法。1. A fatty acid alkanolamide is produced by reacting a fatty acid while adding an alkanolamine to the fatty acid,
Then, a method for producing a fatty acid amide ether to which an alkylene oxide is added.
で表される化合物である請求項１記載の製造法。 【化１】 〔式中、R は炭素数５〜21、好ましくは５〜13の直鎖も
しくは分岐鎖のアルキル基又はアルケニル基、A は炭素
数２〜３のアルキレン基、n はアルキレンオキサイドの
平均付加モル数を示す０を超え30以下の数、X は水素原
子又は炭素数１〜３の直鎖又は分岐鎖のアルキル基、好
ましくは水素原子又はメチル基、W は水素原子、炭素数
１〜３の直鎖又は分岐鎖のアルキル基、あるいは式 -B
-O-(AO)m-H（ここで Aは前記の意味を示し、B は炭素数
１〜３の直鎖又は分岐鎖のアルキレン基、m はアルキレ
ンオキサイドの平均付加モル数を示す０を超え30以下の
数である。）で表される基、好ましくは水素原子を示
す。〕2. The fatty acid amide ether has the general formula (I)
The method according to claim 1, which is a compound represented by the formula: Embedded image [Wherein, R is a linear or branched alkyl or alkenyl group having 5 to 21, preferably 5 to 13 carbon atoms, A is an alkylene group having 2 to 3 carbon atoms, and n is the average number of moles of alkylene oxide added. X is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, preferably a hydrogen atom or a methyl group, and W is a hydrogen atom or a straight chain having 1 to 3 carbon atoms. A chain or branched alkyl group, or a compound of the formula -B
-O- (AO) m -H (where A represents the above-mentioned meaning, B represents a linear or branched alkylene group having 1 to 3 carbon atoms, and m represents 0 representing the average number of moles of alkylene oxide added. A number of more than 30 or less), preferably a hydrogen atom. ]
４時間、好ましくは１〜３時間である請求項１又は２記
載の製造法。3. The addition time of the alkanolamine is 0.5 to 0.5.
The process according to claim 1 or 2, wherein the time is 4 hours, preferably 1 to 3 hours.
ながら反応させる際の圧力が常圧である請求項１〜３の
いずれか一項に記載の製造法。4. The production method according to claim 1, wherein the pressure during the reaction while adding the alkanolamine to the fatty acid is normal pressure.
ながら反応させる際の温度が 150〜250 ℃、好ましくは
160 〜200 ℃である請求項１〜４のいずれか一項に記載
の製造法。5. The temperature at the time of reacting while adding alkanolamine to the fatty acid is 150 to 250 ° C., preferably
The method according to any one of claims 1 to 4, wherein the temperature is 160 to 200 ° C.
ル比がアルカノールアミン／脂肪酸＝0.9 〜1.2 である
請求項１〜５のいずれか一項に記載の製造法。6. The process according to claim 1, wherein the reaction molar ratio of the fatty acid to the alkanolamine is alkanolamine / fatty acid = 0.9 to 1.2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10139790A JP2995036B2 (en) | 1998-05-21 | 1998-05-21 | Method for producing fatty acid amide ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10139790A JP2995036B2 (en) | 1998-05-21 | 1998-05-21 | Method for producing fatty acid amide ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11335340A true JPH11335340A (en) | 1999-12-07 |
| JP2995036B2 JP2995036B2 (en) | 1999-12-27 |
Family
ID=15253497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10139790A Expired - Fee Related JP2995036B2 (en) | 1998-05-21 | 1998-05-21 | Method for producing fatty acid amide ether |
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| Country | Link |
|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006316277A (en) * | 2005-05-13 | 2006-11-24 | Chevron Oronite Co Llc | Fuel composition containing alkylene oxide-added hydrocarbon amide having small amine by-product content |
| JP2006315977A (en) * | 2005-05-11 | 2006-11-24 | Lion Corp | Method for producing polyoxyalkylene alkanolamide |
| CN112778119A (en) * | 2021-01-13 | 2021-05-11 | 杭州洁汉化工有限公司 | Green aqueous phase solvent-free high-purity synthesis method of palmitoylethanolamide |
-
1998
- 1998-05-21 JP JP10139790A patent/JP2995036B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006315977A (en) * | 2005-05-11 | 2006-11-24 | Lion Corp | Method for producing polyoxyalkylene alkanolamide |
| JP2006316277A (en) * | 2005-05-13 | 2006-11-24 | Chevron Oronite Co Llc | Fuel composition containing alkylene oxide-added hydrocarbon amide having small amine by-product content |
| JP2012255175A (en) * | 2005-05-13 | 2012-12-27 | Chevron Oronite Co Llc | Fuel composition containing alkylene oxide-adducted hydrocarbyl amide having reduced amine by-products |
| CN112778119A (en) * | 2021-01-13 | 2021-05-11 | 杭州洁汉化工有限公司 | Green aqueous phase solvent-free high-purity synthesis method of palmitoylethanolamide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2995036B2 (en) | 1999-12-27 |
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