JP2006199650A - Method for producing 7,8-epoxy-1-octanol - Google Patents
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本発明は７−オクテン−１−オールを実質的に水を含まない過酢酸によりエポキシ化することによる７，８−エポキシ−１−オクタノールの製造方法に関する。 The present invention relates to a process for producing 7,8-epoxy-1-octanol by epoxidizing 7-octen-1-ol with peracetic acid substantially free of water.
エポキシアルコール類の製造方法としては、過酸化水素水を用いる系が知られており、例えば、β、γ−不飽和アルコール類をタングステン酸塩および４級アンモニウム塩の存在下に過酸化水素でエポキシ化することにより、対応するエポキシアルコール類が生成することが知られている（特許文献１参照）。しかしこの特許文献１には、炭化水素鎖末端に不飽和二重結合を有する７−オクテン−１−オールから対応するエポキシアルコールである７，８−エポキシ−１−オクタノールを製造することについては記載されていない。また、過酸化水素のみでは反応性が低いので、上記過酸化水素を用いる系においては各種金属錯体等の触媒を必要としている。 As a method for producing epoxy alcohols, a system using hydrogen peroxide water is known. For example, β, γ-unsaturated alcohols are epoxyated with hydrogen peroxide in the presence of tungstate and quaternary ammonium salts. It is known that corresponding epoxy alcohols are produced by conversion (see Patent Document 1). However, this Patent Document 1 describes the production of 7,8-epoxy-1-octanol, which is a corresponding epoxy alcohol, from 7-octen-1-ol having an unsaturated double bond at the end of the hydrocarbon chain. It has not been. In addition, since hydrogen peroxide alone has low reactivity, a catalyst such as various metal complexes is required in the system using hydrogen peroxide.
また、炭化水素鎖末端に不飽和二重結合を有する１級アルコール類から有機過カルボン酸を用いて対応するエポキシアルコール類を製造する方法として、メタクロロ過安息香酸を使用したエポキシアルコール類の合成例が知られている（非特許文献１）。しかし、メタクロロ過安息香酸以外の酸化剤についての記載はなく、また、酸化剤として用いるメタクロロ安息香酸が高価であるという問題点がある上、塩素分等が微量な不純物として生成物のエポキシアルコール類に混入してくる場合がある。 In addition, as a method for producing a corresponding epoxy alcohol from a primary alcohol having an unsaturated double bond at the end of a hydrocarbon chain using an organic percarboxylic acid, an example of synthesis of an epoxy alcohol using metachloroperbenzoic acid Is known (Non-Patent Document 1). However, there is no description about oxidizing agents other than metachloroperbenzoic acid, and there is a problem that metachlorobenzoic acid used as an oxidizing agent is expensive, and epoxy alcohols of products as impurities such as a small amount of chlorine May come in.
本発明の目的は高収率で、７，８−エポキシ−１−オクタノールを工業的に有利に製造する方法を提供することである。
本発明者は、前記目的を達成するために鋭意検討した結果、７−オクテン−１−オールを実質的に水を含まない過酢酸を用いてエポキシ化することにより、７，８−エポキシ−１−オクタノールを収率よく高純度で得られることを見出し、本発明を完成するに至った。
The object of the present invention is to provide a process for producing 7,8-epoxy-1-octanol industrially advantageously in high yield.
As a result of intensive studies to achieve the above object, the present inventor epoxidized 7-octen-1-ol with peracetic acid substantially free of water, thereby producing 7,8-epoxy-1. The inventors have found that octanol can be obtained with high yield and high purity, and have completed the present invention.
すなわち、本発明の第１は、７−オクテン−１−オールを、実質的に水を含まない過酢酸によりエポキシ化することを特徴とする７，８−エポキシ−１−オクタノールの製造方法である。
また本発明の第２は、過酢酸中の水分が０．８質量％以下である本発明の第１の７，８−エポキシ−１−オクタノールの製造方法である。
また本発明の第３は、過酢酸が酢酸エチル溶液である本発明の第２の７，８−エポキシ−１−オクタノールの製造方法である。
That is, the first of the present invention is a process for producing 7,8-epoxy-1-octanol, characterized in that 7-octen-1-ol is epoxidized with peracetic acid substantially free of water. .
A second aspect of the present invention is the first method for producing 7,8-epoxy-1-octanol according to the present invention, wherein the water content in peracetic acid is 0.8% by mass or less.
The third aspect of the present invention is the second method for producing 7,8-epoxy-1-octanol according to the present invention, wherein peracetic acid is an ethyl acetate solution.
本発明によれば、７−オクテン−１−オールから、安価に収率よく、かつ高純度で、７，８−エポキシ−１−オクタノールを製造することができる。 According to the present invention, 7,8-epoxy-1-octanol can be produced from 7-octen-1-ol at low cost with high yield and high purity.
＜過酢酸＞
本発明でエポキシ化剤として使用する過酢酸は、実質的に水を含まないものであれば特に限定されない。具体的には、水分含有量０．８質量％以下、好ましくは０．６質量％以下の過酢酸を使用することが、高い選択率および転化率で目的とする７，８−エポキシ−１−オクタノールが得られるという点で好ましい。本発明でいう実質的に水分を含まない過酢酸は、アルデヒド類、例えば、アセトアルデヒドの空気または酸素酸化により製造されるものであり、例えば、過酢酸についてはドイツ公開特許公報１４１８４６５号や特開昭５４−３００６号公報に記載された方法により製造される。これらの方法によれば、過酸化水素と酢酸から過酢酸を合成し、溶媒により過酢酸を抽出する方法に比べて連続して大量に高濃度の過酢酸を合成できるために、安価に得ることができるので、好ましい。
<Peracetic acid>
The peracetic acid used as an epoxidizing agent in the present invention is not particularly limited as long as it does not substantially contain water. Specifically, the use of peracetic acid having a water content of 0.8% by mass or less, preferably 0.6% by mass or less is aimed at high selectivity and conversion, and 7,8-epoxy-1- Octanol is preferred in that it is obtained. The substantially acetic acid-free peracetic acid referred to in the present invention is produced by air or oxygen oxidation of aldehydes such as acetaldehyde. For example, peracetic acid is disclosed in German Patent Publication No. 1418465 and It is produced by the method described in Japanese Patent No. 54-3006. According to these methods, it is possible to synthesize peracetic acid from hydrogen peroxide and acetic acid and to synthesize peracetic acid in a large amount continuously compared to the method of extracting peracetic acid with a solvent. Is preferable.
７，８−エポキシ−１−オクタノールを高い選択率および転化率で合成するためには、７−オクテン−１−オール１モルに対する過酢酸の使用量は、好ましくは１．０〜３．０モル、より好ましくは１．０５〜１．５モルである。経済性及び副反応の問題から、３．０倍モルを超えることは通常不利である。本発明の製造方法によれば、高価なエポキシ化剤や触媒を使用する必要はない。 In order to synthesize 7,8-epoxy-1-octanol with high selectivity and conversion, the amount of peracetic acid used per mole of 7-octen-1-ol is preferably 1.0 to 3.0 moles. More preferably, it is 1.05-1.5 mol. From the viewpoint of economy and side reaction, it is usually disadvantageous to exceed 3.0 times mole. According to the production method of the present invention, it is not necessary to use an expensive epoxidizing agent or catalyst.
エポキシ化反応においては、装置や反応条件に応じて、溶媒を使用してもよい。
溶媒は過酢酸の希釈による安定化などの目的で使用することができ、溶媒比率を上げることでエポキシ化反応の際に過酢酸から発生する酢酸の濃度を下げることができるので、酢酸によるエポキシ環の開環反応が防止しやすくなる。溶媒を使用する場合、その使用量は過酢酸１００質量部に対して通常、２０〜５００質量部である。溶媒の使用量が５００質量部より多いと、エポキシ化反応が進まず、収率が低くなる傾向となり、逆に、２０質量部より少ない場合、使用する意味が殆どない。
溶媒の種類としては、エステル類、脂肪族または芳香族炭化水素類、エーテル類などを用いることができる。特に好ましい溶媒は、酢酸エチル、ヘキサン、シクロヘキサン、トルエン、ベンゼン等であり、とりわけ、酢酸エチルが好ましい。
In the epoxidation reaction, a solvent may be used depending on the apparatus and reaction conditions.
The solvent can be used for the purpose of stabilization by diluting peracetic acid, and by increasing the solvent ratio, the concentration of acetic acid generated from peracetic acid during the epoxidation reaction can be lowered. It is easy to prevent the ring-opening reaction. When using a solvent, the usage-amount is 20-500 mass parts normally with respect to 100 mass parts of peracetic acid. When the amount of the solvent used is more than 500 parts by mass, the epoxidation reaction does not proceed and the yield tends to be low. Conversely, when the amount is less than 20 parts by mass, there is little meaning to use.
As the kind of the solvent, esters, aliphatic or aromatic hydrocarbons, ethers and the like can be used. Particularly preferred solvents are ethyl acetate, hexane, cyclohexane, toluene, benzene and the like, and ethyl acetate is particularly preferred.
エポキシ化反応温度は、７−オクテン−１−オールに対する過酢酸の反応性によって定まる。反応温度は２０〜１００℃、好ましくは３０〜７０℃、より好ましくは４５〜５５℃である。２０℃未満では反応が遅く、１００℃を超える温度では過酢酸が発熱を伴って分解するので、好ましくない。 The epoxidation reaction temperature is determined by the reactivity of peracetic acid to 7-octen-1-ol. The reaction temperature is 20 to 100 ° C, preferably 30 to 70 ° C, more preferably 45 to 55 ° C. If it is less than 20 ° C., the reaction is slow, and if it exceeds 100 ° C., peracetic acid decomposes with heat generation, which is not preferable.
エポキシ化反応は、７−オクテン−１−オールおよび必要に応じて溶媒を反応器に仕込み、所定温度範囲に保ちながら過酢酸を滴下などの方法で逐次添加して行なうことが好ましい。また、上記のエポキシ化反応は連続式に行ってもよい。
本発明では、エポキシ化反応に特別な操作は必要なく、例えば過酢酸を滴下終了後、反応粗液を１〜１０時間攪拌して反応および熟成させればよい。
The epoxidation reaction is preferably carried out by adding 7-octen-1-ol and, if necessary, a solvent to the reactor and successively adding peracetic acid by a method such as dropwise addition while maintaining the temperature within a predetermined temperature range. The epoxidation reaction may be performed continuously.
In the present invention, no special operation is required for the epoxidation reaction. For example, after the completion of dropwise addition of peracetic acid, the reaction crude liquid may be stirred and reacted and aged for 1 to 10 hours.
得られた反応粗液からの７，８−エポキシ−１−オクタノールの単離は、適当な方法、たとえば、反応粗液中に含まれている未反応の過酢酸および過酢酸から生成した酢酸等を水で抽出し、水層から分離された有機層を蒸留して溶媒を留去することにより行うことができる。さらに、未反応の７−オクテン−１−オールは、これが目的の７，８−エポキシ−１−オクタノールよりも低沸点であることから、溶媒と同様に留去して回収することができる。 Isolation of 7,8-epoxy-1-octanol from the obtained reaction crude liquid is carried out by an appropriate method such as unreacted peracetic acid and acetic acid produced from peracetic acid contained in the reaction crude liquid. Is extracted with water, and the organic layer separated from the aqueous layer is distilled to distill off the solvent. Furthermore, since unreacted 7-octen-1-ol has a lower boiling point than the intended 7,8-epoxy-1-octanol, it can be recovered by distillation in the same manner as the solvent.
反応および熟成終了後、反応粗液は最初に高濃度の苛性ソーダ水溶液などのアルカリにて中和洗浄を行うことが好ましい。すなわち、苛性ソーダ水溶液を用いると過酢酸から生じた酢酸との中和反応により酢酸ソーダが生成し、酢酸ソーダが緩衝剤的に作用する他、酢酸ソーダ水溶液層側の比重が上がるので、７，８−エポキシ−１−オクタノールの有機層との比重差が大きくなり、分液性がよくなるという副次的効果がある。この中和洗浄および分液を行った後、７，８−エポキシ−１−オクタノールを含有する有機層中に残存している酢酸ソーダを水にて洗浄して除去し、次いで溶媒を蒸留除去することが好ましい。さらに、生成した目的生成物である７，８−エポキシ−１−オクタノールのエポキシ基に過酢酸から生じた酢酸が付加する副反応でアセトキシヒドロキシアルコール類を生じることがあるが、これは目的生成物である７，８−エポキシ−１−オクタノールより高沸点であることから蒸留により除去することができる。 After completion of the reaction and aging, the reaction crude liquid is preferably first neutralized and washed with an alkali such as a high-concentration caustic soda aqueous solution. That is, when caustic soda aqueous solution is used, sodium acetate is generated by neutralization reaction with acetic acid generated from peracetic acid, so that sodium acetate acts as a buffer, and the specific gravity of the sodium acetate aqueous solution layer side is increased. -The specific gravity difference with the organic layer of epoxy-1-octanol becomes large, and there exists a secondary effect that liquid separation property becomes good. After this neutralization washing and liquid separation, sodium acetate remaining in the organic layer containing 7,8-epoxy-1-octanol is removed by washing with water, and then the solvent is distilled off. It is preferable. Furthermore, a side reaction in which acetic acid generated from peracetic acid is added to the epoxy group of 7,8-epoxy-1-octanol, which is the generated target product, may produce acetoxyhydroxy alcohols. Since it has a boiling point higher than that of 7,8-epoxy-1-octanol, it can be removed by distillation.
本発明の製造方法では、従来の過酸化水素によるエポキシ化反応のように各種金属触媒等を必ずしも併用する必要はないが、必要に応じて触媒を用いることもできる。 In the production method of the present invention, it is not always necessary to use various metal catalysts or the like as in the conventional epoxidation reaction with hydrogen peroxide, but a catalyst may be used as necessary.
（実施例）
以下、実施例により本発明を具体的に説明するが、本発明はこれらに限定されるものではない。
(Example)
EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.
（実施例１）
反応器に、１−オクタノールを１２％含む７−オクテン−１−オール３００ｇ、酢酸エチル３００ｇを仕込み、窒素を気相部に吹き込みながら、かつ、反応系内の温度を５０℃になるようにコントロールしながら、過酢酸を３０質量％含む酢酸エチル溶液（水分０．４１質量％）６０６ｇを、約２時間かけて滴下した。過酢酸溶液滴下終了後、５０℃で７時間攪拌しながら熟成し反応を終了した。
次いで、反応粗液に、３０℃以下の攪拌状態で、１０％苛性ソーダ水溶液６０２ｇを加え、攪拌を止めて２層に分離させ、下層の水層を分離除去した。この操作を２回繰り返した後に、上層の有機層に対して５０１ｇの脱イオン水を加え、残存する中和塩を洗浄除去した。
洗浄済みの粗液から、７０℃／２６６６Ｐａで溶媒、酢酸などの低沸点化合物の除去を行い、残留液２２５．０ｇを得た。
得られた残留液をＧＣにて組成分析すると７，８−エポキシ−１−オクタノール７９．７％、２，８−ジヒドロキシオクタン−１−オール酢酸エステル、１．４％、７−オクテン−１−オール７．２％、１−オクタノール１１．７％であった（７−オクテン−１−オールの７，８−エポキシ−１−オクタノールへの選択率は６４．３％、７，８−エポキシ−１−オクタノールの収率は６０．４％）。
図１に原料の７−オクテン−１−オール、図２に得られた留出液の各1Ｈ−ＮＭＲスペクトルを示す（横軸はδ値、縦軸はシグナル強度を示す）。1Ｈ−ＮＭＲ測定は溶媒としてＣＤＣｌ３を用いて、内部標準ＴＭＳで行なった。原料の７−オクテン−１−オールに見られたδ４．８およびδ５．６付近の末端二重結合に由来するピークが減少し、δ２．３〜δ３．０付近にエポキシ基に由来するプロトンのピークが確認され、上記残留液の大部分が目的生成物である７，８−エポキシ−１−オクタノールであることが確認された。
Example 1
A reactor was charged with 300 g of 7-octen-1-ol containing 12% of 1-octanol and 300 g of ethyl acetate, and nitrogen was blown into the gas phase and the temperature in the reaction system was controlled to 50 ° C. Then, 606 g of an ethyl acetate solution (water content 0.41% by mass) containing 30% by mass of peracetic acid was dropped over about 2 hours. After the peracetic acid solution was dropped, the reaction was terminated by aging with stirring at 50 ° C. for 7 hours.
Next, 602 g of a 10% sodium hydroxide aqueous solution was added to the reaction crude liquid with stirring at 30 ° C. or lower, stirring was stopped and the two aqueous layers were separated, and the lower aqueous layer was separated and removed. After repeating this operation twice, 501 g of deionized water was added to the upper organic layer, and the remaining neutralized salt was washed away.
Low-boiling compounds such as solvent and acetic acid were removed from the washed crude liquid at 70 ° C./2666 Pa to obtain 225.0 g of a residual liquid.
When the composition of the obtained residual liquid was analyzed by GC, 7,9.7-epoxy-1-octanol 79.7%, 2,8-dihydroxyoctane-1-ol acetate, 1.4%, 7-octene-1- The total was 7.2% and 1-octanol was 11.7% (selectivity of 7-octen-1-ol to 7,8-epoxy-1-octanol was 64.3%, 7,8-epoxy- The yield of 1-octanol is 60.4%).
FIG. 1 shows the raw material 7-octen-1-ol, and FIG. 2 shows 1 H-NMR spectra of the distillate obtained (the horizontal axis indicates the δ value, and the vertical axis indicates the signal intensity). 1 H-NMR measurement was performed with internal standard TMS using CDCl 3 as a solvent. The peaks derived from the terminal double bonds near δ4.8 and δ5.6 observed in the starting 7-octen-1-ol decreased, and the protons derived from the epoxy group near δ2.3 to δ3.0. A peak was confirmed, and it was confirmed that most of the residual liquid was 7,8-epoxy-1-octanol, which was the target product.
（実施例２）
反応器に、１−オクタノールを３％含む７−オクテン−１−オール３００ｇ及び酢酸エチル３００ｇを仕込み、窒素を気相部に吹き込みながら、かつ、反応系内の温度を６０℃になるようにコントロールしながら約４時間かけて過酢酸を３０質量％含む酢酸エチル溶液（水分率０．４１質量％）６３３ｇを滴下した。過酢酸溶液滴下終了後、６０℃で３時間攪拌しながら熟成し反応を終了した。
次いで、反応粗液に、３０℃以下の攪拌状態で、１０％苛性ソーダ水溶液６０３ｇを加え、攪拌を止めて２層分離し、下層の水層を分離除去した。この操作を３回繰り返した後に、上層の有機層に対して４００ｇの脱イオン水を加え、残存する中和塩を洗浄除去した。
洗浄済みの粗液から、７０℃／２６６６Ｐａで低沸点化合物の除去を行い、残留液２７８．５ｇを得た。
得られた残留液をＧＣにて組成分析すると７，８−エポキシ−１−オクタノール８９．４％、２，８−ジヒドロキシオクタン−１−オール酢酸エステル０．９％、７−オクテン−１−オール６．０％、１−オクタノール２．０％、酢酸エチル１．７％であった（７，８−エポキシ−１−オクタノールの収率は７６．０％）。
残存する７−オクテン−１−オール、１−オクタノール、酢酸エチルは７，８−エポキシ−１−オクタノールに対して低い沸点を持つことから、１５５℃／２０００Ｐａで、低沸点成分の除去を行い、残留液２３９．０ｇを得た。
得られた残留液をＧＣにて組成分析すると７，８−エポキシ−１−オクタノール９８．１％、２，８−ジヒドロキシオクタン−１−オール酢酸エステル１．９％であり、７−オクテン−１−オール、１−オクタノール、酢酸エチルは検出されなかった（７，８−エポキシ−１−オクタノールの収率は７１．６％）。
２，８−ジヒドロキシオクタン−１−オール酢酸エステルは、７，８−エポキシ−１−オクタノールに対して高い沸点を持つことから、１７０℃／２０００Ｐａで、高沸点化合物の除去を行い、溜出液２２７．５ｇを得た。
得られた溜出液をＧＣにて組成分析すると７，８−エポキシ−１−オクタノール９８．５％、２，８−ジヒドロキシオクタン−１−オール酢酸エステル１．５％であった（７，８−エポキシ−１−オクタノールのトータル収率は６８．５％）。
図３に得られた留出液の1Ｈ−ＮＭＲスペクトルを示す（横軸はδ値、縦軸はシグナル強度を示す）。1Ｈ−ＮＭＲ測定は溶媒としてＣＤＣｌ３を用いて、内部標準ＴＭＳで行った。原料の７−オクテン−１−オールに見られたδ４．８およびδ５．６付近の末端二重結合に由来するピークが消失しており、δ２．３〜δ３．０付近にエポキシ基に由来するプロトンのピークが確認され、上記残留液は、大部分が目的生成物である７，８−エポキシ−１−オクタノールであることが確認された。
(Example 2)
A reactor was charged with 300 g of 7-octen-1-ol containing 3% of 1-octanol and 300 g of ethyl acetate, and nitrogen was blown into the gas phase part and the temperature in the reaction system was controlled to 60 ° C. Then, 633 g of an ethyl acetate solution (water content 0.41% by mass) containing 30% by mass of peracetic acid was added dropwise over about 4 hours. After the peracetic acid solution was dropped, the reaction was terminated by aging with stirring at 60 ° C. for 3 hours.
Next, 603 g of 10% aqueous sodium hydroxide solution was added to the reaction crude liquid with stirring at 30 ° C. or lower, stirring was stopped, and two layers were separated, and the lower aqueous layer was separated and removed. After repeating this operation three times, 400 g of deionized water was added to the upper organic layer, and the remaining neutralized salt was washed away.
The low boiling point compound was removed from the washed crude liquid at 70 ° C./2666 Pa to obtain 278.5 g of a residual liquid.
When the composition of the obtained residual liquid was analyzed by GC, 8,9.4-epoxy-1-octanol 89.4%, 2,8-dihydroxyoctane-1-ol acetate 0.9%, 7-octen-1-ol They were 6.0%, 1-octanol 2.0%, and ethyl acetate 1.7% (7,8-epoxy-1-octanol yield was 76.0%).
Since the remaining 7-octen-1-ol, 1-octanol and ethyl acetate have a low boiling point relative to 7,8-epoxy-1-octanol, the low boiling point component is removed at 155 ° C./2000 Pa, 239.0 g of residual liquid was obtained.
When the composition of the obtained residual liquid was analyzed by GC, it was 98.1% 7,8-epoxy-1-octanol, 1.9% 2,8-dihydroxyoctane-1-ol acetate, and 7-octene-1 -Ol, 1-octanol and ethyl acetate were not detected (the yield of 7,8-epoxy-1-octanol was 71.6%).
Since 2,8-dihydroxyoctane-1-ol acetate has a higher boiling point than 7,8-epoxy-1-octanol, high boiling point compounds are removed at 170 ° C./2000 Pa, and the distillate is distilled off. 227.5 g was obtained.
When the composition of the obtained distillate was analyzed by GC, it was found to be 98.5% 7,8-epoxy-1-octanol and 1.5% 2,8-dihydroxyoctane-1-ol acetate (7,8 -The total yield of epoxy-1-octanol is 68.5%).
FIG. 3 shows the 1 H-NMR spectrum of the obtained distillate (the horizontal axis indicates the δ value, and the vertical axis indicates the signal intensity). 1 H-NMR measurement was performed with internal standard TMS using CDCl 3 as a solvent. The peaks derived from the terminal double bonds in the vicinity of δ4.8 and δ5.6 observed in the starting material 7-octen-1-ol disappeared, and the peaks originated from the epoxy group in the vicinity of δ2.3 to δ3.0. A proton peak was confirmed, and it was confirmed that most of the residual liquid was 7,8-epoxy-1-octanol, which was the target product.
（比較例１）
１−オクタノールを１２％含有する７−オクテン−１−オール３００ｇ及び酢酸エチル３００ｇを仕込み、窒素を気相部に吹き込みながら、かつ、反応系内の温度を６０℃になるようにコントロールしながら約４時間かけて３０質量％過酸化水素水２５７ｇを滴下した。過酸化水素水滴下終了後、６０℃で１２時間熟成し反応を終了した。
反応粗液の1Ｈ−ＮＭＲの測定では、δ４．８およびδ５．６付近の末端二重結合に由来するピークの消失は確認できず、またδ２．３〜δ３．０付近にエポキシ基に由来するプロトンのピークの生成も確認することができなかった。７，８−エポキシ−１−オクタノールを合成できなかった。
(Comparative Example 1)
About 300 g of 7-octen-1-ol containing 12% of 1-octanol and 300 g of ethyl acetate were charged, nitrogen was blown into the gas phase part, and the temperature in the reaction system was controlled to 60 ° C. Over 4 hours, 257 g of 30% by mass hydrogen peroxide was added dropwise. After the dropwise addition of hydrogen peroxide, the reaction was terminated by aging at 60 ° C. for 12 hours.
In the 1 H-NMR measurement of the reaction crude liquid, disappearance of peaks derived from terminal double bonds in the vicinity of δ4.8 and δ5.6 could not be confirmed, and it was derived from an epoxy group in the vicinity of δ2.3 to δ3.0. The generation of proton peaks was not confirmed. 7,8-epoxy-1-octanol could not be synthesized.
本発明の製造方法で得られる７，８−エポキシ−１−オクタノールは、塩素分のような微量の不純物が少なく、各種化学品（たとえば、医薬・農薬の原料、樹脂原料等）の原料として利用可能である。 The 7,8-epoxy-1-octanol obtained by the production method of the present invention has a small amount of impurities such as chlorine, and is used as a raw material for various chemical products (for example, raw materials for pharmaceuticals and agricultural chemicals, resin raw materials, etc.). Is possible.
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