JPH08231525A - Production of gamma-alkyl-gamma-lactone - Google Patents
Production of gamma-alkyl-gamma-lactoneInfo
- Publication number
- JPH08231525A JPH08231525A JP7037873A JP3787395A JPH08231525A JP H08231525 A JPH08231525 A JP H08231525A JP 7037873 A JP7037873 A JP 7037873A JP 3787395 A JP3787395 A JP 3787395A JP H08231525 A JPH08231525 A JP H08231525A
- Authority
- JP
- Japan
- Prior art keywords
- lactone
- reaction
- acrylic acid
- alkyl
- alcohol
- 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
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
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、香料として、あるいは
香料、医薬品、農薬などの出発原料として有用なγ-ア
ルキル-γ-ラクトンの新規製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel method for producing γ-alkyl-γ-lactone which is useful as a perfume or as a starting material for perfumes, pharmaceuticals, agricultural chemicals and the like.
【０００２】[0002]
【従来の技術】γ-アルキル-γ-ラクトンは、一般に桃
様等の果実様香気を有し香料として用いられるほか、香
料、医薬品、農薬等の合成原料としても有用である。BACKGROUND OF THE INVENTION γ-Alkyl-γ-lactone generally has a fruity aroma such as peach and is used as a flavor, and is also useful as a synthetic raw material for flavors, pharmaceuticals, agricultural chemicals and the like.
【０００３】従来、γ-アルキル-γ-ラクトンの製造方
法としては、γ-ケト酸を還元する方法〔Zhur Obschche
i Khim., 31, 984(1961)〕、γ−アルキル不飽和カルボ
ン酸を硫酸と加熱する方法（特公昭38-4060号公報）
等、種々の方法が知られている。しかし、これらの方法
には、原料の入手が困難である、原料が高価である等の
問題があった。Conventionally, as a method for producing γ-alkyl-γ-lactone, a method of reducing γ-keto acid [Zhur Obschche
i Khim., 31, 984 (1961)], a method of heating a γ-alkyl unsaturated carboxylic acid with sulfuric acid (Japanese Patent Publication No. 38-4060).
Various methods are known. However, these methods have problems that the raw materials are difficult to obtain and the raw materials are expensive.
【０００４】これに対し、入手が容易な原料を用いる方
法として、アルコールとアクリル酸又はアクリル酸メチ
ルとのラジカル付加反応による方法が提案されている
〔Izvest. Akad. Nauk. SSSR, Otd. Khim. Nauk., 187x
(1962)〕。しかし、この方法のような単なる加熱反応で
は、γ-アルキル-γ-ラクトンの収率が20〜30％程度と
極めて悪いという問題がある。この収率の低さは、原料
アルコールをアクリル酸又はアクリル酸メチルに対して
10倍モル以上という大過剰用いることによりある程度改
善することができるが、この場合には原料アルコールの
回収、再生等が煩雑で生産性が悪く、経済的に不利とな
る。On the other hand, as a method using an easily available raw material, a method by radical addition reaction of alcohol with acrylic acid or methyl acrylate has been proposed [Izvest. Akad. Nauk. SSSR, Otd. Khim. Nauk., 187x
(1962)]. However, the mere heat reaction as in this method has a problem that the yield of γ-alkyl-γ-lactone is extremely poor at about 20 to 30%. This low yield means that the raw material alcohol is based on acrylic acid or methyl acrylate.
Although it can be improved to some extent by using a large excess of 10 times or more, in this case, the recovery and regeneration of the raw material alcohol is complicated and the productivity is poor, which is economically disadvantageous.
【０００５】そこで、かかる問題点を伴わずに収率及び
生産性を向上させる方法として、アクリル酸エステルを
原料とし、触媒としてスルホン酸類を添加する（特公昭
53-36466号公報）、リン酸塩及び／又は硫酸塩を添加す
る（特公昭52-42794号公報）、アクリル酸又はアクリル
酸エステルを原料とし、触媒としてハロゲン化亜鉛を添
加する（特開平4-54177号公報）等の方法が知られてい
る。Therefore, as a method of improving the yield and productivity without such problems, acrylic acid ester is used as a raw material and sulfonic acids are added as a catalyst (Japanese Patent Publication No.
No. 53-36466), a phosphate and / or a sulfate is added (Japanese Patent Publication No. 52-42794), acrylic acid or an acrylic ester is used as a raw material, and zinc halide is added as a catalyst (Japanese Patent Laid-Open No. Hei 4). -54177 gazette) etc. are known.
【０００６】[0006]
【発明が解決しようとする課題】しかし、これら触媒を
用いる方法も、その収率は未だ十分満足できるものでは
ないと共に、反応容器の材質に制限を受けたり、添加剤
を除去する工程や廃アルコールの処理が必要であるなど
操作が煩雑となって経済的に不利であったり、また添加
剤を用いる方法で合成したラクトンには容易に除去でき
ない脂っぽい異臭が残って香料用途には不向きであると
いう問題があった。However, in the methods using these catalysts, the yield is not yet sufficiently satisfactory, and the material of the reaction vessel is limited, the step of removing the additive and the waste alcohol It is economically disadvantageous because the procedure is complicated and the operation is complicated, and the lactone synthesized by the method using an additive has a greasy off-odor that cannot be easily removed and is not suitable for perfume use. There was a problem.
【０００７】従って、触媒を使用することなく、より簡
便かつ高収率で、高品質のγ-アルキル-γ-ラクトンを
製造し得る方法の開発が望まれていた。Therefore, it has been desired to develop a method capable of producing high-quality γ-alkyl-γ-lactone in a simpler and higher yield without using a catalyst.
【０００８】[0008]
【課題を解決するための手段】かかる実情において、本
発明者らは上記課題を解決すべく鋭意研究を重ねた結
果、アクリル酸とアルコールとの反応を、加圧条件下、
低沸点成分を反応系外に留去しながら行うことにより収
率が向上することを見いだし、本発明を完成した。Under these circumstances, the inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, the reaction between acrylic acid and alcohol was
It was found that the yield can be improved by distilling the low boiling point component out of the reaction system, and the present invention was completed.
【０００９】すなわち本発明は、アクリル酸と、総炭素
数５〜10の第一級アルコールもしくは第二級アルコール
又はそれらの混合物とを、ジ第三級ブチルパーオキシド
の存在下、160〜190℃、加圧条件下で低沸点成分を留去
しながら反応させることを特徴とするγ-アルキル-γ-
ラクトンの製造方法を提供するものである。That is, according to the present invention, acrylic acid and a primary or secondary alcohol having a total carbon number of 5 to 10 or a mixture thereof are added in the presence of ditertiary butyl peroxide at 160 to 190 ° C. Γ-Alkyl-γ-, characterized in that the reaction is carried out while distilling off the low boiling point components under pressure
A method for producing a lactone is provided.
【００１０】本発明方法に用いられる出発原料であるア
クリル酸は含水品及び無水品のどちらでもよい。しか
し、本発明方法では、アクリル酸の代わりにアクリル酸
メチルを用いても低い収率しか得られない。Acrylic acid, which is the starting material used in the method of the present invention, may be either a hydrous product or an anhydrous product. However, in the method of the present invention, a low yield can be obtained even if methyl acrylate is used instead of acrylic acid.
【００１１】本発明方法において出発原料として用いら
れる総炭素数５〜10の第一級アルコールとしては、例え
ば1-ペンタノール、1-ヘキサノール、1-ヘプタノール、
1-オクタノール、1-ノナノール、1-デカノール、3-メチ
ル-1-ブタノール、4-メチル-1-ペンタノール、5-メチル
-1-ヘキサノール、6-メチル-1-ヘプタノール、7-メチル
-1-オクタノール、8-メチル-1-ノナノール等が挙げられ
る。第一級アルコールを用いた場合、得られるラクトン
はγ-モノアルキル-γ-ラクトンとなる。また、第二級
アルコールとしては、2-ペンタノール、2-ヘキサノー
ル、2-ヘプタノール、2-オクタノール、2-ノナノール、
2-デカノール等が挙げられる。第二級アルコールを用い
た場合、得られるラクトンはγ-ジアルキル-γ-ラクト
ンとなる。これらのうち、炭素数６〜10の第１級アルコ
ール、特に炭素数６〜10の直鎖第１級アルコールが好ま
しい。アルコールの使用量は、アクリル酸１モルに対し
て３〜８モル、特に４〜７モルの範囲が好ましい。Examples of the primary alcohol having a total carbon number of 5 to 10 used as a starting material in the method of the present invention include 1-pentanol, 1-hexanol, 1-heptanol,
1-octanol, 1-nonanol, 1-decanol, 3-methyl-1-butanol, 4-methyl-1-pentanol, 5-methyl
-1-hexanol, 6-methyl-1-heptanol, 7-methyl
-1-octanol, 8-methyl-1-nonanol and the like can be mentioned. If a primary alcohol is used, the resulting lactone will be γ-monoalkyl-γ-lactone. Further, as the secondary alcohol, 2-pentanol, 2-hexanol, 2-heptanol, 2-octanol, 2-nonanol,
2-decanol and the like can be mentioned. When a secondary alcohol is used, the lactone obtained is γ-dialkyl-γ-lactone. Of these, primary alcohols having 6 to 10 carbon atoms, particularly linear primary alcohols having 6 to 10 carbon atoms are preferable. The amount of alcohol used is preferably 3 to 8 mol, and more preferably 4 to 7 mol per 1 mol of acrylic acid.
【００１２】また、ジ第三級ブチルパーオキシドの使用
量は、アクリル酸１モルに対して0.01〜0.5モル、特に
0.04〜0.2モルが好ましい。The amount of ditertiary butyl peroxide used is 0.01 to 0.5 mol, especially 1 mol of acrylic acid.
0.04 to 0.2 mol is preferred.
【００１３】本反応は160〜190℃の反応温度で行われ、
特に165〜185℃の温度で行うのが好ましい。160℃未満
では触媒の分解が遅く反応速度が上がらず、190℃を超
える温度では触媒の分解が速過ぎる。また、本反応は前
記原料アルコールにアクリル酸と第三級ブチルパーオキ
シドとを２〜10時間で滴下して行うのが効果的である。This reaction is carried out at a reaction temperature of 160 to 190 ° C.,
It is particularly preferable to carry out at a temperature of 165-185 ° C. If the temperature is lower than 160 ° C, the decomposition of the catalyst is slow and the reaction rate does not increase, and if the temperature exceeds 190 ° C, the decomposition of the catalyst is too fast. It is effective to carry out this reaction by dropping acrylic acid and tert-butyl peroxide into the above-mentioned raw material alcohol for 2 to 10 hours.
【００１４】本発明方法は、低沸点成分を反応系外に留
去しながら行われるが、ここでいう低沸点成分とは、ラ
ジカル付加反応が進行するに従い生成する第３級ブタノ
ール、水等の混合物をいう。これらが反応系内に蓄積す
ると反応率が低下してしまう。低沸点成分の留出量は、
反応系内の圧力と関連し、圧力が決まれば留出量もほぼ
決定するが、理論量の20％以上、特に30〜80％が好まし
い。なお、留去される低沸点成分中には、反応率を低下
させない範囲で原料アルコールが混入してもよい。The method of the present invention is carried out while distilling the low-boiling component out of the reaction system. The low-boiling component as used herein means a tertiary butanol, water or the like produced as the radical addition reaction proceeds. Refers to a mixture. If these accumulate in the reaction system, the reaction rate will decrease. The distillation amount of low boiling point components is
Although the amount of distillate is almost determined when the pressure is determined in relation to the pressure in the reaction system, it is preferably 20% or more of the theoretical amount, particularly 30 to 80%. The raw material alcohol may be mixed in the low-boiling-point component to be distilled off, as long as the reaction rate is not lowered.
【００１５】反応系内の圧力は、常圧以下では系内の温
度が上がらなかったり原料アルコールの留出量が多くな
りすぎ、収率の低下を招く。従って、本反応は加圧下行
われ、加圧度は特に限定されないが、圧力があまり高い
と反応容器が高価になり不経済なため、絶対圧力で10kg
/cm2以下の加圧状態、特に1.3〜５kg/cm2の範囲に調整
するのが好ましい。系内の圧力調整は、例えば一定圧力
になると作動する圧力調整弁及び留出物の受器を有する
オートクレーブを用いた密閉系で反応させる等の方法に
よって行うことができる。なお、系内の圧力調整及び低
沸点成分の留出のため窒素、アルゴン等の不活性ガスを
用いてもよい。If the pressure in the reaction system is below atmospheric pressure, the temperature in the system will not rise and the amount of the raw material alcohol distilled will be too large, resulting in a decrease in yield. Therefore, this reaction is carried out under pressure, and the degree of pressurization is not particularly limited, but if the pressure is too high, the reaction vessel will be expensive and uneconomical.
/ cm 2 or less under pressure, in particular to adjust the range of 1.3～5Kg / cm 2 preferably. The pressure in the system can be adjusted by, for example, a reaction in a closed system using an autoclave having a pressure adjusting valve that operates at a constant pressure and a distillate receiver. An inert gas such as nitrogen or argon may be used for adjusting the pressure in the system and distilling off the low boiling point component.
【００１６】また、反応混合物からγ-アルキル-γ-ラ
クトンを精製する方法としては、従来公知の方法、例え
ば蒸留法、溶媒抽出法、再結晶法、カラムクロマト法等
から適宜選択することができる。The method for purifying γ-alkyl-γ-lactone from the reaction mixture can be appropriately selected from conventionally known methods such as distillation, solvent extraction, recrystallization and column chromatography. .
【００１７】本発明方法により好適に製造し得るγ-ア
ルキル-γ-ラクトンとしては、γ-ペンチル-γ-ブチロ
ラクトン、γ-ヘキシル-γ-ブチロラクトン、γ-ヘプチ
ル-γ-ブチロラクトン、γ-オクチル-γ-ブチロラクト
ン、γ-ノニル-γ-ブチロラクトン、γ-(3-メチルブチ
ル)-γ-ブチロラクトン、γ-(4-メチルペンチル)-γ-ブ
チロラクトン、γ-(5-メチルヘキシル)-γ-ブチロラク
トン、γ-(6-メチルヘプチル)-γ-ブチロラクトン、γ-
(7-メチルオクチル)-γ-ブチロラクトン、γ-メチル-γ
-ヘキシル-γ-ブチロラクトン等が挙げられる。Γ-Alkyl-γ-lactone which can be preferably produced by the method of the present invention includes γ-pentyl-γ-butyrolactone, γ-hexyl-γ-butyrolactone, γ-heptyl-γ-butyrolactone and γ-octyl- γ-butyrolactone, γ-nonyl-γ-butyrolactone, γ- (3-methylbutyl) -γ-butyrolactone, γ- (4-methylpentyl) -γ-butyrolactone, γ- (5-methylhexyl) -γ-butyrolactone, γ- (6-methylheptyl) -γ-butyrolactone, γ-
(7-Methyloctyl) -γ-butyrolactone, γ-methyl-γ
-Hexyl-γ-butyrolactone and the like.
【００１８】[0018]
【実施例】以下、実施例を挙げて本発明を更に詳細に説
明するが、本発明はこれらに限定されるものではない。EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.
【００１９】実施例１ １リットルのオートクレーブに、1-オクタノール400g
（純度98％，3.0mol）を入れ、175℃に加熱保持し攪拌
しながら、この中に含水アクリル酸49g（純度80％，0.5
4mol）とジ第三級ブチルパーオキシド7.9g（0.05mol）
を70g（0.5mol）の1-オクタノールに溶かした溶液を６
時間かけて圧入した。この間、低沸点成分を留出させ
（６g）、圧力２kg/cm2を維持した。滴下終了後、同じ
圧力及び温度で更に１時間反応を行った。反応終了後、
反応液から未反応の1-オクタノールを留去し、次いで減
圧蒸留してγ-ヘプチル-γ-ブチロラクトンを79g（0.43
mol，収率80％）得た。得られたラクトンは、脂っぽさ
はなく、クリーンな桃様の香りを有していた。Example 1 400 g of 1-octanol was placed in a 1 liter autoclave.
(Purity 98%, 3.0mol) was added, heated and kept at 175 ℃ and stirred, while hydrous acrylic acid 49g (Purity 80%, 0.5
4 mol) and di-tertiary butyl peroxide 7.9 g (0.05 mol)
6 g of a solution prepared by dissolving 70 g (0.5 mol) of 1-octanol
Pressed in over time. During this period, low boiling components were distilled off (6 g) and the pressure was maintained at 2 kg / cm 2 . After the dropping was completed, the reaction was carried out at the same pressure and temperature for 1 hour. After the reaction,
Unreacted 1-octanol was distilled off from the reaction solution, followed by vacuum distillation to obtain γ-heptyl-γ-butyrolactone 79 g (0.43
mol, yield 80%) was obtained. The resulting lactone was not greasy and had a clean peach-like scent.
【００２０】実施例２ 実施例１において1-オクタノールの代わりに1-デカノー
ルを用いる以外は同様に反応を行い、γ-ノニル-γ-ブ
チロラクトンを得た（収率79％）。得られたラクトン
は、脂っぽさはなく、クリーンな桃様の香りを有してい
た。Example 2 γ-Nonyl-γ-butyrolactone was obtained in the same manner as in Example 1 except that 1-decanol was used instead of 1-octanol to obtain γ-nonyl-γ-butyrolactone (yield 79%). The resulting lactone was not greasy and had a clean peach-like scent.
【００２１】実施例３ １リットルのオートクレーブに、1-ヘキサノール282g
（純度99％，2.7mol）を入れ、170℃に加熱保持し攪拌
しながら、この中に含水アクリル酸54g（純度80％，0.6
mol）とジ第三級ブチルパーオキシド8.8g（0.06mol）を
116g（1.1mol）の1-ヘキサノールに溶かした溶液を６時
間かけて圧入した。この間、低沸点成分を留出させ（12
g）、圧力４kg/cm2を維持した。滴下終了後、同じ圧力
及び温度で更に１時間反応を行った。反応終了後、反応
液から未反応の1-ヘキサノールを留去し、次いで減圧蒸
留してγ-ペンチル-γ-ブチロラクトンを71g（0.45mo
l，収率76％）得た。得られたラクトンは、脂っぽさは
なく、クリーンなココナッツ様の香りを有していた。Example 3 In a 1 liter autoclave, 282 g of 1-hexanol
(Purity 99%, 2.7mol) was added, heated and kept at 170 ℃ and stirred while hydrous acrylic acid 54g (Purity 80%, 0.6mol).
mol) and di-tert-butyl peroxide 8.8g (0.06mol)
A solution of 116 g (1.1 mol) in 1-hexanol was pressed in for 6 hours. During this period, low boiling point components are distilled off (12
g), a pressure of 4 kg / cm 2 was maintained. After the dropping was completed, the reaction was carried out at the same pressure and temperature for 1 hour. After completion of the reaction, unreacted 1-hexanol was distilled off from the reaction solution, and then distilled under reduced pressure to obtain 71 g (0.45 mol) of γ-pentyl-γ-butyrolactone.
l, yield 76%). The resulting lactone was not greasy and had a clean coconut-like scent.
【００２２】実施例４ 実施例２において1-ヘキサノールの代わりに2-オクタノ
ールを用いる以外は同様に反応を行い、γ-メチル-γ-
ヘキシル-γ-ブチロラクトンを得た（収率73％）。得ら
れたラクトンは、脂っぽさはなく、クリーンな花様の香
りを有していた。Example 4 The same reaction was carried out as in Example 2 except that 2-octanol was used instead of 1-hexanol, and γ-methyl-γ-
Hexyl-γ-butyrolactone was obtained (yield 73%). The resulting lactone was not greasy and had a clean flower-like scent.
【００２３】比較例１ 実施例１において、オートクレーブ中密閉系で低沸点成
分の留去を行わずに反応を行ったところ、得られたγ-
ヘプチル-γ-ブチロラクトンの収率は49％であった。Comparative Example 1 In Example 1, the reaction was carried out in an autoclave in a closed system without distilling off low-boiling components.
The yield of heptyl-γ-butyrolactone was 49%.
【００２４】比較例２ 実施例１において、アクリル酸の代わりにアクリル酸メ
チルを用い、オートクレーブ中密閉系でメタノール等の
低沸点成分を計２ｇ留出させつつ反応を行ったところ、
得られたγ-ヘプチル-γ-ブチロラクトンの収率は51％
であった。COMPARATIVE EXAMPLE 2 Methyl acrylate was used in place of acrylic acid in Example 1, and the reaction was carried out in a closed system in an autoclave while distilling out a total of 2 g of a low boiling point component such as methanol,
The yield of the obtained γ-heptyl-γ-butyrolactone is 51%.
Met.
【００２５】比較例３ 実施例１において、常圧下に低沸点成分を計30ｇ留出さ
せつつ反応を行ったところ、得られたγ-ヘプチル-γ-
ブチロラクトンの収率は60％であった。また、得られた
ラクトンは草様の異臭があり、香料用途には適しないも
のであった。Comparative Example 3 In Example 1, the reaction was carried out while distilling out a total of 30 g of low-boiling components under normal pressure, and the obtained γ-heptyl-γ-
The yield of butyrolactone was 60%. In addition, the obtained lactone had a grassy offensive odor and was not suitable for perfume use.
【００２６】比較例４〜６ 実施例１において、アクリル酸の代わりにアクリル酸メ
チルを用い、オートクレーブ中密閉系で表１に示す添加
剤を加え、低沸点成分の留去を行わずに反応を行い表１
に示す収率でγ-ヘプチル-γ-ブチロラクトンを得た。
得られたラクトンは、脂っぽい匂いがあり、香料用途に
は適しなかった。Comparative Examples 4 to 6 In Example 1, methyl acrylate was used instead of acrylic acid, the additives shown in Table 1 were added in a closed system in an autoclave, and the reaction was carried out without distilling off low-boiling components. Table 1
Γ-heptyl-γ-butyrolactone was obtained in the yield shown in.
The obtained lactone had a greasy odor and was not suitable for perfume use.
【００２７】[0027]
【表１】 [Table 1]
【００２８】[0028]
【発明の効果】以上のように、本発明によれば、簡便か
つ高収率で、高品質のγ-アルキル-γ-ラクトンを製造
することができる。INDUSTRIAL APPLICABILITY As described above, according to the present invention, high-quality γ-alkyl-γ-lactone can be easily produced in high yield.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 羽木 久憲 和歌山県那賀郡岩出町大字山980−２ 水 鉄アーバンコンフォート岩出707号 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hisanori Haki 980-2 Ooyama, Iwade-cho, Naga-gun, Wakayama Mizutetsu Urban Comfort Iwade 707
Claims (2)
アルコールもしくは第二級アルコール又はそれらの混合
物とを、ジ第三級ブチルパーオキシドの存在下、160〜1
90℃、加圧条件下で低沸点成分を留去しながら反応させ
ることを特徴とするγ-アルキル-γ-ラクトンの製造方
法。1. Acrylic acid and a primary alcohol or secondary alcohol having a total carbon number of 5 to 10 or a mixture thereof are added in the presence of ditertiary butyl peroxide in an amount of 160 to 1
A method for producing a γ-alkyl-γ-lactone, which comprises reacting at 90 ° C. under pressure while distilling off low-boiling components.
う請求項１記載のγ-アルキル-γ-ラクトンの製造方
法。 2. The method for producing a γ-alkyl-γ-lactone according to claim 1, wherein the reaction is performed under an absolute pressure of 10 kg / cm 2 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07037873A JP3126891B2 (en) | 1995-02-27 | 1995-02-27 | Method for producing γ-alkyl-γ-lactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07037873A JP3126891B2 (en) | 1995-02-27 | 1995-02-27 | Method for producing γ-alkyl-γ-lactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08231525A true JPH08231525A (en) | 1996-09-10 |
| JP3126891B2 JP3126891B2 (en) | 2001-01-22 |
Family
ID=12509660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07037873A Expired - Fee Related JP3126891B2 (en) | 1995-02-27 | 1995-02-27 | Method for producing γ-alkyl-γ-lactone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3126891B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617522A (en) * | 2012-01-11 | 2012-08-01 | 厦门大学 | Method for synthesis of gamma-nonyl lactone |
| CN103030614A (en) * | 2011-09-29 | 2013-04-10 | 南昌洋浦天然香料香精有限公司 | Extracting method of synthetic peach aldehyde |
| CN108997269A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of method of reactive distillation synthesis arbricolin synthetic perfume |
-
1995
- 1995-02-27 JP JP07037873A patent/JP3126891B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103030614A (en) * | 2011-09-29 | 2013-04-10 | 南昌洋浦天然香料香精有限公司 | Extracting method of synthetic peach aldehyde |
| CN102617522A (en) * | 2012-01-11 | 2012-08-01 | 厦门大学 | Method for synthesis of gamma-nonyl lactone |
| CN108997269A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of method of reactive distillation synthesis arbricolin synthetic perfume |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3126891B2 (en) | 2001-01-22 |
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