JPS62141097A - Purification of perfume base material - Google Patents
Purification of perfume base materialInfo
- Publication number
- JPS62141097A JPS62141097A JP28047285A JP28047285A JPS62141097A JP S62141097 A JPS62141097 A JP S62141097A JP 28047285 A JP28047285 A JP 28047285A JP 28047285 A JP28047285 A JP 28047285A JP S62141097 A JPS62141097 A JP S62141097A
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- Prior art keywords
- product
- odor
- water vapor
- comparative example
- fragrance material
- Prior art date
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- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Fats And Perfumes (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は香料組成物に有用な香料素材の精製法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for purifying perfume materials useful in perfume compositions.
従来、香料素材の精製法としては、蒸留法や晶析法(結
晶性香料素材の場合)などが一般に用いられているが、
これらの方法により精製した香料素材には異臭成分が残
存しており、香料用途に適さない場合が多かった。Traditionally, methods such as distillation and crystallization (for crystalline fragrance materials) have been commonly used to purify fragrance materials.
Perfume materials purified by these methods often contain residual off-flavor components and are not suitable for use as perfumes.
例えば、熱的に不安定な官能基例えばアルデヒド、ケト
ン、アルコール、エーテル、エステル、ラクトン、オレ
フィンなどを主成分あるいは不純物に有する香料素材を
従来の蒸留法により精製すれば、これらの成分の熱的分
解により好ましくない異臭が発生し、そのまま香料素材
として用いることはできないという欠点があった。For example, if a fragrance material containing thermally unstable functional groups such as aldehydes, ketones, alcohols, ethers, esters, lactones, olefins, etc. as main components or impurities is purified by conventional distillation, the thermal It has the disadvantage that it generates an unpleasant odor due to decomposition and cannot be used as a fragrance material as it is.
そこで本発明者らは従来の精製を施した後に微量残存す
る異臭成分を効果的に除去する方法について鋭意研究を
重ねた結果、これら微量残存する異臭成分は従来の精製
を行なう際に不純物あるいは主成分が化学変化して生成
される場合が多く、しかもその異臭成分は主成分と同等
程度もしくはそれ以下の沸点である場合が多いことを見
出し、そこで、微量生成する異臭成分を水蒸気を吹き込
むことにより除去することを試みたところ、異臭成分除
去効果が大きく認められ本発明を完成するに至った。Therefore, the present inventors have conducted extensive research into methods for effectively removing off-flavor components that remain in trace amounts after conventional purification. We discovered that the off-flavor components are often produced through chemical changes, and that the boiling point of the off-flavor components is often equal to or lower than that of the main component. When an attempt was made to remove the off-flavor components, the effect of removing the off-flavor components was found to be significant, leading to the completion of the present invention.
即ち、本発明は、異臭成分を含有する香料素材に水蒸気
を吹き込むことを特徴とする香料素材の精製法を提供す
るものであり、更に好ましい態様として、蒸留法あるい
は晶析法による精製工程を経た香料素材であって微量異
臭成分を含着する香料素材に水蒸気を吹き込むことを特
徴とする香料素材の精製法を提供するものである。That is, the present invention provides a method for purifying a fragrance material, which is characterized by blowing steam into a fragrance material containing an off-flavor component, and as a more preferred embodiment, a method for purifying a fragrance material that includes a distillation method or a crystallization method. To provide a method for purifying a fragrance material, which is characterized by blowing water vapor into the fragrance material impregnated with a trace amount of off-flavor component.
本発明でいう香料素材とは、香料組成物に用いられる化
合物であれば特に限定されないが、例えば、ステファン
アークテンダーに記載の化合物等が挙げられる。The fragrance material as used in the present invention is not particularly limited as long as it is a compound used in a fragrance composition, and examples thereof include compounds described in Stefan Arctender.
本発明で用いられる異臭成分を含有する香料素材とは、
好ましくない異臭成分を含有していることにより、その
ままでは香料用途に適さないものであり、例えば、蒸留
法及び晶析法等により精製されたものが挙げられる。The fragrance material containing an off-flavor component used in the present invention is:
Because it contains undesirable off-flavor components, it is unsuitable for use as a perfume as it is, and examples include those purified by distillation, crystallization, etc.
本発明においては、異臭成分を含有する香料素材に水蒸
気を吹き込むことにより異臭成分を除去する。この際に
用いられる容器としては、例えば減圧ラインを持ち、水
蒸気導入管を持ったものがある。水蒸気を吹き込む方法
は特に限定されないが、容器の底部から吹き込む方法が
、水蒸気が均一に系内に入るのでより好ましい。In the present invention, off-flavor components are removed by blowing steam into a perfume material containing off-odor components. Examples of containers used in this case include those equipped with a pressure reduction line and a steam introduction pipe. Although there are no particular limitations on the method of blowing the steam, a method of blowing from the bottom of the container is more preferable because the steam enters the system uniformly.
本発明の方法を実施するための装置の一例を第1図に示
す。An example of an apparatus for carrying out the method of the invention is shown in FIG.
水蒸気を吹き込む条件、即ち水蒸気の温度、系内の圧力
、温度などは、適宜選択設定される。The conditions for blowing the steam, ie, the temperature of the steam, the pressure in the system, the temperature, etc., are selected and set as appropriate.
香料用途として有効な主成分があまり溜出しない条件が
好ましい。沸点に到達しない温度、圧力の範囲で設定す
るのが好ましい。通常は、水蒸気の温度は20〜80℃
、系内の圧力、温度はそれぞれ40〜100 mmHg
、 30〜200℃の範囲で選ぶのが好ましい。Preferable conditions are such that the main components effective for perfume use are not distilled out to a large extent. It is preferable to set the temperature and pressure within a range that does not reach the boiling point. Normally, the temperature of water vapor is 20-80℃
, the pressure and temperature in the system are 40 to 100 mmHg, respectively.
, is preferably selected within the range of 30 to 200°C.
水蒸気の吹き込み量は異臭成分を含有する香料素材によ
り異なるが、一般には、異臭成分を含有する香料素材に
対して1重量%〜100重世%の範囲で選ぶのが好まし
い。水蒸気の吹き込み量が少なすぎる場合には異臭成分
を除去しきれず、また逆に多すぎる場合には経済的に好
ましくない。The amount of water vapor blown varies depending on the fragrance material containing the off-flavor component, but is generally preferably selected in the range of 1% to 100% by weight based on the fragrance material containing the off-odor component. If the amount of water vapor blown is too small, the off-flavor components cannot be removed completely, and on the other hand, if it is too large, it is economically unfavorable.
水蒸気を吹き込んで異臭成分を除去する際には、目的と
する香料の主成分もわずかに溜出するが、異臭成分を含
有する香料素材全量に対して0.1〜50重量%程度の
範囲で溜出させると異臭成分を好ましく除去することが
できる。より好ましくは0.5〜10重量%の範囲の量
である。When steam is blown to remove off-flavor components, a small amount of the main components of the desired fragrance are also distilled out, but within a range of about 0.1 to 50% by weight based on the total amount of the fragrance material containing off-odor components. By distilling, off-flavor components can be preferably removed. More preferably, the amount ranges from 0.5 to 10% by weight.
主成分の溜出量は水蒸気の吹き込み量、温度、真空度な
どをコントロールすることにより所望の値に設定するこ
とができる。The amount of the main component distilled out can be set to a desired value by controlling the amount of water vapor blown, the temperature, the degree of vacuum, etc.
水蒸気を吹き込むことが異臭成分除去にどの様に有効で
あるかは明らかではないが、水蒸気を吹き込むことによ
り、異臭成分が水溶性である場合には水蒸気とともに容
易に除去されるであろうし、また、水溶性でない場合で
も、水蒸気による異臭成分の飛沫同伴効果により効果的
に除去されるものと考えられる。It is not clear how effective blowing water vapor is in removing off-odor components, but if the off-odor components are water-soluble, they will be easily removed along with the water vapor. Even if the odor is not water-soluble, it is thought that the off-flavor components are effectively removed due to the entrainment effect of water vapor.
以下に、実施例を示して本発明を具体的に説明するが、
本発明はこれらの実施例のみに限定されるものではない
。The present invention will be specifically explained below with reference to Examples.
The present invention is not limited only to these examples.
尚、異臭成分を含有する香料素材の製造の例を参考例に
示し、このものを従来の精製法を用、いて精製した例を
比較例に示した。In addition, an example of manufacturing a fragrance material containing an off-flavor component is shown as a reference example, and an example of purifying this material using a conventional purification method is shown as a comparative example.
参考例1
4(or3)−(4’−ヒドロキシ−4′−メチルペン
チル)−Δ3−シクロヘキセンー1−力ルボキシアルデ
ヒドの製造:
密封容器中に90grのミルセノール(1) 、34g
rのアクロレイン(2)及び0.5grのハイドロキノ
ンを入れ、攪拌しながら4.5時間、150°Cに加熱
した。反応器を冷却し、内容物を取り出し、減圧分溜し
た。初め未反応不活性異性体C1゜アルコールを溜去し
た後、沸点136〜138℃/2mm11gの生成物1
10grを得た。この生成物は4−(4’−ヒドロキシ
−4′−メチルペンチル)−Δ3−シクロヘキセンー1
−カルボキシアルデヒド(3)と3−(4’−ヒドロキ
シ−4′−メチルペンチル)−Δ3−シクロヘキセン=
1−力ルボキシアルデヒド(4)の約7:3の混合物で
あり、約0.4%の4(or 3 )−(4’−メチル
ペンテニル)−Δ3−シクロヘキセンー1−カルボキシ
アルデヒド(5)を含有していた。Reference Example 1 Production of 4(or3)-(4'-hydroxy-4'-methylpentyl)-Δ3-cyclohexene-1-carboxaldehyde: 90 gr of myrcenol (1), 34 g in a sealed container
r acrolein (2) and 0.5 gr hydroquinone were added and heated to 150°C for 4.5 hours with stirring. The reactor was cooled and the contents were removed and fractionated under reduced pressure. After distilling off the initially unreacted inert isomer C1° alcohol, a product 1 with a boiling point of 136-138°C/2 mm 11 g was obtained.
Obtained 10 gr. This product is 4-(4'-hydroxy-4'-methylpentyl)-Δ3-cyclohexene-1
-Carboxaldehyde (3) and 3-(4'-hydroxy-4'-methylpentyl)-Δ3-cyclohexene=
About 7:3 mixture of 1-carboxaldehyde (4) and about 0.4% 4(or 3 )-(4'-methylpentenyl)-Δ3-cyclohexene-1-carboxaldehyde (5) It contained.
比較例1
蒸留による従来の精製:参考例1により得られた生成物
80grを蒸留により減圧分溜した。初め副生成物であ
る(5)を溜去した後、沸点138〜139℃/ 2m
m11gの生成物70grを得た。このものは本来の好
ましい匂いである甘いライラックーリリー芳香臭はほと
んどなく、柑橘系及び・メタリック様の異臭が残存し、
香料素材には適さなかった。Comparative Example 1 Conventional purification by distillation: 80 gr of the product obtained in Reference Example 1 was fractionated under reduced pressure by distillation. After distilling off the by-product (5), the boiling point was 138-139℃/2m
70 gr of product of 11 g was obtained. This product has almost no sweet lilac-lily aroma, which is the original pleasant smell, and a citrus and metallic odor remains.
It was not suitable as a fragrance material.
実施例1−a
参考例1で得られた生成物100grを第1図の反応容
器に入れ系内を40mmHHに保ちなから120℃に加
熱した。前記条件下、系内に約60℃の水蒸気を徐々に
吹き込み得られる溜升を冷却管部で凝縮させ捕集した。Example 1-a 100g of the product obtained in Reference Example 1 was placed in the reaction vessel shown in Fig. 1 and heated to 120°C while maintaining the inside of the system at 40mmHH. Under the above conditions, water vapor at about 60° C. was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section.
水蒸気の吹き込み量が40grになった時点で吹き込み
を終了した。この時溜出した油層は4grであった。次
いで室温に冷却し、内容物を取り出した。このものは、
比較例1に記載の異臭は残存せず、好ましい甘いライラ
ックーリリー芳香臭を有していた。Blowing was terminated when the amount of water vapor blown reached 40 gr. The oil layer distilled out at this time was 4gr. It was then cooled to room temperature and the contents were removed. This thing is
The off-flavor described in Comparative Example 1 did not remain, and the product had a pleasant sweet lilac lily aromatic odor.
実施例1−b
比較例1で得られた生成物を用いた他は実施例1−aと
同様の操作で行った。比較例1で得られた生成物70g
rを第1図の反応容器に入れ系内を40mm)Igに保
ちながら120℃に加熱した。前記条件下、系内に約6
0℃の水蒸気を徐々に吹き込み、得られる溜升を冷却管
部で凝縮させ捕集した。水蒸気の吹き込み量が15gr
になった時点で吹き込みを終了した。この時溜出した油
層は1grであった。次いで室温に冷却して内容物を取
り出した。このものは、比較例1に記載の異臭は除去さ
れており、好ましい甘い与イラ7クーリリー芳香臭を有
していた。Example 1-b The same procedure as in Example 1-a was carried out except that the product obtained in Comparative Example 1 was used. 70g of product obtained in Comparative Example 1
r was placed in the reaction vessel shown in Fig. 1 and heated to 120°C while maintaining the inside of the system at 40 mm)Ig. Under the above conditions, about 6
Steam at 0° C. was gradually blown into the reactor, and the resulting reservoir was condensed and collected in the cooling pipe section. The amount of water vapor blown is 15g.
I finished blowing when it reached . The oil layer distilled out at this time was 1 gr. It was then cooled to room temperature and the contents were taken out. The off-flavor described in Comparative Example 1 was removed from this product, and it had a desirable sweet aromatic odor.
参考例2
α−へキシルシンナミックアルデヒドの製造:〕
11の4ツロフラスコに258.4grのメタノール、
水45.6gr、40%水酸化ナトリウム水溶液30.
1gr、ジフェニルアミン1.3gr 、ベンズアルデ
ヒド(6) 218.7grを入れ攪拌した。系内を4
0℃以下に保ちつつ、オクチルアルデヒド129.9g
rを滴下し、次いで30分攪拌した。次いで水34.8
gr、35%塩酸水溶液23.2grを加え中和した後
、系内を100°Cに加熱しメタノールを溜去した。Reference Example 2 Production of α-hexyl cinnamic aldehyde: 258.4 gr of methanol in 11 4 flasks,
Water 45.6g, 40% sodium hydroxide aqueous solution 30.
1gr of diphenylamine, 1.3gr of diphenylamine, and 218.7gr of benzaldehyde (6) were added and stirred. 4 within the system
129.9g of octylaldehyde while keeping the temperature below 0℃
Then, the mixture was stirred for 30 minutes. Then water 34.8
After neutralizing by adding 23.2 gr of 35% hydrochloric acid aqueous solution, the system was heated to 100°C and methanol was distilled off.
次いで、系内を室温まで冷却し二層分離した。Next, the system was cooled to room temperature and separated into two layers.
得られた油層を減圧分溜した。初め未反応ベンズアルデ
ヒド(6)を溜去した後沸点150〜155”C/ 3
mm11gの生成物204grを得た。The obtained oil layer was fractionated under reduced pressure. After distilling off the initially unreacted benzaldehyde (6), the boiling point is 150-155"C/3
204 gr of product of 11 g mm were obtained.
比較例2
蒸留による従来の精製:参考例2で得られた生成物18
0grを減圧蒸留した。初め、微量残存会
しているベンズアルデヒド(6)を溜去した後、沸点1
50〜151 ’C/ 3 mm1(jの生成物172
grを得た。このものは、本来のジャスミン様の芳香臭
の他に強いベンズアルデヒド臭が残存し、香料素材には
適さなかった。Comparative Example 2 Conventional purification by distillation: Product 18 obtained in Reference Example 2
0gr was distilled under reduced pressure. Initially, after distilling off the trace amount of benzaldehyde (6) remaining, the boiling point was 1.
50-151'C/3 mm1 (product of j 172
I got gr. This product had a strong benzaldehyde odor in addition to the original jasmine-like aromatic odor, and was not suitable as a fragrance material.
実施例2−a
参考例2で得られた生成物200grを第1図の反応容
器に入れ系内を50mmHgに保ちつつ、110℃に加
熱した。前記条件下、系内に約60℃の水蒸気を徐々に
吹き込み、得られる溜升を冷却管部で凝縮させ捕集した
。水蒸気の吹き込み量が35grになった時点で吹き込
みを終了した。この時溜出した油層は4grであった。Example 2-a 200g of the product obtained in Reference Example 2 was placed in the reaction vessel shown in Fig. 1 and heated to 110°C while maintaining the inside of the system at 50mmHg. Under the above conditions, water vapor at about 60°C was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section. Blowing was terminated when the amount of water vapor blown reached 35 gr. The oil layer distilled out at this time was 4gr.
次いで室温に冷却して内容物を取り出した。このものは
、比較例2に記載のベンズアルデヒド臭は残存せず、好
ましいジャスミン様の芳香臭を有していた。It was then cooled to room temperature and the contents were taken out. This product did not have the benzaldehyde odor described in Comparative Example 2 and had a desirable jasmine-like aromatic odor.
実施例2−b
比較例2で得られた生成物を用いた他は実施例2−aと
同様の操作で行った。比較例2で得られた生成物170
grを第1図の反応容器に入れ系内を50mm)Igに
保ちつつ、110℃に加熱した。前記条件下、系内に約
60℃の水蒸気を徐々に吹き込み、得られる溜升を冷却
管部で凝縮させ捕集した。水蒸気の吹き込み量が15g
rになった時点で吹き込みを終了した。この時溜出した
油層はIgrであった。次いで室温に冷却して内容物を
取り出した。このものは、比較例2に記載のベンズアル
デヒド臭は除去されており、好ましいジャスミン様の芳
香臭を有していた。Example 2-b The same procedure as in Example 2-a was carried out except that the product obtained in Comparative Example 2 was used. Product 170 obtained in Comparative Example 2
gr was placed in the reaction vessel shown in Figure 1 and heated to 110° C. while maintaining the inside of the system at 50 mm) Ig. Under the above conditions, water vapor at about 60°C was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section. The amount of water vapor blown is 15g.
Blowing was finished when the temperature reached r. The oil layer distilled out at this time was Igr. It was then cooled to room temperature and the contents were taken out. This product had the benzaldehyde odor described in Comparative Example 2 removed and had a desirable jasmine-like aromatic odor.
参考例3
ジヒドロ−ツルージシクロペンタジェニルアセテートの
製造:
500cc 4ツロフラスコに99%酢酸135gr
、三フッ化ホウ素二酢酸7grを入れ、攪拌しなから8
5°Cに昇温し、ジシクロペンタジェン261grを滴
下した。次いで110℃で2時間攪拌し、20%水酸化
ナトリウム水溶液で中和した。中和後室温に冷却し、二
層分離して油層370grを取り出した。このものを減
圧分溜した。初め未反応のジシクロペンタジェン(9)
を溜去し沸点100〜105℃/ 5 mm11gのジ
ヒドロ−ツルージシクロペンタジェニルアセテートの異
性体(10)、(11)の混合物307grを得た。Reference Example 3 Production of dihydro-true dicyclopentadienyl acetate: 135 gr of 99% acetic acid in a 500 cc 4 flask
, add 7g of boron trifluoride diacetic acid and stir without stirring.
The temperature was raised to 5°C, and 261 gr of dicyclopentadiene was added dropwise. The mixture was then stirred at 110° C. for 2 hours and neutralized with a 20% aqueous sodium hydroxide solution. After neutralization, the mixture was cooled to room temperature, separated into two layers, and 370 gr of an oil layer was taken out. This product was fractionated under reduced pressure. Initially unreacted dicyclopentadiene (9)
was distilled off to obtain 307 gr of a mixture of dihydro-true dicyclopentagenylacetate isomers (10) and (11) with a boiling point of 100-105°C/5 mm and 11 g.
比較例3
蒸留による従来の精製:参考例3により得られた生成物
300grを減圧分溜した。初め微量残存しているジシ
クロペンタジェン(9)を溜去し沸点100〜lO2℃
/ 5 mmHHの生成物249 grを得た。このも
のは本来の新鮮なウツディ調の芳香臭の他に原料のジシ
クロペンタジェン臭及び酸臭があり香料素材には適さな
かった。Comparative Example 3 Conventional purification by distillation: 300 gr of the product obtained in Reference Example 3 was fractionated under reduced pressure. Dicyclopentadiene (9), which remained in trace amounts at first, was distilled off to a boiling point of 100 to 102°C.
249 gr of product of /5 mmHH were obtained. This product had a dicyclopentadiene odor and an acid odor from the raw material in addition to the original fresh, Utsy-like aromatic odor, and was not suitable as a fragrance material.
実施例3−a
参考例3により得られた生成物300grを第1図の反
応容器に入れ系内を50+nmHHに保ちつつ、100
℃に加熱した。前記条件下、系内に約60℃の水蒸気を
徐々に吹き込み、得られる溜升を冷却管部で′a縮させ
捕集した。水蒸気の吹き込み量がloOgrになった時
点で吹き込みを終了した。Example 3-a 300g of the product obtained in Reference Example 3 was placed in the reaction vessel shown in Fig. 1 and heated to 100g while maintaining the inside of the system at 50+nmHH.
heated to ℃. Under the above conditions, water vapor at about 60°C was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section. Blowing was terminated when the amount of water vapor blown reached loOgr.
この時溜出した油層は9grであった。次いで室温に冷
却して内容物を取り出した。このものは、比較例3に記
載の異臭は残存せず、好ましい新鮮なウツディ調の芳香
臭を有していた。The oil layer distilled out at this time was 9gr. It was then cooled to room temperature and the contents were taken out. This product did not have the residual odor described in Comparative Example 3, and had a desirable fresh, woody aromatic odor.
実施例3−b
比較例3により得られた生成物を用いた他は実施例3−
aと同様の方法で行った。比較例3で得られた生成物2
00grを第1図の反応容器に入れ系内を50mm11
gに保ちつつ、100℃に加熱した。Example 3-b Example 3-b except that the product obtained in Comparative Example 3 was used.
It was carried out in the same manner as in a. Product 2 obtained in Comparative Example 3
00gr into the reaction vessel shown in Figure 1 and the inside of the system is 50mm11.
The mixture was heated to 100° C. while maintaining the temperature at 100° C.
前記条件下、系内に約60℃の水蒸気を徐々に吹き込み
、得られる溜升を冷却管部で13縮させ捕集した。水蒸
気の吹き込み量が30grになった時点で吹き込みを終
了した。この時溜出した油層は2grであうた。次いで
室温に冷却し、内容物を取り出した。このものは、比較
例3に記載のジシクロペンタジェン臭及び酸臭は除去さ
れており、好ましい新鮮なウツディ調の芳香臭を有して
いた。Under the above conditions, water vapor at about 60° C. was gradually blown into the system, and the resulting distillate was condensed in the cooling pipe section and collected. Blowing was terminated when the amount of water vapor blown reached 30 gr. The oil layer distilled out at this time was 2gr. It was then cooled to room temperature and the contents were removed. This product had the dicyclopentadiene odor and acid odor described in Comparative Example 3 removed, and had a preferable fresh, woody aromatic odor.
参考例4
4−(2,6,6−トリメチル−2(orl) −シ
クロヘキセ−1−ニル)−3−ブテン−2−オン(イオ
ノン)の製造:
11の4ツロフラスコに6.10−ジメチル−3゜5.
9−ウンデカトリエン−2−オン(シュードイオノン)
(12)400gr 、シクロヘキサン200grを
入れ、90℃に加熱攪拌した。ここに85%リン酸水溶
液80grを滴下し、1時間攪拌した。次いで5%水酸
化ナトリウム水溶液840grを加え、中和した後、二
層分離した。得られた油層を分溜した。初めシクロヘキ
サンを溜去した後、沸点120−124℃/lommH
gの生成物360grを得た。Reference Example 4 Production of 4-(2,6,6-trimethyl-2(orl)-cyclohex-1-yl)-3-buten-2-one (ionone): 6.10-dimethyl- 3゜5.
9-Undecatrien-2-one (pseudoionone)
(12) 400g of cyclohexane and 200g of cyclohexane were added, and the mixture was heated and stirred at 90°C. 80g of 85% phosphoric acid aqueous solution was added dropwise thereto, and the mixture was stirred for 1 hour. Next, 840 gr of a 5% aqueous sodium hydroxide solution was added to neutralize the mixture, and then the mixture was separated into two layers. The obtained oil layer was fractionated. After first distilling off cyclohexane, the boiling point was 120-124℃/lommH.
360 gr of product were obtained.
このものは4−(2,6,6−トリメチル−2−シクロ
ヘキセ−1−ニル)−3−ブテン−2−オン(13)と
4−(2,6,6−ドリメチルー1−シクロヘキセ−1
−ニル)−3−ブテン−2−オン(14)の約7=2の
混合物であった。This compound contains 4-(2,6,6-trimethyl-2-cyclohex-1-yl)-3-buten-2-one (13) and 4-(2,6,6-trimethyl-1-cyclohex-1-yl)
-nyl)-3-buten-2-one (14).
比較例4
蒸留による従来の精製:参考例4により得られた生成物
360 grを蒸留により減圧分溜し、沸点12’1〜
122℃/10mm11gの生成物290 grを得た
。Comparative Example 4 Conventional purification by distillation: 360 gr of the product obtained in Reference Example 4 was fractionated under reduced pressure by distillation, and the boiling point was 12'1~
290 gr of product was obtained at 122°C/10 mm.
このものは本来の好ましい甘い花香芳香臭の他にアルデ
ヒド様及び海草様の異臭が存在し、香 。This product has an aldehyde-like and seaweed-like off-odor in addition to the original pleasant sweet floral aromatic odor, making it a fragrance.
料素材には適さなかった。It was not suitable as a food material.
実施例4−a
参考例4で得られた生成物360grを第1図の反応容
器に入れ系内を50no++1gに保ちながら70℃に
加熱した。前記条件下、系内に約60℃の水蒸気を徐々
に吹き込み、得られる溜升を冷却管部で凝縮させ捕集し
た。水蒸気の吹き込み量が70grになった時点で吹き
込みを終了した。この時、溜出した油層は?grであっ
た。次いで室温に冷却し、内容物を取り出した。このも
のは、比較例4に記載の異臭は残存せず、好ましい甘い
花香芳香臭を存していた。Example 4-a 360g of the product obtained in Reference Example 4 was placed in the reaction vessel shown in Fig. 1 and heated to 70°C while maintaining the inside of the system at 50no++1g. Under the above conditions, water vapor at about 60°C was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section. Blowing was terminated when the amount of water vapor blown reached 70 gr. What was the oil layer that was deposited at this time? It was gr. It was then cooled to room temperature and the contents were removed. This product did not have the residual odor described in Comparative Example 4, but had a pleasant sweet floral aromatic odor.
実施例4−b
比較例4で得られた生成物を用いた他は実施例4−aと
同様の操作で行った。比較例4で得られた生成物250
grを第1図の反応容器に入れ系内を50mm11gに
保ちながら、70℃に加熱した。前記条件下、系内に約
60℃の水蒸気を徐々に吹き込み、得られる溜升を冷却
管部で凝縮させ捕集した。水蒸気の吹き込み量が25g
rになった時点で吹き込みを終了した。この時、溜出し
た油層は2grであった。次いで室温に冷却し、内容物
を取り出した。このものは、比較例4に記載の異臭は除
去されており、好ましい甘い花香芳香臭を有していた。Example 4-b The same procedure as in Example 4-a was carried out except that the product obtained in Comparative Example 4 was used. Product obtained in Comparative Example 4 250
gr was placed in the reaction vessel shown in Fig. 1 and heated to 70° C. while maintaining the inside of the system at 50 mm and 11 g. Under the above conditions, water vapor at about 60°C was gradually blown into the system, and the resulting volume was condensed and collected in the cooling pipe section. The amount of water vapor blown is 25g.
Blowing was finished when the temperature reached r. At this time, the oil layer distilled out was 2 gr. It was then cooled to room temperature and the contents were removed. The off-flavor described in Comparative Example 4 was removed from this product, and it had a desirable sweet floral aromatic odor.
本発明の方法によれば、香料の主成分の沸点より低い比
較的低温で異臭成分を除去できるので、熱的に不安定な
官能基、例えばアルデヒド、ケトン、アルコール、エー
テル、エステル、ラクトン、オレフィンなどを有する化
合物を主成分あるいは不純物に有する香料素材の精製に
有効である。特に、蒸留により精製した後、新たに発生
する蒸留臭、刺激臭その他種々の低沸化合物に由来する
異臭の除去に有効である。また、本発明の方法は、従来
の精製法では除去しきれない異臭成分を除去するのに有
効である。According to the method of the present invention, off-flavor components can be removed at a relatively low temperature lower than the boiling point of the main components of fragrances, so thermally unstable functional groups such as aldehydes, ketones, alcohols, ethers, esters, lactones, and olefins can be removed. It is effective for purifying fragrance materials containing compounds such as as main components or impurities. In particular, it is effective in removing distillation odor, pungent odor, and other foreign odors originating from various low-boiling compounds that are newly generated after purification by distillation. Furthermore, the method of the present invention is effective in removing off-flavor components that cannot be removed by conventional purification methods.
第1図は本発明の方法を実施するための装置の一例を示
す図である。FIG. 1 is a diagram showing an example of an apparatus for implementing the method of the present invention.
Claims (1)
とを特徴とする香料素材の精製法。 2、異臭成分を含有する香料素材が、蒸留法あるいは晶
析法による精製工程を経たものである特許請求の範囲第
1項記載の香料素材の精製法。[Claims] 1. A method for purifying a fragrance material, which comprises blowing steam into a fragrance material containing an off-flavor component. 2. The method for purifying a fragrance material according to claim 1, wherein the fragrance material containing an off-flavor component has undergone a purification process by a distillation method or a crystallization method.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28047285A JPS62141097A (en) | 1985-12-13 | 1985-12-13 | Purification of perfume base material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28047285A JPS62141097A (en) | 1985-12-13 | 1985-12-13 | Purification of perfume base material |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62141097A true JPS62141097A (en) | 1987-06-24 |
Family
ID=17625549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP28047285A Pending JPS62141097A (en) | 1985-12-13 | 1985-12-13 | Purification of perfume base material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62141097A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102531858A (en) * | 2010-12-16 | 2012-07-04 | 杭州格林香料化学有限公司 | Preparation method of lyral |
-
1985
- 1985-12-13 JP JP28047285A patent/JPS62141097A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102531858A (en) * | 2010-12-16 | 2012-07-04 | 杭州格林香料化学有限公司 | Preparation method of lyral |
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