JPS5811934B2 - Menthone manufacturing method - Google Patents
Menthone manufacturing methodInfo
- Publication number
- JPS5811934B2 JPS5811934B2 JP52072771A JP7277177A JPS5811934B2 JP S5811934 B2 JPS5811934 B2 JP S5811934B2 JP 52072771 A JP52072771 A JP 52072771A JP 7277177 A JP7277177 A JP 7277177A JP S5811934 B2 JPS5811934 B2 JP S5811934B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- menthone
- reaction
- epoxide
- perchloric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 title claims description 11
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 title claims description 11
- 229930007503 menthone Natural products 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 150000002118 epoxides Chemical class 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 238000006317 isomerization reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YYCPSEFQLGXPCO-UHFFFAOYSA-N xi-p-Menth-3-ene Chemical compound CC(C)C1=CCC(C)CC1 YYCPSEFQLGXPCO-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は３−メンセンエポキシドからメントンを製造す
る方法、更に詳細には、３−メンセンエポキシドを過塩
素酸を触媒として異性化してメントンを製造する方法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing menthone from 3-mensen epoxide, and more particularly to a method for producing menthone by isomerizing 3-mensen epoxide using perchloric acid as a catalyst.
本発明を反応式で示せば次のとうりである。The reaction formula of the present invention is as follows.
エポキシ基を触媒により異性化してカルボニル化加物を
得ることは既に知られている。It is already known to obtain carbonylated adducts by isomerizing epoxy groups with catalysts.
従来この触媒としてはルイス酸、例えば臭化マグネシウ
ム。Traditionally, this catalyst has been a Lewis acid, such as magnesium bromide.
エーテル化合物、塩化亜鉛・エーテル化合物、３弗化ホ
ウ素・エーテル化合物、塩化アルミニウム、硫酸、パラ
トルエンスルホン酸、イオン交換樹脂（酸型）、あるい
は固体リン酸、アルミナ等の固体酸等が報告されている
。Ether compounds, zinc chloride/ether compounds, boron trifluoride/ether compounds, aluminum chloride, sulfuric acid, para-toluenesulfonic acid, ion exchange resins (acid type), solid acids such as solid phosphoric acid, alumina, etc. have been reported. There is.
そこで、本発明者は各種ルイス酸および固体酸を触媒と
して使用して３−メンセンエポキシド（■）を異性化せ
んと種々試みたが、過塩素酸以外ではメントンが全く生
成しないか、もしくは生成しても極めて少量で実用に供
し得るものではなく、過塩素酸が特異的に好収率でメン
トンを与えることを見出し、本発明を完成した。Therefore, the present inventor made various attempts to isomerize 3-mencene epoxide (■) using various Lewis acids and solid acids as catalysts, but menthone was not produced at all or was not produced using methods other than perchloric acid. However, the present invention was completed based on the discovery that perchloric acid can specifically give menthone in a good yield.
このような本発明方法は、リモネンより３−メンセンを
経て合成メントールを製造するための工程として重要な
ものである。Such a method of the present invention is important as a process for producing synthetic menthol from limonene via 3-menthene.
本発明の過塩素酸は市場において入手できる６０〜６５
％水溶液を使用するのが便利であり、これは有機溶剤で
希釈して使用するのが好ましい有機溶剤としては、例え
ばメタノール、エタノール、イソプロパツール等のアル
コール類；アセトン、メチルエチルケトン等のケトン類
；ジオキサン等のエーテル類；酢酸等の酸類が挙げられ
、過塩素酸水溶液と有機溶剤の割合は１対２（重量）が
好適である。The perchloric acid of the present invention is commercially available.
It is convenient to use a % aqueous solution, which is preferably diluted with an organic solvent. Examples of organic solvents include alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone and methyl ethyl ketone; Examples include ethers such as dioxane; acids such as acetic acid; the ratio of perchloric acid aqueous solution to organic solvent is preferably 1:2 (by weight).
触媒の使用量は３−メンセンエポキシドに対し過塩素酸
として０．１〜０．５重量％が好適であるが、触媒量を
増すと反応速度が促進されるので５％位まで適宜増量し
て使用することができる。The amount of catalyst used is preferably 0.1 to 0.5% by weight of perchloric acid based on 3-mencene epoxide, but increasing the amount of catalyst accelerates the reaction rate, so increase the amount appropriately to about 5%. can be used.
反応温度は１００℃以下、好適には室温以下で実施され
る。The reaction temperature is 100° C. or lower, preferably room temperature or lower.
反応の進行は反応液の色で判断でき、始めは無色である
が次第に変化し、褐色に変化した時が反応の終了を示す
。The progress of the reaction can be judged by the color of the reaction solution, which is initially colorless but gradually changes to brown, indicating the end of the reaction.
このようにして異性化反応を行った場合、通常メントン
の収率は８０％で、その他に３，４−パラメンタンジオ
ールが１０％、他の副生物１０％が得られる。When the isomerization reaction is carried out in this manner, the yield of mentone is usually 80%, in addition to which 10% of 3,4-paramenthanediol and 10% of other by-products are obtained.
この３，４−パラメンタンジオールは公知方法〔Ｈｅ１
ｖ、Ｃｈｉｍ、Ａｃｔａ ４２，１１７４−１１７７．
１２３７−１２３８（１９５９）〕によって、硫酸で脱
水して好収率でメントンに導くことができる。This 3,4-paramenthanediol was prepared by a known method [He1
v. Chim, Acta 42, 1174-1177.
1237-1238 (1959)], it can be dehydrated with sulfuric acid to lead to menthone in good yield.
上記の如くして得られた異性化反応物はそのまま硫酸で
処理するか、あるいは蒸留で分留して３゜４−パラメン
タンジオールを一旦分離し、これを硫酸で処理してもよ
く、斯くすれば総合収率８５〜９０％でメントンを得る
ことができる。The isomerization reaction product obtained as described above may be treated with sulfuric acid as it is, or it may be fractionated by distillation to once separate 3゜4-paramenthanediol and then treated with sulfuric acid. Menthone can then be obtained with an overall yield of 85-90%.
次に実施例及び比較例を挙げて説明する。Next, examples and comparative examples will be given and explained.
実施例 １
６０％過塩素酸水溶液１重量部とイソプロパツール２重
量部を混和して触媒液を調製する。Example 1 A catalyst solution is prepared by mixing 1 part by weight of a 60% aqueous perchloric acid solution and 2 parts by weight of isopropanol.
３−メンセンエポキシド１００ｇを５００ｍ１容コルベ
ンに入れ、５℃に冷却し、攪拌下に上記触媒液１ｇを徐
々に滴下する。100 g of 3-mensen epoxide was placed in a 500 ml Kolben, cooled to 5° C., and 1 g of the above catalyst solution was gradually added dropwise while stirring.
その後後温度を２５℃に保って３時間攪拌を続けると反
応液は無色から褐色に変化する。Thereafter, the temperature was kept at 25° C. and stirring was continued for 3 hours, and the reaction solution changed from colorless to brown.
反応液に５％苛性ソーダ液を加えて中和し、油層を分離
する。A 5% caustic soda solution is added to the reaction solution to neutralize it, and the oil layer is separated.
ここに得た油層を減圧蒸留して８５〜ｂ ８０ｇ（収率８０％）を得た。The oil layer obtained here is distilled under reduced pressure to obtain 85-b 80 g (80% yield) was obtained.
さらに減圧蒸留をつづけ１２９〜ｂ パラメンタンジオール１１ｇを得た。Further vacuum distillation continues 129-b 11 g of paramenthanediol was obtained.
実施例 ２
６０％過塩素酸水溶液１重量部とイソプロパツール２重
量部を混和して触媒液を調製する。Example 2 A catalyst solution is prepared by mixing 1 part by weight of a 60% aqueous perchloric acid solution and 2 parts by weight of isopropanol.
３−メンセンエポキシド１００ｇを５００ｍ１容コルベ
ンに入れ、５℃に冷却し、攪拌下に上記触媒液１ｇを徐
々に滴下する。100 g of 3-mensen epoxide was placed in a 500 ml Kolben, cooled to 5° C., and 1 g of the above catalyst solution was gradually added dropwise while stirring.
その後温度を２５℃に保って攪拌を続けると反応液は無
色から褐色に変化する。Thereafter, when stirring is continued while maintaining the temperature at 25°C, the reaction liquid changes from colorless to brown.
反応液に５％苛性ソーダ液を加えて中和し、油層を分離
する。A 5% caustic soda solution is added to the reaction solution to neutralize it, and the oil layer is separated.
油層に濃硫酸０．１ｇを加え、１４０℃にて１時間加熱
攪拌し、冷却後５％苛性ソーダ液で洗浄し、更に水で２
回水洗し、油層を減圧蒸留してメントン８９ｇ（収率８
９％）を得た。0.1 g of concentrated sulfuric acid was added to the oil layer, heated and stirred at 140°C for 1 hour, cooled, washed with 5% caustic soda solution, and further washed with water for 2 hours.
After washing twice with water, the oil layer was distilled under reduced pressure to 89g of menthone (yield: 8.
9%).
実施例 ３
実施例２におけるイソプロパツールの代りにメタノール
を使用する以外は実施例２と同様に処理して、メントン
８７ｇ（収率８７％）を得た。Example 3 87 g (yield: 87%) of menthone was obtained in the same manner as in Example 2 except that methanol was used instead of isopropanol in Example 2.
実施例 ４
実施例２におけるイソプロパツールの代りにアセトンを
使用する以外は実施例２と同様に処理して、メントン８
５ｇ（収率８５％）を得た。Example 4 Menthone 8
5 g (85% yield) was obtained.
比較例
３−メンセンエポキシドの異性化触媒として公知の各種
触媒を使用し、３−メンセンエポキシドの異性化を行っ
た。Comparative Example 3 - Isomerization of 3-mensen epoxide was carried out using various known catalysts as catalysts for isomerization of 3-mensen epoxide.
反応は実施例１に準じて行い、触媒の使用量及び反応条
件は触媒の種類に応じて選定した。The reaction was carried out according to Example 1, and the amount of catalyst used and reaction conditions were selected depending on the type of catalyst.
反応結果は、反応終了後、反応液を蒸留して留出分を採
取し、これをガスクロマトグラフィー分析によって測定
して求めた。The reaction results were determined by distilling the reaction solution after the reaction was completed, collecting a distillate, and measuring the distillate by gas chromatography analysis.
尚表中の触媒の使用量は３−メンセンエポキシドに対す
る重量係で示し、「イオン交換樹脂」は「アンバーリス
ト−１５」（ローム・アンド・ハース社製、強酸性陽イ
オン交換ＭＲ型）を使用した。In addition, the amount of catalyst used in the table is indicated by weight relative to 3-mensen epoxide, and the "ion exchange resin" is "Amberlyst-15" (manufactured by Rohm and Haas, strong acid cation exchange MR type). used.
その結果は次表のとおりである。The results are shown in the table below.
Claims (1)
化せしめることを特徴とするメントンの製法。 ２ 触媒が過塩素酸の６０％以上の水溶液を有機溶剤で
希釈したものである特許請求の範囲第１項記載の製法。 ３ 有機溶剤がメタノール、エタノール、イソプロパツ
ール、アセトン、ジオキサンまたは酢酸である特許請求
の範囲第２項記載の製法。 ４ 触媒量が、３−メンセンエポキシドに対し過塩素酸
として０．１〜５重量％である特許請求の範囲第１項記
載の製法。 ５ 異性化反応を１００℃以下の温度で、反応液が褐色
になるまで行う特許請求の範囲第１項記載の製法。[Claims] A method for producing menthone, which comprises isomerizing 13-mencene epoxide using perchloric acid as a catalyst. 2. The manufacturing method according to claim 1, wherein the catalyst is a 60% or more aqueous solution of perchloric acid diluted with an organic solvent. 3. The manufacturing method according to claim 2, wherein the organic solvent is methanol, ethanol, isopropanol, acetone, dioxane, or acetic acid. 4. The method according to claim 1, wherein the catalyst amount is 0.1 to 5% by weight of perchloric acid based on 3-mensen epoxide. 5. The production method according to claim 1, in which the isomerization reaction is carried out at a temperature of 100° C. or lower until the reaction solution turns brown.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52072771A JPS5811934B2 (en) | 1977-06-21 | 1977-06-21 | Menthone manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52072771A JPS5811934B2 (en) | 1977-06-21 | 1977-06-21 | Menthone manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS549247A JPS549247A (en) | 1979-01-24 |
| JPS5811934B2 true JPS5811934B2 (en) | 1983-03-05 |
Family
ID=13498962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52072771A Expired JPS5811934B2 (en) | 1977-06-21 | 1977-06-21 | Menthone manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5811934B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS611229A (en) * | 1984-06-11 | 1986-01-07 | 松下電工株式会社 | Quick charging circuit |
| JPS633628A (en) * | 1986-06-21 | 1988-01-08 | 東芝テック株式会社 | Charging circuit |
| JPH03273829A (en) * | 1990-03-23 | 1991-12-05 | Shinko Electric Co Ltd | Charging controller of battery |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3535106A1 (en) * | 1985-10-02 | 1987-04-16 | Mtu Muenchen Gmbh | DEVICE FOR THE EXTERNAL SHEATHING OF THE BLADES OF AXIAL GAS TURBINES |
-
1977
- 1977-06-21 JP JP52072771A patent/JPS5811934B2/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS611229A (en) * | 1984-06-11 | 1986-01-07 | 松下電工株式会社 | Quick charging circuit |
| JPS633628A (en) * | 1986-06-21 | 1988-01-08 | 東芝テック株式会社 | Charging circuit |
| JPH03273829A (en) * | 1990-03-23 | 1991-12-05 | Shinko Electric Co Ltd | Charging controller of battery |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS549247A (en) | 1979-01-24 |
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