JPS5940809B2 - Method for producing P-methylacetophenone - Google Patents
Method for producing P-methylacetophenoneInfo
- Publication number
- JPS5940809B2 JPS5940809B2 JP5049082A JP5049082A JPS5940809B2 JP S5940809 B2 JPS5940809 B2 JP S5940809B2 JP 5049082 A JP5049082 A JP 5049082A JP 5049082 A JP5049082 A JP 5049082A JP S5940809 B2 JPS5940809 B2 JP S5940809B2
- Authority
- JP
- Japan
- Prior art keywords
- methylacetophenone
- oxygen
- mentadiene
- producing
- present
- 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
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- LFJQCDVYDGGFCH-JTQLQIEISA-N (+)-β-phellandrene Chemical compound CC(C)[C@@H]1CCC(=C)C=C1 LFJQCDVYDGGFCH-JTQLQIEISA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 239000003880 polar aprotic solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000238366 Cephalopoda Species 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007876 p-menthadiene derivatives Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- -1 terpene compounds Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は次の〒般式（Ｉ）
ウ
（但し、式中の点線は互いに連続しては存在しない２つ
の二重結合を示す）で表わされるｐ−メンタジエンから
次の一般式（Ｔｆ■）中 −
で表わされるｐ−メチルアセトフェノンを製造する方法
に係る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the following p-mentadiene represented by the following general formula (I) (however, the dotted line in the formula indicates two double bonds that are not consecutive to each other). The present invention relates to a method for producing p-methylacetophenone represented by - in the general formula (Tf).
前記一般式（Ｉ）に該当する化合物は環内に２つの二重
結合を有するｐ＝メンタジエンとして総称される一群の
テルペン系化合物で、ｐ−メンタジエンはさらに１ ・
３−ｐ−メンタジエン、１ ・４一ｐ−メンタジエン及
び１ ・５−ｐ−メンタジエンを包含している。The compounds corresponding to the general formula (I) are a group of terpene compounds collectively referred to as p=mentadiene, which have two double bonds in the ring, and p-mentadiene further has 1.
Includes 3-p-mentadiene, 1 .4-p-mentadiene and 1 .5-p-mentadiene.
本発明者等は今回これら１ ・ ３−ｐ−メンタジエン
、ｌ ・ ４−ｐ−メンタジエン、１ ・ ５−ｐ−メ
ンメジエンのいずれか１つまたは２つ以上の混合物を極
性非プロトン溶媒であるジメチルスルホオキシド（以下
ＤＭＳＯと略記する）中において加熱下に酸素又は含酸
素ガスを導入することによつてｐ−メチルアセトフェノ
ンをうる方法を発明したものである。The present inventors have now prepared any one or a mixture of two or more of these 1.3-p-mentadiene, 1.4-p-mentadiene, and 1.5-p-mentadiene in dimethylsulfonate, a polar aprotic solvent. This invention has invented a method for obtaining p-methylacetophenone by introducing oxygen or oxygen-containing gas into oxide (hereinafter abbreviated as DMSO) while heating.
本発明の方法を反応式で示すと下記のようになる。The reaction formula of the method of the present invention is as follows.
本発明で製造されるｐ−メチルアセトフエノンは香料ま
たは香料合成中間体として重要なものであり、またニカ
メイ蛾の幼虫の強力な誘引物質として稲から抽出された
オキシザノン（０ｘｙｚａｎ０ｎｅ）と同一物質であり
、現在斯界の注目を惹いている化合物である。p-Methylacetophenone produced in the present invention is important as a fragrance or a synthetic intermediate for fragrances, and is the same substance as oxyzanone extracted from rice, which is a strong attractant for the larvae of the Japanese squid moth. It is a compound that is currently attracting attention in the industry.
ｐ−メチルアセトフエノンは関：日化５２、８００〜８
０５（１９３１）によればｐ−シメンの硝酸酸化により
５１％の収率で得られ、０．Ｃ．Ｄｅｒｍｅｒ等：Ｊ．
Ａ．Ｃ．Ｓ．６３２８８ｌ〜２８８３（１９４１）によ
れば塩化アセチルとトルエンより塩化アルミニウム、塩
化モリブデン、塩化鉄、塩化錫等々多くの触媒を用いて
合成が試みられ、Ｇ．Ｍ．ＫＯｓＯｌａｐＯｆｆ（Ｊ．
Ａ．Ｃ．Ｓ．６９ｌ６５ｌ〜１６５２（１９４７）によ
れば、トルエンと氷酢酸を五酸化二燐の存在下反応させ
て得られている。p-Methylacetophenone Seki: Nikka 52, 800-8
05 (1931), p-cymene was obtained by oxidation with nitric acid in a yield of 51%, and 0. C. Dermer et al.: J.
A. C. S. According to G. 63288l-2883 (1941), synthesis was attempted from acetyl chloride and toluene using many catalysts such as aluminum chloride, molybdenum chloride, iron chloride, tin chloride, etc. M. KOsOlapOff (J.
A. C. S. According to 69l65l-1652 (1947), it is obtained by reacting toluene and glacial acetic acid in the presence of diphosphorus pentoxide.
現在、工業的にはトルエンと無水酢酸および塩化アルミ
ニウムから製造されているが収率が悪いのみならず、前
記いずれの方法でも反応装置の腐蝕の点で問題があり、
且つ副産物の廃棄についても環境汚染上難かしい問題が
残されている。本発明はこれらの欠点のほとんどを解決
したというべく工業化にとつてまことに有利なｐ−メチ
ルアセトフエノンの製造方法を提供するものである。Currently, it is produced industrially from toluene, acetic anhydride, and aluminum chloride, but not only is the yield poor, but all of the above methods also have problems in terms of corrosion of the reaction equipment.
In addition, the disposal of by-products remains a difficult problem in terms of environmental pollution. The present invention provides a method for producing p-methylacetophenone which is extremely advantageous for industrialization since it solves most of these drawbacks.
次に本発明の方法をさらに詳細に説明する。Next, the method of the present invention will be explained in more detail.
ｐ−メンメジエン化合物中、二重結合が環中に２個ある
もの、すなわち１・３−ｐ−メンタジエン、１・４−Ｐ
−メンタジエンおよび１・５−ｐメンタジエンは極性非
プロトン溶媒において、加熱下に酸素を１モル当量以上
を導入するとｐシメンを経て、選択的にかつ高収率を以
てｐ−メチルアセトフエノンを与える。溶媒の使用量は
一般に原料に対し５〜８倍重量が好ましい。反応に使用
された極性非プロトン溶媒は蒸留により回収して反復使
用でき、廃棄物はないので、本発明の方法を特に無公害
の方法として特徴づけている。また本発明の酸化は空気
中の酸素を利用しても十分目的を達成することが出来、
極めて経済的な方法である。酸素の導入速度は仕込量（
原料＋溶媒の全重量）の１／３容量／分（例えば仕込３
０ｙの場合は１０ｍ１／分）の速度を標準酸素導入速度
として好結果をうることができた。空気使用の場合、空
気は予め乾燥することが望ましい。反応温度は５０℃〜
１５０℃の範囲内で、特に好ましくは１００±５℃の範
囲で行うのがよい。なお本発明者らが特願昭５３−２２
０４１号において提案したようにリモネン〔１・８（９
）−ｐメンメジエン〕などのｐ−メンタジエン類からも
ｐ−メチルアセトフエノンをうることができ、本発明で
も実施例２においてリモネンを含む例を示した。Among p-menmediene compounds, those with two double bonds in the ring, i.e. 1,3-p-mentadiene, 1,4-P
When 1 molar equivalent or more of oxygen is introduced into -menthadiene and 1.5-p-menthadiene while heating in a polar aprotic solvent, p-cymene is converted to p-methylacetophenone selectively and in high yield. The amount of solvent used is generally preferably 5 to 8 times the weight of the raw material. The polar aprotic solvent used in the reaction can be recovered by distillation and used repeatedly and there is no waste, which characterizes the process of the invention as a particularly pollution-free process. In addition, the oxidation of the present invention can sufficiently achieve the purpose even if oxygen in the air is used.
This is an extremely economical method. The rate of introduction of oxygen is determined by the charging amount (
1/3 volume/min (for example, charge 3
Good results were obtained using a standard oxygen introduction rate of 10 m1/min (in the case of 0y). When using air, it is desirable to dry the air beforehand. Reaction temperature is 50℃~
The temperature is preferably 150°C, particularly preferably 100±5°C. The inventors of the present invention have filed a patent application
As proposed in No. 041, limonene [1.8 (9
p-methylacetophenone can also be obtained from p-mentadienes such as p-menthadienes], and in the present invention, an example containing limonene was shown in Example 2.
次に本発明の実施例を示す。Next, examples of the present invention will be shown.
実施例 １
還流冷却器、温度計、かき混ぜ機および空気導入管を備
えた１００ｍ１容の四頚フラスコに、１・３−ｐ−タン
汐ジエン３．４７（０．０２５モル）と、ＤＭＳＯ２７
７を採り、塩化カルシウム管及び硫酸を含む洗浄びんを
通じて乾燥した空気を１０ｍ１／分の送入速度で導入し
ながら１００℃の温度で４８時間の間、激しく内容物を
かき混ぜた。Example 1 In a 100 ml four-necked flask equipped with a reflux condenser, a thermometer, a stirrer and an air inlet tube, 3.47 (0.025 mol) of 1,3-p-tane diene and 27 DMSO were added.
7 was taken and the contents were vigorously stirred at a temperature of 100° C. for 48 hours while introducing dry air through a calcium chloride tube and a washing bottle containing sulfuric acid at a feed rate of 10 ml/min.
原料に対し約８倍モル当量に相当する酸素を含む空気を
導入した後、反応を止め、生成物を減圧蒸留に付し、１
０ｍｍＨｇの減圧において７０℃までの留分２５７（Ｄ
ＭＳＯ）を回収した。次に７ｍｍＨｇの減圧で沸点範囲
７３〜７３．５℃の留分３．５ｙを得た。この生成物は
ｐ−メチルアセトフエノンの物理恒数と全く一致してい
た。収率は理論の９５％であつた。実施例 ２
実施例１と同様の装置を用い、原料として市販のコリア
ンダ一油の中留分（リモネン約４５％、１・３−ｐ−メ
ンメジエン約１％、１・４−Ｐメンタジエン約３４％、
ｐ−シメン約１６％を含む）を用いた。After introducing air containing oxygen in an amount equivalent to about 8 times the molar equivalent of the raw material, the reaction was stopped and the product was subjected to vacuum distillation.
Fraction 257 (D
MSO) was collected. Next, a fraction 3.5y with a boiling point range of 73 to 73.5°C was obtained under reduced pressure of 7 mmHg. The physical constants of this product were completely consistent with the physical constants of p-methylacetophenone. The yield was 95% of theory. Example 2 Using the same equipment as in Example 1, a middle distillate of commercially available coriander oil was prepared as a raw material (about 45% limonene, about 1% 1,3-p-menmediene, about 34% 1,4-p-mentadiene). ,
(containing about 16% p-cymene) was used.
中留分３．４７とＤＭＳＯ２７７をとり、塩化カルシウ
ム管及び硫酸を含む洗浄びんを通じて乾燥した空気を１
０ｍ１／分の送入速度で導入しながら、１００℃で３０
時間、激しくかきまぜた。導入酸素量は原料に対し約５
倍モル当量である。得られた反応生成物を１０ｍｍＨｇ
の減圧下に蒸留し、下記の留分をえた。括弧内に成分名
を記した。尚前記中留分は８２分／４０ｍｍＨｇまでの
留分８．５％を除き、８３〜９０ｍ／４０７ｆＬｍＨｇ
の留分１８．３％をとつたものである。Take middle distillate 3.47 and DMSO 277, and add 1 ml of dry air through a calcium chloride tube and a washing bottle containing sulfuric acid.
30 at 100°C while introducing at a feed rate of 0 m1/min.
Stir vigorously for hours. The amount of oxygen introduced is approximately 5% relative to the raw material.
It is twice the molar equivalent. The obtained reaction product was heated to 10 mmHg.
The following fractions were obtained by distillation under reduced pressure. Component names are written in parentheses. Note that the middle distillate is 83-90m/407fLmHg, excluding 8.5% of the fraction up to 82min/40mmHg.
The fraction is 18.3%.
Claims (1)
、式中の点線は互いに連続しては存在しない２つの二重
結合を示す）で表わされるｐ−メンタジエンをジメチル
スルホオキシド溶媒中で加熱の下に酸素または含酸素ガ
スを導入して酸化することを特徴とするｐ−メチルアセ
トフェノンの製造方法。[Claims] 1 The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (However, the dotted lines in the formula indicate two double bonds that are not consecutive to each other. 1. A method for producing p-methylacetophenone, which comprises oxidizing p-menthadiene represented by the following formula in a dimethylsulfoxide solvent by introducing oxygen or an oxygen-containing gas while heating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5049082A JPS5940809B2 (en) | 1982-03-29 | 1982-03-29 | Method for producing P-methylacetophenone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5049082A JPS5940809B2 (en) | 1982-03-29 | 1982-03-29 | Method for producing P-methylacetophenone |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2204178A Division JPS54115326A (en) | 1978-03-01 | 1978-03-01 | Preparation of 1-methyl-4-ethylbenzene derivative by autoxidation of unsaturated-p-menthane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57183735A JPS57183735A (en) | 1982-11-12 |
| JPS5940809B2 true JPS5940809B2 (en) | 1984-10-03 |
Family
ID=12860360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5049082A Expired JPS5940809B2 (en) | 1982-03-29 | 1982-03-29 | Method for producing P-methylacetophenone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5940809B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4650599B2 (en) * | 2001-05-23 | 2011-03-16 | 日本ケミコン株式会社 | Electrolytic capacitor |
| WO2017090567A1 (en) * | 2015-11-27 | 2017-06-01 | 三井化学東セロ株式会社 | Packaging container, and package using same |
-
1982
- 1982-03-29 JP JP5049082A patent/JPS5940809B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57183735A (en) | 1982-11-12 |
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