JPH03181438A - Production of 4-isopropylcyclohexanone - Google Patents
Production of 4-isopropylcyclohexanoneInfo
- Publication number
- JPH03181438A JPH03181438A JP1320126A JP32012689A JPH03181438A JP H03181438 A JPH03181438 A JP H03181438A JP 1320126 A JP1320126 A JP 1320126A JP 32012689 A JP32012689 A JP 32012689A JP H03181438 A JPH03181438 A JP H03181438A
- Authority
- JP
- Japan
- Prior art keywords
- isopropylcyclohexanone
- isopropylphenol
- reaction
- selectivity
- solvent
- 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.)
- Pending
Links
- FPKISACHVIIMRA-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCC(=O)CC1 FPKISACHVIIMRA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 claims abstract description 40
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 37
- 238000000034 method Methods 0.000 abstract description 9
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract description 7
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 239000008096 xylene Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- DKKRDMLKVSKFMJ-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(O)CC1 DKKRDMLKVSKFMJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- -1 butyl hypochloride Chemical compound 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 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
Abstract
Description
【発明の詳細な説明】
皮果±旦祉里公立
本発明は、液相中、ｐ−イソプロピルフェノールを接触
還元する４−イソプロピルシクロヘキサノンの製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 4-isopropylcyclohexanone by catalytically reducing p-isopropylphenol in a liquid phase.
丈来坐狡歪
４−イソプロピルシクロヘキサノンは、重合体や医薬品
、香料等の製造中間原料として重要である。4-isopropylcyclohexanone is important as an intermediate raw material in the production of polymers, pharmaceuticals, fragrances, and the like.
従来、フェノールを気相で接触還元して、シクロヘキサ
ノンを製造する方法は、例えば、特開昭５０−１４９６
４９号公報、特開昭６２−１４４７４９号公報等に記載
されているように知られている。また、米国特許明細書
第３，０７６．８１０号には、フェノールを液相でパラ
ジウム触媒及びナトリウム化合物の存在下でｐＨを規制
して、接触的に水素還元して、シクロヘキサノンを製造
する方法が記載されているが、反応条件が？Ｊ雑であり
、特に、ｐＨ調整が容易ではない。Conventionally, a method for producing cyclohexanone by catalytic reduction of phenol in a gas phase has been described, for example, in JP-A-50-1496.
It is known as described in Japanese Patent Application Laid-open No. 49, Japanese Patent Application Laid-open No. 144749/1983, and the like. Additionally, US Pat. No. 3,076.810 describes a method for producing cyclohexanone by catalytically reducing the pH of phenol in the liquid phase in the presence of a palladium catalyst and a sodium compound. It is described, but what are the reaction conditions? It is difficult to adjust the pH in particular.
他方、４−イソプロピルシクロヘキサノンについては、
従来、例えば、Ｊ、＾−，Ｃｈｅｗ、 Ｓｏｃ、＋ ｇ
３６４６ （１９７３）やＪ、 Ａｍ、 Ｃｈｅ＋ｗ、
Ｓｏｃ、＋ ９５＋ ７５９９（１９７２）に記載さ
れているように、１−アミノアポカンファンをｔｅｒｔ
、−ブチルハイポクロライドにて塩素化して、ｌ−Ｎ、
Ｎ−シクロロアミノアポカンファンを得た後、塩化アル
ミニウムと反応させ、酸で加水分解することによって製
造する方法が知られている。しかし、この方法は、原料
を低廉に入手することが困難であるうえに、反応条件が
厳しく、且つ、反応が複雑であって、副生物が多い。し
かも、工程数が多いので、工業的な製造方法としては、
採用し難い。On the other hand, for 4-isopropylcyclohexanone,
Conventionally, for example, J, ^-, Chew, Soc, + g
3646 (1973), J, Am, Che+w,
Soc, +95+ 7599 (1972), tert.
, - Chlorinated with butyl hypochloride to produce l-N,
A known method is to obtain N-cycloaminoapocamphane, react it with aluminum chloride, and hydrolyze it with an acid. However, in this method, it is difficult to obtain raw materials at low cost, the reaction conditions are severe, the reaction is complicated, and there are many by-products. Moreover, since the number of steps is large, as an industrial manufacturing method,
Difficult to hire.
また、特開昭５０−３０８１４号公報には、金触媒の存
在下に気相にて４−イソプロピルシクロヘキサノールを
酸素含有気体に接触させることによって、４−イソプロ
ピルシクロヘキサノンを得る方法が記載されている。し
かし、この方法も、原料を低廉に入手することが容易で
ない。Furthermore, JP-A-50-30814 describes a method for obtaining 4-isopropylcyclohexanone by contacting 4-isopropylcyclohexanol with an oxygen-containing gas in the gas phase in the presence of a gold catalyst. . However, in this method, it is not easy to obtain raw materials at low cost.
ρ−クレゾールについては、■９８９年度触媒研究発表
会要旨集に記載されているように、これをシクロヘキサ
ン中にて水添して、４−メチルシクロヘキサノンを得る
ことが知られている。しかし、上記文献には、４−イソ
プロピルシクロヘキサノンの製造については、何ら検討
がなされていないし、また、本発明者らによれば、４−
イソプロピルフェノールをシクロヘキサン中にて水添し
ても、４−イソプロピルシクロヘキサノンを高転化率及
び高選択率にて得ることができないことを見出している
。As for ρ-cresol, it is known that 4-methylcyclohexanone can be obtained by hydrogenating it in cyclohexane, as described in the 1989 Catalyst Research Presentation Abstracts. However, the above literature does not include any study on the production of 4-isopropylcyclohexanone, and according to the present inventors, 4-isopropylcyclohexanone is not studied at all.
It has been found that even if isopropylphenol is hydrogenated in cyclohexane, 4-isopropylcyclohexanone cannot be obtained with high conversion and high selectivity.
Ｈ（° しよ゛と るｉ
本発明は、従来の４−イソプロピルシクロヘキサノンの
製造における上記した問題を解決するためになされたも
のであって、液相にて穏和な条件下にｐ−イソプロピル
フェノールを接触還元して、高転化率及び高選択率にて
４−イソプロピルシクロヘキサノンを製造する方法を提
供することを目的とする。The present invention was made to solve the above-mentioned problems in the conventional production of 4-isopropylcyclohexanone. An object of the present invention is to provide a method for producing 4-isopropylcyclohexanone at a high conversion rate and high selectivity by catalytic reduction of 4-isopropylcyclohexanone.
量 を ° るための
本発明による４−イソプロピルシクロヘキサノンの製造
方法は、アルキル置換芳香族炭化水素溶剤中、パラジウ
ム触媒の存在下に、ｐ−イソプロピルフェノールを水素
にて還元することを特徴とする。The process for producing 4-isopropylcyclohexanone according to the invention for reducing the amount of 4-isopropylcyclohexanone is characterized in that p-isopropylphenol is reduced with hydrogen in an alkyl-substituted aromatic hydrocarbon solvent in the presence of a palladium catalyst.
本発明においては、触媒として、パラジウム触媒が用い
られる０通常、これらは、シリカ、アルミナ、活性炭、
グラファイト、ケイソウ土、軽石、テトラシリシックマ
イカ、ヘクトライト、テニオライト、モンモリロナイト
等を担体とし、これに担持させて用いられる。このよう
な担持触媒の具体例としては、例えば、パラジウム／活
性炭、パラジウム／シリカ、パラジウム／アル逅す、パ
ラジウム／テトラシリシックマイカ等を挙げることがで
きる。In the present invention, a palladium catalyst is used as a catalyst. Usually, these include silica, alumina, activated carbon,
Graphite, diatomaceous earth, pumice, tetrasilicic mica, hectorite, taeniolite, montmorillonite, etc. are used as carriers, and it is supported on these. Specific examples of such supported catalysts include palladium/activated carbon, palladium/silica, palladium/aluminum, palladium/tetrasilic mica, and the like.
このような担持触媒において、パラジウムの担体への担
持量は、特に、限定されるものではないが、通常、担体
に対して、０．０１〜２０重量％の範囲であり、好まし
くは、０．１〜１０重量％の範囲である。In such a supported catalyst, the amount of palladium supported on the carrier is not particularly limited, but is usually in the range of 0.01 to 20% by weight, preferably 0.01 to 20% by weight, based on the carrier. It ranges from 1 to 10% by weight.
用いる触媒量は、担持触媒として、通常、ｐ −イソプ
ロピルフェノール１００重量部に対して、０．０１〜２
０重量部、好ましくは、０．５〜１０重量部の範囲であ
る。The amount of catalyst used is usually 0.01 to 2 parts by weight per 100 parts by weight of p-isopropylphenol as a supported catalyst.
0 parts by weight, preferably in the range of 0.5 to 10 parts by weight.
本発明による方法において、ｐ−イソプロピルフェノー
ルの還元は、上記触媒の存在下に、アルキル置換芳香族
炭化水素溶剤中にて、水素を用いて行なわれる。上記ア
ルキル置換芳香族炭化水素溶剤としては、例えば、トル
エン、キシレン、メシチレン等や、これらの混合溶剤が
用いられる。In the process according to the invention, the reduction of p-isopropylphenol is carried out using hydrogen in an alkyl-substituted aromatic hydrocarbon solvent in the presence of the catalyst described above. Examples of the alkyl-substituted aromatic hydrocarbon solvent used include toluene, xylene, mesitylene, and mixed solvents thereof.
これら溶剤は、通常、溶剤１ｍｌに対して、ｐ−イソプ
ロピルフェノール量が０．０ Ｏ５〜Ｉｇ、好ましくは
、０６０１〜０．５ ｇとなるように用いられる。These solvents are usually used so that the amount of p-isopropylphenol is 0.0 O5 to Ig, preferably 0601 to 0.5 g, per 1 ml of the solvent.
反応は、通常、常圧又は加圧水素雰囲気下で０〜２００
℃、好ましくは、常温乃至１８０ ’Ｃ程度の温度で行
なわれる。The reaction is usually carried out at normal pressure or under a pressurized hydrogen atmosphere at a temperature of 0 to 200
℃, preferably at a temperature of about room temperature to 180'C.
反応終了後、反応混合物から濾過等の適宜手段にて触媒
を分離した後、抽出、蒸留等の通常の手段によって、目
的物である４−イソプロピルシクロヘキサノンを得るこ
とができる。After the reaction is completed, the catalyst is separated from the reaction mixture by appropriate means such as filtration, and then the target product, 4-isopropylcyclohexanone, can be obtained by conventional means such as extraction and distillation.
屍旦企匁且
以上のように、本発明の方法によれば、溶剤としてアル
キル置換芳香族炭化水素を用いて、ｐ−イソプロビルフ
ェノールを直接に接触還元することによって、高転化率
及び高選択率にて４−イソプロピルシクロヘキサノンを
得ることができ、しかも、原料であるｐ−イソプロピル
フェノールは入手が容易である。従って、本発明の方法
によれば、工業原料として重要な４−イソプロピルシク
ロヘキサノンを低廉に製造することができ、工業上、非
常に有利である。As described above, according to the method of the present invention, p-isopropylphenol is directly catalytically reduced using an alkyl-substituted aromatic hydrocarbon as a solvent, thereby achieving a high conversion rate and high selectivity. 4-isopropylcyclohexanone can be obtained at a high yield, and the raw material p-isopropylphenol is easily available. Therefore, according to the method of the present invention, 4-isopropylcyclohexanone, which is important as an industrial raw material, can be produced at low cost, and is very advantageous industrially.
１嵐明
以下に実施例を挙げて本発明を説明するが、本発明はこ
れら実施例により何ら限定されるものではない。EXAMPLES The present invention will be described below with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例Ｉ
Ｐ−イソプロピルフェノール５．０ｇ、５％パラジウム
／活性炭０．５ｇ及びメシチレン３０ｍ１の混合物を加
熱還流させ、この混合物中に水素を５０ｍ１／分の速度
で３時間吹き込んだ。Example I A mixture of 5.0 g of P-isopropylphenol, 0.5 g of 5% palladium/activated carbon and 30 ml of mesitylene was heated to reflux, and hydrogen was bubbled into the mixture at a rate of 50 ml/min for 3 hours.
反応成績は、ｐ−イソプロピルフェノール転化率８１％
、４−イソプロピルシクロヘキサノン選択率９０％であ
った。The reaction results were p-isopropylphenol conversion rate of 81%.
, 4-isopropylcyclohexanone selectivity was 90%.
実施例２
実施例１において、５％パラジウム／活性炭に代えて、
３％パラジウム／アルミナを用いた以外は、実施例１と
同様に反応を行なった。Example 2 In Example 1, instead of 5% palladium/activated carbon,
The reaction was carried out in the same manner as in Example 1 except that 3% palladium/alumina was used.
反応成績は、ｐ−イソプロピルフェノール転化率７８％
、４−イソプロピルシクロヘキサノン選択率８８％であ
った。The reaction results were p-isopropylphenol conversion rate of 78%.
, 4-isopropylcyclohexanone selectivity was 88%.
実施例３
実施例１において、溶剤として、メシチレンに代えて、
キシレン３０ｍ１を用いた以外は、実施例１と同様に反
応を行なった。Example 3 In Example 1, instead of mesitylene as the solvent,
The reaction was carried out in the same manner as in Example 1 except that 30 ml of xylene was used.
反応成績は、ｐ−イソプロピルフェノール転化率７３％
、４−イソプロピルシクロヘキサノン選択率８５％であ
った。The reaction results were p-isopropylphenol conversion rate of 73%.
, 4-isopropylcyclohexanone selectivity was 85%.
比較例１
実施例１において、溶剤として、メシチレンに代えて、
シクロヘキサン３０ｍ１を用いた以外は、実施例１と同
様に反応を行なった。Comparative Example 1 In Example 1, instead of mesitylene as a solvent,
The reaction was carried out in the same manner as in Example 1, except that 30 ml of cyclohexane was used.
反応成績は、ｐ−イソプロピルフェノール転化率３８％
、４−イソプロピルシクロヘキサノン選択率５５％であ
った。The reaction results were p-isopropylphenol conversion rate of 38%.
, 4-isopropylcyclohexanone selectivity was 55%.
比較例２
実施例１において、ｐ−イソプロピルフェノールに代え
て、ｐ−クレゾール５．０ｇを用いた以外は、実施例１
と同様に反応を行なった。Comparative Example 2 Example 1 except that 5.0 g of p-cresol was used instead of p-isopropylphenol in Example 1.
The reaction was carried out in the same manner.
反応成績は、ｐ−クレゾール転化率５５％、４−メチル
シクロヘキサノン選択率６０％であった。The reaction results were a p-cresol conversion rate of 55% and a 4-methylcyclohexanone selectivity of 60%.
比較例３
実施例１において、溶剤として、メシチレンに代えて、
ベンゼン３０ｍ１を用いた以外は、実施例１と同様に反
応を行なった。Comparative Example 3 In Example 1, instead of mesitylene as a solvent,
The reaction was carried out in the same manner as in Example 1 except that 30 ml of benzene was used.
反応成績は、ｐ−イソプロピルフェノール転化率４０％
、４−イソプロピルシクロヘキサノン選択率６０％であ
った。The reaction results were p-isopropylphenol conversion rate of 40%.
, 4-isopropylcyclohexanone selectivity was 60%.
比較例４
実施例１において、溶剤としてメシチレンに代えて、メ
タノール３０ｎｌを用いた以外は、実施例１と同様に反
応を行なった。Comparative Example 4 The reaction was carried out in the same manner as in Example 1, except that 30 nl of methanol was used instead of mesitylene as the solvent.
反応成績は、ｐ−イソプロピルフェノール転化率１５％
、４−イソプロピルシクロヘキサノン選択率１８％であ
った。The reaction results were p-isopropylphenol conversion rate of 15%.
, 4-isopropylcyclohexanone selectivity was 18%.
比較例５
実施例１において、５％パラジウム／活性炭に代えて、
酸化白金（ｐｔｏ□）０．３ｇを用いた以外は、実施例
１と同様に反応を行なった。Comparative Example 5 In Example 1, instead of 5% palladium/activated carbon,
The reaction was carried out in the same manner as in Example 1, except that 0.3 g of platinum oxide (pto□) was used.
反応成績は、Ｐ−イソプロピルフェノール転化率６４％
、４−イソプロピルシクロヘキサノン選択率２８％であ
った。The reaction results were P-isopropylphenol conversion rate of 64%.
, 4-isopropylcyclohexanone selectivity was 28%.
尚、この反応においては、４−イソプルピルシクロヘキ
サノンが更に還元されたｐ−イソプロピルシクロヘキサ
ノールが選択率５２％にて生成していることが認められ
た。In this reaction, it was observed that p-isopropylcyclohexanol, which was further reduced from 4-isopropylcyclohexanone, was produced at a selectivity of 52%.
比較例６
実施例１において、５％パラジウム／活性炭に代えて、
２％イリジウム／シリカ０．３ｇを用いた以外は、実施
例１と同様に反応を行なった。Comparative Example 6 In Example 1, instead of 5% palladium/activated carbon,
The reaction was carried out in the same manner as in Example 1, except that 0.3 g of 2% iridium/silica was used.
反応成績は、Ｐ−イソプロピルフェノール転化率５８％
、４−イソプロピルシクロヘキサノン選択率２１％であ
った。The reaction results were P-isopropylphenol conversion rate of 58%.
, 4-isopropylcyclohexanone selectivity was 21%.
尚、この反応においては、４−イソプロピルシクロヘキ
サノンが更に還元されたｐ−イソプロピルシクロヘキサ
ノールが選択率６４％にて生成していることが認められ
た。In this reaction, it was observed that p-isopropylcyclohexanol, in which 4-isopropylcyclohexanone was further reduced, was produced at a selectivity of 64%.
Claims (1)
触媒の存在下に、ｐ−イソプロピルフェノールを水素に
て還元することを特徴とする４−イソプロピルシクロヘ
キサノンの製造方法。(1) A method for producing 4-isopropylcyclohexanone, which comprises reducing p-isopropylphenol with hydrogen in the presence of a palladium catalyst in an alkyl-substituted aromatic hydrocarbon solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1320126A JPH03181438A (en) | 1989-12-08 | 1989-12-08 | Production of 4-isopropylcyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1320126A JPH03181438A (en) | 1989-12-08 | 1989-12-08 | Production of 4-isopropylcyclohexanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03181438A true JPH03181438A (en) | 1991-08-07 |
Family
ID=18117992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1320126A Pending JPH03181438A (en) | 1989-12-08 | 1989-12-08 | Production of 4-isopropylcyclohexanone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03181438A (en) |
-
1989
- 1989-12-08 JP JP1320126A patent/JPH03181438A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5354886A (en) | Catalysts on inorganic carriers for producing ethylidene diacetate | |
| JP4121647B2 (en) | Method for producing alcohol | |
| JPS646183B2 (en) | ||
| US4334107A (en) | Catalytic purification of phenol | |
| JP2523753B2 (en) | Method for producing 2,3-dichloropyridine | |
| US4250118A (en) | Process for the preparation of cyclohexanone | |
| JPH03181438A (en) | Production of 4-isopropylcyclohexanone | |
| JP4312334B2 (en) | Indan manufacturing method | |
| JPH0374651B2 (en) | ||
| JP2002539083A (en) | Method for producing cyclohexanecarboxylic acid using [2 + 4] Diels-Alder reaction | |
| JP2001206860A (en) | Method for producing fluorenes | |
| JPH04149160A (en) | Production of 1-amino-4-alkoxybenzene compounds | |
| JP3994248B2 (en) | Production method of cyclododecanone | |
| JP3795974B2 (en) | Process for producing α, β-cyclic unsaturated ether | |
| JPH03202152A (en) | Hydrogenating catalyst | |
| JP2739504B2 (en) | Method for producing cyclohexane-1,4-dione | |
| JPS61251659A (en) | Production of 2-or 3-aminomethylpiperidine | |
| JP2643375B2 (en) | Method for producing phenylhydroquinones | |
| JPH0597778A (en) | Production of 2-aminoindane and its salts | |
| JPS643862B2 (en) | ||
| JP2001302570A (en) | Method for producing cyclododecanone and cyclododecanol | |
| JP2996713B2 (en) | Process for producing 2,3-cyclohexenopyridine | |
| JPS6322036A (en) | Selective preparation of perhydroacenaphthene trans isomer | |
| JPS63297363A (en) | Production of 3-methylindoles | |
| JPH023653A (en) | Production of benzonitriles |