JPH01242539A - Production of aromatic alcohols - Google Patents
Production of aromatic alcoholsInfo
- Publication number
- JPH01242539A JPH01242539A JP6791188A JP6791188A JPH01242539A JP H01242539 A JPH01242539 A JP H01242539A JP 6791188 A JP6791188 A JP 6791188A JP 6791188 A JP6791188 A JP 6791188A JP H01242539 A JPH01242539 A JP H01242539A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- aromatic
- hydrogen reduction
- catalyst
- hydroperoxides
- 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
- -1 aromatic alcohols Chemical class 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 238000006722 reduction reaction Methods 0.000 claims description 27
- 239000002904 solvent Substances 0.000 abstract description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052759 nickel Inorganic materials 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 239000000377 silicon dioxide Substances 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 8
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- XIBAZLLABMNRRJ-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=C(C(C)C)C=C1 XIBAZLLABMNRRJ-UHFFFAOYSA-N 0.000 description 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QBEZHXMLBPSPCU-UHFFFAOYSA-N hydrogen peroxide;1-propan-2-ylnaphthalene Chemical compound OO.C1=CC=C2C(C(C)C)=CC=CC2=C1 QBEZHXMLBPSPCU-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（ｉ）発明の目的
〔産業上の利用分野］
本発明は芳香族アルコール類の製造方法に関するもので
ある。詳しくは本発明は芳香族ハイドロパーオキサイド
類を水素還元触媒の存在下に液相〔従来の技術〕
芳香族アルコール類は、各種有機薬品の中間体、溶剤と
して有用であり、工業的には芳香族ハイドロパーオキサ
イド類の還元によって製造するのが有利である。特公昭
３９−２６９６１号公報には、クメンに溶解したクメン
ハイドロパーオキサイド又はジクミルパーオキサイドを
Ｉ’ｄ、 Ｎｉ等の水素添加触媒の存在下水素により還
元してα−クミルアルコールを製造する方法が提案され
ている。この反応は発熱を伴なうので反応を円滑に進め
副反応を出来るだけ防止するために溶媒の使用が推奨さ
れて性の溶媒が使用されている。しかしながら、前記溶
媒を使用する系においては触媒活性低下が意外に早く起
るとして、溶媒として低級脂肪族アルコールを使用する
方法が特開昭５５−６９５２７号で提案されている。ま
た、芳香族アルコールを高収率で製造するため該還元反
応をアミン類或いは該水素還元反応中にアミン類に変化
し得る化合物の共存下に行なう方法が特開昭６０−１７
４７３７号公報に提案されている。Detailed Description of the Invention (i) Object of the Invention [Field of Industrial Application] The present invention relates to a method for producing aromatic alcohols. More specifically, the present invention is directed to preparing aromatic hydroperoxides in a liquid phase in the presence of a hydrogen reduction catalyst [Prior art] Aromatic alcohols are useful as intermediates and solvents for various organic chemicals, and are industrially used as aromatic Preferably, they are prepared by reduction of group hydroperoxides. Japanese Patent Publication No. 39-26961 discloses that α-cumyl alcohol is produced by reducing cumene hydroperoxide or dicumyl peroxide dissolved in cumene with hydrogen in the presence of a hydrogenation catalyst such as I'd or Ni. A method is proposed. Since this reaction is accompanied by heat generation, the use of a solvent is recommended in order to advance the reaction smoothly and prevent side reactions as much as possible, and a sterile solvent is used. However, in systems using the above-mentioned solvents, catalyst activity decreases unexpectedly quickly, and a method using a lower aliphatic alcohol as a solvent has been proposed in JP-A-55-69527. In addition, in order to produce aromatic alcohols in high yield, a method in which the reduction reaction is carried out in the coexistence of amines or compounds that can be converted into amines during the hydrogen reduction reaction is disclosed in JP-A-60-17.
This is proposed in Publication No. 4737.
しかしながら、前記公報に記載された水素還元方法では
、製造となる芳香族アルコールと性質の異なる脂肪族ア
ルコールやアミン類等との繁雑な分＾１１工程が必要で
あるので、かかる方法は芳香族ハイドロパーオキサイド
を水素還元して芳香族アルコールを製造することが出来
ても工業的に有利に実施できる方法ではないという問題
点がある。However, the hydrogen reduction method described in the above-mentioned publication requires 11 complicated steps in which the aromatic alcohol to be produced is mixed with aliphatic alcohols, amines, etc. having different properties. Even if aromatic alcohols can be produced by hydrogen reduction of peroxides, there is a problem in that it is not an industrially advantageous process.
（ｉｉ ）発明の構成
〔問題点を解決するための手段〕
本発明者等は、前記の問題点を解決するために、更に鋭
意検討を重ねた結果、芳香族ハイドロパーオキサイド類
を水素還元触媒の存在下に液相で水素還元する際に反応
系に供給する芳香族ハイドロパーオキサイド類の濃度を
４％以下にして水素還元反応を行なうことにより高い活
性が安定して得られることを見出し本発明を完成するに
至った。(ii) Structure of the Invention [Means for Solving the Problems] In order to solve the problems mentioned above, the present inventors have conducted further intensive studies and found that aromatic hydroperoxides can be used as hydrogen reduction catalysts. We discovered that high activity can be stably obtained by reducing the concentration of aromatic hydroperoxides supplied to the reaction system to 4% or less during hydrogen reduction in the liquid phase in the presence of hydrogen. The invention was completed.
即ち、本発明の芳香族アルコール類の製造方法は、芳香
族ハイドロパーオキサイド類を水素還元触媒の存在下に
液相で水素還元する際に反応系に供給する芳香族ハイド
ロパーオキサイド類の濃度を４％以下にして水素還元反
応を行なうことを特徴とする芳香族アルコールの製造方
法である。That is, in the method for producing aromatic alcohols of the present invention, when aromatic hydroperoxides are hydrogen-reduced in the liquid phase in the presence of a hydrogen reduction catalyst, the concentration of aromatic hydroperoxides supplied to the reaction system is controlled. This is a method for producing an aromatic alcohol characterized by carrying out a hydrogen reduction reaction at a concentration of 4% or less.
本発明の水素還元反応の対象となる芳香族ハイドロパー
オキサイド類とは、例えば、α−フェニルエヂルハイド
ロバーオキサイド、キュメンハイドロパーオキサイド、
シメンハイドロパーオキサイド、ｍ−またはｐ−ジイソ
プロピルベンゼンモノハイドロバーオキサイド、ｍ−ま
たはρ−ジイソブロビルベンゼンジハイドロバーオキサ
イド、イソプロピルナフタレンハイドロパーオキサイド
などや、これらの少なくとも１種を含有する組成物をい
う。The aromatic hydroperoxides to be subjected to the hydrogen reduction reaction of the present invention include, for example, α-phenylethyl hydroperoxide, cumene hydroperoxide,
Cymene hydroperoxide, m- or p-diisopropylbenzene monohydroperoxide, m- or ρ-diisobrobylbenzene dihydroperoxide, isopropylnaphthalene hydroperoxide, etc., or a composition containing at least one of these. say.
水素
本発明における水素還元反応系への水素の供給〒は、目
的の芳香族ハイドロパーオキサイド類の水素還元反応に
必要な水素量の１〜５０倍、好ましくは１〜３０倍、最
も好ましくは１〜２０倍程度である。供給する水素量が
多すぎるのはロスとなり水素の回収系・循環系などの付
属設備が膨大となったり、不必要な副反応が起こる場合
もある。Hydrogen The amount of hydrogen supplied to the hydrogen reduction reaction system in the present invention is 1 to 50 times, preferably 1 to 30 times, and most preferably 1 to 30 times the amount of hydrogen required for the hydrogen reduction reaction of the target aromatic hydroperoxide. ~20 times. If too much hydrogen is supplied, there will be a loss, which will require an enormous amount of attached equipment such as a hydrogen recovery system and circulation system, and unnecessary side reactions may occur.
氷１１且慕媒
本発明の芳香族アルコール類の製造方法で使用する水素
還元触媒は芳香族ハイドロパーオキサイド類の水素還元
触媒能を有するものであれば良く、例えばＰｄ、 Ｒｕ
等の白金族金属やＮｉ等を触媒成分として含有する触媒
である。この種の水素還元触媒は、通常その触媒成分が
適当な担体に担持されており、担体としては耐熱性の無
機化合物担体、例えばアルミナ、シリカ、などの合成ゲ
ル担体、或いはケイソウ土、多孔性粘土などの天然無機
物担体等が挙げられる。Ice 11 and Enriching medium The hydrogen reduction catalyst used in the method for producing aromatic alcohols of the present invention may be any catalyst as long as it has the ability to catalyze hydrogen reduction of aromatic hydroperoxides, such as Pd, Ru, etc.
This is a catalyst containing platinum group metals such as Ni, Ni, etc. as catalyst components. In this type of hydrogen reduction catalyst, the catalyst components are usually supported on a suitable carrier, and the carrier is a heat-resistant inorganic compound carrier, such as a synthetic gel carrier such as alumina or silica, or diatomaceous earth or porous clay. Examples include natural inorganic carriers such as .
反応應且
本発明の芳香族アルコール類の製造方法における反応態
様としては、特開昭５４−７３７０９号公報にも示され
ている通り、有機過酸化物の水素還元方法として公知な
回分式、連続式その他任意のｌ様で実施することができ
る。触媒を懸濁床とすると触媒の分離工程が必要となる
ので、固定床の方が好ましい。As for the reaction mode in the method for producing aromatic alcohols of the present invention, as disclosed in JP-A No. 54-73709, the known method for hydrogen reduction of organic peroxides is a batch method or a continuous method. It can be implemented using any other formula. If the catalyst is a suspended bed, a catalyst separation step is required, so a fixed bed is preferable.
産媛
本発明の芳香族アルコール類の製造方法における芳香族
ハイドロパーオキサイド類を希釈する溶媒としては、芳
香族ハイドロパーオキサイド類および製品である芳香族
アルコール類を溶かすものなら良（、脂肪族炭化水素類
、芳香族炭化水素類や芳香族アルコール類などが挙げら
れる。例えばキュメンハイドロパーオキサイドの場合は
キュメンハイドロパーオキサイドの製造工程でキュメン
が溶媒として存在しており、そのままキュメンを溶媒と
して使用できるし、また、キュメンハイドロパーオキサ
イドを水素還元して得られる製品のクミルアルコールを
循環させて溶媒とするのも良い方法である。Sanhime: In the method for producing aromatic alcohols of the present invention, the solvent for diluting the aromatic hydroperoxides may be any solvent that dissolves the aromatic hydroperoxides and the aromatic alcohol product. Examples include hydrogens, aromatic hydrocarbons, and aromatic alcohols.For example, in the case of cumene hydroperoxide, cumene is present as a solvent in the manufacturing process of cumene hydroperoxide, and cumene can be used as it is as a solvent. However, it is also a good method to circulate cumyl alcohol, which is a product obtained by hydrogen reduction of cumene hydroperoxide, and use it as a solvent.
一＝１ハイドロパーオキサイド の２
本発明の芳香族アルコール類の製造方法における水素還
元反応では反応器に供給される原料液中の芳香族ハイド
ロパーオキサイド類の濃度を４％以下、好ましくは０．
０１％以上４％以下、最も好反応温度が安定しない、高
い活性が得られない、副反応が起こり易くなるなどの問
題が生ずる。1 = 1 hydroperoxide In the hydrogen reduction reaction in the method for producing aromatic alcohols of the present invention, the concentration of aromatic hydroperoxides in the raw material liquid supplied to the reactor is 4% or less, preferably 0.
If the amount is 01% or more and 4% or less, problems arise such as the most favorable reaction temperature is not stable, high activity cannot be obtained, and side reactions are likely to occur.
反応１度
本発明の芳香族アルコール類の製造方法における水素還
元反応は、通常０〜１５０°Ｃ１好ましくは１０〜１２
０ ’Ｃの範囲で行なわれる。反応温度が高すぎると芳
香族ハイドロパーオキサイド類自身の分解反応などの副
反応が激しくなるので好ましくない。また、反応温度が
低すぎると反応速度が遅くなるなどの問題が生ずる。The hydrogen reduction reaction in the method for producing aromatic alcohols of the present invention is carried out at a temperature of usually 0 to 150°C, preferably 10 to 12°C.
This is done in the range of 0'C. If the reaction temperature is too high, side reactions such as decomposition reactions of the aromatic hydroperoxides themselves become intense, which is not preferable. Furthermore, if the reaction temperature is too low, problems such as a slow reaction rate will occur.
反血圧方
本発明の芳香族アルコール類の製造方法における水素還
元反応の全圧は、通常、常圧〜加圧下、好ましくは常圧
〜５０ ｋｇ／ｃｆｌＹＧ 、最も好ましくは常圧〜３
０ ｋｇ／ｃ＋ＮＧである。芳香族ハイドロパーオキサ
イド類の水素還元反応は容易に進行するので、反応圧力
を必要以上に高くしても装置の建設費が大となるのみで
無駄であるし、生成液や溶媒の逐次的な水素還元反応が
起きるなどの問題が生ずる。The total pressure of the hydrogen reduction reaction in the method for producing aromatic alcohols of the present invention is usually normal pressure to elevated pressure, preferably normal pressure to 50 kg/cflYG, and most preferably normal pressure to 3 kg/cflYG.
0 kg/c+NG. The hydrogen reduction reaction of aromatic hydroperoxides proceeds easily, so increasing the reaction pressure more than necessary will only increase the construction cost of the equipment and is wasteful, and Problems such as hydrogen reduction reactions occur.
［実施例等］
以下に触媒製造例、実施例、比較例を挙げて、更に詳述
する。これらの例に記・代の％は特に記載しない限り重
量基準による。[Examples, etc.] The following is a further detailed description of catalyst production examples, examples, and comparative examples. The percentages in these examples are based on weight unless otherwise specified.
触媒製造例
３ ｍｍφ×３胴の円柱型に成形したγ−アルミナに、
濃度０．６重量％の塩化パラジウム水溶液を含浸させ、
１１０°Ｃで１昼夜乾燥させた。Catalyst production example 3 γ-alumina molded into a cylindrical shape of mmφ x 3 cylinders,
Impregnated with palladium chloride aqueous solution with a concentration of 0.6% by weight,
It was dried at 110°C for one day and night.
次いで、その乾燥物を水素気流下で４００°Ｃの温度で
１６時時間光処理して、組成がＰｄ（０，３％）／Ｔ−
八１２０３の水素還元触媒を得た。Next, the dried product was phototreated at a temperature of 400°C for 16 hours under a hydrogen stream to change the composition to Pd(0.3%)/T-
A hydrogen reduction catalyst of 81203 was obtained.
したガコ型攪拌機、原料供給管、水素供給管、生成液抜
出し管を備えた内容積２００ ｍｌのステンレス製オー
トクレーブを６０°Ｃに保ちながら２．６％キュメンハ
イドロパーオキサイド（以下ＣＩＩＰと略することがあ
る）・キュメン溶液を１．２１．／時、水素を８２／時
の速度で連続的に供給し、オートクレーブの内容物が８
０−となるように調整した生成液抜出し管から水素還元
生成液を連続的に抜き出した。この時の水素圧力は７．
５ ｋｇ／ｃＩＩＮ−Ｇ、 ａ拌機の回転数は７５０
ｒｐｍに保った。ＣＨＰ ・キュメン溶液供給後８時
間目のＣＩＩＰ水素還元反応速度を第１表に示す。2.6% cumene hydroperoxide (hereinafter abbreviated as CIIP) was kept at 60°C in a stainless steel autoclave with an internal volume of 200 ml equipped with a gas-type stirrer, a raw material supply pipe, a hydrogen supply pipe, and a product liquid extraction pipe. )・cumene solution 1.21. /hour, hydrogen was continuously supplied at a rate of 82/hour, and the contents of the autoclave reached 82/hour.
The hydrogen-reduced product liquid was continuously extracted from the product liquid extraction tube which was adjusted to be 0-. The hydrogen pressure at this time is 7.
5 kg/cIIN-G, a stirrer rotation speed is 750
kept at rpm. Table 1 shows the CIIP hydrogen reduction reaction rate 8 hours after supplying the CHP/cumene solution.
実施例−２
ＣＩＩＰの濃度を２．６％、水素の供給量を９１７時と
したこと以外は実施例−１と同様の操作を行ない第１表
に示す結果を得た。Example 2 The same operation as in Example 1 was performed except that the concentration of CIIP was 2.6% and the amount of hydrogen supplied was 917 hours, and the results shown in Table 1 were obtained.
比較例−１
ＣＩ＋１’の濃度を７．９％、水素の供給量１９１／時
としたこと以外は実施例−１と同様の操作を行ない第１
表に示す結果を得た。Comparative Example-1 The same operation as Example-1 was carried out except that the concentration of CI+1' was 7.9% and the hydrogen supply rate was 191/hour.
The results shown in the table were obtained.
第 １ 表
実施例−３
外径６ ｍｍの温度計保護管を備えた内径３０ｍｍのス
テンレス製反応管に実施例−１と同一の触媒を５００ｄ
充填した。触媒層の入口温度が４５°Ｃとなるように調
整し、３．５％ＣＩＩＰ・キュメン溶液を２０１７時、
水素を２０１／時の速度で連続的に ２供給した。反応
圧力は７．５ ｋｇ／ ｃｎｌ−Ｇで行なった。Table 1 Example-3 500 d of the same catalyst as in Example-1 was placed in a stainless steel reaction tube with an inner diameter of 30 mm and equipped with a thermometer protection tube with an outer diameter of 6 mm.
Filled. The inlet temperature of the catalyst layer was adjusted to 45 °C, and a 3.5% CIIP/cumene solution was added at 2017.
Hydrogen was continuously fed 2 times at a rate of 201/hour. The reaction pressure was 7.5 kg/cnl-G.
キュメン溶液供給後８時間目のＣＩＩＰ転化率は９９．
９％、クミルアルコールの収率は９９％であった。The CIIP conversion rate 8 hours after supplying the cumene solution was 99.
The yield of cumyl alcohol was 99%.
比較例−２
ＣＩＩＰの濃度を８．０％、水素の供給量を４５１／時
としたこと以外は実施例−３と同様の操作を行なったが
、発熱が激しく安定した運転は不可能であった。また、
キュメン溶液供給後８時間目のＣＩＩＰ転化率は９９．
６％であったが、クミルアルコールの収率は９５％と低
く、アセトフェノン、α−メチルスチレン、■−フェニ
ルエタノール等の副生が認められた。Comparative Example 2 The same operation as in Example 3 was carried out except that the concentration of CIIP was 8.0% and the amount of hydrogen supplied was 451/hour, but stable operation was impossible due to excessive heat generation. Ta. Also,
The CIIP conversion rate 8 hours after supplying the cumene solution was 99.
However, the yield of cumyl alcohol was as low as 95%, and by-products such as acetophenone, α-methylstyrene, and ■-phenylethanol were observed.
本発明の製造方法によれば、芳香族ハイドロパーオキサ
イド類を高い転化率で安定して水素還元することができ
、しかも高い選択率で対応する芳香族アルコール類を製
造することができる。According to the production method of the present invention, aromatic hydroperoxides can be stably reduced with hydrogen at a high conversion rate, and the corresponding aromatic alcohols can be produced with a high selectivity.
Claims (1)
存在下に液相で水素還元して芳香族アルコール類を製造
する際に、反応系に供給する芳香族ハイドロパーオキサ
イド類の濃度を４％以下にして水素還元反応を行なうこ
とを特徴とする芳香族アルコール類の製造方法。1. When producing aromatic alcohols by reducing aromatic hydroperoxides with hydrogen in the liquid phase in the presence of a hydrogen reduction catalyst, the concentration of aromatic hydroperoxides supplied to the reaction system should be 4% or less. A method for producing aromatic alcohols, which comprises carrying out a hydrogen reduction reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63067911A JP2512067B2 (en) | 1988-03-22 | 1988-03-22 | Manufacturing method of cumyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63067911A JP2512067B2 (en) | 1988-03-22 | 1988-03-22 | Manufacturing method of cumyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01242539A true JPH01242539A (en) | 1989-09-27 |
| JP2512067B2 JP2512067B2 (en) | 1996-07-03 |
Family
ID=13358563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63067911A Expired - Fee Related JP2512067B2 (en) | 1988-03-22 | 1988-03-22 | Manufacturing method of cumyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2512067B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051541C (en) * | 1993-03-31 | 2000-04-19 | 兰州大学 | Prepn. method for 2-phenyl-2-propanol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS495324A (en) * | 1972-04-29 | 1974-01-18 | ||
| JPS61130249A (en) * | 1984-11-30 | 1986-06-18 | Sumitomo Chem Co Ltd | Production of aromatic alcohol |
-
1988
- 1988-03-22 JP JP63067911A patent/JP2512067B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS495324A (en) * | 1972-04-29 | 1974-01-18 | ||
| JPS61130249A (en) * | 1984-11-30 | 1986-06-18 | Sumitomo Chem Co Ltd | Production of aromatic alcohol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051541C (en) * | 1993-03-31 | 2000-04-19 | 兰州大学 | Prepn. method for 2-phenyl-2-propanol |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2512067B2 (en) | 1996-07-03 |
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