JPH0449261A - Production of 2-alkoxycyclohexanol - Google Patents
Production of 2-alkoxycyclohexanolInfo
- Publication number
- JPH0449261A JPH0449261A JP2159381A JP15938190A JPH0449261A JP H0449261 A JPH0449261 A JP H0449261A JP 2159381 A JP2159381 A JP 2159381A JP 15938190 A JP15938190 A JP 15938190A JP H0449261 A JPH0449261 A JP H0449261A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexene oxide
- alcohol
- catalyst
- reaction
- inorganic solid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims abstract description 30
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 229910003480 inorganic solid Inorganic materials 0.000 claims abstract description 14
- 239000011973 solid acid Substances 0.000 claims abstract description 14
- 229910021536 Zeolite Inorganic materials 0.000 claims description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 7
- 239000010457 zeolite Substances 0.000 claims description 7
- 238000000746 purification Methods 0.000 abstract description 8
- 238000005260 corrosion Methods 0.000 abstract description 6
- 230000007797 corrosion Effects 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 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 abstract 1
- 229910052901 montmorillonite Inorganic materials 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- -1 alkoxy alcohols Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- PKOQGLKMAXRWPD-UHFFFAOYSA-N 2-ethoxycyclohexan-1-ol Chemical compound CCOC1CCCCC1O PKOQGLKMAXRWPD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003826 tablet Substances 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)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、医・農薬中間原料として重要な２アルコキシ
シクロヘキサノールをシクロヘキセンオキシドとアルコ
ールとにより効率よく製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for efficiently producing 2-alkoxycyclohexanol, which is important as an intermediate raw material for medicines and agricultural chemicals, from cyclohexene oxide and alcohol.
（従来の技術）
分枝状ないしは脂環式のエポキシドのアルコールとの反
応によるアルコキシアルコールの製造方法は一般的に良
く知られており、−船釣には酸やアルカリの添加により
促進される。PRIOR ART The process for producing alkoxy alcohols by reaction of branched or cycloaliphatic epoxides with alcohols is generally well known and is facilitated in boat fishing by the addition of acids or alkalis.
（発明が解決しようとする課題）
以上のように、エポキシドとアルコールとの反応により
相当するアルコキシアルコールを製造する方法は公知で
ある。(Problems to be Solved by the Invention) As described above, a method for producing a corresponding alkoxy alcohol by reacting an epoxide with an alcohol is known.
触媒として、硫酸のような鉱酸を用いた場合、まず装置
の腐食防止および作業者に対する安全性などを考慮せね
ばならない。When using a mineral acid such as sulfuric acid as a catalyst, first consideration must be given to corrosion prevention of equipment and safety to workers.
また、反応粗液から製品であるアルコキシアルコールを
精製する際、酸を中和すると塩が析出して配管や装置に
付着する等の問題が生じる。Further, when the product alkoxy alcohol is purified from the reaction crude liquid, neutralizing the acid causes problems such as salt precipitation and adhesion to piping and equipment.
また、酢酸のような有機酸を用いた場合も、装置の腐食
やアルコキシアルコール精製時に酸を中和しない場合は
蒸留分離する必要が生じる。Furthermore, even when an organic acid such as acetic acid is used, distillation separation may be necessary if equipment is corroded or the acid is not neutralized during alkoxy alcohol purification.
このような問題を解決するために、本発明者は鋭意検討
した結果、装置の腐食やアルコキシアルコール精製時の
問題を引き起こさない触媒として、無機固体酸を使用す
ることが最も好ましいことを見い出した。In order to solve such problems, the inventors of the present invention have conducted intensive studies and found that it is most preferable to use an inorganic solid acid as a catalyst that does not cause corrosion of equipment or problems during alkoxy alcohol purification.
（発明の目的）
本発明の目的は、装置の腐食やジオール精製時の問題を
引き起こさずに、シクロヘキセンオキシドとアルコール
とを反応させてアルコキシアルコールを高活性で製造す
る方法を提供することにある。(Objective of the Invention) An object of the present invention is to provide a method for producing alkoxy alcohol with high activity by reacting cyclohexene oxide and alcohol without causing corrosion of equipment or problems during diol purification.
（課題を解決するための手段）
すなわち、本発明は、
「シクロヘキセンオキシドとアルコールとを反応させて
２−アルコキシシクロヘキサノールを製造する方法にお
いて、無機固体酸触媒の存在下で反応させることを特徴
とする２−アルコキシシクロヘキサノールの製造方法」
である。(Means for Solving the Problems) That is, the present invention provides a method for producing 2-alkoxycyclohexanol by reacting cyclohexene oxide and alcohol, characterized in that the reaction is carried out in the presence of an inorganic solid acid catalyst. A method for producing 2-alkoxycyclohexanol.
本発明において、触媒として使用される無機固体酸触媒
としては、シリカ、アルミナ、シリカ−アルミナ、ゼオ
ライト、チタニア、ジルコニア、固体リン酸類、あるい
はこれらの組成物としての複合体、または担持物と担体
との関係を含む複合体等が用いられ、なかでもゼオライ
トが好ましい。In the present invention, the inorganic solid acid catalyst used as a catalyst includes silica, alumina, silica-alumina, zeolite, titania, zirconia, solid phosphoric acids, a composite of these as a composition, or a support and a support. Composites containing the following relationships are used, and among them, zeolite is preferred.
また、無機固体酸を用いた場合、鉱酸や有機酸使用時の
ような装置の腐食や２−アルコキシシクロヘキサノール
精製時の問題が起こらず、触媒の回収再使用が極めて容
易となるため、本発明の方法の工業的な意義は非常に大
きいものである。In addition, when inorganic solid acids are used, equipment corrosion and 2-alkoxycyclohexanol purification problems that occur when mineral acids or organic acids are used do not occur, and the catalyst can be recovered and reused extremely easily. The industrial significance of the method of the invention is very large.
本発明に用いる無機固体酸の濃度としては、特に制限は
ないが、好ましくは出発原料に対して０゜０１〜１０重
量％の範囲で用いられる。The concentration of the inorganic solid acid used in the present invention is not particularly limited, but it is preferably used in a range of 0.01 to 10% by weight based on the starting material.
用いられる無機固体酸はペレット状、粉末状、タブレッ
ト状など形状に制限はないが、回収のし易さのことを考
慮するとペレット状のものなどが好ましい。The shape of the inorganic solid acid used is not limited to pellets, powder, tablets, etc., but pellets are preferable in consideration of ease of recovery.
本発明を実施する場合、シクロヘキセンオキシドに対し
てアルコールの使用量は理論量以上にする必要がある。When carrying out the present invention, it is necessary to use more than the theoretical amount of alcohol relative to cyclohexene oxide.
シクロヘキセンオキシドに対してアルコールの使用量が
理論量以下の場合は、生成した１、２−シクロヘキサン
ジオールと未反応のシクロヘキセンオキシドとが容易に
反応して目的としない物が生成するため収率が低下した
り、触媒の活性低下が激しくなる。If the amount of alcohol used is less than the theoretical amount relative to cyclohexene oxide, the yield will decrease because the generated 1,2-cyclohexanediol and unreacted cyclohexene oxide will easily react and produce unintended products. or the catalyst activity decreases drastically.
理論量以上であれば特に制限はないが２〜１００モル倍
の範囲が適当である。There is no particular restriction as long as it is more than the theoretical amount, but a range of 2 to 100 moles is appropriate.
アルコールのモル倍率が小さいと理論量以上であっても
副反応が起き収率が低下するのでアルコールの下限量は
、収率低下の割合と精製コストから決めるべきである。If the molar ratio of alcohol is small, side reactions will occur even if the amount exceeds the theoretical amount, resulting in a decrease in yield, so the lower limit of alcohol should be determined based on the rate of decrease in yield and purification cost.
アルコールのモル倍率が大きい場合は収率は向上するが
精製コストが増大し、反応器も大きくなるなどの不利な
ことが起きるので得策ではない。If the molar ratio of alcohol is large, the yield will improve, but the purification cost will increase and the size of the reactor will also increase, which is not a good idea.
本発明に用い得るアルコールとしてはメタノール、エタ
ノール、プロパンオール、シクロヘキサノール、など飽
和脂肪族アルコール、アリルアルコール、クロチルアル
コールなど不飽和脂肪族アルコール、ベンジアルコール
、フェノールなどの芳香族アルコール、エチレングリコ
ール、プロピレングリコールなどの２価のアルコール、
グリセリンなどの３価のアルコールが挙げられる。Examples of alcohols that can be used in the present invention include saturated aliphatic alcohols such as methanol, ethanol, propanol, and cyclohexanol, unsaturated aliphatic alcohols such as allyl alcohol and crotyl alcohol, aromatic alcohols such as benzyl alcohol and phenol, ethylene glycol, dihydric alcohols such as propylene glycol,
Examples include trihydric alcohols such as glycerin.
本発明を実施する場合、反応温度は特に制限ないが、工
業的に実施していく場合の設備費などを考慮すると、常
圧下で沸点以下の温度が好ましい。When carrying out the present invention, the reaction temperature is not particularly limited, but in consideration of equipment costs for industrial implementation, a temperature below the boiling point under normal pressure is preferred.
また、反応温度があまり低いと反応速度が遅くなり、好
ましくない。Furthermore, if the reaction temperature is too low, the reaction rate will be slow, which is not preferable.
好ましくは、常圧下で室温以上、沸点以下の温度条件を
選定する。Preferably, the temperature conditions are selected to be at least room temperature and at most the boiling point under normal pressure.
本発明を実施する場合、反応時間は反応温度や原料組成
によって異なるが、通常は数分から数時間の範囲から選
択すれば良い。When carrying out the present invention, the reaction time may vary depending on the reaction temperature and raw material composition, but is usually selected from a range of several minutes to several hours.
反応を行う場合、原料の仕込み順序は工夫した方か良い
、具体的には以下のように行う。When carrying out the reaction, it is better to devise the order in which the raw materials are added. Specifically, it is carried out as follows.
すなわち、通常回分方式で行なう場合、固体触媒を反応
器中に仕込まれたアルコールの中に分散させておき、ま
ず温度を上記の範囲内になるように調整する。That is, when carrying out in a normal batch method, a solid catalyst is dispersed in alcohol charged in a reactor, and the temperature is first adjusted to be within the above range.
所定の温度に到達した時点てシクロヘキセンオキシドを
液中に所定の速度で供給する。When a predetermined temperature is reached, cyclohexene oxide is fed into the liquid at a predetermined rate.
シクロヘキセンオキシドを仕込んだ反応器中にアルコー
ルを仕込む順序にすると生成した１、２シクロヘキサン
ジオールと未反応のシクロヘキセンオキシドとが容易に
反応して目的としない物が生成するため収率が低下する
ためである。This is because if the alcohol is charged into the reactor containing cyclohexene oxide, the produced 1,2-cyclohexanediol and unreacted cyclohexene oxide will easily react, producing unintended products, resulting in a lower yield. be.
本発明は工業的に実施する場合、回分方式で行ってもよ
いし、連続方式で行ってもよい。When the present invention is carried out industrially, it may be carried out either batchwise or continuously.
いずれの方式でも無機固体酸は回収され、再使用される
。In either method, the inorganic solid acid is recovered and reused.
無機固体酸の回収は沈澱、濾過、遠心分離など通常おこ
なわれる方法が適用できる。Conventional methods such as precipitation, filtration, and centrifugation can be used to recover the inorganic solid acid.
（発明の効果）
本発明によると、シクロヘキセンオキシドとシクロヘキ
センオキシドに対して過剰量のアルコールとを、無機固
体酸触媒の存在下液相条件下に反応させることで、装置
腐食のない、触媒分離の簡単な極めて工業的に有利なシ
クロヘキセンオキシドから２−アルコキシシクロヘキサ
ノールを製造するものである。(Effects of the Invention) According to the present invention, by reacting cyclohexene oxide with an excess amount of alcohol relative to the cyclohexene oxide under liquid phase conditions in the presence of an inorganic solid acid catalyst, catalyst separation can be achieved without equipment corrosion. 2-alkoxycyclohexanol is produced from simple and industrially advantageous cyclohexene oxide.
次に、実施例及び比較例を挙げて本発明を説明するが、
本発明はこれらの実施例によって何ら限定されるもので
はない。Next, the present invention will be explained with reference to Examples and Comparative Examples.
The present invention is not limited in any way by these Examples.
実施例１
ゼオライト触媒ＫＳ（日産ガードラー社製）を０．５ｇ
とエタノール１５０ｇをガラス製のフラスコに仕込み、
７０℃に撹拌しながら昇温した。Example 1 0.5 g of zeolite catalyst KS (manufactured by Nissan Girdler)
and 150g of ethanol in a glass flask,
The temperature was raised to 70°C with stirring.
７０℃に達したところでシクロヘキセンオキシドを毎時
７．３ｇの速度でトータル１４．６ｇ供給した。When the temperature reached 70°C, a total of 14.6 g of cyclohexene oxide was fed at a rate of 7.3 g/hour.
シクロヘキセンオキシド仕込終了後、反応粗液を分析し
た結果、シクロヘキセンオキシドの変化率１００％で、
２−エトキシシクロヘキサノールの収率は９６．３％だ
った。After the completion of cyclohexene oxide preparation, the reaction crude liquid was analyzed and the change rate of cyclohexene oxide was 100%.
The yield of 2-ethoxycyclohexanol was 96.3%.
実施例２
ゼオライト触媒ＫＳ（日産ガードラー社製）を１．５ｇ
とエタノール１５０ｇをガラス製のフラスコに仕込み、
７０℃に撹拌しながら昇温した。Example 2 1.5 g of zeolite catalyst KS (manufactured by Nissan Girdler)
and 150g of ethanol in a glass flask,
The temperature was raised to 70°C with stirring.
７０℃に達したところでシクロヘキセンオキシドを毎時
７．３ｇの速度でトータル１４．６ｇ供給した。When the temperature reached 70°C, a total of 14.6 g of cyclohexene oxide was fed at a rate of 7.3 g/hour.
シクロヘキセンオキシド仕込終了後、反応粗液ヲ分析し
た結果、シクロヘキセンオキシドの変化率１００％で、
２−エトキシシクロヘキサノールの収率は９６．４％だ
った。After the completion of cyclohexene oxide preparation, the reaction crude liquid was analyzed and the change rate of cyclohexene oxide was 100%.
The yield of 2-ethoxycyclohexanol was 96.4%.
実施例３
ゼオライト触媒ＫＳ（日産ガードラー社製）を４．５ｇ
とエタノール１５０ｇをガラス製のフラスコに仕込み、
７０℃に撹拌しながら昇温した。Example 3 4.5 g of zeolite catalyst KS (manufactured by Nissan Girdler)
and 150g of ethanol in a glass flask,
The temperature was raised to 70°C with stirring.
７０℃に達したところでシクロヘキセンオキシドを毎時
７．３ｇの速度でトータル１４．６ｇ供給した。When the temperature reached 70°C, a total of 14.6 g of cyclohexene oxide was fed at a rate of 7.3 g/hour.
シクロヘキセンオキシド仕込終了後、反応粗液を分析し
た結果、シクロヘキセンオキシドの変化率１００％で、
２−エトキシシクロヘキサノールの収率は９５．３％た
った。After the completion of cyclohexene oxide preparation, the reaction crude liquid was analyzed and the change rate of cyclohexene oxide was 100%.
The yield of 2-ethoxycyclohexanol was 95.3%.
実施例４
ゼオライト触媒ＫＳ（日産ガードラー社製）を４．５ｇ
とエタノール１００ｇをガラス製のフラスコに仕込み、
７０℃に撹拌しながら昇温した。Example 4 4.5 g of zeolite catalyst KS (manufactured by Nissan Girdler)
and 100g of ethanol in a glass flask,
The temperature was raised to 70°C with stirring.
７０℃に達したところでシクロヘキセンオキシドを毎時
７．３ｇの速度でトータル１４．６ｇ供給した。When the temperature reached 70°C, a total of 14.6 g of cyclohexene oxide was fed at a rate of 7.3 g/hour.
シクロヘキセンオキシド仕込終了後、反応粗液を分析し
た結果、シクロヘキセンオキシドの変化率１００％で、
２−エトキシシクロヘキサノールの収率は９３．２％だ
った。After the completion of cyclohexene oxide preparation, the reaction crude liquid was analyzed and the change rate of cyclohexene oxide was 100%.
The yield of 2-ethoxycyclohexanol was 93.2%.
比較例
酢酸１３．１ｇとエタノール１５０ｇをガラス製のフラ
スコに仕込み、７０℃に撹拌しながら昇温した。Comparative Example 13.1 g of acetic acid and 150 g of ethanol were placed in a glass flask, and the temperature was raised to 70° C. with stirring.
７０℃に達したところでシクロヘキセンオキシドを毎時
７．３ｇの速度でトータル１４．６ｇ供給した。When the temperature reached 70°C, a total of 14.6 g of cyclohexene oxide was fed at a rate of 7.3 g/hour.
シクロヘキセンオキシド仕込終了後、反応粗液を分析し
た結果、シクロヘキセンオキシドの変化率６８．２％で
、２−エトキシシクロヘキサノールの収率は６１．４％
だった。After the completion of the cyclohexene oxide preparation, analysis of the reaction crude liquid revealed that the conversion rate of cyclohexene oxide was 68.2%, and the yield of 2-ethoxycyclohexanol was 61.4%.
was.
この比較例は、反応後蒸溜分離の必要な触媒の一つであ
る酢酸を使用して反応させても反応速度が非常に遅く、
無機固体酸が触媒活性の面でも優れていることを示して
いる。In this comparative example, the reaction rate was very slow even if the reaction was carried out using acetic acid, which is one of the catalysts that requires distillation separation after the reaction.
This shows that inorganic solid acids are also superior in terms of catalytic activity.
Claims (2)
せて２−アルコキシシクロヘキサノールを製造する方法
において、無機固体酸触媒の存在下で反応させることを
特徴とする２−アルコキシシクロヘキサノールの製造方
法。(1) A method for producing 2-alkoxycyclohexanol by reacting cyclohexene oxide and an alcohol, which is characterized in that the reaction is carried out in the presence of an inorganic solid acid catalyst.
囲第（１）項に記載の２−アルコキシシクロヘキサノー
ルの製造方法。(2) The method for producing 2-alkoxycyclohexanol according to claim (1), wherein the inorganic solid acid catalyst is a zeolite.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2159381A JPH0449261A (en) | 1990-06-18 | 1990-06-18 | Production of 2-alkoxycyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2159381A JPH0449261A (en) | 1990-06-18 | 1990-06-18 | Production of 2-alkoxycyclohexanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0449261A true JPH0449261A (en) | 1992-02-18 |
Family
ID=15692567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2159381A Pending JPH0449261A (en) | 1990-06-18 | 1990-06-18 | Production of 2-alkoxycyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0449261A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006193508A (en) * | 2004-12-13 | 2006-07-27 | Sumitomo Chemical Co Ltd | Method for producing alcohol |
| US7132092B2 (en) | 2002-02-08 | 2006-11-07 | Sumitomo Chemical Company, Limited | Metallized mesoporous silicate and method of oxidation with the same |
-
1990
- 1990-06-18 JP JP2159381A patent/JPH0449261A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7132092B2 (en) | 2002-02-08 | 2006-11-07 | Sumitomo Chemical Company, Limited | Metallized mesoporous silicate and method of oxidation with the same |
| JP2006193508A (en) * | 2004-12-13 | 2006-07-27 | Sumitomo Chemical Co Ltd | Method for producing alcohol |
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