JP2003252808A - Method for producing hydrating reaction product using water near critical point as reaction field - Google Patents
Method for producing hydrating reaction product using water near critical point as reaction fieldInfo
- Publication number
- JP2003252808A JP2003252808A JP2002050710A JP2002050710A JP2003252808A JP 2003252808 A JP2003252808 A JP 2003252808A JP 2002050710 A JP2002050710 A JP 2002050710A JP 2002050710 A JP2002050710 A JP 2002050710A JP 2003252808 A JP2003252808 A JP 2003252808A
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- Prior art keywords
- organic compound
- reaction product
- water
- hydration reaction
- acid catalyst
- Prior art date
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、一般に超臨界水又
は亜臨界水と呼ばれる状態を含む臨界点近傍の水を用い
て、有機化合物の水和反応を行う、水和反応生成物の製
造方法に関する。TECHNICAL FIELD The present invention relates to a method for producing a hydration reaction product, in which a hydration reaction of an organic compound is carried out using water in the vicinity of a critical point containing a state generally called supercritical water or subcritical water. Regarding
【０００２】[0002]
【従来の技術】超臨界流体は、新規な化学合成反応場と
して注目されている。特に超臨界水は、圧力・温度の変
化で連続的に流体の諸物性を制御できる点などから、様
々な反応系への利用が考えられている。例えば、超臨界
水を用いる系として、1)排水中の汚染物質の抽出・分解
除去、2)汚泥の分解、3)石炭及び重質原油の分解処理、
4)廃プラスチックの分解・再利用（ケミカル・リサイク
ル）などが考えられ、且つ行われている。2. Description of the Related Art Supercritical fluids are drawing attention as a new chemical synthesis reaction field. In particular, supercritical water is considered to be used in various reaction systems because it can continuously control various physical properties of fluids by changing pressure and temperature. For example, as a system using supercritical water, 1) extraction and decomposition removal of pollutants in wastewater, 2) decomposition of sludge, 3) decomposition treatment of coal and heavy crude oil,
4) Decomposition / reuse (chemical recycling) of waste plastic is considered and is being carried out.
【０００３】また、超臨界水は、その酸特性により、ベ
ックマン転位及びピナコール転位、加水分解反応、並び
にディールス−アルダー反応における反応速度が増すこ
とが報告されている。しかしながら、超臨界水を用いる
系はいずれも分解反応が主であり、生成反応に用いる系
は少数であった。It has been reported that supercritical water increases the reaction rate in Beckmann rearrangement and pinacol rearrangement, hydrolysis reaction, and Diels-Alder reaction due to its acid property. However, all of the systems using supercritical water are mainly decomposition reactions, and the number of systems used for production reaction was small.
【０００４】一方、酸触媒を用いて有用な化学物質を製
造する方法が種々提案されている。均一系の酸触媒を用
いる系として、例えば原料としてプロピレンを用い且つ
酸触媒として硫酸を用い、水和反応により2-プロパノー
ルを製造する方法がある。この方法は工業化されている
方法であるが、強酸である硫酸のハンドリング、均一系
であるために生成物である2-プロパノールと硫酸との分
離、などの問題を有している。このような均一系の酸触
媒の問題を解決すべく、固体酸触媒を用いることが提案
されている。On the other hand, various methods for producing useful chemical substances using an acid catalyst have been proposed. As a system using a homogeneous acid catalyst, for example, there is a method of producing 2-propanol by a hydration reaction using propylene as a raw material and sulfuric acid as an acid catalyst. Although this method is an industrialized method, it has problems such as handling of sulfuric acid which is a strong acid and separation of 2-propanol which is a product and sulfuric acid due to its homogenous system. In order to solve the problem of such a homogeneous acid catalyst, it has been proposed to use a solid acid catalyst.
【０００５】[0005]
【発明が解決しようとする課題】しかしながら、超臨界
水又は亜臨界水と呼ばれる状態を含む臨界点近傍の水と
固体酸触媒とを共に用いて、有用な物質を得る方法は未
だ提案されていない。したがって、超臨界水又は亜臨界
水と呼ばれる状態を含む臨界点近傍の水と固体酸触媒と
を共に用いて、反応媒体の酸性質による固体酸触媒の機
能の向上を図ることにより、有用な物質を得る方法が要
望されている。However, there has not been proposed yet a method for obtaining a useful substance by using both water near the critical point including a state called supercritical water or subcritical water and a solid acid catalyst. . Therefore, by using water in the vicinity of a critical point including a state called supercritical water or subcritical water and a solid acid catalyst together to improve the function of the solid acid catalyst due to the acid nature of the reaction medium, a useful substance Is needed.
【０００６】本発明の目的は、固体酸触媒を用いた系に
超臨界水又は亜臨界水と呼ばれる状態を含む臨界点近傍
の水を用いて、有用な物質、即ち有機化合物からの水和
反応生成物を製造する方法を提供することにある。ま
た、本発明の目的は、上記目的の他に、又は上記目的に
加えて、この方法によって得られる有用な物質、即ち有
機化合物からの水和反応生成物を提供することにある。The object of the present invention is to hydrate a useful substance, that is, an organic compound, by using water near a critical point including a state called supercritical water or subcritical water in a system using a solid acid catalyst. It is to provide a method for producing a product. Another object of the present invention is to provide, in addition to or in addition to the above objects, a useful substance obtained by this method, that is, a hydration reaction product from an organic compound.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、以下の発
明により、上記課題を解決できることを見出した。即
ち、＜１＞ 有機化合物に水分子を付加して前記有機化
合物の水和反応物を得る水和反応生成物の製造方法であ
って、前記有機化合物を固体酸触媒の存在下であって臨
界点近傍の条件にある水の存在下に置き該有機化合物の
水和反応物を得る反応工程を有する、上記方法。The present inventors have found that the above problems can be solved by the following inventions. That is, <1> A method for producing a hydration reaction product, wherein a water molecule is added to an organic compound to obtain a hydration reaction product of the organic compound, the organic compound being in the presence of a solid acid catalyst, The above method, which comprises a reaction step of obtaining a hydration reaction product of the organic compound by placing it in the presence of water under conditions near the point.
【０００８】＜２＞ 上記＜１＞において、臨界点近傍
の条件は、温度が２５０〜４００℃であり且つ圧力が２
０〜３５ＭＰａであるのがよい。
＜３＞ 上記＜１＞又は＜２＞において、反応工程前
に、有機化合物を水に溶解させて有機化合物の溶液を得
る溶液調製工程を有するのがよい。<2> In the above item <1>, the condition near the critical point is that the temperature is 250 to 400 ° C. and the pressure is 2
It is preferably 0 to 35 MPa. <3> In the above item <1> or <2>, it is preferable to have a solution preparation step of dissolving the organic compound in water to obtain a solution of the organic compound before the reaction step.
【０００９】＜４＞ 上記＜１＞〜＜３＞のいずれかに
おいて、有機化合物がオレフィン類から選ばれ、水和反
応物は、オレフィン類のマルコフニコフ則に従って得ら
れるアルコール類であるのがよい。
＜５＞ 上記＜４＞において、有機化合物がプロピレン
であり、水和反応物が2-プロパノールであるのがよい。<4> In any one of the above items <1> to <3>, the organic compound is selected from olefins, and the hydration reaction product is preferably an alcohol obtained according to Markovnikov rule of olefins. . <5> In the above item <4>, the organic compound may be propylene, and the hydration reaction product may be 2-propanol.
【００１０】＜６＞ 上記＜１＞〜＜５＞のいずれかに
おいて、固体酸触媒がＭｏＯ３／Ａｌ２Ｏ３、Ａｌ２Ｏ
３、ＴｉＯ２、ＷＯ３、Ｖ２Ｏ５、硫酸化ジルコニア、
ＴｉＯ２−ＺｒＯ２、ＳｎＯ３−ＭｏＯ３、ビスマス−
モリブデン複合酸化物、ヘテロポリ酸、ゼオライト、金
属酸化物／Ａｌ２Ｏ３、及び金属酸化物／ＴｉＯ２から
なる群から選ばれる少なくとも１種であるのがよい。
＜７＞ 上記＜１＞〜＜６＞のいずれかにおいて、固体
酸触媒がＭｏＯ３／Ａｌ２Ｏ３であるのがよい。
＜８＞ 上記＜４＞において、有機化合物がプロピレン
であり、固体酸触媒がＭｏＯ３／Ａｌ２Ｏ３であり、且
つ水和反応物が2-プロパノールであるのがよい。<6> In any one of the above items <1> to <5>, the solid acid catalyst is MoO 3 / Al 2 O 3 or Al 2 O.
3 , TiO 2 , WO 3 , V 2 O 5 , sulfated zirconia,
TiO 2 -ZrO 2, SnO 3 -MoO 3, bismuth -
It is preferably at least one selected from the group consisting of molybdenum composite oxide, heteropolyacid, zeolite, metal oxide / Al 2 O 3 , and metal oxide / TiO 2 . <7> In any one of the above items <1> to <6>, the solid acid catalyst may be MoO 3 / Al 2 O 3 . <8> In the above item <4>, the organic compound may be propylene, the solid acid catalyst may be MoO 3 / Al 2 O 3 , and the hydration reaction product may be 2-propanol.
【００１１】＜９＞ 上記＜１＞〜＜８＞の方法によっ
て得られる水和反応物。
＜１０＞ 上記＜１＞〜＜８＞の方法によって得られる
水和反応物であって、有機化合物がプロピレンであり、
且つ水和反応物が2-プロパノールであるのがよい。
＜１１＞ 上記＜１＞〜＜８＞の方法によって得られる
水和反応物であって、有機化合物がプロピレンであり、
固体酸触媒がＭｏＯ３／Ａｌ２Ｏ３であり、且つ水和反
応物が2-プロパノールであるのがよい。<9> A hydration reaction product obtained by the method of <1> to <8> above. <10> A hydration reaction product obtained by the method according to <1> to <8>, wherein the organic compound is propylene,
And the hydration reaction product may be 2-propanol. <11> A hydration reaction product obtained by the method according to <1> to <8>, wherein the organic compound is propylene,
The solid acid catalyst may be MoO 3 / Al 2 O 3 and the hydration reactant may be 2-propanol.
【００１２】[0012]
【発明の実施の形態】以下、本発明を詳細に説明する。
本発明の水和反応生成物の製造方法は、有機化合物を固
体酸触媒の存在下であって臨界点近傍の条件にある水の
存在下に置き該有機化合物の水和反応物を得る反応工程
を有する。また、本発明の方法は、反応工程前に、有機
化合物を水に溶解させて有機化合物の溶液を得る溶液調
製工程を有していてもよい。BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
The method for producing a hydration reaction product of the present invention comprises a reaction step in which an organic compound is placed in the presence of a solid acid catalyst in the presence of water under conditions near the critical point to obtain a hydration reaction product of the organic compound. Have. In addition, the method of the present invention may have a solution preparation step of dissolving the organic compound in water to obtain a solution of the organic compound before the reaction step.
【００１３】本明細書において、「水の臨界点近傍の条
件」とは、温度が２５０〜４００℃であり且つ圧力が２
０〜３５ＭＰａであるのがよい。なお、水の臨界点は、
臨界温度：３７３．９５℃、臨界圧力：２２．０６４Ｍ
Ｐａである。In the present specification, the "condition near the critical point of water" means that the temperature is 250 to 400 ° C and the pressure is 2
It is preferably 0 to 35 MPa. The critical point of water is
Critical temperature: 373.95 ° C, critical pressure: 22.064M
Pa.
【００１４】なお、上記の範囲は、好ましくは温度が３
００〜４００℃であり且つ圧力が２０〜３５ＭＰａ、よ
り好ましくは温度が３４０〜３８０℃であり且つ圧力が
２４〜３０ＭＰａであるのがよい。In the above range, the temperature is preferably 3
It is preferable that the temperature is 00 to 400 ° C. and the pressure is 20 to 35 MPa, more preferably the temperature is 340 to 380 ° C. and the pressure is 24 to 30 MPa.
【００１５】本発明の方法において、水和反応生成物の
原料である有機化合物は、水和反応を生じるものであれ
ば限定されないが、例えばオレフィン類を挙げることが
できる。オレフィン類である場合、水和反応物はマルコ
フニコフ則に従って得られるアルコール類である。な
お、本明細書において、「マルコフニコフ則に従って得
られるアルコール類」とあるのは、結果物として得られ
る水和物である「アルコール類」の水の付加の状態を意
味するのであって、反応メカニズムを意味するものでは
ない。なお、オレフィン類として、エチレン、プロピレ
ン、ブテン、ペンテン、ヘキセン、シクロヘキセンなど
を挙げることができるが、これらに限定されない。In the method of the present invention, the organic compound which is a raw material of the hydration reaction product is not limited as long as it causes a hydration reaction, and examples thereof include olefins. In the case of olefins, hydration reactants are alcohols obtained according to Markovnikov rules. In the present specification, the term “alcohols obtained according to Markovnikov rule” means the state of addition of water to the resulting hydrate “alcohols”, and the reaction It does not mean a mechanism. The olefins may include, but are not limited to, ethylene, propylene, butene, pentene, hexene, cyclohexene, and the like.
【００１６】本発明に用いられる触媒は、固体酸触媒と
して機能するものであれば特に限定されない。例えば、
Ａｌ２Ｏ３、ＭｏＯ３／Ａｌ２Ｏ３（担持体としてＡｌ
２Ｏ ３を用い、そこにＭｏＯ３を担持させたもの、以降
も「／」を用いた場合は同様の意である）、ＴｉＯ２、
ＷＯ３、Ｖ２Ｏ５、硫酸化ジルコニア、ＴｉＯ２−Ｚｒ
Ｏ２（なお、「−」は成分系を示し、以降も同様の意で
ある）、ＳｎＯ３−ＭｏＯ３、ビスマス−モリブデン複
合酸化物、ヘテロポリ酸、ゼオライト、金属酸化物／Ａ
ｌ２Ｏ３、及び金属酸化物／ＴｉＯ２を挙げることがで
きるがこれらに限定されない。The catalyst used in the present invention is a solid acid catalyst.
There is no particular limitation as long as it functions as a function. For example,
AlTwoOThree, MoOThree/ AlTwoOThree(Al as a carrier
TwoO ThreeUsing MoOThreeThe one carrying
Also has the same meaning when "/" is used), TiOTwo,
WOThree, VTwoO5, Sulfated zirconia, TiOTwo-Zr
OTwo(Note that "-" indicates a component system, and the same meaning applies hereafter.
Yes), SnOThree-MoOThree, Bismuth-molybdenum compound
Compound oxide, heteropoly acid, zeolite, metal oxide / A
lTwoOThree, And metal oxide / TiOTwoTo mention
However, it is not limited to these.
【００１７】本発明の方法により、水和反応生成物を高
い選択率で得ることができる。例えば、原料としてオレ
フィン類を用いた場合、本発明の方法によって得られる
「マルコフニコフ則に従って得られるアルコール類」
は、選択率８０％以上、好ましくは９５％以上で得るこ
とができる。例えば、原料としてプロピレンを用い、固
体酸触媒としてＭｏＯ３／Ａｌ２Ｏ３を用いた場合、2-
プロパノールてを選択率９５％以上で得ることができ
る。By the method of the present invention, the hydration reaction product can be obtained with high selectivity. For example, when olefins are used as raw materials, "alcohols obtained according to Markovnikov rule" obtained by the method of the present invention
Can be obtained with a selectivity of 80% or more, preferably 95% or more. For example, when propylene is used as a raw material and MoO 3 / Al 2 O 3 is used as a solid acid catalyst,
Propanol can be obtained with a selectivity of 95% or more.
【００１８】特に、原料である有機化合物がプロピレン
であり、固体酸触媒がＭｏＯ３／Ａｌ２Ｏ３であり水和
反応物が2-プロパノールであるのがよい。また、この際
の水の臨界点近傍の条件は、温度３４０〜３８０℃、圧
力２４〜３０ＭＰａであるのがよい。即ち、本発明の方
法により、プロピレンから2-プロパノールを製造するこ
とができる。従来、プロピレンからの2-プロパノールの
製法において、触媒として硫酸を用いていたものが、本
発明では用いなくて済むため、次のような効果を奏す
る。即ち、1)硫酸を用いずに済むため触媒のハンドリン
グが容易である；2)用いた硫酸を後に分離する工程が本
発明は省略できる；などの効果を奏する。また、上述の
効果も奏することができる。即ち、高い選択率で2-プロ
パノールを製造することができる。Particularly, it is preferable that the organic compound as a raw material is propylene, the solid acid catalyst is MoO 3 / Al 2 O 3 , and the hydration reaction product is 2-propanol. The conditions near the critical point of water at this time are preferably a temperature of 340 to 380 ° C. and a pressure of 24 to 30 MPa. That is, 2-propanol can be produced from propylene by the method of the present invention. Conventionally, sulfuric acid is used as a catalyst in a method for producing 2-propanol from propylene, but it is not necessary to use it in the present invention, so that the following effects are obtained. That is, 1) it is not necessary to use sulfuric acid, so that the handling of the catalyst is easy; 2) the step of separating the used sulfuric acid later can be omitted in the present invention; In addition, the above-mentioned effects can be achieved. That is, 2-propanol can be produced with high selectivity.
【００１９】[0019]
【実施例】以下、実施例を用いて本発明を具体的に説明
するが、実施例は単に例示であって、本発明を限定する
ものと解釈してはならない。
（実施例１）飽和器内に水を用意し、該水にプロピレン
気体を一晩、溶解させてプロピレン溶液を準備した。こ
の際、プロピレンの圧力：０．８ＭＰａ、室温で行っ
た。EXAMPLES The present invention will be specifically described below with reference to examples, but the examples are merely illustrative and should not be construed as limiting the present invention. (Example 1) Water was prepared in a saturator, and propylene gas was dissolved in the water overnight to prepare a propylene solution. At this time, the pressure of propylene was 0.8 MPa and the temperature was room temperature.
【００２０】プロピレン溶液とは別に、反応器Ａを準備
した。反応器Ａは、長さ：２５ｃｍ、内径：０．４ｃｍ
のSUS-316製チューブ内に、ＭｏＯ３／Ａｌ２Ｏ３（Ｍ
ｏＯ ３の量は、ＭｏＯ３／Ａｌ２Ｏ３ １００重量％
中、１重量％）を２．０ｇ充填した。ＭｏＯ３／Ａｌ２
Ｏ３は、平均粒径：１ｍｍ、比表面積：８８ｍ２／ｇで
あった。Prepare reactor A separately from propylene solution
did. Reactor A has a length of 25 cm and an inner diameter of 0.4 cm.
MoO in the SUS-316 tubeThree/ AlTwoOThree(M
oO ThreeThe amount of MoOThree/ AlTwoOThree 100% by weight
2.0 g of (1% by weight). MoOThree/ AlTwo
OThreeHas an average particle diameter of 1 mm and a specific surface area of 88 mTwo/ G
there were.
【００２１】プロピレン溶液がＨＰＬＣポンプ（東ソー
社製）によって加圧され予熱ライン（ハステロイC276製
チューブ、内径：０．１０８ｃｍ；長さ：３ｍ）を通っ
て反応器に導かれるように、且つ予熱ライン及び反応器
が共に加熱されるように、反応装置を設置した。なお、
反応器内の温度を熱電対でモニターした。また、反応器
から生じる液体状成分及び気体状成分を含む生成物を、
ＧＣ−ＦＩＤ及びＧＣ−ＴＣＤでそれぞれ定量した。The propylene solution is pressurized by an HPLC pump (manufactured by Tosoh Corporation) and introduced into the reactor through a preheating line (Hastelloy C276 tube, inner diameter: 0.108 cm; length: 3 m), and the preheating line And the reactor was installed so that the reactor and the reactor were both heated. In addition,
The temperature inside the reactor was monitored with a thermocouple. In addition, the product containing a liquid component and a gaseous component generated from the reactor,
It was quantified by GC-FID and GC-TCD, respectively.
【００２２】定温（３４８℃（■）及び３８５℃
（●））で、圧力を変化させた（２１．６ＭＰａ〜３
１．４ＭＰａ）場合のプロピレンの変換率を図１に示
す。図１からわかるように、水の臨界点近傍の条件、即
ち３４８℃の定温で圧力を２０．５ＭＰａ〜３１．４Ｍ
Ｐａで変化させたもの（■）は、３８５℃のもの（●）
よりも高変換率を有することがわかる。特に、温度３４
８℃、圧力３１．４ＭＰａで、最も高い変換率を有する
ことがわかる。Constant temperature (348 ° C (■) and 385 ° C
(●), the pressure was changed (21.6 MPa to 3).
The conversion rate of propylene in the case of 1.4 MPa) is shown in FIG. As can be seen from FIG. 1, the pressure is 20.5 MPa to 31.4 M at a condition near the critical point of water, that is, at a constant temperature of 348 ° C.
The value changed with Pa (■) is 385 ° C (●)
It can be seen that it has a higher conversion rate than. In particular, the temperature 34
It can be seen that it has the highest conversion rate at 8 ° C. and a pressure of 31.4 MPa.
【００２３】（実施例２）実施例１の反応器１と同様
に、反応器２及び反応器３を調製した。但し、反応器２
は、ＭｏＯ３／Ａｌ２Ｏ３の代わりにＡｌ２Ｏ３（平均
粒径：１ｍｍ、比表面積：８８ｍ２／ｇ、２ｇ）を用い
た。また、反応器３は、ＭｏＯ３／Ａｌ２Ｏ ３の代わり
には何も充填しなかった。(Example 2) Same as the reactor 1 of Example 1
Then, the reactor 2 and the reactor 3 were prepared. However, reactor 2
Is MoOThree/ AlTwoOThreeInstead of AlTwoOThree(average
Particle size: 1 mm, specific surface area: 88 mTwo/ G, 2g)
It was Also, the reactor 3 is MoOThree/ AlTwoO Threeinstead of
Was not filled with anything.
【００２４】反応器１〜３を用いて、定圧：２５．５Ｍ
Ｐａで、温度を変化させた（１００〜４２０℃）場合の
プロピレンの変換率を図２に示す。図２中、■は反応器
１（ＭｏＯ３／Ａｌ２Ｏ３）、●は反応器２（Ａｌ２Ｏ
３）、▲は反応器３（触媒なし）を示す。Using reactors 1 to 3, constant pressure: 25.5M
The conversion rate of propylene when the temperature is changed in Pa (100 to 420 ° C.) is shown in FIG. In FIG. 2, ■ represents reactor 1 (MoO 3 / Al 2 O 3 ), and ● represents reactor 2 (Al 2 O 3 ).
3 ) and ▲ indicate the reactor 3 (without catalyst).
【００２５】図２からわかるように、反応器１〜３のい
ずれも、水の臨界温度３７３．９５℃を越えた温度であ
る４００℃では、プロピレンの変換率が著しく低下し
た。また、反応器１（ＭｏＯ３／Ａｌ２Ｏ３）を用いた
場合、圧力：２５．５ＭＰａ、温度：３８０℃でプロピ
レンの高変換率をもたらすことがわかる。As can be seen from FIG. 2, in all of the reactors 1 to 3, at 400 ° C., which is a temperature exceeding the critical temperature of water of 373.95 ° C., the conversion rate of propylene was remarkably lowered. Further, it is found that when the reactor 1 (MoO 3 / Al 2 O 3 ) is used, a high conversion rate of propylene is obtained at a pressure of 25.5 MPa and a temperature of 380 ° C.
【００２６】[0026]
【発明の効果】本発明により、超臨界水又は亜臨界水と
呼ばれる状態を含む臨界点近傍の水を用いた系により、
有用な物質、即ち有機化合物からの水和反応生成物を製
造する方法を提供することができる。また、本発明によ
り、上記効果の他に、又は上記効果に加えて、この方法
によって得られる有用な物質、即ち有機化合物からの水
和反応生成物を提供することができる。According to the present invention, a system using water in the vicinity of the critical point including a state called supercritical water or subcritical water
It is possible to provide a method for producing a hydration reaction product from a useful substance, that is, an organic compound. In addition to the above effects or in addition to the above effects, the present invention can provide a useful substance obtained by this method, that is, a hydration reaction product from an organic compound.
【図１】 実施例１の結果を示す図である。FIG. 1 is a diagram showing the results of Example 1.
【図２】 実施例２の結果を示す図である。FIG. 2 is a diagram showing the results of Example 2.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4H006 AA02 AC41 BA09 BA10 BA11 BA13 BA14 BA30 BB31 BC10 BC11 BE60 DA10 FE11 4H039 CA60 CF10 ─────────────────────────────────────────────────── ─── Continued front page F-term (reference) 4H006 AA02 AC41 BA09 BA10 BA11 BA13 BA14 BA30 BB31 BC10 BC11 BE60 DA10 FE11 4H039 CA60 CF10
Claims (8)
化合物の水和反応物を得る水和反応生成物の製造方法で
あって、前記有機化合物を固体酸触媒の存在下であって
臨界点近傍の条件にある水の存在下に置き該有機化合物
の水和反応物を得る反応工程を有する、上記方法。1. A method for producing a hydration reaction product, wherein a water molecule is added to an organic compound to obtain a hydration reaction product of the organic compound, wherein the organic compound is prepared in the presence of a solid acid catalyst. The above method, which comprises a reaction step of obtaining a hydration reaction product of the organic compound by placing it in the presence of water under conditions near the point.
５０〜４００℃であり且つ圧力が２０〜３５ＭＰａであ
る請求項１記載の方法。2. The temperature near the critical point of the water is 2
The method according to claim 1, wherein the temperature is 50 to 400 ° C. and the pressure is 20 to 35 MPa.
に溶解させて前記有機化合物の溶液を得る溶液調製工程
を有する請求項１又は２記載の方法。3. The method according to claim 1, further comprising a solution preparation step of dissolving the organic compound in water to obtain a solution of the organic compound before the reaction step.
れ、前記水和反応物は、前記オレフィン類のマルコフニ
コフ則に従って得られるアルコール類である請求項１〜
３のいずれか１項記載の方法。4. The organic compound is selected from olefins, and the hydration reaction product is an alcohol obtained according to the Markovnikov rule of the olefins.
The method according to any one of 3 above.
記水和反応物が2-プロパノールである請求項４記載の方
法。5. The method according to claim 4, wherein the organic compound is propylene and the hydration reaction product is 2-propanol.
２Ｏ３、Ａｌ２Ｏ３、ＴｉＯ ２、ＷＯ３、Ｖ２Ｏ５、硫
酸化ジルコニア、ＴｉＯ２−ＺｒＯ２、ＳｎＯ３−Ｍｏ
Ｏ３、ビスマス−モリブデン複合酸化物、ヘテロポリ
酸、ゼオライト、金属酸化物／Ａｌ２Ｏ３、及び金属酸
化物／ＴｉＯ２からなる群から選ばれる少なくとも１種
である請求項１〜５のいずれか１項記載の方法。6. The solid acid catalyst is MoO.Three/ Al
TwoOThree, AlTwoOThree, TiO Two, WOThree, VTwoO5, Sulfur
Zirconia oxide, TiOTwo-ZrOTwo, SnOThree-Mo
OThree, Bismuth-molybdenum composite oxide, heteropoly
Acid, zeolite, metal oxide / AlTwoOThree, And metallic acid
Compound / TiOTwoAt least one selected from the group consisting of
The method according to any one of claims 1 to 5, wherein
である請求項１〜６のいずれか１項記載の方法。7. The solid acid catalyst is MoO 3 / Al 2 O 3
The method according to any one of claims 1 to 6, wherein
記固体酸触媒がＭｏＯ ３／Ａｌ２Ｏ３であり、且つ前記
水和反応物が2-プロパノールである請求項４記載の方
法。8. The organic compound is propylene,
The solid acid catalyst is MoO. Three/ AlTwoOThreeAnd said
The method according to claim 4, wherein the hydration reaction product is 2-propanol.
Law.
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| US11023122B2 (en) | 2006-09-06 | 2021-06-01 | Apple Inc. | Video manager for portable multifunction device |
| US11106326B2 (en) | 2006-09-06 | 2021-08-31 | Apple Inc. | Portable electronic device, method, and graphical user interface for displaying structured electronic documents |
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