JP2007254413A - Method for hydrogenation of olefin - Google Patents
Method for hydrogenation of olefin Download PDFInfo
- Publication number
- JP2007254413A JP2007254413A JP2006082764A JP2006082764A JP2007254413A JP 2007254413 A JP2007254413 A JP 2007254413A JP 2006082764 A JP2006082764 A JP 2006082764A JP 2006082764 A JP2006082764 A JP 2006082764A JP 2007254413 A JP2007254413 A JP 2007254413A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- olefin
- gas
- packed bed
- liquid
- 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
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 35
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 25
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- 239000007789 gas Substances 0.000 claims abstract description 48
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 239000007787 solid Substances 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 239000010419 fine particle Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 4
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 3
- 150000004706 metal oxides Chemical class 0.000 abstract description 3
- 229910000510 noble metal Inorganic materials 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 229910052703 rhodium Inorganic materials 0.000 abstract description 2
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- -1 Sm 2 O 3 Inorganic materials 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910021193 La 2 O 3 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay 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
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- VASIZKWUTCETSD-UHFFFAOYSA-N manganese(II) oxide Inorganic materials [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003440 styrenes 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
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明は、オレフィンの水添方法に関するものである。更に詳しくは、固体水添触媒の充填層にオレフィンを含む液と水素を含むガスとの液ガス混合物を通過させるオレフィンの水添方法において、高流速で液ガス混合物を通過させ、かつ、充填層の差圧を低減できるという優れた効果を有するオレフィンの水添方法に関するものである。 The present invention relates to a method for hydrogenating olefins. More specifically, in the olefin hydrogenation method in which a liquid gas mixture of a liquid containing olefin and a gas containing hydrogen is passed through a packed bed of a solid hydrogenation catalyst, the liquid gas mixture is passed at a high flow rate, and the packed bed The present invention relates to a method for hydrogenating olefins, which has an excellent effect of being able to reduce the differential pressure.
固体水添触媒の充填層にオレフィンを含有する液と水素を含むガスを通過させるオレフィンの水添方法としては、例えば、α―メチルスチレンと水素をアップフローまたはダウンフローで触媒層に供給し、水添する技術が開示されている（特許文献１参照）。しかし、このような固体の水添触媒の充填層に液とガスの混合物を供給するに際し、充填層の差圧は工業的に安定運転を行うという観点で重要な因子であるにも拘わらず、ほとんど有用な記載がなく一層の改良が求められていた。 As a method for hydrogenating an olefin in which a liquid containing olefin and a gas containing hydrogen are passed through a packed bed of a solid hydrogenation catalyst, for example, α-methylstyrene and hydrogen are supplied to the catalyst layer by upflow or downflow, A hydrogenation technique is disclosed (see Patent Document 1). However, when supplying a mixture of liquid and gas to the packed bed of such a solid hydrogenation catalyst, the differential pressure in the packed bed is an important factor in terms of industrially stable operation, There was almost no useful description and further improvement was demanded.
かかる状況において、本発明が解決しようとする課題は、固体水添触媒の充填層にオレフィンを含む液と水素を含むガスとの液ガス混合物を通過させるオレフィンの水添方法において、高流速で液ガス混合物を通過させ、かつ、充填層の差圧を低減できるという優れた効果を有するオレフィンの水添方法を提供する点にある。 In such a situation, the problem to be solved by the present invention is to provide a olefin hydrogenation method in which a liquid gas mixture of a liquid containing olefin and a gas containing hydrogen is passed through a packed bed of a solid hydrogenation catalyst at a high flow rate. The object is to provide an olefin hydrogenation method having an excellent effect of allowing a gas mixture to pass through and reducing a differential pressure in a packed bed.
すなわち、本発明は、固体水添触媒の充填層にオレフィンを含む液と水素を含むガスとの液ガス混合物を通過させるオレフィンの水添方法において、該触媒充填層中に含有する直径１ｍｍ以下の触媒微紛の割合を５重量％以下であって、かつ、通過させる液ガス混合物の流速がガス空塔速度３ｃｍ／ｓｅｃ以上であることを特徴とするオレフィンの水添方法に係るものである。 That is, the present invention provides an olefin hydrogenation method in which a liquid gas mixture of a liquid containing olefin and a gas containing hydrogen is passed through a packed bed of a solid hydrogenation catalyst, and the catalyst containing bed has a diameter of 1 mm or less. The present invention relates to a method for hydrogenating olefins, characterized in that the proportion of catalyst fines is 5% by weight or less and the flow rate of the liquid gas mixture to be passed is a gas superficial velocity of 3 cm / sec or more.
本発明により、固体水添触媒の充填層にオレフィンを含有する液と水素を含むガスをガス空塔速度３ｃｍ／ｓｅｃ以上の流速で通過させるオレフィンの水添方法であって、反応器の差圧を低減できるという優れた効果を有するオレフィンの水添方法を提供することができる。 According to the present invention, there is provided a method for hydrogenating an olefin in which a liquid containing olefin and a gas containing hydrogen are passed through a packed bed of a solid hydrogenation catalyst at a gas superficial velocity of 3 cm / sec or more, which includes a differential pressure in a reactor. It is possible to provide a method for hydrogenating olefins having an excellent effect of reducing the amount of hydrogen.
固体水添触媒としては、オレフィンを水添するもので、たとえば、成分としてＣｕＯ、Ｃｒ2Ｏ3、ＺｎＯ、ＦｅＯ3、Ａｌ2Ｏ3、Ｌａ2Ｏ3、Ｓｍ2Ｏ3、ＣｅＯ2、ＺｒＯ2、ＴｉＯ2、ＳｉＯ2、ＭｎＯ2、Ｃｏ2Ｏ3、ＮｉＯ、ＢａＯ、ＣａＯ、ＭｇＯを少なくとも１種類含有する金属酸化物や、Ｐｄ、Ｒｈ、Ｐｔ、Ｒｕを含む貴金属触媒があげられる。 As the solid hydrogenation catalyst, olefin is hydrogenated, for example, CuO, Cr 2 O 3 , ZnO, FeO 3 , Al 2 O 3 , La 2 O 3 , Sm 2 O 3 , CeO 2 , ZrO as components. 2 , metal oxides containing at least one kind of TiO 2 , SiO 2 , MnO 2 , Co 2 O 3 , NiO, BaO, CaO and MgO, and noble metal catalysts containing Pd, Rh, Pt and Ru.
本発明の固体水添触媒としては担体を用いたもの、用いないものいずれでも良い。担体としては、シリカ、アルミナ、チタニア、ジルコニア、マグネシア、シリカアルミナなどの金属酸化物及びこれらの複合酸化物；ベントナイト、モンモリロナイト、ケイソウ土、酸性白土、活性炭、セラミック等をあげることができる。固体水添触媒の形状としては、打錠成型触媒(タブレット円柱状)／球形触媒／押出成型触媒(円柱状)等をあげることができ、各実施する各々の反応様式により最適な形状の触媒が選択される。 The solid hydrogenation catalyst of the present invention may be either using a carrier or not. Examples of the carrier include metal oxides such as silica, alumina, titania, zirconia, magnesia, silica alumina, and complex oxides thereof; bentonite, montmorillonite, diatomaceous earth, acidic clay, activated carbon, ceramic, and the like. Examples of the shape of the solid hydrogenation catalyst include a tableting catalyst (tablet cylindrical shape) / spherical catalyst / extrusion molding catalyst (cylindrical shape), etc. Selected.
固体水添触媒の充填層としては、単純固定床型／ラジアルフロー型等の形式のものをあげることができ、充填操作の容易さの観点から単純固定床型が好ましい。 Examples of the packed bed of the solid hydrogenation catalyst include simple fixed bed type / radial flow type, and the simple fixed bed type is preferable from the viewpoint of easy filling operation.
水添するオレフィンとしては、エチレン、プロピレン等の脂肪族系不飽和炭化水素、またスチレン等の芳香族系不飽和炭化水素をあげることができる。スチレン類としては、スチレン、α―メチルスチレン等をあげることができる。側鎖にオレフィン部分を有する芳香族化合物の場合は、側鎖のオレフィン部分を水素添加し、芳香族環は水素添加されない。 Examples of the olefin to be hydrogenated include aliphatic unsaturated hydrocarbons such as ethylene and propylene, and aromatic unsaturated hydrocarbons such as styrene. Examples of styrenes include styrene and α-methylstyrene. In the case of an aromatic compound having an olefin moiety in the side chain, the olefin moiety in the side chain is hydrogenated and the aromatic ring is not hydrogenated.
本発明においては、固体水添触媒の充填層にオレフィンを含有する液と水素を含むガスとの液ガス混合物をガス空塔速度３ｃｍ／ｓｅｃ以上の流速で通過させる。液ガス混合物の流れ方向は、反応流体を反応器下部より供給し、反応生成物を反応器上部より抜き出すアップフローまたはその逆方向であるダウンフローのいずれでも良い。 In the present invention, a liquid gas mixture of a liquid containing olefin and a gas containing hydrogen is passed through the packed bed of the solid hydrogenation catalyst at a gas superficial velocity of 3 cm / sec or more. The flow direction of the liquid gas mixture may be either an up flow in which a reaction fluid is supplied from the lower part of the reactor and a reaction product is withdrawn from the upper part of the reactor, or a down flow in the opposite direction.
オレフィンと水素の比率は、通常１．０〜３０．０倍モル数である。ガス空塔速度は３ｃｍ／ｓｅｃ以上であり、好ましくは３．５ｃｍ／ｓｅｃ以上である。ガス空塔速度が低すぎるとオレフィンの水添反応速度が速いため、気相中の水素が液に溶解する速度が律速になり、見かけの反応速度の低下、すなわち、充填層単位あたりの反応量が低下する。更に、オレフィンの水添反応速度の低下により、オレフィンの２量化やそれ以上の重合物の生成によるタール化反応が起こり、収率が低下する。 The ratio of olefin to hydrogen is usually 1.0 to 30.0 times the number of moles. The gas superficial velocity is 3 cm / sec or more, preferably 3.5 cm / sec or more. If the gas superficial velocity is too low, the hydrogenation reaction rate of the olefin is fast, so the rate at which hydrogen in the gas phase dissolves in the liquid becomes the rate limiting, and the apparent reaction rate decreases, that is, the reaction amount per packed bed unit Decreases. Furthermore, a decrease in the hydrogenation reaction rate of the olefin causes a tarring reaction due to the dimerization of the olefin and the generation of a polymer beyond that, and the yield decreases.
ガス空塔速度は３ｃｍ／ｓｅｃ以上、１０ｃｍ／ｓｅｃ以下であることが好ましい。ガス空塔速度が高すぎると、触媒同士の摩擦により摩耗粉が発生し、充填層の圧力損失が増加する場合がある。低すぎると生産性が低くて実用的でない。ガス空塔速度は、下記式（１）により算出できる。
(ガス空塔速度)＝（実ガス体積流量）／（反応器断面積） （式１）
The gas superficial velocity is preferably 3 cm / sec or more and 10 cm / sec or less. If the gas superficial velocity is too high, abrasion powder is generated due to friction between the catalysts, and the pressure loss of the packed bed may increase. If it is too low, the productivity is low and not practical. The gas superficial velocity can be calculated by the following formula (1).
(Gas superficial velocity) = (Actual gas volume flow rate) / (Reactor cross section) (Equation 1)
本発明の最大の特徴は、充填触媒層中に含有される直径１ｍｍ以下の触媒微紛の割合が５重量％以下である触媒充填層を使用する点にある。好ましくは、直径１ｍｍ以下の触媒微紛の割合が３重量％以下である充填層を使用する。該触媒微紛の割合が多すぎると充填触媒層の圧力損失が増加する。 The greatest feature of the present invention is that a catalyst packed bed in which the proportion of catalyst fine particles having a diameter of 1 mm or less contained in the packed catalyst layer is 5 wt% or less is used. Preferably, a packed bed in which the proportion of catalyst fines having a diameter of 1 mm or less is 3% by weight or less is used. If the proportion of the catalyst fines is too large, the pressure loss of the packed catalyst layer increases.
以下、実施例により本発明を説明するが、本発明はこれらの実施例により限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not limited by these Examples.
以下の実施例、比較例において、直径１ｍｍ以下の触媒微紛の割合を下記の方法により測定した。充填触媒の代表サンプルを用意し、開口幅が１ｍｍである金属製篩に投入させ、手動又は自動振動器等により、一定時間振動させた後、篩を通過したものを触媒微紛とし、通過触媒微紛量を秤量して全投入サンプル量から重量％を算出した。 In the following examples and comparative examples, the proportion of catalyst fine particles having a diameter of 1 mm or less was measured by the following method. Prepare a representative sample of the packed catalyst, put it into a metal sieve with an opening width of 1 mm, vibrate for a certain period of time with a manual or automatic vibrator, etc., and then pass through the sieve as catalyst fines. The amount of fine powder was weighed, and the weight percentage was calculated from the total amount of input samples.
実施例１
直径６８ｍｍの流通テスト管の入口部及び出口部に圧力計を設置し、直径1ｍｍ以下の微粉の含有量が０．１８重量％である固体触媒を流通テスト管に充填して、液を０．６ｃｍ／sec、ガスを３．９ｃｍ／ｓｅｃで流通させ、固体触媒充填層部分の差圧を実測した。流通テスト管に液及びガスを流通させると触媒充填層の差圧は約１３ｋＰａ／ｍ(充填層相当)であった。
Example 1
Pressure gauges were installed at the inlet and outlet of a flow test tube with a diameter of 68 mm, a solid catalyst having a fine powder content of 1 mm or less in diameter of 0.18% by weight was filled into the flow test tube, The differential pressure of the solid catalyst packed bed portion was measured by flowing 6 cm / sec and gas at 3.9 cm / sec. When liquid and gas were passed through the flow test tube, the differential pressure in the catalyst packed bed was about 13 kPa / m (corresponding to packed bed).
実施例２
直径1ｍｍ以下の微粉の含有量が２．０重量％である触媒を流通テスト管に充填した以外は、実施例１と同様にして、流通テスト管に充填し液及びガスを流通させた。触媒充填層の差圧は約１２ｋＰａ／ｍ(充填層相当)であった。
Example 2
The flow test tube was filled and the liquid and gas were circulated in the same manner as in Example 1 except that the flow test tube was filled with a catalyst having a fine powder content of 1 mm or less in diameter of 2.0% by weight. The differential pressure of the catalyst packed bed was about 12 kPa / m (corresponding to packed bed).
比較例１
直径1ｍｍ以下の微粉の含有量が５．２重量％である触媒を流通テスト管に充填した以外は、実施例１と同様にして、流通テスト管に充填し液及びガスを流通させた。触媒充填層の差圧は増大し、ガス流通規定量３．９ｃｍ／ｓｅｃを流通することが不可能であった。ガス流通１．８ｃｍ／ｓｅｃの時の、触媒充填層の差圧は約２２ｋＰａ／ｍ(充填層相当)であった。
Comparative Example 1
A flow test tube was filled and liquid and gas were circulated in the same manner as in Example 1 except that the flow test tube was filled with a catalyst having a fine powder content of 1 mm or less in diameter of 5.2% by weight. The differential pressure in the catalyst packed bed increased, and it was impossible to circulate the gas flow regulation amount of 3.9 cm / sec. When the gas flow was 1.8 cm / sec, the differential pressure in the catalyst packed bed was about 22 kPa / m (corresponding to packed bed).
比較例２
直径1ｍｍ以下の微粉の含有量が６．７重量％である触媒を流通テスト管に充填した以外は、実施例１と同様にして、液及びガスを流通させた。触媒充填層の差圧は増大し、ガス流通規定量３．９ｃｍ／ｓｅｃを流通することが不可能であった。ガス流通０．９ｃｍ／ｓｅｃの時の、触媒充填層の差圧は約４３ｋＰａ／ｍ(充填層相当)であった。
Comparative Example 2
The liquid and the gas were circulated in the same manner as in Example 1 except that the catalyst having a fine powder having a diameter of 1 mm or less having a content of 6.7% by weight was filled in the flow test tube. The differential pressure in the catalyst packed bed increased, and it was impossible to circulate the gas flow regulation amount of 3.9 cm / sec. When the gas flow was 0.9 cm / sec, the differential pressure in the catalyst packed bed was about 43 kPa / m (corresponding to packed bed).
実施例３
反応器に直径１．５ｍｍ、長さ６ｍｍ程度の大きさの押出成型触媒(円柱状)を充填した。直径1ｍｍ以下の微粉の含有量は０．３３重量％であった。反応器下部よりα−メチルスチレンを含有するクメン及び水素を含むガスを通過させ、水添反応させることによりα−メチルスチレンをクメンに転化させた。液空塔速度は０．５ｃｍ／ｓｅｃ、ガス空塔速度は３．８ｃｍ／ｓｅｃであった。このときの触媒充填層の差圧は約１３ｋＰａ／ｍ(充填層相当)であり、触媒層の差圧は問題ないレベルであった。
Example 3
The reactor was packed with an extrusion-molded catalyst (cylindrical shape) having a diameter of about 1.5 mm and a length of about 6 mm. The content of fine powder having a diameter of 1 mm or less was 0.33% by weight. Α-methylstyrene was converted to cumene by passing a gas containing cumene and hydrogen containing α-methylstyrene from the lower part of the reactor, and hydrogenating the gas. The liquid superficial velocity was 0.5 cm / sec, and the gas superficial velocity was 3.8 cm / sec. At this time, the differential pressure of the catalyst packed bed was about 13 kPa / m (corresponding to the packed bed), and the differential pressure of the catalyst bed was at a level with no problem.
以上の実施例、比較例から次のことが分かる。実施例１、２および比較例１、２から、触媒充填層中に含有する直径１ｍｍ以下の触媒微紛の割合が５重量％より大きい場合は、触媒充填層の差圧は増大し、ガス空塔速度３．０ｃｍ／ｓｅｃ以上の液ガス混合物を通過させることが実用上不可能であることがわかった。また、実用的な反応器および微粉が０．３３重量％の触媒を用いた実施例３の反応例では、触媒層の差圧は問題ないレベルであり、反応は円滑に行われた。 From the above examples and comparative examples, the following can be understood. From Examples 1 and 2 and Comparative Examples 1 and 2, when the proportion of catalyst fine particles having a diameter of 1 mm or less contained in the catalyst packed bed is larger than 5% by weight, the differential pressure of the catalyst packed bed increases and the gas empty It was found that it was practically impossible to pass a liquid gas mixture having a tower speed of 3.0 cm / sec or more. Further, in the reaction example of Example 3 using a practical reactor and a catalyst having a fine powder of 0.33% by weight, the differential pressure of the catalyst layer was at a level that was not a problem, and the reaction was performed smoothly.
Claims (3)
The olefin hydrogenation method according to claim 1 or 2, wherein the olefin is styrene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006082764A JP2007254413A (en) | 2006-03-24 | 2006-03-24 | Method for hydrogenation of olefin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006082764A JP2007254413A (en) | 2006-03-24 | 2006-03-24 | Method for hydrogenation of olefin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2007254413A true JP2007254413A (en) | 2007-10-04 |
Family
ID=38629008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006082764A Pending JP2007254413A (en) | 2006-03-24 | 2006-03-24 | Method for hydrogenation of olefin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2007254413A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014084285A (en) * | 2012-10-22 | 2014-05-12 | Sumitomo Seika Chem Co Ltd | Process for producing paraffin |
| CN106607027A (en) * | 2015-10-22 | 2017-05-03 | 财团法人工业技术研究院 | Catalyst and process for selectively hydrogenating copolymers |
| CN112121793A (en) * | 2020-09-17 | 2020-12-25 | 万华化学集团股份有限公司 | Catalyst for preparing citronellal by citral hydrogenation, preparation method of catalyst, and method for preparing citronellal by citral hydrogenation |
-
2006
- 2006-03-24 JP JP2006082764A patent/JP2007254413A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014084285A (en) * | 2012-10-22 | 2014-05-12 | Sumitomo Seika Chem Co Ltd | Process for producing paraffin |
| CN106607027A (en) * | 2015-10-22 | 2017-05-03 | 财团法人工业技术研究院 | Catalyst and process for selectively hydrogenating copolymers |
| CN112121793A (en) * | 2020-09-17 | 2020-12-25 | 万华化学集团股份有限公司 | Catalyst for preparing citronellal by citral hydrogenation, preparation method of catalyst, and method for preparing citronellal by citral hydrogenation |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Crespo-Quesada et al. | Modern trends in catalyst and process design for alkyne hydrogenations | |
| US9738835B2 (en) | Process for performing a fischer tropsch reaction | |
| CN109070036B (en) | Method for carrying out heterogeneously catalyzed reactions | |
| US9216402B2 (en) | Reactor and catalyst for converting natural gas to organic compounds | |
| AU2004245280B2 (en) | Selective hydrogenation process and catalyst therefor | |
| US9005538B2 (en) | Stacked catalyst bed for Fischer-Tropsch | |
| US20100160462A1 (en) | High-speed stop in a fischer-tropsch process | |
| WO2016130393A1 (en) | Methods for conversion of methane to syngas | |
| JP2007254413A (en) | Method for hydrogenation of olefin | |
| JP2001199917A (en) | METHOD FOR PRODUCING alpha-PHENYLETHYL ALCOHOL | |
| JP2020534262A (en) | A method for producing methyl methacrylate by oxidative esterification using a heterogeneous catalyst | |
| SE442992B (en) | WAY TO BRING CARBON MONOXIDE TO RESEARCH WHETHER WITH AN INERT LIQUID PHASE LIKE DETERGENT | |
| EP2519605B1 (en) | Stacked catalyst bed for fischer-tropsch | |
| RU2014118948A (en) | METHOD FOR HYDRODECLORATION OF LIQUID RAW MATERIAL CONTAINING Dichloroacetic Acid | |
| EA017647B1 (en) | Process of catalytic partial oxidation of hydrocarbons into synthesis gas | |
| AU2009327203A1 (en) | High-speed stop in a Fischer-Tropsch process | |
| JP2008303213A (en) | Method for forming tetrahydrogeranylacetone | |
| RU2385857C1 (en) | Method of purifying styrene from phenylacetylene impurities | |
| CN103338865B (en) | Heterogeneous catalyst and its use thereof | |
| JP4552378B2 (en) | Olefin hydrogenation method | |
| JP2009155245A (en) | Method for producing cumene | |
| JP2007099729A (en) | METHOD FOR PRODUCING alpha-METHYLSTYRENE OR CUMENE | |
| CN1279142C (en) | Catalyst utilized to prepare hydrocarbon from synthesis gas and its preparation method | |
| EP2125678A1 (en) | Process for the hydrogenation of alkylaryl ketones | |
| JP2013082677A (en) | Multi-tubular fixed bed reactor for production of propylene oxide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080201 |
|
| RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080515 |