JPS6332338B2 - - Google Patents
Info
- Publication number
- JPS6332338B2 JPS6332338B2 JP3585783A JP3585783A JPS6332338B2 JP S6332338 B2 JPS6332338 B2 JP S6332338B2 JP 3585783 A JP3585783 A JP 3585783A JP 3585783 A JP3585783 A JP 3585783A JP S6332338 B2 JPS6332338 B2 JP S6332338B2
- Authority
- JP
- Japan
- Prior art keywords
- butene
- metal
- oxygen
- containing gas
- oxidative dehydrogenation
- 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.)
- Expired
Links
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 45
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 41
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 18
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910044991 metal oxide Inorganic materials 0.000 claims description 14
- 150000004706 metal oxides Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 229910052714 tellurium Inorganic materials 0.000 claims description 3
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 150000002739 metals Chemical class 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 241000605477 Borya Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
（目的及び背景）
この発明は分子状酸素を供給することなく１−
ブテン又は２−ブテンを金属酸化物に接触させ金
属酸化物の結合酸素による酸化脱水素によりブタ
ジエンを製造する方法に関するものである。
ブタン又はブテンからブタジエンを製造する方
法としては、酸素の不存在下ブタン又はブテンを
触媒に接触させて脱水素を行う方法や、酸素の存
在下ブテンを触媒に接触させて酸化脱水素を行う
方法が知られているが、前者は遊離炭素の生成が
多く、対策として水蒸気を添加し、更に頻繁に触
媒再生を行わなければならず、また後者は各種含
酸素炭化水素化合物類を副生するので精製工程が
複雑になるという欠点がある。
またブテンの酸化脱水素によるブタジエン製造
における各種触媒（金属酸化物）の反応特性を調
べるための一手段としてヘリウムガス中の金属酸
化物、具体的にはMo−Bi、Mo−Sb、Mo−As
に高温で接触させる方法を採つたことが報告され
ている（越後谷ほか、日本化学会昭和53年年会）。
これはブテンが酸化脱水素されブタジエンが生成
されることをしめしてはいるが、その実用化のた
めの具体的な方法についてはなんら提示されてい
ない。
本発明は金属酸化物の結合酸素による１−ブテ
ン又は２−ブテンの酸化脱水素を行うものであ
る。この反応においては金属酸化物は還元され金
属又はその低次酸化物になる性質を利用するもの
であり、この反応を効果的に続行させるには金属
又はその低次酸化物を空気等の酸素含有ガスで酸
化し繰返し使用して金属酸化物の結合酸素による
１−ブテン又は２−ブテンの酸化脱水素反応のみ
を行わせることを必要とする。
本発明者等はかかる着想に基いて試験を行つた
ところ遊離炭素の生成のない点は予想した通りで
あつたが副反応としてCO及びCO2がかなり生成
することが認められた。本発明者等はこの理由に
ついて追求した結果、酸素含有ガスで酸化焼成し
た後、水蒸気又は水蒸気含有ガスで処理すること
によつて副反応によるCO及びCO2の生成を減少
させられることを見出し本発明を完成するに至つ
たものである。
（構成及び効果）
本発明のブタジエン製造法は、１−ブテン又は
２−ブテンをビスマス、スズ及びテルルからなる
群から選ばれる金属の酸化物に接触させ上記金属
の酸化物の結合酸素による酸化脱水素によりブタ
ジエンを製造し、同時に生成した金属及び／又は
その低次酸化物を酸素含有ガスにより酸化し、次
いで水蒸気又は水蒸気含有ガスで処理した後再び
１−ブテン又は２−ブテンと接触させ酸化脱水素
に使用することによりなる。
即ち本発明は、１−ブテン又は２−ブテンの酸
化脱水素においてビスマス、スズ及びテルルから
なる群から選ばれる金属の酸化物を酸素キヤリヤ
ーとして使用すること、この使用により生成した
金属及び／又はその低次酸化物を酸素含有ガスに
より酸化すること及び使用する金属酸化物を使用
前に水蒸気又は水蒸気含有ガスで処理する点に特
色がある。
酸素キヤリヤーは上記金属の酸化物又はその混
合物そのもの、あるいはそれらを多孔性担体例え
ばアルミナ、シリカアルミナ、チタニヤ、マグネ
シヤ、ボリヤなどに担持した形や稀釈剤と混合し
成形した形で使用され、流動床（移動床）反応で
も固定床反応でもよい。１−ブテン又は２−ブテ
ンの酸化脱水素反応、金属やその低次酸化物の酸
化反応及び金属酸化物の水蒸気又は水蒸気含有ガ
スによる処理をすべて流動床（移動床）で行い金
属又はその酸化物をこの間で循環させれば、１−
ブテン又は２−ブテンの酸化脱水素によるブタジ
エンの生成を完全に連続して行うことができる。
固定床の場合は反応塔を２基併設し、それぞれを
交互に１−ブテン又は２−ブテンの酸化脱水素反
応用及び金属又はその低次酸化物の酸化と水蒸気
又は水蒸気含有ガス処理用にあてて切替操作を行
えばブタジエンの生成を実質的に連続して行うこ
とができる。
金属酸化物はその全部が完全にその金属の最高
原子価の酸化物である必要はなく、また金属の低
次酸化物はその全部が完全にその金属の最低原子
価の酸化物である必要はない。要するに反応前後
において結合酸素の増減がある状態で使用すれば
よいのであつて、どのような条件で使用するかは
１−ブテン又は２−ブテンの反応率、ブタジエン
の選択率、装置容積及び必要エネルギー等の因子
を総合的に判断して決定すればよい。
又原料は１−ブテン又は２−ブテンの単独ガス
に限られるものではなく、それらの混合ガスでも
よい。
水蒸気は水蒸気そのものに限らず水蒸気含有ガ
スであつてもよい。例えば水蒸気に窒素などの不
活性ガスを混合したものや燃焼排ガスなども可能
である。
酸素キヤリヤーとして使用する金属の種類にも
よるが、１−ブテン又は２−ブテンの酸化脱水素
によるブタジエンの生成反応温度は約300〜600
℃、好ましくは350〜550℃、反応圧力は常圧程度
である。
金属やその低次酸化物を酸素含有ガス（空気）
で速やかに酸化焼成する為にはブタジエン生成反
応の温度よりも高めである方がよく、金属の種類
にもよるが、通常400〜700℃で行う。前段の酸化
焼成に続いてそれよりも温度の低い水蒸気または
水蒸気含有ガスを送入すれば、吸着酸素を除去す
る働きをすると共に金属酸化物の温度を下げて次
段の１−ブテン又は２−ブテンの酸化脱水素反応
に適した温度にする働きもする。
水蒸気または水蒸気含有ガス処理時間あるいは
送入量は酸化脱水素反応における副生物の減少の
程度を見て実験的に定めればよい。さらに酸化脱
水素反応時に水蒸気を供給することは副生物の生
成を抑制する効果がある。
実施例 １
酸素キヤリヤーとしてビスマスの酸化物を使用
した。γ−アルミナに硝酸ビスマス水溶液を含浸
させ、乾燥させたものを空気を流通しつつ600℃
で３時間焼成し、γ−アルミナ担持Bi2O3とし
た。ステンレス製Ｕ字形の反応管（酸素キヤリヤ
ー充填部の内径10ミリ）にγ−アルミナに担持さ
せたBi2O32mlを充填し、反応管を温度制御器付
の砂流動浴槽（電熱加熱式）中に設置し加熱して
温度設定し、ヘリウムガスをキヤリヤーガスとし
て水蒸気を、水蒸気／酸素キヤリヤー＝２（モル
当量／モル当量）となる分量だけ導入した。その
後１−ブテン（純度99％以上）を導入した。反応
管出口ガスはそのままガスクロマトグラフイーに
供給し生成物および未反応ガスの分析を行つた。
同様にしてγ−アルミナに担持したSnO及び
TeO2についても同様な方法で試験を行つた。結
果を第１表に示す。
いずれの場合も酸化脱水素反応副生物はCOお
よびCO2で、その他はガスクロマトグラフイーに
よる検知限界以下であつた。
(Purpose and Background) This invention provides 1-
The present invention relates to a method for producing butadiene by contacting butene or 2-butene with a metal oxide and oxidative dehydrogenation using the bound oxygen of the metal oxide. Methods for producing butadiene from butane or butene include a method in which dehydrogenation is carried out by bringing butane or butene into contact with a catalyst in the absence of oxygen, and a method in which oxidative dehydrogenation is carried out by bringing butene into contact with a catalyst in the presence of oxygen. However, the former produces a large amount of free carbon, requiring the addition of steam and frequent catalyst regeneration as a countermeasure, and the latter produces various oxygen-containing hydrocarbon compounds as by-products. The disadvantage is that the purification process is complicated. In addition, metal oxides in helium gas, specifically Mo-Bi, Mo-Sb, Mo-As, are used as a means to investigate the reaction characteristics of various catalysts (metal oxides) in the production of butadiene by oxidative dehydrogenation of butene.
It has been reported that a method of contacting at high temperature was adopted (Echigotani et al., 1978 Annual Meeting of the Chemical Society of Japan).
This indicates that butadiene is produced by oxidative dehydrogenation of butene, but no specific method for its practical application has been proposed. The present invention performs oxidative dehydrogenation of 1-butene or 2-butene using bound oxygen of a metal oxide. This reaction utilizes the property of metal oxides being reduced to become metals or their lower oxides, and in order to continue this reaction effectively, the metals or their lower oxides are exposed to oxygen-containing air such as air. It is necessary to oxidize with gas and use repeatedly to perform only the oxidative dehydrogenation reaction of 1-butene or 2-butene by the bound oxygen of the metal oxide. The present inventors conducted tests based on this idea, and found that, as expected, no free carbon was produced, but a considerable amount of CO and CO 2 were produced as side reactions. As a result of investigating the reason for this, the present inventors discovered that the production of CO and CO 2 due to side reactions can be reduced by oxidizing and firing with oxygen-containing gas and then treating with steam or steam-containing gas. This led to the completion of the invention. (Structure and Effects) The method for producing butadiene of the present invention involves contacting 1-butene or 2-butene with an oxide of a metal selected from the group consisting of bismuth, tin, and tellurium, and oxidizing and dehydrating the metal oxide using bound oxygen. At the same time, the metal and/or its lower oxides are oxidized with oxygen-containing gas, and then treated with steam or steam-containing gas, and then brought into contact with 1-butene or 2-butene again for oxidative dehydration. By using it naturally. That is, the present invention provides the use of an oxide of a metal selected from the group consisting of bismuth, tin and tellurium as an oxygen carrier in the oxidative dehydrogenation of 1-butene or 2-butene, and the metal produced by this use and/or its It is characterized by oxidizing lower oxides with an oxygen-containing gas and treating the metal oxides used with steam or steam-containing gas before use. Oxygen carriers are used in the form of oxides of the above metals or mixtures thereof, supported on porous carriers such as alumina, silica-alumina, titania, magnesia, borya, etc., or mixed with a diluent and molded. It may be a (moving bed) reaction or a fixed bed reaction. The oxidative dehydrogenation reaction of 1-butene or 2-butene, the oxidation reaction of metals and their lower oxides, and the treatment of metal oxides with steam or steam-containing gas are all carried out in a fluidized bed (moving bed) to produce metals or their oxides. If you circulate between this, 1-
The production of butadiene by oxidative dehydrogenation of butene or 2-butene can be carried out completely continuously.
In the case of a fixed bed, two reaction towers are installed, and each is used alternately for the oxidative dehydrogenation reaction of 1-butene or 2-butene, the oxidation of metals or lower oxides thereof, and the treatment of steam or steam-containing gases. By performing a switching operation, butadiene can be produced substantially continuously. Metal oxides do not need to be entirely the highest valence oxide of the metal, and lower oxides of metals do not need to be entirely the lowest valence oxide of the metal. do not have. In short, it can be used with the amount of bound oxygen increasing or decreasing before and after the reaction, and the conditions under which it is used depend on the reaction rate of 1-butene or 2-butene, the selectivity of butadiene, the equipment volume, and the required energy. It may be determined by comprehensively considering factors such as. Further, the raw material is not limited to a single gas of 1-butene or 2-butene, but may be a mixed gas thereof. The water vapor is not limited to water vapor itself, and may be a water vapor-containing gas. For example, a mixture of water vapor and an inert gas such as nitrogen or combustion exhaust gas may also be used. Although it depends on the type of metal used as the oxygen carrier, the reaction temperature for producing butadiene by oxidative dehydrogenation of 1-butene or 2-butene is approximately 300-600℃.
℃, preferably 350 to 550℃, and the reaction pressure is about normal pressure. Oxygen-containing gas (air) for metals and their lower oxides
In order to quickly oxidize and fire, it is better to set the temperature higher than the butadiene production reaction temperature, and it is usually carried out at 400 to 700°C, depending on the type of metal. If steam or steam-containing gas at a lower temperature is introduced following the oxidation firing in the first stage, it will work to remove adsorbed oxygen and lower the temperature of the metal oxide to produce 1-butene or 2-butene in the next stage. It also works to maintain the temperature suitable for the oxidative dehydrogenation reaction of butene. The treatment time or feeding amount of water vapor or water vapor-containing gas may be determined experimentally based on the degree of reduction of by-products in the oxidative dehydrogenation reaction. Furthermore, supplying steam during the oxidative dehydrogenation reaction has the effect of suppressing the production of by-products. Example 1 Bismuth oxide was used as the oxygen carrier. γ-Alumina was impregnated with an aqueous solution of bismuth nitrate and dried at 600°C while circulating air.
The mixture was fired for 3 hours to obtain γ-alumina-supported Bi 2 O 3 . A stainless steel U-shaped reaction tube (inner diameter of the oxygen carrier filling part: 10 mm) was filled with 2 ml of Bi 2 O 3 supported on γ-alumina, and the reaction tube was placed in a sand flow bath with a temperature controller (electric heating type). The reactor was placed inside the tank and heated to set the temperature, and water vapor was introduced in an amount such that water vapor/oxygen carrier=2 (mole equivalent/mole equivalent) using helium gas as a carrier gas. Thereafter, 1-butene (purity of 99% or more) was introduced. The reaction tube outlet gas was directly supplied to gas chromatography to analyze products and unreacted gas. Similarly, SnO supported on γ-alumina and
TeO 2 was also tested in a similar manner. The results are shown in Table 1. In all cases, the by-products of the oxidative dehydrogenation reaction were CO and CO 2 , and the rest were below the detection limit by gas chromatography.
【表】
実施例 ２
実施例１と同一の装置を使用し、γ−アルミナ
に担持させたBi2O3を酸素キヤリヤーとして、２
−ブテンからのブタジエン生成について実施例１
と同様な方法で試験を行つた。なお２−ブテン／
酸素キヤリヤーは、6.9（モル当量／モル当量）と
した。結果を第２表に示す。[Table] Example 2 Using the same equipment as in Example 1, Bi 2 O 3 supported on γ-alumina was used as an oxygen carrier.
- Example 1 for butadiene production from butene
The test was conducted in a similar manner. In addition, 2-butene/
The oxygen carrier was 6.9 (mole equivalent/mole equivalent). The results are shown in Table 2.
【表】
（効果）
１−ブテン又は２−ブテンから高選択率でブタ
ジエンを製造することができる。[Table] (Effects) Butadiene can be produced from 1-butene or 2-butene with high selectivity.
Claims (1)
ズ及びテルルからなる群から選ばれる金属の酸化
物に接触させ上記金属の酸化物の結合酸素による
酸化脱水素によりブタジエンを製造し、同時に生
成した金属及び／又はその低次酸化物を酸素含有
ガスにより酸化し、次いで水蒸気又は水蒸気含有
ガスで処理した後再び１−ブテン又は２−ブテン
と接触させ酸化脱水素に使用することよりなるブ
タジエンの製造法。 ２ 金属の酸化物が担体に担持した固体粒子及
び／又は稀釈剤と混合し成形した固体粒子である
特許請求の範囲第１項記載の方法。 ３ 酸素含有ガスによる金属及び／又はその低次
酸化物の酸化を酸化脱水素の反応温度より高い温
度で行う特許請求の範囲第１項記載の方法。 ４ １−ブテン又は２−ブテンを金属の酸化物に
接触させる工程に水蒸気又は水蒸気含有ガスを供
給する特許請求の範囲第１項記載の方法。[Claims] 1. Butadiene is produced by contacting 1-butene or 2-butene with an oxide of a metal selected from the group consisting of bismuth, tin, and tellurium, and oxidative dehydrogenation using the bound oxygen of the oxide of the metal. At the same time, the metal and/or its lower oxides are oxidized with an oxygen-containing gas, then treated with steam or a steam-containing gas, and then brought into contact with 1-butene or 2-butene again for use in oxidative dehydrogenation. A method for producing butadiene. 2. The method according to claim 1, wherein the metal oxide is solid particles supported on a carrier and/or solid particles formed by mixing with a diluent. 3. The method according to claim 1, wherein the oxidation of the metal and/or its lower oxide with an oxygen-containing gas is carried out at a temperature higher than the reaction temperature of oxidative dehydrogenation. 4. The method according to claim 1, wherein water vapor or a water vapor-containing gas is supplied to the step of bringing 1-butene or 2-butene into contact with a metal oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3585783A JPS59161324A (en) | 1983-03-07 | 1983-03-07 | Preparation of butadiene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3585783A JPS59161324A (en) | 1983-03-07 | 1983-03-07 | Preparation of butadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59161324A JPS59161324A (en) | 1984-09-12 |
| JPS6332338B2 true JPS6332338B2 (en) | 1988-06-29 |
Family
ID=12453653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3585783A Granted JPS59161324A (en) | 1983-03-07 | 1983-03-07 | Preparation of butadiene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59161324A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0296887U (en) * | 1989-01-18 | 1990-08-01 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS606625A (en) * | 1983-06-25 | 1985-01-14 | Jgc Corp | Treatment of mixed butene |
| JPH07112988B2 (en) * | 1986-09-19 | 1995-12-06 | 日揮株式会社 | Solid oxygen carrier, process for its production and method of using solid oxygen carrier |
| JPH04102805U (en) * | 1991-02-14 | 1992-09-04 | 富泰 本多 | composite board |
| JP6300280B2 (en) * | 2015-03-26 | 2018-03-28 | Ｊｘｔｇエネルギー株式会社 | Method for producing conjugated diene |
-
1983
- 1983-03-07 JP JP3585783A patent/JPS59161324A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0296887U (en) * | 1989-01-18 | 1990-08-01 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59161324A (en) | 1984-09-12 |
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