JPH0222736B2 - - Google Patents
Info
- Publication number
- JPH0222736B2 JPH0222736B2 JP57169157A JP16915782A JPH0222736B2 JP H0222736 B2 JPH0222736 B2 JP H0222736B2 JP 57169157 A JP57169157 A JP 57169157A JP 16915782 A JP16915782 A JP 16915782A JP H0222736 B2 JPH0222736 B2 JP H0222736B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon monoxide
- acetylene
- ethylene
- palladium catalyst
- hydrogenation
- 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 - Lifetime
Links
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)
Description
【発明の詳細な説明】
本発明は、アセチレンの選択的水添方法に関す
る。更に詳しくは、エチレンを主成分とする混合
ガス中に微量含まれるアセチレンの選択的水添方
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for selective hydrogenation of acetylene. More specifically, the present invention relates to a method for selectively hydrogenating acetylene contained in a trace amount in a mixed gas containing ethylene as a main component.
ポリエチレン樹脂の製造原料として用いられる
エチレン中に含有される不純物としてのアセチレ
ンの許容限界は、通常モル換算で約10ppmであ
る。ところで、エチレンは通常ナフサ、エタン、
ブタンなどを熱分解した後、蒸留による分離法で
エチレン留分が取得されるが、エチレン留分中の
熱分解時に生成したアセチレン含有量を10ppm以
下とすることは、蒸留分離法だけでは不可能であ
る。 The permissible limit for acetylene as an impurity contained in ethylene used as a raw material for producing polyethylene resin is usually about 10 ppm on a molar basis. By the way, ethylene is usually used in naphtha, ethane,
After thermally decomposing butane, etc., the ethylene fraction is obtained using a separation method using distillation, but it is impossible to reduce the acetylene content generated during thermal decomposition in the ethylene fraction to 10 ppm or less using the distillation separation method alone. It is.
従つて、蒸留分離法以外の手段によつてアセチ
レンを除去する必要が生じ、例えば米国特許第
3308180号明細書には、エチレンを主成分とする
混合ガス中に含まれる0.5〜１％のアセチレンを
パラジウム触媒を用いて水素で水添する際、混合
ガス中にアセチレン１モルに対して1.5〜５モル
の水素および混合ガスに対して５〜400ppmの一
酸化炭素を存在せしめて、水添を行なうことが提
案されている。 Therefore, it becomes necessary to remove acetylene by means other than distillative separation, for example, as disclosed in U.S. Pat.
No. 3308180 describes that when 0.5 to 1% acetylene contained in a mixed gas containing ethylene as a main component is hydrogenated with hydrogen using a palladium catalyst, 1.5 to 1% of acetylene is hydrogenated per mole of acetylene in the mixed gas. It has been proposed to carry out the hydrogenation in the presence of 5 to 400 ppm carbon monoxide relative to 5 moles of hydrogen and the gas mixture.
かかるアセチレンの選択的水添方法は、大変す
ぐれた方法ではあるが、この方法をそのまま採用
することができない場合がある。即ち、炭化水素
の熱分解ガスを蒸留分離して、炭素数３以上の重
い留分を除去した、エチレンを含む軽沸点留分中
には、元来エチレンの他に、アセチレンおよびそ
れに対して10倍モル以上の水素などが存在してお
り、この比較的多量に含まれている水素のため
に、前記公知方法をそのまま適用するとアセチレ
ンが水添されるばかりではなく、エチレンもある
程度水添されエタンを生成させる。このことは、
エチレンの損失を意味するばかりではなく、エチ
レンの水素化反応に伴なう発熱により温度の制御
が不可能となり、きわめて危険な状態となり、水
添処理の継続を困難とさせ、結局は所望のアセチ
レンの水添も十分に行なえないという結果をもた
らすことになる。 Although this method of selective hydrogenation of acetylene is a very excellent method, there are cases where this method cannot be adopted as is. That is, in the light boiling point fraction containing ethylene, which is obtained by distilling and separating hydrocarbon thermal decomposition gas and removing heavy fractions having 3 or more carbon atoms, in addition to ethylene, acetylene and 10 More than double the molar amount of hydrogen is present, and due to this relatively large amount of hydrogen, if the above-mentioned known method is applied as is, not only acetylene will be hydrogenated, but also ethylene will be hydrogenated to some extent and ethane will be hydrogenated. to generate. This means that
Not only does this mean a loss of ethylene, but the heat generated by the hydrogenation reaction of ethylene makes it impossible to control the temperature, creating an extremely dangerous situation, making it difficult to continue the hydrogenation process, and ultimately resulting in the loss of desired acetylene. This results in insufficient hydrogenation of the hydrogen.
本発明者らは、このような事態を避け、水添処
理を円滑に進行させる方法について種々検討の結
果、水素化反応に先立つて、用いられるパラジウ
ム触媒を一酸化炭素で処理し、そこに一定量以上
吸着せしめることにより、触媒の選択性をより高
め得ると共に上記の如き問題を一挙に解決し得る
ことを見出した。このことは、前記米国特許明細
書に、水素化反応の前に、触媒上に直接一酸化炭
素を通すこともできるが、この方法はそう有効で
はないという記載（第２欄第60〜65行）と際立つ
て対照的である。 As a result of various studies on how to avoid such a situation and make the hydrogenation process proceed smoothly, the inventors of the present invention discovered that prior to the hydrogenation reaction, the palladium catalyst used was treated with carbon monoxide, and a constant amount of carbon monoxide was added thereto. It has been found that by adsorbing more than a certain amount, the selectivity of the catalyst can be further improved and the above-mentioned problems can be solved all at once. This reflects the fact that the above-mentioned US patent specifies that while it is also possible to pass carbon monoxide directly over the catalyst before the hydrogenation reaction, this method is not very effective (column 2, lines 60-65). ) is in sharp contrast.
従つて、本発明はアセチレンの選択的水添方法
に係り、エチレンを主成分とし、微量のアセチレ
ンおよびそれに対して10倍モル以上の水素を含有
する混合ガスをパラジウムム触媒と一酸化炭素の
存在下で接触せしめ、アセチレンを選択的に水素
化するに際し、水素化反応に先立つて、パラジウ
ム触媒１ｇ当り一酸化炭素が70ml以上（標準状態
換算）吸着されるように、パラジウム触媒を一酸
化炭素で接触処理することを特徴としている。 Therefore, the present invention relates to a method for selective hydrogenation of acetylene, in which a mixed gas containing ethylene as a main component, a trace amount of acetylene, and hydrogen in an amount more than 10 times the mole of acetylene is heated in the presence of a palladium catalyst and carbon monoxide. When selectively hydrogenating acetylene by contacting the catalyst below, prior to the hydrogenation reaction, the palladium catalyst is heated with carbon monoxide so that at least 70 ml of carbon monoxide (converted to standard conditions) is adsorbed per 1 g of the palladium catalyst. It is characterized by contact treatment.
本発明方法の処理対象とされる混合ガスは、エ
チレンを主成分とし、微量（モル換算で約
10000ppm以下）のアセチレンおよびそれに対し
て10倍モル以上、好ましくは10〜100倍モルの水
素を含有するものであつて、これら以外にメタ
ン、エタンなどの飽和炭化水素あるいは一酸化炭
素を含有していてもよい。具体例を挙げると、ナ
フサなどの炭化水素の熱分解ガスを蒸留分離し
て、炭素数３以上の重い留分を除去した、エチレ
ンを主成分として含む軽沸点留分であつて、例え
ば次のような組成を有するものが用いられる。 The mixed gas to be treated by the method of the present invention contains ethylene as its main component, and contains a trace amount (approximately on a molar basis).
10,000 ppm or less) and at least 10 times the mole of acetylene, preferably 10 to 100 times the mole of hydrogen, and in addition to these, contains saturated hydrocarbons such as methane and ethane, or carbon monoxide. It's okay. To give a specific example, it is a light boiling point fraction containing ethylene as a main component obtained by distilling and separating the thermal decomposition gas of a hydrocarbon such as naphtha to remove a heavy fraction having 3 or more carbon atoms. A material having such a composition is used.
エチレン 40〜50モル％
水 素 10〜30モル％
アセチレン 0.3〜0.5モル％
メタン 20〜35モル％
エタン ７〜15モル％
一酸化炭素 300〜500ppm（モル換算）
水素化反応の触媒として用いられるパラジウム
触媒は、アルミナ、シリカなどの担体、好ましく
はアルミナ担体、特に好ましくはα−アルミナ担
体に、約0.01〜0.1重量％の担持量で担持させ、
比表面積約１〜50m2／ｇとして一般に用いられ
る。 Ethylene 40-50 mol% Hydrogen 10-30 mol% Acetylene 0.3-0.5 mol% Methane 20-35 mol% Ethane 7-15 mol% Carbon monoxide 300-500 ppm (mol equivalent) Palladium used as a catalyst for hydrogenation reactions The catalyst is supported on a support such as alumina or silica, preferably an alumina support, particularly preferably an α-alumina support, in a supported amount of about 0.01 to 0.1% by weight,
It is generally used with a specific surface area of about 1 to 50 m 2 /g.
かかるパラジウム触媒の一酸化炭素による接触
処理は、混合ガスの水素化反応に先立つて行われ
る。この接触処理は、種々の態様によつて行なう
ことができるが、例えば水素化反応槽にパラジウ
ム触媒を充填した後、そこに窒素を十分に供給し
て空気を置換した後、窒素の如き不活性ガスの存
在下に、約０〜40℃の温度条件下で、一酸化炭素
の分圧が約５〜100mmHgとなるように一酸化炭素
を供給し、約５〜70時間パラジウム触媒を一酸化
炭素と接触させることにより行われる。 This contact treatment of the palladium catalyst with carbon monoxide is performed prior to the hydrogenation reaction of the mixed gas. This contact treatment can be carried out in various ways, but for example, after filling a hydrogenation reaction tank with a palladium catalyst, supplying sufficient nitrogen thereto to replace the air, and then replacing the air with an inert gas such as nitrogen. Carbon monoxide is supplied in the presence of gas at a temperature of about 0 to 40°C so that the partial pressure of carbon monoxide is about 5 to 100 mmHg, and the palladium catalyst is exposed to carbon monoxide for about 5 to 70 hours. This is done by bringing it into contact with.
この接触処理により、反応槽中の一酸化炭素の
分圧はパラジウム触媒への吸着により低下する
が、その吸着量がパラジウム触媒１ｇ当り70ml以
上、好ましくは70〜150ml（標準状態換算）とな
るように処理される。触媒への一酸化炭素吸着量
がこれより少ないと、アセチレンの選択的な水素
化が困難となり、エチレンの水素化を生ずるなど
反応が好ましくない方向に発展する危険性を有し
ている。 Through this contact treatment, the partial pressure of carbon monoxide in the reaction tank is reduced due to adsorption onto the palladium catalyst, but the adsorption amount should be 70 ml or more, preferably 70 to 150 ml (converted to standard conditions) per 1 g of palladium catalyst. will be processed. If the amount of carbon monoxide adsorbed on the catalyst is less than this, it will be difficult to selectively hydrogenate acetylene, and there is a risk that the reaction will develop in an unfavorable direction, such as hydrogenation of ethylene.
このようにして一酸化炭素と接触処理させたパ
ラジウム触媒を用いての混合ガスの水素化反応
は、一酸化炭素の存在下で行われる。一酸化炭素
は、水素の混在量が多いことに対応して混合ガス
に対し約100〜500ppm（モル換算）存在せしめる
ようにして用いられ、混合ガス中に始めから十分
量存在している場合には新たな添加を必要とはせ
ず、また混合ガス中に一酸化炭素が存在しない場
合には別途供給をする。 The hydrogenation reaction of the mixed gas using the palladium catalyst that has been brought into contact with carbon monoxide in this manner is carried out in the presence of carbon monoxide. Carbon monoxide is used at a concentration of approximately 100 to 500 ppm (in terms of moles) in the mixed gas to accommodate the large amount of hydrogen present in the mixed gas. does not require additional addition, and is supplied separately if carbon monoxide is not present in the gas mixture.
混合ガスの水素化処理は、パラジウム触媒を用
いる水素化の一般的な方法に従つて行われ、具体
的には約40〜90℃、好ましくは約50〜80℃の温度
条件、約10〜50Kg／cm2Ｇの圧力条件および約3000
〜6000／時間の空塔速度（SV）で行われる。 The hydrogenation treatment of the mixed gas is carried out according to the general method of hydrogenation using a palladium catalyst, specifically at a temperature of about 40 to 90°C, preferably about 50 to 80°C, and about 10 to 50 kg. /cm 2 G pressure conditions and approx.
Performed at a superficial velocity (SV) of ~6000/hour.
このような水素化反応により、混合ガス中のア
セチレンは選択的にエチレンに変換され、一方エ
チレンは殆んど水添されないので、それの損失が
みられないばかりではなく、異常の発熱などを伴
うこともないので、反応を円滑に進行させ得ると
いう効果を奏する。 Through such a hydrogenation reaction, acetylene in the mixed gas is selectively converted to ethylene, while ethylene is hardly hydrogenated, so not only is no loss of ethylene observed, but abnormal heat generation is also observed. This has the effect of allowing the reaction to proceed smoothly.
次に、実施例について本発明を説明する。 Next, the present invention will be explained with reference to examples.
実施例
α−アルミナを担体としたパラジウム触媒（パ
ラジウム含有量0.04重量％、比表面積18m2／ｇ）
10トンが充填された容量33m3の反応槽内に窒素ガ
スを供給し、空気を十分に置換した後、約１Kg／
cm2Ｇに加圧した。Example Palladium catalyst using α-alumina as a carrier (palladium content 0.04% by weight, specific surface area 18m 2 /g)
After supplying nitrogen gas into a 33m3 reaction tank filled with 10 tons and thoroughly replacing the air, approximately 1Kg/
Pressure was applied to cm 2 G.
このような状態の反応容器に一酸化炭素0.42Kg
を添加すると、このときの温度30℃で、一酸化炭
素の分圧は15mmHgであつた。かかる一酸化炭
素・窒素混合ガスを循環させつつ、15時間にわた
つて、パラジウム触媒と一酸化炭素との接触を行
なつた。15時間後の一酸化炭素の分圧は約７mm
Hgで、パラジウム１ｇ当りの一酸化炭素の吸着
量は、標準状態換算で90mlであつた。 0.42Kg of carbon monoxide in the reaction vessel in this condition
When added, the partial pressure of carbon monoxide was 15 mmHg at a temperature of 30°C. While circulating the carbon monoxide/nitrogen mixed gas, the palladium catalyst was brought into contact with carbon monoxide for 15 hours. The partial pressure of carbon monoxide after 15 hours is approximately 7 mm.
In terms of Hg, the amount of carbon monoxide adsorbed per gram of palladium was 90 ml in terms of standard conditions.
次いで、この反応容器に、エチレン45モル％、
アセチレン0.5モル％、水素12モル％、一酸化炭
素500ppm、その他メタン、エタンなどを含む混
合ガスを導入した。この際のガスの圧力は30Kg／
cm2Ｇ、反応容器入口温度は15℃、ガス供給量は空
塔速度で6000／時間とした。 Next, 45 mol% of ethylene,
A mixed gas containing 0.5 mol% acetylene, 12 mol% hydrogen, 500 ppm carbon monoxide, and other substances such as methane and ethane was introduced. The gas pressure at this time is 30Kg/
cm 2 G, the reaction vessel inlet temperature was 15° C., and the gas supply rate was 6000/hour in terms of superficial velocity.
その後、反応容器に導入するガスの温度を15
℃／時間の速度で昇温させた処、約３時間後に
は、入口温度60℃、出口温度70℃で温度差は10℃
であり、出口におけるエチレン濃度は45.4モル
％、またアセチレン濃度は5ppmとなり、ここで
ガスの昇温を停止させ、そのままの状態で安定に
アセチレンの選択的水素を行なうことができた。 Then, the temperature of the gas introduced into the reaction vessel was increased to 15
When the temperature was raised at a rate of °C/hour, after about 3 hours, the inlet temperature was 60 °C, the outlet temperature was 70 °C, and the temperature difference was 10 °C.
The ethylene concentration at the outlet was 45.4 mol%, and the acetylene concentration was 5 ppm. At this point, the gas temperature was stopped and selective hydrogenation of acetylene could be carried out stably in that state.
比較例
実施例において、パラジウム触媒に一酸化炭素
を接触させる操作を行なうことなく、混合ガス中
のアセチレンの水添を行なつた処、昇温開始後
1.5時間で入口温度37.5℃、出口温度45℃で温度
差が7.5℃となつたため、昇温速度を10℃／時間
と低下させたが、入口温度40℃のとき出口温度は
53℃と異常に大きくなつた。Comparative Example In the example, when acetylene in the mixed gas was hydrogenated without bringing carbon monoxide into contact with the palladium catalyst, after the temperature started rising.
In 1.5 hours, the temperature difference was 7.5°C with the inlet temperature being 37.5°C and the outlet temperature being 45°C, so the temperature increase rate was reduced to 10°C/hour, but when the inlet temperature was 40°C, the outlet temperature was
It became abnormally large at 53℃.
そこで急拠昇温を停止させたが、出口温度は急
速に上昇し90℃にも達したため、温度制御が不可
能となり、危険な状態となつたので、混合ガスの
供給を停止せざるを得なかつた。 Therefore, we stopped the temperature rise at the sudden point, but the outlet temperature rose rapidly and reached 90℃, making it impossible to control the temperature and creating a dangerous situation, so we had no choice but to stop the supply of the mixed gas. Nakatsuta.
Claims (1)
以上の重い留分を除去した、エチレンを主成分と
し微量のアセチレンおよびそれに対して10倍モル
以上の水素を含有する軽沸点留分混合ガスを、一
酸化炭素の存在下でパラジウム触媒と接触せし
め、アセチレンを選択的に水素化するに際し、水
素化反応に先立つて、パラジウム触媒１ｇ当り一
酸化炭素が70ml以上（標準状態換算）吸着される
ように、パラジウム触媒を一酸化炭素で接触処理
することを特徴とするアセチレンの選択的水添方
法。1 The pyrolysis gas of hydrocarbons is separated by distillation and the number of carbon atoms is 3.
The light-boiling fraction mixed gas containing ethylene as the main component, a trace amount of acetylene, and hydrogen in an amount more than 10 times the mole of ethylene is brought into contact with a palladium catalyst in the presence of carbon monoxide. When selectively hydrogenating acetylene, prior to the hydrogenation reaction, the palladium catalyst is contacted with carbon monoxide so that 70 ml or more of carbon monoxide is adsorbed per gram of the palladium catalyst (converted to standard conditions). A method for selective hydrogenation of acetylene, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57169157A JPS5959634A (en) | 1982-09-27 | 1982-09-27 | Selective hydrogenation of acetylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57169157A JPS5959634A (en) | 1982-09-27 | 1982-09-27 | Selective hydrogenation of acetylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5959634A JPS5959634A (en) | 1984-04-05 |
| JPH0222736B2 true JPH0222736B2 (en) | 1990-05-21 |
Family
ID=15881335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57169157A Granted JPS5959634A (en) | 1982-09-27 | 1982-09-27 | Selective hydrogenation of acetylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5959634A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6948052B2 (en) | 1991-07-08 | 2005-09-20 | Seiko Epson Corporation | High-performance, superscalar-based computer system with out-of-order instruction execution |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6118731A (en) * | 1984-07-06 | 1986-01-27 | Mitsui Petrochem Ind Ltd | Selective hydrogenation of diene and acetylene in hydrocarbons |
| CN1084222C (en) * | 1998-06-10 | 2002-05-08 | 中国石化齐鲁石油化工公司 | Catalyst for selective hydrogenation of diolefin as raw material for alkylation of C4 and preparing method thereof |
| JP4568448B2 (en) * | 2001-03-30 | 2010-10-27 | 出光興産株式会社 | Hydrogen production plant and hydrogen production method |
| US6734130B2 (en) * | 2001-09-07 | 2004-05-11 | Chvron Phillips Chemical Company Lp | Hydrocarbon hydrogenation catalyst composition, a process of treating such catalyst composition, and a process of using such catalyst composition |
| CA2590663A1 (en) * | 2004-12-23 | 2006-06-29 | Solvay (Societe Anonyme) | Process for the manufacture of 1,2-dichloroethane |
| CN112705042A (en) * | 2019-10-25 | 2021-04-27 | 中国石油化工股份有限公司 | Method for removing acetylene and ethylene in natural gas cracking tail gas |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634536A (en) * | 1970-04-27 | 1972-01-11 | Dow Chemical Co | Selective hydrogenation of alkynes |
| JPS5784745A (en) * | 1980-11-14 | 1982-05-27 | Mitsubishi Chem Ind Ltd | Catalyst for removing acetylenic compound in olefin and preparation thereof |
-
1982
- 1982-09-27 JP JP57169157A patent/JPS5959634A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6948052B2 (en) | 1991-07-08 | 2005-09-20 | Seiko Epson Corporation | High-performance, superscalar-based computer system with out-of-order instruction execution |
| US6959375B2 (en) | 1991-07-08 | 2005-10-25 | Seiko Epson Corporation | High-performance, superscalar-based computer system with out-of-order instruction execution |
| US7162610B2 (en) | 1991-07-08 | 2007-01-09 | Seiko Epson Corporation | High-performance, superscalar-based computer system with out-of-order instruction execution |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5959634A (en) | 1984-04-05 |
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