JPH0153718B2 - - Google Patents
Info
- Publication number
- JPH0153718B2 JPH0153718B2 JP56193944A JP19394481A JPH0153718B2 JP H0153718 B2 JPH0153718 B2 JP H0153718B2 JP 56193944 A JP56193944 A JP 56193944A JP 19394481 A JP19394481 A JP 19394481A JP H0153718 B2 JPH0153718 B2 JP H0153718B2
- Authority
- JP
- Japan
- Prior art keywords
- highly unsaturated
- unsaturated hydrocarbons
- hydrocarbons
- reaction
- hydrocarbon
- 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
- 238000000034 method Methods 0.000 claims description 24
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 19
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 7
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- -1 methylalene Chemical class 0.000 description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明はジエン類、アセチレン類のモノエン類
への選択的水素添加法に関するものである。さら
に詳しくは分子内に２以上の二重結合および／ま
たは１以上の三重結合を有する不飽和炭化水素
（以下、高度に不飽和な炭化水素と称す）を含む
炭素数４以上の不飽和炭化水素混合物を触媒の存
在下に水素と接触させて二重結合の異性化を伴わ
ずに高度に不飽和な炭化水素のみを対応する低不
飽和度の炭化水素に転化する方法に関するもので
ある。
高度に不飽和な炭化水素を含む炭素数４以上の
不飽和炭化水素混合物と水素を水素化触媒の存在
下に反応させて高度に不飽和な炭化水素を対応す
る低不飽和度の炭化水素に選択的に水素添加する
方法は一般に公知であり、たとえばブタジエン、
メチルアレン等のジエン類、ジメチルアセチレ
ン、エチルアセチレン、ビニルアセチレン等のア
セチレン類および１―ブテン、２―ブテン、イソ
ブテン等のモノオレフイン類を含有する炭素数４
の不飽和炭化水素混合物を水素とともにパラジウ
ム、白金、ニツケルなどの水素化触媒の存在下に
反応させてジエン類、アセチレン類のみを選択的
に水添する方法は工業的にも採用されている。
しかしながら、これら公知の選択的水素添加方
法においては、２以上の二重結合および１以上の
三重結合など高度に不飽和な結合への選択的水素
添加と同時に二重結合の分子内移動が容易に起こ
り、反応生成物の組成が大きく変つてしまう欠点
があつた。たとえばブタジエン類、ブチン類を含
む炭素数４の不飽和炭化水素の選択的水添反応を
行なつた場合、ブタジエン類、ブチン類からブテ
ンへの選択的水素添加と同時に１―ブテンから２
―ブテンへの異性化が容易に進み、このため反応
生成物中の１―ブテン濃度が大きく減少してしま
う。
１―ブテンはポリオレフイン製造用モノマーと
して重要であり、炭素数４の炭化水素混合物中の
１―ブテンの有効利用をはかる上からも異性化を
伴わないで高度に不飽和な炭化水素のみを選択的
に水添できる方法の出現が強く望まれていた。
本発明者らは、このようなオレフイン類の異性
化を伴わない高度に不飽和な炭化水素の選択的水
添方法について鋭意研究を行ない本発明に到達し
たものである。
すなわち、高度に不飽和な炭化水素を含む炭素
数４以上の低不飽和度の炭化水素をパラジウム触
媒の存在下に水素と接触させて前記の高度に不飽
和な炭化水素を選択的に水素添加する方法におい
て、高度に不飽和な炭化水素を含む炭素数４以上
の低不飽和度の炭化水素混合物に対して0.005〜
５重量％の低級アルコールの存在下に水添反応を
行なうことにより、オレフイン類の異性化をほと
んど伴なうことなく高度に不飽和な炭化水素の選
択的水添反応のみが進行することを見出したもの
である。
本発明方法に用いられる低級アルコールとして
は炭素数１ないし４のアルコールが用いられる。
これらのアルコールとしてメタノール、エタノ
ール、ｎ―プロパノール、ｎ―ブタノール、ｔ―
ブタノール等があるが、好ましくはメタノールが
用いられる。低級アルコールは原料炭化水素混合
物に対して0.005〜５重量％存在させることが必
要であり、好ましくは0.01〜１重量％存在させる
低級アルコールを原料炭化水素混合物に対して
0.005重量％未満存在させても低級アルコールの
添加効果はほとんどなく、また５重量％を超えて
存在させると却つて高度に不飽和な炭化水素の水
添反応が阻害される。オレフイン類の異性化を伴
わずに高度に不飽和な炭化水素を選択的に水添す
る方法として大量のCOガスを含んだH2ガスを用
いて選択的水添反応を行なう方法（特公昭46−
30808号）一段目に気液混相で水添し、二段目は
液相で水添する方法（特公昭52−16082号）ある
いは特殊な触媒を用いる方法（特公昭50−28922
号、ドイツ特許2108276号）等が提案されている。
しかしながら、これらの方法はそれぞれ高価な
COガスを用いる必要があるとか、特殊な触媒を
用いる必要があるとか、またプロセスが煩雑にな
るとかの欠点を有していた。
本発明方法は安価な低級アルコールを少量存在
させるだけでオレフイン類の異性化を伴なうこと
なく高度に不飽和な炭化水素の選択的水素添加反
応のみが進行する方法を提供するものであり、そ
の工業的意義は大きい。
本発明方法に用いられる高度に不飽和な炭化水
素を含む炭素数４以上の低不飽和度の炭化水素混
合物としては、ナフサ等のスチームクラツキング
によつて得られるいわゆるC4留分と呼ばれるブ
タジエン、ブテン、ブタン等からなるC4炭化水
素混合物、そしてこのC4留分からブタジエンの
大部分を抽出によつて取り除いたいわゆるスペン
トBB留分と呼ばれるC4炭化水素混合物、このス
ペントBB留分からさらにイソブチレンを取り除
いた１―ブテンおよび２―ブテンを主成分とする
C4炭化水素混合物、それにイソプレン等のC5炭
化水素類を主成分とする炭化水素混合物などが挙
げられる。これらの炭化水素混合物中に含まれる
高度に不飽和な炭化水素としてはプロパジエン、
メチルアセチレン、１，２―ブタジエン、１，３
―ブタジエン、エチルアセチレン、ビニル―アセ
チレン、１，３―ペンタジエン等がある。
本発明方法には、水添触媒としてパラジウム触
媒が用いられる。パラジウム触媒としてはパラジ
ウムブラツク、パラジウム担持カーボン、パラジ
ウム担持アルミナ等があるが、通常アルミナ等の
担体にパラジウムを0.02〜２重量％担持した触媒
が用いられる。
本発明方法における反応形態は特に限定される
ものではなく、液相、気相あるいはトリクル相の
ような気液混相のいずれもの方法で行なつてもよ
い。また反応条件としては、通常反応温度は−20
〜150℃、反応圧力は常圧〜50気圧の条件下で行
なわれる。
以下に実施例を用いて本発明方法の説明を行な
うが、本発明の範囲はこれらによつて制限を受け
るものではない。
実施例 １
0.1重量％のパラジウムをアルミナに担持した
触媒100mlを内径20mmの垂直に配置した反応管内
に充填し、温度60℃、圧力４気圧の条件下で第１
表の原料欄に記載した組成を持つ炭化水素混合物
に対して0.2重量％のメタノールを添加したもの
を原料として500ｇ／hrの供給速度で反応器に導
入し、また水素ガスを８（N.T.P.換算）／hr
の供給速度で反応器に導入し、選択的水素添加反
応を行なつた。得られた炭化水素生成物の組成は
第１表の生成物欄に示すとおりであつた。
The present invention relates to a method for selectively hydrogenating dienes and acetylenes to monoenes. More specifically, unsaturated hydrocarbons having 4 or more carbon atoms, including unsaturated hydrocarbons having 2 or more double bonds and/or 1 or more triple bonds in the molecule (hereinafter referred to as highly unsaturated hydrocarbons) The present invention relates to a method of contacting a mixture with hydrogen in the presence of a catalyst to convert only highly unsaturated hydrocarbons into corresponding hydrocarbons with a lower degree of unsaturation without isomerization of double bonds. A mixture of unsaturated hydrocarbons with a carbon number of 4 or more, including highly unsaturated hydrocarbons, is reacted with hydrogen in the presence of a hydrogenation catalyst to convert the highly unsaturated hydrocarbons into corresponding hydrocarbons with a low degree of unsaturation. Methods of selective hydrogenation are generally known, such as butadiene,
Carbon number 4 containing dienes such as methylalene, acetylenes such as dimethylacetylene, ethylacetylene, vinylacetylene, and monoolefins such as 1-butene, 2-butene, isobutene, etc.
A method of selectively hydrogenating only dienes and acetylenes by reacting a mixture of unsaturated hydrocarbons with hydrogen in the presence of a hydrogenation catalyst such as palladium, platinum, or nickel has also been adopted industrially. However, in these known selective hydrogenation methods, it is difficult to selectively hydrogenate highly unsaturated bonds, such as two or more double bonds and one or more triple bonds, while at the same time easily moving the double bond into the molecule. This has the disadvantage that the composition of the reaction product changes significantly. For example, when performing a selective hydrogenation reaction of unsaturated hydrocarbons with 4 carbon atoms including butadienes and butynes, the selective hydrogenation reaction from butadienes and butynes to butenes is simultaneously performed.
-Isomerization to butene easily proceeds, resulting in a large decrease in the 1-butene concentration in the reaction product. 1-Butene is important as a monomer for producing polyolefins, and in order to effectively utilize 1-butene in a mixture of hydrocarbons with 4 carbon atoms, highly unsaturated hydrocarbons can be selectively extracted without isomerization. There was a strong desire for a method that could hydrogenate The present inventors have conducted intensive research on a method for selective hydrogenation of highly unsaturated hydrocarbons that does not involve isomerization of such olefins, and have arrived at the present invention. That is, a hydrocarbon with a low degree of unsaturation having 4 or more carbon atoms, including a highly unsaturated hydrocarbon, is brought into contact with hydrogen in the presence of a palladium catalyst to selectively hydrogenate the highly unsaturated hydrocarbon. In the method of
We have discovered that by carrying out the hydrogenation reaction in the presence of 5% by weight of lower alcohols, only the selective hydrogenation reaction of highly unsaturated hydrocarbons proceeds with almost no isomerization of olefins. It is something that The lower alcohol used in the method of the present invention is an alcohol having 1 to 4 carbon atoms. These alcohols include methanol, ethanol, n-propanol, n-butanol, t-
Although there are butanol and the like, methanol is preferably used. The lower alcohol needs to be present in an amount of 0.005 to 5% by weight based on the raw material hydrocarbon mixture, preferably 0.01 to 1% by weight based on the raw material hydrocarbon mixture.
Even if it is present in an amount less than 0.005% by weight, there is almost no effect of adding the lower alcohol, and if it is present in an amount exceeding 5% by weight, the hydrogenation reaction of highly unsaturated hydrocarbons is inhibited. As a method for selectively hydrogenating highly unsaturated hydrocarbons without isomerizing olefins, a method of selective hydrogenation using H2 gas containing a large amount of CO gas (Japanese Patent Publication No. 46) −
30808) A method in which hydrogenation is carried out in a gas-liquid mixed phase in the first stage and a liquid phase in the second stage (Japanese Patent Publication No. 52-16082) or a method using a special catalyst (Japanese Patent Publication No. 50-28922)
German Patent No. 2108276), etc. have been proposed. However, each of these methods is expensive
It has disadvantages such as the need to use CO gas, the need to use a special catalyst, and the complicated process. The method of the present invention provides a method in which only the selective hydrogenation reaction of highly unsaturated hydrocarbons proceeds without isomerization of olefins by only the presence of a small amount of inexpensive lower alcohol, Its industrial significance is great. The hydrocarbon mixture containing highly unsaturated hydrocarbons and having a carbon number of 4 or more and having a low degree of unsaturation used in the method of the present invention is the so-called C 4 fraction obtained by steam cracking of naphtha etc. A C 4 hydrocarbon mixture consisting of butadiene, butene, butane, etc., and a C 4 hydrocarbon mixture called a so-called spent BB fraction obtained by removing most of the butadiene from this C 4 fraction by extraction. Main ingredients are 1-butene and 2-butene from which isobutylene has been removed.
Examples include C 4 hydrocarbon mixtures and hydrocarbon mixtures containing C 5 hydrocarbons such as isoprene as a main component. The highly unsaturated hydrocarbons contained in these hydrocarbon mixtures include propadiene,
Methylacetylene, 1,2-butadiene, 1,3
-Butadiene, ethyl acetylene, vinyl acetylene, 1,3-pentadiene, etc. In the method of the present invention, a palladium catalyst is used as a hydrogenation catalyst. Palladium catalysts include palladium black, palladium-supported carbon, palladium-supported alumina, etc., but catalysts in which 0.02 to 2% by weight of palladium is supported on a carrier such as alumina are usually used. The reaction form in the method of the present invention is not particularly limited, and may be carried out in any of a liquid phase, a gas phase, or a gas-liquid mixed phase such as a trickle phase. In addition, as for reaction conditions, the reaction temperature is usually -20
The reaction is carried out at a temperature of ~150°C and a reaction pressure of normal pressure to 50 atm. The method of the present invention will be explained below using Examples, but the scope of the present invention is not limited by these. Example 1 100ml of a catalyst in which 0.1% by weight of palladium was supported on alumina was packed into a vertically arranged reaction tube with an inner diameter of 20mm, and a
A hydrocarbon mixture having the composition described in the raw material column of the table with 0.2% by weight of methanol added was introduced into the reactor as a raw material at a feed rate of 500 g/hr, and hydrogen gas was added to the reactor at a feed rate of 8 (NTP equivalent). /hr
was introduced into the reactor at a feed rate of 2, to carry out a selective hydrogenation reaction. The composition of the obtained hydrocarbon product was as shown in the product column of Table 1.
【表】
このようにブタジエン、プロパジエン、ビニル
アセチレンのような高度に不飽和な炭化水素はほ
とんど水添され、かつ１―ブテンの異性化率（転
化率）は３％程度であつた。
比較例 １
メタノールを添加しないこと以外は実施例１に
記載したのと同じ方法、同じ反応条件下で水添反
応を行ない下記の結果を得た。
生成物中のブタジエン濃度……128ppm
１―ブテン転化率……10.2％
実施例２，３、比較例２
炭化水素混合物に対してメタノールを第２表に
示す割合で添加したものを原料として反応を行な
つた。なお、他の反応条件については実施例１に
記載したのと同じ方法で行なつた。また用いた炭
化水素混合物も実施例１で用いたものと同じであ
つた。
結果は表２に示すとおりであつた。[Table] As can be seen, most of the highly unsaturated hydrocarbons such as butadiene, propadiene, and vinyl acetylene were hydrogenated, and the isomerization rate (conversion rate) of 1-butene was about 3%. Comparative Example 1 A hydrogenation reaction was carried out in the same manner and under the same reaction conditions as described in Example 1, except that methanol was not added, and the following results were obtained. Butadiene concentration in the product...128 ppm 1-butene conversion rate...10.2% Examples 2 and 3, Comparative Example 2 A reaction was carried out using a hydrocarbon mixture to which methanol was added in the ratio shown in Table 2 as a raw material. I did it. The other reaction conditions were the same as those described in Example 1. The hydrocarbon mixture used was also the same as that used in Example 1. The results were as shown in Table 2.
【表】
実施例 ４，５
メタノールのかわりにエタノール、ｎ―プロパ
ノールを炭化水素混合物に対してそれぞれ0.1重
量％添加したものを原料として反応を行なつた。
なお、他の反応条件については実施例１に記載し
たのと同じ方法で行なつた。
結果は第３表に示すとおりであつた。[Table] Examples 4 and 5 A reaction was carried out using a hydrocarbon mixture containing 0.1% by weight of each of ethanol and n-propanol instead of methanol as raw materials.
The other reaction conditions were the same as those described in Example 1. The results were as shown in Table 3.
Claims (1)
の低不飽和度の炭化水素をパラジウム触媒の存在
下に水素と接触させ、前記の高度に不飽和な炭化
水素を選択的に水素添加する方法において、高度
に不飽和な炭化水素を含む炭素数４以上の低不飽
和度の炭化水素に対して0.005〜５重量％の低級
アルコールを存在させることを特徴とする炭化水
素類の選択的水素添加方法。 ２ 低級アルコールがメタノールであることを特
徴とする特許請求の範囲第１項記載の炭化水素類
の選択的水素添加方法。[Claims] 1. Hydrocarbons with a low degree of unsaturation having 4 or more carbon atoms, including highly unsaturated hydrocarbons, are brought into contact with hydrogen in the presence of a palladium catalyst, and the highly unsaturated hydrocarbons are A method of selective hydrogenation, characterized in that 0.005 to 5% by weight of a lower alcohol is present in a hydrocarbon with a low degree of unsaturation having 4 or more carbon atoms, including a highly unsaturated hydrocarbon. A method for selectively hydrogenating hydrogens. 2. The method for selectively hydrogenating hydrocarbons according to claim 1, wherein the lower alcohol is methanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56193944A JPS5896683A (en) | 1981-12-01 | 1981-12-01 | Selective hydrogenation of hydrocarbon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56193944A JPS5896683A (en) | 1981-12-01 | 1981-12-01 | Selective hydrogenation of hydrocarbon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5896683A JPS5896683A (en) | 1983-06-08 |
| JPH0153718B2 true JPH0153718B2 (en) | 1989-11-15 |
Family
ID=16316341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56193944A Granted JPS5896683A (en) | 1981-12-01 | 1981-12-01 | Selective hydrogenation of hydrocarbon |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5896683A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0696709B2 (en) * | 1987-10-23 | 1994-11-30 | 日本石油株式会社 | Method for selective hydrogenation of hydrocarbons |
-
1981
- 1981-12-01 JP JP56193944A patent/JPS5896683A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5896683A (en) | 1983-06-08 |
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