JPH02142739A - Method for isomerizing straight-chain paraffin - Google Patents
Method for isomerizing straight-chain paraffinInfo
- Publication number
- JPH02142739A JPH02142739A JP63295801A JP29580188A JPH02142739A JP H02142739 A JPH02142739 A JP H02142739A JP 63295801 A JP63295801 A JP 63295801A JP 29580188 A JP29580188 A JP 29580188A JP H02142739 A JPH02142739 A JP H02142739A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- pressure
- paraffin
- catalyst
- mixed fluid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000012188 paraffin wax Substances 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000012530 fluid Substances 0.000 claims abstract description 20
- 239000000376 reactant Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims description 35
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 239000011973 solid acid Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000010457 zeolite Substances 0.000 abstract description 5
- 229910021536 Zeolite Inorganic materials 0.000 abstract description 4
- 239000011949 solid catalyst Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000006317 isomerization reaction Methods 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 7
- 239000000571 coke Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000004939 coking Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は超臨界状態にある反応物と生成物の混合流体中
において、直鎖パラフィンを側鎖を有するパラフィンに
異性化する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a method for isomerizing straight chain paraffins into paraffins having side chains in a fluid mixture of reactants and products in a supercritical state.
直鎖パラフィンであるｎ−ブタン、ｎ−ペンタン、ｎ−
ヘキサン等を、側鎖をもつパラフィンに異性化する幾つ
かの方法が既に提案されている。その代表的なものとし
て、■白金−ゼオライド、白金−シリカ−アルミナ、白
金−アルミナ触媒等を用いる高温・低圧下での水素化異
性化法、■白金−アルミナ触媒に低温活性をもたせるた
めに微量の有機塩素化合物等を添加している低温・低圧
下での水素化異性化法、■フリーデル・クラフッ型触媒
を用いる低温・低圧下での異性化法等が挙げられる。Straight chain paraffins n-butane, n-pentane, n-
Several methods have already been proposed for isomerizing hexane and the like into paraffins having side chains. Typical examples include: ■ Hydroisomerization at high temperature and low pressure using platinum-zeolide, platinum-silica-alumina, platinum-alumina catalysts, etc.; Examples include hydroisomerization at low temperature and low pressure in which an organic chlorine compound, etc. is added, and (2) isomerization at low temperature and low pressure using a Friedel-Krauch type catalyst.
しかしながら、■の異性化法では高価な白金担持触媒を
使用する必要があり、また触媒再生時に高温により白金
微粒子がシンタリングをおこし活性が低下する恐れもあ
る。更にコーキングや触媒毒による触媒の活性劣化を防
止するために、原料の直鎖パラフィンに対して１〜４倍
モルの水素ガスを反応系に添加しなければならない。■
の異性化法は■の改良型であるが、■と同様に白金担持
触媒を用いて反応系に水素ガスを添加しており、■の場
合と同じ問題点を持っている。■の異性化法では触媒と
して塩化アルミニウムまたは臭化アルミニウムと塩化水
素を用いており、装置の腐食や運転の複雑さの問題があ
る。However, in the isomerization method (2), it is necessary to use an expensive platinum-supported catalyst, and there is also a risk that platinum fine particles may be sintered due to high temperatures during catalyst regeneration, resulting in a decrease in activity. Furthermore, in order to prevent deterioration of catalyst activity due to coking or catalyst poisoning, hydrogen gas must be added to the reaction system in an amount of 1 to 4 times the mole of linear paraffin as a raw material. ■
The isomerization method (2) is an improved version of (2), but like (2) it uses a supported platinum catalyst and hydrogen gas is added to the reaction system, and it has the same problems as (2). In the isomerization method (2), aluminum chloride or aluminum bromide and hydrogen chloride are used as catalysts, and there are problems with equipment corrosion and operational complexity.
本発明は炭素数が４〜１０の直鎖パラフィンを、側鎖を
もつパラフィンに異性化するための工業的に有利な方法
を提供することをその課題とする。An object of the present invention is to provide an industrially advantageous method for isomerizing straight chain paraffins having 4 to 10 carbon atoms into paraffins having side chains.
本発明によれば、超臨界状態にある反応物と生成物の混
合流体中で、固体酸触媒を用いて炭素数が４〜１０の直
鎖パラフィンを、側鎖をもつパラフィンに異性化する方
法が提供される。According to the present invention, a method for isomerizing straight chain paraffins having 4 to 10 carbon atoms into paraffins having side chains using a solid acid catalyst in a fluid mixture of reactants and products in a supercritical state. is provided.
本発明の方法を好まし〈実施するには、先ずはじめに反
応物の直鎖パラフィンをポンプにより触媒を充填した反
応器に導入し異性化反応を行わせる。反応温度は電気炉
またはオイル恒温槽により、圧力は反応器の上流側また
は下流側に設置した圧力調整器によりコントロールされ
ている。この時、反応温度および圧力は反応器中の反応
物と生成物からなる混合流体の臨界温度および臨界圧力
以上に％Ｐｒうに調整する。In order to preferably carry out the method of the present invention, the reactant, linear paraffin, is first introduced into a reactor filled with a catalyst using a pump, and the isomerization reaction is carried out. The reaction temperature is controlled by an electric furnace or oil constant temperature bath, and the pressure is controlled by a pressure regulator installed on the upstream or downstream side of the reactor. At this time, the reaction temperature and pressure are adjusted to be higher than the critical temperature and critical pressure of the mixed fluid consisting of reactants and products in the reactor.
次に、反応器からでた未反応物と生成物の混合流体を減
圧した後、製品として取り出す。もし製品中の側鎖をも
つパラフィン濃度を高めたい場合には、モレキュラシー
ブによる直鎖パラフィンの吸着除去や蒸留による側鎖を
もつパラフィンの濃縮等の従来公知の方法を用いること
が可能である。Next, the mixed fluid of unreacted substances and products discharged from the reactor is depressurized and then taken out as a product. If it is desired to increase the concentration of paraffins with side chains in the product, it is possible to use conventionally known methods such as adsorption removal of straight chain paraffins using a molecular sieve or concentration of paraffins with side chains by distillation.
本発明で用いられる固体酸触媒としては、例えばゼオラ
イト、モルデナイト、シリカ−アルミナ、アルミナ触媒
およびそれらに白金微粒子を担持した触媒等が挙げられ
る。Examples of the solid acid catalyst used in the present invention include zeolite, mordenite, silica-alumina, alumina catalysts, and catalysts in which platinum fine particles are supported on these catalysts.
臨界温度および臨界圧力をこえた状態にある超臨界流体
は液体に匹敵する大きな溶解力を有しており、更に流体
中の物質移動速度は液体に比べて格段に大きい。このた
め固体酸触媒を充填した反応器中において、反応物と生
成物からなる混合流体を超臨界状態になるように反応温
度と圧力を制御して反応を行うと、触媒表面に生成する
コーク先駆体やその重合物を速やかに超臨界流体中に抽
≧１咳ことができて、コーキングによる触媒の活性低下
を制御することが可能である。A supercritical fluid in a state exceeding a critical temperature and pressure has a large dissolving power comparable to that of a liquid, and furthermore, the mass transfer rate in the fluid is much higher than that of a liquid. Therefore, when a reaction is carried out in a reactor filled with a solid acid catalyst by controlling the reaction temperature and pressure to bring the mixed fluid consisting of reactants and products into a supercritical state, coke precursors are formed on the catalyst surface. It is possible to quickly extract the body and its polymer into a supercritical fluid for ≧1 hour, and it is possible to control the decrease in catalyst activity due to coking.
上記の超臨界流体の優れた性質を利用した本発明では、
従来技術の■、■で示した水素化異性化法の様に高価な
水素ガスを反応系に添加してコーキング生成を抑える必
要がない。また触媒として従来から用いられてきた白金
−ゼオライド、白金−シリカ−アルミナ等の触媒を使用
することもできるが、より安価で再生時に担持した金属
のシンタリンクの恐れのない酸性固体触媒、例えばゼオ
ライ１〜、モルデナイト、シリカ−アルミナ、アルミナ
触媒でも長期間にわたり良好な活性を維持することがで
きる。更に本発明は固体の酸性触媒を用いているため、
従来技術の■で示した異性化法の様な装置腐食の恐れは
全くない。In the present invention, which utilizes the excellent properties of the above-mentioned supercritical fluid,
There is no need to add expensive hydrogen gas to the reaction system to suppress the formation of coking, as in the hydroisomerization methods shown in the prior art (1) and (2). In addition, conventionally used catalysts such as platinum-zeolide and platinum-silica-alumina can be used, but acidic solid catalysts that are cheaper and do not cause sinterlinking of supported metals during regeneration, such as zeolite, can also be used. Even mordenite, silica-alumina, and alumina catalysts can maintain good activity for a long period of time. Furthermore, since the present invention uses a solid acidic catalyst,
There is no fear of equipment corrosion as in the isomerization method shown in the prior art (■).
次に本発明を実施例により更に詳細に説明する。 Next, the present invention will be explained in more detail with reference to Examples.
実施例１
０．２ｗｔ％白金−Ｙ型ゼオライト触媒７１．２ｇを反
応器に充填し、反応温度３２４℃、反応圧力２０．３０
５．３９３躇あ３種類、液体ｎ−ペンタン流量２ｃｉ／
ｍｉｎ、水素ガス無添加の条件でｎ−ペンタンからイソ
ペンタンへの異性化反応を行い、触媒の残存活性と時間
および反応圧力の関係を求めた。実験結果を表１中のＲ
ｕｎＮｏ、１．２．３で示す。Ｒｕｎ Ｎｏ、］の結果
から反応圧力が反応器中の混合流体の臨界圧力より低い
場合には、触媒活性が急速に低下していくことが明らか
になった。すなわち、この圧力では混合流体の溶解力が
小さく、かつコーク生成製抑制するための水素ガスが添
加されていないために、触媒表面に蓄積したコーク先駆
体が重合して触媒の活性点を覆っていくためである。一
方、Ｒｕｎ Ｎｏ、２と３の結果から反応圧力を増加さ
せて反応器中の混合流体を超臨界状態にすると、混合流
体がコーク先駆体を溶解する能力が増大し、高い触媒活
性を長時間維持できることがわかった。とりわけＲｕｎ
Ｎｏ、３の場合には、反応開始後１５時間以降の残存活
性では７０数２のほぼ一定値となり、安定した触媒活性
後長時間持続させることができた。Example 1 71.2 g of 0.2 wt% platinum-Y type zeolite catalyst was charged into a reactor, reaction temperature was 324°C, reaction pressure was 20.30
5.393a 3 types, liquid n-pentane flow rate 2ci/
The isomerization reaction from n-pentane to isopentane was carried out under conditions of 1 min and no addition of hydrogen gas, and the relationship between the residual activity of the catalyst, time, and reaction pressure was determined. The experimental results are expressed as R in Table 1.
It is indicated by unNo. 1.2.3. From the results of Run No.], it became clear that when the reaction pressure was lower than the critical pressure of the mixed fluid in the reactor, the catalyst activity decreased rapidly. That is, at this pressure, the dissolving power of the mixed fluid is small and hydrogen gas is not added to suppress coke formation, so the coke precursors accumulated on the catalyst surface polymerize and cover the active sites of the catalyst. It's to go. On the other hand, from the results of Run No. 2 and 3, increasing the reaction pressure to bring the mixed fluid in the reactor into a supercritical state increases the ability of the mixed fluid to dissolve the coke precursor, and maintains high catalyst activity for a long time. It turns out that it can be maintained. Especially Run
In the case of No. 3, the residual activity after 15 hours from the start of the reaction was a nearly constant value of 70:2, and it was possible to maintain the catalyst activity for a long time after stable catalyst activity.
実施例２
％冒担持１、い４い、型ゼオつイ）−３０，８ｇ＆あ応
器に充填し、反応温度３１４℃、液体ｎ−ペンタン流量
２ａ＆／ｍｉｎ又は０．５ａ（／ｍｉｎ、水素ガス無添
加でｎペンタンの異性化反応を行った。この時反応圧は
Ｒｕｎ Ｎｏ、４．５．６．７について各々３０．３０
６．４０５．４０５Ｋｇ／ｆｆｌであった。表１に触媒
の残存活性の時間変化を示す。実施例１に示した０、２
ｗｔ％白金−Ｖ型ゼオライト触媒の場合と同様に、Ｒｕ
ｎ Ｎｏ、４では反応器中の混合流体の圧力が臨界圧力
以下であるために触媒活性は時間と共に急激に低下した
。一方、Ｒｕｎ Ｎｏ、５．６．７では混合流体が高圧
の超臨界状態になっているため、触媒表面上のコーク先
鄭体が重合する前に超臨界流体に抽出され、触媒の劣化
が抑えられた。４０５Ｋｇ／ｃｉの圧力下で反応を行っ
たＲｕｎ Ｎｏ、６．７の実験では、反応開始から１５
時間以降では残存活性は各々約８５％と９４％であり、
安定で高い値が維持されていることが明らかになった。Example 2 A reactor was charged with 30.8 g of 1, 4, and 4% supported zeolites, and the reaction temperature was 314°C, and the liquid n-pentane flow rate was 2 or 0.5 min or 0.5 min, hydrogen The isomerization reaction of n-pentane was carried out without adding gas.At this time, the reaction pressure was 30.30 for Run No. 4, 5, 6, and 7, respectively.
It was 6.405.405Kg/ffl. Table 1 shows the change in residual activity of the catalyst over time. 0, 2 shown in Example 1
As in the case of the wt% platinum-V zeolite catalyst, Ru
In No. 4, the pressure of the mixed fluid in the reactor was below the critical pressure, so the catalyst activity rapidly decreased over time. On the other hand, in Run No. 5.6.7, the mixed fluid is in a high-pressure supercritical state, so the coke tip on the catalyst surface is extracted into the supercritical fluid before polymerization, suppressing catalyst deterioration. It was done. In the experiment with Run No. 6.7 in which the reaction was carried out under a pressure of 405 Kg/ci, 15
After hours, the residual activity is about 85% and 94%, respectively.
It became clear that stable and high values were maintained.
手 続 補 正 書hand Continued Supplementary Positive book
Claims (2)
および反応圧力が反応器中の反応物と生成物からなる混
合流体の臨界温度、臨界圧力よりも高い条件下で、反応
系に水素ガスを添加しないで、固体酸触媒を用いて側鎖
を有するパラフィンに異性化することを特徴とする直鎖
パラフィンの異性化方法。(1) Linear paraffins having 4 to 10 carbon atoms are added to the reaction system under conditions where the reaction temperature and reaction pressure are higher than the critical temperature and critical pressure of the mixed fluid consisting of reactants and products in the reactor. A method for isomerizing straight-chain paraffins, which comprises isomerizing them into paraffins having side chains using a solid acid catalyst without adding hydrogen gas.
方法。(2) The method according to claim 1, wherein the catalyst supports platinum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63295801A JPH02142739A (en) | 1988-11-22 | 1988-11-22 | Method for isomerizing straight-chain paraffin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63295801A JPH02142739A (en) | 1988-11-22 | 1988-11-22 | Method for isomerizing straight-chain paraffin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02142739A true JPH02142739A (en) | 1990-05-31 |
| JPH0530815B2 JPH0530815B2 (en) | 1993-05-11 |
Family
ID=17825341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63295801A Granted JPH02142739A (en) | 1988-11-22 | 1988-11-22 | Method for isomerizing straight-chain paraffin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02142739A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0532153A3 (en) * | 1991-06-03 | 1994-05-18 | Sun Co Inc R & M | Isomerisation of hydrocarbons with solid superacid catalyst at supercritical or near critical conditions |
| WO2014074266A1 (en) * | 2012-11-08 | 2014-05-15 | Uop Llc | Methods and apparatuses for isomerization of paraffins |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8671856B2 (en) | 2009-02-02 | 2014-03-18 | Deere & Company | Planting unit for a seeding machine having blocking member to control hand-off of seed from a seed meter to a seed delivery system |
-
1988
- 1988-11-22 JP JP63295801A patent/JPH02142739A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0532153A3 (en) * | 1991-06-03 | 1994-05-18 | Sun Co Inc R & M | Isomerisation of hydrocarbons with solid superacid catalyst at supercritical or near critical conditions |
| WO2014074266A1 (en) * | 2012-11-08 | 2014-05-15 | Uop Llc | Methods and apparatuses for isomerization of paraffins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0530815B2 (en) | 1993-05-11 |
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