JPH04253925A - Alkylation of aromatic compound - Google Patents
Alkylation of aromatic compoundInfo
- Publication number
- JPH04253925A JPH04253925A JP3015314A JP1531491A JPH04253925A JP H04253925 A JPH04253925 A JP H04253925A JP 3015314 A JP3015314 A JP 3015314A JP 1531491 A JP1531491 A JP 1531491A JP H04253925 A JPH04253925 A JP H04253925A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic compound
- type
- alkylation
- present
- olefin
- 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.)
- Withdrawn
Links
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 11
- 238000005804 alkylation reaction Methods 0.000 title abstract description 7
- 230000029936 alkylation Effects 0.000 title description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000010457 zeolite Substances 0.000 claims abstract description 15
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000012071 phase Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims 1
- -1 alkyl aromatic compound Chemical class 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910001415 sodium ion Inorganic materials 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- 229910018404 Al2 O3 Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、Ｙ型および／またはＸ
型ゼオライト存在下で１０，０００ｐｐｍ以下の水を共
存させる芳香族化合物のアルキル化法に関し、更に詳し
くは、アルキル芳香族化合物を高選択的に製造すること
を可能にした芳香族化合物のアルキル化法である。[Industrial Field of Application] The present invention provides Y-type and/or
Regarding the alkylation method for aromatic compounds in which water of 10,000 ppm or less coexists in the presence of type zeolite, more specifically, the alkylation method for aromatic compounds that makes it possible to produce alkyl aromatic compounds with high selectivity. It is.
【０００２】0002
【従来の技術】アルキル化反応は、通常原料オレフィン
を高温度で芳香族化合物と接触させてアルキル芳香族化
合物を製造する。上記反応に用いられるアルキル化触媒
としては、塩化アルミニウム、プロトン交換型ゼオライ
ト等が、活性および選択性に優れ、広く用いられている
。BACKGROUND OF THE INVENTION In alkylation reactions, alkyl aromatic compounds are usually produced by bringing a starting olefin into contact with an aromatic compound at high temperature. As the alkylation catalyst used in the above reaction, aluminum chloride, proton exchange zeolite, etc. are widely used because of their excellent activity and selectivity.
【０００３】近年、ゼオライト触媒の存在下で液相アル
キル化反応を行なう方法として、米国特許第４，４５９
，４２６号明細書にはナトリウム含量０．７ｗｔ％以下
のプロトン交換したＹ型ゼオライトを用いるアルキル芳
香族化合物の製造方法が開示されている。[0003] In recent years, US Pat.
, No. 426 discloses a method for producing an alkyl aromatic compound using a proton-exchanged Y-type zeolite having a sodium content of 0.7 wt % or less.
【０００４】0004
【発明が解決しようとする課題】しかしながら、これま
での製造法では、原料オレフィンが二量化したアルキル
芳香族化合物の副生が認められ、最終的には収率低下に
つながっている。本発明は、この様な事情のもとで、簡
単な手段でかつ高選択率を達成する方法を提供すること
にある。[Problems to be Solved by the Invention] However, in the conventional production methods, the by-product of an alkyl aromatic compound resulting from the dimerization of the raw material olefin has been observed, which ultimately leads to a decrease in yield. The present invention aims to provide a method for achieving high selectivity with simple means under these circumstances.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、前記目的
を達成するために鋭意研究を重ねた結果、原料中の水分
濃度が、アルキル芳香族化合物生成の選択性に大きく影
響していることを見い出し、本発明を完成するに至った
。すなわち、本発明は、芳香族化合物を液相および／ま
たは気液混合相下で、選択的にＣ２ 〜Ｃ４ オレフィ
ンと接触させる方法において、触媒としてＹ型および／
またはＸ型ゼオライトを用いて１０，０００ｐｐｍ以下
の水を共存させることを特徴とするアルキル芳香族化合
物の製造方法である。[Means for Solving the Problems] As a result of intensive research to achieve the above object, the present inventors have found that the water concentration in the raw material has a large effect on the selectivity of producing an alkyl aromatic compound. This discovery led to the completion of the present invention. That is, the present invention provides a method for selectively contacting an aromatic compound with a C2 to C4 olefin in a liquid phase and/or a gas-liquid mixed phase, in which a Y-type and/or
Alternatively, it is a method for producing an alkyl aromatic compound, which is characterized in that 10,000 ppm or less of water is allowed to coexist using X-type zeolite.
【０００６】以下、本発明を詳細に説明する。本発明に
用いる芳香族化合物とは、下記化１で表わされ、例えば
、ベンゼン、トルエン、エチルベンゼン、イソプロピル
ベンゼン、ブチルベンゼン、フェノール、クロルベンゼ
ン、ブロムベンゼンなどが挙げられる。The present invention will be explained in detail below. The aromatic compound used in the present invention is represented by the following formula 1, and examples thereof include benzene, toluene, ethylbenzene, isopropylbenzene, butylbenzene, phenol, chlorobenzene, and bromobenzene.
【０００７】[0007]
【化１】[Chemical formula 1]
【０００８】本発明に用いるオレフィンとは、Ｃ２ 〜
Ｃ４ までのオレフィンでエチレン、プロピレン、ブチ
レン、イソブチレンがある。本発明に用いるゼオライト
としては、Ｘ型とＹ型があり、Ａｌ２ Ｏ３ 対ＳｉＯ
２ の割合は次のように異なる。
Ｘ型 Ａｌ２ Ｏ３ ／ＳｉＯ２ 比２〜３Ｙ型
Ａｌ２ Ｏ３ ／ＳｉＯ２ 比３〜６通常合成ゼオライ
トはそのナトリウム型で、それぞれのアルミニウム四面
体に極めて接近したナトリウムイオンとそれに釣り合う
電荷と一緒の形で合成される。本反応に用いる際はゼオ
ライトを酸で処理してナトリウムイオンとプロトンを交
換することにより合成したり、又分解性陽イオン類（一
般にはアンモニウムイオン類）で処理してナトリウムイ
オンとその分解性イオンとを交換し、その後このゼオラ
イトに熱をかけてプロトン型ゼオライトを合成し使用す
る。一般には、ナトリウムイオン型ゼオライトを水酸化
アンモニウムで処理してナトリウムイオンを除き、その
後このゼオライトを３００〜４００℃の温度で加熱して
アンモニアを除く。[0008] The olefin used in the present invention is C2-
Olefins up to C4 include ethylene, propylene, butylene, and isobutylene. Zeolites used in the present invention include X type and Y type, and Al2O3 vs. SiO
The ratio of 2 differs as follows. X type Al2O3 /SiO2 ratio 2~3Y type
Al2 O3 /SiO2 Ratio 3-6 Usually synthetic zeolites are synthesized in their sodium form with sodium ions in close proximity to each aluminum tetrahedron and a matching charge. When used in this reaction, zeolite is synthesized by treating it with an acid to exchange sodium ions and protons, or by treating it with degradable cations (generally ammonium ions) to produce sodium ions and their degradable ions. After that, heat is applied to this zeolite to synthesize proton type zeolite and use it. Generally, a sodium ion type zeolite is treated with ammonium hydroxide to remove sodium ions, and then the zeolite is heated at a temperature of 300 to 400°C to remove ammonia.
【０００９】用いられるゼオライトの形状は、例えば成
型された球状、円筒状、リング状、星型状、塊状等を云
い、ゼオライト粒子の大きさは特に限定されるものでは
ない。本発明における反応温度は７０℃〜５００℃、好
ましくは８０〜３００℃の範囲である。また、圧力は常
圧または加圧で行なわれるが好ましい範囲は大気圧〜４
０ｋｇ／ｃｍ２ の範囲である。The shape of the zeolite used may be, for example, a molded sphere, cylinder, ring, star, block, etc., and the size of the zeolite particles is not particularly limited. The reaction temperature in the present invention is in the range of 70°C to 500°C, preferably 80 to 300°C. The pressure is normal pressure or increased pressure, but the preferred range is atmospheric pressure to 4.
It is in the range of 0 kg/cm2.
【００１０】本発明は、液相および／または気液混合相
下流通法で行なわれ、反応器へ供給される芳香族化合物
／オレフィンのモル比は１〜１００、好ましくは２〜２
０の範囲で行なわれる。更に、反応器内液相中の水分濃
度は１０，０００ｐｐｍ以下である必要があり、好まし
くは１００〜４０００ｐｐｍの範囲で行なわれる。水分
濃度が１０，０００ｐｐｍ以上では、触媒が活性を失い
反応しなくなる。[0010] The present invention is carried out by a liquid phase and/or gas-liquid mixed phase flow method, and the molar ratio of aromatic compound/olefin supplied to the reactor is 1 to 100, preferably 2 to 2.
This is done in the range of 0. Further, the water concentration in the liquid phase in the reactor must be 10,000 ppm or less, preferably in the range of 100 to 4000 ppm. When the water concentration is 10,000 ppm or more, the catalyst loses its activity and no longer reacts.
【００１１】[0011]
【実施例】以下、本発明を実施例により説明するが、本
発明はこれに限定されるものではない。[Examples] The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
【００１２】0012
【実施例１】プロトン交換したＹ型ゼオライト（ＵＣＣ
製、ＬＺ−Ｙ８２）１／８″ペレット４０ｇを１６φｍ
ｍの反応管に充填し、ベンゼンとエチレンの反応を水の
共存下で行なった。実験条件は、ベンゼン／エチレン／
水モル比＝８／１／０．０４、ＷＨＳＶ（ベンゼン基準
）＝１９Ｈｒ−１、反応温度１９０℃、反応圧力２０ｋ
ｇ／ｃｍ２ で行なった。[Example 1] Proton-exchanged Y-type zeolite (UCC
manufactured by LZ-Y82) 1/8″ pellets 40g to 16φm
The reaction tube was filled into a reaction tube of 500 mL, and the reaction between benzene and ethylene was carried out in the coexistence of water. The experimental conditions were benzene/ethylene/
Water molar ratio = 8/1/0.04, WHSV (benzene standard) = 19Hr-1, reaction temperature 190℃, reaction pressure 20k
g/cm2.
【００１３】反応開始後１０時間の結果を表１に示す。Table 1 shows the results obtained 10 hours after the start of the reaction.
【００１４】[0014]
【比較例１】プロトン交換したＹ型ゼオライト（ＵＣＣ
製、ＬＺ−Ｙ８２）１／８″ペレット４０ｇを１６φｍ
ｍの反応管に充填し、ベンゼンとエチレンの反応を行な
った。実験条件は、ベンゼン／エチレンモル比＝８／１
、ＷＨＳＶ（ベンゼン基準）＝１９Ｈｒ−１、反応温度
１９０℃、反応圧力２０ｋｇ／ｃｍ２ で行なった。[Comparative Example 1] Proton-exchanged Y-type zeolite (UCC
manufactured by LZ-Y82) 1/8″ pellets 40g to 16φm
The reaction tube was filled into a reaction tube of 500 m, and benzene and ethylene were reacted. The experimental conditions were benzene/ethylene molar ratio = 8/1.
, WHSV (benzene standard) = 19 Hr-1, reaction temperature 190°C, reaction pressure 20 kg/cm2.
【００１５】反応開始後１０時間の結果を表１に示す。Table 1 shows the results obtained 10 hours after the start of the reaction.
【００１６】[0016]
【表１】[Table 1]
【００１７】[0017]
【発明の効果】本発明方法は、芳香族化合物のアルキル
化法において水を共存させることによりオレフィンの二
量化を抑制し、高選択率でアルキル芳香族化合物を得る
ことが出来、工業的に実施する際に極めて有利になる。Effects of the Invention The method of the present invention suppresses the dimerization of olefins by coexisting water in the alkylation method of aromatic compounds, and can obtain alkyl aromatic compounds with high selectivity, and can be implemented industrially. It will be extremely advantageous when doing so.
Claims (1)
液混合相下で、選択的にＣ２ 〜Ｃ４ オレフィンと接
触させる方法において、触媒としてＹ型および／または
Ｘ型ゼオライトを用いて１０，０００ｐｐｍ以下の水を
共存させることを特徴とする芳香族化合物のアルキル化
法。Claim 1. A method of selectively contacting an aromatic compound with a C2 to C4 olefin in a liquid phase and/or a gas-liquid mixed phase, using Y-type and/or X-type zeolite as a catalyst, A method for alkylating aromatic compounds characterized by coexisting water as described below.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3015314A JPH04253925A (en) | 1991-02-06 | 1991-02-06 | Alkylation of aromatic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3015314A JPH04253925A (en) | 1991-02-06 | 1991-02-06 | Alkylation of aromatic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04253925A true JPH04253925A (en) | 1992-09-09 |
Family
ID=11885324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3015314A Withdrawn JPH04253925A (en) | 1991-02-06 | 1991-02-06 | Alkylation of aromatic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04253925A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008537939A (en) * | 2005-03-31 | 2008-10-02 | エクソンモービル・ケミカル・パテンツ・インク | Production of multi-phase alkyl aromatics |
| US7517824B2 (en) | 2005-12-06 | 2009-04-14 | Exxonmobil Chemical Company | Process for steam stripping hydrocarbons from a bromine index reduction catalyst |
| US7744750B2 (en) | 2005-11-17 | 2010-06-29 | Exxonmobil Chemical Patents Inc. | Process for reducing Bromine Index of hydrocarbon feedstocks |
| US8057664B2 (en) | 2005-11-17 | 2011-11-15 | Exxonmobil Chemical Patents, Inc. | Process for reducing bromine index of hydrocarbon feedstocks |
-
1991
- 1991-02-06 JP JP3015314A patent/JPH04253925A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008537939A (en) * | 2005-03-31 | 2008-10-02 | エクソンモービル・ケミカル・パテンツ・インク | Production of multi-phase alkyl aromatics |
| JP2014015466A (en) * | 2005-03-31 | 2014-01-30 | Exxonmobile Chemical Patents Inc | Multiphase alkylaromatics production |
| US7744750B2 (en) | 2005-11-17 | 2010-06-29 | Exxonmobil Chemical Patents Inc. | Process for reducing Bromine Index of hydrocarbon feedstocks |
| US8057664B2 (en) | 2005-11-17 | 2011-11-15 | Exxonmobil Chemical Patents, Inc. | Process for reducing bromine index of hydrocarbon feedstocks |
| US7517824B2 (en) | 2005-12-06 | 2009-04-14 | Exxonmobil Chemical Company | Process for steam stripping hydrocarbons from a bromine index reduction catalyst |
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