JPH10251171A - Neutralization method - Google Patents
Neutralization methodInfo
- Publication number
- JPH10251171A JPH10251171A JP5958297A JP5958297A JPH10251171A JP H10251171 A JPH10251171 A JP H10251171A JP 5958297 A JP5958297 A JP 5958297A JP 5958297 A JP5958297 A JP 5958297A JP H10251171 A JPH10251171 A JP H10251171A
- Authority
- JP
- Japan
- Prior art keywords
- neutralization
- oil layer
- alkylbenzene
- olefin
- reaction
- 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.)
- Pending
Links
- 238000006386 neutralization reaction Methods 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 48
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000004996 alkyl benzenes Chemical class 0.000 claims abstract description 22
- 150000001336 alkenes Chemical class 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- GKBBQSONORTNLZ-UHFFFAOYSA-N (2,4-dimethyl-3-propan-2-ylpentan-3-yl)benzene Chemical compound CC(C)C(C(C)C)(C(C)C)C1=CC=CC=C1 GKBBQSONORTNLZ-UHFFFAOYSA-N 0.000 claims description 2
- FEWANSQOXSIFOK-UHFFFAOYSA-N 1,2,3,4-tetraethylbenzene Chemical compound CCC1=CC=C(CC)C(CC)=C1CC FEWANSQOXSIFOK-UHFFFAOYSA-N 0.000 claims description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 claims description 2
- VGVZNHQJMQJYJO-UHFFFAOYSA-N 1-methyl-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C)=C1C(C)C VGVZNHQJMQJYJO-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical group CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical group CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 21
- 238000005406 washing Methods 0.000 abstract description 9
- 230000003472 neutralizing effect Effects 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010555 transalkylation reaction Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- -1 ethylene, propylene Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】
【課題】 塩化アルミニウム触媒の存在下に炭素数２〜
４のオレフィンとベンゼン及び／又はアルキルベンゼン
とを反応させて得られる反応液を水洗した後に分離した
油層にアルカリ水溶液を添加する油層の中和方法であっ
て、中和反応に要する時間が短く、よって小容量の容器
により単位時間に多量の処理が可能であり、特に工業的
実施の観点から有利な中和方法を提供する。
【解決手段】 塩化アルミニウム触媒の存在下に炭素数
２〜４のオレフィンとベンゼン及び／又はアルキルベン
ゼンとを反応させて得られる反応液を水洗した後に分離
した油層にアルカリ水溶液を添加する油層の中和方法で
あって、中和時の液温が８０〜１２０℃である中和方
法。(57) [Summary] [PROBLEMS] To reduce the carbon number in the presence of an aluminum chloride catalyst
A method of neutralizing an oil layer, comprising washing a reaction solution obtained by reacting the olefin with benzene and / or alkylbenzene with water and then adding an aqueous alkali solution to the separated oil layer, wherein the time required for the neutralization reaction is short. A large-volume treatment can be performed per unit time by a small-capacity container, and a particularly advantageous neutralization method is provided from the viewpoint of industrial implementation. SOLUTION: Neutralization of an oil layer in which an alkali aqueous solution is added to a separated oil layer after a reaction solution obtained by reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is washed with water. A neutralization method wherein the liquid temperature during neutralization is 80 to 120 ° C.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、中和方法に関する
ものである。更に詳しくは、本発明は、塩化アルミニウ
ム触媒の存在下に炭素数２〜４のオレフィンとベンゼン
及び／又はアルキルベンゼンとを反応させて得られる反
応液を水洗した後に分離した油層にアルカリ水溶液を添
加する油層の中和方法であって、中和反応に要する時間
が短く、よって小容量の容器により多量の処理が可能で
あり、特に工業的実施の観点から有利な中和方法に関す
るものである。The present invention relates to a neutralization method. More specifically, in the present invention, a reaction solution obtained by reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is washed with water, and then an aqueous alkali solution is added to the separated oil layer. The present invention relates to a method for neutralizing an oil layer, which is a method that requires a short time for the neutralization reaction, and thus enables a large amount of treatment in a small-capacity container, and is particularly advantageous from the viewpoint of industrial implementation.
【０００２】[0002]
【従来の技術】塩化アルミニウム触媒の存在下に炭素数
２〜４のオレフィンとベンゼン及び／又はアルキルベン
ゼンとを反応させる反応は、フリーデルクラフト反応と
して知られている。フリーデルクラフト反応により得ら
れた反応液は、残留触媒を失活処理するために水洗工程
に付される。水洗工程で得られる油水混合層から分離さ
れた油層はアルカリ水溶液を添加することにより中和さ
れる。これは、水洗後の油層は触媒成分の混入により酸
性を呈するが、酸性を呈する油層をそのまま後工程であ
る蒸留工程に付した場合、装置の腐蝕を発生し、不都合
であるからである。ところで、従来の方法によると、十
分に中和反応を完遂するためには十分に長い反応時間を
要し、小容量の容器で単位時間に多量の油層を中和する
場合には、酸性成分の一部が下流へリークし、その対策
のために、経済的には不利である大容量の反応器を用い
ざるを得ないという問題があった。2. Description of the Related Art A reaction for reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is known as a Friedel-Crafts reaction. The reaction solution obtained by the Friedel-Crafts reaction is subjected to a water washing step to deactivate the residual catalyst. The oil layer separated from the oil-water mixed layer obtained in the water washing step is neutralized by adding an aqueous alkali solution. This is because the oil layer after water washing becomes acidic due to the incorporation of the catalyst component, but if the oil layer showing acidity is directly subjected to the subsequent distillation step, corrosion of the apparatus occurs, which is inconvenient. By the way, according to the conventional method, a sufficiently long reaction time is required to complete the neutralization reaction sufficiently, and when a large amount of oil layer is neutralized per unit time in a small-capacity container, the acid component of There was a problem that a part of the reactor leaked downstream and a large-capacity reactor, which was economically disadvantageous, had to be used for the countermeasure.
【０００３】[0003]
【発明が解決しようとする課題】かかる状況に鑑み、本
発明が解決しようとする課題は、塩化アルミニウム触媒
の存在下に炭素数２〜４のオレフィンとベンゼン及び／
又はアルキルベンゼンとを反応させて得られる反応液を
水洗した後に分離した油層にアルカリ水溶液を添加する
油層の中和方法であって、中和反応に要する時間が短
く、よって小容量の容器により単位時間に多量の油層の
処理が可能であり、特に工業的実施の観点から有利な中
和方法を提供する点に存するものである。In view of such circumstances, an object of the present invention is to provide an olefin having 2 to 4 carbon atoms and benzene and / or benzene in the presence of an aluminum chloride catalyst.
Or a method of neutralizing an oil layer in which an aqueous alkali solution is added to an oil layer separated after washing a reaction solution obtained by reacting with alkylbenzene with an aqueous alkali solution. Accordingly, it is possible to treat a large amount of oil layer, and to provide an advantageous neutralization method particularly from the viewpoint of industrial implementation.
【０００４】[0004]
【課題を解決するための手段】すなわち、本発明は、塩
化アルミニウム触媒の存在下に炭素数２〜４のオレフィ
ンとベンゼン及び／又はアルキルベンゼンとを反応させ
て得られる反応液を水洗した後に分離した油層にアルカ
リ水溶液を添加する油層の中和方法であって、中和時の
液温が８０〜１２０℃である中和方法に係るものであ
る。That is, according to the present invention, a reaction solution obtained by reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is separated after washing with water. The present invention relates to a method for neutralizing an oil layer by adding an aqueous alkali solution to the oil layer, wherein the liquid temperature during neutralization is 80 to 120 ° C.
【０００５】[0005]
【発明の実施の形態】塩化アルミニウム触媒の存在下に
炭素数２〜４のオレフィンとベンゼン及び／又はアルキ
ルベンゼンとを反応させる方法は、いわゆるフリーデル
クラフト反応として知られるものである。DESCRIPTION OF THE PREFERRED EMBODIMENTS A method for reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is known as a so-called Friedel-Crafts reaction.
【０００６】塩化アルミニウム触媒としては、本発明の
分野において通常使用されるものを用いることができ、
塩化アルミニウムと塩化水素又はエチルクロライド及び
炭化水素油から調製した液体塩化アルミニウム触媒が好
ましい。[0006] As the aluminum chloride catalyst, those usually used in the field of the present invention can be used.
Liquid aluminum chloride catalysts prepared from aluminum chloride and hydrogen chloride or ethyl chloride and a hydrocarbon oil are preferred.
【０００７】炭素数２〜４のオレフィンとしては、エチ
レン、プロピレン及びブテンをあげることができる。ア
ルキルベンゼンのアルキル基としては、メチル基、エチ
ル基、イソプロピル基、ブチル基などをあげることがで
きる。アルキルベンゼンは、通常１〜４のアルキル基を
含有するものが用いられる。具体例を示すならば、オレ
フィンがエチレンであり、アルキルベンゼンがモノエチ
ルベンゼン、ジエチルベンゼン、トリエチルベンゼン又
はテトラエチルベンゼンである場合、オレフィンがプロ
ピレンであり、アルキルベンゼンがモノイソプロピルベ
ンゼン、ジイソプロピルベンゼン又はトリイソプロピル
ベンゼンである場合、オレフィンがプロピレンであり、
アルキルベンゼンがモノイソプロピルトルエン、ジイソ
プロピルトルエン又はトリイソプロピルトルエンである
場合等をあげることができる。これらの反応は、いわゆ
るアルキル化反応及び／又はトランンスアルキル化反応
を含むものである。反応においては、通常ベンゼン又は
アルキルベンゼンが反応溶媒としても作用する。[0007] Examples of the olefin having 2 to 4 carbon atoms include ethylene, propylene and butene. Examples of the alkyl group of the alkylbenzene include a methyl group, an ethyl group, an isopropyl group, and a butyl group. As the alkylbenzene, those containing 1 to 4 alkyl groups are usually used. For example, when the olefin is ethylene and the alkylbenzene is monoethylbenzene, diethylbenzene, triethylbenzene or tetraethylbenzene, the olefin is propylene and the alkylbenzene is monoisopropylbenzene, diisopropylbenzene or triisopropylbenzene. The olefin is propylene,
Examples include the case where the alkylbenzene is monoisopropyltoluene, diisopropyltoluene or triisopropyltoluene. These reactions include so-called alkylation reactions and / or transalkylation reactions. In the reaction, benzene or alkylbenzene usually also acts as a reaction solvent.
【０００８】上記反応の反応液は、触媒を失活処理する
ために水洗工程に付される。水洗工程で得られた油水混
合層は、油層と水層に分離される。分離された油層は酸
性成分である塩化アルミニウム及び塩化水素を含有する
ため、通常１〜３程度のｐＨ値を呈する。該油層は、ア
ルカリ水溶液を添加することにより中和される。アルカ
リとしては、通常水酸化ナトリウム（苛性ソーダ）が用
いられる。アルカリ水溶液のアルカリ濃度は、通常３〜
１０重量％である。[0008] The reaction solution of the above reaction is subjected to a water washing step to deactivate the catalyst. The oil / water mixed layer obtained in the water washing step is separated into an oil layer and an aqueous layer. Since the separated oil layer contains the acidic components aluminum chloride and hydrogen chloride, it usually exhibits a pH value of about 1 to 3. The oil layer is neutralized by adding an aqueous alkali solution. As the alkali, sodium hydroxide (caustic soda) is usually used. The alkali concentration of the aqueous alkali solution is usually 3 to
10% by weight.
【０００９】本発明においては、中和時の液温を８０〜
１２０℃、好ましくは９０〜１１０℃に維持する必要が
ある。該液温が低すぎると中和反応の速度が遅く、本発
明の前記目的を達成することができない。一方、該液温
が高すぎると熱経済的に不利であり、更に装置材質には
より苛性割れの起こりにくい高級材質を採用せねばなら
ず、この点においても経済的に不利である。In the present invention, the temperature of the solution at the time of neutralization is from 80 to
It must be maintained at 120C, preferably 90-110C. If the liquid temperature is too low, the speed of the neutralization reaction is too slow to achieve the above object of the present invention. On the other hand, if the liquid temperature is too high, it is disadvantageous thermoeconomically, and furthermore, a high-grade material, which is less likely to cause caustic cracking, must be used as the material of the apparatus, which is also disadvantageous economically.
【００１０】中和反応を行う具体的方法としては、中和
する油層にアルカリ水溶液を添加し、撹袢・混合すれば
よい。液温を前記の範囲に維持する方法としては、スチ
ームジャケットを有する中和反応器を用い、該スチーム
ジャケット及び／又はスチームヒーター（加熱器）によ
り加熱を行う方法をあげることができる。As a specific method for performing the neutralization reaction, an aqueous alkali solution is added to the oil layer to be neutralized, followed by stirring and mixing. As a method for maintaining the liquid temperature in the above range, a method in which a neutralization reactor having a steam jacket is used and heating is performed by the steam jacket and / or a steam heater (heater) can be mentioned.
【００１１】中和後の油層は、蒸留工程により目的のア
ルキルベンゼンが分離取得されるとともにベンゼン及び
目的のアルキルベンゼン以外のアルキルベンゼンは、前
記のフリーデルクラフト反応工程に再循環され、アルキ
ル化又はトランスアルキル化反応に付される。In the oil layer after the neutralization, the desired alkylbenzene is separated and obtained by a distillation step, and benzene and alkylbenzene other than the desired alkylbenzene are recycled to the above-mentioned Friedel-Crafts reaction step to carry out alkylation or transalkylation. Attached to the reaction.
【００１２】[0012]
【実施例】次に、実施例により本発明を説明する。Next, the present invention will be described by way of examples.
【００１３】実施例１ 塩化アルミニウム触媒の存在下にプロピレンとベンゼン
及びアルキルベンゼンとを反応させて得られた反応液を
水洗した後に分離した油層であって、ベンゼン５重量
％、モノイソプロピルベンゼン２５重量％、ジイソプロ
ピルベンゼン５１重量％、トリイソプロピルベンゼン１
３．５重量％を含有する油層（ＰＨ＝２）１４５００ｋ
ｇ／ｈr を、下流の中和油水分離槽から循環されるアル
カリ水１３０００ｋｇ／ｈｒと混合し、中和反応槽で中
和反応を行なった。中和反応槽は容量１００００リット
ルの攪拌機つきの反応器でありジャッケットに１．５ｋ
ｇ／ｃｍ2 Ｇのスチームを通じて加熱して温度９５℃に
調節した。中和処理された油と水は中和油水分離槽に送
られ、分離したアルカリ水は系内アルカリ水量が一定と
なるように１部を系外に排出し、残りのアルカリ水は水
酸化ナトリウム水溶液（３０重量％）と補給水を添加し
て水酸化ナトリウム（５重量％）塩化ナトリウム（２重
量％）に調合して１．５ｋｇ／ｃｍ2 Ｇスチーム２重管
熱交換器で９５℃まで加熱して中和反応槽上流に循環使
用した。中和反応油は、残留する水酸化ナトリウムを水
洗除去後、蒸留塔でベンゼンとモノイソプロピルベンゼ
ンとフィード中に含まれる水を塔頂へ分離した。塔頂蒸
気に含まれる水分は凝縮器でベンゼン、モノイソプロピ
ルベンゼンと共に凝縮し、還流槽で静置分離排出した。
この時の排水中の塩素イオン濃度は５００ｐｐｍであっ
た。Example 1 An oil layer separated from a reaction solution obtained by reacting propylene with benzene and alkylbenzene in the presence of an aluminum chloride catalyst and then washed with water, comprising 5% by weight of benzene and 25% by weight of monoisopropylbenzene , Diisopropylbenzene 51% by weight, triisopropylbenzene 1
Oil layer containing 3.5% by weight (PH = 2) 14500k
g / hr was mixed with 13000 kg / hr of alkaline water circulated from a downstream neutralized oil / water separation tank, and a neutralization reaction was carried out in a neutralization reaction tank. The neutralization reactor is a reactor with a stirrer with a capacity of 10,000 liters.
The temperature was adjusted to 95 ° C. by heating through steam of g / cm 2 G. The neutralized oil and water are sent to a neutralized oil / water separation tank. One part of the separated alkaline water is discharged out of the system so that the amount of alkaline water in the system is constant, and the remaining alkaline water is sodium hydroxide. An aqueous solution (30% by weight) and make-up water are added to prepare sodium hydroxide (5% by weight) and sodium chloride (2% by weight), and to 95 ° C. with a 1.5 kg / cm 2 G steam double tube heat exchanger. It was heated and circulated upstream of the neutralization reactor. The neutralized reaction oil was washed with water to remove residual sodium hydroxide, and then benzene, monoisopropylbenzene, and water contained in the feed were separated at the top of the distillation column. The water contained in the vapor at the top was condensed with benzene and monoisopropylbenzene in a condenser, and then separated and discharged in a reflux tank.
At this time, the chlorine ion concentration in the wastewater was 500 ppm.
【００１４】比較例１ 中和反応の液温を７０℃としたこと以外は、実施例１と
同様に行った。第１塔還流槽から排出される排水中の塩
素イオン濃度は２０００ｐｐｍであった。Comparative Example 1 An experiment was carried out in the same manner as in Example 1 except that the liquid temperature of the neutralization reaction was 70 ° C. The chlorine ion concentration in the wastewater discharged from the first tower reflux tank was 2000 ppm.
【００１５】[0015]
【発明の効果】以上説明したとおり、本発明により、塩
化アルミニウム触媒の存在下に炭素数２〜４のオレフィ
ンとベンゼン及び／又はアルキルベンゼンとを反応させ
て得られる反応液を水洗した後に分離した油層にアルカ
リ水溶液を添加する油層の中和方法であって、中和反応
に要する時間が短く、よって小容量の容器により単位時
間に多量の処理が可能であり、特に工業的実施の観点か
ら有利な中和方法を提供することができた。As described above, according to the present invention, an oil layer separated after washing a reaction solution obtained by reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is washed with water. A method for neutralizing an oil layer by adding an aqueous alkali solution to the oil layer, the time required for the neutralization reaction is short, so that a large amount of processing can be performed per unit time with a small-capacity container, which is particularly advantageous from the viewpoint of industrial implementation. A neutralization method could be provided.
Claims (5)
２〜４のオレフィンとベンゼン及び／又はアルキルベン
ゼンとを反応させて得られる反応液を水洗した後に分離
した油層にアルカリ水溶液を添加する油層の中和方法で
あって、中和時の液温が８０〜１２０℃である中和方
法。1. An oil layer in which a reaction solution obtained by reacting an olefin having 2 to 4 carbon atoms with benzene and / or alkylbenzene in the presence of an aluminum chloride catalyst is washed with water and then an aqueous alkali solution is added to the separated oil layer. A neutralization method wherein the liquid temperature during neutralization is 80 to 120 ° C.
ベンゼンがモノエチルベンゼン、ジエチルベンゼン、ト
リエチルベンゼン又はテトラエチルベンゼンである請求
項１記載の中和方法。2. The method according to claim 1, wherein the olefin is ethylene and the alkylbenzene is monoethylbenzene, diethylbenzene, triethylbenzene or tetraethylbenzene.
ルベンゼンがモノイソプロピルベンゼン、ジイソプロピ
ルベンゼン又はトリイソプロピルベンゼンである請求項
１記載の中和方法。3. The method according to claim 1, wherein the olefin is propylene and the alkylbenzene is monoisopropylbenzene, diisopropylbenzene or triisopropylbenzene.
ルベンゼンがモノイソプロピルトルエン、ジイソプロピ
ルトルエン又はトリイソプロピルトルエンである請求項
１記載の中和方法。4. The method according to claim 1, wherein the olefin is propylene and the alkylbenzene is monoisopropyltoluene, diisopropyltoluene or triisopropyltoluene.
を用い、該スチームジャケットにより加熱を行う請求項
１記載の中和方法。5. The neutralization method according to claim 1, wherein a neutralization reactor having a steam jacket is used, and heating is performed using the steam jacket.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5958297A JPH10251171A (en) | 1997-03-13 | 1997-03-13 | Neutralization method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5958297A JPH10251171A (en) | 1997-03-13 | 1997-03-13 | Neutralization method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10251171A true JPH10251171A (en) | 1998-09-22 |
Family
ID=13117374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5958297A Pending JPH10251171A (en) | 1997-03-13 | 1997-03-13 | Neutralization method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10251171A (en) |
-
1997
- 1997-03-13 JP JP5958297A patent/JPH10251171A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5185113B2 (en) | Method for deactivating organometallic catalyst and reactor system therefor | |
| EP0885181B1 (en) | Alkylation process using hydrogen fluoride-containing alkylation catalysts | |
| WO2012009050A2 (en) | Startup procedures for ionic liquid catalyzed hydrocarbon conversion processes | |
| US4783567A (en) | HF alkylation process | |
| TWI546278B (en) | A process for producing alkylated aromatic hydrocarbons | |
| US3931350A (en) | Process for producing alkylaromatics | |
| SU609459A3 (en) | Method of obtaining ethyl benzene | |
| CZ74496A3 (en) | Process of removing catalyst from oligomer product | |
| NO301261B1 (en) | Regeneration of alkylation catalyst | |
| US5386072A (en) | Process for the preparation of linear alkylbenzenes | |
| US3911043A (en) | Plural stages of HF alkylation of isoparaffin with a mono-olefin | |
| JPH10251171A (en) | Neutralization method | |
| US3607970A (en) | Process for producing high octane alkylated hydrocarbons substantially free of alkyl fluoride compounds | |
| NO301106B1 (en) | Process for regeneration of alkylation catalyst and process for alkylation | |
| US3972956A (en) | Avoiding pollution by HF catalyst residues in alkylation | |
| US4275032A (en) | Alkylation combined settler-soaker apparatus | |
| US4162273A (en) | Alkaline treatment of liquid propane containing HF | |
| RU2102369C1 (en) | Method of alkylation of paraffin stock with olefins | |
| US4039603A (en) | Vapor pressure-adjusted motor fuel alkylate of reduced fluoride content | |
| US3306943A (en) | Process for the preparation of p-dhsopropylbenzene | |
| CZ59293A3 (en) | Process of enhancing quality of paraffin starting material | |
| US4218574A (en) | Hydrofluoric acid alkylation utilizing a unitary settler-soaker vessel | |
| JP2749658B2 (en) | Method for producing cumene | |
| KR100223531B1 (en) | Method for producing isobutene oligomer | |
| JPS6241218B2 (en) |