JP2552712B2 - Method for producing light-colored heavy alkylate - Google Patents
Method for producing light-colored heavy alkylateInfo
- Publication number
- JP2552712B2 JP2552712B2 JP63178385A JP17838588A JP2552712B2 JP 2552712 B2 JP2552712 B2 JP 2552712B2 JP 63178385 A JP63178385 A JP 63178385A JP 17838588 A JP17838588 A JP 17838588A JP 2552712 B2 JP2552712 B2 JP 2552712B2
- Authority
- JP
- Japan
- Prior art keywords
- heavy alkylate
- catalyst
- alkylbenzene
- reaction
- alkylate
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 claims description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012188 paraffin wax Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 241001550224 Apha Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は重質アルキレート、特に洗浄剤原料アルキル
ベンゼン製造工程で得られるアルキルベンゼン蒸留回収
後の高沸点留分より淡色な重質アルキレートを製造する
方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention produces a heavy alkylate, in particular, a light-colored heavy alkylate from a high-boiling fraction after distilling and recovering alkylbenzene obtained in a detergent raw material alkylbenzene production process. On how to do.
（従来の技術） 重質アルキレートは、ジアルキルベンゼン類、ポリア
ルキルベンゼン類を主成分とする芳香族化合物であり、
一般に洗浄剤原料アルキルベンゼンの製造に際してアル
キルベンゼンよりも高沸点の副生物として得られる。(Prior Art) Heavy alkylate is an aromatic compound mainly containing dialkylbenzenes and polyalkylbenzenes,
Generally, it is obtained as a by-product having a boiling point higher than that of alkylbenzene when producing alkylbenzene as a detergent raw material.
又、アルキル化反応原料として用いられるオレフイン
中にジオレフインを含有している場合には重質アルキレ
ート中にジフェニルアルカン類をも含有する。When diolephin is contained in the olefin used as a raw material for the alkylation reaction, diphenylalkanes are also contained in the heavy alkylate.
この様な重質アルキレートは、絶縁油、潤滑油、真空
ポンプ油、熱媒体油、ゴムの伸展油、高沸点溶媒、冷凍
機油としての使用に適していることが知られているが、
アルキルベンゼンの蒸留釜残物として得られるものは、
黄褐色に着色しており前述の用途にそのまゝ用いること
はできない。It is known that such a heavy alkylate is suitable for use as an insulating oil, a lubricating oil, a vacuum pump oil, a heat carrier oil, a rubber extending oil, a high boiling point solvent, and a refrigerating machine oil,
What can be obtained as distillation residue of alkylbenzene is
It is colored yellowish brown and cannot be used as it is for the above purposes.
重質アルキレートの色相を改良する方法としては、硫
酸で処理する方法（特公昭49−19084号公報）、硫酸と
白土で処理する方法（特公昭53−17602号公報）、重質
アルキレートを蒸留し、高沸点成分を除いた後パラジウ
ムまたは白金触媒で水素添加所する方法（特公昭57−35
809号公報）等が知られている。As a method of improving the hue of heavy alkylate, a method of treating with sulfuric acid (Japanese Patent Publication No. Sho 49-19084), a method of treating with sulfuric acid and clay (Japanese Patent Publication No. 53-17602), Distillation to remove high-boiling components and then hydrogenate with palladium or platinum catalyst (Japanese Patent Publication No. 57-35
No. 809) is known.
（発明が解決しようとする課題） しかしながら、前記の硫酸（および白土）を処理剤と
して用いる方法は、廃硫酸を副生するため、その処理に
多大の手間と費用を要するという問題を有している。
又、重質アルキレートを蒸留し、高沸点成分を除いた後
パラジウムまたは白金触媒で水素添加処理する方法は、
工程数が多く手間がかかること、高価なパラジウムまた
は白金触媒を必要とするという問題を有している。(Problems to be Solved by the Invention) However, the above-mentioned method of using sulfuric acid (and white clay) as a treating agent has a problem that waste sulfuric acid is produced as a by-product, which requires a great deal of labor and cost for the treatment. There is.
Further, the method of distilling the heavy alkylate, removing the high boiling point component, and then hydrogenating with a palladium or platinum catalyst is
There are problems that the number of steps is large and labor is required, and an expensive palladium or platinum catalyst is required.
本発明は、上記問題点を解決した簡易で工業的に有利
な淡色な重質アルキレートの製造方法を提供せんとする
ものである。The present invention provides a simple and industrially advantageous method for producing a light-colored heavy alkylate that solves the above problems.
（課題を解決するための手段） 本発明者らは色相の改良された重質アルキレートの製
造方法を鋭意研究した結果、弗化水素を触媒としたアル
キルベンゼン製造の副生重質アルキレートを原料とした
場合、高沸点成分の蒸留除去を行なわなくても水素添加
処理により重質アルキレートの色相が改良できることを
見出し、本発明に致つた。(Means for Solving the Problems) As a result of intensive studies of the present inventors on a method for producing a heavy alkylate having an improved hue, the by-product heavy alkylate produced by alkylbenzene production using hydrogen fluoride as a raw material is used as a raw material. In this case, it was found that the hue of the heavy alkylate can be improved by the hydrogenation treatment without distilling and removing the high-boiling point component, and the present invention was successful.
即ち、本発明は、オレフインを弗化水素触媒の存在下
ベンゼンとアルキル化反応させるアルキルベンゼン製造
工程で得られる重質アルキレートを水素添加することを
特徴とする泡色な重質アルキレートの製造方法を提供す
るものである。That is, the present invention provides a method for producing a heavy-colored alkylate having a bubble color, which comprises hydrogenating the heavy alkylate obtained in the alkylbenzene production step of alkylating olefin with benzene in the presence of a hydrogen fluoride catalyst. Is provided.
洗浄剤原料として大量に消費されているアルキルベン
ゼンは、プロピレン等の低級オレフインオリゴマー、ｎ
−パラフインを脱水素したオレフイン、ｎ−パラフイン
を塩素化した後脱塩酸して得られるオレフイン、ワツク
スクラツキング、エチレンの低重合によるα−オレフイ
ン等のオレフインをアルキル化触媒によりベンゼンと反
応させることによつて製造される。Alkylbenzene, which is consumed in large quantities as a detergent raw material, is a lower olefin oligomer such as propylene, n
-Reaction of olefins such as dehydrogenated paraffin, olefins obtained by chlorinating n-paraffin and then dehydrochlorination, wax cracking, α-olefins by low polymerization of ethylene with benzene using an alkylation catalyst It is manufactured by.
アルキル化反応は弗化水素の存在下ベンゼンとオレフ
インのモル比１以上、好ましくは３〜10の範囲、弗化水
素対ハイドロカーボンの容積比0.2〜10、好ましくは0.5
〜２の範囲、反応温度−20〜95℃、好ましくは15〜70℃
の範囲、反応時間５〜60分間、好ましくは10〜30分間の
範囲で行なわれる。The alkylation reaction is carried out in the presence of hydrogen fluoride in a molar ratio of benzene to olefin of 1 or more, preferably in the range of 3 to 10, and a volume ratio of hydrogen fluoride to hydrocarbon of 0.2 to 10, preferably 0.5.
~ 2, reaction temperature -20 ~ 95 ℃, preferably 15 ~ 70 ℃
And a reaction time of 5 to 60 minutes, preferably 10 to 30 minutes.
アルキル化反応後の反応液はハイドロカーボン相と弗
化水素触媒相に分離される。相分離は小さい液線速度
で、滞溜時間が少なくとも90秒以上、好ましくは15分間
以上の触媒分離槽内へ反応液を通すこそにより行なわれ
る。洗浄剤原料アルキルベンゼンの品質を更に秀れたも
のにする為に、触媒相を分離したハイドロカーボン相を
再度新しい弗化水素と接触処理させてもよい。The reaction liquid after the alkylation reaction is separated into a hydrocarbon phase and a hydrogen fluoride catalyst phase. The phase separation is carried out by passing the reaction solution through the catalyst separation tank with a small liquid linear velocity and a retention time of at least 90 seconds or longer, preferably 15 minutes or longer. In order to further improve the quality of the detergent raw material alkylbenzene, the hydrocarbon phase from which the catalyst phase has been separated may be treated again with fresh hydrogen fluoride.
触媒相を分離したハイドロカーボン相は、蒸留に供さ
れ、少量溶解している触媒及び過剰に用いたベンゼンが
回収される。The hydrocarbon phase from which the catalyst phase has been separated is subjected to distillation to recover a small amount of dissolved catalyst and excess benzene.
その後、中間留分として短鎖アルキルベンゼンおよ
び，またはｎ−パラフインが蒸留して分離され、更に蒸
留をして塔頂より洗浄剤原料アルキルベンゼンを、塔底
より重質アルキレートを得る。中間留分と洗浄剤原料ア
ルキルベンゼンの蒸留は通常減圧下に行なわれる。Then, short-chain alkylbenzene and / or n-paraffin is distilled and separated as an intermediate fraction, and further distilled to obtain a cleaning agent alkylbenzene from the top of the column and a heavy alkylate from the bottom of the column. Distillation of the middle distillate and the alkyl benzene starting material for the detergent is usually carried out under reduced pressure.
本発明では弗化水素触媒を用いたものであれば、前述
のいかなる原料を用いて製造されたアルキルベンゼンと
ともに得られる重質アルキレートであつても良い。In the present invention, a heavy alkylate obtained with an alkylbenzene produced using any of the above-mentioned raw materials may be used so long as it uses a hydrogen fluoride catalyst.
弗化水素以外の触媒を用いて行なうアルキルベンゼン
の製造方法としては、ｎ−パラフインを塩素化した塩素
化パラフインを塩化アルミニウムを触媒としてベンゼン
と反応させる方法がよく知られているが、この方法で副
生する重質アルキレートを用いる場合は、前述のように
高沸点成分を除く必要があり、且つ高価なパラジウムま
たは白金触媒を用いなければならない（特公昭57−3580
9号公報参照）。A well-known method for producing alkylbenzene using a catalyst other than hydrogen fluoride is a method in which chlorinated paraffin obtained by chlorinating n-paraffin is reacted with benzene using aluminum chloride as a catalyst. When using the resulting heavy alkylate, it is necessary to remove high-boiling components as described above, and an expensive palladium or platinum catalyst must be used (Japanese Patent Publication No. 57-3580).
(See publication 9).
弗化水素を触媒に用いて得られる重質アルキレートの
色相は、用いた原料オレフインまたはアルキル化条件に
よつて異るが、一般にAPHAで100〜1000の範囲にある。The hue of the heavy alkylate obtained by using hydrogen fluoride as a catalyst depends on the raw material olefin or alkylation conditions used, but it is generally in the range of 100 to 1000 by APHA.
本発明ではこの重質アルキレートを、高沸点成分を除
くことなく水素添加する。用いられる触媒はニツケルま
たはパラジウム、白金など水素化触媒として一般に公知
のいかなるものであつても良い。In the present invention, this heavy alkylate is hydrogenated without removing high boiling components. The catalyst used may be any of those commonly known as hydrogenation catalysts such as nickel, palladium, platinum and the like.
触媒は、アルミナ、シリカアルミナ、ケイソウ土、炭
素等に担持されたものが好ましい。The catalyst is preferably supported on alumina, silica-alumina, diatomaceous earth, carbon or the like.
担持される金属の含量は、触媒がパラジウム、白金の
場合は0.1〜５重量％、ニツケルの場合20〜60重量％の
ものが用いられる。The supported metal content is 0.1 to 5% by weight when the catalyst is palladium or platinum, and 20 to 60% by weight when nickel is used.
水素添加反応装置としては、重質アルキレートと触媒
および水素ガスが効率よく接触できる形式であれば、い
かなる形式でも用いられるが、一般には粉末状触媒と重
質アルキレートをオートクレーブに入れて行なう回分式
反応、固定床充填塔を用いた連続式が採用される。As the hydrogenation reaction device, any type can be used as long as the heavy alkylate, the catalyst and the hydrogen gas can be efficiently contacted with each other, but in general, the batch catalyst prepared by placing the powdered catalyst and the heavy alkylate in the autoclave is used. The reaction system is a continuous system using a fixed bed packed column.
回分式反応を行なう場合担体に担持された触媒は重質
アルキレートに対して10〜0.5重量％を用いて行なう。When the batch reaction is carried out, the catalyst supported on the carrier is used in an amount of 10 to 0.5% by weight based on the heavy alkylate.
反応温度は100℃以上、好ましくは150℃以上で行な
う。The reaction temperature is 100 ° C. or higher, preferably 150 ° C. or higher.
水素ガス圧力は５〜100kg/cm2、更には20〜50kg/cm2
の範囲が好ましい。Hydrogen gas pressure is 5 to 100 kg / cm 2 , and further 20 to 50 kg / cm 2.
Is preferred.
水素添加に要する時間は処理前の重質アルキレートの
色相、触媒の種類と量、反応温度、水素圧力に関係する
が１〜５時間で充分である。The time required for hydrogenation depends on the hue of the heavy alkylate before treatment, the type and amount of catalyst, the reaction temperature, and the hydrogen pressure, but 1 to 5 hours is sufficient.
水素添加反応が終れば静置および、またはろ過により
触媒が除かれる。When the hydrogenation reaction is complete, the catalyst is removed by standing and / or filtration.
（実施例） 以下実施例により本発明をさらに具体的に説明する。(Example) Hereinafter, the present invention will be described in more detail with reference to Examples.
実施例１ 炭素数10〜12のｎ−パラフインを脱水素して得られる
ｎ−オレフインを弗化水素触媒によりベンゼンと反応さ
せる洗浄剤原料用アルキルベンゼン製造プラントで、触
媒相と分離されたハイドロカーボン相を蒸留して溶解弗
化水素を、次いで過剰のベンゼンを回収した後、更に蒸
溜によりｎ−パラフインが主成分の中間留分を、次いで
洗浄剤原料アルキルベンゼンを塔頂より回収した後の塔
底から得られる重質アルキレート（色相APHA500）を原
料として日揮化学製ニツケル触媒Ｎ−113を用いて、次
記により水素添加処理をした。Example 1 A hydrocarbon phase separated from a catalyst phase in an alkylbenzene production plant for a detergent raw material in which n-olefin obtained by dehydrogenating n-paraffin having 10 to 12 carbon atoms is reacted with benzene by a hydrogen fluoride catalyst. From the tower bottom after recovering dissolved hydrogen fluoride and then excess benzene, and then further distilling an intermediate fraction containing n-paraffin as a main component and then a cleaning agent alkylbenzene from the tower top. Using the resulting heavy alkylate (hue APHA500) as a raw material, a nickel catalyst N-113 manufactured by JGC Kagaku Co., Ltd. was used for hydrogenation treatment as described below.
容積500mlのオートクレーブに重質アルキレート250g
と触媒7.5gを仕込み、系内を充分窒素で置換後、更に水
素で置換した。水素で5kg/cm2に昇圧後150℃に昇温し３
時間撹拌した。室温迄冷却後減圧ろ過をして触媒を除い
た。回収した液の色相の測定結果を表１に示す。250 g of heavy alkylate in an autoclave with a volume of 500 ml
Then, 7.5 g of a catalyst was charged, and the system was thoroughly replaced with nitrogen and then replaced with hydrogen. After raising the pressure to 5 kg / cm 2 with hydrogen, raise the temperature to 150 ° C.
Stirred for hours. After cooling to room temperature, the catalyst was removed by vacuum filtration. Table 1 shows the measurement results of the hue of the collected liquid.
実施例２〜５ 反応温度、水素圧力、反応時間を夫々変えた他は、実
施例１と同様に行なつた結果を表１に示す。Examples 2 to 5 Table 1 shows the results obtained in the same manner as in Example 1 except that the reaction temperature, hydrogen pressure and reaction time were changed.
実施例６ 炭素数12〜14のｎ−パラフインを用いて得られた重質
アルキレート（APHA900）を用い、反応温度200℃、水素
圧力20kg/cm2Gで４時間反応した他は、実施例１と同様
に行なつた結果得られた重質アルキレートの色相は10以
下であつた。Example 6 A heavy alkylate (APHA900) obtained by using n-paraffin having 12 to 14 carbon atoms was used, and the reaction was carried out at a reaction temperature of 200 ° C. and a hydrogen pressure of 20 kg / cm 2 G for 4 hours. The hue of the heavy alkylate obtained as a result of the same procedure as in Example 1 was 10 or less.
実施例７〜12 アルミナに１重量％のパラジウムを担持した触媒を重
質アルキレート250gに対し2.5gを用いて、反応温度、水
素圧力、反応時間を変えて実施例１と同様に行なつた結
果を表２に示す。Examples 7 to 12 A catalyst in which 1% by weight of palladium was supported on alumina was used in the same manner as in Example 1 except that 2.5 g of 250 g of heavy alkylate was used, while changing the reaction temperature, hydrogen pressure and reaction time. The results are shown in Table 2.
実施例13 炭素数10〜14のプロピレンオリゴマーをアルキルベン
ゼン製造原料として得られた重質アルキレート（APHA7
0）を用いた他は、実施例１と同様の方法で行つた。そ
の結果得られた重質アルキレートの色相はAPHA10以下で
あつた。Example 13 A heavy alkylate (APHA7) obtained by using a propylene oligomer having 10 to 14 carbon atoms as a raw material for producing alkylbenzene.
The same method as in Example 1 was used except that 0) was used. The color of the resulting heavy alkylate was less than APHA10.
Claims (1)
ンとアルキル化反応させるアルキルベンゼン製造工程で
得られる重質アルキレートを水素添加することを特徴と
する淡色な重質アルキレートの製造方法。1. A method for producing a light-colored heavy alkylate, which comprises hydrogenating the heavy alkylate obtained in the alkylbenzene production step of alkylating olefin with benzene in the presence of a hydrogen fluoride catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63178385A JP2552712B2 (en) | 1988-07-18 | 1988-07-18 | Method for producing light-colored heavy alkylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63178385A JP2552712B2 (en) | 1988-07-18 | 1988-07-18 | Method for producing light-colored heavy alkylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0228122A JPH0228122A (en) | 1990-01-30 |
| JP2552712B2 true JP2552712B2 (en) | 1996-11-13 |
Family
ID=16047567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63178385A Expired - Lifetime JP2552712B2 (en) | 1988-07-18 | 1988-07-18 | Method for producing light-colored heavy alkylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2552712B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101386782B (en) | 2007-09-10 | 2011-04-20 | 中国石油天然气股份有限公司 | A kind of method of alkylation synthetic C14-C20 alkylbenzene for oil displacement |
| CN113548940A (en) * | 2021-07-22 | 2021-10-26 | 杭州智华杰科技有限公司 | Preparation method of high-purity alkylbenzene |
-
1988
- 1988-07-18 JP JP63178385A patent/JP2552712B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0228122A (en) | 1990-01-30 |
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