JP2006219445A - Method for producing chlorinated aromatic compound - Google Patents
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Abstract
Description
本発明は、塩素化芳香族化合物の製造方法に関するものである。更に詳しくは、本発明は、芳香族化合物と塩素から塩素化芳香族化合物を製造する方法であって、省エネルギーの観点に優れる塩素化芳香族化合物の製造方法に関するものである。 The present invention relates to a method for producing a chlorinated aromatic compound. More specifically, the present invention relates to a method for producing a chlorinated aromatic compound from an aromatic compound and chlorine, and relates to a method for producing a chlorinated aromatic compound excellent in energy saving.
たとえばベンゼンのような芳香族化合物を塩素により塩素化することによりクロルベンゼン（モノクロルベンゼンを意味する。以下、同じ。）のような塩素化芳香族化合物を製造する方法は公知である（たとえば、特許文献１参照。）。ここで、塩素化反応にて得られる反応混合物には、目的物である塩素化芳香族化合物の他に種々の副生物が共存する。そこで、かかる反応混合物から目的物である塩素化芳香族化合物を効率的に精製分離して回収する必要がある。 For example, a method for producing a chlorinated aromatic compound such as chlorobenzene (monochlorobenzene means the same hereinafter) by chlorinating an aromatic compound such as benzene with chlorine is known (for example, patents). Reference 1). Here, in the reaction mixture obtained by the chlorination reaction, various by-products coexist in addition to the target chlorinated aromatic compound. Therefore, it is necessary to efficiently purify and recover the target chlorinated aromatic compound from the reaction mixture.
かかる状況において、本発明が解決しようとする課題は、省エネルギーの観点に優れる塩素化芳香族化合物の製造方法を提供する点にある。 Under such circumstances, the problem to be solved by the present invention is to provide a method for producing a chlorinated aromatic compound that is excellent in terms of energy saving.
すなわち、本発明は、下記の工程を含む塩素化芳香族化合物の製造方法であって、塩素化芳香族化合物精製工程で得られる塩素化芳香族化合物の有する熱で塩素化工程へ原料として供給される芳香族化合物を加熱する塩素化芳香族化合物の製造方法に係るものである。
塩素化工程：芳香族化合物と塩素を反応させ、塩素化芳香族化合物と塩化水素を得る工程
塩素化芳香族化合物精製工程：塩素化工程で得られる反応混合物を精製することにより精製された塩素化芳香族化合物を得る工程
That is, the present invention is a method for producing a chlorinated aromatic compound including the following steps, which is supplied as a raw material to the chlorination step by the heat of the chlorinated aromatic compound obtained in the chlorinated aromatic compound purification step. This invention relates to a method for producing a chlorinated aromatic compound in which an aromatic compound is heated.
Chlorination step: A step of reacting an aromatic compound with chlorine to obtain a chlorinated aromatic compound and hydrogen chloride Chlorination aromatic compound purification step: Chlorination purified by purifying the reaction mixture obtained in the chlorination step Step of obtaining an aromatic compound
本発明により、省エネルギーの観点に優れる塩素化芳香族化合物の製造方法を提供することができる。 By this invention, the manufacturing method of the chlorinated aromatic compound which is excellent in an energy-saving viewpoint can be provided.
本発明の塩素化工程は、芳香族化合物と塩素を反応させ、塩素化芳香族化合物と塩化水素を得る工程である。 The chlorination step of the present invention is a step in which an aromatic compound and chlorine are reacted to obtain a chlorinated aromatic compound and hydrogen chloride.
塩素化芳香族化合物としては、クロルベンゼン、１,２−、１,３−又は１,４−ジクロルベンゼン、１,２,３−、１,２,４−又は１,３,５−トリクロルベンゼン、テトラー、ペンター又はヘキサクロルベンゼン、モノ又はポリクロロトルエン、モノ又はポリクロロキシレン等をあげることができる。また、それらの化合物の芳香環がニトロ基、アミノ基、アルキル基（メチル基を除く。）等の置換基で置換されていてもよい。更に、上記の単環式芳香族化合物の他に、ナフタレン環、アントラセン環等の多環式芳香族化合物であってもよい。また、芳香環に直接塩素が置換された化合物のみならず、塩化ベンジル、クミルクロライドのように芳香環の置換基が塩素化されたものであってもよい。 The chlorinated aromatic compound may be chlorobenzene, 1,2-, 1,3- or 1,4-dichlorobenzene, 1,2,3-, 1,2,4- or 1,3,5-trichloro. Examples thereof include benzene, tetra-, penta- or hexachlorobenzene, mono- or polychlorotoluene, mono- or polychloroxylene, and the like. Moreover, the aromatic ring of those compounds may be substituted with a substituent such as a nitro group, an amino group, or an alkyl group (excluding a methyl group). Further, in addition to the monocyclic aromatic compound, a polycyclic aromatic compound such as a naphthalene ring or an anthracene ring may be used. Further, not only compounds in which the aromatic ring is directly substituted with chlorine, but also those in which the aromatic ring substituents are chlorinated, such as benzyl chloride and cumyl chloride.
芳香族化合物としては、ベンゼン，トルエン，キシレン等を上げることができる。 Examples of aromatic compounds include benzene, toluene, xylene and the like.
芳香族化合物としてベンゼンを用い、塩素化芳香族化合物であるクロルベンゼンを得る方法が産業上の観点から特に重要である。 A method of obtaining chlorbenzene, which is a chlorinated aromatic compound, using benzene as the aromatic compound is particularly important from an industrial viewpoint.
芳香族化合物と塩素を反応させる方法については、特に制限はなく、公知の方法を使用することができる。具体的な方法の例を示すと、次のとおりである。芳香族化合物と塩素のモル比（芳香族化合物／塩素）は３以上であり、反応温度は２５〜１３０℃であり、反応圧力は０．０２〜０．５ＭＰａである。反応器としては、たとえば槽型反応器を用いることができる。反応には触媒としてＦｅＣｌ2を用いることができる。 There is no restriction | limiting in particular about the method of making an aromatic compound and chlorine react, A well-known method can be used. An example of a specific method is as follows. The molar ratio of aromatic compound to chlorine (aromatic compound / chlorine) is 3 or more, the reaction temperature is 25 to 130 ° C., and the reaction pressure is 0.02 to 0.5 MPa. As the reactor, for example, a tank reactor can be used. For the reaction, FeCl 2 can be used as a catalyst.
本発明の塩素化芳香族化合物精製工程は、塩素化工程で得られる反応混合物を精製することにより精製された塩素化芳香族化合物を得る工程である。反応混合物には未反応芳香族化合物、塩素化芳香族化合物を含み、塩素化芳香族化合物の精製には蒸留塔が用いられる。蒸留塔塔頂に未反応芳香族化合物を留去回収し、塔底には精製された塩素化芳香族化合物を得るが、塔底温度迄熱せられた塩素化芳香族化合物は、加熱源としての熱を有する。塩素化工程に供給される原料芳香族化合物を加熱する事によって塩素化工程に塩素化芳香族化合物精製で得られる塩素化芳香族化合物の有する熱を回収する事が出来る。塩素化工程に供給される原料芳香族化合物は、外部から供給される芳香族化合物と塩素化工程の後工程である塩素化芳香族化合物精製工程等からリサイクルされる未反応芳香族化合物が当てられるが、塩素化芳香族化合物の有する熱を回収の為の加熱される芳香族化合物は外部から供給される芳香族化合物であっても良いしリサイクル芳香族化合物であっても良い。又、両芳香族化合物を混合した芳香族化合物であっても良い。通常熱せられた精製塩素化芳香族化合物は冷却水等で冷却されて製品タンク等に保管されるが、本発明では冷却を原料芳香族化合物との熱交換により行なう為、外部冷却水による冷却エネルギーの節減にもなる一挙両得の省エネルギーの観点に優れる塩素化芳香族化合物の製造方法である。 The chlorinated aromatic compound purification step of the present invention is a step of obtaining a purified chlorinated aromatic compound by purifying the reaction mixture obtained in the chlorination step. The reaction mixture contains an unreacted aromatic compound and a chlorinated aromatic compound, and a distillation column is used for purification of the chlorinated aromatic compound. Unreacted aromatic compounds are distilled and recovered at the top of the distillation column to obtain purified chlorinated aromatic compounds at the bottom of the column. Have heat. By heating the raw material aromatic compound supplied to the chlorination step, the heat of the chlorinated aromatic compound obtained by refining the chlorinated aromatic compound in the chlorination step can be recovered. The raw material aromatic compound supplied to the chlorination step is applied with an aromatic compound supplied from the outside and an unreacted aromatic compound recycled from the chlorination aromatic compound purification step which is a subsequent step of the chlorination step. However, the aromatic compound heated for recovering the heat of the chlorinated aromatic compound may be an aromatic compound supplied from the outside or a recycled aromatic compound. Moreover, the aromatic compound which mixed both aromatic compounds may be sufficient. Normally heated purified chlorinated aromatic compounds are cooled with cooling water or the like and stored in a product tank or the like. However, in the present invention, cooling is performed by heat exchange with the raw material aromatic compounds, so cooling energy by external cooling water is used. This is a method for producing a chlorinated aromatic compound that is excellent in terms of energy saving.
反応混合物中の未反応芳香族が多く含まれる場合は、塩素化芳香族化合物精製工程の前に塩素化芳香族化合物濃縮工程を設け蒸留塔を用い未反応芳香族の一部を塔頂に留去回収し塔底に濃縮された塩素化芳香族化合物を得て、濃縮された塩素化芳香族化合物を塩素化芳香族化合物精製工程に供すれば、塩素化芳香族化合物精製工程の蒸留塔に加えるエネルギーが少なくて済む効果がある。 If the reaction mixture contains a large amount of unreacted aromatics, a chlorinated aromatic compound concentration step is provided before the chlorinated aromatic compound purification step, and a part of the unreacted aromatics is retained at the top of the column using a distillation column. If the chlorinated aromatic compound collected at the bottom and collected at the bottom of the tower is obtained, and the concentrated chlorinated aromatic compound is subjected to the chlorinated aromatic compound purification step, it is added to the distillation column of the chlorinated aromatic compound purification step. There is an effect that less energy is required.
塩素化芳香族化合物精製工程及び塩素化芳香族化合物濃縮工程から回収された芳香族化合物は塩素化工程に塩素化芳香族化合物製造の原料としてリサイクルされる。
The aromatic compound recovered from the chlorinated aromatic compound purification step and the chlorinated aromatic compound concentration step is recycled to the chlorination step as a raw material for producing the chlorinated aromatic compound.
本発明の最大の特徴のひとつは、塩素化芳香族化合物精製工程で得られる塩素化芳香族化合物の有する熱で塩素化工程へ原料として供給される芳香族化合物を加熱する点にある。このことにより、本発明が解決しようとする前記の課題を解決することができるのである。 One of the greatest features of the present invention is that the aromatic compound supplied as a raw material to the chlorination process is heated by the heat of the chlorinated aromatic compound obtained in the chlorinated aromatic compound purification process. As a result, the above-mentioned problems to be solved by the present invention can be solved.
次に本発明を実施例により説明する。
実施例１
ベンゼンと塩素を反応させてモノクロルベンゼンを得た。反応はベンゼン液中に塩素を吹き込む方法とし、反応温度８８℃、反応圧力０．１５ＭＰａとした。原料塩素流量は４２１ｋｇ−ｍｏｌ／ｈｒであり、原料として供給するベンゼン／塩素モル比は８．０／１．０とした。反応には触媒として塩化第二鉄を用いた。
反応混合物中の未反応ベンゼンが多い為、塩素化芳香族化合物濃縮工程を設け、蒸留塔の塔頂からモノクロルベンゼンを含む未反応ベンゼンを１１０５ｋｇ−ｍｏｌ／ｈｒ（流体番号６）留出回収し塔底に濃縮されたモノクロルベンゼン１０７０ｋｇ−ｍｏｌ／ｈｒ（流体番号７）を得て塩素化芳香族化合物精製工程に供した。塩素化芳香族化合物精製工程の操作圧０．１ＭＰａの蒸留塔の塔頂から未反応ベンゼンを留去回収し塔底に１３１℃の精製されたモノクロルベンゼン３６５ｋｇ−ｍｏｌ／ｈｒ（流体番号９）を得た。この熱を有するモノクロルベンゼンを熱交換器（符号Ｄ）に供給し、外部から供給される４０℃の原料ベンゼン１６３０ｋｇ−ｍｏｌ／ｈｒ（流体番号２）と熱交換させ、原料ベンゼンに１３１５ＫＷの熱を回収して５５℃まで冷却するとともに、原料ベンゼンを６１℃まで昇温して塩素化工程に供給した。
Next, the present invention will be described with reference to examples.
Example 1
Monochlorobenzene was obtained by reacting benzene with chlorine. The reaction was carried out by blowing chlorine into the benzene solution, with a reaction temperature of 88 ° C. and a reaction pressure of 0.15 MPa. The raw material chlorine flow rate was 421 kg-mol / hr, and the benzene / chlorine molar ratio supplied as the raw material was 8.0 / 1.0. Ferric chloride was used as a catalyst for the reaction.
Since there is a large amount of unreacted benzene in the reaction mixture, a chlorinated aromatic compound concentration step is provided, and 1105 kg-mol / hr (fluid number 6) of unreacted benzene containing monochlorobenzene is recovered from the top of the distillation column. Monochlorobenzene 1070 kg-mol / hr (fluid number 7) concentrated at the bottom was obtained and subjected to a chlorinated aromatic compound purification step. Unreacted benzene was distilled off and recovered from the top of the distillation column at a pressure of 0.1 MPa for the chlorinated aromatic compound purification step, and 365 kg-mol / hr of purified monochlorobenzene (fluid number 9) at 131 ° C. was collected at the bottom of the column. Obtained. Monochlorobenzene having this heat is supplied to a heat exchanger (symbol D), heat exchanged with raw material benzene 1630 kg-mol / hr (fluid number 2) of 40 ° C. supplied from the outside, and the raw material benzene is heated to 1315 KW. While recovering and cooling to 55 degreeC, raw material benzene was heated up to 61 degreeC and supplied to the chlorination process.
Ａ 塩素化工程
Ｂ 塩素化芳香族化合物濃縮工程
Ｃ 塩素化芳香族化合物精製工程
Ｄ 熱交換器
A Chlorination process B Chlorination aromatic compound concentration process C Chlorination aromatic compound purification process D Heat exchanger
Claims (3)
塩素化工程：芳香族化合物と塩素を反応させ、塩素化芳香族化合物と塩化水素を得る工程
塩素化芳香族化合物精製工程：塩素化工程で得られる反応混合物を精製することにより精製された塩素化芳香族化合物を得る工程 A method for producing a chlorinated aromatic compound comprising the following steps, wherein the aromatic compound supplied to the chlorination step is heated by the heat of the chlorinated aromatic compound obtained in the chlorinated aromatic compound purification step A method for producing a chlorinated aromatic compound.
Chlorination step: A step of reacting an aromatic compound with chlorine to obtain a chlorinated aromatic compound and hydrogen chloride Chlorination aromatic compound purification step: Chlorination purified by purifying the reaction mixture obtained in the chlorination step Step of obtaining an aromatic compound
塩素化芳香族化合物濃縮工程：塩素化工程で得られる反応混合液から未反応の芳香族化合物の少なくとも一部を留去させ、反応混合物中の塩素化芳香族化合物の濃度を高める工程 The manufacturing method of Claim 1 which has the following chlorinated aromatic compound concentration process before a chlorinated aromatic compound refinement | purification process.
Chlorinated aromatic compound concentration step: A step of evaporating at least a part of the unreacted aromatic compound from the reaction mixture obtained in the chlorination step to increase the concentration of the chlorinated aromatic compound in the reaction mixture.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109053361A (en) * | 2018-09-11 | 2018-12-21 | 安徽东至广信农化有限公司 | For reducing the method for impurity dichloro-benzenes in benzene chloride production technique |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109053361A (en) * | 2018-09-11 | 2018-12-21 | 安徽东至广信农化有限公司 | For reducing the method for impurity dichloro-benzenes in benzene chloride production technique |
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