JP4420293B2 - Apparatus and method for recovery of acetic acid and catalyst in the production process of 2,6-naphthalenedicarboxylic acid - Google Patents
Apparatus and method for recovery of acetic acid and catalyst in the production process of 2,6-naphthalenedicarboxylic acid Download PDFInfo
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Description
本発明は、ジメチルナフタレンを含酸素気体および酢酸溶媒下でコバルト、マンガンのような遷移金属と臭素系化合物を用いて製造された触媒系を利用して、酸化反応させ、ナフタレンジカルボン酸を製造する連続工程において、酸化工程と結晶化工程、そして固液分離工程を経て排出される母液中、酢酸および触媒を効果的に回収するための装置および方法に関するものである。 The present invention produces naphthalenedicarboxylic acid by oxidizing a dimethylnaphthalene using a catalyst system produced by using a transition metal such as cobalt and manganese and a bromine compound in an oxygen-containing gas and an acetic acid solvent. The present invention relates to an apparatus and a method for effectively recovering acetic acid and a catalyst in a mother liquor discharged through an oxidation process, a crystallization process, and a solid-liquid separation process in a continuous process.
一般的に、工程で用いられた酢酸および触媒を回収するために、多様な分離工程を用いることができる。 In general, various separation steps can be used to recover the acetic acid and catalyst used in the step.
通常、酢酸回収工程では、酢酸回収方法として蒸留法を用いているが、経済的な面で不利であり、また、濾過法および吸収法は酢酸と触媒を分離するのに適していないといえる。したがって、酢酸および触媒を回収するための様々な他の方法が提案されていた。特許文献１は、金属性物質が含まれている酢酸溶液から第３アミンと有機稀釈剤を酢酸の抽出用溶剤として用いた抽出方法による酢酸の回収工程を示している。しかし、このような方法は、ナフタレンジカルボン酸の製造工程における酢酸と触媒を回収する方法としては適していない。これは、抽出を用いる方法では、酢酸の分離回収後、後処理工程が行われるべきで、抽出用溶剤と酸化反応触媒の反応性を考慮しなければならないためである。 Usually, in the acetic acid recovery step, a distillation method is used as an acetic acid recovery method, but it is disadvantageous in terms of economy, and it can be said that the filtration method and the absorption method are not suitable for separating acetic acid and the catalyst. Accordingly, various other methods for recovering acetic acid and catalyst have been proposed. Patent Document 1 shows a process of recovering acetic acid by an extraction method using a tertiary amine and an organic diluent as an acetic acid extraction solvent from an acetic acid solution containing a metallic substance. However, such a method is not suitable as a method for recovering acetic acid and a catalyst in the production process of naphthalenedicarboxylic acid. This is because in the method using extraction, a post-treatment step should be performed after acetic acid separation and recovery, and the reactivity of the extraction solvent and the oxidation reaction catalyst must be taken into consideration.
触媒の回収方法としては、焼却法、真空濾過法、電気化学法などがあるが、まだ商用化されていない状態である。
本発明は、上述した先行技術の問題点および短所を解決するために、ナフタレンジカルボン酸の製造工程において排出される母液中、酢酸と触媒を最も経済的で、かつ効率的に回収する装置および方法を提供する。 In order to solve the above-mentioned problems and disadvantages of the prior art, the present invention is an apparatus and method for recovering acetic acid and a catalyst most economically and efficiently in a mother liquor discharged in the production process of naphthalenedicarboxylic acid. I will provide a.
本発明は、前記目的を達成するために、ナフタレンジカルボン酸の製造工程において排出される母液中、酢酸および触媒を回収するための装置および方法を提供する。 In order to achieve the above object, the present invention provides an apparatus and method for recovering acetic acid and a catalyst in a mother liquor discharged in a process for producing naphthalenedicarboxylic acid.
本発明の適切な実施形態によると、ナフタレンジカルボン酸の製造工程において排出される酢酸、触媒およびその他有機物を含む母液から酢酸および触媒回収用装置であって、母液または苛性ソーダを投入するための投入口、酢酸排出口、および触媒および有機物排出口を備える母液受容部と、前記母液受容部を加熱するための加熱手段と、前記触媒および有機物排出口に連結して、触媒を有機物から分離するための下部の濾過膜と、前記母液受容部の内部を攪拌するための攪拌機を含む酢酸および触媒回収用装置が提供されている。 According to a suitable embodiment of the present invention, there is provided an apparatus for recovering acetic acid and catalyst from a mother liquor containing acetic acid, a catalyst and other organic substances discharged in the production process of naphthalene dicarboxylic acid, and an inlet for charging the mother liquor or caustic soda An acetic acid outlet, and a mother liquor receiving portion having a catalyst and organic matter outlet, a heating means for heating the mother liquor receiving portion, and connected to the catalyst and organic matter outlet to separate the catalyst from the organic matter. There is provided an apparatus for acetic acid and catalyst recovery including a lower filtration membrane and a stirrer for stirring the inside of the mother liquor receiving part.
本発明の他の適切な実施形態によると、前記加熱手段は、母液受容部の外壁に装着された蒸気投入口および凝縮水放出口を備えるジャケットであることを特徴とする。 According to another suitable embodiment of the present invention, the heating means is a jacket provided with a steam inlet and a condensed water outlet attached to the outer wall of the mother liquor receiving part.
本発明のまた他の適切な実施形態によると、前記母液受容部は苛性ソーダ投入口をさらに含むことができる。 According to still another suitable embodiment of the present invention, the mother liquor receiving part may further include a caustic soda inlet.
本発明のまた他の適切な実施形態によると、前記酢酸および触媒回収用装置は、円錐形または円錐台形であることを特徴とする。 According to still another suitable embodiment of the present invention, the acetic acid and catalyst recovery device is conical or frustoconical.
本発明のまた他の適切な実施形態によると、前記下部の濾過膜は真空度５０〜１５０ｍｍＨｇ（０．０６７〜０．２ｂａｒ）、総濾過面積０．３〜０．７ｍ２、および濾過膜のふるい目の開き２０〜８０μｍであることを特徴とする。 According to still another suitable embodiment of the present invention, the lower filtration membrane has a degree of vacuum of 50 to 150 mmHg (0.067 to 0.2 bar) , a total filtration area of 0.3 to 0.7 m 2 , and a filtration membrane. The opening of the sieve is 20 to 80 μm.
本発明のまた他の適切な実施形態によると、ナフタレンジカルボン酸の分離工程において排出される母液から酢酸および触媒の回収方法であって、ナフタレンジカルボン酸の分離工程後に排出される母液を受容するステップと、前記受容された母液を加熱して、酢酸を気体状態として回収するステップと、酢酸を回収して残った残余物に苛性ソーダを投入し、沈殿した触媒を分離して回収するステップとからなるナフタレンジカルボン酸の分離工程後に排出される母液から酢酸および触媒を回収する方法が提供されている。 According to still another suitable embodiment of the present invention, a method for recovering acetic acid and catalyst from a mother liquor discharged in a naphthalenedicarboxylic acid separation step, the step of receiving the mother liquor discharged after the naphthalenedicarboxylic acid separation step And heating the received mother liquor to recover the acetic acid in the gaseous state, and recovering the acetic acid, charging the remaining residue with sodium hydroxide and separating and recovering the precipitated catalyst. There is provided a method for recovering acetic acid and catalyst from the mother liquor discharged after the naphthalenedicarboxylic acid separation step.
本発明のまた他の適切な実施形態によると、前記苛性ソーダは残余酢酸に対して２〜３倍重量％で投入することができる。 According to still another suitable embodiment of the present invention, the caustic soda may be added at a 2-3% by weight with respect to the residual acetic acid.
本発明のまた他の適切な実施形態によると、前記触媒回収のために、真空濾過法を用いることを特徴とする。 According to still another suitable embodiment of the present invention, a vacuum filtration method is used for the catalyst recovery.
本発明のまた他の適切な実施形態によると、本発明の方法は、上記で提示した酢酸および触媒回収用装置を用いて、全体が一体化された一つの工程からなる。ここで、一体化された一つの工程とは、酢酸および触媒を回収する一連の工程が別途の分離された装置を用いず、一つの装置で行われることをいう。 According to yet another suitable embodiment of the present invention, the method of the present invention consists of a single integrated process using the acetic acid and catalyst recovery apparatus presented above. Here, one integrated process means that a series of processes for recovering acetic acid and a catalyst is performed in one apparatus without using a separate apparatus.
本発明による酢酸および触媒の回収装置は、酢酸および触媒を、従来と異なり、一連の工程が一つの装置を用いて行われることができるため、工程上で便利であるという長所がある。また、別途の精製工程なしに、リサイクル可能な酢酸および触媒を回収でき、非常に経済的である。 The acetic acid and catalyst recovery apparatus according to the present invention has an advantage in that the acetic acid and the catalyst can be conveniently used in a process because a series of processes can be performed using a single apparatus unlike the conventional apparatus. In addition, recyclable acetic acid and catalyst can be recovered without a separate purification step, which is very economical.
以下、本発明の一実施例の概略図である図１に基づき、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail with reference to FIG. 1 which is a schematic diagram of one embodiment of the present invention.
母液受容部Ａの上部には母液投入口１が備えられており、ナフタレンジカルボン酸の製造工程において排出される母液を受容する。前記受容された母液は、外部加熱手段によって加熱され、この時、酢酸は気化して酢酸排出口３に排出される。酢酸が排出して残った残余物は触媒およびその他有機物からなり、前記残余物に苛性ソーダを投入して触媒を沈殿させる。前記苛性ソーダは、別途の投入口６で投入されることもできるが、母液投入口１で投入されることもできる。前記沈殿した触媒は、触媒および有機物排出口２を介して排出された後、下部の濾過膜７を介して有機物と分離・回収される。
A mother liquor inlet 1 is provided in the upper part of the mother liquor receiving part A, and receives the mother liquor discharged in the production process of naphthalenedicarboxylic acid. The received mother liquor is heated by an external heating means, and at this time, acetic acid is vaporized and discharged to the acetic acid outlet 3. The residue remaining after the acetic acid is discharged is composed of a catalyst and other organic substances, and caustic soda is added to the residue to precipitate the catalyst. The caustic soda can be charged at a separate charging port 6 or can be charged at a mother liquor charging port 1. The precipitated catalyst is discharged through the catalyst and the organic matter discharge port 2 and then separated and recovered from the organic matter through the
母液受容部には母液および触媒含有残余物などの攪拌のための攪拌機Ｂを備え、前記攪拌機は好ましくはアンカー型（Anchor）である。 The mother liquor receiving part is provided with a stirrer B for stirring the mother liquor and the catalyst-containing residue, and the stirrer is preferably an anchor type.
前記母液加熱手段として、例えば熱量供給口の役割をする蒸気投入口４に１７０〜１９０℃の蒸気を投入し、母液受容部内の母液を加熱し、投入された蒸気は凝縮されて下部凝縮水排出口５で放出される。
As the mother liquor heating means, for example, steam at 170 to 190 ° C. is poured into the steam inlet 4 serving as a calorie supply port, the mother liquor in the mother liquor receiving part is heated, and the introduced steam is condensed and discharged from the lower condensed water. It is discharged at the
ジメチルナフタレンをナフタレンジカルボン酸に酸化させるのに使われる触媒として、コバルト成分、マンガン成分および臭素成分の組合からなる複合触媒系を用いるが、ここでコバルト成分として用いることができる化合物は、コバルトアセテート、コバルトナフタレートおよびコバルトカーボネートなどで、前記コバルト成分の量は、ジメチルナフタレンに対するコバルト原子の比率で０．０２〜０．１５、好ましくは０．０４〜０．１２で、より好ましくは０．０６〜０．１である。 As a catalyst used to oxidize dimethylnaphthalene to naphthalenedicarboxylic acid, a composite catalyst system comprising a combination of a cobalt component, a manganese component and a bromine component is used. Here, a compound that can be used as a cobalt component is cobalt acetate, In cobalt naphthalate and cobalt carbonate, the amount of the cobalt component is 0.02 to 0.15, preferably 0.04 to 0.12, more preferably 0.06 to 0.12 in terms of the ratio of cobalt atoms to dimethylnaphthalene. 0.1.
マンガン成分として用いることができる化合物は、マンガンアセテート、マンガンナフタレート、マンガンカーボネートおよびマンガン臭化物であり、マンガン成分の量は、コバルト原子を基準として０．０５〜１．０、好ましくは０．１５〜０．４である。総金属触媒の量、すなわちコバルトとマンガン成分の和が原子を基準としてジメチルナフタレンに対し０．０３〜０．２５、好ましくは０．０５〜０．２である。前記範囲を外れるようになると、所望の高純度のナフタレンジカルボン酸を得ることができないが、コバルト成分とマンガン成分をあまりにも少なく用いた場合、酸化反応の中間物質である２，６−ホルミルナフトエ酸の転換がなされず、最終目的生産物の収率が落ちるようになり、あまりにもたくさん用いた場合、不純物であるトリメリット酸と錯体を形成してナフタレンジカルボン酸の純度が下がる。 The compounds that can be used as the manganese component are manganese acetate, manganese naphthalate, manganese carbonate and manganese bromide, and the amount of the manganese component is 0.05 to 1.0, preferably 0.15 to 0.15 based on the cobalt atom. 0.4. The amount of the total metal catalyst, that is, the sum of the cobalt and manganese components is 0.03 to 0.25, preferably 0.05 to 0.2, based on atoms with respect to dimethylnaphthalene. If it goes out of the above range, the desired high-purity naphthalenedicarboxylic acid cannot be obtained. However, when too little cobalt component and manganese component are used, 2,6-formylnaphthoic acid which is an intermediate substance in the oxidation reaction In other words, the yield of the final target product is lowered, and when it is used in a large amount, it forms a complex with trimellitic acid as an impurity, and the purity of naphthalenedicarboxylic acid is lowered.
臭素成分の提供のために、臭化マンガン、臭化コバルト、臭化ナトリウム、臭化アンモニウムおよびテトラブロモエタンからなる群から選択された１種以上の化合物を用いることができ、臭素成分の比率は、コバルト原子を基準として０．８〜２．０、好ましくは１．０〜１．５である。前記範囲を超える臭素成分を用いる場合、最終的に誘導されるナフタレンジカルボン酸の遷移金属錯体の量は減少するが、臭素化合物の量が増加し、精製工程の負荷が増加して、色を帯びる不純物が増加するため好ましくない。また、臭素成分を再使用する工程を採用する場合、回収工程の必要のため、付加的な経済的損失が発生する。一方、上記範囲未満の臭素成分を用いる場合、ナフタレンジカルボン酸中の遷移金属錯体の量が増加するようになる。 For providing the bromine component, one or more compounds selected from the group consisting of manganese bromide, cobalt bromide, sodium bromide, ammonium bromide and tetrabromoethane can be used, and the ratio of the bromine component is And 0.8 to 2.0, preferably 1.0 to 1.5, based on the cobalt atom. When a bromine component exceeding the above range is used, the amount of the finally derived naphthalenedicarboxylic acid transition metal complex is decreased, but the amount of the bromine compound is increased, the load of the purification process is increased, and the color is tinged. Impurities increase, which is not preferable. Further, when a process for reusing the bromine component is employed, an additional economic loss occurs due to the need for a recovery process. On the other hand, when a bromine component less than the above range is used, the amount of transition metal complex in naphthalenedicarboxylic acid increases.
反応物、すなわちジメチルナフタレンを酢酸に１：５〜１：１５の比率で溶解させ、好ましくは１：１０〜１：１２の比率内で溶解させて、酸化反応機に投入する。 The reactant, i.e. dimethylnaphthalene, is dissolved in acetic acid in a ratio of 1: 5 to 1:15, preferably dissolved in a ratio of 1:10 to 1:12, and charged into the oxidation reactor.
前記酸化反応工程を経た生成物は、結晶化工程を通過しながら、一定の大きさの結晶を有する固相分と酢酸のスラリ状で固液分離工程に移送され、分離工程装置によって、固相分の生成物と母液、すなわち触媒および有機物が含まれている酢酸溶液に分離する。本発明は、固液分離工程を経た母液中、酢酸と触媒を効果的な方法で分離することを特徴とする。 The product that has undergone the oxidation reaction step is transferred to the solid-liquid separation step in the form of a solid phase component having a certain size of crystals and acetic acid while passing through the crystallization step, and is separated by a separation step apparatus. The product and mother liquor are separated into an acetic acid solution containing catalyst and organics. The present invention is characterized in that acetic acid and a catalyst are separated by an effective method in a mother liquor that has undergone a solid-liquid separation step.
本発明の酢酸および触媒の回収装置により、酢酸は熱量媒体である蒸気を投入して蒸発により回収し、蒸発されていない溶液中の触媒は苛性ソーダを投入して触媒を沈殿させた後、真空濾過法を用いて回収する。 With the acetic acid and catalyst recovery apparatus of the present invention, acetic acid is recovered by evaporation by adding steam, which is a calorimetric medium, and the catalyst in the solution that has not been evaporated is charged with caustic soda to precipitate the catalyst, followed by vacuum filtration. Recover using the method.
本発明の酢酸および触媒回収用装置は、酢酸蒸発のための母液加熱手段として熱量媒体を用いるために、外壁にジャケットを装着することが好ましい。 In the acetic acid and catalyst recovery apparatus of the present invention, a jacket is preferably attached to the outer wall in order to use a calorimetric medium as a mother liquor heating means for evaporating acetic acid.
また、苛性ソーダは、残っている酢酸と有機物を中和させるのに適するように、残余酢酸に対し２〜３倍重量％を投入することが望ましい。 Moreover, it is desirable to add caustic soda in an amount of 2 to 3 times by weight with respect to the remaining acetic acid so as to be suitable for neutralizing the remaining acetic acid and organic matter.
また、真空濾過法に用いられる濾過膜の総濾過面積は、０．３〜０．７ｍ２、ふるい目の開きは２０〜８０μｍとし、真空度は５０〜１５０ｍｍＨｇ（０．０６７〜０．２ｂａｒ）を保持させることが好適である。 The total filtration area of the filtration membrane used in the vacuum filtration method is 0.3 to 0.7 m 2 , the sieve opening is 20 to 80 μm, and the degree of vacuum is 50 to 150 mmHg (0.067 to 0.2 bar). It is preferable to hold.
以下では、実施例によって本発明をさらに詳細に説明するが、この実施例が本発明を限定しているものではない。 Hereinafter, the present invention will be described in more detail by way of examples. However, the examples do not limit the present invention.
［実施例１］
冷却機、加熱機、攪拌機および再循環酢酸ドラムを備える３００Ｌのチタニウム酸化反応機に、表１のような組成比の触媒と反応物を共に投入する。
[Example 1]
A 300-liter titanium oxidation reactor equipped with a cooler, a heater, a stirrer, and a recirculating acetic acid drum is charged with a catalyst and a reactant having the composition ratio shown in Table 1.
反応温度は２００℃で、反応圧力は２０ｋｇ／ｃｍ２に調節した後、攪拌機を７００ｒｐｍに設定し、投入される反応気体が適切に分散されるようにする。酢酸に対するジメチルナフタレンの重量比が１０％である反応溶液を、触媒と共に９３ｋｇ／ｈｒの速度で供給しながら連続的に反応を進行させる。 After adjusting the reaction temperature to 200 ° C. and the reaction pressure to 20 kg / cm 2 , the stirrer is set to 700 rpm so that the reaction gas to be introduced is properly dispersed. The reaction proceeds continuously while supplying a reaction solution having a weight ratio of dimethylnaphthalene to acetic acid of 10% together with the catalyst at a rate of 93 kg / hr.
反応後、結晶化工程および分離工程を経て排出された母液を酢酸および触媒の回収装置に注入する。酢酸および触媒の回収装置は、内部容積が１０７Ｌであるステンレス材で、外壁には熱量を供給する媒体が移動するジャケットからなり、内部はアンカー型の攪拌機が設置されている。熱量を供給する媒体としては、１０気圧の蒸気を用いて、酢酸が７０％以上蒸発するまで供給する。酢酸蒸発後、温度を６０℃で維持しながら、苛性ソーダ５０Ｌを投入する。２時間ぐらい経過した後、触媒および有機物排出口に濾過機および真空ポンプを連結して有機物と溶液を濾過させ、残った触媒を回収する。 After the reaction, the mother liquor discharged through the crystallization step and the separation step is injected into a acetic acid and catalyst recovery device. The acetic acid and catalyst recovery device is made of stainless steel having an internal volume of 107 L. The outer wall is made of a jacket through which a medium for supplying heat moves, and an anchor type stirrer is installed inside. As a medium for supplying heat, steam at 10 atm is supplied until acetic acid evaporates 70% or more. After evaporation of acetic acid, 50 L of caustic soda is added while maintaining the temperature at 60 ° C. After about 2 hours, a filter and a vacuum pump are connected to the catalyst and organic matter discharge ports to filter the organic matter and the solution, and the remaining catalyst is recovered.
コバルト触媒金属回収率は９５％、マンガン触媒金属回収率は９０％、臭素回収率は１０％、そして酢酸回収率は６５％の結果を得た。 The cobalt catalyst metal recovery rate was 95%, the manganese catalyst metal recovery rate was 90%, the bromine recovery rate was 10%, and the acetic acid recovery rate was 65%.
上記の実施例によると、本発明の装置によって、酢酸および触媒を回収する場合、経済的に非常に有利であるということを確認することができる。 According to the above embodiment, it can be confirmed that the apparatus of the present invention is very advantageous economically when acetic acid and catalyst are recovered.
Ａ 母液受容部
Ｂ 攪拌機
１ 母液投入口
２ 触媒および有機物排出口
３ 酢酸排出口
４ 蒸気投入口
５ 凝縮水排出口
６ 苛性ソーダ投入口
７ 下部の濾過膜
A Mother liquid receiving part B Stirrer 1 Mother liquid inlet 2 Catalyst and organic substance outlet 3 Acetic acid outlet 4
Claims (9)
母液または苛性ソーダを投入するための投入口、酢酸排出口、および触媒および有機物排出口を備える母液受容部と、
前記母液受容部を加熱するための加熱手段と、
前記触媒および有機物排出口に連結して、触媒を有機物から分離するための下部の濾過膜と、
前記母液受容部の内部を攪拌するための攪拌機とを含む酢酸および触媒回収用装置。 An apparatus for recovering acetic acid and catalyst from a mother liquor containing acetic acid, catalyst and other organic matter discharged in the production process of 2,6-naphthalenedicarboxylic acid,
A mother liquor receiving portion comprising an inlet for introducing mother liquor or caustic soda, an acetic acid outlet, and a catalyst and organic matter outlet;
Heating means for heating the mother liquor receiving part;
A lower filtration membrane for separating the catalyst from the organic matter connected to the catalyst and the organic matter outlet;
A device for recovering acetic acid and catalyst, comprising a stirrer for stirring the inside of the mother liquor receiving part.
２，６−ナフタレンジカルボン酸の分離工程後、排出される母液を受容するステップと、
前記受容された母液を加熱して、酢酸を気体状態に回収するステップと、
酢酸を回収して残った残余物に苛性ソーダを投入し、沈殿した触媒を分離して回収するステップとからなる２，６−ナフタレンジカルボン酸の分離工程後に排出される母液から酢酸および触媒の回収方法。 A method for recovering acetic acid and a catalyst from a mother liquor discharged in a separation step of 2,6-naphthalenedicarboxylic acid,
Receiving the mother liquor discharged after the separation process of 2,6-naphthalenedicarboxylic acid;
Heating the received mother liquor to recover acetic acid in a gaseous state;
A method for recovering acetic acid and catalyst from a mother liquor discharged after the separation process of 2,6-naphthalenedicarboxylic acid, comprising the steps of recovering acetic acid and adding caustic soda to the remaining residue and separating and recovering the precipitated catalyst .
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