TWI224581B - Process for the purification of wash water from the production of aromatic acids - Google Patents
Process for the purification of wash water from the production of aromatic acids Download PDFInfo
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1224581 五、發明說明(1) [技術領域] 本發明領域係關於生產芳香酸之方法,特別係關於改良 芳香酸之製法,其可回收用於製造某些芳香酸損失的產 物、重金屬氧化觸媒及製程水。芳香酸包括但非限於對酞 酸(T A )及間酞酸(I P A )。 [背景技術]1224581 V. Description of the Invention (1) [Technical Field] The field of the present invention relates to a method for producing aromatic acids, in particular to a method for improving aromatic acids, which can recover products and heavy metal oxidation catalysts used for the production of certain aromatic acids. And process water. Aromatic acids include, but are not limited to, terephthalic acid (T A) and isophthalic acid (I P A). [Background technique]
Dickerson等人(美國專利第4,540,493號)揭示一種處理 得自製造對酞酸之洗滌水之方法。該方法包括下列步驟: 洗滌水通過過濾介質而去除未溶解的對酞酸固體,將過濾 後之水通過氫形式之陽離子交換樹脂而去除金屬觸媒,以 及將水通過陰離子交換樹脂來去除溶解的對酞酸及溶解的 有機酸副產物。但此種方法之缺點為使用氫形式之陽離子 I ER可能造成樹脂污垢,原因為氫離子可能與可溶性芳香 酸反應造成其沈澱出而使樹脂污染。陰離子樹脂也消耗相 當量氫氧化鈉來去除芳香酸。又此種方法無法直接回收供 再利用鈷/錳觸媒。希望回收全部洗滌水成分供循環利 用。 [發明之揭示] 本發明為一種改良之純化芳香酸之方法。本發明回收喪 失的芳香酸產物及重金屬氧化觸媒且循環利用純化後的 水。該方法包括下列步驟:過濾而回收不可溶之芳香酸, 離子交換而回收及純化重金屬氧化觸媒,及逆向滲透系統 用以回收水供再度利用。 廢水含有相當大量不可溶的芳香酸。芳香酸可利用習知Dickerson et al. (U.S. Patent No. 4,540,493) discloses a method for treating washing water obtained from the production of terephthalic acid. The method includes the following steps: washing water is passed through a filter medium to remove undissolved terephthalic acid solids, filtered water is passed through a cation exchange resin in the form of hydrogen to remove metal catalysts, and water is passed through an anion exchange resin to remove dissolved Terephthalic acid and dissolved organic acid by-products. However, the disadvantage of this method is that the use of cation I ER in the form of hydrogen may cause resin fouling because the hydrogen ions may react with soluble aromatic acids to cause precipitation and contaminate the resin. Anionic resins also consume equivalent amounts of sodium hydroxide to remove aromatic acids. Furthermore, this method cannot directly recover cobalt / manganese catalyst for reuse. It is desirable to recover all the washing water components for recycling. [Disclosure of the invention] The present invention is an improved method for purifying aromatic acids. The invention recovers lost aromatic acid products and heavy metal oxidation catalysts and recycles purified water. The method includes the following steps: filtration to recover insoluble aromatic acids, ion exchange to recover and purify heavy metal oxidation catalysts, and a reverse osmosis system to recover water for reuse. Wastewater contains a considerable amount of insoluble aromatic acids. Aromatic acids available
第5頁 1224581 五、發明說明(2) 過濾裝置回收,例如 器。較佳方法為連續:回f的管狀過濾器或水平 交叉流動過滹5|特、又又W動過濾器。由無機妊板匕/慮 條件下/效操作條件 過濾滲透液中含有j的粒子。 化觸媒的始及錳。心重金屬為構成氧 鐵、鉻及鎳。金屬係^ /、匕存在的重金屬包括 樹脂之容器被去除。、、、二由將廢水通過含強酸陽離子(SAC) 再生後,強醅陽·雜·^。 含鈷/錳觸媒及置它曹子^脂以水洗滌然後送返再度利用。 交換過程處理而純化”屬雜質的再生物進一步透過離子 回收的鈷/錳觸媒孫★回一收觸媒用以循環至芳香酸製程。 回收:(1)萨$敗t f猎二步驟式方法由再生溶液純化及 出的金屬: 沈丨殿出賤金屬,接著過渡去除沈殿 容器含右一#將鹽水溶液通過容器而去除鈷/錳觸媒,該 下選接種特殊離子交換樹脂(IER)其可於鈉離子存在 媒。·除結/猛觸媒’(3)再生特殊IER而回收鈷/錳觸 適^ ^逆向滲透系統獲得有機酸與水的絶佳分離。滲透液 處i ^於循環至純化過程。保留物含有機鹽類被送至廢物 中^ ί本發明之目的係提供由芳香酸製造中產生的洗滌水 有政回收芳香酸產物。 ^發明之又一目的係提供有效回收金屬觸媒。 發明也有—目的係提供有效回收洗滌水。Page 5 1224581 V. Description of the invention (2) Filter device recovery, such as filter. The preferred method is continuous: a tubular filter returning to f or a horizontal cross-flow through the 滹 5 | special and moving filter. Filter the particles containing j in the permeate by the inorganic pregnancy plate. The beginning of the catalyst and manganese. Heart heavy metals are iron oxide, chromium and nickel. Metal containers and / or heavy metals including resins were removed from the container. After the wastewater is regenerated by strong acid cations (SAC), the strong, strong, and strong impurities are generated. Cobalt / manganese-containing catalyst and Caozi ^ fat are washed with water and then returned for reuse. The regenerated organisms that are impurities that are purified by the exchange process are further passed through the cobalt / manganese catalyst recovered by the ion. The catalyst is recovered and recycled to the aromatic acid process. Recovery: (1) Two-step method of tf hunting The metal purified and regenerated from the regeneration solution: Shen 丨 Dian out of the base metal, and then the Shen Dian container containing the right one # is passed through the salt solution to remove the cobalt / manganese catalyst. The next step is to inoculate a special ion exchange resin (IER) which can be used in Sodium ions are present in the media. • Dejunction / catalyst '(3) Regeneration of special IER and recovery of cobalt / manganese catalyst ^ ^ Reverse osmosis system to obtain excellent separation of organic acids and water. The permeate is circulated to the purification process The retentate contains organic salts and is sent to the waste ^ The object of the present invention is to provide the aromatic acid product to be recycled by the washing water produced in the production of aromatic acid. Another object of the invention is to provide an effective metal catalyst recovery. The invention also has-the purpose is to provide effective recovery of washing water.
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此等及其它本發明之目的及優點由去#你 > 笑'5田号慮後文較佳具體例 之詳細說明合併附圖將顯然易明,附圖說明如 [圖式之簡單說明]These and other objects and advantages of the present invention are described by going to # 你 > 笑 '5 田 号 in the following detailed description of the preferred specific examples. The accompanying drawings will be clearly legible, and the description of the drawings is as follows [Simplified description of the drawings]
圖1為本發明之改良方法之概略流程圖,說明方法步 7 :(1)過遽而回收不溶性芳香酸,(2)離子交換而回收及 、、屯化重金屬氧化觸媒以及(3)逆向滲透而回收水供再度利 二,圖2為廢水處理方法之細節流程圖;圖3為於三步驟式 方法純化被回收的鈷/錳觸媒之觸媒回收方法之細節流程 圖:(1)藉由調整pH值沈澱賤金屬,接著過濾而去除沈澱 出的金屬,(2)藉將鹽水通過容器而由鹽水溶液中移出鈷/ 猛觸媒,该容器含有一種特用離子交換樹脂(IER),其可 於鈉離子存在下選擇性去除鈷/錳觸媒,(3)再生特用離子 父換樹脂而回收錄/猛觸媒。 [實施本發明之最佳模式]Figure 1 is a schematic flow chart of the improved method of the present invention, illustrating method step 7: (1) recovery of insoluble aromatic acids by tritium, (2) recovery and recovery of ion exchange, heavy metal oxidation catalyst, and (3) reverse The infiltration and recovery of water supply is beneficial again. Figure 2 is a detailed flowchart of the wastewater treatment method; Figure 3 is a detailed flowchart of the catalyst recovery method for purifying the recovered cobalt / manganese catalyst in a three-step method: (1) Base metals are precipitated by adjusting the pH, followed by filtration to remove the precipitated metals. (2) The cobalt / catalyst is removed from the saline solution by passing brine through a container containing a special ion exchange resin (IER). It can selectively remove cobalt / manganese catalysts in the presence of sodium ions. (3) Regenerating special ion-exchange resins to recover recording / violent catalysts. [Best Mode for Carrying Out the Invention]
參照圖1說明本發明之較佳具體例。本發明為一種純化 芳香酸純化過程中產生的芳香酸洗滌水之改良裝置及方 法。本發明回收損失的芳香酸產物及重金屬氧化觸媒以及 循環純化後的水。如圖1所述,來自芳香酸純化過程(圖令 未顯示)之廢洗滌水2 0首先於過濾系統1 0過濾而回收不溶 性芳香酸2 1,然後採用離子交換回收過程11來回收及純化 重金屬氧化觸媒1 2,及最後,逆向滲透系統1 3來回收純化 後的水1 4供再度利用。 该方法之較佳具體例細節顯不於圖2及3。得自芳香酸純 化過程之廢洗滌水2 〇含有相當量的不溶性芳香酸2 1。不溶A preferred specific example of the present invention will be described with reference to FIG. The present invention is an improved device and method for purifying aromatic acid washing water produced during the purification of aromatic acid. The invention recovers lost aromatic acid products and heavy metal oxidation catalysts and recycles purified water. As shown in FIG. 1, the waste washing water 2 0 from the aromatic acid purification process (not shown in the drawing) is first filtered in the filtration system 10 to recover the insoluble aromatic acid 2 1, and then the ion exchange recovery process 11 is used to recover and purify the heavy metals. The oxidation catalyst 12 and finally the reverse osmosis system 13 are used to recover the purified water 14 for reuse. The details of the preferred embodiment of this method are not shown in Figs. The waste washing water 2O obtained from the purification process of aromatic acid contains a considerable amount of insoluble aromatic acid 21. Insoluble
第7頁 五、發明說明(4) 性芳香酸21係利用過濾系統1〇 過遽裝置例如可回洗的管狀過遽器或:==!!習知 圖2所广之較佳方法為連續交叉流動過濾器:大過?二。如 f濾器30較佳採用由無機材料製成的膜‘;、又二動 =效於苛刻的作業溫度條件以及酸性 ;:;4:二寺: 為細小粒子。盞她赠Q 7丄 1束什下去除極 非限於攀土、;等另竟材料製成包括例如但 ^屬二;包括但非限於不“的為= 越膜31且由該處循環至循環 f 33循%洗滌水21跨 以,而固體保留懸;;:::3的4交;渗透通過膜 決於若干因素例如粒子大小、漭 笔克^度。浪度取 酸剔除流35被抽取出且送至稠厚哭沈又圈::濃芳香 示),然後循環至芳香酸製程Λ:後 圖中未顯 通過離子交換製程,容後料Γ後不3顆粒的渗透液36 過濾滲透液36含有低濃度重金屬。 媒鈷及錳。除氧化觸媒外也存在構成氧化觸 鎳。金屬係經由將廢水通過含;酸屬上括鐵、鉻及 器40而被去除。較佳強酸陽離;=„)樹脂之容 聚合物。強酸陽離子樹脂由於可^離:二:聯聚苯乙烯 陽離子故為較佳。渗透液36含相杂 |下有效去除 機酸濃度的氣離子。強酸陽離子;脂;將渗透 1224581 五、發明說明(5) ' ---- 酸陽離子樹脂容器4〇引進之前可處於氫或鈉形式。由於經 濟理由故較佳形式為鈉。酸性氯化鈉(食鹽水)溶液為較佳 再生劑。食鹽水溶液於低pH值卜3使用鈉交換重金屬。需 要,pH值來防止重金屬呈金屬氧化物沈澱且污染強酸陽離 子樹脂。SAC樹脂再生後以水清洗然後送至再度利用。另 一種再生SAC樹脂之方法係藉由酸通過SA(:樹脂而將SA(:樹 脂由鈉形式轉成氫形式。 、含有,/錳觸媒及其它重金屬雜質之再生物41進一步透 過離子父換過程處理而純化及回收觸媒用以循環至 製造方法。 鈷/錳觸媒係藉圖3說明之三步驟式方法純化及由再生物 41回收。首先,賤金屬藉由使用苛性蘇打調整再生物41之 PH值而沈澱於容器5〇,接著於賤金屬過濾器5丨藉過濾去除 沈澱的賤金屬。食鹽水溶液52通過賤金屬過濾器51,溶液 中含有鈷/錳觸媒。其次藉由將食鹽水溶液52通過容器” 而由溶液中移出鈷/錳觸媒,容器含有一種可於鈉離子存 在下選擇性去除鈷/錳觸媒之特用離子交換樹脂(IER)。最 後特用離子交換樹脂被再生而回收鈷/錳觸媒5 4。 一沈澱過程係藉添加小量苛性蘇打(Na〇H)6〇至再生物4ι提 鬲PH值至4-5完成。賤金屬呈金屬氧化物沈澱出且藉習知 過濾方法於賤金屬過濾器51被去除。得自賤金屬過濾器5 ^ 之R鹽水溶液5 2之pH值以氫氧化鈉61升高至6 — 7,麸後通 過,用離子交換樹脂容器53來去除鈷/錳觸媒。特用型離 子交換樹脂俗稱螯合離子交換樹脂或選擇性離子交換樹Page 7 V. Description of the invention (4) Aromatic acid 21 is a 10-pass filter using a filtering system such as a backwashable tubular filter or: == !! The preferred method as shown in Figure 2 is continuous Cross Flow Filter: Bigger? two. For example, the f-filter 30 preferably uses a membrane made of an inorganic material, and the second action is effective for severe operating temperature conditions and acidity; 4: two temples are fine particles. She gifted Q 7 丄 1 bundle, which is not limited to climbing the soil, and other materials including, but not limited to, the two; including but not limited to the non-"= = cross membrane 31 and cycle to cycle from there f 33 cycles% washing water 21 spans, while solids remain suspended; :: 4: 4 intersections; penetration through the membrane depends on several factors such as particle size, pen gram degrees. The wave length is taken out by the acid rejection stream 35. Out and sent to the thick crying circle :: strong aroma shown), and then circulate to the aromatic acid process Λ: after the ion exchange process is not shown in the following figure, the volume of the permeate is not 3 particles after the filter 36, the permeate is filtered 36 contains low-concentration heavy metals. Cobalt and manganese. In addition to oxidation catalysts, there are also nickel oxides. Metals are removed by passing wastewater through; acid is iron, chromium, and iron 40. Strong acid ionization is preferred ; = „) Resin content polymer. Strong acid cation resins are preferred because they can be separated: two: crosslinked polystyrene cations. The permeate 36 contains gas ions that effectively remove organic acids. Strong acid cations; lipids; will penetrate 1224581 V. Description of the invention (5) '---- The acid-cation resin container 40 may be in the form of hydrogen or sodium before introduction. For economic reasons the preferred form is sodium. Acidic sodium chloride (saline) solution is the preferred regenerant. The salt solution was exchanged for heavy metals with sodium at low pH. It is necessary to prevent the precipitation of heavy metals as metal oxides and contamination of strong acid cation resins. After the SAC resin is regenerated, it is washed with water and then sent to reuse. Another method of regenerating SAC resin is to convert SA (: resin from sodium form to hydrogen form by acid through SA (: resin). Regeneration 41, containing /, manganese catalyst and other heavy metal impurities is further transmitted through ion exchange. The catalyst is purified and recovered by the process for recycling to the manufacturing method. The cobalt / manganese catalyst is purified by a three-step method illustrated in Figure 3 and recovered by the regenerating 41. First, the base metal is adjusted for regenerating by using caustic soda The pH value of 41 is precipitated in the container 50, and then the base metal filter 5 is used to remove the precipitated base metal. The salt solution 52 passes through the base metal filter 51, and the solution contains a cobalt / manganese catalyst. The salt solution 52 passes through the container "to remove the cobalt / manganese catalyst from the solution. The container contains a special ion exchange resin (IER) that can selectively remove the cobalt / manganese catalyst in the presence of sodium ions. Finally, the special ion exchange resin It is regenerated to recover cobalt / manganese catalyst 5 4. A precipitation process is completed by adding a small amount of caustic soda (NaOH) 60 to the regenerate 4 ι to raise the pH value to 4-5. Base metals are precipitated as metal oxides Borrow and borrow It is known that the filtering method is removed in the base metal filter 51. The pH value of the R salt solution 5 2 obtained from the base metal filter 5 2 is raised to 6-7 with sodium hydroxide 61, passed through the bran, and used an ion exchange resin container. 53 to remove cobalt / manganese catalyst. Special type ion exchange resin is commonly known as chelated ion exchange resin or selective ion exchange tree
1224581 五、發明說明(6) 月曰。適用於本製程之選擇性離子交換樹脂含有官能基例如 但非限於胺基二乙酸,胺基膦酸及聚丙烯酸。然後將氯漠 酸(HBr)溶液62通過離子交換樹脂容器53而由選擇性IER中 移出始/猛。所得回收觸媒溶液54含有觸媒及氫溴酸現在 具有足夠濃度及純度而可送返芳香酸製程。通過選擇性 IER之鹽水溶液63之pH值係以氫氯酸64降低至約! 5 —3且再 度利用於再生SAC樹脂。 參照圖2,得自SAC樹脂容器40之再生物41之邱值典型係 於1· 5-3之範圍。pH值以氫氧化鈉65調整至5 —7。 、 廢洗滌水中溶解的鹽類為多種有機酸之鈉鹽,例如苯甲 酸、間敗酸、對敝酸及對甲苯甲酸。因廢洗條水69通過 ㈣溫度約為75, 洗水69冷部至約25-45 t溫度方便用於逆向渗 ί8〇二【知逆向滲透系統提供有機酸類與洗滌水的絶佳分 離。仔自逆向渗透系統80之渗透液81適合循環至純化過 程。含有有機鹽類之保留物8 2被送至廢物處理(圖中未顯 [不產業應二含低濃度有機酸鹽之廢洗滌水回收率約為85%。 全球每年生產極為大量芳香酸。大 sa m織纖維及食品包裝樹脂及薄 方香酸係於重金屬氧化觸媒存在下經由 八盂 j f甲本及間一甲苯成為對應芳香酸生產畜於、A 程產生技術級產物典型不適合 J因= 過程產生的雜質故。雜質通常為部分氧二:(因對為Λ化1224581 V. Description of Invention (6) Month. Selective ion exchange resins suitable for this process contain functional groups such as, but not limited to, aminodiacetic acid, aminophosphonic acid, and polyacrylic acid. The chlorinic acid (HBr) solution 62 is then removed from the selective IER through the ion exchange resin container 53. The resulting recovered catalyst solution 54 contains the catalyst and hydrobromic acid, and now has sufficient concentration and purity to be returned to the aromatic acid process. The pH of the salt solution 63 by selective IER is lowered to approximately with hydrochloric acid 64! 5-3 and reused for recycled SAC resin. Referring to Fig. 2, the Qiu value of the regenerative 41 obtained from the SAC resin container 40 is typically in the range of 1.5-3. The pH was adjusted to 5-7 with sodium hydroxide 65. 2. The salts dissolved in the waste washing water are sodium salts of various organic acids, such as benzoic acid, meta-acid acid, p-arsolic acid and p-toluic acid. Because the waste strip washing water 69 passes the temperature of about 75, the temperature of the cold part of the washing water 69 to about 25-45 t is convenient for reverse osmosis. The reverse osmosis system provides an excellent separation of organic acids and washing water. The permeate 81 of the osmotic self-reverse osmosis system 80 is suitable for recycling to the purification process. Organic salt-containing retentate 8 2 is sent to waste treatment (not shown in the figure [recycling rate of waste washing water containing low concentration of organic acid salt is about 85%. The world produces extremely large amounts of aromatic acids every year. Large Sam weaving fiber and food packaging resin and thin fragrant acid are in the presence of heavy metal oxidation catalysts through octagonal jf methyl form and m-toluene to correspond to aromatic acids. Production of technical grade products in A and A processes is typically not suitable for J = process production Therefore, the impurity is usually a part of oxygen: (Because the pair is Λ
I 第10頁 1224581 五、發明說明(7) 甲酸,4-羧 質對 技 升高 水溶 香酸 後芳 氫化 質, 送至 媒及 如 化觸 本 圖僅 述之 於由技 術級丁 A 溫度及 液及氫 產物。 香酸藉 雜質溶 以及殘 廢水處 水的損 此存在 媒及洗 發明已 供舉例 本發明 苯曱醛等)及色彩生成物如2, 6-」 術級芳香酸產生的聚合物產物造 及I P A經進一步純化而去除雜質 壓力下溶解於極熱的脫礦物質水 氣隨後通過含氫化觸媒之容器而 然後水溶液冷卻使芳香酸由溶液 習知手段如離心或旋轉真空過濾 解於廢水。該過程產生廢水含有 餘量之芳香酸及重金屬氧化觸媒 理過程,結果導致芳香酸產物、 失。 有一種需要可有效回收芳香酸產 滌水之方式。 經參照某些較佳替代具體例說明 說明之用而絶非限制由隨附之申 之完整範圍。 二羧芴酮。雜 成有害影響。 1將芳香酸於 而去除雜質。 進一步純化芳 中結晶出。然 回收。剩餘的 非期望的雜 。典型廢水被 重金屬氧化觸 物、重金屬氧 ,此等實例意 請專利範圍陳I Page 10 1224581 V. Description of the invention (7) Formic acid, 4-carboxylates are used to raise water-soluble fragrant acid after aromatic hydrogenation, sent to the media and Ruhua Touch. This figure only describes the temperature and temperature of technical grade D A. Liquid and hydrogen products. Fragrant acid is dissolved by impurities and the water in the residual wastewater is damaged. The media and washing have been used to exemplify the present invention, benzaldehyde, etc.) and color products such as 2, 6- "polymer products produced by technical grade aromatic acids and IPA. After further purification to remove impurities, the demineralized water vapor dissolved under extreme pressure is then passed through a container containing a hydrogenation catalyst and then the aqueous solution is cooled, so that the aromatic acid is dissolved in the wastewater by conventional means such as centrifugation or rotary vacuum filtration. This process produces wastewater containing excess amounts of aromatic acids and heavy metal oxidation catalysts, resulting in aromatic acid products and loss. There is a need for a way to efficiently recycle aromatic acids to produce water. The description is illustrated by reference to certain preferred alternatives and is by no means limited to the full scope of the attached application. Dicarboxyfluorenone. Miscellaneous harmful effects. 1 The aromatic acid is removed to remove impurities. Further purification was crystallized from the aromatics. Ran recycling. The remaining unintended miscellaneous. Typical wastewater is oxidized by heavy metals and heavy metal oxygen. These examples are intended to be patented.
第11頁Page 11
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US09/111,103 US5980750A (en) | 1998-07-06 | 1998-07-06 | Process for the purification of waste wash water |
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TWI224581B true TWI224581B (en) | 2004-12-01 |
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