1261587 (1) 九、發明說明 相關申請案之參照 本申請案係2 0 0 4年八月9日提出申請的申請案序號 10/915,723之後續申請案，該案主張2004年3月24日申 請的臨時專利申請案序號第60/5 5 6,2 3 6號在35. U.S.C. § 1 19(e)下之優先權。 φ 【發明所屬之技術領域】 本發明係有關製造高純度酚之領域。更特定言之，本 發明係有關從酚去除乙醯甲醇以獲得合意的高純度。 【先前技術】 常用於製造酚的方法包含將異丙苯氧化爲氫過氧化異 丙苯，接著其酸催化分解爲酚與丙酮。從反應產物離析酚 係包含酸催化劑的中和，接著一系列蒸餾與分離步驟。較 # 低沸點成分，例如丙酮，未反應的異丙苯與（X-甲基苯乙烯 (AMS)首先藉由蒸餾從粗製產物回收。剩餘物質係經導引 至酚回收管柱中，於其中從較高沸點雜質蒸餾出酚。取決 於回收丙酮、異丙苯、與AMS所用的蒸餾程序者，蒸餾 出的酚除了殘餘量的丙酮、異丙苯與AMS之外，可能還 包含少量雜質，例如異亞丙基丙酮（mesityl oxide，MO) 、乙醯甲醇（羥基丙酮）、及其他脂族羰基化合物、烯烴 化合物、苯乙酮、異丙苯酣（cum yip hen 〇1)、與2 -和3-甲基苯并呋喃（MBF )。此等雜質在某些應用，例如於雙 1261587 Μ B F /系其些應吊例雙酚 ι聚碳酸雙脂：Ζ.—種前驅 _ 3製造二乐，¾ _的特刮方亘2::亏染物：主於有類·的 :喔發生 黑：5:藉主一鐘從酚一離二 V〖1R F .美圏專i ::筚 ::.;J 6 4」U 7號與第4 m、ί 5 :i號描述一種有π的蒸餾法.、也 稱彳乍蒸氣汽提 i s t e a m. s t r i ρ ρ 1 n g )，以減少酚Φ之]y[ B F : 不過，甶於高能量成本且需要使用大型蒸餾塔，就資本投 Φ 資與作業成本而言，此方法係昂貴者。美國專利第 5，4 14,154號描述使用強酸離子交換樹脂藉由轉換其成爲 較高沸點化合物以減少MBF含量。美國專利第5,414，154 號也說明藉由樹脂處理去除MBF的效用性會隨著溫度增 加而增加。 儘管強酸離子交換樹脂也藉由接觸從酚去除羰基化# 物，不過乙醯甲醇會與酚反應而產生更多MBF。美國專利 桌5,414，154號提出在與樹脂接觸去除MBF之前，從g分去 9 除乙醯甲醇（例如，藉由用胺處理）的必要性。 儘管有效，不過胺處理涉及使用隨後必需從酚流滌除 的昂貴藥劑。 美國專利第3，8 1 0，9 4 6號與第6，4 8 9，5 1 9號揭示對包 含乙醯田醇的酚流使用酸或酸性樹脂去除乙醯甲醇之處理 。英國專利第〇 8 6 5 6 7 7號揭示一種用於從酚流去除乙醯 甲醇的方法，其中係於有或無催化劑之下加熱酚流。不過 在所有這些專利中》係藉由乙醯甲醇與酚反應形成Μ B F 5隨後將MBF由酚流滌除而去除乙醯甲醇。 1261587 . (3) 歐洲專利第〇 〇 〇 4 1 6 8號與美國專利第4，8 5 7，1 5 1號 係揭示可從酚流去除乙醯甲醇的蒸餾方法。不過，此等方 t去涉及使用資本密集之蒸餾裝置。 目前亟須一種藉由形成明顯量的額外Μ B F而對酚產 率沒有不良影響的有效、低成本從酚流去除乙醯甲醇的方 法。 【發明內容】 本發明提供從酚流去除乙醯甲醇的有效低成本的方法 〇 在本發明一具體貫例中，一種用於從酣有效低成本地 去除乙醯甲醇的方法包括將含乙醯甲醇的酚流與一酸性樹 脂在約8 5 ° C或更低的溫度下接觸以轉化乙醯甲醇成爲除 甲基苯并呋喃之外的較高沸點化合物。隨後蒸餾該酚流以 從較高沸點化合物分離出酚。 在本發明另一具體實例中，一種用於有效低成本從酚 去除乙醯甲醇的方法包括在大於約175。(：的溫度下加熱酚 流以轉化乙醯甲醇成爲除甲基苯并呋喃之外的較高沸點化 合物。此可以於有或無添加鹼金屬氫氧化物之下進行。隨 後，蒸餾酚流以從較高沸點化合物分離出酚。 在本發明的這兩個具體實例中，都可以有效去除乙醯 甲醇而大部份的乙醯甲醇沒有與酚反應，因而本發明方法 可導致減低的Μ B F形成及改善的酚產率。 1261587 業經發現者_〒s甲低成工從酚有效去除乙醯33醇同 時使王基苯：货3夫喃 < Μ B F : Ζ形_減到最父：可去除乙醯 丨王醇$處理气括對会：::::.醯® _於莖：餾酚_酸他：樹脂於€涅. π處理或用.少+量苛性劑於高溫下處理。藉S此處理’粗製 酚中之乙醯甲醇先被轉化爲除Μ B F外之高沸點產物。然 後，可經由蒸餾從酚分離出此等高沸點產物。 φ 乙醯甲醇的去除對隨後從粗製酚有效去除MBF具有 關鍵性。如所知者，在轉化MB F成爲可從酚分離出的產 物所用之高溫與酸性條件下，乙醯甲醇會與酚反應產生更 多的MBF。這種反應有雙重效果：減少酚回收率且使得從 產物去除MBF的效率更低。 在本發明一具體實例中，包含乙醯甲醇的蒸餾酚流係 與酸性樹脂在約8 5 ° C或更低的溫度下接觸以轉化乙醯甲 醇成爲除MBF之外的較高沸點化合物。酸性樹脂處理之 • 後’係藉由蒸餾從較高沸點化合物中分離出酚。處理時間 及溫度會基於要從粗製酚去除的乙醯甲醇之量而變異。處 理時間可從5分鐘變異至1小時。在一範例處理中，係藉 由與酸性樹脂在約8 5。c溫度下接觸約1 5分鐘而從粗製酚 流去除70 0 ppm的乙醯甲醇。在此例中，只有約12%的乙 醯甲醇被轉化爲Μ B F。 車乂佳者該酸性樹脂係呈固定床形式，使酚流在其上通 過◦酣流通過樹脂床的速率較佳者爲1至1 2床體積/小時 -7- (5) 1261587 第1圖顯示出用A m b e r 1 y s t 3 6於8 3 ° C下處理 ，將乙醯甲醇由約2 2 5重量p p m快速減少至接近 。可以看到MBF的形成達到最少。如果是要將所 甲醇都轉化爲MBF，則預期會有約400重量ppm 總濃度。反而，2-MBF與3-MBF的組合濃度只有約 量p p m。第2圖再次顯示包含約2 2 5重量p p m乙 的粗製酚流用A m b e r 1 y s t 3 6於8 5 ° C下處理。再度 φ 醯甲醇含量極快速減少至接近0 ppm，而MBF的形 小。如在第2圖中可進一步看出者，延長在85。C 時間不會導致MBF含量的增加。這表示藉由酸性 理從乙醯甲醇生成的重產物在此溫度下係穩定的。 酸性樹脂處理後之蒸餾較佳者爲在減壓下實施 蒸餾（flash distillation )，以避免酸性處理期 的高分子量物種斷裂所致MBF的形成。真空下急 的使用具有額外的優點：排除先前技術方法中分離 # 醯甲醇所用的昂貴蒸餾裝置。不過，應察覺者，可 多種蒸餾法與本發明結合，只要小心避免酸性處理 成的高分子量物種之分解即可。 請參考第3圖，其中闡示避免酸性樹脂處理期 的重產物的分解之必要性。第3圖顯示高溫樹脂處 已用酸性樹脂在8 5。C處理以轉化乙醯甲醇爲較高 合物而沒有先行去除較高沸點產物的酚流之影響。 出者，高溫導致額外Μ B F的形成。這表示在低溫 脂處理中形成的較高沸點化合物在酸性樹脂存在中 酚樣品 0 ppm 有乙醯 的MBF 25 重 醯甲醇 地，乙 成也最 的保持 樹脂處 的急驟 間形成 驟蒸餾 酚與乙 以使用 期間形 間形成 理對於 沸點化 如可看 酸性樹 的高溫 -8- (6) 1261587 下會分解回到乙醯甲醇，且隨後與酚反應而形成M B F。這 不只造成酚損失，而且，如可看出者，也造成爲減少MBF 含量至接近〇重量ppm所需時間的明顯拉長，約爲n〇 分鐘。 第4圖闡示酸性樹脂處理形成的較高沸點化合物在高 溫酸性樹脂處理之則經由I分的急驟蒸|留以去除Μ B F之例 子。如在弟4圖可以看出者，μ B F含量沒有增加。此外， φ MBF含量在約10分鐘，而非130分鐘內減少至接近〇 ppm 〇 在本發明另一具體實例中，包含乙醯甲醇的蒸餾酚流 係在一密閉系統內於高溫下加熱以轉化乙醯甲醇成爲除 MB F之外的較高沸點化合物。該加熱處理可以在有或沒有 添加少量苛性劑之下進行。若該加熱處理係在沒有添加苛 性劑之下進行，則該酚流的pH應該高於2，較佳者高於 2 · 5。通常，此爲來自經中和的反應產物之蒸餾酚流所具 Φ P Η値。較低的p Η可能導致加添量的Μ B F。苛性劑較佳者 係以濃溶液形式添加，例如5 0重量％。再度者，係經由蒸 " 餾而從較高沸點化合物分離出酚。用於加熱處理的溫度爲 至少175至22 5 °C。處理時間、溫度與苛性劑用量（若需要 時）會基於要從酚流去除的乙醯甲醇之量而變異。如圖5 所闡示者，在一範例處理中，係藉由在沒有加任何苛性劑 之下，於198 °C加熱約4小時將1 03 6 ppm的乙醯甲醇加 少到低於1 〇 p p m。於此例中，只有1 %的乙醯甲醇轉化成 爲Μ B F。如圖6中所闡示者，於用2 6 6 p p m的5 0 %苛性劑 (7) 1261587 存在中，只在約2小時內就將1 04 5 ppm的乙醯甲醇減少 到低於1〇 ppm。不過仍然有稍微較高量（〜1.6%)的乙醯甲 醇轉化爲MBF。應指出者，於高溫的有效率乙醯甲醇之去 除需要所處理酚流中有低水含量，例如以酚爲基準低於 1 · 5 %。較佳者，水含量係經減低到約〇 . 1重量％。減少有 機流，特別是酚，的水含量所用的各種方法皆爲技藝中所 知者。下面表1顯示出將乙醯甲醇從1 8 00減少之其他例 表1 藉由用添加的苛性劑之熱處理去除乙醯甲醇 1 800 ppm乙醯甲 醇減至1 0 p p m 5 0%苛性劑濃度 溫度 260 ppm 525 ppm 1100 ppm 1 75° C > 7小時 1 90° C 5小時 5小時 1 98° C 4.5小時 3 .5小時 2.3小時* 於1 .5%水濃度2.75小時1261587 (1) IX. INSTRUCTIONS INSTRUCTIONS RELATED APPLICATIONS This application is a follow-up application to the application No. 10/915,723 filed on August 9, 2004, which claims to be filed on March 24, 2004. The provisional patent application number 60/5 5 6, 2 3 6 is under 35 USC § 1 19(e). φ [Technical Field to Which the Invention Is Along] The present invention relates to the field of producing high purity phenol. More specifically, the present invention relates to the removal of acetamethanol from phenols to achieve desirable high purity. [Prior Art] A method commonly used in the manufacture of phenols involves the oxidation of cumene to isopropylbenzene hydroperoxide, followed by acid-catalyzed decomposition into phenol and acetone. The phenolic system is isolated from the reaction product to contain an acid catalyst for neutralization followed by a series of distillation and separation steps. Compared with #low boiling component, such as acetone, unreacted cumene and (X-methylstyrene (AMS) are first recovered from the crude product by distillation. The remaining material is led to the phenol recovery column, in which Phenol is distilled from higher boiling impurities. Depending on the recovery of acetone, cumene, and the distillation procedure used with AMS, the distilled phenol may contain small amounts of impurities in addition to residual amounts of acetone, cumene and AMS. For example, mesityl oxide (MO), acetamethanol (hydroxyacetone), and other aliphatic carbonyl compounds, olefin compounds, acetophenone, cumene (cum yip hen 〇 1), and 2 - And 3-methylbenzofuran (MBF). These impurities are used in certain applications, such as in the double 1261587 Μ BF / some of them should be suspended bisphenol ι polycarbonate: Ζ. - precursors _ 3 manufacturing two Le, 3⁄4 _ special scraping 亘 2:: Loss of dyes: Mainly in the class · 喔 Black: 5: Borrowing the phenol from the phenol to the second V 〖1R F. 圏 圏 i ::筚: :.;J 6 4"U 7 and 4 m, ί 5 :i describe a distillation method with π. Also known as 彳乍 steam stripping istea m. stri ρ 1 n g), in order to reduce the phenol Φ] y [B F: However, Fu high energy cost and require the use of large distillation columns, in terms of capital investment and operating cost of capital Φ, based expensive by this method. U.S. Patent No. 5,4,14,154 describes the use of strong acid ion exchange resins to reduce MBF content by converting them to higher boiling compounds. U.S. Patent No. 5,414,154 also teaches that the utility of removing MBF by resin treatment increases with increasing temperature. Although the strong acid ion exchange resin also removes the carbonylation from the phenol by contact, the acetonitrile methanol reacts with the phenol to produce more MBF. U.S. Patent No. 5,414,154 teaches the necessity of removing acetamethanol from g (e.g., by treatment with an amine) prior to contacting the resin to remove MBF. Although effective, amine treatment involves the use of expensive pharmaceutical agents that must subsequently be removed from the phenol stream. U.S. Patent Nos. 3,8,0,9,6,6, and 6,4,8,5,9,9, disclose the treatment of the phenolic stream comprising acetaminophen using an acid or an acidic resin to remove acetamethanol. British Patent No. 8 6 5 6 7 7 discloses a process for the removal of acetamethanol from a phenol stream wherein the phenol stream is heated with or without a catalyst. However, in all of these patents, acetonitrile is removed by reacting acetonitrile with phenol to form Μ B F 5 followed by removal of MBF from the phenol stream. 1261587. (3) European Patent No. 4 6 1 4 1 8 8 and U.S. Patent No. 4, 8 5 7, 1 5 1 disclose a distillation method for removing acetamethanol from a phenol stream. However, these parties involve the use of capital-intensive distillation units. There is currently no need for an efficient, low-cost method for removing acetamethanol from phenol streams by forming a significant amount of additional Μ B F without adversely affecting phenol yield. SUMMARY OF THE INVENTION The present invention provides an efficient and low cost method for removing acetamethanol from a phenol stream. In a specific embodiment of the invention, a method for efficiently and inexpensively removing acetamethanol from hydrazine comprises including acetamidine The phenol stream of methanol is contacted with an acidic resin at a temperature of about 85 ° C or lower to convert acetamethanol to a higher boiling point compound other than methyl benzofuran. The phenol stream is then distilled to separate the phenol from the higher boiling compounds. In another embodiment of the invention, a method for efficiently removing acetamethanol from phenol at a low cost comprises greater than about 175. The phenol stream is heated at a temperature of (: to convert acetonitrile to a higher boiling compound other than methyl benzofuran. This can be carried out with or without the addition of an alkali metal hydroxide. Subsequently, the phenol stream is distilled The phenol is separated from the higher boiling point compound. In both of the specific examples of the present invention, acetamidine methanol can be effectively removed and most of the acetamidine methanol does not react with the phenol, so that the method of the present invention can result in reduced ΜBF The formation and improvement of the phenol yield. 1261587 The founder _〒s A low-worker effectively removes acetamyl alcohol from phenol while making Wangji benzene: goods 3 Fu & Μ BF : Ζ _ reduced to the most father: Can be removed from the acetaminophen $ treatment gas to meet:::::.醯® _ in the stem: distillate phenolic acid: resin in the Netherlands. π treatment or use less + amount of caustic agent at high temperature By the treatment of S, the acetic acid in the crude phenol is first converted into a high boiling product other than Μ BF. Then, the high boiling products can be separated from the phenol by distillation. The removal of φ acetonitrile from the subsequent Crude phenol is critical for the effective removal of MBF. As is known, the conversion of MB F becomes Under the high temperature and acidic conditions of the product which can be separated from the phenol, acetonitrile will react with the phenol to produce more MBF. This reaction has a dual effect: reducing the phenol recovery and making the removal of MBF from the product less efficient. In one embodiment of the invention, the distilled phenolic stream comprising acetamethanol is contacted with an acidic resin at a temperature of about 85 ° C or lower to convert the acetamethanol to a higher boiling point compound other than MBF. Resin treatment • After 'removing phenol from higher boiling compounds by distillation. The treatment time and temperature will vary based on the amount of acetamethanol to be removed from the crude phenol. The treatment time can vary from 5 minutes to 1 hour. In an exemplary process, 70 0 ppm of acetamidine methanol is removed from the crude phenol stream by contact with an acidic resin at a temperature of about 85 ° C for about 15 minutes. In this case, only about 12% Ethyl hydrazine is converted to Μ BF. The acne resin is in the form of a fixed bed, and the rate at which the phenol stream passes through the retort through the resin bed is preferably from 1 to 12 bed volumes per hour. 7- (5) 1261587 Figure 1 shows Treatment with A mber 1 yst 3 6 at 8 3 ° C reduced the acetamidine methanol from about 225 ppm by weight to near. It can be seen that the formation of MBF is minimal. If it is to convert all of the methanol to MBF It is expected that there will be a total concentration of about 400 ppm by weight. Conversely, the combined concentration of 2-MBF and 3-MBF is only about ppm. Figure 2 again shows the crude phenol stream containing about 225 ppm by weight of B with A mber 1 yst 3 6 was treated at 8 5 ° C. Once again, the methanol content of φ 醯 was rapidly reduced to nearly 0 ppm, while the shape of MBF was small. As can be further seen in Figure 2, the extension is at 85. C time does not cause an increase in MBF content. This means that the heavy product formed from acetamethanol by acidity is stable at this temperature. The distillation after the treatment with the acidic resin is preferably carried out under reduced pressure to avoid the formation of MBF caused by the breakage of the high molecular weight species in the acidic treatment period. The urgency of use under vacuum has the additional advantage of eliminating the expensive distillation apparatus used to separate # methanol from the prior art methods. However, it should be noted that a variety of distillation methods can be combined with the present invention, as long as care is taken to avoid decomposition of the acid-treated high molecular weight species. Please refer to Fig. 3, which illustrates the necessity of avoiding decomposition of heavy products during the treatment period of the acidic resin. Figure 3 shows the high temperature resin used in the acid resin at 8 5 . The C treatment used a conversion of acetamethanol as a higher compound without the effect of removing the phenol stream of the higher boiling product first. In addition, high temperatures lead to the formation of additional Μ B F . This means that the higher boiling point compound formed in the low temperature grease treatment in the presence of an acidic resin is a phenol sample of 0 ppm with MBF 25 in the presence of an acetonitrile, and the ethylene is also the most retained at the resin to form a quenched phenol and B. The inter-formation formation during use will decompose back to acetamethanol at a high temperature of -8-(6) 1261587, which can be seen as an acid tree, and then react with phenol to form MBF. This not only causes phenol loss, but, as can be seen, also causes a significant increase in the time required to reduce the MBF content to near the 〇 weight ppm, which is about n 〇 minutes. Fig. 4 is a view showing an example in which the higher boiling point compound formed by the acidic resin treatment is subjected to flash distillation via I at the treatment of the high temperature acidic resin; As can be seen in Figure 4, the μ B F content did not increase. In addition, the φ MBF content is reduced to approximately 〇ppm in about 10 minutes instead of 130 minutes. In another embodiment of the invention, the distilled phenol stream comprising acetamethanol is heated at a high temperature in a closed system to convert Ethyl hydrazine is a higher boiling compound other than MB F. This heat treatment can be carried out with or without the addition of a small amount of caustic. If the heat treatment is carried out without the addition of caustic, the pH of the phenol stream should be above 2, preferably above 2.5. Typically, this is the Φ P Η値 from the distilled phenol stream of the neutralized reaction product. A lower p Η may result in an added amount of Μ B F . Preferably, the caustic is added as a concentrated solution, for example, 50% by weight. Again, the phenol is separated from the higher boiling compounds by distillation. The temperature for the heat treatment is at least 175 to 22 5 °C. The treatment time, temperature and amount of caustic (if needed) will vary based on the amount of acetamethanol to be removed from the phenol stream. As illustrated in Figure 5, in an exemplary process, 1 03 6 ppm of acetamethanol was added to less than 1 加热 by heating at 198 °C for about 4 hours without the addition of any caustic. Ppm. In this case, only 1% of the acetamethanol was converted to Μ B F . As illustrated in Figure 6, in the presence of 2 6 6 ppm of 50% caustic (7) 1261587, 0.45 ppm of acetamethanol was reduced to less than 1 只 in only about 2 hours. Ppm. However, there is still a slightly higher amount (~1.6%) of the conversion of ethylene glycol to MBF. It should be noted that the removal of high-temperature, efficient acetonitrile from methanol requires a low water content in the phenol stream to be treated, for example, less than 1.25 % based on phenol. Preferably, the water content is reduced to about 0.1% by weight. Various methods for reducing the water content of organic fluids, particularly phenols, are known to those skilled in the art. Table 1 below shows other examples of reducing acetonitrile methanol from 1 800. Table 1 by heat treatment with added caustic to remove acetamethanol 1 800 ppm acetamethanol to 10 ppm 50% caustic concentration temperature 260 ppm 525 ppm 1100 ppm 1 75° C > 7 hours 1 90° C 5 hours 5 hours 1 98° C 4.5 hours 3. 5 hours 2.3 hours* at 1.5% water concentration 2.75 hours
在處理去除乙醯甲醇之後，即可從較高沸點化合物蒸 餾出酚，且可於高溫下通過酸性樹脂處理以去除Μ B F，如 美國專利第5,414，154號與第6,388,144 Β1號中所揭示者 ，兩者的全部內容皆以引用方式倂入本文。 -10- (8) 1261587 可從酚去除乙醯甲醇的本發明方法具有比使用蒸餾裝 置，例如，超分流管柱的先前技術方法及使用昂貴胺類的 先前技術方法更具成本效益之優點。此外，本發明方法具 有從要去除的乙醯甲醇產生比利用高濃度苛性劑或依賴用 酸性樹脂做多重高溫處理的先前技術方法更少Μ B F之優 點。 φ 【圖式簡單說明】 第1圖闡示藉由與酸性樹脂於8 3。C下反應以從酚流 去除乙醯甲醇。 第2圖闡示藉由與酸性樹脂於8 5。C下反應以從酚流 去除乙醯甲醇且靜置於85。C不會形成明顯量的MBF。 第3圖闡示當用酸性樹脂於8 5。C下處理過的酚流直 接與酸性樹脂於133 °C下接觸時所發生的MBF之形成。 第4圖闡示在將由乙醯甲醇經由用酸性樹脂低溫處理 • 接著蒸餾而去除之後，藉由與酸性樹脂於134。(：反應從酚 流有效去除MBF。 > 第5圖闡示經由在一密閉系統內於1 9 8。C下加熱以從 酚流有效去除乙醯甲醇。 第6圖闡示經由在一密閉系統內於266 ppm的50%的 苛性劑之存在中在1 9 8 ° C下加熱以從酚流有效去除乙醯甲 醇。 -11 -After the treatment of the removal of the acetamethanol, the phenol can be distilled from the higher-boiling compound and can be treated with an acidic resin at a high temperature to remove the ΜBF, as disclosed in U.S. Patent Nos. 5,414,154 and 6,388,144. The entire contents of both are incorporated by reference. -10-(8) 1261587 The process of the invention which removes acetamethanol from phenol has the advantage of being more cost effective than prior art processes using distillation apparatus, e.g., super-column columns, and prior art processes using expensive amines. In addition, the process of the present invention has the advantage of producing less acetonitrile from the acetonitrile methanol to be removed than prior art processes utilizing high concentrations of caustic or relying on acidic resins for multiple high temperature treatments. φ [Simple description of the drawing] Fig. 1 illustrates the use of 8 3 with an acidic resin. The reaction at C was carried out to remove acetamethanol from the phenol stream. Figure 2 illustrates the use of an acidic resin at 85. The reaction at C was carried out to remove acetamethanol from the phenol stream and to stand at 85. C does not form a significant amount of MBF. Figure 3 illustrates the use of an acidic resin at 85. The phenol flow treated under C directly formed the formation of MBF which occurred when the acidic resin was contacted at 133 °C. Fig. 4 illustrates the use of acetonitrile with an acidic resin at 134 after being treated by low temperature treatment with an acidic resin, followed by distillation. (: The reaction effectively removes MBF from the phenol stream. > Figure 5 illustrates the efficient removal of acetamethanol from the phenol stream via heating in a closed system at 198 C. Figure 6 illustrates the passage through a confinement The system is heated at 198 ° C in the presence of 266 ppm of 50% caustic to effectively remove acetamethanol from the phenol stream. -11 -