201245137 六、發明說明： 【發明所屬之技術領域】 本發明係關於一種純化由烯系不飽和化合物之氧化臭氧 分解獲得之二羧酸化合物的方法及進行該方法之裝置。 【先前技術】 壬二酸及壬酸之商業化生產已經由氧化裂解油酸中之稀 基（-c=c-)單元而實現。舉例而言，壬二酸已藉由用硫酸 鉻氧化油酸來製備，如美國專利第2,450,858號中所揭示。 然而，因為化學計量使用鉻試劑不合乎需要，所以已開發 更有效之利用臭氧的方法，如美國專利第2,813，113號；第 5,8〇1，275號；第5,883,269號；及第5,973 173號中所揭示 及描述。 基本方法最佳將藉由參考附圖丨中之說明而瞭解，附圖^ 為=示所用設備零件及其在臭氧分解過程中之關係的圖解 流程圖。參考圖1，將油酸供給饋料槽10且接著供給臭氧 吸收器13，其中該油酸與引入臭氧吸收器13中之氧氣/臭 氧氣體混合物之連續流逆流流動。冷卻或冷凉臭氧吸收器 13以實質上控制其中發生之反應的溫度。 臭氧吸收器13藉由循環氧氣之連續封閉系統接收臭氧處 理之氧氣。因&，使用既定部分之氧氣且再使用多次，且 ί統僅需以較小程度抽吸及饋送以使氧含量維持在預定之 :Χ準下。循環氧氣系統包含通向脫水器19之氧源16。氧 器19轉移至臭氧產生器I臭氧產生器使用電流 氧氣轉化成臭氧。臭氧與氧氣之氣態混合物由臭氧 161977.doc 201245137 產生器22流人臭氧吸收器13，在臭氧吸收器中實質上所有 臭氧内含物均由油酸吸收以形成油酸臭氧化物。在油酸臭 氧化物混合物於臭氧吸收器13中之滯留時間期間，混合物 之黏度可提高。若需要，則混合物之黏度可藉由引入相容 性溶劑而降低’如下文所進一步討論。 -旦離開臭氧吸收器13’目前實質上無臭氧之氣體混合 物即會流人靜電集塵器25中，靜電集塵器會移除可在臭氧 吸收器13中吸收之任何細霧狀有機物。純化氣體混合物接 著由靜電集塵器25經由壓氣㈣流入冷卻器31且接著返回 脫水器19中’在脫水器中實質上所有水分均已自氣體混合 物中移除。在冷卻器31與脫水器19之間，可經由臭氧產生 系統閥門34由线獲得或抽取之含氧氣體可供給臭氧化物 分解系統反應器37» 由油酸進行之臭氧之前述吸收會形成油酸臭氧化物，將 其轉移至臭氧化物分解系統反應器37中且用自臭氧產生系 統閥門34抽取之氧氣處理。臭氧化物分解系統反應器可 為適於在液體與氣體之間提供實質界面接觸且可冷卻以調 節反應溫度之任何類型器件。將自臭氧產生系統抽取之氧 氣饋入臭氧化物分解系統反應器37之底部，且在各貯槽中 藉助於機械攪拌器（未圖示）與液體一起攪動。 儘管圖式中僅展示-個整體臭氧化物分解系統反應器 37,但應瞭解反應器37可包含針對獨立溫度、獨立壓力控 制或其兩者組態之不同區域。或者，可視反應器之尺寸、 臭氧化物及其分解產物之流動速率及實現氧氣與所處理液 I61977.doc 201245137 體之間的接觸之攪動效率而定，使用任何數量之反應器。 此外，具有一個以上反應器之替代實施例可以串聯組態、 並聯組態或其兩者來連接。 溫度控制為臭氧化物分解系統反應器37之重要操作參 • 數。更特定言之，必須加熱臭氧化物進料流以達到合適反 、 應溫度，在此溫度下臭氧化物部分在曝露於一或多種催化 劑時可有效進行氧化分解，以優先形成醛及羧酸。臭氧化 物分解催化劑可包括布忍斯特-洛瑞酸（Br0nsted_Lowry )布心斯特-洛瑞驗、路易斯酸（Lewis acid)、路易斯 鹼、金屬或其鹽及脂肪酸鹽（soap)。例示性臭氧化物分解 催化劑可至少部分包括Na、K、B、Sn、Zn、Pt、Pd、 Rh ' Ag ' Mn、Cu、Ni、二氧化鈦/二氧化矽或二氧化欽/ P2〇5複合物及其組合。催化劑可以可溶性物質形式或固體 或載體催化劑形式引入該製程中。 在連到〇適反應溫度之後，醛官能基進一步氧化成羧酸 ^基可以足以產±熱量之速率發生，$熱量&可有助於 提高臭氧化物進料流之溫度。然而，可能需要供應冷卻水 . Y '里度上升超過預定水準。因而，控制溫度以便適用 ‘ 力使臭氧化物轉化成混合氧化產物之有效氧化作用。在圖 1中，未圖示加熱及冷卻裝置。 ，使混合氧化產物由臭氧化物分解系統反應器”流入第一 二單元40 ’其中自，在合氧化產物蒸館壬酸及其他羧酸以 f成第餾出物及混合氧化產物之第一殘餘物。含有壬酸 之第一爾出物在第-冷凝器43中轉化成液體，且接著傳遞 161977.doc 201245137 至粗壬酸儲存槽46中。然而，若需要，則在吸收器13中可 使用一些粗壬酸來稀釋油酸反應物及油酸臭氧化物。因 此’可將可能為粗物質或可進一步純化之壬酸添加至臭氧 吸收器13中以降低吸收器13中臭氧化物之黏度。可用間門 49控制供給吸收器13之再循環壬酸之量。 應注意可使用其他降黏劑及稀釋劑。稀釋劑可為不易與 臭氧反應且與臭氧化物或反應產物相容之已知物質，咬可 為反應產物之一部分。該等稀釋劑包括（但不限於）飽和短 鏈酸，諸如乙酸、丁酸、己酸、庚酸'辛酸、壬酸及癸 酸；酿’諸如乙酸乙酯及乙酸丁酯；及烷烴，諸如己燒、 辛烷及癸烷。然而，推薦使用壬酸，原因在於作為該製程 之最終產物’其不會干擾循環氧氣系統之操作且不需要單 獨蒸餾。換言之，因為壬酸為該製程之最終產物之一所 以其為合適的稀釋劑。 接著將目前汽提掉的相當一部分可用壬酸之混合氧化產 物之第—殘餘物輸送至壬二酸蒸餾單元52，其中蒸餾混合 氧化產物之—部分第一殘餘物以形成第二餾出物，第二餾 出物包括壬二酸及混合氧化產物之第二殘餘物。第二餾出 物藉由4經壬二酸館出物冷凝器55而冷凝形成粗壬二酸， 其轉移至粗壬二酸儲存槽58中。將在蒸餾掉第二餾出物 之後剩餘的混合氧化產物之第二殘餘物或瀝青(pitch)自壬 一酸蒸餾單元52中移出且轉移至殘餘物儲存器61中。混合 氧:匕產物之第二殘餘物可能仍含有一定量之壬二酸，因此 進打進-步加工’若需要，則可回收其中一部分。 161977.doc 201245137 粗壬二酸由粗壬二酸儲存槽58轉移至萃取器64中，在萃 取器中粗壬二酸用熱水（例如約175°F (約80。(：）至約 2HTF(約99。〇)萃取形成壬二酸之熱水溶液q會溶解於 熱壬二酸水溶液中之副產物酸（ΒΡΑ)由萃取器64傾析至 ΒΡΑ儲存器67中。同時，將熱壬二酸水溶液轉移至蒸發器 70中，在其中移除水。接著，將呈熔融形式之壬二酸由蒸 發器70饋人创片機73中’其中溫度降至低於溶點，且接著 將壬二酸之固體薄片輸送至壬二酸儲存箱76中。 儘管上文所述方法及裝置自油酸提供諸如壬二酸及壬酸 之所要產物，但仍存在關於產物之化學純度、人身安全、 系統效率及設備壽命之缺陷。先前技術之程序及裝置之一 種如此缺陷與在不犧牲其總產率之情況下實現壬二酸之高 純度有關。舉例而言，在沸點可能極其類似之情況下粗壬 一酸中之某些雜質，諸如長鏈（例如C14至C18)單羧酸難以 藉由蒸餾移除。視壬二酸之應用而定，單羧酸雜質可能成 問題。舉例而言，在由二羧酸形成長線性聚合物（例如聚 醯胺）期間，單羧酸可充當「鏈終止劑」。因此，需要純化 諸如壬二酸之二羧酸的新穎程序。 【發明内容】 根據本發明之實施例，提供一種純化二羧酸之方法。該 方法包括臭氧處理包含具有6至24個碳之烯系不飽和化合 物與3臭氧氣體之混合物以形成複數種臭氧處理產物在 氧化條件下在合適催化劑存在下裂解該複數種臭氧處理產 物形成混合氧化產物。該等混合氧化產物包含（：2至(：22單 161977.doc 201245137 羧酸與C2至C22二羧酸之混合物。該方法進一步包括蒸餾 混合氧化產物以提供第一餾出物及混合氧化產物之第一殘 餘物。第一餾出物包含C2至（::“單羧酸之混合物，且混合 氧化產物之第一殘餘物包括二羧酸及（^至C22單羧酸之混 合物。該方法進一步包括蒸餾混合氧化產物之第一殘餘物 以提供第二餾出物及混合氧化產物之第二殘餘物，其中第 二餾出物包含二羧酸及C9至C22單羧酸之混合物的餾份； 使第二餾出物分配於水與有機溶劑之間，其中水之溫度在 約175卞（79。〇至約230卞（110。〇之範圍内；其中水與有機 溶劑實質上不可混溶，由此形成含有二羧酸之水層及含有 C9至C22單羧酸混合物之餾份之至少一部分的有機溶劑 層，自水層中分離出有機溶劑層。該方法進一步包括自水 層分離二羧酸以提供C9至C22單羧酸之剩餘含量小於〇 5重 量％之純化二敌酸。 根據本發明之另一實施例，提供由不飽和羧酸產生單羧 酸及二羧酸之方法。該方法包含以下步驟：在臭氧產生器 中產生臭氧氣體；在吸收器中使臭氧氣體與包含不飽和叛 酸之不飽和敌酸饋料接觸獲得臭氧化物；在反應器中使臭 氧化物與氧氣及至少一種催化劑接觸以提供混合氧化產 物，及藉由蒸餾混合氧化產物自該等混合氧化產物分離至 少一部分單羧酸以提供第一餾出物及混合氧化產物之第一 殘餘物’其中該第一餾出物包含單羧酸之餾份且其中該 等混合氧化產物之該第一殘餘物包含二敌酸之館份。該方 法進步包括根據本文所述方法藉由用有機溶劑萃取來純 161977.doc 201245137 化飽和二叛酸。 根據本發明之另一實施例，提供由本文所主張之方法得 到之二羧酸之化學衍生物。 【實施方式】 併入且構成本說明書之一部分的附隨圖式說明本發明之 實施例且與上文給出之本發明之一般描述及下文給出之詳 細描述一起用以描述本發明。 根據本發明之實施例，提供一種純化二羧酸化合物之方 法。該一羧酸係衍生自不飽和羧酸與臭氧接觸獲得臭氧化 :之化學方法。在反應器中將臭氧化物用含氧氣體及至少 種氧化催化劑處理獲得含有單羧酸及二羧酸之混合氧化 產物。羧酸混合物藉由蒸餾第一蒸餾餾份中之至少一部分 單羧酸，由此在混合氧化產物之第一殘餘物中留下二羧2 來純化。混合氧化產物之殘餘物接著經第二蒸餾來蒸餾以 形成第二餾出物及混合氧化產物之第二殘餘物。第二餾出 :包含二羧酸且單羧酸雜質之含量可在約10重量％與約30 量％之間，其中此等雜質之相當一部分不能藉由赛餾自 分有效移除。因而’飽和二缓酸之額外純化受到 包行萃取的影響。混合氧化產物之第二殘餘物 睡括各種焦油及料自至少―種氧化催化劑之金屬脂肪酸 解。合適： 不飽和化合物執行臭氧分 任何數量：和化合物尤其不受其來源限制且可包括 %原子，諸如6至24個碳原子。舉例而言，稀 161977.doc 201245137 系不飽和化合物可包括具有12至20個碳原子之烯系不飽和 化β物。因此，烯系不飽和化合物可具有丨8個碳原子。此 外，烯系不飽和化合物可包括其他官能基，諸如羧酸。烯 系不飽和化合物可衍生自動物或植物來源。因此，烯系不 飽和化合物包括脂肪酸，包括獲自棕櫊油或動物脂之彼等 脂肪酸。在—個實例中，㈣不飽和化合物包括油酸。 在C6至C24烯系不飽和化合物與含臭氧氣體反應之後， 形成複數種臭氧處理產物，其在氧化條件下在合適催化劑 存在下裂解形成混合氧化產物，混合氧化產物包含〇至 C22單羧酸與（：2至022二羧酸之混合物。舉例而言，羧酸 之混合物可包括C2至C16、C5至C9或（：6至（：18單羧酸。舉 例而言’羧酸之混合物可包括C2至C16、C5至⑺或以至 C18二羧酸。根據一個例示性實施例，可對油酸執行臭氧 分解，由此產生壬酸（其為飽和C9單羧酸）及壬二酸（其為飽 和C9二羧酸）。 為了分離諸如壬二酸之所需二羧酸，在第一組蒸餾條件 下蒸餾可由油酸衍生之混合氧化產物以提供包含一部分〇 至C22單羧酸（其可包括壬酸）之第一餾出物及混合氧化產 物之第一殘餘物。氧化產物之第一殘餘物包含所需二幾酸 (例如壬二酸）以及複數種雜質酸，其可包括(：9至(：22單羧 酸之混合物以及其他二叛酸。 混合氧化產物之第一殘餘物隨後在第二組蒸餾條件下經 受第二蒸餾以提供第二餾出物及混合氧化產物之第二殘餘 物。第二餾出物包含所需二綾酸及複數種雜質酸之第一餾 161977.doc •10· 201245137 雜質酸為副產物酸（Βρα)，其可包括C9至〇22單羧酸 之渴*合物。 為了自大批雜質酸中分離壬二酸，進一步加工包括使用 有機溶劑進行水萃取，如τ文所說明。水萃取包括使第二 物勿刀配於水中及/或水與實質上與水不可混溶之有機 之間。因此，使第二餾出物與熱水合併以形成濃的第 傲出物水溶液。若需要’則可將—部分不溶解於濃壬二 ^令液中之副產物酸（ΒΡΑ)自濃水溶液傾析於分離萃取 器或作析中’《後接著用有機溶劑萃取濃水溶液溶離 份’或僅僅轉移至萃取器中β在任—情況下，接著使濃第 餾出物水溶液與有機溶劑混合，其中壬二酸連同複數種 雜質θλ (諸如各種水溶性短鏈（例如匸4至c8)二叛酸）之第二 館伤起保留m亦即水相巾。將有機溶劑可溶性副 產物酸（例如C9至C22單羧酸）萃取至有機溶劑中。 參考圖2，來自儲存槽58之粗壬二酸（㈣第二館出物） 可在熱水槽80中與水合併產生濃的粗壬二酸水溶液，接著 ::其饋入傾析器81中，在傾析器中可自濃水溶液傾析出 邛分不溶解於熱壬二酸水溶液中之副產物酸，之 後轉移至萃取器64中’其中接著使濃水溶液溶離份與有機 溶劑混合。根據一個實施例，可將濃的粗壬二酸水溶液直 接饋入萃取器64中。根據-個實施例，壬二酸萃取器64可 為約克-沙伊貝爾萃取器（Y〇rk_Seheibel extract〇〇 ,其為逆 流、多級、連續液·液萃取器。在―個實施例巾，約克_沙 伊貝爾萃取器具有約1〇至約6〇個分級。舉例而言，約克· I61977.doc 201245137 50或60個或60個 沙伊貝爾萃取器可具有10、20、3〇、4() 以上分級。 π —敗。』洛於熱水中。水之萃取溫度可在約 175FWC)至約2卿⑴代）之範圍β。萃取可在周圍壓 力下或在高壓條件下執行。有機溶劑尤其不限於任何特定 溶劑’但在操作條件下應實質上不可與水混溶。舉例而 言’在20。(：下有機溶劑之水溶性可小於〇5心。此外，在 萃取壓力下，合適有機溶劑之沸點大於萃取水之溫度。 可用於該方法之例示性有機溶劑包括（但不限於）粗二羧 酸中存在之#質可溶於其中2二敌酸實質上不可溶於其令 之脂族或芳族烴溶劑及/或其混合物。該等脂族溶劑之實 例包括（但不限於）直鏈及分支鏈、環狀及非環狀烷烴，諸 如戊烷、己烷、庚烷、辛烷、2,2,4·三甲基戊烷、環戊 烷、環己烷、曱基環戊烷、甲基環己烷；烯烴，諸如戊 烯、己烯、庚烯、環戊烯、環己烯、甲基環戊烯、甲基環 己烯及其類似物；及在室溫及室壓下通常為氣體之液化 烴，諸如液體丙烷及液體丁烷。該等芳族溶劑之實例包括 (但不限於）苯、曱苯及二甲苯。溶劑混合物包括（但不限 於）石油餾出物，諸如石腦油、重石腦油及石油醚。在— 個實例中，有機溶劑為辛烧。在另一實例中，有機溶劑為 重石腦油，諸如VM&P石腦油。 來自儲存槽58之粗壬二酸可在熱水槽8〇中與水合併，其 中水之溫度係在約175°F(79°C)至約230卞（110。〇之範圍 内，產生濃的粗壬一酸水溶液’接著根據一個實施例將其 161977.doc 12 201245137 饋入萃取器64中且與有機溶劑混合。隨著時間推移，不可 混各之有機/谷劑自水溶液分離，由此形成經萃取之壬二酸 水溶液及含有經萃取副產物酸（BpA)之有機溶劑層。在離 開萃取ϋ 64時，經萃取之壬二酸水溶液之有機溶劑含量應 儘可能低，以避免將易燃有機溶劑引入設備之其他部分， 同，將經萃取水溶液轉移至結晶器85卜可使用閃蒸槽自 經萃取水溶液中移除有機溶劑。根據一個實施例，在任何 後續加工步驟之前，經萃取水溶液包含小於丨重量％之有 機溶劑部分。 若需要，則可將包含有機溶劑及經萃取BpA(例如⑺至 C22單羧酸）之有機相轉移至BpA儲存容器”中。然而，根 據本發明之一個實施例，如下文所說明，可執行進一步加 工以藉由移除BPA使有機溶劑再循環。 在一個實施例中，可將包含(：9至（：22單羧酸之有機溶劑 層轉移至有機溶劑蒸發器90中，在其中藉由汽化有機溶劑 形成有機溶劑蒸氣使有機溶劑自（：9至(：：22單羧酸分離，由 此留下C9至C22單羧酸作為殘餘物。任何合適條件均可用 於有機溶劑蒸料元。舉例而言，有機溶㈣發器可在約 25(TF(12rC)至約275下（135。〇及大氣壓力下運作。若需 要，則可將含有C9至C22單羧酸之殘餘物儲存以用於後續 加工。 將已自C9至C22單叛酸分離之有機溶劑蒸氣運輸至冷凝 器95中，冷凝器使有機溶劑蒸氣冷凝形成再循環有機溶 劑，再循環有機溶劑接著流經傾析器1〇〇以移除夾帶水， 161977.doc •13- 201245137 且可收集於再循環有機溶劑槽105中。根據本發明之一個 實施例，再循環有機溶劑包括小於i重量％之〇9至C22單羧 酸。舉例而言，再循環有機溶劑中之⑺至^以單羧酸之剩 餘含量可小於0.5重量％，或小於〇丨重量％，或小於〇 〇5重 量％。 C9至C22單羧酸殘餘物可藉由使用其他蒸餾單元經進一 步加工以在殘餘物排出之前汽提掉任何剩餘有機溶劑。舉 例而言，可將來自蒸發器90之C9至C22單羧酸殘餘物輸送 至有機溶劑汽提器11〇中。有機溶劑汽提器11〇使用諸如水 蒸/*L之載體蒸氣以汽提出任何剩餘溶劑。任何合適條件均 可用於有機溶劑汽提器110。舉例而言，汽提器u〇可在大 致約250卞（121。〇至約275卞（135。〇及大氣壓力下運作。 回收之有機溶劑可在冷凝器95之前與第一蒸餾有機溶劑合 併’或可使用單機冷凝器。汽提水蒸汽亦在冷凝器95中冷 凝，但接著與溶劑分離。舉例而言，可使用傾析器1 〇〇使 水與有機溶劑分離。 由此提供足夠純之再循環有機溶劑，接著再用於純化壬 二酸至足夠純度’以用於製備可用於許多不同目的（諸如 潤滑劑、增塑劑、漆、除草劑及皮膚治療劑）之衍生物。 舉例而言，可根據本文所述方法實現C9至C22單致酸之剩 餘含量小於0.5重量°/〇之壬二酸。在另一實施例中，可實現 C9至C22單羧酸之剩餘含量小於0.1重量％或0,05重量。/〇之 壬二酸。 本文所述裝置及方法可適用於使自烯系不.飽和單叛酸 161977.doc 14 201245137 (諸如油酸）衍生之二羧酸純化中所用之有機溶劑再循環。 如上文所提及，該等裝置及方法尤其適用於使油酸分解成 壬酸及壬二酸之臭氧分解系統。然而，該等裝置及方法可 適用於純化可經由所述臭氧分解反應自除油酸外之烯系不 飽和單羧酸衍生之其他二羧酸。不飽和酸一般可具有6至 3〇個碳原子，例如8至24個碳原子及一或多個不飽和碳碳 鍵。由臭氧分解反應產生之一元酸及二元酸產物藉由不飽 和酸中一或多個不飽和碳碳鍵之位置來確定。不飽和酸可 自諸如植物、動物或微生物之生物來源分離◊或者，不飽 和酸可自石油來源及合成來源分離。例示性不飽和酸及其 各別可能氧化產物均包括在下表内。 表1 ·例示性烯系不飽和化合物及相應臭氧處理產物 碳 To- 10 11 12 14 16 18 18 18 18 20 22 22 24 26 30 例示性一元產物 —己酸 甲酸 甲酸 丙酸 戊酸 庚酸 月桂酸 壬酸 庚酸 己酸 十一烷酸 十一烷酸 壬酸 壬酸 壬酸 '但應瞭解亦 其街生物可 例示性二元產物 丁二酸 壬二酸 癸二酸 壬二酸 壬二酸 壬二酸 己二酸 壬二酸 十一烷二酸 十二烷二酸 壬二酸 十一烷二酸 十三烷二酸 十五烷二酸 十七烷二酸 .十一烷二酸 可使用聚不飽和 用於許多不同目 例示性不飽和脂肪酸 癸烯酸 癸稀酸(caproleic acid) 十一稀酸 月桂酸 十四稀酸 棕櫊油酸 岩芹酸 油酸 異油酸 十八稀酸 鳕油酸 鯨蠟烯酸 芥子酸 鯊油酸 二十六稀酸 21-三十稀酸 酸 儘管上表包括單不飽和 酸。所得一元酸及二元酸及 161977.doc -15- 201245137 的，諸如潤滑劑、增塑劑、漆、除草劑及皮膚治療劑β 儘管本發明已由其一或多個實施例之描述來說明且儘管 已非常詳細地描述該等實施例，但其不欲將隨附申請專利 範圍之範疇限制或以任何方式限制於該細節。其他優勢及 修改對於熟習此項技術者顯而易見。因此本發明在其廣泛 態樣中不限於具體細節、代表性產物及/或所示及所述方 法及實例。本文所述例示性實施例之各種特徵可以任何組 合形式來使用。因此，在不背離本發明一般概念之範疇的 情況下，可偏離該等細節。 【圖式簡單說明】 圖1為表示油酸臭氧分解設備之示意圖（根據先前技 術）。 圖2為表示根據本發明之一個實施例的有機萃取劑回收 系統之示意圖。 【主要元件符號說明】 10 饋料槽 13 臭氧吸收器 16 氧源 19 脫水器 22 臭氧產生器 25 靜電集塵器 28 壓氣泵 31 冷卻器 34 臭氧產生系統閥門 161977.doc • 16- 201245137 37 臭氧化物分解系統反應器 40 第一蒸餾單元 43 第一冷凝器 46 粗壬酸儲存槽 49 閥門 52 壬二酸蒸餾單元 55 壬二酸德出物冷凝器 58 粗壬二酸儲存槽 61 殘餘物儲存器 64 萃取器 67 副產物酸儲存器 70 蒸發器 73 刨片機 76 壬二酸儲存箱 80 熱水槽 81 傾析器 85 結晶器 90 有機溶劑蒸發器 95 冷凝器 100 傾析器 105 再循環有機溶劑槽 110 有機溶劑汽提器 161977.doc -17-201245137 VI. Description of the Invention: [Technical Field] The present invention relates to a method for purifying a dicarboxylic acid compound obtained by oxidative ozone decomposition of an ethylenically unsaturated compound, and a device for carrying out the method. [Prior Art] Commercial production of azelaic acid and citric acid has been achieved by oxidatively cleavage of a rare (-c=c-) unit in oleic acid. For example, azelaic acid has been prepared by oxidizing oleic acid with chromium sulfate, as disclosed in U.S. Patent No. 2,450,858. However, since stoichiometric use of chromium reagents is undesirable, more efficient methods of utilizing ozone have been developed, such as U.S. Patent No. 2,813,113; No. 5,8,1,275; 5,883,269; and 5,973,173 Revealed and described in the number. The basic method will be best understood by reference to the description in the accompanying drawings, which is a schematic flow chart showing the parts of the apparatus used and their relationship in the ozonolysis process. Referring to Figure 1, oleic acid is supplied to a feed tank 10 and then to an ozone absorber 13 wherein the oleic acid flows countercurrently to a continuous stream of oxygen/ozone gas mixture introduced into the ozone absorber 13. The ozone absorber 13 is cooled or cooled to substantially control the temperature of the reaction occurring therein. Ozone absorber 13 receives ozone treated oxygen by a continuous closed system of circulating oxygen. Because of &, a predetermined portion of the oxygen is used and reused multiple times, and only a small degree of suction and feeding is required to maintain the oxygen content at a predetermined rate: Χ. The circulating oxygen system includes an oxygen source 16 to the dehydrator 19. The oxygen generator 19 is transferred to the ozone generator I. The ozone generator uses current to convert oxygen into ozone. The gaseous mixture of ozone and oxygen is passed to the ozone absorber 13 by ozone 16 1977.doc 201245137. In the ozone absorber, substantially all of the ozone content is absorbed by the oleic acid to form the oleic acid ozonide. The viscosity of the mixture may increase during the residence time of the oleic acid ozonide mixture in the ozone absorber 13. If desired, the viscosity of the mixture can be lowered by introducing a compatible solvent' as discussed further below. Once the ozone absorber 13' is left, the substantially ozone-free gas mixture will flow into the electrostatic precipitator 25, which will remove any fine misty organic matter that can be absorbed in the ozone absorber 13. The purified gas mixture is then passed from the electrostatic precipitator 25 via compressor (4) to the cooler 31 and then back to the dehydrator 19. - substantially all of the moisture in the dehydrator has been removed from the gas mixture. Between the cooler 31 and the dehydrator 19, the oxygen-containing gas obtained or extracted from the line via the ozone generating system valve 34 can be supplied to the ozonide decomposition system reactor 37. The aforementioned absorption of ozone by oleic acid forms oleic acid. The ozonide is transferred to the ozonide decomposition system reactor 37 and treated with oxygen extracted from the ozone generation system valve 34. The ozonide decomposition system reactor can be any type of device suitable for providing substantial interfacial contact between liquid and gas and which can be cooled to adjust the reaction temperature. The oxygen extracted from the ozone generating system is fed to the bottom of the ozonide decomposition system reactor 37, and is agitated with the liquid in each tank by means of a mechanical stirrer (not shown). Although only one overall ozonide decomposition system reactor 37 is shown in the drawings, it should be understood that reactor 37 can include different regions for independent temperature, independent pressure control, or both. Alternatively, any number of reactors may be used depending on the size of the reactor, the flow rate of the ozonide and its decomposition products, and the agitation efficiency of the contact between the oxygen and the treated liquid I61977.doc 201245137. Furthermore, alternative embodiments having more than one reactor may be connected in series, in parallel configuration, or both. The temperature control is an important operational parameter of the ozonide decomposition system reactor 37. More specifically, the ozonide feed stream must be heated to achieve a suitable reaction temperature at which the ozonide portion is effectively oxidatively decomposed upon exposure to one or more catalysts to preferentially form aldehydes and carboxylic acids. The ozonolysis catalyst may include Brünster-Lorry (Brothers-Lowry), Lewis acid, Lewis base, metal or a salt thereof, and a fatty acid salt. The exemplary ozonide decomposition catalyst may at least partially comprise Na, K, B, Sn, Zn, Pt, Pd, Rh 'Ag ' Mn, Cu, Ni, titanium dioxide / ceria or dioxane / P2 〇 5 complex and Its combination. The catalyst can be introduced into the process as a soluble material or as a solid or supported catalyst. Further oxidation of the aldehyde functional group to the carboxylic acid group upon attachment to the hydrazine reaction temperature can occur at a rate sufficient to produce ± calories, which can help increase the temperature of the odorous oxide feed stream. However, it may be necessary to supply cooling water. Y 'Rise rises above the predetermined level. Thus, the temperature is controlled to apply the "force to effect the effective oxidation of the ozonide to the mixed oxidation product. In Fig. 1, the heating and cooling device is not shown. The mixed oxidation product is caused to flow from the ozonide decomposition system reactor to the first two units 40', wherein the first residue of the oxidized product and the other carboxylic acid is converted into the first distillate and the mixed oxidation product. The first product containing citric acid is converted to a liquid in the first condenser 43, and then passed through 161977.doc 201245137 to the crude acid storage tank 46. However, if necessary, in the absorber 13 Some of the crude citric acid is used to dilute the oleic acid reactant and the oleic acid ozonide. Thus, niobic acid, which may be a crude material or which may be further purified, may be added to the ozone absorber 13 to lower the viscosity of the ozonide in the absorber 13. The amount of recycled tantalum supplied to the absorber 13 can be controlled by the door 49. It should be noted that other viscosity reducing agents and diluents can be used. The diluent can be a known substance that is not easily reacted with ozone and is compatible with the ozonide or reaction product. The bite may be part of the reaction product. These diluents include, but are not limited to, saturated short chain acids such as acetic acid, butyric acid, caproic acid, heptanoic acid, caprylic acid, capric acid, and capric acid; and Butyl acrylate; and alkanes such as hexane, octane and decane. However, citric acid is recommended because it is the final product of the process 'it does not interfere with the operation of the circulating oxygen system and does not require separate distillation. In other words, Since citric acid is one of the final products of the process, it is a suitable diluent. Next, a considerable portion of the currently stripped off-co-product of the mixed oxidation product of citric acid is sent to the azelaic acid distillation unit 52, wherein Distilling a portion of the first residue of the oxidation product to form a second distillate, the second distillate comprising a second residue of sebacic acid and a mixed oxidation product. The second distillate is passed through 4 azelaic acid The library discharge condenser 55 is condensed to form crude azelaic acid which is transferred to the crude adipic acid storage tank 58. The second residue or pitch of the mixed oxidation product remaining after distilling off the second distillate (pitch Removed from the sulphuric acid distillation unit 52 and transferred to the residue reservoir 61. Mixed oxygen: the second residue of the hydrazine product may still contain a certain amount of sebacic acid, so it is processed in a step-by-step process if needed A portion of it can be recovered. 161977.doc 201245137 The crude diacid is transferred from the crude diacid storage tank 58 to the extractor 64 where the crude diacid is heated with hot water (eg, about 175 °F (about 80 Å). The by-product acid (ΒΡΑ) from (:) to about 2 HTF (about 99 〇) extracted to form a hot aqueous solution of sebacic acid dissolved in the hot azelaic acid aqueous solution is decanted by the extractor 64 into the helium reservoir 67. At the same time, the hot azelaic acid aqueous solution is transferred to the evaporator 70, and water is removed therein. Next, the azelaic acid in a molten form is fed from the evaporator 70 to the tablet maker 73, wherein the temperature falls below the dissolution rate. Point, and then the solid sheet of sebacic acid is delivered to the sebacic acid storage tank 76. Although the methods and apparatus described above provide the desired product from oleic acid, such as azelaic acid and citric acid, there is still a product Chemical purity, personal safety, system efficiency and equipment life defects. One such defect in prior art procedures and devices is associated with achieving high purity of sebacic acid without sacrificing its overall yield. For example, certain impurities in the crude acid, such as long chain (e.g., C14 to C18) monocarboxylic acids, are difficult to remove by distillation, where the boiling points may be extremely similar. Monocarboxylic acid impurities can be problematic depending on the application of the azelaic acid. For example, a monocarboxylic acid can act as a "chain terminator" during the formation of a long linear polymer (e.g., polyamine) from a dicarboxylic acid. Therefore, there is a need for a novel procedure for purifying a dicarboxylic acid such as sebacic acid. SUMMARY OF THE INVENTION According to an embodiment of the present invention, a method of purifying a dicarboxylic acid is provided. The method comprises ozone treating a mixture comprising an ethylenically unsaturated compound having 6 to 24 carbons and 3 ozone gases to form a plurality of ozone treatment products. The plurality of ozone treatment products are cleaved under oxidizing conditions in the presence of a suitable catalyst to form a mixed oxidation. product. The mixed oxidation products comprise (: 2 to (: 22 single 161977.doc 201245137 carboxylic acid and a mixture of C2 to C22 dicarboxylic acid. The method further comprises distilling and mixing the oxidation product to provide a first distillate and a mixed oxidation product) a first residue. The first distillate comprises a mixture of C2 to (:: "monocarboxylic acids, and the first residue of the mixed oxidation product comprises a mixture of a dicarboxylic acid and (^ to a C22 monocarboxylic acid. The method further Including distilling a first residue of the mixed oxidation product to provide a second residue of the second distillate and the mixed oxidation product, wherein the second distillate comprises a fraction of a mixture of a dicarboxylic acid and a C9 to C22 monocarboxylic acid; The second distillate is partitioned between water and an organic solvent, wherein the temperature of the water is in the range of from about 175 Torr (79 Torr to about 230 Torr (110 Å; wherein the water is substantially immiscible with the organic solvent, Thereby, an organic solvent layer containing an aqueous layer of a dicarboxylic acid and at least a part of a fraction containing a mixture of C9 to C22 monocarboxylic acids is formed, and an organic solvent layer is separated from the aqueous layer. The method further comprises separating the dicarboxylic acid from the aqueous layer. Acid to provide C9 A purified dicarboxylic acid having a residual content of C22 monocarboxylic acid of less than 5% by weight. According to another embodiment of the present invention, there is provided a process for producing a monocarboxylic acid and a dicarboxylic acid from an unsaturated carboxylic acid. The method comprises the steps of: Generating an ozone gas in an ozone generator; contacting the ozone gas with an unsaturated ortho-acid-containing unsaturated acid feedstock in an absorber to obtain an ozonide oxide; contacting the ozonide with oxygen and at least one catalyst in the reactor to provide Mixing the oxidation product, and separating at least a portion of the monocarboxylic acid from the mixed oxidation products by distillation to provide a first distillate and a first residue of the mixed oxidation product, wherein the first distillate comprises a monocarboxylic acid An acid fraction and wherein the first residue of the mixed oxidation products comprises a diaster acid acid. The method advancement comprises extracting pure 161977.doc 201245137 by a method according to the method described herein. Acid. According to another embodiment of the invention, a chemical derivative of a dicarboxylic acid obtained by the process claimed herein is provided. The present invention is described with respect to the embodiments of the present invention, and together with the general description of the invention and the detailed description given below. A method for purifying a dicarboxylic acid compound derived from a chemical method in which an unsaturated carboxylic acid is contacted with ozone to obtain ozonation: an ozonide is treated in the reactor with an oxygen-containing gas and at least an oxidation catalyst to obtain a a mixed oxidation product of a monocarboxylic acid and a dicarboxylic acid. The carboxylic acid mixture is purified by distilling at least a portion of the monocarboxylic acid in the first distillation fraction, thereby leaving dicarboxyl 2 in the first residue of the mixed oxidation product. The residue of the mixed oxidation product is then distilled by a second distillation to form a second distillate and a second residue of the mixed oxidation product. The second distillate: comprises a dicarboxylic acid and the monocarboxylic acid impurity may be present in an amount between about 10% by weight and about 30% by weight, wherein a substantial portion of such impurities cannot be effectively removed by fractionation. Thus the additional purification of the 'saturated diacid is affected by the inclusion extraction. The second residue of the mixed oxidation product is immersed in various tars and metal fatty acid solutions from at least one oxidation catalyst. Suitable: The unsaturated compound performs ozone fractionation Any amount: and the compound is especially not limited by its source and may include % atoms, such as 6 to 24 carbon atoms. For example, the dilute 161977.doc 201245137 unsaturated compound may include an ethylenically unsaturated beta having 12 to 20 carbon atoms. Thus, the ethylenically unsaturated compound can have 8 carbon atoms. Further, the ethylenically unsaturated compound may include other functional groups such as a carboxylic acid. The ethylenically unsaturated compound can be derived from an animal or plant source. Thus, ethylenically unsaturated compounds include fatty acids, including those derived from palm oil or tallow. In one example, the (iv) unsaturated compound includes oleic acid. After reacting the C6 to C24 ethylenically unsaturated compound with the ozone-containing gas, a plurality of ozone treatment products are formed which are cleaved under oxidizing conditions in the presence of a suitable catalyst to form a mixed oxidation product comprising a ruthenium to C22 monocarboxylic acid and (: a mixture of 2 to 022 dicarboxylic acids. For example, a mixture of carboxylic acids may include C2 to C16, C5 to C9 or (:6 to (:18) monocarboxylic acid. For example, a mixture of 'carboxylic acids may include C2 to C16, C5 to (7) or even C18 dicarboxylic acid. According to an exemplary embodiment, ozonolysis can be performed on oleic acid, thereby producing decanoic acid (which is a saturated C9 monocarboxylic acid) and sebacic acid (which is Saturated C9 dicarboxylic acid). To separate the desired dicarboxylic acid such as sebacic acid, the mixed oxidation product derivatized from oleic acid is distilled under a first set of distillation conditions to provide a portion of the rhodium to C22 monocarboxylic acid (which may include a first distillate of citric acid) and a first residue of a mixed oxidation product. The first residue of the oxidation product comprises a desired diacid (eg, azelaic acid) and a plurality of impurity acids, which may include (:9 To (:22 a mixture of monocarboxylic acids And a second diesterified acid. The first residue of the mixed oxidation product is then subjected to a second distillation under a second set of distillation conditions to provide a second distillate and a second residue of the mixed oxidation product. The first fraction containing the desired dicarboxylic acid and a plurality of impurity acids 161977.doc •10· 201245137 The impurity acid is a by-product acid (Βρα), which may include a C9 to 〇22 monocarboxylic acid thirst compound. Separation of azelaic acid from a large number of impurity acids, further processing including aqueous extraction using an organic solvent, as described in τ. Water extraction involves disposing the second substance in water and/or water and being substantially immiscible with water. Between the organics, therefore, the second distillate is combined with hot water to form a concentrated aqueous solution of the sage. If necessary, the part of the product may not be dissolved in the concentrated solution. ) decanting from a concentrated aqueous solution in a separate extractor or in an analysis, followed by extracting the concentrated aqueous solution by an organic solvent or simply transferring it to the extractor in the presence of β, then enriching the aqueous distillate with organic Solvent mixing, where The second acid of the diacid together with a plurality of impurities θλ (such as various water-soluble short chains (for example, 匸4 to c8) di-retensive acid) retains m, that is, a water phase towel. The organic solvent soluble by-product acid (for example, C9 to The C22 monocarboxylic acid) is extracted into an organic solvent. Referring to Figure 2, the crude sebacic acid from the storage tank 58 ((4) the second pavilion) can be combined with water in the hot water tank 80 to produce a concentrated aqueous solution of crude azelaic acid. Next: it is fed into a decanter 81, in which a by-product acid which is insoluble in the aqueous solution of the hot azelaic acid can be decanted from the concentrated aqueous solution, and then transferred to the extractor 64, which then The concentrated aqueous solution is mixed with an organic solvent. According to one embodiment, the concentrated aqueous crude azelaic acid solution can be fed directly into the extractor 64. According to one embodiment, the sebacic acid extractor 64 can be York-Shaibel Extractor (Y〇rk_Seheibel extract〇〇, which is a countercurrent, multistage, continuous liquid/liquid extractor. In an embodiment towel, the York_Shaybel extractor has a rating of from about 1 to about 6 inches. For example, York I61977.doc 201245137 50 or 60 or 60 Schebel extractors can have ratings of 10, 20, 3, and 4 (). π - defeat. Luo is in hot water. The water extraction temperature can range from about 175 FWC) to about 2 (1) generations. Extraction can be carried out under ambient pressure or under high pressure conditions. The organic solvent is not particularly limited to any particular solvent' but should be substantially immiscible with water under operating conditions. For example, 'at 20. (The water solubility of the lower organic solvent may be less than 〇5 core. Further, at the extraction pressure, the boiling point of the suitable organic solvent is greater than the temperature of the extraction water. Exemplary organic solvents that can be used in the process include, but are not limited to, crude dicarboxyl The presence of an acid in the acid is soluble in a solvent in which the dibasic acid is substantially insoluble in the aliphatic or aromatic hydrocarbon solvent and/or a mixture thereof. Examples of such aliphatic solvents include, but are not limited to, a linear chain. And branched, cyclic and non-cyclic alkanes such as pentane, hexane, heptane, octane, 2,2,4·trimethylpentane, cyclopentane, cyclohexane, nonylcyclopentane , methylcyclohexane; olefins such as pentene, hexene, heptene, cyclopentene, cyclohexene, methylcyclopentene, methylcyclohexene and the like; and at room temperature and chamber pressure Lower liquefied hydrocarbons, such as liquid propane and liquid butane, such as liquid propane and liquid butane. Examples of such aromatic solvents include, but are not limited to, benzene, toluene, and xylene. Solvent mixtures include, but are not limited to, petroleum distillates, Such as naphtha, heavy naphtha and petroleum ether. In one example, the organic solvent is octyl. In another example, the organic solvent is heavy naphtha, such as VM&P naphtha. The crude azelaic acid from storage tank 58 can be combined with water in a hot water tank 8 , where the temperature of the water is about 175 °F. From (79 ° C) to about 230 Torr (110. Torr, a concentrated aqueous solution of crude sulphuric acid is produced.) Then, according to one embodiment, 161977.doc 12 201245137 is fed into the extractor 64 and mixed with an organic solvent. Over time, the non-mixable organic/treat agent is separated from the aqueous solution, thereby forming an aqueous solution of the extracted sebacic acid and an organic solvent layer containing the extracted by-product acid (BpA). The organic solvent content of the extracted aqueous azelaic acid solution should be as low as possible to avoid introducing the flammable organic solvent into other parts of the apparatus. Similarly, the extracted aqueous solution can be transferred to the crystallizer 85. The flash tank can be used to extract the aqueous solution from the aqueous solution. The organic solvent is removed. According to one embodiment, the extracted aqueous solution contains less than 5% by weight of the organic solvent portion prior to any subsequent processing steps. If desired, the organic solvent and the extracted BpA can be included (for example) The organic phase of (7) to C22 monocarboxylic acid) is transferred to a BpA storage vessel. However, according to one embodiment of the invention, further processing may be performed to recycle the organic solvent by removing BPA, as explained below. In one embodiment, an organic solvent layer comprising (9: to 22:monocarboxylic acid) may be transferred to an organic solvent evaporator 90, wherein an organic solvent vapor is formed by vaporizing an organic solvent to cause an organic solvent from (:9 to (:: 22 monocarboxylic acid is separated, thereby leaving a C9 to C22 monocarboxylic acid as a residue. Any suitable conditions can be used for the organic solvent vapor. For example, the organic solvent can be at about 25 (TF) (12rC) to about 275 (135. 〇 and atmospheric pressure. If necessary, the residue containing C9 to C22 monocarboxylic acid can be stored for subsequent processing. The organic solvent vapor that has been separated from C9 to C22 monoterpic acid is transported to a condenser 95 which condenses the organic solvent vapor to form a recycled organic solvent, which is then passed through a decanter 1 to remove Entrained water, 161977.doc • 13- 201245137 and can be collected in the recycled organic solvent tank 105. According to one embodiment of the invention, the recycled organic solvent comprises less than i% by weight of ruthenium 9 to C22 monocarboxylic acid. For example, the residual content of (7) to monocarboxylic acid in the recycled organic solvent may be less than 0.5% by weight, or less than 〇丨% by weight, or less than 5% by weight. The C9 to C22 monocarboxylic acid residue can be further processed by using other distillation units to strip off any remaining organic solvent before the residue is discharged. For example, the C9 to C22 monocarboxylic acid residue from evaporator 90 can be passed to an organic solvent stripper 11〇. The organic solvent stripper 11 uses a carrier vapor such as steam/*L to strip any remaining solvent. Any suitable conditions can be applied to the organic solvent stripper 110. For example, the stripper u can operate at approximately 250 Torr (121 Torr to approximately 275 Torr (135 Torr and atmospheric pressure. The recovered organic solvent can be combined with the first distilled organic solvent prior to condenser 95). 'Alternatively, a single condenser can be used. The stripped water vapor is also condensed in the condenser 95, but then separated from the solvent. For example, the decanter 1 can be used to separate the water from the organic solvent. The organic solvent is recycled, which is then used to purify sebacic acid to a sufficient purity for the preparation of derivatives that can be used for many different purposes, such as lubricants, plasticizers, lacquers, herbicides, and skin therapeutics. In contrast, azelaic acid having a residual content of C9 to C22 monoacids of less than 0.5 wt/min can be achieved according to the methods described herein. In another embodiment, a residual content of C9 to C22 monocarboxylic acids can be achieved less than 0.1. % by weight or 0,05 wt. / 〇 壬 adipic acid. The apparatus and method described herein can be applied to purify a dicarboxylic acid derived from an olefinic monounsaturated 161977.doc 14 201245137 (such as oleic acid). The organic solvent used in the process As mentioned above, the apparatus and method are particularly suitable for the decomposition of oleic acid into an ozonolysis system of citric acid and sebacic acid. However, such apparatus and methods are suitable for purification via the ozonolysis reaction. Other dicarboxylic acids derived from ethylenically unsaturated monocarboxylic acids other than oleic acid. The unsaturated acids may generally have from 6 to 3 carbon atoms, for example from 8 to 24 carbon atoms and one or more unsaturated carbon-carbon bonds. The monobasic acid and the dibasic acid product produced by the ozonolysis reaction are determined by the position of one or more unsaturated carbon-carbon bonds in the unsaturated acid. The unsaturated acid can be separated from a biological source such as a plant, animal or microorganism. Alternatively, the unsaturated acid can be isolated from petroleum sources and synthetic sources. Exemplary unsaturated acids and their respective possible oxidation products are included in the following table. Table 1 - Exemplary ethylenically unsaturated compounds and corresponding ozone treatment product carbon To- 10 11 12 14 16 18 18 18 18 20 22 22 24 26 30 Exemplary unary product - hexanoic acid formic acid propionic acid valeric acid heptanoic acid lauric acid decanoic acid heptanoic acid undecanoic acid undecanoic acid citric acid citric acid Tannic acid 'But it should be understood that its street bio-expressible binary product succinic acid azelaic acid azelaic acid azelaic acid azelaic acid adipic acid adipic acid adipic acid undecanedioic acid dodecanedioate Acid undecanedioic acid tridecanedioic acid pentadecanedioic acid heptadedioic acid. Undecanedioic acid can be used for polyunsaturated unsaturated fatty acid decenoic acid dilute acid (caproleic) Acid) eleven acid lauric acid tetradecanoic acid palm oleic acid rock celery acid oleic acid oleic acid octanoic acid oleic acid cetyl sulphate sorrel acid sulphuric acid twenty-six acid 21-thirty Acidic acid Although the above table includes monounsaturated acids. The resulting monobasic acid and dibasic acid and 161977.doc -15-201245137, such as lubricants, plasticizers, lacquers, herbicides, and skin therapeutic agents, although the invention has been described by one or more embodiments thereof And </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; Other advantages and modifications will be apparent to those skilled in the art. Therefore, the invention in its broader aspects is not limited to the specific details The various features of the illustrative embodiments described herein can be used in any combination. Therefore, departures may be made from such details without departing from the scope of the invention. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic view showing an oleic acid ozonolysis apparatus (according to the prior art). Figure 2 is a schematic diagram showing an organic extractant recovery system in accordance with one embodiment of the present invention. [Main component symbol description] 10 Feed chute 13 Ozone absorber 16 Oxygen source 19 Dehydrator 22 Ozone generator 25 Electrostatic dust collector 28 Compressed air pump 31 Cooler 34 Ozone generating system valve 161977.doc • 16- 201245137 37 Ozone oxide Decomposition system reactor 40 First distillation unit 43 First condenser 46 Crude acid storage tank 49 Valve 52 Sebacic acid distillation unit 55 Sebacic acid decanter condenser 58 Crude diacid storage tank 61 Residue storage 64 Extractor 67 By-product acid reservoir 70 Evaporator 73 Flaker 76 Sebacic acid storage tank 80 Hot water tank 81 Decanter 85 Crystallizer 90 Organic solvent evaporator 95 Condenser 100 Decanter 105 Recirculating organic solvent tank 110 Organic solvent stripper 161977.doc -17-