TWI723216B - 脂肪酸乙酯之製備方法 - Google Patents
脂肪酸乙酯之製備方法 Download PDFInfo
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- TWI723216B TWI723216B TW106130457A TW106130457A TWI723216B TW I723216 B TWI723216 B TW I723216B TW 106130457 A TW106130457 A TW 106130457A TW 106130457 A TW106130457 A TW 106130457A TW I723216 B TWI723216 B TW I723216B
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- fatty acid
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/649—Biodiesel, i.e. fatty acid alkyl esters
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
- A23L29/04—Fatty acids or derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
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Abstract
本揭露係關於一種製備脂肪酸乙酯之方法,係包含:製備一種植物性脂質;藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶以進行轉酯反應;移除存在於該反應器中之三酸甘油酯及雙甘油酯;以及,經由精餾自該反應器中分離出第二脂肪酸乙酯。
Description
本揭露係關於一種製備脂肪酸乙酯之方法,係包括:製備一種植物性脂質;藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶以進行轉酯反應;移除存在於該反應器中之三酸甘油酯及雙甘油酯;以及,經由精餾自該反應器中分離出第二脂肪酸乙酯。
脂肪酸酯類係脂肪酸藉由酯鍵與醇鍵結之形式。結合至該等脂肪酸之醇的類型主要為甲醇、乙醇、丙醇、丁醇等,因此,可自其製備脂肪酸甲酯、脂肪酸乙酯、脂肪酸丙酯、脂肪酸丁酯等。
脂肪酸酯類用途廣泛,但脂肪酸酯類最有用之領域係生物柴油領域。相較於碳氫化合物燃燒時所排放之廢氣造成環境問題,且係全球變暖之主要肇因,生物柴油作為經濟且環境友好之替代燃料,可解決此等環境問題而引起注意。植物性脂質具有作為燃料所需之高熱值,但他們的缺點為高分子材料所具有之高黏度。為了解決該問題,以藉由與醇類之轉酯反應而轉化為具有小分子結構之 脂肪酸烷基酯類作為生物柴油使用。其中,由於價格低廉,主要使用脂肪酸甲酯及脂肪酸乙酯。
用於脂肪酸酯類之醇類中,以甲醇及乙醇具有經濟上的優勢。甲醇主要自石油獲得,而乙醇主要自穀物、甘蔗等獲取且比甲醇更為環境友好。此外,甲醇已知對人體有害且致盲及嚴重之嘔吐。惟,乙醇已知於體內代謝並轉化為乙酸,其對人體之毒性小於甲醇。
據此,於安全性占重要地位之工業,如食品及化妝品領域中,脂肪酸乙酯為較佳者。目前,多種脂肪酸乙酯,如癸酸乙酯(decanoic ethyl ester、ethyl decanoate、ethyl caprate等)、辛酸乙酯(octanoic ethyl ester、ethyl octanoate、ethyl caprylate等)、棕櫚酸乙酯(palmitic ethyl ester、ethyl palmitate、ethyl hexadecanoate等)、硬脂酸乙酯(stearic ethyl ester、ethyl stearate、ethyl octadecanoate等)等係作為調味劑用於食品中。此外,藉由酯的酶促交換反應修飾脂肪酸成分,以作為修飾食用脂肪之方法時,脂肪酸乙酯可作為脂肪酸之原料。此外,各種不同組成之脂肪酸乙酯係作為調味劑、毛髮調理劑、皮膚調理劑(軟化劑)等用於化妝品中。
傳統上,脂肪酸乙酯係使用動物/植物性脂質如棕櫚油、大豆油、菜籽油、魚油、椰子油等,與源自動物/植物性脂質之游離脂肪酸,藉由醇及催化劑於高溫(70℃至90℃)之轉酯反應而製備,且可藉由分離甘油、未反應之脂肪酸、未反應之醇等製程獲得。
近來,對於化學合成方法相關之環境問題的負面觀點散播開來,已開發使用酶生產脂肪酸乙酯之方法。Nelson等人使用在多種微生物中,如米黑毛霉(Mucor miehei)、南極假絲酵母(C.antartica)、洋蔥假單胞菌(Pseudomonas cepacia)、戴氏根霉(Rhizopus delemar)、白地霉(Geotrichum candium)等表現之脂酶,從植物性脂質及醇製備脂肪酸乙酯及脂肪酸甲酯(J Am Oil Chem Soc,73(8):1191-1195,1996)。此外,第10-1357298號韓國專利揭露一種於製備ω-3多不飽和脂肪酸之過程中,在酶催化劑之存在下使用乙醇,藉由乙醇解製備脂肪酸乙酯的方法,該酶係從選自由假絲酵母屬(Candida)、根霉屬(Rhizopus)、毛霉屬(Mucor)、曲霉屬(Aspergillus)、及假單胞菌屬(Pseudomonas)所組成之群組之至少一種微生物中提取萃取。
惟,上揭方法使用如乙醇之有機溶劑,當酶促反應使用有機溶劑如乙醇時,需要額外移除殘留乙醇之步驟,且可能存在安全性問題,因為乙醇之燃點係16℃,故該製程過程中可能起火。此外,該方法具有乙醇可能殘留於最終產物中之缺點,因此,尤其在化妝品領域中,可能出現對皮膚之刺激性的問題。上揭之先前技術聚焦於使用脂肪酸、動物/植物性脂質、及低級醇與化學或酶催化劑製備脂肪酸乙酯,對於不使用乙醇之酶促方法製備脂肪酸乙酯並無積極討論。此外,從油脂製備脂肪酸乙酯後,僅分離出高純度之特定脂肪酸乙酯非常重要。惟,關於其以 高純度分離之技術,尚無詳細之說明。
就此而言,本申請人經眾多嘗試,研發可用於食品及化妝品之脂肪酸乙酯,同時藉由植物性脂質中含有之特定脂肪酸的酶促轉酯反應製備脂肪酸乙酯,而不使用有機溶劑如乙醇,從而完成本揭露。
本揭露之一目的係提供一種製備脂肪酸乙酯之方法,包括:製備一種植物性脂質;藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶以進行轉酯反應;移除存在於該反應器中之三酸甘油酯及雙甘油酯;以及,經由精餾自該反應器分離出第二脂肪酸乙酯。
本揭露之另一目的係提供含有藉由上揭方法製備之脂肪酸乙酯的食品組成物。
本揭露之再一目的係提供含有藉由上揭方法製備之脂肪酸乙酯的化妝品組成物。
為了達成上揭目的,於本揭露之一態樣中,係提供一種製備脂肪酸乙酯之方法,包括:製備植物性脂質;藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶以進行轉酯反應;移除存在於該反應器中之三酸甘油酯及雙甘油酯;以及,經由精餾自該反應器分離出第二脂肪酸乙酯。
於本揭露之另一態樣中,係提供含有藉由上 揭方法製備之脂肪酸乙酯的食品組成物。
於本揭露之又一態樣中,係提供含有藉由上揭方法製備之脂肪酸乙酯的化妝品組成物。
後文中將詳細揭示本揭露。
根據一態樣,係提供一種製備脂肪酸乙酯之方法,其包括:(a)製備一種植物性脂質;(b)藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶以進行轉酯反應;(c)移除存在於該反應器中之三酸甘油酯及雙甘油酯;以及(d)經由精餾自該反應器分離出第二脂肪酸乙酯。
該植物性脂質可含有該植物性脂質本身或其餾分。可用於本揭露中之植物性脂質的非限制性實例可包括菜籽油、椰子油、棕櫚仁油、棕櫚油、菜籽油、葵花油、大豆油、棉籽油、米糠油、玉米油、橄欖油、乳木果脂、芒果仁油、依利伯脂(illippe butter)(婆羅洲脂(Borneo tallow)、狹翅娑羅樹(Shorea stenoptera)或豬油果(Pentadesma butyracea))、娑羅樹油(娑羅樹(Shorea robusta))、或燭果油(kokum oil)(印度藤黃(Garcinia indica)),但該植物性脂質並不限於此,且可包括該技藝中使用之任意植物性脂質。較佳地,該植物性脂質可以是棕櫚仁油、棕櫚油、或葵花油,但並不限於此。
或者,該植物性脂質可經分餾為含有1,3-二 棕櫚醯基-2-油醯基甘油(POP)之脂質餾分,該餾分可用作該植物性脂質。該分餾可透過乾餾或溶劑分餾實施,但並不限於此,且可使用該技藝中已知的方法而無限制,自原料提供具有不同含量之飽和及不飽和脂肪酸之含有POP的油脂作為植物性脂質。舉例而言,可依據該植物性脂質原料之特徵而選擇性地使用分餾方法。於溶劑分餾之情形中,可使用能溶解植物性脂質原料的有機溶劑,如己烷、丙酮甲乙酮、乙醇等而無限制。可用於本發明之植物性脂質可以是含有35wt%(重量%)至70wt%之1,3-二棕櫚醯基-2-油醯基甘油(POP)且碘值為35至55的油。
根據一態樣,該製備脂肪酸乙酯之方法係包括(b)藉由在反應器中混合該植物性脂質、第一脂肪酸乙酯、及脂酶以進行轉酯反應。步驟(b)中施行之轉酯反應可藉由下述反應式表示。
可用於該酶促轉酯反應之脂酶可以是源自米黑毛霉(Mucor miehei)或疏棉狀嗜熱絲孢菌(Thermomyces lanuginosus)之脂酶,但其來源並不限於此,且可使用該技藝中已知之任意脂酶。如上述反應式中所示,用於本發明中之脂酶係用作製備第二脂肪酸乙酯之催化劑的材料,其中,R1係藉由該植物性脂質中的三酸甘油酯之取代基R1與該第一脂肪酸乙酯中的取代基R2互換而被替代。更詳而言,該脂酶可以是對於sn-1,3位置具有特異性者或不具有特異性者。使用酶之反應可於30℃至60℃施行1小時至30小時,但反應條件並不限於此。
根據一態樣,該第一脂肪酸乙酯可以是選自由硬脂酸乙酯、油酸乙酯、亞油酸乙酯、棕櫚酸乙酯、辛酸乙酯、及癸酸乙酯所組成群組之至少一種脂肪酸乙酯。
同時,根據一態樣,步驟(b)中該植物性脂質與該第一脂肪酸乙酯之間的莫耳比可以是2:1至1:5。
同時,根據一態樣,該第二脂肪酸乙酯可以是選自由硬脂酸乙酯、油酸乙酯、及棕櫚酸乙酯所組成群組之至少一種脂肪酸乙酯。
根據一態樣,該製備脂肪酸乙酯之方法係包括(c)移除存在於該反應器中之三酸甘油酯及雙甘油酯。
藉由步驟(b)中之轉酯反應獲得的反應物除了含有脂肪酸乙酯外,亦可含有三酸甘油酯及雙甘油酯。據此,必需移除此等三酸甘油酯及雙甘油酯,以獲得高純度之脂肪酸乙酯。舉例而言,可藉由施行簡單蒸餾、或於塔板數為5或更少之蒸餾塔中於100℃至250℃及1mbar至3mbar之真空度的條件下蒸餾以移除此等三酸甘油酯及雙甘油酯,進而獲得脂肪酸乙酯。自脂肪酸乙酯移除的
三酸甘油酯及雙甘油酯可進一步利用作為加工油,具有在經濟方面的優勢。
步驟(c)可藉由簡單蒸餾或於塔板數為5或更少之蒸餾塔中於220℃至245℃、1mbar至3mbar之真空度、及1至3之回流比的條件下施行。可於上揭範圍內調節該真空度、回流比及溫度,且該等之一的值一旦經調節,則其他值亦可調節。
本發明之方法係包括(d)經由精餾自該反應器分離出第二脂肪酸乙酯。藉由於步驟(c)中移除三酸甘油酯及雙甘油酯,該脂肪酸乙酯之含量比可得以增加。惟,透過步驟(c)獲得之產物中,依據原料中含有之多種脂肪酸之種類而混合多種脂肪酸乙酯。據此,需要選擇性地精餾出待分離之脂肪酸乙酯並以高純度純化之。該精餾係指一種方法,其係透過重複之回流精確地分離出具有相似沸點的揮發性物質。更詳而言,由於使用平衡蒸餾來分離具有相似揮發度之組分導致冷凝之蒸汽及剩餘液體的純度極差,所生成之蒸汽被帶至與返回至蒸餾器之冷凝物的一部分以及逆流物接觸,而具有低沸點之組分藉由該蒸汽之凝結熱再次蒸發。藉由重複此製程而更精確地分離並濃縮材料之製程稱為精餾,且該簡單蒸餾可經串聯,當蒸汽流與回流接觸時,該蒸汽可經濃縮。舉例而言,經步驟(c)之產物可於具有15至30塔板數之蒸餾塔中於1mbar至3mbar之真空度、100℃至250℃之溫度、及1至5之回流比的條件下精餾,從而僅分離出所欲之脂肪酸乙酯。惟,
精餾之詳細條件並不限於上揭者,且可根據待分離之脂肪酸乙酯的種類,控制更詳細的真空度、溫度、回流比等。透過該精餾製程,可獲得的該脂肪酸乙酯之純度為92%至100%;詳而言,純度為95%或更高;且更詳而言,純度為98%或更高。
步驟(d)可藉由簡單蒸餾或在塔板數為15或更低之蒸餾塔中於205℃至240℃、1mbar至3mbar之真空度、及1至3之回流比的條件下施行。該真空度、回流比及溫度可在上揭範圍內調節,且該等之一的值一旦被調節,則其他值亦可調節。
該製備脂肪酸乙酯之方法係藉由使用酶之酯交換反應完成,且該方法之特徵為該方法並不包括加入有機溶劑。使用化學催化劑之傳統反應中,普遍使用有機溶劑。惟,由於用作溶劑之材料不能從作為後續產品之脂肪酸乙酯完全移除,當該產品作為食品組成物或化妝品組成物而用於人體時,可能產生刺激或有害。因此,本揭露之製備方法不使用有機溶劑等可能對人體有害者,因此,藉此製備之材料在用於食品組成物或化妝品組成物時具有優勢。
此外,根據一態樣,可提供藉由上揭方法製備之含有脂肪酸乙酯的食品組成物。脂肪酸乙酯可用於食品組成物中,用於提升膳食質地之目的,或作為添加劑如調味劑等而使用。
含有脂肪酸乙酯之食品的實例可包括肉類、香腸、麵包、巧克力、糖果、零食、餅乾、披薩、拉麵、其他麵條、口香糖、包括冰淇淋在內之乳製品、各種湯類、飲料、茶、飲品、酒精飲料、維生素複合物等,且可包括傳統觀點之所有種類的食品。
此外,該食品可藉由加入已知在活體內發揮生物調節功能如生物防禦、生物節律之調節、疾病之預防及恢復等的活性成分,而製備為用於健康補充目的之健康功能性食品。
此外,於例示性態樣中,本揭露係提供含有藉由上揭之方法製備之脂肪酸乙酯的化妝品組成物。
該化妝品組成物可製備為選自由溶液、外用軟膏、乳霜、泡沫、滋養潤膚劑、軟潤膚劑、剝撕式面膜、柔膚水、乳液、化妝底霜、精華、潤唇膏、皂、液體清潔劑、浴用製品、防曬霜、防曬油、懸浮液、糊劑、凝膠、洗劑、粉體、含有界面活性劑之清潔劑、油、粉狀粉底、乳液粉底、蠟狀粉底、貼劑、及噴霧劑所組成群組之製劑,但該製劑並不限於此。詳而言,於該化妝品組成物中,藉由上揭方法製備之脂肪酸乙酯可用作添加劑(如,增溶劑、乳化劑、分散劑、芳香劑、軟化劑等)來改善或安定其他活性成分之溶解性。
此外,本發明之化妝品組成物可復包含至少一種用於皮膚之一般化妝品組成物中待混入的化妝上可接受之載劑,舉例而言,常用之成分如脂肪成分、水、界面活性劑、保濕劑、低級醇、增稠劑、螯合劑、顏料、防腐 劑、芳香劑等可適宜地混入其中,但該等額外之成分並不限於此。
或者,本發明之化妝品組成物可藉由復包含具有抗氧化效果、改善皺紋效果、抗老化效果、及/或阻擋紫外線效果之組分而製備為功能性化妝品。對於該具有抗氧化效果、改善皺紋效果、抗老化效果、及/或阻擋紫外線效果之成分,可使用該技藝中已知用於功能性化妝品之任意活性成分而無限制。
本揭露係提供一種藉由酶促轉酯反應製備脂肪酸乙酯而不使用有機溶劑或化學催化劑的方法。如此製備之脂肪酸乙酯可排除其可能含有對人體有害或造成刺激之化學殘留的可能性。據此,如此製備之脂肪酸乙酯可用於食品組成物或化妝品組成物中。
本揭露之製備脂肪酸乙酯的方法可排除對人體有害或可造成刺激之化學品的使用。據此,如此製備之脂肪酸乙酯可廣泛用於食品組成物或化妝品組成物中。
後文中,將透過具體實施例詳細揭露本發明。惟,本文中提議之說明係僅用於例示性說明目的之較佳實例,而非意圖限制本揭露之範疇,因此,應理解該等實施例係提供一般熟知該技藝者更佳說明。
實施例1:藉由酶促轉酯反應製備脂肪酸乙酯
本實施例中,藉由下揭之方法製備棕櫚酸乙酯。對於用作原料之植物性脂質,係選擇含有高棕櫚酸含量的源自棕櫚油之脂肪餾分。特別地,該源自棕櫚油之脂肪餾分的POP含量為35%至70%,且碘值為35至55。對於用於與該脂肪酸交換且與該源自棕櫚油之脂肪餾分一起供給乙基的脂肪酸乙酯,係使用硬脂酸乙酯。
詳而言,將源自棕櫚油之脂肪餾分與硬脂酸乙酯以1:0.5至1:5之莫耳比混合。將該混合物與5wt%之源自米黑毛霉(Mucor miehei)之脂酶混合,並於配備攪拌器之反應器內施行轉酯反應(攪拌轉酯反應)。同時,除上揭者外,將酶填入雙層夾套之玻璃管柱內,在該原料混合物穿過該管柱之同時施行轉酯反應(連續轉酯反應)。特別地,反應溫度保持恆定於50℃。收集隨著反應時間而產生之棕櫚酸乙酯。
實施例2:三酸甘油酯之分離
施行蒸餾,以從硬脂酸乙酯及實施例1中藉由轉酯反應獲得之棕櫚酸乙酯中分離三酸甘油酯。
於4段蒸餾塔中於下述條件施行蒸餾:真空度為2mbar、塔底部溫度為220℃至245℃、且回流比為1,以移除三酸甘油酯,從而獲得硬脂酸乙酯及棕櫚酸乙酯(亦即,脂肪酸乙酯)。
實施例3:脂肪酸乙酯之組成及含量分析
3.1. GC-FID分析
藉由氣相層析(GC)分析從實施例2獲得之脂肪酸乙酯的組成及含量。具體之分析條件示於下表2中。分析前,脂肪酸乙酯可藉由傳統方法甲基化而用於脂肪酸之分析,並將50μL所得之脂肪酸乙酯溶解於1mL己烷中備用。本實施例中,係省略甲基化程序施行該分析。
3.2. 脂肪酸乙酯之組成的分析
分析根據實施例2之蒸餾製程獲得之脂肪酸乙酯的組成及含量。經GC-FID證實之該脂肪酸乙酯的組成示於下表3中。
如上表3中所示,相同反應時間下,隨著硬脂酸乙酯與源自棕櫚油之脂肪餾分莫耳比增加,棕櫚酸乙酯之量增加。惟,即使硬脂酸乙酯與源自棕櫚油之脂肪餾分之莫耳比從1:2增加至1:5,棕櫚酸乙酯之量並無顯著差異。據此,從製程效率之觀點看來,最適宜之比係1:2,其棕櫚酸乙酯含量係43.5%。
實施例4:棕櫚酸乙酯之純度的改善
施行精餾,以改善從實施例2獲得之脂肪酸乙酯混合物中分離硬脂酸乙酯(原料)而得之棕櫚酸乙酯(產物)的純度。詳而言,蒸餾係於22段蒸餾塔中於下述條件下施行:真空度為2mbar,塔底部溫度為235℃,且回流比為3,從而獲得高純度之棕櫚酸乙酯。
實施例5:經純化之棕櫚酸乙酯的純度分析
分析根據實施例4之精餾而獲得之棕櫚酸乙酯的純度。該分析係使用如實施例3中之GC-FID施行,結果示於下表4中。
如上表4所示,證實藉由額外之蒸餾製程,棕櫚酸乙酯純度增加至98.6%。蒸餾後,於蒸餾塔底部產生之硬脂酸乙酯的純度可為98%或更高,因此,該硬脂酸乙酯可再次作為脂肪酸乙酯之原材料用於實施例1之酶促反應中。
實施例6:脂肪酸乙酯之種類之多樣性的評估
除了根據實施例1中使用棕櫚中間餾分(PMF)脂肪作為植物性脂質製備棕櫚酸乙酯外,基於多種脂肪酸組成物可包含於各種植物性脂質中之事實,藉由類似於實施例1之酶促轉酯反應,使用高油酸之葵花油、菜籽油、及椰子油作為原料替代棕櫚中間餾分(PMF)脂肪製備脂肪酸乙酯。將三種植物性脂質及硬脂酸乙酯以1:2之莫耳比混合,將5wt%源自米黑毛霉(Mucor miehei)之脂酶加至其中,在配備攪拌器之反應器中反應12小時。反應溫度係保持在45℃。
藉由與實施例2中用以移除三酸甘油酯相同之方法將三酸甘油酯自酯化反應獲得之混合物中移除,並分離出脂肪酸乙酯。使用與實施例3類似之方法(GC-FID)分析經分離之脂肪酸乙酯的組成及含量,結果示於下表5中。
如上表5所示,油酸乙酯係從高油酸之葵花油製備;油酸乙酯及亞麻酸乙酯係從菜籽油製備;而辛酸乙酯及癸酸乙酯係從椰子油製備。如此獲得之脂肪酸乙酯的純度可藉由使用與實施例4類似之蒸餾塔精餾而得以改善。
Claims (5)
- 一種製備脂肪酸乙酯之方法,包含:(a)製備植物性脂質;(b)藉由於反應器中混合該植物性脂質、第一脂肪酸乙酯及脂酶,以進行轉酯反應,其中,於步驟(b)中,該植物性脂質與該第一脂肪酸乙酯之莫耳比係1:2至1:4,其中,該植物性脂質係棕櫚油,以及,該植物性脂質係包含35wt%至70wt%之1,3-二棕櫚醯基-2-油醯基甘油(POP),且其碘值為35至55;(c)移除存在於該反應器中之三酸甘油酯及雙甘油酯:以及(d)經由精餾自該反應器中分離出第二脂肪酸乙酯,其中,該自步驟(d)中分離之第二脂肪酸乙酯係棕櫚酸乙酯,且純度為92%至100%。
- 如申請專利範圍第1項所述之方法,其中,步驟(c)係於蒸餾塔中於下述條件下施行:220℃至245℃;真空度為1mbar至3mbar;以及,回流比為1至3。
- 如申請專利範圍第1項所述之方法,其中,步驟(d)係於蒸餾塔中於下述條件下施行:205℃至240℃;真空度為1mbar至3mbar;以及,回流比為1至3。
- 如申請專利範圍第1項所述之方法,其中,該第一脂肪酸乙酯係選自由硬脂酸乙酯、油酸乙酯、亞油酸乙酯、棕櫚酸乙酯、辛酸乙酯、及癸酸乙酯所組成之群組的至 少一種脂肪酸乙酯。
- 如申請專利範圍第1項所述之方法,其中,該方法係排除了有機溶劑之加入。
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CN101842020A (zh) * | 2007-09-07 | 2010-09-22 | 日清奥利友集团株式会社 | 硬质脂肪的制造方法 |
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