CN109762665A - 从甘油三酯油中提取脂肪酸的方法 - Google Patents
从甘油三酯油中提取脂肪酸的方法 Download PDFInfo
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- CN109762665A CN109762665A CN201810378809.6A CN201810378809A CN109762665A CN 109762665 A CN109762665 A CN 109762665A CN 201810378809 A CN201810378809 A CN 201810378809A CN 109762665 A CN109762665 A CN 109762665A
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- oil
- root
- quaternary ammonium
- fatty acid
- triglyceride oil
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/06—Refining fats or fatty oils by chemical reaction with bases
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
Abstract
本发明涉及从甘油三酯油中提取脂肪酸的改进方法。在此情况下,用具有至少一种季铵盐和至少一种包含1至8个碳原子的脂族二醇的水溶液进行甘油三酯油的提取。根据本发明的方法的特征在于高效率。
Description
技术领域
本发明涉及从甘油三酯油中提取脂肪酸的改进方法。在这种情况下,用包含至少一种季铵盐和至少一种包含1至8个碳原子的脂族二醇的水溶液进行甘油三酯油的提取。根据本发明的方法的特征在于高效率。
背景技术
天然脂肪和油具有各种不需要的成分,如金属,游离脂肪酸和磷脂,因此必须进行精制。在天然脂肪和油的精制中,物理精制和化学精制是有区别的。
在主要用于具有低分数(fraction)游离脂肪酸的甘油三酯油的化学精制的情况下,游离脂肪酸通过与碱的反应而被分离出来。在这种情况下形成所谓的皂脚(soapstock),其是碱、游离脂肪酸、游离脂肪酸的盐以及油的含水混合物。这些皂脚是化学精制不希望的副产物,其价值低且用途有限。
在主要用于具有相对高分数的游离脂肪酸的甘油三酯油的物理精制的情况下,与此相比,游离脂肪酸被热分离。以这种方式可以避免皂脚的形成,但与此同时必须施加高温(高达260℃),以便能够通过蒸馏从油中分离出游离脂肪酸。
除了化学和物理精制之外,现有技术中还描述了其它方法,其中游离脂肪酸可以分离出来或者皂料可以被加工。例如,这里使用了液-液提取技术(C.E.C.Rodrigues,C.B.Batista,J.A.Meirelles,Recent Patents on Engineering 2007,1,95-102)。
WO 2016/149692 A1描述了源自皂化反应并且包含脂质的水溶液的酸化。含脂质的原料与碱(特别是氢氧化钠或氢氧化钾)混合并皂化。然后CO2被注入并与反应混合物反应,再除去水相。
另外,US 2,771,480也描述了通过离子交换剂再生脂肪酸。但是,这是非常昂贵的。
CN 106281672 A描述了用抗氧剂(例如生育酚、乳酸盐)及其碱金属盐处理甘油三酯油以除去三氯丙醇及其衍生物。
WO 2012/031176 A1、WO 2016/189114 A1、WO 2016/189115 A1和WO 2016/189328A1描述了用季铵盐及其溶液处理甘油三酯油以去除游离脂肪酸、金属和其它不需要的组分。
在WO 2016/189114 A1中,甘油三酯油用碱性季铵盐的水溶液提取以从其去除脂肪酸。提取后,多个相被分离。为了再生能够在该方法的新提取步骤中使用该水溶液而需要的所述水溶液,将用来自甘油三酯油的脂肪酸盐负载的该水相用CO2加压。结果,由脂肪酸盐形成了游离脂肪酸,其可与水相中分离开。
尽管WO 2016/189114 A1公开了从甘油三酯油中提取游离脂肪酸的可靠方法,但该方法存在问题,特别是在工业规模的应用中。季铵盐是有表面活性的,常用作肥皂和织物柔软剂中的阳离子表面活性剂。因此,甘油三酯油处理后的去除从一开始在技术上就是要求非常高的,因为它们与水和油乳化,并使相分离复杂化。因此,用于从甘油三酯油提取脂肪酸中的季铵盐很难从甘油三酯油中去除,或者不能完全去除。
当使用经提取的甘油三酯油作为食用油时,这是特别不利的:不仅因为一些季铵盐关乎健康,而且特别是胆碱的季铵盐还常常具有臭气味,有时甚至是深色沉积物。这导致提取油质量的明显降低。因此期望进一步改进现有技术的提取技术(例如WO 2016/189114A1)。
因此,本发明的目的是提供一种从甘油三酯油中提取脂肪酸的方法,该方法不具有上述缺点。
最重要的是,应该提供一种方法,其允许重新使用所述相,同时可确保提取的甘油三酯油的高质量。
发明内容
现已令人惊讶地发现,当用铵盐提取甘油三酯油时,如果将具有1至8个碳原子的脂族二醇加入到所述季铵盐中,则所提取油中的季铵盐的分数可显着降低,其中乙二醇和丙二醇类、特别是乙二醇和1,2-丙二醇是最合适的脂族二醇。
因此,本发明涉及从甘油三酯油中提取脂肪酸的方法,其包括以下步骤:
(a)使包含脂肪酸的甘油三酯油T1与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水溶液W1接触,由此获得甘油三酯油相T2和水相W2,其中T2与T1相比具有降低的脂肪酸含量,并且W2与W1相比具有增加的脂肪酸含量;
(b)将甘油三酯油相T2与水相W2中分离开;
其中所述季铵盐包含至少一种季铵阳离子和至少一种碱性阴离子,该碱性阴离子选自氢氧根、烷氧根、烷基碳酸根、碳酸氢根、碳酸根、丝氨酸根、脯氨酸根、组氨酸根、苏氨酸根、缬氨酸根、天冬氨酸根、牛磺酸根、赖氨酸根。
在本发明的上下文中,术语“季铵阳离子”是指具有至少一个氮原子和一个正电荷的阳离子,其中所述氮原子仅与碳原子键合。该氮原子可以是饱和的并且可以通过单键与4个碳原子键合,或者它可以是不饱和的,并通过单键与两个碳原子键合,并通过一个双键与第三个碳原子键合。
如果氮原子是不饱和的,则其也可以是杂芳族环的一部分,例如咪唑鎓阳离子或二烷基咪唑鎓阳离子(例如1-甲基-3-乙基咪唑鎓阳离子,1,3-二甲基咪唑鎓阳离子,1,3-二乙基咪唑鎓阳离子)。
如果氮原子是饱和的,则它也可以是脂环的一部分,例如吡咯烷鎓环或哌啶鎓环。
有利地,氮原子与4个取代或未取代的具有1至12个碳原子的烃基键合,其中这些烃基可以带有其它取代基,其中这些取代基优选在不与带正电的氮原子键合的碳原子上。
在本发明的上下文中,烃基优选意指烷基、环烷基、烯基、炔基或芳基。
本发明中的季铵盐有利地且优选地用作包含盐的液体。它是非挥发性的,并且只以其离子形式作为所述液体的一部分存在。
所述液体优选是所述盐在溶剂中的溶液,所述溶剂例如水。
可能的溶剂选自极性溶剂,例如水、乙醇、甲醇或其混合物。优选使用水作为溶剂。季铵盐可以是离子液体。
有关离子液体的表述对于本领域技术人员来说是已知的,并且例如描述于US 7,638,636B2中。
优选地所述季铵盐阳离子选自根据以下结构的化合物:
[N(Ra)(Rb)(Rc)(Rd)]+,
其中Ra、Rb、Rc和Rd各自独立地选自C1至C8烷基,其中基团Ra、Rb、Rc和Rd中的一个或多个可以任选地在一个碳原子上被选自以下的基团取代:C1-C4烷氧基、C2-C8烷氧基烷氧基、C3-C6环烷基、-OH、-SH、-CO2Re和-OC(O)Re,其中Re=C1-C6烷基,并且其中该一个碳原子优选不直接键合至带正电荷的氮。例如,它可以被1-3个OH基团取代。
所述季铵盐阳离子更优选选自根据以下结构的化合物:
[N(Ra)(Rb)(Rc)(Rd)]+,
其中Ra、Rb、Rc和Rd各自独立地选自C1-C4烷基,包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基和叔丁基,其中Ra、Rb、Rc或Rd的至少一个基团可以在一个不与带正电荷的氮直接键合的碳原子上被OH基取代。取代的基团Ra、Rb、Rc或Rd优选为2-羟基乙基、2-羟基丙基或2-羟基-2-甲基乙基。
最优选使用的季铵盐阳离子是胆碱:(CH3)3N+CH2CH2OH。
所述季铵盐另外包含至少一种选自以下的碱性阴离子:氢氧根、烷氧根、烷基碳酸根、碳酸氢根、碳酸根、丝氨酸根、脯氨酸根、组氨酸根、苏氨酸根、缬氨酸根、天冬氨酸根、牛磺酸根、赖氨酸根。
在一个实施方案中,碱性阴离子选自烷基碳酸根、碳酸氢根、碳酸根、氢氧根、烷氧根。更优选地,其选自烷氧根、碳酸氢根、烷基碳酸根和碳酸根;最优选碳酸氢根。
如果碱性阴离子选自烷氧根或烷基碳酸根,则该烷基是非支链的或支链的,并且是取代的或未取代的。它优选是非支链的且未取代的。
根据本发明的烷基优选包含1至10个碳原子,更优选1至8个,最优选1至4个碳原子。烷基可以选自甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基。还可以使用支链烷基如异丙基、异丁基、仲丁基、叔丁基。烷基特别优选选自甲基、乙基、丙基、丁基,更优选选自甲基、乙基。
在根据本发明的方法中,特别优选的是包含胆碱阳离子的季铵盐。
非常特别优选的是在根据本发明的方法中使用选自以下的季铵盐:胆碱碳酸氢盐:(CH3)3N+CH2CH2OH HOCOO-;氢氧化胆碱:(CH3)3N+CH2CH2OH OH-,烷基碳酸胆碱:(CH3)3N+CH2CH2OH ROCOO-,其中R是具有特别是1至4个碳原子、更优选具有2至3个碳原子的烷基。最优选使用胆碱碳酸氢盐:(CH3)3N+CH2CH2OH HOCOO-。
在根据本发明的方法的步骤(a)中使用的溶液W1还包含至少一种具有1至8、特别是1至6、优选1至5、更优选1至4、甚至更优选1至3个碳原子的脂族二醇,其中所述二醇特别优选地选自乙二醇(=1,2-乙二醇)、丙二醇类,更优选选自乙二醇和1,2-丙二醇。
根据本发明,“丙二醇”意指带有2个OH基团的任何丙烷,不管所述OH基团在哪个碳原子上,优选1,2-丙二醇或1,3-丙二醇。
具有6个碳原子的脂族二醇优选为1,6-己二醇。
作为优选,在根据本发明的方法的步骤(a)中的水溶液W1中,脂族二醇相对于季铵盐的比例使得具有1至8个碳原子的所有脂族二醇的摩尔量基于所有季铵盐的摩尔量计在0.0001%至99.9%,优选0.01%至50.0%,更优选0.1%至40.0%,甚至更优选1.0%至30.0%,最优选10.0%至20.0%,特别优选为15.3%至18.8%以及至多17.6%的范围内,其中所述季铵盐包含至少一种季铵阳离子和至少一种选自以下的碱性阴离子:氢氧根、烷氧根、烷基碳酸根、碳酸氢根、碳酸根、丝氨酸根、脯氨酸根、组氨酸根、苏氨酸根、缬氨酸根、天冬氨酸根、牛磺酸根和赖氨酸根。
在优选的实施方案中,根据本发明的方法包括步骤(c):
(c)将CO2和任选存在的有机溶剂加入到水相W2中,由此获得与W2相比具有更低脂肪酸含量的水相W3,和含脂肪酸的有机相。
在甚至更优选的实施方案中,继续进一步的步骤(d):
(d)从在步骤(c)中获得的含脂肪酸的有机相中分离水相W3。
现已令人惊奇地发现,现有技术中出现的问题,即与脂肪酸分离的甘油三酯油中季铵盐的升高的含量,通过加入具有1至8个碳原子的脂族二醇而代替单独的离子液体可导致提取的甘油三酯油的质量改善,单独添加离子液体是如现有技术中描述的(特别是来自WO 2016/189114A1的胆碱盐)。
根据本发明的特征“甘油三酯油”包括主要成分含量>50重量%的甘油三酯的任何油或脂肪。除了甘油三酯的主要成分之外,所述油或脂肪还可以包含甘油单酯和甘油二酯。
甘油三酯油优选具有天然来源,更优选具有动物或植物来源。甘油三酯油更优选为植物来源的脂肪或油。
对作为植物来源的脂肪和油、并且包含芳香化学物质而考虑的尤其是(可以在括号中指示的拉丁名称是指可以从其衍生的相关油的植物物种):藻油,杏核油(Prunusarmeniaca),坚果油(Argania spinosa),鳄梨油(Persea americana),巴巴苏油(Attaleaspeciosa),棉籽油(Gossypium),山嵛油(Moringa oleifera),琉璃苣油(Boragoofficinalis),荨麻籽油(Urtica pilulifera或Urtica dioica),山毛榉油(Fagus),腰果壳油(Anacardium occidentale),来自柑橘属植物(例如柠檬,桔子,葡萄柚,酸橙)的油,阿苏果油(butter)(Theobroma grandiflorum),红花油(Carthamus),花生油(Arachis hypogaea),玫瑰果油(Rosa),大麻油(Cannabis),榛果油(Corylus avellana),麻风果油(Jatropha curcas),霍霍巴油(Simmondsia chinensis),咖啡豆油(Coffea),可可油(Theobroma cacao),茶籽油(Camellia),巴西棕榈油(Euterpe oleracea),椰子油(Cocos nucifera),南瓜籽油(Cucurbita),假亚麻油(Camelina sativa),亚麻籽油(Linum),玉米油(Zea mays),澳洲坚果油(Macadamia integrifolia,Macadamiatetraphylla),杏仁油(Prunus dulcis),芒果油(Mangifera indica),玉米油(Zea mays),罂粟籽油(Papaver),月见草油(Oenothera biennis),橄榄油(Olea europaea),棕榈油(可从油棕Elaeis属,特别是从非洲油棕Elaeis guineensis、美洲油棕Elaeis oleifera的植物所能得到的油),木瓜籽油(Carica papaya),山核桃油(Carya illinoinensis),紫苏油(Perilla frutescens),松仁油(来自Pinus属的植物),开心果油(Pistacia vera),油菜籽油(Brassica napus),米糠油(Oryza sativa),蓖麻油(Ricinus communis),沙棘仁油(Hippophae rhamnoides的仁),沙棘油(Hippophae rhamnoides的果肉),黑香菜油黑芥(Nigella sativa),芥末油(Brassica nigra),芝麻油(Sesamum indicum),乳木果油(Vitellaria paradoxa),豆油(Glycine max),向日葵油(Helianthus annuus),葡萄籽油(Vitis vinifera),桐油(Vernicia,Aleurites),核桃油(Juglans regia),西瓜籽油(Citrullus lanatus),小麦胚芽油(Triticum)。植物来源的脂肪和油优选选自椰子油、玉米油、棉籽油、橄榄油、棕榈油、花生油、米糠油、豆油、向日葵油、菜籽油、蓖麻油、红花油。植物来源的脂肪和油最优选棕榈油。
对作为动物来源的脂肪和油、并且包含芳香化学物质而考虑的尤其是:Marmot脂肪、黄油脂肪、鱼油、可从甲壳纲动物(例如磷虾)获得的油、鳕鱼肝油、乳脂肪、猪油、鸭油、鹅油、牛油、羊毛蜡。
在本发明的上下文中,“脂肪酸”包括饱和的及单不饱和或多不饱和脂肪酸。根据本发明,该术语还包括(除非在特定情况下另外提及)相关脂肪酸的质子化的形式和去质子化的形式。
不饱和脂肪酸的实例是肉豆蔻脑酸、棕榈油酸、十六碳烯酸(sapienic acid)、油酸、反油酸、异油酸、亚油酸、反亚油酸、α-亚麻酸、花生四烯酸、二十碳五烯酸、芥酸和二十二碳六烯酸。饱和脂肪酸的实例是辛酸、癸酸、十一酸、月桂酸、十三酸、肉豆蔻酸、棕榈酸、十七酸、硬脂酸、十九酸、花生酸、二十一酸、二十二酸、二十四酸和蜡酸。
“棕榈油”表示可从油棕属(Elaeis)植物(棕榈样的或棕榈的科Arecaceae或Palmae的一部分)获得的油,尤其是从非洲油棕(Elaeis guineensis)、美洲油棕(Elaeisoleifera)或其杂交种获得的油。棕榈油可以例如从所述植物的果实或种子得到。
甘油三酯油,特别是步骤(a)中使用的棕榈油可以是未精制的或至少部分精制的。这也包括分馏的甘油三酯油,例如分馏的棕榈油,尤其是棕榈油的硬脂酸馏分或油酸馏分。
“未精制的”甘油三酯油表示根据本发明的甘油三酯油其未经过任何精制步骤。例如,未精制的甘油三酯油尚未通过任何以下的精制步骤:脱胶、脱酸作用、漂白、脱色素化、除臭、冬化。
“精制的”甘油三酯油已通过至少一个精制步骤,例如选自脱胶、脱酸作用、漂白、脱色素化、除臭、冬化中的至少一种。
在根据本发明方法的步骤(a)中,使包含脂肪酸的甘油三酯油T1与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水溶液W1接触。
根据本发明的方法的步骤(a)中的温度无进一步限制。特别地,根据本发明的方法的步骤(a)在<100℃、优选在25℃至90℃、更优选在40℃至90℃、仍更优选在70℃至90℃、最优选在80℃的温度进行。
同样地不另外限制根据本发明的方法的步骤(a)中的压力。特别地,根据本发明的方法的步骤(a)在1巴至100巴的压力下进行,特别是在1巴的标准压力下进行。
包含脂肪酸的甘油三酯油T1可以通过本领域技术人员已知的方法与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水溶液W1接触。接触也可以在其中T1和W1彼此混合的容器中进行。显然的是接触的进行应使得尽可能多的脂肪酸从甘油三酯油T1迁移到水相W1中。为此目的,例如使用机械混合器(例如,可以以间歇模式或连续操作的搅拌罐),超声波混合器或电磁混合器。在接触过程中,可使惰性气体鼓泡通过所得到的混合物。或者,T1和W1也可以在静态混合器如Sulzer混合器或Kenics混合器中混合。
也可将T1和W1以逆流方式连续混合,如在塔(column)中,或以并流方式混合。该塔可以是筛盘塔,规整填料塔或搅拌塔,例如Kühni塔或Scheibel塔。
在并流流动的连续过程中,例如,T1和W1在其接触之前也可以借助于泵各自穿过管,在管的末端它们相遇并混合在一起,以便然后通过流量管(flow tube)R。
在塔中逆流流动的连续过程中,例如,甘油三酯油T1在塔的底端或至少接近塔的底端被引入,而水溶液W1则在塔的顶端或至少接近塔的顶端被引入。
与W1相比脂肪酸含量增加的水相W2然后在塔的底端或接近塔的底端处排出,而与T1相比具有降低的脂肪酸含量的甘油三酯油相T2然后在塔的顶端或接近塔的顶端处被排出。
该塔优选还具有其中可以收集次级料流的底部区域,并且更优选地,甘油三酯油T1然后直接进料至该底部区域的上方。
自然地,也可以使用两个或更多个这样的逆流塔,例如2至6个,或3至5个,或4个。
优选地,该塔也具有规整填料,例如拉西环或多个盘的填料。
用于并流混合的其它可能的装置是混合器沉降器,其可以逆流串联布置。离心提取器也存在,如下面将要进一步描述的那样,其中可以一次性实施根据本发明的方法的步骤a)和b)。
步骤a)优选如下进行,其中T1和W1以并流方式混合,更优选T1和W1在至少一个混合器沉降器中混合。
该方法的步骤(a)中T1和W1的体积比同样无进一步限制。在这种情况下,甘油三酯油T1的体积与水相W1的体积之比特别是在10:1至1:100的范围内,更优选在1:1至1:10的范围内,还更优选为1:1.5至1:4的范围内,还更优选为3:7。
混合,例如在连续接触的情况下的在塔中的接触,可以由本领域技术人员调整,以使得尽可能大部分的甘油三酯油相T1迁移到水相W1中。因此,所述接触例如进行1秒至2小时,特别是30秒至1小时,优选1分钟至50分钟,更优选10分钟至40分钟,最优选20分钟至30分钟。
在根据本发明的方法的步骤(a)中,包含在甘油三酯油T1中的脂肪酸被水相W1中包含的季铵盐中和。特别地,水相W1中所含的所有季铵盐的摩尔量至少等于甘油三酯油T1中所含的所有脂肪酸的摩尔量。包含在水相W1中的所有季铵盐的摩尔量与包含在甘油三酯油T1中的所有脂肪酸的摩尔量的比率优选为1:1至500:1,更优选2:1至200:1,还更优选10:1至100:1,最优选30:1至70:1的范围内。
甘油三酯油中的脂肪酸的含量(fraction)可以通过本领域技术人员已知的方法确定,例如通过用氢氧化钾和酚酞指示剂滴定。在确定了甘油三酯油T1中的脂肪酸的含量之后,本领域技术人员然后也就知道水相W1中所有季铵盐的所需摩尔量必须是多少,其再后就可以相应地进行调节。
在步骤(a)中,使用包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水相W1。水溶液还可以包含除水以外的其它溶剂,例如丙酮、乙酸乙酯、醇类,优选甲醇或乙醇。然而,水相W1优选不含除水之外的任何其它溶剂,这表明根据本发明,所有季铵盐和所有具有1至8个碳原子的脂族二醇的总和与W1中的水的重量比为至少95重量%,优选至少99重量%,更优选至少99.9重量%,W1的剩余物为各种化学物如有机溶剂。
所有季铵盐在水相W1中的总浓度没有进一步限制,基于相W1的总质量,其优选在70-80重量%的范围内,优选75重量%。
在使包含脂肪酸的甘油三酯油T1与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水溶液W1接触时,脂肪酸从甘油三酯油T1至少部分地迁移至水相W1中。因此,在进行步骤(a)时,获得了甘油三酯油相T2和水相W2,其中T2与T1相比具有降低的脂肪酸含量,并且W2与W1相比具有增加的脂肪酸含量。
在根据本发明的方法的步骤(b)中,然后将甘油三酯油相T2与水相W2分离开来。
该分离也可以通过本领域技术人员已知的方法进行,如借助Settler单元中的重力进行。通常,甘油三酯油相T2在此是上层的相,而水相W2是下层的相。或者,甘油三酯油相T2与水相W2的分离也可以在倾析器、水力旋流器、静电聚结器、离心机或膜过滤器压机中进行。在根据本发明的方法的步骤(b)中,甘油三酯油相T2优选在离心机中与水相W2分离开来。
如果盐应该在步骤(a)中的接触过程中至少部分地沉淀,并且作为固体存在于甘油三酯油相T2中,则其也可以通过离心或过滤来除去。溶剂或水也可以加入到含有所述固体的甘油三酯油相T2中,以使固体进入溶液中,并分离如上所述的包含相应盐的所述水溶液。
在本发明的优选实施方案中,根据本发明的方法的步骤(a)和步骤(b)即接触和分离可以在离心分离器中进行,如在US 4,959,158、US 5,571,070、US 5,591,340、US 5,762,800、WO 99/12650和WO 00/29120中所描述的。在这种情况下,T1和W1首先作为单独的料流进入分离器中并在圆形混合区中混合。然后混合物被输送到分离区,在分离区中借助于离心机分离各相。
优选使用一串的(a series of)离心分离器,例如2-6个、3-5个或4个,将甘油三酯油T1引入所述离心分离器串的第一分离器中,并将水相W1引入所述离心分离器串的最后一个分离器中,使得甘油三酯油从该串的第一个分离器流到最后一个分离器,脂肪酸含量随之降低,而水相以相反的方向流过分离器,脂肪酸含量随之增加。然后从该离心分离器串的第一分离器中移出水相W2,并从所述离心分离器串的最后一个分离器中移出甘油三酯油相T2。
在每种情况下,甘油三酯油相T2也可以进料到聚结过滤器中,以从脂肪或油相中除去最后的水溶液滴。这种聚结过滤器是本领域技术人员已知的,并且包括例如经水相和油相润湿的过滤器材料,例如由玻璃或纤维素构成的过滤器材料。
在步骤(b)中从水相W2中分离出甘油三酯油相T2之后,甘油三酯油相T2可然后进料到进一步的后处理或加工。这类步骤可以选自以下的一种或多种:脱胶、脱酸化、冬化、漂白、脱色素化、脱臭。这些步骤对于本领域技术人员是已知的,并且已经在例如WO 2016/189114A1中进行了描述。
可以明显的是,步骤(b)中分离后的甘油三酯油相T2可再次进料至接触步骤(a)一次或多于一次,例如两次至十次,其中该甘油三酯油相T2被用作甘油三酯油T1,并在每个步骤中与新鲜进料的包含碱金属/碱土金属碳酸(氢)盐的水相W1接触,以进一步降低甘油三酯油相T2中脂肪酸的含量。
然后可以将在这些额外的步骤中获得的水相W2全部或部分地进料至随后的步骤(c)等。
任选地,随后可以进行接下来的步骤(c),其中水相被再生。
在该步骤(c)中,将CO2和任选存在的有机溶剂加入水相W2中,从而获得含脂肪酸的有机相及与W2相比具有更低脂肪酸含量的水相W3。合适的条件是本领域技术人员已知的,且例如已在WO 2016/149692A1中描述。
水相W2与CO2和任选存在的有机溶剂的接触可以通过本领域技术人员已知的方法进行。接触可以在气密性可密封的压力容器中进行,其中可以将W2和CO2及任选存在的有机溶剂混合在一起。为此目的,CO2可通过毛细管或可处理气体的搅拌器引入。显然,接触进行的目的是使尽可能多的CO2被引入到水相W2中。为此目的,例如使用机械混合器或电磁混合器。
如果在根据本发明的方法的步骤(c)中添加有机溶剂,则在这种情况下步骤(c)中的W2和有机溶剂的体积比没有进一步的限制。W2的体积与有机溶剂的体积之比特别是在1:100至100:1、优选1:5至5:1、甚至更优选1:2至2:1的范围内。
如果在步骤(c)中使用有机溶剂,则优选二异丙醚、乙酸正丁酯、乙酸乙酯、己烷、1-己醇,优选乙酸正丁酯。
对根据本发明的方法的步骤(c)中的压力和温度没有进一步的限制。
特别地,在加入CO2期间的压力在0.1巴至55巴、优选1巴至20巴、更优选5巴至10巴的范围内。
温度优选为0℃至120℃,更优选为5℃至100℃,仍更优选为10℃至90℃,甚至更优选20℃至80℃,还更优选40℃至60℃,最优选50℃。
步骤(c)中使用的CO2可以源自燃烧过程或高炉(blast furnace)过程,并且可以包含其它成分例如N2O、SO2、H2S、NO2。这些成分可以进一步酸化水相W2,这进一步促进含脂肪酸的有机相的形成。
在步骤(c)结束时,获得含脂肪酸的有机相和与W2相比脂肪酸含量更低的水相W3。
在根据本发明的方法的进一步任选的步骤(d)中,可以将水相W3与步骤(c)中获得的含脂肪酸的有机相中分离开。
这可以通过本领域技术人员熟悉的方法来进行,也可以如对于根据本发明的方法的步骤(b)所描述的那样进行。
在完成步骤(d)之后,获得相W3,其可以随新批次的甘油三酯油添加到新的循环中。
因此,在任选的进一步的步骤(e)中,至少部分水相W3与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的另外的甘油三酯油T3接触,由此得到甘油三酯油相T4和水相W4,其中T4与T3相比具有降低的脂肪酸含量,并且W4与W3相比具有增加的脂肪酸含量。
该进一步的步骤(e)优选如对步骤(a)所描述的进行。根据本发明的方法特别适用于总是再循环所述水相W1,并适用于将其用于新的提取操作。
可以明显的是,对在根据本发明的方法的步骤(b)中获得的甘油三酯相T2可以进行一个或多个进一步的精制步骤,所述精制步骤例如选自脱胶、脱酸作用、漂白、脱色素化、除臭、冬化。
以下实施例旨在阐明本发明,但本发明不限于此。
具体实施方式
实施例
所使用的测试方法:
甘油三酸酯相中的胆碱含量在安捷伦(Agilent)公司的具有QQQ-6430的InfinityII上通过HPLC-ESI-MS测定。为此,将约50mg样品在10mL水丙酮(1:1)(v:v)中稀释,通过HILIC分离方法ESI正模式检测进行分析。结果通过两个校准函数进行评估。相关系数在R2=0.9997/0.9999时确定。
比较例C1
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V2滴定测定)中加入70g胆碱碳酸氢盐水溶液(75.0重量%,密度约1.16g/mL;~5.3摩尔/升),并将混合物在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定测定为0.11重量%。这相当于98.2%的游离脂肪酸的反应。甘油三酯相中的胆碱含量通过HPLC-ESI-MS确定为113 646ppm。
比较例C2
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V 2滴定测定)中加入70g胆碱碳酸氢盐水溶液(80.0重量%,密度约1.17g/mL;~5.7摩尔/升),并将混合物在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定确定为0.08重量%。这相当于98.6%的游离脂肪酸的反应。甘油三酯相中的游离胆碱的含量通过HPLC-ESI-MS确定为6405ppm。
发明实施例E1
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V 2滴定测定)中加入66.5g胆碱碳酸氢盐水溶液(75.0重量%,密度约1.16g/mL;胆碱碳酸氢盐的摩尔浓度~5.3mol/L,相当于胆碱碳酸氢盐0.30摩尔)以及3.5g(56.4毫摩尔)乙二醇,在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定测定为0.16重量%。这相当于97.2%的游离脂肪酸的反应。甘油三酯相中的游离胆碱的含量通过HPLC-ESI-MS确定为389ppm。随后用1.5g(基于甘油三酯相的0.5重量%)Tonsil Supreme 118F漂白土处理获得的甘油三酯相,在95℃下湿式漂白5分钟,并在真空下干式漂白15分钟。过滤掉漂白土后,将甘油三酯相在真空下于240℃脱色10分钟,并用蒸馏水在200℃下蒸烘(steam)另外90分钟。获得的油几乎无色,并具有中性味道和气味(taste and odour)。
发明实施例E2
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V 2滴定测定)中加入66.5g胆碱碳酸氢盐水溶液(80.0重量%,密度约1.17g/mL;胆碱碳酸氢盐的摩尔浓度~5.7mol/L,相当于0.32摩尔的胆碱碳酸氢盐)和3.5g(56.4毫摩尔)的乙二醇,将混合物在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定确定为0.13重量%。这相当于97.8%的游离脂肪酸的反应。甘油三酯相中的游离胆碱的含量通过HPLC-ESI-MS确定为2442ppm。
发明实施例E3
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V 2滴定测定)中加入66.5g胆碱碳酸氢盐水溶液(75.0重量%,密度约1.16g/mL;胆碱碳酸氢盐的摩尔浓度~5.3mol/L,相当于0.30摩尔的胆碱碳酸氢盐)和3.5g(46.0毫摩尔)的1,2-丙二醇,将混合物在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定测定为0.11重量%。这相当于98.2%的游离脂肪酸的反应。甘油三酯相中的游离胆碱的含量通过HPLC-ESI-MS确定为4853ppm。
发明实施例E4
向30g棕榈油(5.5%的游离脂肪酸,通过DGF方法DGF-C-V 2滴定测定)中加入66.5g胆碱碳酸氢盐水溶液(75.0重量%,密度约1.16g/mL;胆碱碳酸氢盐的摩尔浓度~5.3mol/L;相当于0.30摩尔的胆碱碳酸氢盐)和3.5g(29.6毫摩尔)的1,6-己二醇,将混合物在80℃下搅拌1小时。反应完成后,将水相和有机相在分液漏斗中分离。所获得的甘油三酯相中的脂肪酸含量通过滴定确定为0.13重量%。这相当于97.8%的游离脂肪酸的反应。甘油三酯相中的游离胆碱的含量通过HPLC-ESI-MS确定为8924ppm。
实验结果总结在下表1中。
表1
因此,已经表明,令人惊讶的是,只有在使用二醇时才能获得清澈的各相。另外,所得提取油中游离胆碱的不希望的残留物仅在与脂族二醇例如乙二醇或1,2-丙二醇结合后才显着降低。
Claims (10)
1.从甘油三酯油中提取脂肪酸的方法,该方法包括以下步骤:
(a)使包含脂肪酸的甘油三酯油T1与包含至少一种季铵盐和至少一种具有1至8个碳原子的脂族二醇的水溶液W1接触,由此获得甘油三酯油相T2和水相W2,其中T2与T1相比具有降低的脂肪酸含量,而W2与W1相比具有增加的脂肪酸含量;
(b)将甘油三酯油相T2与水相W2分离;
其中所述季铵盐包含至少一种季铵阳离子和至少一种碱性阴离子,所述碱性阴离子选自氢氧根、烷氧根、烷基碳酸根、碳酸氢根、碳酸根、丝氨酸根、脯氨酸根、组氨酸根、苏氨酸根、缬氨酸根、天冬氨酸根、牛磺酸根、赖氨酸根。
2.根据权利要求1所述的方法,其中所述季铵阳离子选自根据以下结构的化合物:
[N(Ra)(Rb)(Rc)(Rd)]+,
其中Ra、Rb、Rc和Rd各自独立地选自C1至C8的烷基,其中基团Ra、Rb、Rc和Rd中的一个或多个任选地在一个碳原子上被选自以下的基团取代:C1至C4的烷氧基,C2至C8的烷氧基烷氧基,C3至C6的环烷基,-OH,-SH,-CO2Re和-OC(O)Re,其中Re=C1至C6的烷基。
3.根据权利要求2所述的方法,其中所述季铵阳离子是胆碱。
4.根据权利要求1至3中任一项所述的方法,其中所述碱性阴离子选自烷基碳酸根、碳酸氢根、碳酸根、氢氧根、烷氧根。
5.根据权利要求4所述的方法,其中所述碱性阴离子是碳酸氢根。
6.根据权利要求1至5中任一项所述的方法,其中所述脂族二醇包含1至4个碳原子。
7.根据权利要求6所述的方法,其中所述脂族二醇选自乙二醇、丙二醇类。
8.根据权利要求1至7中任一项所述的方法,其中步骤a)在70℃至90℃的温度下进行。
9.根据权利要求1至8中任一项所述的方法,其中所述甘油三酯油T1的体积与水相W1的体积之比在10:1至1:100的范围内。
10.根据权利要求1至9中任一项所述的方法,其中在步骤(a)中的所述水溶液W1中,脂族二醇相对于季铵盐的比例使得基于所有季铵盐的摩尔量的所有具有1至8个碳原子的脂族二醇的摩尔量在0.0001%至99.9%的范围内,其中所述季铵盐包含至少一种季铵阳离子和至少一种碱性阴离子,所述碱性阴离子选自氢氧根、烷氧根、烷基碳酸根、碳酸氢根、碳酸根、丝氨酸根、脯氨酸根、组氨酸根、苏氨酸根、缬氨酸根、天冬氨酸根、牛磺酸根和赖氨酸根。
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EP17201077.9 | 2017-11-10 | ||
EP17201077.9A EP3483237A1 (de) | 2017-11-10 | 2017-11-10 | Verfahren zur extraktion von fettsäuren aus triglyceridölen |
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EP (1) | EP3483237A1 (zh) |
JP (1) | JP6652588B2 (zh) |
CN (1) | CN109762665A (zh) |
AR (1) | AR111729A1 (zh) |
BR (1) | BR102018008028A2 (zh) |
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2018
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- 2018-04-19 PH PH12018000112A patent/PH12018000112A1/en unknown
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US20190144778A1 (en) | 2019-05-16 |
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US10301572B1 (en) | 2019-05-28 |
MY176573A (en) | 2020-08-17 |
EP3483237A1 (de) | 2019-05-15 |
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