JP2017519892A - 有機オイルを段階的に処理する方法及び装置 - Google Patents
有機オイルを段階的に処理する方法及び装置 Download PDFInfo
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- JP2017519892A JP2017519892A JP2017516197A JP2017516197A JP2017519892A JP 2017519892 A JP2017519892 A JP 2017519892A JP 2017516197 A JP2017516197 A JP 2017516197A JP 2017516197 A JP2017516197 A JP 2017516197A JP 2017519892 A JP2017519892 A JP 2017519892A
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- Prior art keywords
- oil
- acid
- phase
- oil phase
- phospholipids
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- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000012545 processing Methods 0.000 title description 15
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- 239000002253 acid Substances 0.000 claims abstract description 52
- 239000008346 aqueous phase Substances 0.000 claims abstract description 37
- 150000002338 glycosides Chemical class 0.000 claims abstract description 35
- 229930182470 glycoside Natural products 0.000 claims abstract description 34
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 31
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 31
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000001632 sodium acetate Substances 0.000 claims abstract description 16
- 235000017281 sodium acetate Nutrition 0.000 claims abstract description 16
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 10
- 235000021588 free fatty acids Nutrition 0.000 claims description 53
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 33
- 150000004665 fatty acids Chemical group 0.000 claims description 26
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 229930182558 Sterol Natural products 0.000 description 3
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- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 3
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- QFUDHWDUKUCCHZ-UHFFFAOYSA-N methyl hydrogen sulfite Chemical compound COS(O)=O QFUDHWDUKUCCHZ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-WAYWQWQTSA-N myristoleic acid Chemical compound CCCC\C=C/CCCCCCCC(O)=O YWWVWXASSLXJHU-WAYWQWQTSA-N 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
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- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
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- 239000010470 pecan oil Substances 0.000 description 1
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 1
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- 229940068041 phytic acid Drugs 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
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- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
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- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 125000002328 sterol group Chemical group 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
- 235000016831 stigmasterol Nutrition 0.000 description 1
- 229940032091 stigmasterol Drugs 0.000 description 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- HSNQNPCNYIJJHT-ISLYRVAYSA-N trans-octadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCC HSNQNPCNYIJJHT-ISLYRVAYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 238000009875 water degumming Methods 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- C11B3/10—Refining fats or fatty oils by adsorption
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
原料オイルは、例えば、圧縮または抽出方法によって植物から得られる。しかしながら、多種多様な変形例が考えられる。原料オイルは、必ずしも、生きた物質から直接得られる必要はない。しかし、フライオイルの場合には、意図した目的のために一回または数回既に使われていてもよい。
ステップCにおいて前もって除去するのが難しいリン脂質さえも、油相から大量に除去しているので、また、任意ではあるが遊離脂肪酸までもリン脂質から除去しているので、漂白処理(bleaching operation)は極めて効果的になり得る。漂白は、例えば、漂白土類(bleaching earth)によって効果的に達成し得る。
最初のステップは、原料オイル、すなわち処理されるべき有機オイルの準備である。
「Beyer, Walter, “Lehrbuch der Organischen Chemie” 21st edition, S.Hirzel Verlag, 1988-p.248」
生きている植物および動物の個体の実質的に全ての細胞の自然成分として、リン脂質、糖脂質、グリセロ糖脂質、およびスフィンゴ糖脂質などが、これらの個体及び植物から得られるオイルまたは脂肪(例えば、野菜オイル)中に不可避的に存在する。これらの部分は、抽出が行われる組織に依存するだけでなく、抽出方法にも依存する。表1は、オイル及び/または脂肪中に存在し、種々の穀物植物から得られた物質のクラスをまとめている。既に明らかになっていることは、概して中性脂質がオイルまたは脂肪の主要な部分を作り上げているが、リン脂質および糖脂質/グリセロ糖脂質/スフィンゴ糖脂質の部分が非常に変動していることである。例えば、糖脂質、グリセロ糖脂質、およびスフィンゴ糖脂質の部分は、ココナッツオイル中の0.2%から、ボリジオイル中の約2%、米胚芽油中の6.3−7%を経て、アボカドからのオイル中の19.4%に及ぶ範囲である。
表1:種中におけるイオン基を含まない脂質(NL)、リン脂質(PL)、グリセロ等脂質およびスフィンゴ糖脂質と同様の糖脂質(GL)の含有量であり、それぞれ、選択された植物に対してそれらから得られる油の含有量。PLとGLは油の総量に対する割合である。種については、いくつかの場合、種の質量と比較して、油部分(総量)の割合のレベルに関する附記がある。
オイル処理の更なるステップにおいて、いわゆる脱ガムが行われる。この操作では、リン脂質が除去される。これらは、リン含有有機物質であり、それは脂肪の特質を有している。リン脂質は、非水和性リン脂質(NHP)および水和性リン脂質(HB)に区分される。水和性リン脂質の例は、フォスファチジルイノシトール又はその塩、フォスファチジルコリンである。非水和性リン脂質の例は、フォスファチジルエタノールアミン、フォスファチジン酸又はその塩である。リン脂質の典型的なカチオンの例は、ナトリウム、カリウム、カルシウムなどである。
第2ステップBで、先ず、水和性リン脂質及び/または非水和性リン脂質が除去される。非水和性リン脂質は、容易に水和性に変換され得る。
オイル処理の第三ステップIIIにおいて、炭酸水素ナトリウムを添加する。驚くべきことに、炭酸水素ナトリウムの添加により、残留リン脂質の更なる分離、特に非水和性リン脂質、特に例えば溶解塩のようなフォスファチジン酸化合物の付加的な分離が生じることが認められた。
脂肪酸は、マーガリンにおけるように食用脂中の純粋部分として、または塗料およびインクなど、またバイオディーゼル燃料などに利用可能である。
知られているように、遊離脂肪酸は、容易に酸化物の形成に入り込むことができる。精製オイル及びオイル派生物の品質を維持するために、これらの遊離脂肪酸は、処理後の油相から除去されなければならない。これは、第4ステップDで行われる。そこでは、処理後の油相がアルカリ剤と混合される。この剤は、好ましくは、アルカリ金属水酸化物溶液、言い換えれば、水酸化ナトリウムまたは水酸化カリウム溶液であり、水酸化ナトリウム溶液であれば特に効率的でコスト的にも有利である。
最終的に、主要産物、すなわちオイル及び脂肪を、漂白及び/または脱臭処理によってさらに精製する。
オイル処理の第3ステップCにおいて、炭酸水素ナトリウムに代えて、選択的に、酢酸ナトリウムを添加することができる。驚くべきことに、酢酸ナトリウムの添加は、液相中にステリルグリコシドを付加的に蓄積することによって達成される。これらのグリコシドは、脱ガムされたオイル部分から除去されたものである。同時に、残留リン脂質、遊離脂肪酸、および例えば葉緑素のようなアルカリ土類金属化合物が油相中に優先的にまたはほぼ完全に残る。
第四ステップDでは、アルカリ剤が処理された油相に添加され、その系は、無極性の油相と極性のある水溶性セッケン相に分かれる。ここで、剤は、好ましくは、アルカリ金属水酸化物溶液、言い換えれば、水酸化ナトリウムまたは水酸化カリウム溶液であり、水酸化ナトリウム溶液を使用すれば、特に好ましいことが証明される。
ナタネから採取した圧搾油として、原料オイル(FFA含有量0.48wt%,H2O含有量0.05wt%,鉄含有量1.13ppm,リン含有量80.42ppm,マグネシウム含有量8.47ppm,カルシウム含有量45.10ppm)が、フィードタンク(フィードタンク1)に導入される。
ナタネからの圧搾油として、原料オイル(FFA含有量43wt%,H2O含有量0.05wt%,鉄含有量0.60ppm,リン含有量52.52ppm,マグネシウム含有量5.43ppm,カルシウム含有量31.33ppm)がフィードタンク(フィードタンク1)に導入される。
ナタネからの圧搾油として、原料オイル(FFA含有量0.54wt%,H2O含有量0.05wt%,鉄含有量0.53ppm,リン含有量78.32ppm,マグネシウム含有量5.70ppm,カルシウム含有量33.04ppm)がフィードタンク(フィードタンク1)に導入される。
原料オイルA1は、水性クエン酸溶液(33%強、添加:1000ppm)を用いて85℃で処理され、シェアリングヘッドミキサー(shearing head mixer)を用いて30秒間混合された。10分間の反応時間経過後、サンプルを取り出し、油相A2を測定した。
Claims (16)
- 有機オイルを段階的に処理する方法であって、
(A)原料オイルを準備するステップと、
(B)水及び/または酸を原料オイルに添加することによって原料オイルを脱ガムして少なくとも水性相と油相の二つの相を形成し、油相からリン脂質が豊富な水性層を分離するステップと、
(C)炭酸水素ナトリウム及び/または酢酸ナトリウムをステップBからの油相に添加し、油相から、溶液中または水性相の懸濁液中にアルカリ土類金属化合物及び/またはリン脂質及び/またはステリルグリコシドを除去するステップとを備える、方法。 - 前記脱ガムは、クエン酸、酢酸、ギ酸、シュウ酸、硝酸、塩酸、硫酸及び/またはリン酸からなる酸から選ばれた一つまたはそれ以上の酸を添加することによって行われる、請求項1に記載の方法。
- ステップB及び/またはステップCは、65℃を超える温度、好ましくは66〜95℃の範囲の温度で行われる、請求項1または2に記載の方法。
- ステップCにおいて、炭酸水素ナトリウム及び/または酢酸ナトリウムは、粉末または懸濁液として油相に添加される、請求項1〜3のいずれかに記載の方法。
- 水の添加は、粉末の添加の前または後に行われる、請求項4に記載の方法。
- ステップCにおいて、油相の全重量を基礎にして、0.1wt%の炭酸水素ナトリウム及び/または酢酸ナトリウムが添加される、請求項1〜5のいずれかに記載の方法。
- ステップCにおいて、油相の全重量を基礎にして、少なくとも1.0wt%の水が添加される、請求項1〜6のいずれかに記載の方法。
- ステップCに従った炭酸水素ナトリウムの添加は、水相の薄霧及び/または油相中に見られるリンの含有量及び/または油相中に見られるリンの含有量が特定の設定値を下回るまで、繰り返される、請求項1〜7のいずれかに記載の方法。
- ステップCにおいて炭酸水素ナトリウムを添加した後に、油相からの1%未満の遊離脂肪酸の除去に相当する遊離脂肪酸部分を備える水性相が除去される、請求項1〜8のいずれかに記載の方法。
- ステップCにおいて炭酸水素ナトリウムを添加した後に、油相からの0.2%未満の遊離脂肪酸の除去に相当する遊離脂肪酸部分を備える水性相が除去される、請求項1〜9のいずれかに記載の方法。
- ステップCにおいて酢酸ナトリウムを添加した後に、溶液または懸濁液中に有機成分が存在している水性相が除去され、前記有機成分は、ステリルグリコシドを、30wt%を超える範囲まで、好ましくは50wt%を超える範囲まで備えている、請求項1〜10のいずれかに記載の方法。
- ステップCに続き、ステップDにおいて、ステップCからの油相にアルカリ剤を添加して遊離脂肪酸を加水分解し、これらの加水分解した脂肪酸を油相から除去する、請求項1〜11のいずれかに記載の方法。
- 加水分解した脂肪酸は、3wt%未満、好ましくは1wt%未満の有機不純物を有する、請求項1〜12のいずれかに記載の方法。
- ステップCまたはステップDに続いて、ステップCからの油相は漂白され、及び/または脱臭される、請求項1〜13のいずれかに記載の方法。
- ステップDにおいて添加されたアルカリ剤は、無機アルカリ金属水酸化物溶液、好ましくは水酸化ナトリウム溶液である、請求項1〜14のいずれかに記載の方法。
- 請求項1に記載の方法を実施するように設計された装置。
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KR20220138971A (ko) * | 2021-04-07 | 2022-10-14 | 농업회사법인 크레이지피넛 주식회사 | 땅콩오일 정제방법 |
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EP3098292A1 (en) | 2015-05-27 | 2016-11-30 | Evonik Degussa GmbH | A process for refining glyceride oil comprising a basic quaternary ammonium salt treatment |
DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
EP3257568B1 (de) | 2016-06-14 | 2019-09-18 | Evonik Degussa GmbH | Verfahren zur entfeuchtung von feuchten gasgemischen mit ionischen flüssigkeiten |
DE102016210484A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210478A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
WO2019092017A1 (de) | 2017-11-10 | 2019-05-16 | Evonik Degussa Gmbh | Verfahren zur extraktion von fettsäuren aus triglyceridölen |
EP3483237A1 (de) | 2017-11-10 | 2019-05-15 | Evonik Degussa GmbH | Verfahren zur extraktion von fettsäuren aus triglyceridölen |
WO2019092013A1 (de) | 2017-11-10 | 2019-05-16 | Evonik Degussa Gmbh | Verfahren zur extraktion von fettsäuren aus triglyceridölen |
WO2019157334A1 (en) | 2018-02-09 | 2019-08-15 | Poet Research, Inc. | Methods of refining a grain oil composition to make one or more grain oil products, and related systems |
CA3103242C (en) | 2018-06-11 | 2023-08-29 | Poet Research, Inc. | Methods of refining a grain oil composition feedstock, and related systems, compositions and uses |
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