JP2018521159A - 塩基性第四級アンモニウム塩処理を含む、金属含有グリセリド油から金属を除去する方法 - Google Patents
塩基性第四級アンモニウム塩処理を含む、金属含有グリセリド油から金属を除去する方法 Download PDFInfo
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- JP2018521159A JP2018521159A JP2017561285A JP2017561285A JP2018521159A JP 2018521159 A JP2018521159 A JP 2018521159A JP 2017561285 A JP2017561285 A JP 2017561285A JP 2017561285 A JP2017561285 A JP 2017561285A JP 2018521159 A JP2018521159 A JP 2018521159A
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- Prior art keywords
- oil
- quaternary ammonium
- ammonium salt
- ion
- glyceride
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 91
- 239000002184 metal Substances 0.000 title claims abstract description 91
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- 229910052742 iron Inorganic materials 0.000 claims abstract description 16
- 150000002500 ions Chemical class 0.000 claims abstract description 15
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- 125000005910 alkyl carbonate group Chemical group 0.000 claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 8
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 5
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-M serinate Chemical compound OCC(N)C([O-])=O MTCFGRXMJLQNBG-UHFFFAOYSA-M 0.000 claims description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000010470 pecan oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000010490 pine nut oil Substances 0.000 description 1
- 239000010471 pistachio oil Substances 0.000 description 1
- 229940082415 pistachio oil Drugs 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 238000012546 transfer Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-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
- C11B3/02—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
- C11B3/001—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
-
- 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
- C11B3/12—Refining fats or fatty oils by distillation
- C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Edible Oils And Fats (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Manufacture And Refinement Of Metals (AREA)
Abstract
Description
パーム油は、大量の高飽和脂肪を含有し、高い酸化安定性を有し、コレステロールがもともと低く、そのコストが低いこともあって食品産業では、特定の加工食品製品におけるトランス不飽和脂肪の代替物として、ますます使用されている。しかしながら、その他のグリセリド油と同様、食用にするためには、生のパーム油は、精製法を経て、望ましくない成分を除去しなければならない。生のパーム油は、グリセリンでエステル化されていないモノグリセリド、ジグリセリド、およびトリグリセリド、カロテン、ステロール、また遊離脂肪酸(FFA)を含有する。FFAによって、油の分解、および油焼けの増加につながり、このためこれは、精製工程において除去を望む複数の成分のうちの1つである。
(i)クロム、マンガン、鉄、コバルト、ニッケルおよび銅から成る群からの少なくとも1種の金属を含有するグリセリド油を、塩基性第四級アンモニウム塩を含有する液体と接触させて、処理されたグリセリド油を形成する工程、ここで前記グリセリド油は、前記金属を10mg/kg〜10,000mg/kgの合計量で含有し、かつ塩基性第四級アンモニウム塩は、水酸化物イオン、アルコキシドイオン、アルキル炭酸イオン、炭酸水素イオン、炭酸イオン、セリン酸イオン、プロリン酸イオン、ヒスチジン酸イオン、トレオニン酸イオン、バリン酸イオン、アスパラギン酸イオン、タウリン酸イオン、およびリシン酸イオンから選択される塩基性アニオンと、第四級アンモニウムカチオンとを含有し、および
(ii)グリセリド油を第四級アンモニウム塩と接触させた後、処理されたグリセリド油を、第四級アンモニウムカチオンを含有する塩から分離して、工程(i)で接触させたグリセリド油に比べて、前記金属の量が低下した処理されたグリセリド油を得る工程。
(iii)処理されたグリセリド油を、分離工程(ii)後に、少なくとも1つのさらなる精製工程に供する工程
を有する。
[N(Ra)(Rb)(Rc)(Rd)]+
から選択され、上記式中、Ra、Rb、RcおよびRdはそれぞれ独立して、C1〜C8アルキルから選択され、ここで1つ以上のRa、Rb、RcおよびRdは任意で、C1〜C4アルコキシ、C2〜C8アルコキシアルコキシ、C3〜C6シクロアルキル、−OH、−SH、−CO2Reおよび−OC(O)Reから選択される1〜3個の基、例えば1〜3個の−OH基によって窒素原子と結合されていない炭素原子のところで置換されていてよく、ここでReは、C1〜C6アルキルである。
[N(Ra)(Rb)(Rc)(Rd)]+
から選択されており、上記式中、Ra、Rb、RcおよびRdはそれぞれ独立して、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、sec−ブチル、イソブチルおよびtert−ブチルを含むC1〜C4アルキルから選択され、ここでRa、Rb、RcまたはRdのうち少なくとも1つは、1つの−OH基によってそれぞれ置換されている。置換されたRa、Rb、RcまたはRdは好ましくは、2−ヒドロキシエチル、2−ヒドロキシプロピル、または2−ヒドロキシ−2−メチルエチルである。
(a)コリン脂肪酸塩を、炭酸と接触させる工程、および
(b)コリン重炭酸塩を、工程(a)で形成されたFFAから分離する工程
を含む。
パーム油の酸価(mg KOH/油1g)、およびFFA含分(質量%)の一般的な特定法。
56.1×N×V/m
上記式中、
56.1は、水酸化カリウムの分子量(g/mol)であり、
Vは、使用する水酸化カリウム溶液の体積(ml)であり、
Nは、水酸化カリウム溶液の規定度(mol/l)であり、
mは、パーム油試料の質量(g)である。
質量%FFA=酸価×0.479
油の金属含分は、ICP−AES分析により、表1に示した精製段階に供していない油について、またAAS分析(ASU L 00.00-19/1)により、標準的な方法のDIN EN ISO 11885に従って、1つ以上の精製段階にかけた油について、特定した。
測定されたFFA含分が7.48質量%である生のパーム油(CPO)の試料1kgを、サーモスタット制御式水浴中で50℃に加熱した。それから、均質化したCPOを、2lの撹拌式タンク反応器(その内部で反応器の温度は、循環加熱油によって50℃に維持された)に加えた。それから、CPOのFFA含分に対するコリン重炭酸塩(Sigma-Aldrich UKによる、H2O中で80質量%のもの)の化学量論量を、1分あたり1〜2mlの速度で反応容器に導入した。この混合物を、機械的なオーバーヘッドスターラを用いて500min-1で1時間、撹拌した。その後、この混合物を4000min-1で3分間、遠心分離して、第四級アンモニウムFFA塩を含有する相と、処理されたCPO相とを分離した。分離された油相を分析したところ、FFAを0.18質量%含有し、水を0.11質量%含有することが判明した。CPOの金属濃度、および処理された油相の金属濃度を特定した。その結果は、以下の表2に記載されている。
FFA含分が3.21質量%であると測定された別の生のパーム油(CPO)を用いて、例1を繰り返した。分離された油相を分析したところ、FFAを0.1質量%含有し、水を0.08質量%含有することが判明した。CPOの金属濃度、および処理された油相の金属濃度を特定した。その結果は、表3に記載されている。
測定されたFFA含分が3.97質量%であるCPOの試料を、先の表1で規定した条件を用いて脱ガム、漂白、および脱臭を伴う慣用の物理的な精製法により精製した。質的なパラメータは、油の精製前、および精製後に特定した。その結果は以下の表4に、使用した測定手法とともに示してある。精製油の官能試験は、KIN GmbH Lebensmittel Instituteで、色、味、外観、および臭いを、BVL L 00.90-6に記載された方法(Beuth-Verlagが管理するオンラインデータベースで公開:“Official Collection of Testing Methods according to § 64 LFGB, § 35 of the Draft Tobacco Regulation and pursuant to § 28b of the Genetic Engineering Act”)に従って判断する4人の試験パネリストによっても行った。試験者は、それぞれのパラメータについて1〜5(1/2=消費に不向き、3=充分、4=良好、5=優秀)というグレードで判断し、判断の平均値および中央値を、各パラメータについての最終的な結果として示した。通常、市販に受け入れられると考えられる油の試料のためには、各パラメータについて4または5の値が必要とされる。その結果は、以下の表4に記載されている。
例3で使用したのと同じCPOの試料4kgを、サーモスタット制御式の水浴で50℃に加熱し、それから撹拌式タンク反応器(その内部で反応器の温度は、循環加熱油によって50℃に維持された)に加えた。それから、CPOのFFA含分に対するコリン重炭酸塩(Sigma-Aldrich UKによる、水中で80質量%のもの)の化学量論量を、1分あたり1〜2mlの速度で反応容器に導入した。この混合物を、機械的なオーバーヘッドスターラを用いて500min-1で1時間、撹拌した。その後、この混合物を4000min-1で3分間、遠心分離して、第四級アンモニウムFFA塩を含有する相と、処理されたパーム油相とを分離した。分離された油相を滴定したところ、FFA含分は0.05質量%であることが判明した。
例4の二段階の脱臭を繰り返したのだが、第二の脱臭段階を180℃の温度ではなく、200℃で行った。
例4からの、第四級アンモニウム塩処理されたパーム油の試料を、先に表1に記載したように脱ガム工程および漂白工程にかけ、それから例4の二段階の脱臭を行った。
Claims (23)
- 金属含有グリセリド油から金属を除去する方法であって、以下の工程:
(i)クロム、マンガン、鉄、コバルト、ニッケルおよび銅から成る群からの少なくとも1種の金属を含有するグリセリド油を、塩基性第四級アンモニウム塩を含有する液体と接触させて、処理されたグリセリド油を形成する工程、ここで前記グリセリド油は、前記金属を10mg/kg〜10,000mg/kgの合計量で含有し、かつ塩基性第四級アンモニウム塩は、水酸化物イオン、アルコキシドイオン、アルキル炭酸イオン、炭酸水素イオン、炭酸イオン、セリン酸イオン、プロリン酸イオン、ヒスチジン酸イオン、トレオニン酸イオン、バリン酸イオン、アスパラギン酸イオン、タウリン酸イオン、およびリシン酸イオンから選択される塩基性アニオンと、第四級アンモニウムカチオンとを含有し、および
(ii)グリセリド油を第四級アンモニウム塩と接触させた後、処理されたグリセリド油を、第四級アンモニウムカチオンを含有する塩から分離して、工程(i)で接触させたグリセリド油に比べて、前記金属の量が低下した処理されたグリセリド油を得る工程
を含む、前記方法。 - 以下のさらなる工程:
(iii)分離工程の後に、処理されたグリセリド油を、少なくとも1つのさらなる精製工程に供する工程
を含む、請求項1記載の方法。 - 少なくとも1つのさらなる精製工程が、脱臭工程、好ましくは水蒸気ストリッピングを伴う脱臭工程を含み、該脱臭工程は、160℃〜270℃の温度、好ましくは160℃〜240℃の温度、より好ましくは170〜190℃の温度で行われる、請求項2記載の方法。
- 前記方法はさらに、グリセリド油の少なくとも1つのさらなる精製工程を含み、該精製工程は、工程(i)における塩基性第四級アンモニウム塩による処理より前に行われ、ここで好ましくは少なくとも1つのさらなる精製工程は、漂白および/または脱ガムから選択される、請求項2または3記載の方法。
- 少なくとも1つのさらなる精製工程(iii)が脱臭工程を含み、前記方法は、脱ガム工程および/または漂白工程を含まない、請求項2または3記載の方法。
- 工程(i)における接触より前でグリセリド油中の前記金属の合計量が、50mg/kg〜5,000mg/kg、好ましくは100mg/kg〜2,000mg/kgである、請求項1から5までのいずれか1項記載の方法。
- 工程(ii)で分離された処理されたグリセリド油が前記金属を、工程(i)で接触させた処理されていないグリセリド油における前記金属の合計量の50%未満、好ましくは75%未満の合計量で含有する、請求項1から6までのいずれか1項記載の方法。
- 工程(ii)で分離される塩が、遊離脂肪酸のアニオンを含有する、請求項1から7までのいずれか1項記載の方法。
- 接触工程を80℃未満、好ましくは25〜65℃、より好ましくは35〜55℃の温度で行う、請求項1から8までのいずれか1項記載の方法。
- 第四級アンモニウムカチオンが、
[N(Ra)(Rb)(Rc)(Rd)]+
から選択され、上記式中、Ra、Rb、RcおよびRdはそれぞれ独立して、C1〜C8アルキルから選択され、ここでRa、Rb、RcまたはRdのうち1つ以上は任意で、C1〜C4アルコキシ、C2〜C8アルコキシアルコキシ、C3〜C6シクロアルキル、OH、SH、CO2ReおよびOC(O)Reから選択される1〜3個の基によって窒素原子と結合されていない炭素原子のところで置換されていてよく、ここでReは、C1〜C6アルキルである、
請求項1から9までのいずれか1項記載の方法。 - Ra、Rb、RcおよびRdはそれぞれ独立して、C1〜C4アルキルから選択され、ここでRa、Rb、RcまたはRdのうち少なくとも1つは、1つの−OH基によってそれぞれ置換されている、請求項10記載の方法。
- 第四級アンモニウムカチオンがコリン:
(CH3)3N+CH2CH2OH
である、請求項11記載の方法。 - 塩基性アニオンが、アルキル炭酸イオン、炭酸水素イオンおよび炭酸イオンから選択され、ここで好ましくは塩基性アニオンが、炭酸水素イオンである、請求項1から12までのいずれか1項記載の方法。
- 工程(i)で接触させる第四級アンモニウム塩が、重炭酸コリン:
(CH3)3N+CH2CH2OH HOCOO-
である、請求項13記載の方法。 - 塩基性アニオンが、水酸化物イオンおよびアルコキシドイオンから選択され、ここで好ましくは塩基性アニオンが水酸化物イオンである、請求項1から12までのいずれか1項記載の方法。
- 工程(i)で接触させる塩基性第四級アンモニウム塩が、水酸化コリン:
(CH3)3N+CH2CH2OH OH-
である、請求項15記載の方法。 - 塩基性第四級アンモニウム塩を含有する液体が溶媒を含有し、該液体中の第四級アンモニウム塩の濃度が、15質量%〜90質量%であり、ここで好ましくは前記溶媒が水性溶媒である、請求項1から16までのいずれか1項記載の方法。
- 塩基性第四級アンモニウム塩を含有する液体が、溶媒、好ましくは水性溶媒を含有し、ここで前記液体中の第四級アンモニウム塩の濃度は、50質量%〜90質量%、好ましくは75質量%〜85質量%である、請求項13または14記載の方法。
- 塩基性第四級アンモニウム塩を含有する液体が、溶媒、好ましくは水性溶媒を含有し、ここで前記液体中の第四級アンモニウム塩の濃度は、15質量%〜60質量%、好ましくは40質量%〜50質量%である、請求項15または16記載の方法。
- グリセリド油が植物油であり、ここで好ましくは該植物油が、ココナツ油、トウモロコシ油、綿実油、落花生油、オリーブ油、パーム油、菜種油、米ぬか油、紅花油、大豆油、およびヒマワリ油、またはこれらの混合物から選択される、より好ましくは、ここで前記植物油がパーム油である、請求項1から19までのいずれか1項記載の方法。
- 金属含有グリセリド油の金属含分を低下させるための、グリセリド油を、塩基性第四級アンモニウム塩と接触させる使用であって、塩基性第四級アンモニウム塩は、水酸化物イオン、アルコキシドイオン、アルキル炭酸イオン、炭酸水素イオン、炭酸イオン、セリン酸イオン、プロリン酸イオン、ヒスチジン酸イオン、トレオニン酸イオン、バリン酸イオン、アスパラギン酸イオン、タウリン酸イオン、およびリシン酸イオンから選択される塩基性アニオンと、第四級アンモニウムカチオンとを含有する、前記使用。
- グリセリド油が、請求項20で規定されたものである、請求項21記載の使用。
- 塩基性第四級アンモニウム塩が、請求項10から16までのいずれか1項で規定されたものである、請求項21または22記載の使用。
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EP15169317.3 | 2015-05-27 | ||
PCT/EP2016/061965 WO2016189115A1 (en) | 2015-05-27 | 2016-05-27 | A process for removing metal from a metal-containing glyceride oil comprising a basic quaternary ammonium salt treatment |
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- 2016-05-27 EP EP16727383.8A patent/EP3303531B1/en not_active Not-in-force
- 2016-05-27 PL PL16727383T patent/PL3303531T3/pl unknown
- 2016-05-27 PT PT16727383T patent/PT3303531T/pt unknown
- 2016-05-27 CN CN201680043663.9A patent/CN107849486A/zh active Pending
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PT3303531T (pt) | 2019-06-11 |
PL3303531T3 (pl) | 2019-09-30 |
WO2016189115A1 (en) | 2016-12-01 |
EP3303531A1 (en) | 2018-04-11 |
US10150933B2 (en) | 2018-12-11 |
US20180134988A1 (en) | 2018-05-17 |
AR104787A1 (es) | 2017-08-16 |
EP3303531B1 (en) | 2019-03-20 |
PH12017502136A1 (en) | 2018-05-07 |
ES2727718T3 (es) | 2019-10-18 |
EP3098293A1 (en) | 2016-11-30 |
MY168999A (en) | 2019-01-29 |
CN107849486A (zh) | 2018-03-27 |
DK3303531T3 (da) | 2019-06-11 |
PH12017502136B1 (en) | 2018-05-07 |
BR112017025269A2 (pt) | 2018-08-07 |
HUE043498T2 (hu) | 2019-08-28 |
JP6671396B2 (ja) | 2020-03-25 |
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