UA71958C2 - A method for eliminating free fat acids from fats and oils of biological origin or their vapor distillates - Google Patents
A method for eliminating free fat acids from fats and oils of biological origin or their vapor distillates Download PDFInfo
- Publication number
- UA71958C2 UA71958C2 UA2001117942A UA2001117942A UA71958C2 UA 71958 C2 UA71958 C2 UA 71958C2 UA 2001117942 A UA2001117942 A UA 2001117942A UA 2001117942 A UA2001117942 A UA 2001117942A UA 71958 C2 UA71958 C2 UA 71958C2
- Authority
- UA
- Ukraine
- Prior art keywords
- fatty acids
- water
- free fatty
- differs
- extraction
- Prior art date
Links
- 239000003921 oil Substances 0.000 title claims abstract description 79
- 239000003925 fat Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims description 56
- 239000002253 acid Substances 0.000 title claims description 10
- 150000007513 acids Chemical class 0.000 title claims description 7
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 21
- 229930195729 fatty acid Natural products 0.000 claims abstract description 21
- 239000000194 fatty acid Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 238000009835 boiling Methods 0.000 claims abstract description 17
- 150000002897 organic nitrogen compounds Chemical class 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims description 83
- 238000004821 distillation Methods 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 22
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 18
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- 239000001294 propane Substances 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 239000008240 homogeneous mixture Substances 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 claims 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 4
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 claims 2
- VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 claims 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 2
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 claims 2
- HSHIHFMFJLIQDN-UHFFFAOYSA-N 2-(methylamino)butan-1-ol Chemical compound CCC(CO)NC HSHIHFMFJLIQDN-UHFFFAOYSA-N 0.000 claims 2
- UWKDZWSATBBGBN-UHFFFAOYSA-N 2-[ethyl(methyl)amino]ethanol Chemical compound CCN(C)CCO UWKDZWSATBBGBN-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims 2
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 229920000297 Rayon Polymers 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 73
- 235000019197 fats Nutrition 0.000 description 32
- 239000012071 phase Substances 0.000 description 29
- 230000007935 neutral effect Effects 0.000 description 21
- 229930003799 tocopherol Natural products 0.000 description 21
- 239000011732 tocopherol Substances 0.000 description 21
- 125000005456 glyceride group Chemical group 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 235000019482 Palm oil Nutrition 0.000 description 12
- 239000002540 palm oil Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000007670 refining Methods 0.000 description 11
- 125000002640 tocopherol group Chemical class 0.000 description 11
- 235000019149 tocopherols Nutrition 0.000 description 11
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 235000010384 tocopherol Nutrition 0.000 description 10
- 229960001295 tocopherol Drugs 0.000 description 10
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000006392 deoxygenation reaction Methods 0.000 description 9
- 235000014593 oils and fats Nutrition 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 6
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 6
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229960002887 deanol Drugs 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 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 6
- 229940032091 stigmasterol Drugs 0.000 description 6
- 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 6
- 235000016831 stigmasterol Nutrition 0.000 description 6
- 229930003802 tocotrienol Natural products 0.000 description 6
- 239000011731 tocotrienol Substances 0.000 description 6
- 235000019148 tocotrienols Nutrition 0.000 description 6
- 229940068778 tocotrienols Drugs 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229940068065 phytosterols Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 235000019640 taste Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035943 smell Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001746 carotenes Chemical class 0.000 description 2
- 235000005473 carotenes Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical group O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- YLLVPHVZPCGVQN-UHFFFAOYSA-N 1-(propylamino)ethanol Chemical compound CCCNC(C)O YLLVPHVZPCGVQN-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19918097A DE19918097C2 (de) | 1999-04-21 | 1999-04-21 | Verfahren zur Entfernung freier Fettsäuren aus Fetten und Ölen biologischen Ursprungs oder deren Dämpferkondensaten |
PCT/EP2000/003498 WO2000063327A2 (de) | 1999-04-21 | 2000-04-18 | Verfahren zur entfernung freier fettsäuren aus fetten und ölen biologischen ursprungs oder deren dämpferkondensaten |
Publications (1)
Publication Number | Publication Date |
---|---|
UA71958C2 true UA71958C2 (en) | 2005-01-17 |
Family
ID=7905361
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA2001117942A UA71958C2 (en) | 1999-04-21 | 2000-04-18 | A method for eliminating free fat acids from fats and oils of biological origin or their vapor distillates |
Country Status (19)
Country | Link |
---|---|
US (1) | US6579996B2 (zh) |
EP (1) | EP1171555B1 (zh) |
JP (1) | JP3711023B2 (zh) |
CN (1) | CN1133736C (zh) |
AR (1) | AR023552A1 (zh) |
AT (1) | ATE269387T1 (zh) |
AU (1) | AU756898B2 (zh) |
BR (1) | BR0009895A (zh) |
CA (1) | CA2370785A1 (zh) |
DE (2) | DE19918097C2 (zh) |
DK (1) | DK1171555T3 (zh) |
ES (1) | ES2218150T3 (zh) |
IL (1) | IL145977A (zh) |
MX (1) | MXPA01010698A (zh) |
PL (1) | PL350431A1 (zh) |
RU (1) | RU2242505C2 (zh) |
TR (1) | TR200103038T2 (zh) |
UA (1) | UA71958C2 (zh) |
WO (1) | WO2000063327A2 (zh) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10164274B4 (de) * | 2001-12-27 | 2005-12-29 | Energietechnik Leipzig Gmbh | Verfahren und Vorrichtung zur kontinuierlichen Extraktion von freien Fettsäuren, Tocopherolen und/oder Sterolen aus nativen Ölen und zur Umesterung nativer Öle |
NL1020603C2 (nl) * | 2002-05-15 | 2003-11-18 | Tno | Werkwijze voor het drogen van een product met behulp van een regeneratief adsorbens. |
US7806945B2 (en) * | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US7871448B2 (en) | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US8088183B2 (en) | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
US7850745B2 (en) * | 2005-12-01 | 2010-12-14 | Her Majesty In Right Of Canada As Represented By The Minister Of Agriculture And Agri-Food Canada | Method for concentration and extraction of lubricity compounds from vegetable and animal oils |
US20070124992A1 (en) * | 2005-12-01 | 2007-06-07 | Her Majesty In Right Of Canada | Methods for concentration and extraction of lubricity compounds and biologically active fractions from naturally derived fats, oils and greases |
DE102006019763B4 (de) * | 2006-01-23 | 2009-04-09 | Wulfenia Beteiligungs Gmbh | Verfahren zur Gewinnung von Brennstoffen aus pflanzlichen und tierischen Fettabfällen sowie Anlage zur Durchführung des Verfahrens |
EP2616531B1 (en) * | 2010-09-13 | 2017-01-11 | Palsgaard A/S | Refined vegetable oil and a method of producing it |
CN101984028B (zh) * | 2010-10-29 | 2012-07-04 | 湖南农业大学 | 高谷维素米糠油双相萃取脱酸精炼工艺 |
JP5576513B2 (ja) * | 2013-01-11 | 2014-08-20 | 日清オイリオグループ株式会社 | 油脂の製造方法 |
AU2014278303B2 (en) | 2013-06-11 | 2016-12-08 | Renewable Energy Group, Inc. | Production of biodiesel and products obtained therefrom |
CN104531346B (zh) * | 2014-11-26 | 2017-05-17 | 国网河南省电力公司电力科学研究院 | 一种制备低酸值天然酯绝缘油的深度脱酸工艺 |
GB2538760A (en) * | 2015-05-27 | 2016-11-30 | The Queen's Univ Of Belfast | Removal of free fatty acids from glyceride oils |
CN105349259B (zh) * | 2015-12-08 | 2018-12-04 | 江南大学 | 一种植物油的酶法脱酸工艺 |
MY176090A (en) * | 2018-05-08 | 2020-07-24 | Sime Darby Plantation Berhad | An integrated oil extractor apparatus for sterilizing, digesting and pressing oil palm loose fruitlets |
GB2578478B (en) * | 2018-10-29 | 2023-05-03 | Green Lizard Tech Ltd | Chloropropanol removal process |
GB2578570B (en) * | 2018-10-29 | 2022-02-23 | Green Lizard Tech Ltd | Phosphorus removal process |
GB2578477B (en) * | 2018-10-29 | 2023-08-23 | Green Lizard Tech Ltd | Metal removal process |
GB2578479B (en) * | 2018-10-29 | 2023-05-03 | Green Lizard Tech Ltd | Vegetable oil treatment process |
CN112210436A (zh) * | 2020-09-28 | 2021-01-12 | 河南省鲲华生物技术有限公司 | 一种低温亚临界法萃取小麦胚芽油的工艺 |
CN114057574A (zh) * | 2021-12-03 | 2022-02-18 | 浙江工商大学 | 一种制备高纯度epa乙酯的方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1885859A (en) * | 1931-08-21 | 1932-11-01 | Rosenstein Ludwig | Process for refining vegetable oils |
GB478930A (en) * | 1937-05-07 | 1938-01-27 | Bataafsche Petroleum | A process for refining vegetable oils and the like |
US2164012A (en) | 1937-05-19 | 1939-06-27 | Shell Dev | Treatment of nonmineral fatty matter raffinates |
US2157882A (en) | 1937-08-04 | 1939-05-09 | Laval Separator Co De | Process for purifying vegetable and animal oils |
US2200391A (en) * | 1939-01-17 | 1940-05-14 | Pittsburgh Plate Glass Co | Solvent extraction of glyceride oils |
GB764833A (en) * | 1954-05-07 | 1957-01-02 | Benjamin Clayton | Improvements in or relating to treatment of glyceride oils |
DE9013887U1 (de) * | 1990-10-05 | 1991-01-03 | Förster, Martin, 7707 Engen | Futtermittel-Zuführvorrichtung |
-
1999
- 1999-04-21 DE DE19918097A patent/DE19918097C2/de not_active Expired - Fee Related
-
2000
- 2000-04-18 DE DE50006822T patent/DE50006822D1/de not_active Expired - Fee Related
- 2000-04-18 EP EP00922646A patent/EP1171555B1/de not_active Expired - Lifetime
- 2000-04-18 MX MXPA01010698A patent/MXPA01010698A/es unknown
- 2000-04-18 BR BR0009895-7A patent/BR0009895A/pt not_active Application Discontinuation
- 2000-04-18 ES ES00922646T patent/ES2218150T3/es not_active Expired - Lifetime
- 2000-04-18 AT AT00922646T patent/ATE269387T1/de not_active IP Right Cessation
- 2000-04-18 CN CNB008063990A patent/CN1133736C/zh not_active Expired - Fee Related
- 2000-04-18 TR TR2001/03038T patent/TR200103038T2/xx unknown
- 2000-04-18 WO PCT/EP2000/003498 patent/WO2000063327A2/de active IP Right Grant
- 2000-04-18 IL IL14597700A patent/IL145977A/en not_active IP Right Cessation
- 2000-04-18 CA CA002370785A patent/CA2370785A1/en not_active Abandoned
- 2000-04-18 AU AU42964/00A patent/AU756898B2/en not_active Ceased
- 2000-04-18 DK DK00922646T patent/DK1171555T3/da active
- 2000-04-18 RU RU2001130453/13A patent/RU2242505C2/ru not_active IP Right Cessation
- 2000-04-18 PL PL00350431A patent/PL350431A1/xx unknown
- 2000-04-18 JP JP2000612407A patent/JP3711023B2/ja not_active Expired - Fee Related
- 2000-04-18 UA UA2001117942A patent/UA71958C2/uk unknown
- 2000-04-19 AR ARP000101849A patent/AR023552A1/es unknown
-
2001
- 2001-10-20 US US10/046,063 patent/US6579996B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20020111504A1 (en) | 2002-08-15 |
DE19918097A1 (de) | 2000-12-21 |
EP1171555B1 (de) | 2004-06-16 |
DE19918097C2 (de) | 2003-12-24 |
AU756898B2 (en) | 2003-01-23 |
JP2002542379A (ja) | 2002-12-10 |
EP1171555A2 (de) | 2002-01-16 |
AU4296400A (en) | 2000-11-02 |
TR200103038T2 (tr) | 2002-03-21 |
PL350431A1 (en) | 2002-12-16 |
BR0009895A (pt) | 2002-01-15 |
IL145977A (en) | 2004-12-15 |
WO2000063327A2 (de) | 2000-10-26 |
DK1171555T3 (da) | 2004-11-01 |
CN1133736C (zh) | 2004-01-07 |
CN1347445A (zh) | 2002-05-01 |
AR023552A1 (es) | 2002-09-04 |
RU2242505C2 (ru) | 2004-12-20 |
MXPA01010698A (es) | 2002-06-04 |
ES2218150T3 (es) | 2004-11-16 |
US6579996B2 (en) | 2003-06-17 |
WO2000063327A3 (de) | 2001-04-05 |
DE50006822D1 (de) | 2004-07-22 |
CA2370785A1 (en) | 2000-10-26 |
ATE269387T1 (de) | 2004-07-15 |
JP3711023B2 (ja) | 2005-10-26 |
IL145977A0 (en) | 2002-07-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
UA71958C2 (en) | A method for eliminating free fat acids from fats and oils of biological origin or their vapor distillates | |
US11427781B2 (en) | Products produced from distillers corn oil | |
EP1158039A2 (en) | Method for deodorising vegetable oil | |
Rodrigues et al. | Deacidification of vegetable oils by solvent extraction | |
NL7907094A (nl) | Werkwijze voor het behandeling van onzuivere plant- aardige vetten en olieen. | |
CN113710784A (zh) | 氯丙醇去除工艺 | |
EP0228980A1 (en) | A process for the preparation of hexamethyl tetracosanes | |
NO175486B (no) | Fremgangsmåte for fjerning av uönsket lukt fra fettsyreblandinger | |
GB764833A (en) | Improvements in or relating to treatment of glyceride oils | |
GB2451581A (en) | Fatty waste material purification process | |
Drescher et al. | Investigations on physical refining of animal fats and vegetable oils | |
AU739166B2 (en) | Process for obtaining oryzanol | |
CA2020307A1 (en) | Process for soap splitting using a high temperature treatment | |
WO1998012288A1 (de) | Verfahren zur reinigung von fetten und ölen tierischen oder vegetabilischen ursprungs | |
FR2939689A1 (fr) | Procede d'extraction d'un compose minieur d'un corps gras, notamment d'une huile vegetale ou animale ou de leurs co-produits au moyen de terpene. | |
GB2144143A (en) | Refining of palm oils | |
CN113614210A (zh) | 磷去除工艺 | |
US2265020A (en) | Process for refining fatty acids | |
US20010047101A1 (en) | Process for obtaining oryzanol | |
Williams | Processing of oils and fats for edible purposes | |
EP0269904A2 (en) | Process for refining fat | |
Martincic et al. | Separation processes in oil refining technology | |
Myddleton et al. | Fats: natural & synthetic | |
MXPA01005035A (en) | Improved method for refining vegetable oil |