CA2442063C - Separation of plant oil triglyceride mixtures by solid bed adsorption - Google Patents
Separation of plant oil triglyceride mixtures by solid bed adsorption Download PDFInfo
- Publication number
- CA2442063C CA2442063C CA2442063A CA2442063A CA2442063C CA 2442063 C CA2442063 C CA 2442063C CA 2442063 A CA2442063 A CA 2442063A CA 2442063 A CA2442063 A CA 2442063A CA 2442063 C CA2442063 C CA 2442063C
- Authority
- CA
- Canada
- Prior art keywords
- adsorbent
- percent
- desorbent
- triglyceride
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 239000010773 plant oil Substances 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 98
- 238000001179 sorption measurement Methods 0.000 title claims description 16
- 239000007787 solid Substances 0.000 title abstract description 10
- 238000000926 separation method Methods 0.000 title description 35
- 239000003463 adsorbent Substances 0.000 claims abstract description 126
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 95
- 239000000194 fatty acid Substances 0.000 claims abstract description 95
- 229930195729 fatty acid Natural products 0.000 claims abstract description 95
- 238000000034 method Methods 0.000 claims abstract description 90
- 239000000284 extract Substances 0.000 claims abstract description 79
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000002245 particle Substances 0.000 claims abstract description 31
- 239000004359 castor oil Substances 0.000 claims abstract description 17
- 235000019438 castor oil Nutrition 0.000 claims abstract description 17
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 17
- 240000001689 Cyanthillium cinereum Species 0.000 claims abstract description 16
- 235000004443 Ricinus communis Nutrition 0.000 claims abstract description 15
- 241000390166 Physaria Species 0.000 claims abstract description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 89
- 239000003921 oil Substances 0.000 claims description 36
- 235000019198 oils Nutrition 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 26
- ZEMPKEQAKRGZGQ-UHFFFAOYSA-N Triricinolein Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC(O)CCCCCC)COC(=O)CCCCCCCC=CCC(O)CCCCCC ZEMPKEQAKRGZGQ-UHFFFAOYSA-N 0.000 claims description 24
- ZEMPKEQAKRGZGQ-VBJOUPRGSA-N triricinolein Chemical group CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC)COC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-VBJOUPRGSA-N 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 150000003626 triacylglycerols Chemical class 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 12
- 239000011148 porous material Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- 229960003656 ricinoleic acid Drugs 0.000 claims description 8
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- 235000021355 Stearic acid Nutrition 0.000 claims description 6
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 6
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 229960004488 linolenic acid Drugs 0.000 claims description 6
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 239000008117 stearic acid Substances 0.000 claims description 6
- OONXYOAWMIVMCI-UHFFFAOYSA-N D-Lesquerolinsaeure Natural products CCCCCCC(O)CC=CCCCCCCCCCC(O)=O OONXYOAWMIVMCI-UHFFFAOYSA-N 0.000 claims description 5
- 235000021314 Palmitic acid Nutrition 0.000 claims description 5
- 238000003795 desorption Methods 0.000 claims description 5
- OONXYOAWMIVMCI-KWRJMZDGSA-N lesquerolic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCCCC(O)=O OONXYOAWMIVMCI-KWRJMZDGSA-N 0.000 claims description 5
- CCPPLLJZDQAOHD-UHFFFAOYSA-N vernolic acid Natural products CCCCCC1OC1CC=CCCCCCCCC(O)=O CCPPLLJZDQAOHD-UHFFFAOYSA-N 0.000 claims description 5
- CCPPLLJZDQAOHD-BEBBCNLGSA-N (-)-vernolic acid Chemical compound CCCCC[C@@H]1O[C@@H]1C\C=C/CCCCCCCC(O)=O CCPPLLJZDQAOHD-BEBBCNLGSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 239000002952 polymeric resin Substances 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 2
- 235000020778 linoleic acid Nutrition 0.000 claims 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims 1
- -1 fatty acid triglyceride esters Chemical class 0.000 abstract description 19
- 230000000274 adsorptive effect Effects 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 8
- 239000003208 petroleum Substances 0.000 abstract description 4
- 239000012141 concentrate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 70
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000021251 pulses Nutrition 0.000 description 8
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 125000005457 triglyceride group Chemical group 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- 238000010977 unit operation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 0 C*C(C(*)C(*)C(*)OC(C)(*)C(C*)N=O)OC(*)C(*)(**(C)*****[N+](*)[O-])O Chemical compound C*C(C(*)C(*)C(*)OC(C)(*)C(C*)N=O)OC(*)C(*)(**(C)*****[N+](*)[O-])O 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000893896 Physaria fendleri Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 241000449979 Stokesia <Ciliophora> Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- MWQWJUDADIEXCM-UHFFFAOYSA-N dec-1-en-4-ol Chemical compound CCCCCCC(O)CC=C MWQWJUDADIEXCM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000506 liquid--solid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- CCPPLLJZDQAOHD-FLIBITNWSA-N vernolic acid Chemical compound CCCCCC1OC1C\C=C/CCCCCCCC(O)=O CCPPLLJZDQAOHD-FLIBITNWSA-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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- 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
-
- 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
- C11B7/0058—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 or mixtures of solvents of different natures or compositions used in succession
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28546401P | 2001-04-20 | 2001-04-20 | |
| US60/285,464 | 2001-04-20 | ||
| PCT/US2002/008708 WO2002086039A1 (en) | 2001-04-20 | 2002-03-21 | Separation of plant oil triglyceride mixtures by solid bed adsorption |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2442063A1 CA2442063A1 (en) | 2002-10-31 |
| CA2442063C true CA2442063C (en) | 2011-02-22 |
Family
ID=23094339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2442063A Expired - Fee Related CA2442063C (en) | 2001-04-20 | 2002-03-21 | Separation of plant oil triglyceride mixtures by solid bed adsorption |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7097770B2 (enExample) |
| EP (1) | EP1383854B1 (enExample) |
| JP (1) | JP2004536167A (enExample) |
| KR (1) | KR20030090749A (enExample) |
| CN (1) | CN100554392C (enExample) |
| AR (1) | AR035862A1 (enExample) |
| BR (1) | BR0208770A (enExample) |
| CA (1) | CA2442063C (enExample) |
| DE (1) | DE60218834T2 (enExample) |
| MX (1) | MXPA03009584A (enExample) |
| PE (1) | PE20021111A1 (enExample) |
| RU (1) | RU2003133734A (enExample) |
| WO (1) | WO2002086039A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743509B2 (en) † | 2002-10-01 | 2004-06-01 | Dow Corning Corporation | Method of treating precipitated calcium carbonate fillers |
| US7862546B2 (en) | 2003-06-16 | 2011-01-04 | Ethicon Endo-Surgery, Inc. | Subcutaneous self attaching injection port with integral moveable retention members |
| US8715243B2 (en) | 2003-06-16 | 2014-05-06 | Ethicon Endo-Surgery, Inc. | Injection port applier with downward force actuation |
| US7850660B2 (en) * | 2003-12-19 | 2010-12-14 | Ethicon Endo-Surgery, Inc. | Implantable medical device with simultaneous attachment mechanism and method |
| US7897798B2 (en) | 2006-08-04 | 2011-03-01 | Mcneff Research Consultants, Inc. | Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same |
| US8445709B2 (en) * | 2006-08-04 | 2013-05-21 | Mcneff Research Consultants, Inc. | Systems and methods for refining alkyl ester compositions |
| CA2678519A1 (en) * | 2007-02-13 | 2008-08-21 | Mcneff Research Consultants, Inc. | Devices and methods for selective removal of contaminants from a composition |
| US8017796B2 (en) * | 2007-02-13 | 2011-09-13 | Mcneff Research Consultants, Inc. | Systems for selective removal of contaminants from a composition and methods of regenerating the same |
| US7943791B2 (en) * | 2007-09-28 | 2011-05-17 | Mcneff Research Consultants, Inc. | Methods and compositions for refining lipid feed stocks |
| US8097049B2 (en) * | 2008-02-07 | 2012-01-17 | The Dallas Group Of America, Inc. | Biodiesel purification by a continuous regenerable adsorbent process |
| US20100331559A1 (en) * | 2008-02-21 | 2010-12-30 | Dow Global Technologies Inc. | Separation of natural oil-derived aldehydes or hydroxy methyl esters using process chromatography |
| US8232419B2 (en) * | 2008-10-02 | 2012-07-31 | The Dallas Group Of America | Triacylglycerol purification by a continuous regenerable adsorbent process |
| US8361174B2 (en) * | 2008-10-07 | 2013-01-29 | Sartec Corporation | Catalysts, systems, and methods for producing fuels and fuel additives from polyols |
| US9102877B2 (en) * | 2008-11-12 | 2015-08-11 | Sartec Corporation | Systems and methods for producing fuels from biomass |
| EP2489276B1 (en) * | 2011-02-17 | 2013-10-16 | Neste Oil Oyj | Oil recovery method |
| KR101409121B1 (ko) * | 2011-04-13 | 2014-06-18 | 경상대학교산학협력단 | 폐식물성 오일 기반 바이오매스 탄성체의 제조방법 |
| EP2801604B1 (en) | 2013-05-07 | 2017-04-12 | Groupe Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| CN105505574A (zh) * | 2015-12-04 | 2016-04-20 | 南京威尔化工有限公司 | 一种层析分离制备高纯蓖麻油的方法 |
| EP3429743B1 (en) | 2016-03-14 | 2021-01-06 | 3M Innovative Properties Company | Composite granules including polymeric sorbent for aldehydes |
| US10239812B2 (en) | 2017-04-27 | 2019-03-26 | Sartec Corporation | Systems and methods for synthesis of phenolics and ketones |
| EP3638414B1 (en) * | 2017-06-16 | 2024-03-27 | 3M Innovative Properties Company | Polymeric sorbents for aldehydes |
| CN107955706A (zh) * | 2017-12-14 | 2018-04-24 | 广州白云山汉方现代药业有限公司 | 一种脱除中长链结构酯中甘油二酯的方法 |
| US10544381B2 (en) | 2018-02-07 | 2020-01-28 | Sartec Corporation | Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid |
| US10696923B2 (en) | 2018-02-07 | 2020-06-30 | Sartec Corporation | Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1767041A (en) * | 1926-04-14 | 1930-06-24 | Wm S Merrell Co | Caster-oil soap and process of making castor-oil soap |
| US2553288A (en) * | 1944-12-07 | 1951-05-15 | Swift & Co | Solvent treatment |
| US2581369A (en) * | 1948-05-29 | 1952-01-08 | Petrolite Corp | Oxyethylated hydrophile derivatives of certain fractional esters of triricinolein |
| US2985589A (en) * | 1957-05-22 | 1961-05-23 | Universal Oil Prod Co | Continuous sorption process employing fixed bed of sorbent and moving inlets and outlets |
| US3173935A (en) * | 1961-04-14 | 1965-03-16 | Chemetron Corp | Separation of fatty mixtures |
| US3165540A (en) | 1961-09-05 | 1965-01-12 | Charles F Krewson | Process for isolation of divernolin and trivernolin |
| US3647684A (en) * | 1968-04-17 | 1972-03-07 | Dexter Corp | Adding cationic material to silicic acid sorbent chromatographic sheet for improved performance |
| US4210594A (en) | 1977-12-08 | 1980-07-01 | The Procter & Gamble Company | Process for separating esters of fatty acids |
| US4213913A (en) | 1979-03-12 | 1980-07-22 | Uop Inc. | Two-stage process for separating mixed fatty-acid esters |
| US4297292A (en) | 1979-05-25 | 1981-10-27 | The Procter & Gamble Company | Fractionation of triglyceride mixtures |
| EP0062114A1 (en) * | 1981-04-08 | 1982-10-13 | THE PROCTER & GAMBLE COMPANY | Fractionation of triglyceride mixtures |
| US4402832A (en) | 1982-08-12 | 1983-09-06 | Uop Inc. | High efficiency continuous separation process |
| US4784807A (en) * | 1987-07-06 | 1988-11-15 | Uop Inc. | Process for separating triglylcerides by degree of unsaturation |
| US4770819A (en) * | 1987-07-06 | 1988-09-13 | Uop Inc. | Process for separating di- and triglycerides |
| US4961881A (en) * | 1988-02-17 | 1990-10-09 | Uop | Process for separating triglycerides and regenerating absorbent used in said separation process |
| US5068418A (en) | 1989-05-08 | 1991-11-26 | Uop | Separation of lactic acid from fermentation broth with an anionic polymeric absorbent |
| JPH0384099A (ja) * | 1989-08-28 | 1991-04-09 | Ito Seiyu Kk | 水添ヒマシ油改質物の製造法 |
| US5225580A (en) | 1990-08-16 | 1993-07-06 | Uop | Process for separating fatty acids and triglycerides |
| US5300242A (en) * | 1992-03-05 | 1994-04-05 | The Lubrizol Corporation | Metal overbased and gelled natural oils |
| DE69401506T2 (de) * | 1993-04-29 | 1997-09-11 | Norsk Hydro As | Verfahren zur chromatografischer fraktionierung von fettsäuren und ihre derivaten |
| US5414100A (en) * | 1993-08-27 | 1995-05-09 | Howard University | Deacidification of vegetable oils |
-
2002
- 2002-03-21 KR KR10-2003-7013538A patent/KR20030090749A/ko not_active Withdrawn
- 2002-03-21 JP JP2002583555A patent/JP2004536167A/ja active Pending
- 2002-03-21 EP EP02715176A patent/EP1383854B1/en not_active Expired - Lifetime
- 2002-03-21 WO PCT/US2002/008708 patent/WO2002086039A1/en not_active Ceased
- 2002-03-21 RU RU2003133734/13A patent/RU2003133734A/ru not_active Application Discontinuation
- 2002-03-21 BR BR0208770-7A patent/BR0208770A/pt active Search and Examination
- 2002-03-21 DE DE60218834T patent/DE60218834T2/de not_active Expired - Lifetime
- 2002-03-21 US US10/471,875 patent/US7097770B2/en not_active Expired - Fee Related
- 2002-03-21 CN CNB028085159A patent/CN100554392C/zh not_active Expired - Fee Related
- 2002-03-21 MX MXPA03009584A patent/MXPA03009584A/es unknown
- 2002-03-21 CA CA2442063A patent/CA2442063C/en not_active Expired - Fee Related
- 2002-04-19 AR ARP020101446A patent/AR035862A1/es active IP Right Grant
- 2002-04-19 PE PE2002000328A patent/PE20021111A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1383854A1 (en) | 2004-01-28 |
| CN1503836A (zh) | 2004-06-09 |
| DE60218834D1 (de) | 2007-04-26 |
| KR20030090749A (ko) | 2003-11-28 |
| WO2002086039A1 (en) | 2002-10-31 |
| AR035862A1 (es) | 2004-07-21 |
| JP2004536167A (ja) | 2004-12-02 |
| PE20021111A1 (es) | 2002-12-16 |
| CA2442063A1 (en) | 2002-10-31 |
| US20040094477A1 (en) | 2004-05-20 |
| RU2003133734A (ru) | 2005-02-27 |
| CN100554392C (zh) | 2009-10-28 |
| EP1383854B1 (en) | 2007-03-14 |
| BR0208770A (pt) | 2004-06-22 |
| US7097770B2 (en) | 2006-08-29 |
| DE60218834T2 (de) | 2007-10-31 |
| MXPA03009584A (es) | 2004-05-24 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170321 |