BR112013033261B1 - Processo para produzir um éster de ácido graxoepoxidado com cor reduzidaa - Google Patents
Processo para produzir um éster de ácido graxoepoxidado com cor reduzidaa Download PDFInfo
- Publication number
- BR112013033261B1 BR112013033261B1 BR112013033261A BR112013033261A BR112013033261B1 BR 112013033261 B1 BR112013033261 B1 BR 112013033261B1 BR 112013033261 A BR112013033261 A BR 112013033261A BR 112013033261 A BR112013033261 A BR 112013033261A BR 112013033261 B1 BR112013033261 B1 BR 112013033261B1
- Authority
- BR
- Brazil
- Prior art keywords
- color
- borohydride
- catalyst
- fatty acid
- epoxidized
- Prior art date
Links
- -1 FATTY ACID ESTER Chemical class 0.000 title claims abstract description 68
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 63
- 239000000194 fatty acid Substances 0.000 title claims abstract description 63
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 62
- 230000008569 process Effects 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 150000002148 esters Chemical class 0.000 claims abstract description 45
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 27
- 238000009884 interesterification Methods 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims description 66
- 239000011541 reaction mixture Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 10
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 abstract description 69
- 239000003921 oil Substances 0.000 abstract description 63
- 239000003925 fat Substances 0.000 abstract description 45
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract description 16
- 239000003086 colorant Substances 0.000 abstract description 4
- 239000008037 PVC plasticizer Substances 0.000 abstract description 3
- 235000019198 oils Nutrition 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 235000019197 fats Nutrition 0.000 description 44
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
- 229920001944 Plastisol Polymers 0.000 description 31
- 239000004999 plastisol Substances 0.000 description 31
- 229920000642 polymer Polymers 0.000 description 28
- 239000004800 polyvinyl chloride Substances 0.000 description 23
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- 229920000915 polyvinyl chloride Polymers 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000008158 vegetable oil Substances 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 235000015112 vegetable and seed oil Nutrition 0.000 description 9
- 235000012424 soybean oil Nutrition 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000003549 soybean oil Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VYCIHDBIKGRENI-UHFFFAOYSA-N 1,3-bis[2,6-di(propan-2-yl)phenyl]-2h-imidazol-1-ium-2-ide Chemical group CC(C)C1=CC=CC(C(C)C)=C1N1C=CN(C=2C(=CC=CC=2C(C)C)C(C)C)[C]1 VYCIHDBIKGRENI-UHFFFAOYSA-N 0.000 description 4
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000010773 plant oil Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003225 biodiesel Substances 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003017 thermal stabilizer Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- 229920006385 Geon Polymers 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- 239000000446 fuel Substances 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
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- 239000002808 molecular sieve Substances 0.000 description 2
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- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 229920001291 polyvinyl halide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 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 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000006724 (C1-C5) alkyl ester group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910002837 PtCo Inorganic materials 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- WSNSMPZJJIYZCV-UHFFFAOYSA-N [Na]C Chemical class [Na]C WSNSMPZJJIYZCV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 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 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical class CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
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- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
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- 239000002649 leather substitute Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
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- 239000004006 olive oil Substances 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- 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
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fats And Perfumes (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161501312P | 2011-06-27 | 2011-06-27 | |
| PCT/US2012/038760 WO2013002913A1 (en) | 2011-06-27 | 2012-05-21 | Reduced color epoxidized esters from epoxidized natural fats and oils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112013033261A2 BR112013033261A2 (pt) | 2017-03-01 |
| BR112013033261B1 true BR112013033261B1 (pt) | 2020-01-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112013033261A BR112013033261B1 (pt) | 2011-06-27 | 2012-05-21 | Processo para produzir um éster de ácido graxoepoxidado com cor reduzidaa |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9708571B2 (https=) |
| EP (1) | EP2723706B1 (https=) |
| JP (1) | JP6178310B2 (https=) |
| CN (1) | CN103732570B (https=) |
| BR (1) | BR112013033261B1 (https=) |
| CA (1) | CA2840053C (https=) |
| ES (1) | ES2784130T3 (https=) |
| IN (1) | IN2014DN00197A (https=) |
| PT (1) | PT2723706T (https=) |
| WO (1) | WO2013002913A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3212702B1 (en) * | 2014-10-27 | 2021-08-25 | Dow Global Technologies LLC | Plasticizer compositions and methods for making plasticizer compositions |
| WO2021055815A1 (en) | 2019-09-18 | 2021-03-25 | Iowa State University Research Foundation, Inc. | Biosolvents useful for improved asphalt products utilizing recycled asphalt pavement or other brittle asphalt binders such as vacuum tower bottom |
| WO2025122999A1 (en) * | 2023-12-07 | 2025-06-12 | The Regents Of The University Of California | Methods for making diesel fuel using catalyst-free transesterification of vegetable oils |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026329A (en) * | 1957-07-11 | 1962-03-20 | Purdue Research Foundation | Mono-and di-chloroborane etherates |
| US3070608A (en) * | 1958-07-07 | 1962-12-25 | Swift & Co | Selective alcoholysis of epoxy fatty acid esters |
| NL298688A (https=) | 1962-10-02 | |||
| US3468904A (en) | 1965-10-24 | 1969-09-23 | Hodag Chem Corp | Production of light-colored fattyderived amino-containing compounds |
| JPS5522618A (en) * | 1978-08-03 | 1980-02-18 | Nippon Oil & Fats Co Ltd | Decolorization of carboxylic ester |
| DE3613106A1 (de) * | 1986-04-18 | 1987-10-22 | Basf Ag | Verfahren zur herstellung von polytetramethylenetherglykoldiestern mit niedriger farbzahl |
| US6797753B2 (en) | 2000-06-20 | 2004-09-28 | Battelle Memorial Institute | Plasticizers derived from vegetable oils |
| US7126018B2 (en) * | 2004-01-16 | 2006-10-24 | Archer-Daniels-Midland Company | Methods for the preparation of polyol esters that are light in color |
| DE112005001607T5 (de) * | 2004-07-08 | 2007-05-24 | Archer-Daniels-Midland Co., Decatur | Epoxidierte Ester von Pflanzenöl-Fettsäuren als reaktive Verdünnungsmittel |
| CA2701044C (en) * | 2007-09-28 | 2018-02-27 | Stepan Company | Aromatic polyester polyols and aromatic polyester polyol blends containing biorenewable components and methods of making |
| JP5418494B2 (ja) * | 2008-03-04 | 2014-02-19 | 日本電気株式会社 | アシストバネ、携帯機器及び携帯機器の開閉付勢方法 |
| MX341364B (es) * | 2008-06-17 | 2016-08-18 | Resinas Y Mat S A De C V | Bioplastificantes o plastificantes oleoquimicos primarios, que a su vez actuan como estabilizadores termicos y de radiacion ultravioleta en resinas moldeables de pvc y proceso para obtencion de los mismos. |
| CN103119094B (zh) * | 2010-01-22 | 2014-07-16 | 阿彻丹尼尔斯米德兰德公司 | 制备高纯度可更新来源基增塑剂的方法和由其制备的产品 |
-
2012
- 2012-05-21 IN IN197DEN2014 patent/IN2014DN00197A/en unknown
- 2012-05-21 CA CA2840053A patent/CA2840053C/en active Active
- 2012-05-21 PT PT128043734T patent/PT2723706T/pt unknown
- 2012-05-21 BR BR112013033261A patent/BR112013033261B1/pt active IP Right Grant
- 2012-05-21 CN CN201280040179.2A patent/CN103732570B/zh active Active
- 2012-05-21 WO PCT/US2012/038760 patent/WO2013002913A1/en not_active Ceased
- 2012-05-21 US US14/125,602 patent/US9708571B2/en active Active
- 2012-05-21 EP EP12804373.4A patent/EP2723706B1/en active Active
- 2012-05-21 JP JP2014518564A patent/JP6178310B2/ja active Active
- 2012-05-21 ES ES12804373T patent/ES2784130T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9708571B2 (en) | 2017-07-18 |
| EP2723706A4 (en) | 2015-11-18 |
| CN103732570A (zh) | 2014-04-16 |
| JP2014529578A (ja) | 2014-11-13 |
| JP6178310B2 (ja) | 2017-08-09 |
| PT2723706T (pt) | 2020-04-15 |
| CA2840053A1 (en) | 2013-01-03 |
| EP2723706A1 (en) | 2014-04-30 |
| IN2014DN00197A (https=) | 2015-06-05 |
| WO2013002913A1 (en) | 2013-01-03 |
| EP2723706B1 (en) | 2020-03-11 |
| BR112013033261A2 (pt) | 2017-03-01 |
| US20140113999A1 (en) | 2014-04-24 |
| CA2840053C (en) | 2019-11-26 |
| ES2784130T3 (es) | 2020-09-22 |
| CN103732570B (zh) | 2016-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 21/05/2012, OBSERVADAS AS CONDICOES LEGAIS. |