ES2534399T3 - Procedimiento de escisión catalítica de aceites vegetales - Google Patents
Procedimiento de escisión catalítica de aceites vegetales Download PDFInfo
- Publication number
- ES2534399T3 ES2534399T3 ES08759491.7T ES08759491T ES2534399T3 ES 2534399 T3 ES2534399 T3 ES 2534399T3 ES 08759491 T ES08759491 T ES 08759491T ES 2534399 T3 ES2534399 T3 ES 2534399T3
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- Prior art keywords
- acid
- oil
- process according
- triglycerides
- catalyst
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- 238000000034 method Methods 0.000 title claims abstract description 67
- 230000008569 process Effects 0.000 title claims abstract description 48
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 13
- 239000008158 vegetable oil Substances 0.000 title claims abstract description 13
- 238000003776 cleavage reaction Methods 0.000 title description 3
- 230000007017 scission Effects 0.000 title description 3
- 230000003197 catalytic effect Effects 0.000 title description 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 40
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 22
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 22
- 150000002009 diols Chemical group 0.000 claims abstract description 21
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001301 oxygen Substances 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 239000013067 intermediate product Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000003921 oil Substances 0.000 claims description 21
- 235000019198 oils Nutrition 0.000 claims description 21
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 7
- 235000019486 Sunflower oil Nutrition 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 239000002600 sunflower oil Substances 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-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
- 239000007864 aqueous solution Substances 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 5
- 240000002791 Brassica napus Species 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical group O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004367 Lipase Substances 0.000 claims description 3
- 102000004882 Lipase Human genes 0.000 claims description 3
- 108090001060 Lipase Proteins 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 229940011182 cobalt acetate Drugs 0.000 claims description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical group [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 3
- 235000019421 lipase Nutrition 0.000 claims description 3
- 238000001256 steam distillation Methods 0.000 claims description 3
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 claims description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 claims description 2
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 2
- 244000257790 Brassica carinata Species 0.000 claims description 2
- 235000005156 Brassica carinata Nutrition 0.000 claims description 2
- 235000011293 Brassica napus Nutrition 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 235000011309 Crambe hispanica subsp abyssinica Nutrition 0.000 claims description 2
- 241000220247 Crambe hispanica subsp. abyssinica Species 0.000 claims description 2
- 241000219992 Cuphea Species 0.000 claims description 2
- 241000221089 Jatropha Species 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 241000390166 Physaria Species 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000003842 bromide salts Chemical class 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001868 cobalt Chemical class 0.000 claims description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 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 description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- SECPZKHBENQXJG-BQYQJAHWSA-N palmitelaidic acid Chemical compound CCCCCC\C=C\CCCCCCCC(O)=O SECPZKHBENQXJG-BQYQJAHWSA-N 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 241000219193 Brassicaceae Species 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LQJBNNIYVWPHFW-VAWYXSNFSA-N gadelaidic acid Chemical compound CCCCCCCCCC\C=C\CCCCCCCC(O)=O LQJBNNIYVWPHFW-VAWYXSNFSA-N 0.000 claims 1
- 150000002696 manganese Chemical class 0.000 claims 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 claims 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims 1
- -1 unsaturated fatty acid triglycerides Chemical class 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 description 9
- 238000007248 oxidative elimination reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000012190 activator Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005643 Pelargonic acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 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 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 description 1
- SMTKGALBDOEZCA-UHFFFAOYSA-N 2-tetradecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)C(O)=O SMTKGALBDOEZCA-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- UDCGYHLLBVVETC-UNTBIKODSA-N C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.OC(CC=CCCCCCCCC(=O)O)CCCCCC Chemical compound C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.OC(CC=CCCCCCCCC(=O)O)CCCCCC UDCGYHLLBVVETC-UNTBIKODSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 244000168141 Geotrichum candidum Species 0.000 description 1
- 235000017388 Geotrichum candidum Nutrition 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 241001507683 Penicillium aurantiogriseum Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000589774 Pseudomonas sp. Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 241000223258 Thermomyces lanuginosus Species 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
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
- C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/245—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of keto groups or secondary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000953A ITMI20070953A1 (it) | 2007-05-10 | 2007-05-10 | Processo di scissione catalitica di oli vegetali |
| ITMI20070953 | 2007-05-10 | ||
| PCT/EP2008/055757 WO2008138892A1 (en) | 2007-05-10 | 2008-05-09 | Process for the catalytic cleavage of vegetable oils. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2534399T3 true ES2534399T3 (es) | 2015-04-22 |
Family
ID=38724552
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08759491.7T Active ES2534399T3 (es) | 2007-05-10 | 2008-05-09 | Procedimiento de escisión catalítica de aceites vegetales |
| ES11156561T Active ES2911227T3 (es) | 2007-05-10 | 2008-05-09 | Triglicéridos que contienen ácidos carboxílicos saturados que tienen más de una función ácida |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11156561T Active ES2911227T3 (es) | 2007-05-10 | 2008-05-09 | Triglicéridos que contienen ácidos carboxílicos saturados que tienen más de una función ácida |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8222438B2 (enExample) |
| EP (2) | EP2322496B1 (enExample) |
| JP (1) | JP5318854B2 (enExample) |
| CN (1) | CN101679181B (enExample) |
| BR (1) | BRPI0810262B1 (enExample) |
| CA (1) | CA2684683C (enExample) |
| ES (2) | ES2534399T3 (enExample) |
| IT (1) | ITMI20070953A1 (enExample) |
| WO (1) | WO2008138892A1 (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8877952B2 (en) | 2005-04-26 | 2014-11-04 | Battelle Memorial Institute | Pre-esterification of primary polyols to improve solubility in solvents used in the polyol process |
| EP2331602B2 (de) | 2008-09-29 | 2017-11-01 | Basf Se | Verfahren zur beschichtung von papier |
| EP2350162B1 (de) | 2008-09-29 | 2017-11-15 | Basf Se | Aliphatische polyester |
| US8691127B2 (en) | 2008-12-19 | 2014-04-08 | Basf Se | Method for producing a composite component by multi-component injection molding |
| CA2748622C (en) * | 2008-12-31 | 2016-11-01 | Battelle Memorial Institute | Preparation of esters and polyols by initial oxidative cleavage of fatty acids followed by esterification reactions |
| MX2011006961A (es) | 2008-12-31 | 2011-09-27 | Battelle Memorial Institute | Uso de acidos grasos como material de alimentacion en el proceso de poliol. |
| FR2940801B1 (fr) * | 2009-01-06 | 2012-08-17 | Arkema France | Procede de fabrication d'un methacrylate de methyle derive de la biomasse |
| JP5448036B2 (ja) * | 2009-02-18 | 2014-03-19 | トヨタ自動車株式会社 | カルボン酸の製造方法 |
| EP2406357B1 (en) | 2009-03-13 | 2016-04-27 | Battelle Memorial Institute | Process for producing modified vegetable oil lubricants |
| WO2010115764A2 (en) * | 2009-04-06 | 2010-10-14 | Novozymes A/S | Triglycerides with high content of unsaturated fatty acids |
| IT1397379B1 (it) * | 2009-12-30 | 2013-01-10 | Novamont Spa | Processo continuo per la produzione di derivati di acidi carbossilici saturi |
| IT1397378B1 (it) | 2009-12-30 | 2013-01-10 | Novamont Spa | Processo continuo di scissione ossidativa di oli vegetali |
| IT1403273B1 (it) | 2010-12-20 | 2013-10-17 | Novamont Spa | Derivati di oli vegetali come oli estensori per composizioni elastomeriche |
| IT1403272B1 (it) | 2010-12-20 | 2013-10-17 | Novamont Spa | Strutture oligomeriche complesse |
| FR2983477B1 (fr) | 2011-12-01 | 2013-12-27 | Arkema France | Procede de coupure de chaines grasses insaturees |
| ITNO20120002A1 (it) | 2012-03-20 | 2013-09-21 | Novamont Spa | Processo per la produzione di composti organici a partire da specie vegetali |
| ITMI20121067A1 (it) | 2012-06-19 | 2013-12-20 | Novamont Spa | Derivati vegetali come oli estensori e biofiller in composizioni elastomeriche. |
| ITMI20121070A1 (it) | 2012-06-19 | 2013-12-20 | Novamont Spa | Processo di preparazione di strutture oligomeriche complesse |
| FR2994178B1 (fr) | 2012-07-31 | 2015-08-07 | Interoleagineuse D Assistance Et De Dev S I A Soc | Procede de preparation d'un acide carboxylique ou d'un aldehyde |
| ITNO20130005A1 (it) * | 2013-06-27 | 2014-12-28 | Novamont Spa | Processo per l'idrogenazione selettiva di oli vegetali |
| JP6653653B2 (ja) | 2014-01-13 | 2020-02-26 | ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ | 脂肪族エステルおよびそれらを含むポリマー組成物 |
| WO2015135929A1 (en) | 2014-03-11 | 2015-09-17 | Novamont S.P.A. | Process for the synthesis of aliphatic dialkyl esters from vegetable oils |
| WO2015135936A1 (en) | 2014-03-11 | 2015-09-17 | Novamont S.P.A. | New process for the preparation of complex oligomeric structures |
| CN107207625A (zh) | 2014-12-19 | 2017-09-26 | 诺瓦蒙特股份公司 | 变性淀粉衍生物作为弹性体组合物用滞后降低添加剂的用途 |
| CN107108760B (zh) | 2014-12-19 | 2021-05-11 | 诺瓦蒙特股份公司 | 变性淀粉衍生物和含有它们的弹性体组合物 |
| WO2016102509A1 (en) | 2014-12-22 | 2016-06-30 | Novamont S.P.A. | Improved process for the selective hydrogenation of vegetable oils |
| EP3444032B1 (en) | 2015-01-22 | 2024-12-18 | Novamont S.p.A. | Process for the recovery of cobalt and tungstic acid and/or its derivatives from aqueous solutions |
| PL3253804T3 (pl) | 2015-02-05 | 2022-04-19 | Novamont S.P.A. | Sposób uprawy roślin wieloletnich należących do szczepu cardueae oraz zintegrowanego odzyskiwania inuliny, nasion i biomasy ze wspomnianych roślin |
| ES2751551T3 (es) | 2015-06-12 | 2020-04-01 | Novamont Spa | Esteres de trimetilolpropano de bajo punto de fluidez |
| ITUB20153460A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Composizioni cosmetiche acquose contenenti esteri dell?acido pelargonico |
| ITUB20153461A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Composizioni cosmetiche lipofile contenenti esteri dell?acido pelargonico |
| ITUB20153490A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Miscele di esteri dell?acido pelargonico |
| ITUB20160866A1 (it) | 2016-02-18 | 2017-08-18 | Versalis Spa | Inibitore di corrosione comprendente strutture oligomeriche complesse derivanti da oli vegetali |
| ITUA20163227A1 (it) | 2016-05-06 | 2017-11-06 | Novamont Spa | Composizioni cosmetiche contenenti diglicerolo tetrapelargonato. |
| ITUA20163758A1 (it) | 2016-05-24 | 2017-11-24 | Catalisi Innovativa Per Il Riciclo Del Carbonio E Biopolimeri Srl | Ossidi misti polifunzionali per la scissione ossidativa di lipidi e di metil esteri di acidi grassi insaturi |
| ITUA20164118A1 (it) * | 2016-06-06 | 2017-12-06 | Novamont Spa | Processo di preparazione di acidi dicarbossilici purificati. |
| ITUA20164110A1 (it) | 2016-06-06 | 2017-12-06 | Novamont Spa | Processo di scissione ossidativa di dioli vicinali. |
| ITUA20164114A1 (it) | 2016-06-06 | 2017-12-06 | Novamont Spa | Processo migliorato di idrolisi di trigliceridi di acidi dicarbossilici. |
| ITUA20164552A1 (it) | 2016-06-21 | 2017-12-21 | Novamont Spa | Processo per l’idrogenazione selettiva di oli vegetali con catalizzatori tipo egg-shell. |
| US11453634B2 (en) | 2017-11-22 | 2022-09-27 | Novamont S.P.A. | Production of carboxylic acids from vicinal diols |
| CN112812001A (zh) * | 2020-12-29 | 2021-05-18 | 江南大学 | 一种9,10-二羟基硬脂酸的制备方法 |
| IT202100006410A1 (it) | 2021-03-17 | 2022-09-17 | Novamont Spa | Recupero di acidi dicarbossilici da trigliceridi |
| EP4355723A1 (en) | 2021-06-18 | 2024-04-24 | Evonik Operations GmbH | Nonanic acid esters |
| CN113683482B (zh) * | 2021-09-02 | 2023-12-01 | 禾大西普化学（四川）有限公司 | 一种山嵛酸和硬脂酸的制备方法 |
| KR102837560B1 (ko) * | 2024-10-28 | 2025-07-23 | 케이지케미칼 주식회사 | 천연 펠라르곤산을 포함하는 잡초 생장 억제용 조성물. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB348593A (en) * | 1929-03-02 | 1931-05-14 | Deutsche Gasgluehlicht Auer | Process for the manufacture of plastic substances |
| GB604281A (en) | 1944-01-20 | 1948-07-01 | Emery Industries Inc | Improvements in or relating to methods of oxidizing relatively long chain unsaturated fatty bodies |
| FR1421431A (fr) * | 1963-10-29 | 1965-12-17 | Procter & Gamble | Nouveaux dérivés de mono- et di-acylglycérols et leur utilisation |
| BE654490A (enExample) | 1963-10-29 | 1965-04-16 | ||
| BE787910A (fr) * | 1971-08-23 | 1973-02-23 | Unilever Emery | Compositions cireuses |
| EP0128484B1 (en) | 1983-06-02 | 1988-01-20 | New Japan Chemical Co.,Ltd. | Process for preparing carboxylic acid |
| US20040034091A1 (en) * | 1991-01-29 | 2004-02-19 | Sigma Tau Industrie Farmaceutiche Riunite S.P.A. | Derivative of dicarboxylic acids having six to twelve carbon atoms and use of these derivatives and dicarboxylic acids alone in the preparation of pharmaceutical compositions for enteral and parenteral nutrition |
| IT1244645B (it) | 1991-01-29 | 1994-08-08 | Marco Castagneto | Derivati degli acidi dicarbossilici aventi da sei a dodici atomi di carbonio ed impiego di tali derivati e degli acidi stessi per la preparazione di composizioni farmaceutiche atte all'alimentazione enterale parenterale. |
| IT1251708B (it) * | 1991-12-11 | 1995-05-20 | Novamont Spa | Procedimento per la preparazione di acidi carbossilici o loro esteri mediante scissione ossidativa di acidi grassi insaturi o loro esteri. |
| IT1256989B (it) * | 1992-10-29 | 1995-12-27 | Novamont Spa | Procedimento per la preparazione di acidi carbossilici o loro esteri mediante scissione ossidativa di acidi grassi insaturi o loro esteri. |
| US5380928A (en) * | 1993-08-18 | 1995-01-10 | Synergistics Industries, Inc. | Two step oxidation process for the production of carboxylic acids such as azelaic acid from unsaturated substrates |
| FR2724651B1 (fr) * | 1994-09-16 | 1996-12-20 | Rhone Poulenc Chimie | Procede de preparation d'acides mono-et dicarboxyliques a partir d'acides gras insatures et/ou leurs derives |
| JP2000204060A (ja) * | 1999-01-12 | 2000-07-25 | Nisshin Oil Mills Ltd:The | エステル化生成物および化粧料 |
| ITMI20051779A1 (it) | 2005-09-23 | 2007-03-24 | Novamont Spa | Processo migliorato per la produzione di derivati di acidi carbossilici saturi |
-
2007
- 2007-05-10 IT IT000953A patent/ITMI20070953A1/it unknown
-
2008
- 2008-05-09 EP EP11156561.0A patent/EP2322496B1/en active Active
- 2008-05-09 US US12/599,459 patent/US8222438B2/en active Active
- 2008-05-09 BR BRPI0810262-7A patent/BRPI0810262B1/pt active IP Right Grant
- 2008-05-09 CN CN200880015457.2A patent/CN101679181B/zh active Active
- 2008-05-09 ES ES08759491.7T patent/ES2534399T3/es active Active
- 2008-05-09 WO PCT/EP2008/055757 patent/WO2008138892A1/en not_active Ceased
- 2008-05-09 EP EP08759491.7A patent/EP2155646B1/en active Active
- 2008-05-09 ES ES11156561T patent/ES2911227T3/es active Active
- 2008-05-09 JP JP2010506949A patent/JP5318854B2/ja active Active
- 2008-05-09 CA CA2684683A patent/CA2684683C/en active Active
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2012
- 2012-05-16 US US13/472,976 patent/US8629290B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20100311995A1 (en) | 2010-12-09 |
| EP2155646B1 (en) | 2015-01-14 |
| ITMI20070953A1 (it) | 2008-11-11 |
| EP2322496B1 (en) | 2022-03-30 |
| EP2322496A1 (en) | 2011-05-18 |
| WO2008138892A1 (en) | 2008-11-20 |
| EP2155646A1 (en) | 2010-02-24 |
| US8222438B2 (en) | 2012-07-17 |
| BRPI0810262A2 (pt) | 2014-11-04 |
| CA2684683C (en) | 2015-04-28 |
| US20120226060A1 (en) | 2012-09-06 |
| BRPI0810262B1 (pt) | 2018-01-30 |
| JP2010526796A (ja) | 2010-08-05 |
| CN101679181A (zh) | 2010-03-24 |
| US8629290B2 (en) | 2014-01-14 |
| ES2911227T3 (es) | 2022-05-18 |
| CN101679181B (zh) | 2016-06-15 |
| CA2684683A1 (en) | 2008-11-20 |
| JP5318854B2 (ja) | 2013-10-16 |
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