ITMI20070953A1 - Processo di scissione catalitica di oli vegetali - Google Patents
Processo di scissione catalitica di oli vegetali Download PDFInfo
- Publication number
- ITMI20070953A1 ITMI20070953A1 IT000953A ITMI20070953A ITMI20070953A1 IT MI20070953 A1 ITMI20070953 A1 IT MI20070953A1 IT 000953 A IT000953 A IT 000953A IT MI20070953 A ITMI20070953 A IT MI20070953A IT MI20070953 A1 ITMI20070953 A1 IT MI20070953A1
- Authority
- IT
- Italy
- Prior art keywords
- process according
- cobalt
- acid
- oil
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 70
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims description 11
- 239000008158 vegetable oil Substances 0.000 title claims description 11
- 230000003197 catalytic effect Effects 0.000 title description 2
- 238000010504 bond cleavage reaction Methods 0.000 title 1
- 230000007017 scission Effects 0.000 title 1
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 150000001735 carboxylic acids Chemical class 0.000 claims description 30
- 150000003626 triacylglycerols Chemical class 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000002009 diols Chemical group 0.000 claims description 17
- 239000012071 phase Substances 0.000 claims description 17
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 13
- 235000019198 oils Nutrition 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 9
- 235000019486 Sunflower oil Nutrition 0.000 claims description 7
- 229940011182 cobalt acetate Drugs 0.000 claims description 7
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000002600 sunflower oil Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 150000001868 cobalt Chemical class 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 4
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 4
- 229910001981 cobalt nitrate Inorganic materials 0.000 claims description 4
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 claims description 4
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000243 solution Substances 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
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 241000219992 Cuphea Species 0.000 claims description 2
- 241000221089 Jatropha Species 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 150000001447 alkali 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
- 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
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000002540 palm oil Substances 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
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 239000000543 intermediate Substances 0.000 description 8
- 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
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000005643 Pelargonic acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 1
- 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
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 1
- -1 cobalt salts Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
Landscapes
- 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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000953A ITMI20070953A1 (it) | 2007-05-10 | 2007-05-10 | Processo di scissione catalitica di oli vegetali |
| PCT/EP2008/055757 WO2008138892A1 (en) | 2007-05-10 | 2008-05-09 | Process for the catalytic cleavage of vegetable oils. |
| CA2684683A CA2684683C (en) | 2007-05-10 | 2008-05-09 | Process for the catalytic cleavage of vegetable oils |
| ES08759491.7T ES2534399T3 (es) | 2007-05-10 | 2008-05-09 | Procedimiento de escisión catalítica de aceites vegetales |
| US12/599,459 US8222438B2 (en) | 2007-05-10 | 2008-05-09 | Process for the catalytic cleavage of vegetable oils |
| BRPI0810262-7A BRPI0810262B1 (pt) | 2007-05-10 | 2008-05-09 | Processo para a clivagem catalítica de óleos vegetais. |
| CN200880015457.2A CN101679181B (zh) | 2007-05-10 | 2008-05-09 | 植物油的催化裂解法 |
| JP2010506949A JP5318854B2 (ja) | 2007-05-10 | 2008-05-09 | 植物油の触媒開裂方法 |
| EP11156561.0A EP2322496B1 (en) | 2007-05-10 | 2008-05-09 | Triglycerides containing saturated carboxylic acids having more than one acid function |
| EP08759491.7A EP2155646B1 (en) | 2007-05-10 | 2008-05-09 | Process for the catalytic cleavage of vegetable oils. |
| ES11156561T ES2911227T3 (es) | 2007-05-10 | 2008-05-09 | Triglicéridos que contienen ácidos carboxílicos saturados que tienen más de una función ácida |
| US13/472,976 US8629290B2 (en) | 2007-05-10 | 2012-05-16 | Trigycerides containing certain saturated carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000953A ITMI20070953A1 (it) | 2007-05-10 | 2007-05-10 | Processo di scissione catalitica di oli vegetali |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ITMI20070953A1 true ITMI20070953A1 (it) | 2008-11-11 |
Family
ID=38724552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT000953A ITMI20070953A1 (it) | 2007-05-10 | 2007-05-10 | Processo di scissione catalitica di oli vegetali |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8222438B2 (https=) |
| EP (2) | EP2155646B1 (https=) |
| JP (1) | JP5318854B2 (https=) |
| CN (1) | CN101679181B (https=) |
| BR (1) | BRPI0810262B1 (https=) |
| CA (1) | CA2684683C (https=) |
| ES (2) | ES2911227T3 (https=) |
| IT (1) | ITMI20070953A1 (https=) |
| WO (1) | WO2008138892A1 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8859794B2 (en) | 2005-04-26 | 2014-10-14 | Battelle Memorial Institute | Use of fatty acids as feed material in polyol process |
| US9744556B2 (en) | 2008-09-29 | 2017-08-29 | Basf Se | Method for coating paper |
| US20110313075A1 (en) | 2008-09-29 | 2011-12-22 | Basf Se | Aliphatic polyester |
| EP2379301B1 (de) | 2008-12-19 | 2013-02-20 | Basf Se | Verfahren zur herstellung eines verbundbauteils durch mehrkomponentenspritzguss, solcher verbundbauteil und verwendung einer mischung zur herstellung des verbundbauteils |
| MX2011007002A (es) | 2008-12-31 | 2012-09-28 | Battelle Memorial Institute | Pre-esterificacion de polioles primarios para mejorar la solubilidad en solventes usados en el proceso de poliol. |
| JP6075952B2 (ja) * | 2008-12-31 | 2017-02-08 | バテル・メモリアル・インスティテュートＢａｔｔｅｌｌｅ Ｍｅｍｏｒｉａｌ Ｉｎｓｔｉｔｕｔｅ | 最初の脂肪酸の酸化的開裂と次のエステル化反応によるエステルとポリオールの製造 |
| 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 |
| JP2012520377A (ja) | 2009-03-13 | 2012-09-06 | バテル・メモリアル・インスティテュート | 変性植物油潤滑剤 |
| BRPI1013321A2 (pt) * | 2009-04-06 | 2015-09-01 | Novozymes As | Processos para produzir um produto de triglicerídeos, e, uso da fração de alquil ésteres de ácidos graxos saturados |
| IT1397378B1 (it) | 2009-12-30 | 2013-01-10 | Novamont Spa | Processo continuo di scissione ossidativa di oli vegetali |
| IT1397379B1 (it) * | 2009-12-30 | 2013-01-10 | Novamont Spa | Processo continuo per la produzione di derivati di acidi carbossilici saturi |
| 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 |
| ITMI20121070A1 (it) | 2012-06-19 | 2013-12-20 | Novamont Spa | Processo di preparazione di strutture oligomeriche complesse |
| ITMI20121067A1 (it) | 2012-06-19 | 2013-12-20 | Novamont Spa | Derivati vegetali come oli estensori e biofiller in composizioni elastomeriche. |
| 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 |
| US9695105B2 (en) | 2014-03-11 | 2017-07-04 | Novamont S.P.A. | Process for the preparation of complex oligomeric structures |
| TR201901558T4 (tr) * | 2014-03-11 | 2019-02-21 | Novamont Spa | Bitkisel yağlardan alifatik dialkil esterlerin sentezine yönelik proses. |
| JP2018503718A (ja) | 2014-12-19 | 2018-02-08 | ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ | エラストマ組成物用のヒステリシス減少添加剤としての破壊澱粉誘導体の使用 |
| WO2016097151A1 (en) | 2014-12-19 | 2016-06-23 | Novamont S.P.A. | Destructured starch derivatives and elastomer compositions containing them |
| WO2016102509A1 (en) | 2014-12-22 | 2016-06-30 | Novamont S.P.A. | Improved process for the selective hydrogenation of vegetable oils |
| EP3247495B1 (en) * | 2015-01-22 | 2018-10-24 | Novamont S.p.A. | Process for the recovery of cobalt and tungstic acid and/or their 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 |
| WO2016198668A1 (en) | 2015-06-12 | 2016-12-15 | Novamont S.P.A. | Low pour point trimethylolpropane esters. |
| ITUB20153490A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Miscele di esteri dell?acido pelargonico |
| ITUB20153461A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Composizioni cosmetiche lipofile contenenti esteri dell?acido pelargonico |
| ITUB20153460A1 (it) | 2015-09-08 | 2017-03-08 | Novamont Spa | Composizioni cosmetiche acquose contenenti 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. |
| ES2949972T3 (es) | 2017-11-22 | 2023-10-04 | Novamont Spa | Producción de ácidos carboxílicos a partir de dioles vecinales |
| 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 |
| WO2022263149A1 (en) | 2021-06-18 | 2022-12-22 | 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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| 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 |
| BE654490A (https=) * | 1963-10-29 | 1965-04-16 | ||
| FR1421431A (fr) * | 1963-10-29 | 1965-12-17 | Procter & Gamble | Nouveaux dérivés de mono- et di-acylglycérols et leur utilisation |
| BE787910A (fr) * | 1971-08-23 | 1973-02-23 | Unilever Emery | Compositions cireuses |
| DE3468861D1 (en) * | 1983-06-02 | 1988-02-25 | New Japan Chem Co Ltd | Process for preparing carboxylic acid |
| 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. |
| 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 |
| 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
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2008
- 2008-05-09 EP EP08759491.7A patent/EP2155646B1/en active Active
- 2008-05-09 EP EP11156561.0A patent/EP2322496B1/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 US US12/599,459 patent/US8222438B2/en active Active
- 2008-05-09 CA CA2684683A patent/CA2684683C/en active Active
- 2008-05-09 CN CN200880015457.2A patent/CN101679181B/zh active Active
- 2008-05-09 BR BRPI0810262-7A patent/BRPI0810262B1/pt active IP Right Grant
- 2008-05-09 WO PCT/EP2008/055757 patent/WO2008138892A1/en not_active Ceased
- 2008-05-09 ES ES08759491.7T patent/ES2534399T3/es active Active
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2012
- 2012-05-16 US US13/472,976 patent/US8629290B2/en active Active
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| Publication number | Publication date |
|---|---|
| BRPI0810262B1 (pt) | 2018-01-30 |
| CN101679181B (zh) | 2016-06-15 |
| CA2684683C (en) | 2015-04-28 |
| EP2322496A1 (en) | 2011-05-18 |
| EP2155646B1 (en) | 2015-01-14 |
| JP2010526796A (ja) | 2010-08-05 |
| CA2684683A1 (en) | 2008-11-20 |
| EP2155646A1 (en) | 2010-02-24 |
| US20100311995A1 (en) | 2010-12-09 |
| CN101679181A (zh) | 2010-03-24 |
| BRPI0810262A2 (pt) | 2014-11-04 |
| US20120226060A1 (en) | 2012-09-06 |
| US8629290B2 (en) | 2014-01-14 |
| ES2911227T3 (es) | 2022-05-18 |
| WO2008138892A1 (en) | 2008-11-20 |
| ES2534399T3 (es) | 2015-04-22 |
| EP2322496B1 (en) | 2022-03-30 |
| JP5318854B2 (ja) | 2013-10-16 |
| US8222438B2 (en) | 2012-07-17 |
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