RU2012104507A - Способ получения полиолов на основе возобновляемого исходного сырья - Google Patents
Способ получения полиолов на основе возобновляемого исходного сырья Download PDFInfo
- Publication number
- RU2012104507A RU2012104507A RU2012104507/04A RU2012104507A RU2012104507A RU 2012104507 A RU2012104507 A RU 2012104507A RU 2012104507/04 A RU2012104507/04 A RU 2012104507/04A RU 2012104507 A RU2012104507 A RU 2012104507A RU 2012104507 A RU2012104507 A RU 2012104507A
- Authority
- RU
- Russia
- Prior art keywords
- oil
- acid
- stage
- esters
- carried out
- Prior art date
Links
- 229920005862 polyol Polymers 0.000 title claims abstract 6
- 150000003077 polyols Chemical class 0.000 title claims abstract 6
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000002994 raw material Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract 8
- 229930195729 fatty acid Natural products 0.000 claims abstract 8
- 239000000194 fatty acid Substances 0.000 claims abstract 8
- 239000003925 fat Substances 0.000 claims abstract 6
- 235000019197 fats Nutrition 0.000 claims abstract 6
- 150000004665 fatty acids Chemical class 0.000 claims abstract 6
- 239000003921 oil Substances 0.000 claims abstract 6
- 235000019198 oils Nutrition 0.000 claims abstract 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims abstract 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims abstract 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims abstract 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims abstract 3
- 235000019482 Palm oil Nutrition 0.000 claims abstract 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims abstract 3
- 235000019486 Sunflower oil Nutrition 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 3
- -1 fatty acid esters Chemical class 0.000 claims abstract 3
- 230000003993 interaction Effects 0.000 claims abstract 3
- 239000002540 palm oil Substances 0.000 claims abstract 3
- 235000012424 soybean oil Nutrition 0.000 claims abstract 3
- 239000003549 soybean oil Substances 0.000 claims abstract 3
- 239000002600 sunflower oil Substances 0.000 claims abstract 3
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 claims abstract 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 claims abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract 2
- PIFPCDRPHCQLSJ-WYIJOVFWSA-N 4,8,12,15,19-Docosapentaenoic acid Chemical compound CC\C=C\CC\C=C\C\C=C\CC\C=C\CC\C=C\CCC(O)=O PIFPCDRPHCQLSJ-WYIJOVFWSA-N 0.000 claims abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract 2
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims abstract 2
- 235000019489 Almond oil Nutrition 0.000 claims abstract 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims abstract 2
- PIFPCDRPHCQLSJ-UHFFFAOYSA-N Clupanodonic acid Natural products CCC=CCCC=CCC=CCCC=CCCC=CCCC(O)=O PIFPCDRPHCQLSJ-UHFFFAOYSA-N 0.000 claims abstract 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims abstract 2
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 claims abstract 2
- 235000019487 Hazelnut oil Nutrition 0.000 claims abstract 2
- 240000000950 Hippophae rhamnoides Species 0.000 claims abstract 2
- 235000003145 Hippophae rhamnoides Nutrition 0.000 claims abstract 2
- 235000018330 Macadamia integrifolia Nutrition 0.000 claims abstract 2
- 235000003800 Macadamia tetraphylla Nutrition 0.000 claims abstract 2
- 240000000912 Macadamia tetraphylla Species 0.000 claims abstract 2
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 claims abstract 2
- 240000008338 Nigella arvensis Species 0.000 claims abstract 2
- 235000007413 Nigella arvensis Nutrition 0.000 claims abstract 2
- 235000016698 Nigella sativa Nutrition 0.000 claims abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000005642 Oleic acid Substances 0.000 claims abstract 2
- 235000021319 Palmitoleic acid Nutrition 0.000 claims abstract 2
- 235000019483 Peanut oil Nutrition 0.000 claims abstract 2
- 235000019497 Pistachio oil Nutrition 0.000 claims abstract 2
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 claims abstract 2
- 235000021322 Vaccenic acid Nutrition 0.000 claims abstract 2
- 235000019498 Walnut oil Nutrition 0.000 claims abstract 2
- 239000008168 almond oil Substances 0.000 claims abstract 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims abstract 2
- 235000021342 arachidonic acid Nutrition 0.000 claims abstract 2
- 229940114079 arachidonic acid Drugs 0.000 claims abstract 2
- 235000021302 avocado oil Nutrition 0.000 claims abstract 2
- 239000008163 avocado oil Substances 0.000 claims abstract 2
- 235000021324 borage oil Nutrition 0.000 claims abstract 2
- 239000010474 borage seed oil Substances 0.000 claims abstract 2
- 239000004359 castor oil Substances 0.000 claims abstract 2
- 235000019438 castor oil Nutrition 0.000 claims abstract 2
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims abstract 2
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 claims abstract 2
- 235000019864 coconut oil Nutrition 0.000 claims abstract 2
- 239000003240 coconut oil Substances 0.000 claims abstract 2
- 235000005687 corn oil Nutrition 0.000 claims abstract 2
- 239000002285 corn oil Substances 0.000 claims abstract 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims abstract 2
- 229940090949 docosahexaenoic acid Drugs 0.000 claims abstract 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims abstract 2
- 235000021323 fish oil Nutrition 0.000 claims abstract 2
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 claims abstract 2
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims abstract 2
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims abstract 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 abstract 2
- 239000008169 grapeseed oil Substances 0.000 claims abstract 2
- 239000010468 hazelnut oil Substances 0.000 claims abstract 2
- 239000010460 hemp oil Substances 0.000 claims abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract 2
- 235000021388 linseed oil Nutrition 0.000 claims abstract 2
- 239000000944 linseed oil Substances 0.000 claims abstract 2
- 235000021290 n-3 DPA Nutrition 0.000 claims abstract 2
- 239000010466 nut oil Substances 0.000 claims abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract 2
- 235000021313 oleic acid Nutrition 0.000 claims abstract 2
- 235000008390 olive oil Nutrition 0.000 claims abstract 2
- 239000004006 olive oil Substances 0.000 claims abstract 2
- 239000000312 peanut oil Substances 0.000 claims abstract 2
- 239000010471 pistachio oil Substances 0.000 claims abstract 2
- 229940082415 pistachio oil Drugs 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims abstract 2
- 239000001944 prunus armeniaca kernel oil Substances 0.000 claims abstract 2
- 239000008171 pumpkin seed oil Substances 0.000 claims abstract 2
- 239000010667 rosehip oil Substances 0.000 claims abstract 2
- 239000003813 safflower oil Substances 0.000 claims abstract 2
- 235000005713 safflower oil Nutrition 0.000 claims abstract 2
- 239000008159 sesame oil Substances 0.000 claims abstract 2
- 235000011803 sesame oil Nutrition 0.000 claims abstract 2
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003784 tall oil Substances 0.000 claims abstract 2
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 claims abstract 2
- 235000021081 unsaturated fats Nutrition 0.000 claims abstract 2
- 239000008170 walnut oil Substances 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 235000008524 evening primrose extract Nutrition 0.000 claims 1
- 239000010475 evening primrose oil Substances 0.000 claims 1
- 229940089020 evening primrose oil Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 235000013842 nitrous oxide Nutrition 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 239000010497 wheat germ oil Substances 0.000 claims 1
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 abstract 2
- OXEDXHIBHVMDST-UHFFFAOYSA-N 12Z-octadecenoic acid Natural products CCCCCC=CCCCCCCCCCCC(O)=O OXEDXHIBHVMDST-UHFFFAOYSA-N 0.000 abstract 1
- 241000219925 Oenothera Species 0.000 abstract 1
- 235000004496 Oenothera biennis Nutrition 0.000 abstract 1
- CNVZJPUDSLNTQU-UHFFFAOYSA-N Petroselaidic acid Natural products CCCCCCCCCCCC=CCCCCC(O)=O CNVZJPUDSLNTQU-UHFFFAOYSA-N 0.000 abstract 1
- 235000021307 Triticum Nutrition 0.000 abstract 1
- 244000098338 Triticum aestivum Species 0.000 abstract 1
- 229960001730 nitrous oxide Drugs 0.000 abstract 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2410/00—Soles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Abstract
1. Способ получения полиолов, включающий стадииa) взаимодействия ненасыщенных природных жиров, ненасыщенных природных жирных кислот и/или сложных эфиров жирных кислот с оксидом диазота,b) взаимодействия продукта, полученного на стадии а), с гидрирующим реагентом,c) взаимодействия продукта реакции из стадии b) с алкиленоксидами.2. Способ по п.1, отличающийся тем, что природные ненасыщенные жиры, а также производные жиров выбираются из группы, включающей в себя касторовое масло, масло из виноградных косточек, масло нигеллы, масло из тыквенных семечек, масло семян огуречника, соевое масло, масло из зародышей пшеницы, рапсовое масло, подсолнечное масло, масло из земляного ореха, масло из косточек абрикоса, фисташковое масло, миндальное масло, оливковое масло, масло ореха макадамии, масло авокадо, облепиховое масло, кунжутное масло, конопляное масло, масло из лесных орехов, масло примулы вечерней, масло шиповника, масло из семян сафлора, масло из грецкого ореха, пальмовое масло, рыбий жир, масло кокосового ореха, талловое масло, кукурузное масло, льняное масло.3. Способ по п.1, отличающийся тем, что жирные кислоты и сложные эфиры жирных кислот выбираются из группы, содержащей миристолеиновую кислоту, пальмитолеиновую кислоту, олеиновую кислоту, вакценовую кислоту, петрозелиновую кислоту, гадолеиновую кислоту, эруковую кислоту, нервоновую кислоту, линолевую кислоту, α- и γ-линоленовые кислоты, стеаридоновую кислоту, арахидоновую кислоту, тимнодоновую кислоту, клупанодоновую кислоту и цервоновую кислоту, а также их сложные эфиры.4. Способ по п.1, отличающийся тем, что ненасыщенные природные жиры выбираются из группы, содержащ�
Claims (17)
1. Способ получения полиолов, включающий стадии
a) взаимодействия ненасыщенных природных жиров, ненасыщенных природных жирных кислот и/или сложных эфиров жирных кислот с оксидом диазота,
b) взаимодействия продукта, полученного на стадии а), с гидрирующим реагентом,
c) взаимодействия продукта реакции из стадии b) с алкиленоксидами.
2. Способ по п.1, отличающийся тем, что природные ненасыщенные жиры, а также производные жиров выбираются из группы, включающей в себя касторовое масло, масло из виноградных косточек, масло нигеллы, масло из тыквенных семечек, масло семян огуречника, соевое масло, масло из зародышей пшеницы, рапсовое масло, подсолнечное масло, масло из земляного ореха, масло из косточек абрикоса, фисташковое масло, миндальное масло, оливковое масло, масло ореха макадамии, масло авокадо, облепиховое масло, кунжутное масло, конопляное масло, масло из лесных орехов, масло примулы вечерней, масло шиповника, масло из семян сафлора, масло из грецкого ореха, пальмовое масло, рыбий жир, масло кокосового ореха, талловое масло, кукурузное масло, льняное масло.
3. Способ по п.1, отличающийся тем, что жирные кислоты и сложные эфиры жирных кислот выбираются из группы, содержащей миристолеиновую кислоту, пальмитолеиновую кислоту, олеиновую кислоту, вакценовую кислоту, петрозелиновую кислоту, гадолеиновую кислоту, эруковую кислоту, нервоновую кислоту, линолевую кислоту, α- и γ-линоленовые кислоты, стеаридоновую кислоту, арахидоновую кислоту, тимнодоновую кислоту, клупанодоновую кислоту и цервоновую кислоту, а также их сложные эфиры.
4. Способ по п.1, отличающийся тем, что ненасыщенные природные жиры выбираются из группы, содержащей соевое масло, пальмовое масло, подсолнечное масло и рапсовое масло.
5. Способ по п.1, отличающийся тем, что на стадии а) веселящий газ используется в смеси с инертными газами.
6. Способ по п.1, отличающийся тем, что гидрирующий реагент представляет собой комплексный гидрид металла.
7. Способ по п.1, отличающийся тем, что гидрирующий реагент представляет собой алюмогидрид лития, или боргидрид натрия, или боргидрид лития.
8. Способ по п.1, отличающийся тем, что гидрирующий реагент представляет собой водород.
9. Способ по п.8, отличающийся тем, что стадия b) проводится в присутствии катализатора.
10. Способ по п.8, отличающийся тем, что стадия b) проводится в присутствии катализатора, который содержит по меньшей мере один переходный металл из групп с 6 по 11.
11. Способ по п.8, отличающийся тем, что стадия b) проводится в присутствии катализатора, содержащего рутений.
12. Способ по п.8, отличающийся тем, что стадия b) проводится в присутствии катализатора, содержащего никель.
13. Способ по п.1, отличающийся тем, что присоединение алкиленоксидов на стадии с) проводится в присутствии катализатора.
14. Способ по п.1, отличающийся тем, что присоединение алкиленоксидов на стадии с) проводится в присутствии мультиметаллцианидного катализатора.
15. Полиолы, полученные по одному из пп.1-14.
16. Применение полиолов по п.15 для получения полиуретанов.
17. Способ получения полиуретанов при помощи взаимодействия полиизоцианатов с соединениями, имеющими два атома водорода, реакционноспособных по отношению к изоцианатным группам, отличающийся тем, что в качестве соединений, имеющих по меньшей мере два атома водорода, реакционноспособных по отношению к изоцианатным группам, используются полиолы по п.15.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09165148 | 2009-07-10 | ||
| EP09165148.9 | 2009-07-10 | ||
| PCT/EP2010/059883 WO2011004004A1 (de) | 2009-07-10 | 2010-07-09 | Verfahren zur herstellung von polyolen auf basis nachwachsender rohstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012104507A true RU2012104507A (ru) | 2013-08-20 |
| RU2510798C2 RU2510798C2 (ru) | 2014-04-10 |
Family
ID=42575744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012104507/04A RU2510798C2 (ru) | 2009-07-10 | 2010-07-09 | Способ получения полиолов на основе возобновляемого исходного сырья |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20120108780A1 (ru) |
| EP (1) | EP2451857B1 (ru) |
| JP (1) | JP5570595B2 (ru) |
| KR (1) | KR101425734B1 (ru) |
| CN (1) | CN102498145B (ru) |
| BR (1) | BR112012000634A2 (ru) |
| ES (1) | ES2408124T3 (ru) |
| MX (1) | MX2012000420A (ru) |
| MY (1) | MY157695A (ru) |
| RU (1) | RU2510798C2 (ru) |
| SG (2) | SG10201404567VA (ru) |
| WO (1) | WO2011004004A1 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110218259A1 (en) * | 2010-03-02 | 2011-09-08 | Basf Se | Preparing polyurethanes |
| DE102014212602A1 (de) | 2013-07-02 | 2015-01-08 | Basf Se | Verfahren zur Herstellung eines Ketons aus einem Olefin |
| CN103396523B (zh) * | 2013-07-15 | 2016-02-24 | 山东晨光节能产品研发有限公司 | 太阳能热水器水箱聚醚多元醇泡沫有机防火保温材料 |
| CN105801839A (zh) * | 2015-11-30 | 2016-07-27 | 单成敏 | 一种腰果酚改性阻燃聚醚多元醇制备方法 |
| KR101842670B1 (ko) * | 2016-05-23 | 2018-03-27 | 미쓰이케미칼앤드에스케이씨폴리우레탄 주식회사 | 폴리우레탄의 제조를 위한 바이오 기반의 폴리올 |
| EP4053111A1 (en) | 2021-03-01 | 2022-09-07 | Komagra Spólka Z O.O. | The method of producing epoxidised rapeseed oil and method of producing biopolyol using epoxidised rapeseed oil |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU681038A1 (ru) * | 1976-09-30 | 1979-08-25 | Предприятие П/Я Р-6913 | Способ получени спиртов |
| GB9302418D0 (en) * | 1993-02-08 | 1993-03-24 | Ici Plc | Novel di-and polyamino compounds for use in the preparation of polyurethanes |
| US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
| US5689012A (en) | 1996-07-18 | 1997-11-18 | Arco Chemical Technology, L.P. | Continuous preparation of low unsaturation polyoxyalkylene polyether polyols with continuous additon of starter |
| DE19709031A1 (de) | 1997-03-06 | 1998-09-10 | Basf Ag | Verfahren zur Herstellung von Doppelmetallcyanidkatalysatoren |
| US5844070A (en) | 1997-05-16 | 1998-12-01 | Arco Chemical Technology, L.P. | Process for rapid activation of double metal cyanide catalysts |
| DE19844325A1 (de) * | 1998-09-28 | 2000-03-30 | Degussa | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Aldehyden oder Ketonen |
| DE19909214A1 (de) * | 1999-03-03 | 2000-09-07 | Basf Ag | Wasserabsorbierende, schaumförmige, vernetzte Polymerisate mit verbesserter Verteilungswirkung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO2000074844A1 (de) | 1999-06-02 | 2000-12-14 | Basf Aktiengesellschaft | Multimetallcyanid-katalysatoren |
| DE19960148A1 (de) | 1999-12-14 | 2001-06-21 | Basf Ag | Verfahren zur Herstellung von Polyetheralkoholen |
| EP1170274A1 (de) | 2000-06-28 | 2002-01-09 | KAJO-Chemie, chemische und mineraloelhaltige Produkte GmbH | Verfahren zur Herstellung von Polyolen |
| DE10201783A1 (de) * | 2002-01-17 | 2003-08-21 | Stockhausen Chem Fab Gmbh | Verfahren zur Oxidation ungesättigter Kohlenwasserstoffe |
| RU2227133C2 (ru) * | 2002-03-20 | 2004-04-20 | Институт катализа им. Г.К. Борескова СО РАН | Способ получения карбонильных соединений |
| DE10240186A1 (de) | 2002-08-28 | 2004-03-11 | Basf Ag | Verfahren zur Herstellung von emissionsarmen Polyurethan-Weichschaumstoffen |
| WO2006012344A1 (en) | 2004-06-25 | 2006-02-02 | Pittsburg State University | Modified vegetable oil-based polyols |
| US20060229375A1 (en) * | 2005-04-06 | 2006-10-12 | Yu-Ling Hsiao | Polyurethane foams made with alkoxylated vegetable oil hydroxylate |
| BRPI0610831B1 (pt) | 2005-04-25 | 2018-04-10 | Cargill, Incorporated | Espumas de poliuretano compreendendo polióis oligoméricos e métodos de fabricar artigo de espuma moldada de poliuretano e artigo de espuma de poliuretano slabstock |
| US7700661B2 (en) | 2005-05-05 | 2010-04-20 | Sleep Innovations, Inc. | Prime foam containing vegetable oil polyol |
| DE102005056432A1 (de) * | 2005-11-26 | 2007-05-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen auf Basis natürlicher Öle |
| US20070238798A1 (en) * | 2006-04-05 | 2007-10-11 | Mcdaniel Kenneth G | Flexible polyurethane foams made from vegetable oil alkoxylated via DMC-catalysis |
| US8440783B2 (en) | 2006-04-27 | 2013-05-14 | Cargill, Incorporated | Enhanced oligomeric polyols and polymers made therefrom |
| US20070282117A1 (en) | 2006-06-01 | 2007-12-06 | Trevor Newbold | Method of preparing enhanced reactive vegetable oils |
| US7674925B2 (en) | 2006-09-21 | 2010-03-09 | Athletic Polymer Systems, Inc. | Polyols from plant oils and methods of conversion |
| WO2008038596A1 (en) * | 2006-09-27 | 2008-04-03 | Asahi Glass Company, Limited | Process for production of polyether polyol containing material derived from natural oil-and-fat |
| CN101195577A (zh) * | 2007-12-13 | 2008-06-11 | 天津工业大学 | 一种由大豆油制备多元醇的方法 |
-
2010
- 2010-07-09 ES ES10734725T patent/ES2408124T3/es active Active
- 2010-07-09 SG SG10201404567VA patent/SG10201404567VA/en unknown
- 2010-07-09 CN CN2010800396278A patent/CN102498145B/zh not_active Expired - Fee Related
- 2010-07-09 KR KR1020127002509A patent/KR101425734B1/ko not_active Expired - Fee Related
- 2010-07-09 MX MX2012000420A patent/MX2012000420A/es active IP Right Grant
- 2010-07-09 RU RU2012104507/04A patent/RU2510798C2/ru not_active IP Right Cessation
- 2010-07-09 WO PCT/EP2010/059883 patent/WO2011004004A1/de not_active Ceased
- 2010-07-09 MY MYPI2012000017A patent/MY157695A/en unknown
- 2010-07-09 US US13/382,991 patent/US20120108780A1/en not_active Abandoned
- 2010-07-09 EP EP10734725.4A patent/EP2451857B1/de not_active Not-in-force
- 2010-07-09 BR BR112012000634A patent/BR112012000634A2/pt not_active IP Right Cessation
- 2010-07-09 SG SG2011096864A patent/SG177400A1/en unknown
- 2010-07-09 JP JP2012519009A patent/JP5570595B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101425734B1 (ko) | 2014-08-01 |
| SG10201404567VA (en) | 2014-10-30 |
| RU2510798C2 (ru) | 2014-04-10 |
| MX2012000420A (es) | 2012-02-08 |
| CN102498145B (zh) | 2013-10-23 |
| JP2012532948A (ja) | 2012-12-20 |
| SG177400A1 (en) | 2012-02-28 |
| CN102498145A (zh) | 2012-06-13 |
| EP2451857A1 (de) | 2012-05-16 |
| ES2408124T3 (es) | 2013-06-18 |
| US20120108780A1 (en) | 2012-05-03 |
| MY157695A (en) | 2016-07-15 |
| BR112012000634A2 (pt) | 2016-02-10 |
| KR20120034768A (ko) | 2012-04-12 |
| EP2451857B1 (de) | 2013-05-01 |
| WO2011004004A1 (de) | 2011-01-13 |
| JP5570595B2 (ja) | 2014-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2012104507A (ru) | Способ получения полиолов на основе возобновляемого исходного сырья | |
| Román-Figueroa et al. | High-yield production of biodiesel by non-catalytic supercritical methanol transesterification of crude castor oil (Ricinus communis) | |
| Reddy et al. | Direct conversion of wet algae to crude biodiesel under supercritical ethanol conditions | |
| Deviren et al. | Production and physicochemical properties of safflower seed oil extracted using different methods and its conversion to biodiesel | |
| Zhao et al. | Enhancing lipid productivity by co-cultivation of Chlorella sp. U4341 and Monoraphidium sp. FXY-10 | |
| US8765985B2 (en) | Blown corn stillage oil | |
| RU2012146402A (ru) | Активная композиция мягчителя ткани | |
| WO2008063322A3 (en) | Metathesis methods involving hydrogenation and compositions relating to same | |
| Petrovič et al. | The advantages of co-digestion of vegetable oil industry by-products and sewage sludge: Biogas production potential, kinetic analysis and digestate valorisation | |
| US9260372B2 (en) | Method for the production of polyols and uses thereof | |
| WO2011012440A3 (en) | A process for the production of bio-naphtha from complex mixtures of natural occurring fats & oils | |
| RU2012139440A (ru) | Масляные композиции стеаридоновой кислоты | |
| AR056525A1 (es) | Metodo refinado para la fabricacion de etil esteres a partir de sustancias grasas de origen natural | |
| MY185547A (en) | Dry fractionation method for a transesterified oil and fat composition | |
| WO2011008058A3 (ko) | 오일 생성능을 가지는 미생물을 이용한 지방산 알킬에스테르의 제조방법 | |
| CN102257108B (zh) | 甲磺酸用于制备脂肪酸酯的方法 | |
| RU2012104506A (ru) | Способ получения полиолов на основе возобновляемого исходного сырья | |
| RU2015105971A (ru) | 1,3-селективная переэтерификация | |
| Shagal et al. | Epoxidation of Ximenia americana seed oil | |
| RU2014106860A (ru) | Композиция пальмового олеинового масла | |
| Kafuku et al. | Influence of fatty acid profiles during supercritical transesterification of conventional and non-conventional feedstocks: a review | |
| EP2201999A3 (en) | Heterogeneous catalysts for transesterification of triglycerides and preparation methods of same | |
| JP5452582B2 (ja) | C重油代替燃料用グリセリド組成物の製造方法 | |
| CN114540438B (zh) | 一种特种油脂深加工副产物再利用生产甘油二酯油的方法 | |
| CN105647655B (zh) | 一种制备生物柴油的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160710 |