JP2015513546A - ポリオール類の製造方法およびその使用 - Google Patents
ポリオール類の製造方法およびその使用 Download PDFInfo
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- JP2015513546A JP2015513546A JP2014559852A JP2014559852A JP2015513546A JP 2015513546 A JP2015513546 A JP 2015513546A JP 2014559852 A JP2014559852 A JP 2014559852A JP 2014559852 A JP2014559852 A JP 2014559852A JP 2015513546 A JP2015513546 A JP 2015513546A
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- 238000004519 manufacturing process Methods 0.000 title description 7
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- 239000000194 fatty acid Substances 0.000 claims abstract description 69
- 229930195729 fatty acid Natural products 0.000 claims abstract description 69
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical class [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 52
- -1 ester polyols Chemical class 0.000 claims abstract description 39
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 38
- 238000004821 distillation Methods 0.000 claims abstract description 13
- 238000005194 fractionation Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 44
- 238000005949 ozonolysis reaction Methods 0.000 claims description 35
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 235000019482 Palm oil Nutrition 0.000 claims description 12
- 239000002540 palm oil Substances 0.000 claims description 12
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- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 9
- 239000000314 lubricant Substances 0.000 claims description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
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- 239000006260 foam Substances 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
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- 238000000576 coating method Methods 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 208000007976 Ketosis Diseases 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 150000001323 aldoses Chemical class 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 150000002584 ketoses Chemical class 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 150000005846 sugar alcohols Chemical class 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 235000019737 Animal fat Nutrition 0.000 claims 2
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- 235000015277 pork Nutrition 0.000 claims 2
- 235000012424 soybean oil Nutrition 0.000 claims 2
- 239000003549 soybean oil Substances 0.000 claims 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical group NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- 241000272525 Anas platyrhynchos Species 0.000 claims 1
- 235000016401 Camelina Nutrition 0.000 claims 1
- 244000197813 Camelina sativa Species 0.000 claims 1
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- 235000019486 Sunflower oil Nutrition 0.000 claims 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims 1
- 235000015278 beef Nutrition 0.000 claims 1
- 235000014121 butter Nutrition 0.000 claims 1
- 239000000828 canola oil Substances 0.000 claims 1
- 235000019519 canola oil Nutrition 0.000 claims 1
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 235000005687 corn oil Nutrition 0.000 claims 1
- 239000002285 corn oil Substances 0.000 claims 1
- 235000012343 cottonseed oil Nutrition 0.000 claims 1
- 239000002385 cottonseed oil Substances 0.000 claims 1
- 235000021323 fish oil Nutrition 0.000 claims 1
- 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 1
- 235000021388 linseed oil Nutrition 0.000 claims 1
- 239000000944 linseed oil Substances 0.000 claims 1
- 240000004308 marijuana Species 0.000 claims 1
- 239000008164 mustard oil Substances 0.000 claims 1
- 239000004006 olive oil Substances 0.000 claims 1
- 235000008390 olive oil Nutrition 0.000 claims 1
- 150000002943 palmitic acids Chemical class 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- 235000005713 safflower oil Nutrition 0.000 claims 1
- 239000003813 safflower oil Substances 0.000 claims 1
- 235000011803 sesame oil Nutrition 0.000 claims 1
- 239000008159 sesame oil Substances 0.000 claims 1
- 239000002600 sunflower oil Substances 0.000 claims 1
- 239000010497 wheat germ oil Substances 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 abstract description 19
- 235000003441 saturated fatty acids Nutrition 0.000 abstract description 15
- 238000002425 crystallisation Methods 0.000 abstract description 8
- 230000032050 esterification Effects 0.000 abstract description 8
- 238000005886 esterification reaction Methods 0.000 abstract description 8
- 230000008025 crystallization Effects 0.000 abstract description 7
- 238000013459 approach Methods 0.000 abstract description 5
- 238000007796 conventional method Methods 0.000 abstract description 5
- 238000002203 pretreatment Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 description 28
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 15
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 235000021314 Palmitic acid Nutrition 0.000 description 7
- 235000021355 Stearic acid Nutrition 0.000 description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 7
- 239000008117 stearic acid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004508 fractional distillation Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical compound [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- BMQNWLUEXNQIGL-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O.CCCCCCCCC(O)=O BMQNWLUEXNQIGL-UHFFFAOYSA-N 0.000 description 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- 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
- 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
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
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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)
Abstract
Description
[参考文献]
Claims (17)
- エステルポリオールの生成物を製造する方法であって、
少なくとも1つのトリグリセリドを加水分解して、少なくとも1つの脂肪酸を製造するステップ;
前記脂肪酸(単数または複数)を少なくとも1つのモノアルコールでエステル化して、少なくとも1つの脂肪酸アルキルエステルを形成するステップ;
前記の少なくとも1つの脂肪アルキル酸エステルの蒸留による分画を行なって、前記の少なくとも1つの脂肪アルキル酸エステルから、飽和物(saturates)を部分的に除去するステップ;
前記の少なくとも1つの分画された脂肪アルキル酸エステルをオゾン分解に供して、オゾンエステル類の混合物を製造するステップ;および、
前記のオゾンエステル類の混合物を一級ポリオールで同時にエステル化およびエステル交換して、エステルポリオールの生成物を製造するステップ、
を含む、
方法。 - エステルポリオールの生成物を製造する方法であって、
少なくとも1つのトリグリセリドを加水分解して、少なくとも1つの脂肪酸を製造するステップ;
前記の脂肪酸(単数または複数)を少なくとも1つのモノアルコールでエステル化して、少なくとも1つの脂肪酸アルキルエステルを形成するステップ;
前記の少なくとも1つの脂肪酸アルキルエステルをオゾン分解に供して、オゾンエステル類の混合物を製造するステップ;
前記のオゾンエステル類の混合物の蒸留による分画を行なって、前記のオゾンエステル類の混合物から飽和物(saturates)を部分的に除去するステップ;および、
前記の分画されたオゾンエステル類の混合物を、一級ポリオールで同時にエステル化およびエステル交換して、エステルポリオールの生成物を製造するステップ、
を含む、
方法。 - 請求項1から2のいずれか一項に記載の方法であって、
前記の少なくとも1つのモノアルコールが、メタノール、エタノール、1−プロパノールおよびそれらの異性体、1−ブタノールまたはそれらの異性体、1−ペンタノールまたはそれらの異性体、および1−ヘキサノールまたはそれらの異性体を含むことを特徴とする、
方法。 - 請求項3に記載の方法であって、
前記の少なくとも1つのモノアルコールが、メタノールであることを特徴とする、
方法。 - 請求項3に記載の方法であって、
前記の少なくとも1つのモノアルコールが、1−ブタノールであることを特徴とする、
方法。 - 請求項3に記載の方法であって、
前記の少なくとも1つのモノアルコールが、1−ヘキサノールであることを特徴とする、
方法。 - 請求項1から6のいずれか一項に記載の方法であって、
前記トリグリセリドが、植物油および/または動物性脂肪を含むことを特徴とする、
方法。 - 請求項7に記載の方法であって、
前記植物油が、大豆油、サフラワー油、亜麻仁油、コーン油、ヒマワリ油、オリーブ油、キャノーラ油、ゴマ油、綿実油、カラシ油、カメリナ油、ジャトロファ油、ピーナッツ油、ココナッツ油、ナタネ油、中国牛脂油、キリ油、ヒマシ油、藻類油、小麦胚芽油、大豆油、大麻油、およびパーム油から選択されることを特徴とする、
方法。 - 請求項7に記載の方法であって、
前記動物性脂肪が、魚油、豚脂、ダック脂、バター、ウシまたはブタ獣脂、およびそれらの混合物から選択されることを特徴とする、
方法。 - 請求項1または2に記載の方法であって、
前記の飽和物が、パルミチン酸エステルおよびステアリン酸エステルを含むことを特徴とする、
方法。 - 請求項1または2に記載の方法であって、
前記トリグリセリドが、パーム油、オレイン、パーム脂肪酸留出物(PFAD)またはパーム核脂肪酸留出物(PKFAD)から選択されることを特徴とする、
方法。 - 請求項11に記載の方法であって、
前記方法が、前記トリグリセリドをモノアルコールとエステル交換して、前記の少なくとも1つの脂肪酸アルキルエステルを製造するステップをさらに含み、
前記トリグリセリドが、パーム油またはオレインであることを特徴とする、
方法。 - 請求項1から12のいずれか一項に記載の方法であって、
前記一級ポリオールが、グリセリン、トリメチロールプロパン、ペンタエリスリトール、1,2−プロピレングリコール、1,3−プロピレングリコール、2−メチル−1,3−プロパンジオール、1,4−ブタンジオール、エチレングリコール、グルシトールフルクトース、グルコース、スクロース、アルドース、ケトース、アルジトール、二糖類、またはそれらの組み合わせから選択されることを特徴とする、
方法。 - 請求項1から13のいずれか一項に記載の方法により得られる、または得ることのできる、
エステルポリオール。 - 請求項14に記載のエステルポリオールを含む、
製造品。 - 請求項14に記載のエステルポリオールを含む、
コーティングまたはフォーム。 - 請求項14に記載のエステルポリオールを含む、
潤滑剤素材のための中間体。
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