RU2472790C2 - Кетали глицериллевулината и их применение - Google Patents
Кетали глицериллевулината и их применение Download PDFInfo
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- RU2472790C2 RU2472790C2 RU2008124895A RU2008124895A RU2472790C2 RU 2472790 C2 RU2472790 C2 RU 2472790C2 RU 2008124895 A RU2008124895 A RU 2008124895A RU 2008124895 A RU2008124895 A RU 2008124895A RU 2472790 C2 RU2472790 C2 RU 2472790C2
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- -1 Glyceryl levulinate Chemical compound 0.000 title claims description 59
- 229940058352 levulinate Drugs 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 232
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 180
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 26
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical group CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 163
- 239000000203 mixture Substances 0.000 claims description 108
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 239000003054 catalyst Substances 0.000 claims description 59
- 238000004821 distillation Methods 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 32
- 238000005809 transesterification reaction Methods 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 150000004676 glycans Chemical class 0.000 claims description 12
- 229920001282 polysaccharide Polymers 0.000 claims description 12
- 239000005017 polysaccharide Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- BGLUXFNVVSVEET-UHFFFAOYSA-N beta-angelica lactone Chemical compound CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 0.000 claims 1
- 229920000739 poly(3-hydroxycarboxylic acid) polymer Polymers 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 abstract description 61
- 239000000126 substance Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 230000015572 biosynthetic process Effects 0.000 description 46
- 239000004814 polyurethane Substances 0.000 description 34
- 229920002635 polyurethane Polymers 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 31
- 150000002924 oxiranes Chemical group 0.000 description 30
- 230000002829 reductive effect Effects 0.000 description 30
- 239000007788 liquid Substances 0.000 description 29
- 239000004014 plasticizer Substances 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 23
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 17
- 239000000178 monomer Substances 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 229920000915 polyvinyl chloride Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000004800 polyvinyl chloride Substances 0.000 description 14
- 150000005846 sugar alcohols Polymers 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 150000003626 triacylglycerols Chemical class 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000012634 fragment Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
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- 239000006260 foam Substances 0.000 description 8
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 229920001169 thermoplastic Polymers 0.000 description 8
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 208000034530 PLAA-associated neurodevelopmental disease Diseases 0.000 description 5
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- 230000009477 glass transition Effects 0.000 description 5
- 150000002314 glycerols Chemical class 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical class O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 150000001261 hydroxy acids Chemical class 0.000 description 5
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical class N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 5
- 235000019796 monopotassium phosphate Nutrition 0.000 description 5
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 5
- 229920000747 poly(lactic acid) Polymers 0.000 description 5
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
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- 238000004817 gas chromatography Methods 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 229920000126 latex Polymers 0.000 description 1
- 150000004730 levulinic acid derivatives Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LJUGGVUDXRWTGO-UHFFFAOYSA-N methyl 4,4-dimethoxypentanoate Chemical compound COC(=O)CCC(C)(OC)OC LJUGGVUDXRWTGO-UHFFFAOYSA-N 0.000 description 1
- NQKYFDXCRYGCEQ-UHFFFAOYSA-N methyl 8-(3-octyloxiren-2-yl)octanoate Chemical compound CCCCCCCCC1=C(CCCCCCCC(=O)OC)O1 NQKYFDXCRYGCEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 150000005209 naphthoic acids Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005188 oxoalkyl group Chemical group 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
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- 229940059574 pentaerithrityl Drugs 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
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- 150000003138 primary alcohols Chemical class 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- ZJVAANZDGCUXLB-UHFFFAOYSA-N sodium;3-methylbutan-1-olate Chemical compound [Na+].CC(C)CC[O-] ZJVAANZDGCUXLB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
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- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4283—Hydroxycarboxylic acid or ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
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| US73898805P | 2005-11-22 | 2005-11-22 | |
| US60/738,988 | 2005-11-22 |
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| RU2008124895A RU2008124895A (ru) | 2009-12-27 |
| RU2472790C2 true RU2472790C2 (ru) | 2013-01-20 |
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| RU2008124895A RU2472790C2 (ru) | 2005-11-22 | 2006-11-22 | Кетали глицериллевулината и их применение |
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| IN (1) | IN263389B (enExample) |
| MX (1) | MX301032B (enExample) |
| MY (1) | MY166613A (enExample) |
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| SG (1) | SG142841A1 (enExample) |
| WO (1) | WO2007062118A2 (enExample) |
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| CN101346067B (zh) | 2005-11-22 | 2013-03-27 | 塞格提斯有限公司 | 甘油乙酰丙酸酯缩酮及其用途 |
| EP2185625A1 (en) | 2007-09-04 | 2010-05-19 | Segetis, Inc. | Ketal compounds from polyols and oxocarboxylates |
| CN101883773B (zh) * | 2007-10-09 | 2014-05-21 | 希凯迪斯股份有限公司 | 聚缩酮，合成和应用 |
| WO2009048874A1 (en) * | 2007-10-09 | 2009-04-16 | Segetis, Inc. | Method of making ketals and acetals |
| WO2009146202A2 (en) * | 2008-04-16 | 2009-12-03 | Segetis, Inc. | Transketalized compositions, synthesis, and applications |
| EP2367811A1 (en) * | 2008-09-25 | 2011-09-28 | Segetis, Inc. | Ketal ester derivatives |
| WO2010073261A2 (en) * | 2008-12-22 | 2010-07-01 | Ranka, Seema Ajay | Asphalt-mineral compositions |
| BRPI0922127A2 (pt) * | 2008-12-23 | 2016-09-06 | Segetis Inc | composto, formulação, artigo, polímero e método para fabricar poliamida. |
| WO2010138907A1 (en) | 2009-05-29 | 2010-12-02 | Segetis Inc. | Solvent, solution, cleaning composition and methods |
| JP2012528198A (ja) * | 2009-05-29 | 2012-11-12 | エクスエルテラ， インコーポレイテッド | アンヒドロペンチトールのケタールエステルおよびその使用 |
| JP5882204B2 (ja) * | 2009-06-22 | 2016-03-09 | サジティス・インコーポレイテッド | ケタール化合物およびそれらの使用 |
| US8598109B2 (en) * | 2009-09-11 | 2013-12-03 | Method Products, Inc. | Fabric softener |
| KR20130070608A (ko) * | 2010-05-10 | 2013-06-27 | 세게티스, 인코포레이티드. | 미립자 고체에 대한 분산제 및 슬립제로서의 알킬 케탈 에스터 및 그의 제조방법, 및 용도 |
| KR20130136955A (ko) * | 2010-08-03 | 2013-12-13 | 세게티스, 인코포레이티드. | 아세탈 및 케탈의 제조방법, 및 이에 의해 생성된 아세탈 및 케탈 |
| US8828917B2 (en) * | 2010-08-12 | 2014-09-09 | Segetis, Inc. | Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof |
| WO2012021826A2 (en) | 2010-08-12 | 2012-02-16 | Segetis, Inc. | Latex coating compositions including carboxy ester ketal coalescents, methods of manufacture, and uses thereof |
| JP2013538060A (ja) | 2010-08-30 | 2013-10-10 | アルゼダ コーポレーション | レブリン酸、レブリン酸エステル、バレロラクトン、およびこれらの誘導体の産生のための発酵経路 |
| IL207945A0 (en) | 2010-09-02 | 2010-12-30 | Robert Jansen | Method for the production of carbohydrates |
| WO2012033813A2 (en) | 2010-09-07 | 2012-03-15 | Segetis, Inc. | Compositions for dyeing keratin fibers |
| WO2012037122A2 (en) * | 2010-09-13 | 2012-03-22 | Segetis, Inc. | Fabric softener compositions and methods of manufacture thereof |
| FR2965814B1 (fr) | 2010-10-08 | 2012-11-16 | Roquette Freres | Plastification de polyesters aliphatiques par des esters alkyliques de dianhydrohexitols |
| KR20130131323A (ko) * | 2010-10-18 | 2013-12-03 | 세게티스, 인코포레이티드. | 카복시 에스터 케탈을 포함하는 수희석성 코팅 조성물, 그리고 그의 제조방법 및 용도 |
| US8383710B2 (en) | 2010-10-21 | 2013-02-26 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents |
| US9034964B2 (en) | 2010-10-21 | 2015-05-19 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents that are hydroxypivalyl hydroxypivalate esters |
| US8507718B2 (en) | 2010-11-11 | 2013-08-13 | Segetis, Inc. | Ketocarboxylic acids, methods of manufacture and uses thereof |
| KR20140009155A (ko) | 2010-11-11 | 2014-01-22 | 세게티스, 인코포레이티드. | 폴리하이드록시 케탈 에스터 부가물, 그의 제조방법 및 용도 |
| US9212176B2 (en) | 2010-11-11 | 2015-12-15 | Segetis, Inc. | Polyketal adducts, methods of manufacture and uses thereof |
| US9126890B2 (en) * | 2011-10-20 | 2015-09-08 | International Flavors & Fragrances Inc. | Low volatile reactive malodor counteractives and methods of use thereof |
| US9617608B2 (en) | 2011-10-10 | 2017-04-11 | Virdia, Inc. | Sugar compositions |
| US20130087073A1 (en) | 2011-10-11 | 2013-04-11 | Segetis, Inc. | Stabilized levulinic ester ketals |
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