JP2011079824A - ポリオールエステルの色を明るくする方法 - Google Patents
ポリオールエステルの色を明るくする方法 Download PDFInfo
- Publication number
- JP2011079824A JP2011079824A JP2010226265A JP2010226265A JP2011079824A JP 2011079824 A JP2011079824 A JP 2011079824A JP 2010226265 A JP2010226265 A JP 2010226265A JP 2010226265 A JP2010226265 A JP 2010226265A JP 2011079824 A JP2011079824 A JP 2011079824A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- glycol
- polyol
- reaction
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 polyol ester Chemical class 0.000 title claims abstract description 122
- 229920005862 polyol Polymers 0.000 title claims abstract description 91
- 238000004519 manufacturing process Methods 0.000 title abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 52
- 150000003077 polyols Chemical class 0.000 claims abstract description 20
- 239000003463 adsorbent Substances 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 238000011282 treatment Methods 0.000 claims description 48
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 239000002994 raw material Substances 0.000 claims description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 229910000510 noble metal Inorganic materials 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 8
- 230000000737 periodic effect Effects 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 7
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 6
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 5
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 4
- YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 claims description 4
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000010970 precious metal Substances 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 3
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 claims description 2
- GCDUWJFWXVRGSM-UHFFFAOYSA-N 2-[2-(2-heptanoyloxyethoxy)ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOC(=O)CCCCCC GCDUWJFWXVRGSM-UHFFFAOYSA-N 0.000 claims description 2
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-UHFFFAOYSA-N 0.000 claims description 2
- SSKNCQWPZQCABD-UHFFFAOYSA-N 2-[2-[2-(2-heptanoyloxyethoxy)ethoxy]ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCC SSKNCQWPZQCABD-UHFFFAOYSA-N 0.000 claims description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 2
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 claims 1
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 claims 1
- RXGPYPPCEXISOV-UHFFFAOYSA-N 2-propylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCC RXGPYPPCEXISOV-UHFFFAOYSA-N 0.000 claims 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000005385 peroxodisulfate group Chemical group 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 14
- 239000000047 product Substances 0.000 abstract description 14
- 238000007730 finishing process Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 56
- 150000002148 esters Chemical class 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 30
- 150000002978 peroxides Chemical class 0.000 description 21
- 238000005886 esterification reaction Methods 0.000 description 20
- 239000002253 acid Substances 0.000 description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 230000032050 esterification Effects 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 238000001256 steam distillation Methods 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000011949 solid catalyst Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GORMSINSWZJIKL-UHFFFAOYSA-N [3-(2-ethylhexanoyloxy)-2,2-dimethylpropyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC(C)(C)COC(=O)C(CC)CCCC GORMSINSWZJIKL-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- HIPPBUJQSIICJN-UHFFFAOYSA-N 3385-61-3 Chemical compound C12CC=CC2C2CC(O)C1C2 HIPPBUJQSIICJN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XNKKAPGFWPIOBY-UHFFFAOYSA-N C(C)C(C(=O)O)CC.C(CCCCC)(=O)O Chemical compound C(C)C(C(=O)O)CC.C(CCCCC)(=O)O XNKKAPGFWPIOBY-UHFFFAOYSA-N 0.000 description 1
- MSLXMPJRKAWTME-UHFFFAOYSA-N CC(CC(O)=O)CC(C)(C)C.CCCCCC(CCC)C(O)=O Chemical compound CC(CC(O)=O)CC(C)(C)C.CCCCCC(CCC)C(O)=O MSLXMPJRKAWTME-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000009043 Chemical Burns Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YYVJAABUJYRQJO-UHFFFAOYSA-N isomyristic acid Chemical compound CC(C)CCCCCCCCCCC(O)=O YYVJAABUJYRQJO-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- FDSIFWDGJSJXMP-UHFFFAOYSA-N methyl 3-methyl-5-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazole-4-carboxylate Chemical compound CC1=NOC(C2=NOC(C)=C2)=C1C(=O)OC FDSIFWDGJSJXMP-UHFFFAOYSA-N 0.000 description 1
- SAOSCTYRONNFTC-UHFFFAOYSA-N methyl-capric acid Natural products CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910002028 silica xerogel Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
【解決手段】
本発明は、ポリオールを炭素原子数3〜20の線状もしくは分枝状脂肪族モノカルボン酸と反応させることによってポリオールエステルの色を明るくする方法であって、反応生成物の仕上げを吸着剤の使用無しに行い、そして過酸化物化合物での処理及びその直後の水蒸気処理、その後の乾燥を含む、前記方法。
【選択図】なし
Description
R(OH)n (I)
式中、Rは、炭素原子数2〜20、好ましくは2〜10の脂肪族または環状脂肪族炭化水素残基を意味し、そしてnは2〜8の整数、好ましくは2、3、4、5または6を意味する。
H−(−O−[−CR1R2−]m−)o−OH (II)
式中、R1及びR2は、互いに独立して、水素、炭素原子数1〜5のアルキル基、好ましくはメチル、エチルもしくはプロピル、または炭素原子数1〜5のヒドロキシアルキル基、好ましくはヒドロキシメチル基を意味し、mは1〜10の整数、好ましくは1〜8の整数、特に1、2、3または4を意味し、oは2〜15の整数、好ましくは2〜8の整数、特に2、3、4または5を意味する。
過酸化水素水溶液での粗製トリエチレングリコール−ジ−2−エチルヘキサノエートの処理は以下の条件で行った。
水蒸気蒸留を白金ネットを使用せずに行ったことだけを除いて例2を例1と同様に行った。得られた蒸留物は、13megO/kgの過酸化物含有率を有していた。精製したポリオールエステルの特性値は、例1に従い示された値に相当した。
後で過酸化水素で処理を行ったNPG−ジ−2−エチルヘキサノエートの製造
2−エチルヘキサン酸でのネオペンチルグリコールのエステル化を、攪拌機、内部温度計及び水分離器を備えた加熱可能な1L容積の四つ首フラスコ中で行った。
ガスクロマトグラフィーで求めた含有率:
2−エチルヘキサン酸でのネオペンチルグリコールのエステル化、その後の未反応の過剰の2−エチル−ヘキサン酸の分離を、例3に従い行った。過酸化水素での処理はせずに、次いで水蒸気処理を180℃で30分間の期間にわたり行い、その後の乾燥を120℃で15分間行った。残留物中に生じたネオペンチルグリコール−ジ−2−エチルヘキサノエートは以下の特性値を有した。
ガスクロマトグラフィーで求めた含有率:
Claims (21)
- ポリオールを炭素原子数3〜20の線状もしくは分枝状脂肪族モノカルボン酸と反応させ、次いで反応混合物を、吸着剤を使用せずに、仕上げすることによってポリオールエステルの色を明るくする方法であって、未反応の原料化合物を分離した後に、反応生成物を過酸化物化合物で処理し、その直後に、更なる中間段階無しに、水蒸気処理を行い、そして後に残ったポリオールエステルを乾燥することを特徴とする、上記方法。
- 過酸化物化合物の有効成分含有率が、全混合物を基準にして0.03〜1.0重量%、好ましくは0.08〜0.3重量%であることを特徴とする、請求項1の方法。
- 過酸化物化合物が、過酸化水素、有機過カルボン酸、有機ヒドロペルオキシド、アルカリ−もしくはアルカリ土類金属過ホウ酸塩、アルカリ−もしくはアルカリ土類金属過カルボン酸塩、アルカリ−もしくはアルカリ土類金属ペルオキソジスルフェート、及びアルカリ−もしくはアルカリ土類金属ペルオキソホスフェートから選択されることを特徴とする、請求項1または2の方法。
- 過酸化水素を、10重量%超、好ましくは30〜50重量%の過酸化水素含有率を有する水溶液の形で使用することを特徴とする、請求項3の方法。
- 過酸化物化合物での処理を70〜160℃、好ましくは100〜120℃の温度で行うことを特徴とする、請求項1〜4のいずれか一つの方法。
- 水蒸気処理を、100〜250℃、好ましくは150〜220℃、特に170〜200℃の温度で行うことを特徴とする、請求項1〜5のいずれか一つの方法。
- 水蒸気処理の際に排出される水蒸気を、ガス状態で、元素周期律表の第9族〜第11族の貴金属と接触させることを特徴とする、請求項1〜6のいずれか一つの方法。
- 水蒸気処理の際に排出される水蒸気を先ず凝縮し、そしてこの凝縮された液状蒸留物を、元素周期律表の第9族〜第11族の貴金属と接触させることを特徴とする、請求項1〜6のいずれか一つの方法。
- 元素周期律表の第9族〜第11族の貴金属を固定配置することを特徴とする、請求項7または8の方法。
- 元素周期律表の第9族〜第11族の貴金属がキャリア上に担持されていることを特徴とする、請求項9の方法。
- キャリアとして、二酸化ケイ素、酸化アルミニウム、活性炭、二酸化チタンまたは二酸化ジルコニウムを使用することを特徴とする、請求項10の方法。
- 元素周期律表の第9族〜第11族の貴金属が、織成物、ネット、編成物、線条、線状の玉状物またはスポンジの形で配置されることを特徴とする、請求項9の方法。
- 元素周期律表の第9族〜第11族の貴金属としてパラジウムまたは白金を使用することを特徴とする、請求項7〜12のいずれか一つの方法。
- ポリオールエステルを、80〜250℃、好ましくは100〜180℃の温度及び0.2〜500hPa、好ましくは1〜200hPa、特に1〜20hPaの圧力で乾燥することを特徴とする、請求項1〜13のいずれか一つの方法。
- 後に残ったポリオールエステルを、水蒸気処理の直後に、更なる中間段階無しで、乾燥することを特徴とする、請求項1〜14のいずれか一つの方法。
- ポリオールとして、以下の一般式(I)の化合物を使用することを特徴とする、請求項1〜15のいずれか一つの方法。
R(OH)n (I)
[式中、Rは、炭素原子数2〜20、好ましくは2〜10の脂肪族または環状脂肪族炭化水素残基を意味し、そしてnは2〜8の整数、好ましくは2、3、4、5または6を意味する] - ポリオールとして、次の一般式(II)の化合物を使用することを特徴とする、請求項1〜15のいずれか一つの方法。
H−(−O−[−CR1R2−]m−)o−OH (II)
[式中、R1及びR2は、互いに独立して、水素、炭素原子数1〜5のアルキル基、好ましくはメチル、エチルもしくはプロピル、または炭素原子数1〜5のヒドロキシアルキル基、好ましくはヒドロキシメチル基を意味し、mは、1〜10の整数、好ましくは1〜8の整数、特に1、2、3または4を意味し、oは2〜15の整数、好ましくは2〜8の整数、特に2、3、4または5を意味する] - ポリオールとして、1,2−プロパンジオール、1,3−プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、2,2−ジメチロールブタン、トリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、2,2,4−トリメチルペンタン−1,3−ジオール、1,2−ヘキサンジオール、1,6−ヘキサンジオール、ペンタエリトリトール、エチレングリコールまたは3(4),8(9)−ジヒドロキシメチルトリシクロ[5.2.1.02.6]デカンを使用することを特徴とする、請求項16の方法。
- ポリオールとして、ジ−トリメチロールプロパン、ジ−ペンタエリトリトール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコールまたはテトラプロピレングリコールを使用する、請求項17の方法。
- 脂肪族モノカルボン酸として、プロピオン酸、n−酪酸、イソ酪酸、n−ペンタン酸、2−メチル酪酸、3−メチル酪酸、2−メチルペンタン酸、n−ヘキサン酸、2−エチル酪酸、n−ヘプタン酸、2−メチルヘキサン酸、2−エチルヘキサン酸、n−ノナン酸、2−メチルオクタン酸、イソノナン酸、3,5,5−トリメチルヘキサン酸または2−プロピルヘプタン酸を反応させることを特徴とする、請求項1〜19のいずれか一つの方法。
- トリエチレングリコール−ジ−2−エチルヘキサノエート、テトラエチレングリコール−ジ−n−ヘプタノエート、トリエチレングリコール−ジ−2−エチルブチレート、トリエチレングリコール−ジ−n−ヘプタノエートまたはテトラエチレングリコール−ジ−2−エチルヘキサノエートを製造するための、請求項1〜20のいずれか一つの方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009048773A DE102009048773A1 (de) | 2009-10-08 | 2009-10-08 | Verfahren zur Farbaufhellung von Polyolestern |
DE102009048773.5 | 2009-10-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011079824A true JP2011079824A (ja) | 2011-04-21 |
JP5641643B2 JP5641643B2 (ja) | 2014-12-17 |
Family
ID=43430719
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010226265A Active JP5641643B2 (ja) | 2009-10-08 | 2010-10-06 | ポリオールエステルの色を明るくする方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8158816B2 (ja) |
EP (1) | EP2308822B1 (ja) |
JP (1) | JP5641643B2 (ja) |
CN (1) | CN102030636B (ja) |
CA (1) | CA2716915A1 (ja) |
DE (1) | DE102009048773A1 (ja) |
ES (1) | ES2602831T3 (ja) |
HK (1) | HK1152518A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160055808A (ko) * | 2013-09-14 | 2016-05-18 | 옥세아 게엠베하 | 폴리올 에스테르의 후처리 방법 |
KR20160084381A (ko) * | 2013-11-02 | 2016-07-13 | 옥세아 게엠베하 | 폴리올 에스테르 제조시 사이드-스트림으로부터 폴리올 에스테르-풍부 생성물 스트림을 수득하는 방법 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009048774A1 (de) * | 2009-10-08 | 2011-04-28 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
DE102010027458A1 (de) * | 2010-07-17 | 2012-01-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
JP6159373B2 (ja) * | 2015-10-07 | 2017-07-05 | 出光興産株式会社 | 冷凍機油、冷凍機用組成物、冷凍機及び冷凍機油の選定方法 |
SE540729C2 (en) * | 2016-05-03 | 2018-10-23 | Perstorp Ab | A method and equipment for producing an ester |
WO2019059800A1 (en) | 2017-09-21 | 2019-03-28 | Public Joint Stock Company "Sibur Holding" | PROCESS FOR THE PREPARATION OF GLYCOL ESTERS WITH LOW COLOR AND PEROXIDE CONTENT |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62181236A (ja) * | 1986-02-04 | 1987-08-08 | Nisshin Oil Mills Ltd:The | 1,3―ジオールエステルを含有する化粧料 |
JPS6323838A (ja) * | 1986-07-11 | 1988-02-01 | ヒユ−ルス・アクチエンゲゼルシヤフト | 炭水化物−脂肪酸エステル及びその製造方法 |
JPH10158198A (ja) * | 1996-11-29 | 1998-06-16 | Mitsubishi Gas Chem Co Inc | 有機過酸化物の分解方法 |
JP2005513239A (ja) * | 2001-12-20 | 2005-05-12 | フエロ コーポレーション | グリセリントリエステル可塑剤 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD57596A (ja) * | ||||
US2469446A (en) | 1944-08-08 | 1949-05-10 | Drew & Co Inc E F | Mixed esters of fatty acids |
US2628249A (en) | 1951-01-03 | 1953-02-10 | Pittsburgh Coke & Chemical Co | Esterification process |
DE2729627C2 (de) | 1977-06-30 | 1983-03-10 | Nižnetagil'skoe proizvodstvennoe ob"edinenie Uralchimplast, Nižnij Tagil, Sverdlovskaja oblast' | Verfahren zur Herstellung von farblosen, als Weichmacher verwendbaren Carbonsäureestern |
US4137099A (en) | 1977-07-11 | 1979-01-30 | General Electric Company | Method of controlling leakage currents and reverse recovery time of rectifiers by hot electron irradiation and post-annealing treatments |
SU979329A1 (ru) * | 1980-11-20 | 1982-12-07 | Институт Органической Химии Ан Усср | Способ очистки пластификаторов |
DE3240892A1 (de) * | 1982-11-05 | 1984-05-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von carbonsaeureestern von hexiten |
CA2027418C (en) * | 1989-10-16 | 1997-12-09 | Robert Houston | Polyol polyester synthesis |
US5324853A (en) | 1993-01-19 | 1994-06-28 | Exxon Chemical Patents Inc. | Process for the production of plasticizer and polyolesters |
DE4304468A1 (de) * | 1993-02-15 | 1994-08-18 | Henkel Kgaa | Verfahren zur Herstellung hellfarbiger Polyolester |
DE19940991B4 (de) | 1999-08-28 | 2007-04-05 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Esterweichmachern |
WO2002060975A1 (en) * | 2001-01-31 | 2002-08-08 | The Procter & Gamble Company | Synthesis of polyol medium fatty acid polyesters |
-
2009
- 2009-10-08 DE DE102009048773A patent/DE102009048773A1/de not_active Ceased
-
2010
- 2010-09-17 ES ES10009852.4T patent/ES2602831T3/es active Active
- 2010-09-17 EP EP10009852.4A patent/EP2308822B1/de active Active
- 2010-09-29 CN CN201010502495XA patent/CN102030636B/zh active Active
- 2010-10-06 US US12/924,854 patent/US8158816B2/en active Active
- 2010-10-06 CA CA2716915A patent/CA2716915A1/en not_active Abandoned
- 2010-10-06 JP JP2010226265A patent/JP5641643B2/ja active Active
-
2011
- 2011-06-28 HK HK11106629.3A patent/HK1152518A1/xx not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62181236A (ja) * | 1986-02-04 | 1987-08-08 | Nisshin Oil Mills Ltd:The | 1,3―ジオールエステルを含有する化粧料 |
JPS6323838A (ja) * | 1986-07-11 | 1988-02-01 | ヒユ−ルス・アクチエンゲゼルシヤフト | 炭水化物−脂肪酸エステル及びその製造方法 |
JPH10158198A (ja) * | 1996-11-29 | 1998-06-16 | Mitsubishi Gas Chem Co Inc | 有機過酸化物の分解方法 |
JP2005513239A (ja) * | 2001-12-20 | 2005-05-12 | フエロ コーポレーション | グリセリントリエステル可塑剤 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160055808A (ko) * | 2013-09-14 | 2016-05-18 | 옥세아 게엠베하 | 폴리올 에스테르의 후처리 방법 |
KR102313565B1 (ko) | 2013-09-14 | 2021-10-20 | 옥세아 게엠베하 | 폴리올 에스테르의 후처리 방법 |
KR20160084381A (ko) * | 2013-11-02 | 2016-07-13 | 옥세아 게엠베하 | 폴리올 에스테르 제조시 사이드-스트림으로부터 폴리올 에스테르-풍부 생성물 스트림을 수득하는 방법 |
JP2016535029A (ja) * | 2013-11-02 | 2016-11-10 | オクセア・ゲゼルシャフト・ミト・べシュレンクテル・ハフツング | ポリオールエステル製造における副流から、ポリオールエステルが富化された生成物流を得るための方法 |
KR102309656B1 (ko) * | 2013-11-02 | 2021-10-12 | 옥세아 게엠베하 | 폴리올 에스테르 제조시 사이드-스트림으로부터 폴리올 에스테르-풍부 생성물 스트림을 수득하는 방법 |
Also Published As
Publication number | Publication date |
---|---|
US8158816B2 (en) | 2012-04-17 |
CA2716915A1 (en) | 2011-04-08 |
HK1152518A1 (en) | 2012-03-02 |
CN102030636B (zh) | 2013-11-13 |
EP2308822B1 (de) | 2016-08-31 |
ES2602831T3 (es) | 2017-02-22 |
US20110086997A1 (en) | 2011-04-14 |
CN102030636A (zh) | 2011-04-27 |
EP2308822A3 (de) | 2011-12-21 |
DE102009048773A1 (de) | 2011-04-21 |
EP2308822A2 (de) | 2011-04-13 |
JP5641643B2 (ja) | 2014-12-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5637594B2 (ja) | ポリオールエステルの製造方法 | |
JP5641644B2 (ja) | ポリオールエステルの色を明るくする方法 | |
JP5686466B2 (ja) | ポリオールエステルの製造方法 | |
JP5641643B2 (ja) | ポリオールエステルの色を明るくする方法 | |
JP5686485B2 (ja) | ポリオールエステルの製造方法 | |
JP6173463B2 (ja) | ポリオールエステルの製造方法 | |
JP5801888B2 (ja) | ポリエステルの後処理方法 | |
JP6392877B2 (ja) | ポリオールエステルの後処理方法 | |
KR102309656B1 (ko) | 폴리올 에스테르 제조시 사이드-스트림으로부터 폴리올 에스테르-풍부 생성물 스트림을 수득하는 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110509 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130607 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140423 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140507 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140804 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140807 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140903 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141022 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141027 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5641643 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |