CA2154153C - Process for the production of plasticizer and polyol esters - Google Patents
Process for the production of plasticizer and polyol esters Download PDFInfo
- Publication number
- CA2154153C CA2154153C CA002154153A CA2154153A CA2154153C CA 2154153 C CA2154153 C CA 2154153C CA 002154153 A CA002154153 A CA 002154153A CA 2154153 A CA2154153 A CA 2154153A CA 2154153 C CA2154153 C CA 2154153C
- Authority
- CA
- Canada
- Prior art keywords
- water
- process according
- alcohol
- reaction vessel
- acid
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 74
- 230000008569 process Effects 0.000 title claims abstract description 63
- -1 polyol esters Chemical class 0.000 title description 33
- 229920005862 polyol Polymers 0.000 title description 24
- 239000004014 plasticizer Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 196
- 238000006243 chemical reaction Methods 0.000 claims abstract description 188
- 239000002253 acid Substances 0.000 claims abstract description 65
- 238000005886 esterification reaction Methods 0.000 claims abstract description 57
- 230000032050 esterification Effects 0.000 claims abstract description 51
- 238000009835 boiling Methods 0.000 claims abstract description 36
- 239000011541 reaction mixture Substances 0.000 claims abstract description 29
- 238000002156 mixing Methods 0.000 claims abstract description 27
- 150000007513 acids Chemical class 0.000 claims abstract description 22
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims description 49
- 239000003054 catalyst Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 26
- 238000001914 filtration Methods 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 23
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims description 21
- 230000007062 hydrolysis Effects 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 18
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000007792 addition Methods 0.000 claims description 16
- 238000004064 recycling Methods 0.000 claims description 16
- 239000010936 titanium Substances 0.000 claims description 16
- 235000017550 sodium carbonate Nutrition 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000006386 neutralization reaction Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- 229910052726 zirconium Inorganic materials 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 9
- 239000004927 clay Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000003463 adsorbent Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 229940059574 pentaerithrityl Drugs 0.000 claims description 6
- 229910052718 tin Inorganic materials 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 230000003134 recirculating effect Effects 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 238000009834 vaporization Methods 0.000 claims description 2
- 230000008016 vaporization Effects 0.000 claims description 2
- 241000490229 Eucephalus Species 0.000 claims 1
- 238000010923 batch production Methods 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 238000003260 vortexing Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 24
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 235000019441 ethanol Nutrition 0.000 description 41
- 230000007306 turnover Effects 0.000 description 38
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 20
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 18
- 239000012035 limiting reagent Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 12
- 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 12
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 11
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 11
- 239000004440 Isodecyl alcohol Substances 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000013461 design Methods 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QFJPQEKQIKSNBU-UHFFFAOYSA-M [Ti]O Chemical compound [Ti]O QFJPQEKQIKSNBU-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 125000005591 trimellitate group Chemical group 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 229960005082 etohexadiol Drugs 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000005498 phthalate group Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 238000012821 model calculation Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- NDSXSCFKIAPKJG-UHFFFAOYSA-N CC(C)O[Ti] Chemical compound CC(C)O[Ti] NDSXSCFKIAPKJG-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 238000013178 mathematical model Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ZICLWBMRDQUIDO-UHFFFAOYSA-N monoisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(O)=O ZICLWBMRDQUIDO-UHFFFAOYSA-N 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- QPKZTOIUUGTCNF-UHFFFAOYSA-N pentacosane-1,25-diol Chemical compound OCCCCCCCCCCCCCCCCCCCCCCCCCO QPKZTOIUUGTCNF-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- BWRBVBFLFQKBPT-UHFFFAOYSA-N (2-nitrophenyl)methanol Chemical compound OCC1=CC=CC=C1[N+]([O-])=O BWRBVBFLFQKBPT-UHFFFAOYSA-N 0.000 description 1
- UALGDSCLDIEGCQ-ZPUQHVIOSA-N (2e,4e)-hexa-2,4-diene-1,6-diol Chemical compound OC\C=C\C=C\CO UALGDSCLDIEGCQ-ZPUQHVIOSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- MHZOFWFRCQRXIH-UHFFFAOYSA-N (4-benzylphenyl)methanol Chemical compound C1=CC(CO)=CC=C1CC1=CC=CC=C1 MHZOFWFRCQRXIH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 description 1
- MCXWYHQIUABDRL-UHFFFAOYSA-N 2-(4-ethyloctyl)benzenesulfonic acid Chemical compound CCCCC(CC)CCCC1=CC=CC=C1S(O)(=O)=O MCXWYHQIUABDRL-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- IDDYNNYMUPHFMO-UHFFFAOYSA-N 2-Keto-n-heptylic acid Chemical compound CCCCCC(=O)C(O)=O IDDYNNYMUPHFMO-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- UAZLASMTBCLJKO-UHFFFAOYSA-N 2-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UAZLASMTBCLJKO-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- XATFRRKBXKIIRM-UHFFFAOYSA-N 2-heptylbenzenesulfonic acid Chemical compound CCCCCCCC1=CC=CC=C1S(O)(=O)=O XATFRRKBXKIIRM-UHFFFAOYSA-N 0.000 description 1
- SYSFRXFRWRDPIJ-UHFFFAOYSA-N 2-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=CC=C1S(O)(=O)=O SYSFRXFRWRDPIJ-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 description 1
- JBFDBSZCFDASAE-UHFFFAOYSA-N 2-oxodecanoic acid Chemical compound CCCCCCCCC(=O)C(O)=O JBFDBSZCFDASAE-UHFFFAOYSA-N 0.000 description 1
- GPPUPQFYDYLTIY-UHFFFAOYSA-N 2-oxooctanoic acid Chemical compound CCCCCCC(=O)C(O)=O GPPUPQFYDYLTIY-UHFFFAOYSA-N 0.000 description 1
- PVXSFEGIHWMAOD-UHFFFAOYSA-N 2-tridecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O PVXSFEGIHWMAOD-UHFFFAOYSA-N 0.000 description 1
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 1
- JJCKHVUTVOPLBV-UHFFFAOYSA-N 3-Methylbenzyl alcohol Chemical compound CC1=CC=CC(CO)=C1 JJCKHVUTVOPLBV-UHFFFAOYSA-N 0.000 description 1
- XOPJXOUQPWIFEW-UHFFFAOYSA-N 3-methyldodecane-1-sulfonic acid Chemical compound CCCCCCCCCC(C)CCS(O)(=O)=O XOPJXOUQPWIFEW-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- UDTHXSLCACXSKA-UHFFFAOYSA-N 3-tetradecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCC1=CC=CC(S(O)(=O)=O)=C1 UDTHXSLCACXSKA-UHFFFAOYSA-N 0.000 description 1
- AZMGXRQYHFTABA-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1C AZMGXRQYHFTABA-UHFFFAOYSA-N 0.000 description 1
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 1
- WPTFZDRBJGXAMT-UHFFFAOYSA-N 4-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 WPTFZDRBJGXAMT-UHFFFAOYSA-N 0.000 description 1
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 description 1
- 101150010353 Ascl1 gene Proteins 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- IMFVDBUUZFZPOI-UHFFFAOYSA-J C(C)(=O)[O-].O[Ti+3].C(C)(=O)[O-].C(C)(=O)[O-] Chemical compound C(C)(=O)[O-].O[Ti+3].C(C)(=O)[O-].C(C)(=O)[O-] IMFVDBUUZFZPOI-UHFFFAOYSA-J 0.000 description 1
- SENWYOSJEOOKBX-UHFFFAOYSA-J C(CCC)(=O)[O-].O[Ti+3].C(CCC)(=O)[O-].C(CCC)(=O)[O-] Chemical compound C(CCC)(=O)[O-].O[Ti+3].C(CCC)(=O)[O-].C(CCC)(=O)[O-] SENWYOSJEOOKBX-UHFFFAOYSA-J 0.000 description 1
- BMMFMORLUFVBHA-UHFFFAOYSA-J C(CCCC)(=O)[O-].O[Ti+3].C(CCCC)(=O)[O-].C(CCCC)(=O)[O-] Chemical compound C(CCCC)(=O)[O-].O[Ti+3].C(CCCC)(=O)[O-].C(CCCC)(=O)[O-] BMMFMORLUFVBHA-UHFFFAOYSA-J 0.000 description 1
- XBGFWLBNWHSYTL-UHFFFAOYSA-J C(CCCCC)(=O)[O-].O[Ti+3].C(CCCCC)(=O)[O-].C(CCCCC)(=O)[O-] Chemical compound C(CCCCC)(=O)[O-].O[Ti+3].C(CCCCC)(=O)[O-].C(CCCCC)(=O)[O-] XBGFWLBNWHSYTL-UHFFFAOYSA-J 0.000 description 1
- RMMYAJPMYFXMGB-UHFFFAOYSA-J C(CCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCC)(=O)[O-].C(CCCCCCC)(=O)[O-] Chemical compound C(CCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCC)(=O)[O-].C(CCCCCCC)(=O)[O-] RMMYAJPMYFXMGB-UHFFFAOYSA-J 0.000 description 1
- UMAAHBKENSTORN-UHFFFAOYSA-J C(CCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCC)(=O)[O-].C(CCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCC)(=O)[O-].C(CCCCCCCCC)(=O)[O-] UMAAHBKENSTORN-UHFFFAOYSA-J 0.000 description 1
- ZIYNBPCGUQEVQD-UHFFFAOYSA-J C(CCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] ZIYNBPCGUQEVQD-UHFFFAOYSA-J 0.000 description 1
- KLKRBQNHBMGQKL-UHFFFAOYSA-J C(CCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCC)(=O)[O-] KLKRBQNHBMGQKL-UHFFFAOYSA-J 0.000 description 1
- PYQVLQFDBSZWDO-UHFFFAOYSA-J C(CCCCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCC)(=O)[O-] PYQVLQFDBSZWDO-UHFFFAOYSA-J 0.000 description 1
- JFXKHDYTACRKLL-UHFFFAOYSA-J C(CCCCCCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].O[Ti+3].C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-] JFXKHDYTACRKLL-UHFFFAOYSA-J 0.000 description 1
- OGLVSEIKVXZAOV-UHFFFAOYSA-K CC(C)O[Ti+3].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O Chemical compound CC(C)O[Ti+3].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O OGLVSEIKVXZAOV-UHFFFAOYSA-K 0.000 description 1
- IFABSGXQDMSHTA-UHFFFAOYSA-K CC(C)O[Ti+3].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O Chemical compound CC(C)O[Ti+3].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O IFABSGXQDMSHTA-UHFFFAOYSA-K 0.000 description 1
- SPZKQHASENTKQM-UHFFFAOYSA-K CC(C)O[Ti+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O Chemical compound CC(C)O[Ti+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O SPZKQHASENTKQM-UHFFFAOYSA-K 0.000 description 1
- FCGLPKMFWNOHTB-UHFFFAOYSA-K CC(C)O[Ti+3].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O Chemical compound CC(C)O[Ti+3].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O FCGLPKMFWNOHTB-UHFFFAOYSA-K 0.000 description 1
- DMFOZPIZDJIXDZ-UHFFFAOYSA-K CCCCO[Ti+3].CCCCCC([O-])=O.CCCCCC([O-])=O.CCCCCC([O-])=O Chemical compound CCCCO[Ti+3].CCCCCC([O-])=O.CCCCCC([O-])=O.CCCCCC([O-])=O DMFOZPIZDJIXDZ-UHFFFAOYSA-K 0.000 description 1
- QPVIOFJAAKUXDC-UHFFFAOYSA-K C[O-].CC(=O)O[Ti+](OC(C)=O)OC(C)=O Chemical compound C[O-].CC(=O)O[Ti+](OC(C)=O)OC(C)=O QPVIOFJAAKUXDC-UHFFFAOYSA-K 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid group Chemical group C(\C(\C)=C/C)(=O)O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- ZRHOFLXFAAEXEE-UHFFFAOYSA-J butanoate;titanium(4+) Chemical compound [Ti+4].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O ZRHOFLXFAAEXEE-UHFFFAOYSA-J 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- SUSAGCZZQKACKE-UHFFFAOYSA-N cyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC1C(O)=O SUSAGCZZQKACKE-UHFFFAOYSA-N 0.000 description 1
- WYHYNUWZLKTEEY-UHFFFAOYSA-N cyclobutane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C1 WYHYNUWZLKTEEY-UHFFFAOYSA-N 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- GOWHHUDNXNDUAS-UHFFFAOYSA-N cyclohexa-1,3-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CCC1 GOWHHUDNXNDUAS-UHFFFAOYSA-N 0.000 description 1
- BQYOGZXCESFTRX-UHFFFAOYSA-N cyclohexa-1,3-diene-1,4-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)CC1 BQYOGZXCESFTRX-UHFFFAOYSA-N 0.000 description 1
- DTGRIEIJTWNZQF-UHFFFAOYSA-N cyclohexane-1,2,3,4,5,6-hexacarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C(C(O)=O)C(C(O)=O)C1C(O)=O DTGRIEIJTWNZQF-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LRBBIFXICMMTOW-UHFFFAOYSA-N dodecan-6-ol Chemical compound CCCCCCC(O)CCCCC LRBBIFXICMMTOW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WPBLEHOHTCLADT-UHFFFAOYSA-N dodecane-3-sulfonic acid Chemical compound CCCCCCCCCC(CC)S(O)(=O)=O WPBLEHOHTCLADT-UHFFFAOYSA-N 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 108010052322 limitin Proteins 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- NARPMWPOFWHFDX-UHFFFAOYSA-N methanetrisulfonic acid Chemical compound OS(=O)(=O)C(S(O)(=O)=O)S(O)(=O)=O NARPMWPOFWHFDX-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical class C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- UELKEKWDSAUZCA-UHFFFAOYSA-N nonadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCCS(O)(=O)=O UELKEKWDSAUZCA-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- QVJVMWFSHIRKPH-UHFFFAOYSA-N octa-2,4-diene-1,8-diol Chemical compound OCCCC=CC=CCO QVJVMWFSHIRKPH-UHFFFAOYSA-N 0.000 description 1
- CACRRXGTWZXOAU-UHFFFAOYSA-N octadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCS(O)(=O)=O CACRRXGTWZXOAU-UHFFFAOYSA-N 0.000 description 1
- BQZVDHLPECSTCE-UHFFFAOYSA-K octanoate propan-2-olate titanium(4+) Chemical compound CC(C)O[Ti+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O BQZVDHLPECSTCE-UHFFFAOYSA-K 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- ZBPYFGWSQQFVCJ-UHFFFAOYSA-N pentadecane-1,15-diol Chemical compound OCCCCCCCCCCCCCCCO ZBPYFGWSQQFVCJ-UHFFFAOYSA-N 0.000 description 1
- TWBKZBJAVASNII-UHFFFAOYSA-N pentadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCS(O)(=O)=O TWBKZBJAVASNII-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PHSGEKAEADHCHA-UHFFFAOYSA-N propan-2-yl hexadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCC(=O)OOC(C)C PHSGEKAEADHCHA-UHFFFAOYSA-N 0.000 description 1
- DJCQXOQOBXPZLC-UHFFFAOYSA-N propan-2-yl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(C)C DJCQXOQOBXPZLC-UHFFFAOYSA-N 0.000 description 1
- MGNVWUDMMXZUDI-UHFFFAOYSA-N propane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CCCS(O)(=O)=O MGNVWUDMMXZUDI-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MYOWBHNETUSQPA-UHFFFAOYSA-N tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCS(O)(=O)=O MYOWBHNETUSQPA-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid group Chemical group C(\C(\C)=C\C)(=O)O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 1
- GTSMGKYOGFOSAR-UHFFFAOYSA-N tridecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCS(O)(=O)=O GTSMGKYOGFOSAR-UHFFFAOYSA-N 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1868—Stationary reactors having moving elements inside resulting in a loop-type movement
- B01J19/1875—Stationary reactors having moving elements inside resulting in a loop-type movement internally, i.e. the mixture circulating inside the vessel such that the upwards stream is separated physically from the downwards stream(s)
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00761—Details of the reactor
- B01J2219/00763—Baffles
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/006,228 US5324853A (en) | 1993-01-19 | 1993-01-19 | Process for the production of plasticizer and polyolesters |
| US006,228 | 1993-01-19 | ||
| PCT/US1994/000767 WO1994017028A1 (en) | 1993-01-19 | 1994-01-19 | Process for the production of plasticizer and polyol esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2154153A1 CA2154153A1 (en) | 1994-08-04 |
| CA2154153C true CA2154153C (en) | 2004-08-10 |
Family
ID=21719891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002154153A Expired - Fee Related CA2154153C (en) | 1993-01-19 | 1994-01-19 | Process for the production of plasticizer and polyol esters |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5324853A (OSRAM) |
| EP (1) | EP0680463B2 (OSRAM) |
| JP (1) | JPH08505879A (OSRAM) |
| KR (1) | KR100284475B1 (OSRAM) |
| CN (1) | CN1046265C (OSRAM) |
| AU (1) | AU675294B2 (OSRAM) |
| BR (1) | BR9405659A (OSRAM) |
| CA (1) | CA2154153C (OSRAM) |
| DE (1) | DE69410988T3 (OSRAM) |
| ES (1) | ES2119172T5 (OSRAM) |
| MY (1) | MY110495A (OSRAM) |
| SG (1) | SG48306A1 (OSRAM) |
| TW (1) | TW268940B (OSRAM) |
| WO (1) | WO1994017028A1 (OSRAM) |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5532405A (en) * | 1994-04-29 | 1996-07-02 | Exxon Chemical Patents Inc. | Preparation of plasticizer or polyol esters by the staged addition of the lower boiling point reactant |
| US5534652A (en) * | 1994-10-18 | 1996-07-09 | Exxon Chemical Patents Inc. (Ecpi) | Preparation of plasticizer esters from phthalic anhydride residue |
| JP3944251B2 (ja) * | 1995-03-22 | 2007-07-11 | 松本油脂製薬株式会社 | エステル精製方法 |
| US6177387B1 (en) | 1996-08-30 | 2001-01-23 | Exxon Chemical Patents Inc | Reduced odor and high stability aircraft turbine oil base stock |
| CN1249740A (zh) * | 1997-02-28 | 2000-04-05 | 新日本理化株式会社 | 对羟基苯甲酸酯,包含其的增塑剂、聚酰胺树脂组合物和模塑制品 |
| US5898077A (en) * | 1997-10-07 | 1999-04-27 | Matsumoto Yushi-Seiyaku Co., Ltd. | Process for preparation of an ester |
| NZ504648A (en) * | 1997-11-24 | 2002-02-01 | Energea Umwelttechnologie Gmbh | Method and equipment for producing fatty acid methyl ester to produce diesel fuel where the fatty acids are transesterified to fatty acid methyl ester |
| DE10056179A1 (de) * | 2000-11-13 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von Estern mehrbasiger Säuren |
| US6906164B2 (en) * | 2000-12-07 | 2005-06-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| KR100426229B1 (ko) * | 2001-01-05 | 2004-04-08 | 주식회사 엘지화학 | 폴리염화비닐 수지용 트리메틸올프로판 에스테르 가소제조성물 |
| AT504727A1 (de) * | 2002-04-12 | 2008-07-15 | Energea Umwelttechnologie Gmbh | Verfahren und anlage zur veresterung von fettsäuren |
| GB0320206D0 (en) * | 2003-08-29 | 2003-10-01 | Exxonmobil Chem Patents Inc | Improvements in or relating to plasticiser |
| JP2006154384A (ja) * | 2004-11-30 | 2006-06-15 | Konica Minolta Opto Inc | 位相差フィルム、及びそれを用いた偏光板、表示装置 |
| JP2006182606A (ja) * | 2004-12-28 | 2006-07-13 | Miyoshi Oil & Fat Co Ltd | セメント混和剤及びセメント組成物 |
| CN1300092C (zh) * | 2005-03-09 | 2007-02-14 | 贵州宏福实业开发有限总公司 | 多元醇脂肪酸酯的生产方法 |
| US7919649B2 (en) * | 2005-05-27 | 2011-04-05 | Exxonmobile Chemical Patents Inc. | Plasticiser esters |
| KR20080018961A (ko) * | 2005-06-24 | 2008-02-28 | 헥시온 스페셜티 케미컬스 리서치 벨기에 에스.에이. | 3차 알킬이 치환된 산을 이용한 폴리올의 에스테르화 방법 |
| US7291748B2 (en) * | 2005-07-28 | 2007-11-06 | Basf Corporation | C10/C7 ester mixtures based on 2-propylheptanol |
| JP2007031383A (ja) * | 2005-07-28 | 2007-02-08 | Mitsubishi Chemicals Corp | テレフタル酸ジエステルの製造方法 |
| US7453008B2 (en) * | 2005-08-23 | 2008-11-18 | Lg Chem Ltd. | Synthetic method of glycol diesters from reaction of glycol monoesters and linear aliphatic carboxylic acids |
| US20070087085A1 (en) * | 2005-10-17 | 2007-04-19 | Bunge Oils, Inc. | Protein-containing food product and coating for a food product and method of making same |
| US20080113067A1 (en) * | 2005-10-17 | 2008-05-15 | Monoj Sarma | Protein-Containing Food Product and Coating for a Food Product and Method of Making Same |
| US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
| US20080044324A1 (en) * | 2006-08-16 | 2008-02-21 | Agency For Science, Technology And Research | Recirculating reactor |
| US20080139780A1 (en) * | 2006-12-07 | 2008-06-12 | Debruin Bruce Roger | Polyester production system employing short residence time esterification |
| US7943094B2 (en) | 2006-12-07 | 2011-05-17 | Grupo Petrotemex, S.A. De C.V. | Polyester production system employing horizontally elongated esterification vessel |
| US7649109B2 (en) * | 2006-12-07 | 2010-01-19 | Eastman Chemical Company | Polyester production system employing recirculation of hot alcohol to esterification zone |
| KR100919930B1 (ko) | 2007-01-10 | 2009-10-07 | 주식회사 엘지화학 | 내이행성이 우수한 고분자 가소제, 이의 제조방법 및 이를포함하는 고분자 수지 조성물 |
| US7892498B2 (en) | 2007-03-08 | 2011-02-22 | Eastman Chemical Company | Polyester production system employing an unagitated esterification reactor |
| US7863477B2 (en) | 2007-03-08 | 2011-01-04 | Eastman Chemical Company | Polyester production system employing hot paste to esterification zone |
| JP2010520902A (ja) * | 2007-03-13 | 2010-06-17 | エクソンモービル・ケミカル・パテンツ・インク | エステルの製造方法 |
| ATE517077T1 (de) * | 2007-03-13 | 2011-08-15 | Exxonmobil Chem Patents Inc | Chargenweise veresterung |
| EP2155654B1 (en) * | 2007-03-13 | 2012-02-22 | ExxonMobil Chemical Patents Inc. | Improvement in ester production |
| US7872089B2 (en) | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Multi-level tubular reactor with internal tray |
| US7868130B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Multi-level tubular reactor with vertically spaced segments |
| US7868129B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Sloped tubular reactor with spaced sequential trays |
| US7858730B2 (en) * | 2007-07-12 | 2010-12-28 | Eastman Chemical Company | Multi-level tubular reactor with dual headers |
| US7872090B2 (en) | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Reactor system with optimized heating and phase separation |
| US7829653B2 (en) | 2007-07-12 | 2010-11-09 | Eastman Chemical Company | Horizontal trayed reactor |
| US7847053B2 (en) | 2007-07-12 | 2010-12-07 | Eastman Chemical Company | Multi-level tubular reactor with oppositely extending segments |
| US7842777B2 (en) | 2007-07-12 | 2010-11-30 | Eastman Chemical Company | Sloped tubular reactor with divided flow |
| KR100943027B1 (ko) * | 2007-11-09 | 2010-02-18 | 주식회사 거영 | 디트리데실프탈산 제조방법 |
| US7834109B2 (en) * | 2007-12-07 | 2010-11-16 | Eastman Chemical Company | System for producing low impurity polyester |
| BRPI0915051B1 (pt) | 2008-05-14 | 2021-04-13 | Council Of Scientific & Industrial Research | Óleo básico lubrificante, ésteres de poliol de ácidos graxos de cadeia média e processo para preparação dos mesmos |
| US7674931B1 (en) | 2008-12-15 | 2010-03-09 | Eastman Chemical Company | Method for producing 2,2,4-trimethyl-1,3-pentanediol di-2-ethylhexanoate |
| EP2379482B1 (de) | 2008-12-16 | 2015-08-26 | Basf Se | Herstellung von carbonsäureestern unter strippen mit alkohol-dampf |
| DE102009048771A1 (de) * | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048772A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048773A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
| DE102009048775A1 (de) * | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048774A1 (de) | 2009-10-08 | 2011-04-28 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
| EP2496654B1 (de) | 2009-11-05 | 2014-04-02 | Basf Se | Kleb- und dichtstoffe enthaltend ester auf basis von 2-propylheptanol |
| DE102010027458A1 (de) * | 2010-07-17 | 2012-01-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
| US9725401B2 (en) | 2010-08-25 | 2017-08-08 | Exxonmobil Chemical Patents Inc. | Processes for the production of esters |
| EP2655511B1 (de) | 2010-12-23 | 2016-04-06 | INEOS Styrolution Europe GmbH | Thermoplastische elastomer-zusammensetzung und verfahren zu deren herstellung |
| CN102773048B (zh) * | 2011-05-09 | 2017-06-06 | 波利玛利欧洲股份公司 | 生产环己酮肟的氨肟化反应器 |
| US20140343204A1 (en) | 2011-08-15 | 2014-11-20 | Didier Naert | Esters, Hydrogenated Derivatives Thereof, and Processes for Producing the Same |
| WO2013143825A1 (en) | 2012-03-30 | 2013-10-03 | Exxonmobil Chemical Patents Inc. | Esterification process |
| US9481628B2 (en) | 2012-03-30 | 2016-11-01 | Exxonmobil Chemical Patents Inc. | Esterification process |
| US20150175774A1 (en) * | 2012-08-09 | 2015-06-25 | Nok Corporation | Nbr composition |
| DE102012018207A1 (de) | 2012-09-14 | 2014-03-20 | Oxea Gmbh | Verfahren zur Herstelluna von Polyolestern |
| CN102863332B (zh) * | 2012-09-27 | 2014-08-06 | 昆明理工大学 | 一种有机琥珀及其制备方法 |
| CN103130640B (zh) * | 2013-01-16 | 2015-06-10 | 宁波东来化工有限公司 | 一种制备1,2-环己烷二甲酸二癸酯的装置及其方法 |
| DE102013015289A1 (de) | 2013-09-14 | 2015-03-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
| DE102013018456B4 (de) | 2013-11-02 | 2019-01-24 | Oxea Gmbh | Verfahren zur Gewinnung von mit Polyolestern angereicherten Produktströmen aus den Nebenströmen der Polyolesterherstellung |
| CA2932240A1 (en) | 2013-12-06 | 2015-06-11 | Basf Se | Softener composition which contains tetrahydrofuran derivatives and 1,2-cyclohexane dicarboxylic acid esters |
| CN103739492A (zh) * | 2013-12-31 | 2014-04-23 | 河南庆安化工高科技股份有限公司 | 一种制备环己烷邻二甲酸二高碳醇酯的方法 |
| ES2690081T3 (es) | 2014-01-09 | 2018-11-19 | Basf Se | Composición plastificante que contiene derivados de furano y ésteres de ácido 1,2-ciclohexano dicarboxílico |
| DE102015207291A1 (de) | 2014-04-24 | 2016-03-10 | Basf Se | Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält |
| TW201605945A (zh) | 2014-07-08 | 2016-02-16 | 巴斯夫歐洲公司 | 包含二羧酸的酯及１，２－環己烷二羧酸的酯之模製化合物 |
| TW201609628A (zh) | 2014-07-08 | 2016-03-16 | 巴斯夫歐洲公司 | 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物 |
| CN107074857A (zh) | 2014-08-18 | 2017-08-18 | 巴斯夫欧洲公司 | 用于制备结晶有机半导体材料的方法 |
| TWI706979B (zh) | 2014-08-19 | 2020-10-11 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| TWI686444B (zh) | 2014-09-04 | 2020-03-01 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| CN107428990B (zh) | 2015-01-30 | 2019-07-12 | 巴斯夫欧洲公司 | 包含聚合二羧酸酯及对苯二甲酸二烷基酯的增塑剂组合物 |
| CN106045857A (zh) * | 2015-04-24 | 2016-10-26 | 中国科学院大连化学物理研究所 | 一种二环己基甲酸二元醇酯增塑剂的制备方法 |
| WO2016193134A1 (de) | 2015-05-29 | 2016-12-08 | Basf Se | Verfahren zur herstellung cyclischer ester |
| WO2017055432A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und terephthalsäuredialkylester enthält |
| ES2743975T5 (es) | 2015-09-30 | 2023-05-10 | Basf Se | Composición de plastificante que contiene ésteres de ácido dicarboxílico poliméricos y ésteres de ácido 1,2-diclohexandicarboxílico |
| CN108137851B (zh) | 2015-09-30 | 2020-10-09 | 巴斯夫欧洲公司 | 包含聚合二羧酸酯和二羧酸二酯的增塑剂组合物 |
| CN105254501A (zh) * | 2015-10-23 | 2016-01-20 | 淮阴师范学院 | 环己烷-1,2-二甲酸二异壬酯的制备方法 |
| EP3178908A1 (en) | 2015-12-11 | 2017-06-14 | Basf Se | The use of 2,5-furandicarboxylic acid esters as lubricants |
| EP3405518B1 (de) | 2016-01-20 | 2019-11-06 | Basf Se | Weichmacher-zusammensetzung, die aliphatische dicarbonsäureester und diester, die unter 1,2-cyclohexandicarbonsäureestern und terephthalsäureestern ausgewählt sind, enthält |
| PL3433309T3 (pl) | 2016-03-23 | 2020-11-16 | Basf Se | Kompozycja polimerowa, zawierająca diester cykloalkilowo-alkilowy kwasu dikarboksylowego jako plastyfikator |
| WO2018024591A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| EP3491053A1 (de) | 2016-08-01 | 2019-06-05 | Basf Se | Weichmacher-zusammensetzung |
| EP3491054A1 (de) | 2016-08-01 | 2019-06-05 | Basf Se | Weichmacher-zusammensetzung |
| WO2018024597A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| KR102641380B1 (ko) * | 2016-11-11 | 2024-02-28 | 오씨아이 주식회사 | 테레프탈산계 에스터 화합물을 정제하는 방법 |
| WO2019185409A1 (de) | 2018-03-29 | 2019-10-03 | Basf Se | Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung |
| EP3747860B1 (de) | 2019-06-04 | 2023-07-26 | Basf Se | Neue weichmacher auf cyclohexanon-basis |
| KR102669652B1 (ko) | 2019-09-19 | 2024-05-28 | 주식회사 엘지화학 | 에스터화 생성물의 중화/수분리 장치 및 에스터화 생성물의 중화/수분리 방법 |
| KR102614264B1 (ko) | 2019-09-19 | 2023-12-18 | 주식회사 엘지화학 | 에스터화 생성물의 중화/수분리조 및 에스터화 생성물의 중화/수분리 방법 |
| KR102528326B1 (ko) * | 2020-02-14 | 2023-05-02 | 한화솔루션 주식회사 | 에스테르계 화합물의 제조방법 |
| KR20220067352A (ko) | 2020-11-17 | 2022-05-24 | 주식회사 엘지화학 | 디에스터계 물질의 제조방법 |
| EP4638411A1 (de) | 2022-12-21 | 2025-10-29 | Basf Se | Weichmacher |
| WO2024133358A1 (de) | 2022-12-21 | 2024-06-27 | Basf Se | Weichmacher-verbindung |
| WO2024153687A1 (de) | 2023-01-19 | 2024-07-25 | Basf Se | Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern |
| WO2024256670A1 (de) | 2023-06-15 | 2024-12-19 | Basf Se | Weichmacher-zusammensetzung |
| WO2025125093A1 (de) | 2023-12-14 | 2025-06-19 | Basf Se | Weichmacher auf basis von sebacinsäure |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2411136A (en) * | 1942-03-21 | 1946-11-12 | Monsanto Chemicals | Esterification reactions |
| US2494133A (en) * | 1946-09-07 | 1950-01-10 | American Cyanamid Co | Method of neutralizing and completely removing salts before distilling crude high-boiling esters |
| US2628249A (en) * | 1951-01-03 | 1953-02-10 | Pittsburgh Coke & Chemical Co | Esterification process |
| US3056818A (en) * | 1955-10-13 | 1962-10-02 | Goodrich Co B F | Titanium and zirconium esterification catalysts |
| IT778269A (OSRAM) * | 1964-01-25 | |||
| US3519054A (en) * | 1969-01-06 | 1970-07-07 | Colgate Palmolive Co | Process for producing a particulate product |
| GB1299078A (en) * | 1969-04-30 | 1972-12-06 | Ici Ltd | Distillation process |
| GB1426057A (en) * | 1972-04-24 | 1976-02-25 | Ici Ltd | Production of esters |
| GB1565663A (en) * | 1977-05-18 | 1980-04-23 | Bp Chemical Ltd | Production of esters in the presence of amphoteric catalysts and oxalic acid |
| US4241216A (en) * | 1979-01-02 | 1980-12-23 | Basf Wyandotte Corporation | Phthalic acid diester preparation with waste stream purification and recycle |
| JPS55130937A (en) * | 1979-03-29 | 1980-10-11 | Sekisui Chem Co Ltd | Preparation of ester |
| EP0342357A3 (de) * | 1988-04-22 | 1990-03-28 | Henkel Kommanditgesellschaft auf Aktien | Vorrichtung, Anwendung und Verfahren zum diskontinuierlichen Führen einer Gleichgewichtsreaktion |
-
1993
- 1993-01-19 US US08/006,228 patent/US5324853A/en not_active Expired - Lifetime
-
1994
- 1994-01-19 MY MYPI94000144A patent/MY110495A/en unknown
- 1994-01-19 JP JP6517210A patent/JPH08505879A/ja not_active Ceased
- 1994-01-19 WO PCT/US1994/000767 patent/WO1994017028A1/en not_active Ceased
- 1994-01-19 CN CN94191230A patent/CN1046265C/zh not_active Expired - Fee Related
- 1994-01-19 EP EP94906704A patent/EP0680463B2/en not_active Expired - Lifetime
- 1994-01-19 BR BR9405659A patent/BR9405659A/pt not_active IP Right Cessation
- 1994-01-19 CA CA002154153A patent/CA2154153C/en not_active Expired - Fee Related
- 1994-01-19 DE DE69410988T patent/DE69410988T3/de not_active Expired - Lifetime
- 1994-01-19 SG SG1996008794A patent/SG48306A1/en unknown
- 1994-01-19 AU AU60322/94A patent/AU675294B2/en not_active Ceased
- 1994-01-19 KR KR1019950702934A patent/KR100284475B1/ko not_active Expired - Fee Related
- 1994-01-19 ES ES94906704T patent/ES2119172T5/es not_active Expired - Lifetime
- 1994-03-17 TW TW083102335A patent/TW268940B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69410988D1 (de) | 1998-07-16 |
| AU675294B2 (en) | 1997-01-30 |
| ES2119172T3 (es) | 1998-10-01 |
| CN1118158A (zh) | 1996-03-06 |
| TW268940B (OSRAM) | 1996-01-21 |
| MY110495A (en) | 1998-06-30 |
| KR960700216A (ko) | 1996-01-19 |
| BR9405659A (pt) | 1995-11-14 |
| KR100284475B1 (ko) | 2001-04-02 |
| SG48306A1 (en) | 1998-04-17 |
| WO1994017028A1 (en) | 1994-08-04 |
| EP0680463B2 (en) | 2001-12-19 |
| EP0680463B1 (en) | 1998-06-10 |
| EP0680463A1 (en) | 1995-11-08 |
| US5324853A (en) | 1994-06-28 |
| DE69410988T2 (de) | 1998-12-10 |
| DE69410988T3 (de) | 2002-06-27 |
| ES2119172T5 (es) | 2002-07-01 |
| CA2154153A1 (en) | 1994-08-04 |
| AU6032294A (en) | 1994-08-15 |
| CN1046265C (zh) | 1999-11-10 |
| JPH08505879A (ja) | 1996-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2154153C (en) | Process for the production of plasticizer and polyol esters | |
| AU637595B2 (en) | Process and apparatus | |
| KR101338617B1 (ko) | 가소제 에스터 | |
| US6355817B1 (en) | Optimized catalyst addition to enhance esterification catalyst performance | |
| CA2525898C (en) | Apparatus for and method of producing aromatic carboxylic acids | |
| US3787479A (en) | Process for the continuous transesterification of dicarboxylic acid alkyl esters with diols | |
| US5532405A (en) | Preparation of plasticizer or polyol esters by the staged addition of the lower boiling point reactant | |
| US2644009A (en) | Continuous esterification process | |
| KR101130871B1 (ko) | 파이프 반응기를 이용한 폴리에스터 제조 방법 | |
| CN103387495B (zh) | 连续制备羧酸酯的方法 | |
| CN222872124U (zh) | 连续法合成c8-13醇苯多元酸酯的反应装置 | |
| TW304942B (OSRAM) | ||
| JP7331302B2 (ja) | ジエステル系化合物の製造方法 | |
| CA2956306C (en) | Process comprising emulsification and agglomeration in the workup of crude esters | |
| CN102908956B (zh) | 一种酯化反应器及马来酸二甲酯的生产方法 | |
| US10822297B2 (en) | Method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst | |
| JP2022553555A (ja) | フタレート系化合物の水素化方法 | |
| CN105037144A (zh) | 2-乙基己酸双三羟甲基丙烷酯及其一种生产方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |