BR112015009393B1 - método de preparação de ésteres - Google Patents
método de preparação de ésteres Download PDFInfo
- Publication number
- BR112015009393B1 BR112015009393B1 BR112015009393-0A BR112015009393A BR112015009393B1 BR 112015009393 B1 BR112015009393 B1 BR 112015009393B1 BR 112015009393 A BR112015009393 A BR 112015009393A BR 112015009393 B1 BR112015009393 B1 BR 112015009393B1
- Authority
- BR
- Brazil
- Prior art keywords
- acid
- carbonate
- alcohol
- reaction
- esters
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 51
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 47
- 150000007524 organic acids Chemical class 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 32
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 31
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 27
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 26
- 150000005690 diesters Chemical class 0.000 claims description 26
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 10
- 230000001476 alcoholic effect Effects 0.000 claims description 10
- 235000011090 malic acid Nutrition 0.000 claims description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 9
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 9
- 239000001630 malic acid Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 8
- 150000005691 triesters Chemical class 0.000 claims description 8
- 235000015165 citric acid Nutrition 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 6
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 glucaric Chemical compound 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- ODBLHEXUDAPZAU-FONMRSAGSA-N Isocitric acid Natural products OC(=O)[C@@H](O)[C@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-FONMRSAGSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 229940091181 aconitic acid Drugs 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 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
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 claims description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 2
- 229940005605 valeric acid Drugs 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 235000005985 organic acids Nutrition 0.000 abstract description 10
- 230000008901 benefit Effects 0.000 abstract description 6
- 238000000605 extraction Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000009413 insulation Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000005886 esterification reaction Methods 0.000 description 41
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 32
- 230000032050 esterification Effects 0.000 description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
- 229940040102 levulinic acid Drugs 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 150000001735 carboxylic acids Chemical class 0.000 description 13
- 235000011044 succinic acid Nutrition 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000001384 succinic acid Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 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
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 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 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006063 methoxycarbonylation reaction Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
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- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
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- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
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- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000001404 mediated effect Effects 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261719537P | 2012-10-29 | 2012-10-29 | |
| US61/719,537 | 2012-10-29 | ||
| PCT/US2013/064458 WO2014070415A1 (en) | 2012-10-29 | 2013-10-11 | Alcohol-mediated esterification of carboxylic acids with carbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112015009393A2 BR112015009393A2 (pt) | 2017-07-04 |
| BR112015009393B1 true BR112015009393B1 (pt) | 2020-12-22 |
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| BR112015009393-0A BR112015009393B1 (pt) | 2012-10-29 | 2013-10-11 | método de preparação de ésteres |
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| US (2) | US9388116B2 (https=) |
| EP (1) | EP2912007B1 (https=) |
| JP (2) | JP6084699B2 (https=) |
| KR (1) | KR102038177B1 (https=) |
| CN (1) | CN104661992B (https=) |
| AU (1) | AU2013338397B2 (https=) |
| BR (1) | BR112015009393B1 (https=) |
| CA (1) | CA2885311C (https=) |
| ES (1) | ES2762415T3 (https=) |
| IN (1) | IN2015DN04068A (https=) |
| MX (1) | MX363515B (https=) |
| PL (1) | PL2912007T3 (https=) |
| SG (2) | SG10201701568XA (https=) |
| WO (1) | WO2014070415A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107848995B (zh) | 2015-04-14 | 2021-12-28 | 杜邦公司 | 用于生产2,5-呋喃二甲酸及其衍生物以及由其制成的聚合物的方法 |
| JP7458147B2 (ja) | 2016-01-13 | 2024-03-29 | ストラ エンソ オーユーイー | ２，５－フランジカルボン酸ならびにその中間体および誘導体の製造方法 |
| CN105712875B (zh) * | 2016-01-22 | 2019-03-05 | 广西大学 | 一种松香树脂酸的甲酯化方法 |
| CA3069521A1 (en) | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| TWI654178B (zh) | 2017-12-28 | 2019-03-21 | 財團法人工業技術研究院 | 二烷基碳酸酯之製備方法 |
| KR102422368B1 (ko) * | 2020-09-29 | 2022-07-18 | 한국화학연구원 | 금속 유기산염의 에스테르화 방법 및 이를 이용한 이산화탄소의 전환 반응 시스템 |
| WO2023075472A1 (ko) * | 2021-10-29 | 2023-05-04 | 주식회사 엘지화학 | 프로판 트리카복실레이트계 가소제 조성물 및 이를 포함하는 수지 조성물 |
| CN114394897B (zh) * | 2022-01-25 | 2024-05-28 | 北京微量化学研究所 | 含水溶剂体系中酯的制备方法 |
| CN121419957A (zh) * | 2023-07-27 | 2026-01-27 | 三菱瓦斯化学尼克斯株式会社 | 基于伴随着羧酸酯衍生物的脱水缩合的环化反应的环化产物的制造方法以及1,3,4-取代-吡唑-5-羧酸酯类的制造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS55100339A (en) * | 1979-01-25 | 1980-07-31 | Sumitomo Chem Co Ltd | Preparation of carboxylic acid aryl ester |
| US4513146A (en) * | 1982-09-23 | 1985-04-23 | Ppg Industries, Inc. | Method for producing esters from highly hindered carboxylic acids or their salts, and carbonates |
| DE4311424A1 (de) * | 1993-04-07 | 1994-10-13 | Bayer Ag | Verfahren zur O-Alkylierung von Carbonsäuren |
| US5578173A (en) * | 1995-04-03 | 1996-11-26 | Eastman Kodak Company | Removal of dimethylterephthalate from a methanolysis vapor stream |
| ATE207869T1 (de) * | 1995-09-25 | 2001-11-15 | Ciba Sc Holding Ag | Verfahren zur herstellung von dialkylsuccinylsuccinaten |
| US6482977B1 (en) * | 2000-07-28 | 2002-11-19 | General Electric Company | Melt process for the synthesis of diaryl esters of aliphatic diacids |
| US6515167B1 (en) * | 2001-10-17 | 2003-02-04 | Novartis Ag | Low temperature process for preparing methyl esters |
| US20080249329A1 (en) * | 2005-09-29 | 2008-10-09 | Dsm Ip Assets B.V. | Process For Esterification Of An Organic Acid |
| GB0709460D0 (en) * | 2007-05-17 | 2007-06-27 | Croda Int Plc | Method of making polyglycerol esters |
| DE102008004726A1 (de) * | 2008-01-16 | 2009-07-23 | Evonik Goldschmidt Gmbh | Verfahren zur enzymatischen Herstellung von Carbonsäureestern |
| JP2009292737A (ja) * | 2008-06-02 | 2009-12-17 | Sakamoto Yakuhin Kogyo Co Ltd | ポリグリセリン脂肪酸エステルとその製造方法 |
| JP5454996B2 (ja) * | 2008-08-02 | 2014-03-26 | 志朗 坂 | 脂肪酸アルキルエステル組成物の製造方法及び油脂類の処理方法 |
| US7977447B2 (en) * | 2008-11-18 | 2011-07-12 | Sabic Innovative Plastics Ip B.V. | Method for making carbonates and esters |
| CN103180286B (zh) * | 2010-08-24 | 2015-12-16 | 阿彻丹尼尔斯米德兰德公司 | 用于制造基于可再生源的柠檬酸酯和酰化的柠檬酸酯的方法 |
| WO2014099438A2 (en) * | 2012-12-20 | 2014-06-26 | Archer Daniels Midland Company | Esterification of 2,5-furan-dicarboxylic acid |
| SG11201503745SA (en) * | 2012-12-20 | 2015-07-30 | Archer Daniels Midland Co | Recovering and using carboxylic acids from a fermentation broth |
| MX374839B (es) * | 2012-12-20 | 2025-03-06 | Archer Daniels Midland Co | Produccion de biocombustibles a partir de esteres de acidos carboxilicos bioderivados. |
| MX362055B (es) * | 2012-12-20 | 2019-01-07 | Archer Daniels Midland Co | Productos de hidrogenación obtenidos a partir de ésteres de ácidos carboxílicos derivados biológicamente. |
-
2013
- 2013-10-11 KR KR1020157009833A patent/KR102038177B1/ko active Active
- 2013-10-11 JP JP2015539645A patent/JP6084699B2/ja active Active
- 2013-10-11 AU AU2013338397A patent/AU2013338397B2/en active Active
- 2013-10-11 BR BR112015009393-0A patent/BR112015009393B1/pt active IP Right Grant
- 2013-10-11 WO PCT/US2013/064458 patent/WO2014070415A1/en not_active Ceased
- 2013-10-11 PL PL13851598T patent/PL2912007T3/pl unknown
- 2013-10-11 US US14/437,750 patent/US9388116B2/en active Active
- 2013-10-11 ES ES13851598T patent/ES2762415T3/es active Active
- 2013-10-11 SG SG10201701568XA patent/SG10201701568XA/en unknown
- 2013-10-11 CN CN201380050376.7A patent/CN104661992B/zh active Active
- 2013-10-11 SG SG11201501693TA patent/SG11201501693TA/en unknown
- 2013-10-11 MX MX2015005292A patent/MX363515B/es unknown
- 2013-10-11 CA CA2885311A patent/CA2885311C/en active Active
- 2013-10-11 IN IN4068DEN2015 patent/IN2015DN04068A/en unknown
- 2013-10-11 EP EP13851598.6A patent/EP2912007B1/en active Active
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2016
- 2016-06-09 US US15/177,488 patent/US20160289161A1/en not_active Abandoned
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2017
- 2017-01-25 JP JP2017011445A patent/JP2017081998A/ja active Pending
Also Published As
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|---|---|
| EP2912007B1 (en) | 2019-11-20 |
| MX363515B (es) | 2019-03-26 |
| CA2885311C (en) | 2019-10-29 |
| MX2015005292A (es) | 2015-07-17 |
| KR102038177B1 (ko) | 2019-10-29 |
| JP2017081998A (ja) | 2017-05-18 |
| EP2912007A4 (en) | 2016-08-24 |
| US20150299095A1 (en) | 2015-10-22 |
| CN104661992A (zh) | 2015-05-27 |
| JP6084699B2 (ja) | 2017-02-22 |
| WO2014070415A1 (en) | 2014-05-08 |
| IN2015DN04068A (https=) | 2015-10-09 |
| AU2013338397B2 (en) | 2017-11-16 |
| EP2912007A1 (en) | 2015-09-02 |
| BR112015009393A2 (pt) | 2017-07-04 |
| ES2762415T3 (es) | 2020-05-25 |
| CN104661992B (zh) | 2018-03-09 |
| JP2015536331A (ja) | 2015-12-21 |
| SG10201701568XA (en) | 2017-03-30 |
| US9388116B2 (en) | 2016-07-12 |
| PL2912007T3 (pl) | 2020-03-31 |
| CA2885311A1 (en) | 2014-05-08 |
| AU2013338397A1 (en) | 2015-03-19 |
| SG11201501693TA (en) | 2015-05-28 |
| US20160289161A1 (en) | 2016-10-06 |
| KR20150076162A (ko) | 2015-07-06 |
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