ES2582454T3 - Procedimiento para preparar ésteres cíclicos que comprenden grupos funcionales insaturados y poliésteres preparados a partir del mismo - Google Patents

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Publication number

ES2582454T3

ES2582454T3 ES10803310.1T ES10803310T ES2582454T3 ES 2582454 T3 ES2582454 T3 ES 2582454T3 ES 10803310 T ES10803310 T ES 10803310T ES 2582454 T3 ES2582454 T3 ES 2582454T3

Authority

ES

Spain

Prior art keywords

substituted

unsubstituted

hydroxyacid

hydroxy

oligomeric

Prior art date

2009-12-21

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.)

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• 125000000524 functional group Chemical group 0.000 title description 7
• 229920000728 polyester Polymers 0.000 title description 5
• 238000004519 manufacturing process Methods 0.000 title description 3
• -1 cyclic ester Chemical class 0.000 claims abstract description 106
• 238000000034 method Methods 0.000 claims abstract description 78
• 239000007788 liquid Substances 0.000 claims abstract description 29
• 239000012429 reaction media Substances 0.000 claims abstract description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
• 239000001257 hydrogen Substances 0.000 claims abstract description 24
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
• 150000002367 halogens Chemical class 0.000 claims abstract description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 22
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 20
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 20
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 19
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
• 239000000203 mixture Substances 0.000 claims abstract description 16
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 9
• 229940061720 alpha hydroxy acid Drugs 0.000 claims abstract description 7
• 150000001280 alpha hydroxy acids Chemical class 0.000 claims abstract description 7
• 238000010438 heat treatment Methods 0.000 claims abstract description 6
• 239000002904 solvent Substances 0.000 claims description 27
• 150000002148 esters Chemical class 0.000 claims description 26
• 239000003054 catalyst Substances 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 239000002685 polymerization catalyst Substances 0.000 claims description 12
• 238000005809 transesterification reaction Methods 0.000 claims description 12
• 150000001261 hydroxy acids Chemical class 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• VFSVBYJVPHDQQC-UHFFFAOYSA-N 2-hydroxypent-4-enoic acid Chemical compound OC(=O)C(O)CC=C VFSVBYJVPHDQQC-UHFFFAOYSA-N 0.000 claims description 5
• CUIIHTGRMOOOJX-UHFFFAOYSA-N 3,6-bis(prop-2-enyl)-1,4-dioxane-2,5-dione Chemical group C=CCC1OC(=O)C(CC=C)OC1=O CUIIHTGRMOOOJX-UHFFFAOYSA-N 0.000 claims description 2
• 230000000379 polymerizing effect Effects 0.000 claims description 2
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 44
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• JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 18
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
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• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 239000003242 anti bacterial agent Substances 0.000 description 4
• 239000004599 antimicrobial Substances 0.000 description 4
• GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 238000007334 copolymerization reaction Methods 0.000 description 4
• 229940088597 hormone Drugs 0.000 description 4
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• 239000012535 impurity Substances 0.000 description 4
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 108010050904 Interferons Proteins 0.000 description 3
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
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