BR112020009418B1 - Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido - Google Patents
Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido Download PDFInfo
- Publication number
- BR112020009418B1 BR112020009418B1 BR112020009418-8A BR112020009418A BR112020009418B1 BR 112020009418 B1 BR112020009418 B1 BR 112020009418B1 BR 112020009418 A BR112020009418 A BR 112020009418A BR 112020009418 B1 BR112020009418 B1 BR 112020009418B1
- Authority
- BR
- Brazil
- Prior art keywords
- group
- sulfonic acid
- organic sulfonic
- lactam
- amino acid
- Prior art date
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- -1 AMINO ACID ESTER Chemical class 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 36
- 150000003460 sulfonic acids Chemical class 0.000 title claims abstract description 18
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
- 150000001413 amino acids Chemical class 0.000 title description 9
- 150000003951 lactams Chemical class 0.000 claims abstract description 71
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000007864 aqueous solution Substances 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims description 42
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 39
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000005425 toluyl group Chemical group 0.000 claims description 5
- 125000006539 C12 alkyl 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 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 claims description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006538 C11 alkyl 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])* 0.000 claims description 2
- 150000001336 alkenes Chemical group 0.000 claims description 2
- 229920005628 alkoxylated polyol Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003955 ε-lactams Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 16
- 238000006243 chemical reaction Methods 0.000 description 41
- 235000001014 amino acid Nutrition 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 22
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 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 11
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 229960005323 phenoxyethanol Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 3
- YDOBHSAXRNUOFX-UHFFFAOYSA-N 3-ethylheptane-1-sulfonic acid Chemical compound CCCCC(CC)CCS(O)(=O)=O YDOBHSAXRNUOFX-UHFFFAOYSA-N 0.000 description 3
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000006177 alkyl benzyl group Chemical group 0.000 description 3
- 229960002684 aminocaproic acid Drugs 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CHZLVSBMXZSPNN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1 CHZLVSBMXZSPNN-UHFFFAOYSA-N 0.000 description 1
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 description 1
- BRETYAHLENMEAI-UHFFFAOYSA-N 2,6-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(C)=C1S(O)(=O)=O BRETYAHLENMEAI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- KPZGPSLTTLYHFC-UHFFFAOYSA-N 4-(3-ethylheptyl)benzenesulfonic acid Chemical compound C(C)C(CCC1=CC=C(C=C1)S(=O)(=O)O)CCCC KPZGPSLTTLYHFC-UHFFFAOYSA-N 0.000 description 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HUSZVWYKLJAGAK-UHFFFAOYSA-N S(C)(=O)(=O)O.C(CCCCC)N Chemical compound S(C)(=O)(=O)O.C(CCCCC)N HUSZVWYKLJAGAK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
- C07C309/31—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups by alkyl groups containing at least three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17205357 | 2017-12-05 | ||
| EP17205357.1 | 2017-12-05 | ||
| PCT/EP2018/082663 WO2019110371A1 (en) | 2017-12-05 | 2018-11-27 | Organic sulfonic acid salts of amino acid esters and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
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| BR112020009418A2 BR112020009418A2 (pt) | 2020-10-13 |
| BR112020009418B1 true BR112020009418B1 (pt) | 2023-10-10 |
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Country Status (10)
| Country | Link |
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| US (1) | US11780802B2 (https=) |
| EP (1) | EP3720838B1 (https=) |
| JP (2) | JP7420718B2 (https=) |
| CN (1) | CN111433184B (https=) |
| BR (1) | BR112020009418B1 (https=) |
| ES (1) | ES2924880T3 (https=) |
| MX (1) | MX2020005956A (https=) |
| PL (1) | PL3720838T3 (https=) |
| RU (1) | RU2020122121A (https=) |
| WO (1) | WO2019110371A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112020009418B1 (pt) * | 2017-12-05 | 2023-10-10 | Basf Se | Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido |
| ES2928825T3 (es) * | 2018-07-03 | 2022-11-22 | Nouryon Chemicals Int Bv | Esteres de ácidos amino carboxílicos y un proceso para prepararlos |
| EP3845519A1 (en) * | 2019-12-30 | 2021-07-07 | Nouryon Chemicals International B.V. | Esters of amino carboxylic acids and a process to prepare them |
| TWI856233B (zh) * | 2020-01-29 | 2024-09-21 | 美商艾德凡斯化學公司 | 胺基酸界面活性劑 |
| AU2021236069B9 (en) * | 2020-03-11 | 2024-02-01 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
| EP3933017B1 (en) | 2020-07-03 | 2026-04-08 | The Procter & Gamble Company | Fabric and home care product comprising a sulfatized esteramine |
| JP2023532715A (ja) | 2020-07-03 | 2023-07-31 | ビーエーエスエフ ソシエタス・ヨーロピア | 硫酸化エステルアミン |
| BR112023000343A2 (pt) * | 2020-07-09 | 2023-01-31 | Advansix Resins & Chemicals Llc | Tensoativos de aminoácido ramificado |
| AU2021306216B2 (en) * | 2020-07-09 | 2023-12-21 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants |
| CN116075582B (zh) * | 2020-07-13 | 2025-08-19 | 艾德凡斯化学公司 | 用于清洁产品的支链氨基酸表面活性剂 |
| CA3185065A1 (en) * | 2020-07-13 | 2022-01-20 | Edward Asirvatham | Branched amino acid surfactants for agricultural products |
| AU2021307397B2 (en) * | 2020-07-13 | 2024-06-13 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for use in healthcare products |
| WO2022015604A1 (en) | 2020-07-13 | 2022-01-20 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for personal care and cosmetic products |
| CA3298099A1 (en) | 2020-07-13 | 2026-03-02 | Advansix Resins & Chemicals Llc | Branched amino acid surfactants for electronics products |
| EP4179038A1 (en) * | 2020-07-13 | 2023-05-17 | AdvanSix Resins & Chemicals LLC | Branched amino acid surfactants for oil and gas production |
| CN116057130B (zh) * | 2020-07-13 | 2024-05-28 | 艾德凡斯化学公司 | 用于油墨、涂料和胶粘剂的支链氨基酸表面活性剂 |
| EP4019615A1 (en) | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Liquid hand dishwashing cleaning composition |
| EP4019614A1 (en) * | 2020-12-28 | 2022-06-29 | The Procter & Gamble Company | Cleaning product |
| WO2024042005A1 (en) | 2022-08-22 | 2024-02-29 | Basf Se | Process for producing sulfatized esteramines |
| GB2627342A (en) * | 2022-12-16 | 2024-08-21 | Basf Se | Process for the preparation of amino acids esters and organic sulfonic acids salts thereof and amino acid esters and their salts |
| DE102023135175A1 (de) | 2022-12-16 | 2024-06-27 | Basf Se | Verfahren zur Herstellung von Aminosäureestern und organischen Sulfonsäuresalzen sowie Aminosäureestern und deren Salzen |
| EP4386074B1 (en) | 2022-12-16 | 2025-12-03 | The Procter & Gamble Company | Fabric and home care composition |
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| NL270754A (https=) * | 1960-10-28 | 1900-01-01 | ||
| US3939200A (en) | 1966-01-06 | 1976-02-17 | Rohm And Haas Company | Aliphatic acyl-containing amine hydrochlorides |
| US4176232A (en) * | 1968-06-27 | 1979-11-27 | Rohm And Haas Company | Sulfonic acid salts of acyloxyalkylamines |
| FR2208976B1 (https=) * | 1972-11-30 | 1978-02-24 | Modokemi Ab | |
| US4154956A (en) * | 1973-12-21 | 1979-05-15 | Toray Industries, Inc. | Method for producing lysine ester |
| JPS5339410B2 (https=) * | 1973-12-21 | 1978-10-21 | ||
| US4340730A (en) * | 1980-06-09 | 1982-07-20 | G. D. Searle & Co. | N6 -Substituted adenosines |
| SU1276661A1 (ru) * | 1983-02-17 | 1986-12-15 | Институт фармакологии АМН СССР | Гексадецилсульфаты гексадециловых эфиров аминокислот,обладающие нейротропной и ноотропной активностью |
| US4550137A (en) * | 1983-03-28 | 1985-10-29 | Ppg Industries, Inc. | Lactam derived salts of sulfonic acids as latent acid catalysts |
| JP3792295B2 (ja) * | 1996-05-09 | 2006-07-05 | 花王株式会社 | 新規なアミノ酸エステル塩及びその製造法並びにそれを含有する柔軟剤組成物 |
| KR101580067B1 (ko) * | 2007-01-12 | 2015-12-23 | 노파르티스 아게 | 5-바이페닐-4-아미노-2-메틸 펜탄산의 제조 방법 |
| FR2977585B1 (fr) | 2011-07-06 | 2015-08-28 | Ard Sa | Procede de preparation d'esters |
| TWI591045B (zh) | 2012-08-03 | 2017-07-11 | 祥翊製藥股份有限公司 | 作為有效藥劑成分之６－胺基己酸的製造方法 |
| ES2895710T3 (es) | 2014-05-09 | 2022-02-22 | Inolex Investment Corp | Emulsionantes catiónicos de origen no petroquímico y composiciones y métodos relacionados |
| MX380337B (es) | 2014-09-08 | 2025-03-11 | Mexicano Inst Petrol | Proceso mejorado para la obtencion de esteres de amioacidos ionicos. |
| AU2016236239B2 (en) * | 2015-03-24 | 2020-06-25 | H. Lundbeck A/S | Manufacture of 4,5,6,7-tetrahydroisozaxolo[5,4-c]pyridin-3-ol |
| BR112020009418B1 (pt) * | 2017-12-05 | 2023-10-10 | Basf Se | Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido |
-
2018
- 2018-11-27 BR BR112020009418-8A patent/BR112020009418B1/pt active IP Right Grant
- 2018-11-27 MX MX2020005956A patent/MX2020005956A/es unknown
- 2018-11-27 PL PL18804653.6T patent/PL3720838T3/pl unknown
- 2018-11-27 WO PCT/EP2018/082663 patent/WO2019110371A1/en not_active Ceased
- 2018-11-27 ES ES18804653T patent/ES2924880T3/es active Active
- 2018-11-27 EP EP18804653.6A patent/EP3720838B1/en active Active
- 2018-11-27 CN CN201880078186.9A patent/CN111433184B/zh active Active
- 2018-11-27 RU RU2020122121A patent/RU2020122121A/ru unknown
- 2018-11-27 JP JP2020531125A patent/JP7420718B2/ja active Active
- 2018-11-27 US US16/770,080 patent/US11780802B2/en active Active
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2023
- 2023-10-02 JP JP2023171226A patent/JP2024001105A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7420718B2 (ja) | 2024-01-23 |
| JP2021505614A (ja) | 2021-02-18 |
| CN111433184B (zh) | 2025-06-06 |
| ES2924880T3 (es) | 2022-10-11 |
| MX2020005956A (es) | 2020-08-24 |
| EP3720838A1 (en) | 2020-10-14 |
| CN111433184A (zh) | 2020-07-17 |
| WO2019110371A1 (en) | 2019-06-13 |
| BR112020009418A2 (pt) | 2020-10-13 |
| JP2024001105A (ja) | 2024-01-09 |
| US20210188764A1 (en) | 2021-06-24 |
| PL3720838T3 (pl) | 2022-12-19 |
| US11780802B2 (en) | 2023-10-10 |
| EP3720838B1 (en) | 2022-08-03 |
| RU2020122121A (ru) | 2022-01-10 |
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Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 27/11/2018, OBSERVADAS AS CONDICOES LEGAIS |