BR112017011304B1 - processo para a preparação de ésteres de ácido láctico e ácido 2-hidroxi-3-butenoico ou alfa-hidroxi-análogos de metionina a partir de açúcares - Google Patents
processo para a preparação de ésteres de ácido láctico e ácido 2-hidroxi-3-butenoico ou alfa-hidroxi-análogos de metionina a partir de açúcares Download PDFInfo
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- BR112017011304B1 BR112017011304B1 BR112017011304A BR112017011304A BR112017011304B1 BR 112017011304 B1 BR112017011304 B1 BR 112017011304B1 BR 112017011304 A BR112017011304 A BR 112017011304A BR 112017011304 A BR112017011304 A BR 112017011304A BR 112017011304 B1 BR112017011304 B1 BR 112017011304B1
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- Prior art keywords
- fact
- hydroxy
- catalyst
- volume
- water
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 68
- 230000008569 process Effects 0.000 title claims abstract description 65
- 235000000346 sugar Nutrition 0.000 title claims abstract description 39
- VBWPSWWDYVWZKA-UHFFFAOYSA-N 2-hydroxybut-3-enoic acid Chemical compound C=CC(O)C(O)=O VBWPSWWDYVWZKA-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000008163 sugars Chemical class 0.000 title abstract description 14
- AQPJRTNUBAWORL-RXMQYKEDSA-N (2r)-2-amino-2-hydroxy-4-methylsulfanylbutanoic acid Chemical class CSCC[C@@](N)(O)C(O)=O AQPJRTNUBAWORL-RXMQYKEDSA-N 0.000 title abstract description 11
- 150000003903 lactic acid esters Chemical class 0.000 title description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 32
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 18
- 238000005112 continuous flow technique Methods 0.000 claims abstract description 15
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 13
- 239000004310 lactic acid Substances 0.000 claims abstract description 13
- 239000011973 solid acid Substances 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 87
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 80
- 239000002841 Lewis acid Substances 0.000 claims description 16
- 150000007517 lewis acids Chemical class 0.000 claims description 16
- 239000011949 solid catalyst Substances 0.000 claims description 15
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- 239000005715 Fructose Substances 0.000 claims description 11
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 11
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- 229930006000 Sucrose Natural products 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
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- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 claims description 3
- 206010056474 Erythrosis Diseases 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 54
- JBKTVPSFVUFSAO-UHFFFAOYSA-N methyl 2-hydroxybut-3-enoate Chemical compound COC(=O)C(O)C=C JBKTVPSFVUFSAO-UHFFFAOYSA-N 0.000 description 51
- -1 for example Substances 0.000 description 24
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
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- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 11
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- 229940057867 methyl lactate Drugs 0.000 description 11
- 239000003513 alkali Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
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- 239000006188 syrup Substances 0.000 description 10
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- 239000000047 product Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001356 alkyl thiols Chemical class 0.000 description 6
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 6
- 229910021536 Zeolite Inorganic materials 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
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- 238000001354 calcination Methods 0.000 description 4
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- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- QRTJEZQSJSURPR-UHFFFAOYSA-N methyl 2-hydroxy-4-methoxybutanoate Chemical compound COC(C(CCOC)O)=O QRTJEZQSJSURPR-UHFFFAOYSA-N 0.000 description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
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- MCEPYJYPIASGNF-UHFFFAOYSA-N ethyl 2-hydroxy-4-methylsulfanylbutanoate Chemical compound CCOC(=O)C(O)CCSC MCEPYJYPIASGNF-UHFFFAOYSA-N 0.000 description 1
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- 150000002402 hexoses Chemical class 0.000 description 1
- YWWBUZVHTWILSP-UHFFFAOYSA-N hexyl 2-hydroxy-4-methylsulfanylbutanoate Chemical compound CCCCCCOC(=O)C(O)CCSC YWWBUZVHTWILSP-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000005470 impregnation Methods 0.000 description 1
- 238000009616 inductively coupled plasma Methods 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
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- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- PODDEHMTBTUCGO-UHFFFAOYSA-N octyl 2-hydroxy-4-methylsulfanylbutanoate Chemical compound CCCCCCCCOC(=O)C(O)CCSC PODDEHMTBTUCGO-UHFFFAOYSA-N 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229910021426 porous silicon Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 1
- 235000011085 potassium lactate Nutrition 0.000 description 1
- 239000001521 potassium lactate Substances 0.000 description 1
- 229960001304 potassium lactate Drugs 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/68—Lactic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- 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
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| DKPA201500288 | 2015-05-13 | ||
| PCT/EP2015/076399 WO2016083137A1 (en) | 2014-11-28 | 2015-11-12 | Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars |
Publications (2)
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| BR112017011304A2 BR112017011304A2 (pt) | 2018-07-10 |
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| AU (1) | AU2015352840B2 (enExample) |
| BR (1) | BR112017011304B1 (enExample) |
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| CA2968906C (en) | 2014-11-28 | 2023-09-12 | Haldor Topsoe A/S | Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars |
| MX377376B (es) | 2015-04-30 | 2025-03-10 | Haldor Topsoe As | Un proceso para la preparacion de analogos alfa-hidroxilados de metionina a partir de azucares y derivados de los mismos. |
| TWI712584B (zh) | 2016-05-04 | 2020-12-11 | 丹麥商托普索公司 | 新穎己二酯類化合物及其製備方法 |
| CN106349060B (zh) * | 2016-08-26 | 2020-06-12 | 上海交通大学 | 一种路易斯酸催化转化碳水化合物制备乳酸烷基酯的方法 |
| CN109289909B (zh) * | 2018-10-16 | 2021-03-19 | 郑州大学 | 一种催化复杂糖转化制备乳酸酯的催化剂 |
| KR20220057525A (ko) * | 2019-09-06 | 2022-05-09 | 케민 인더스트리즈, 인코포레이티드 | 알파-하이드록시 산의 에스테르화에 의한 알파-하이드록시 에스테르의 제조 공정 |
| CN111905802B (zh) * | 2020-06-15 | 2022-01-18 | 厦门大学 | 一种使用钼-碱金属/碱土金属修饰的路易斯酸催化剂制乳酸酯的方法 |
| CN113831238B (zh) * | 2020-06-24 | 2024-05-03 | 中国石油化工股份有限公司 | 一种催化转化碳水化合物制备乳酸甲酯的方法 |
| CN116272945B (zh) * | 2023-01-16 | 2024-12-31 | 山东理工大学 | 酸碱碳基催化剂的制备方法及应用 |
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| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| US4933161A (en) | 1987-02-04 | 1990-06-12 | Exxon Research And Engineering Company | Tin substitution into zeolite frameworks |
| US5973200A (en) | 1997-01-23 | 1999-10-26 | Novus International, Inc. | Process for the preparation of 2-hydroxy-4-(methylthio) butanoic acid or methionine by mercaptan addition |
| DE10140202A1 (de) | 2001-08-16 | 2003-03-06 | Bayer Ag | Vanadium-Imido-Phosphoraniminato für die Olefinpolymerisation |
| DE102005003990A1 (de) * | 2005-01-28 | 2006-08-03 | Degussa Ag | Herstellung von 3-(Alkylthio)propanal |
| PL2184270T3 (pl) * | 2008-11-11 | 2013-07-31 | Haldor Topsoe As | Katalizowane zeolitem wytwarzanie związków alfa-hydroksykwasów karboksylowych i ich estrów |
| FR2938535B1 (fr) * | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
| EP2415750B1 (en) * | 2009-04-03 | 2018-02-14 | Mitsubishi Gas Chemical Company, Inc. | Method for producing alpha-hydroxycarboxylic acid ester |
| TWI630197B (zh) | 2013-02-27 | 2018-07-21 | 丹麥商哈爾德杜薩公司 | 從包含低分子量羰基化合物之組成物移除甲醛的方法 |
| LT3036040T (lt) | 2013-08-20 | 2018-02-12 | Haldor Topsoe A/S | Cukrų konversijos į pieno rūgštį ir 2-hidroksi-3-buteno rūgštį arba jų esterius būdas, apimantis metalo-silikato medžiagą ir metalo joną |
| CA2968906C (en) | 2014-11-28 | 2023-09-12 | Haldor Topsoe A/S | Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars |
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| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
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