BR112015032389B1 - processo para a produçâo contínua de acrilatos leves pela esterificação de um ácido acrílico em grau éster bruto - Google Patents
processo para a produçâo contínua de acrilatos leves pela esterificação de um ácido acrílico em grau éster bruto Download PDFInfo
- Publication number
- BR112015032389B1 BR112015032389B1 BR112015032389-8A BR112015032389A BR112015032389B1 BR 112015032389 B1 BR112015032389 B1 BR 112015032389B1 BR 112015032389 A BR112015032389 A BR 112015032389A BR 112015032389 B1 BR112015032389 B1 BR 112015032389B1
- Authority
- BR
- Brazil
- Prior art keywords
- acrylic acid
- light
- crude
- reaction
- flow
- Prior art date
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 152
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 238000000034 method Methods 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 57
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 41
- 150000002148 esters Chemical class 0.000 title abstract description 26
- 230000032050 esterification Effects 0.000 title abstract description 25
- 238000010924 continuous production Methods 0.000 title abstract 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000000746 purification Methods 0.000 claims abstract description 34
- 125000005396 acrylic acid ester group Chemical group 0.000 claims abstract description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 29
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 19
- 230000005593 dissociations Effects 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 238000011065 in-situ storage Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 238000010992 reflux Methods 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 11
- 239000002994 raw material Substances 0.000 claims description 11
- 230000018044 dehydration Effects 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 7
- 235000011187 glycerol Nutrition 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000178 monomer Substances 0.000 description 20
- 238000011084 recovery Methods 0.000 description 17
- 239000013638 trimer Substances 0.000 description 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 16
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000000539 dimer Substances 0.000 description 13
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 229950000688 phenothiazine Drugs 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- -1 for example Chemical compound 0.000 description 9
- 238000005194 fractionation Methods 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 238000004064 recycling Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
- AODAQIOEZVDQLS-UHFFFAOYSA-N 3,4-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1C(C)(C)C AODAQIOEZVDQLS-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- CRBWLPLGQBCCCY-UHFFFAOYSA-L copper;dicarbamate Chemical class [Cu+2].NC([O-])=O.NC([O-])=O CRBWLPLGQBCCCY-UHFFFAOYSA-L 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OAPQYLLXPVESTE-UHFFFAOYSA-N ethyl 2-prop-2-enoyloxypropanoate Chemical class CCOC(=O)C(C)OC(=O)C=C OAPQYLLXPVESTE-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
-
- 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
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1357447A FR3008971B1 (fr) | 2013-07-29 | 2013-07-29 | Procede de production en continu d'acrylates legers par esterification d'un acide acrylique de grade ester brut |
| FR1357447 | 2013-07-29 | ||
| PCT/FR2014/051928 WO2015015100A1 (fr) | 2013-07-29 | 2014-07-24 | Procede de production en continu d'acrylates legers par esterification d'un acide acrylique de grade ester brut |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112015032389A2 BR112015032389A2 (pt) | 2017-07-25 |
| BR112015032389B1 true BR112015032389B1 (pt) | 2020-12-08 |
Family
ID=49474624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112015032389-8A BR112015032389B1 (pt) | 2013-07-29 | 2014-07-24 | processo para a produçâo contínua de acrilatos leves pela esterificação de um ácido acrílico em grau éster bruto |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9796651B2 (enExample) |
| EP (1) | EP3027586B1 (enExample) |
| JP (1) | JP6595467B2 (enExample) |
| KR (1) | KR102207641B1 (enExample) |
| CN (1) | CN105408299B (enExample) |
| BR (1) | BR112015032389B1 (enExample) |
| FR (1) | FR3008971B1 (enExample) |
| WO (1) | WO2015015100A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6574305B2 (ja) * | 2015-08-28 | 2019-09-11 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | ヒドロキシプロピオン酸及びその誘導体の脱水用触媒 |
| FR3083233B1 (fr) * | 2018-06-27 | 2020-05-29 | Arkema France | Procede de purification d'acrylates legers. |
| JP2022529126A (ja) * | 2019-04-16 | 2022-06-17 | ローム アンド ハース カンパニー | 酸触媒によるアクリル酸およびメタノールからのアクリル酸メチルの合成 |
| US12098124B2 (en) | 2019-04-16 | 2024-09-24 | Rohm And Haas Company | Acid catalyzed synthesis of methyl acrylate from acrylic acid and methanol |
| FR3125040B1 (fr) | 2021-07-09 | 2024-04-26 | Snf Sa | Procédé d’obtention de bio-monomère à partir de diméthylaminoethanol d’origine renouvelable |
| FR3125042B1 (fr) | 2021-07-09 | 2024-04-12 | Snf Sa | Procédé d’obtention d’alkyl(méth)acrylamide substitué biosourcé |
| CN116253653A (zh) * | 2023-03-23 | 2023-06-13 | 深圳飞扬骏研新材料股份有限公司 | 一种聚天门冬氨酸酯树脂的连续生产工艺 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1351243A (fr) | 1963-03-20 | 1964-01-31 | Basf Ag | Procédé pour le traitement en continu des résidus qui se forment lors de la synthèse d'acide acrylique ou de ses esters |
| US3868410A (en) | 1972-08-03 | 1975-02-25 | Celanese Corp | Conversion of oligomeric acrylates to acrylate monomers |
| US4076950A (en) * | 1976-07-19 | 1978-02-28 | Rohm And Haas Company | Process for manufacture of alkyl esters of aliphatic carboxylic acids |
| US4999452A (en) * | 1989-05-15 | 1991-03-12 | Union Carbide Chemicals And Plastics Company Inc. | Process for producing acrylic ester |
| FR2650587B1 (fr) | 1989-08-03 | 1991-10-18 | Norsolor Sa | Procede de preparation en continu d'acrylates legers |
| FR2700767B1 (fr) * | 1993-01-27 | 1995-04-07 | Atochem Elf Sa | Procédé perfectionné de fabrication de (méthacrylates d'alkyle par estérification directe. |
| FR2727964B1 (fr) * | 1994-12-12 | 1997-01-24 | Atochem Elf Sa | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters |
| FR2736912B1 (fr) * | 1995-07-18 | 1997-08-22 | Atochem Elf Sa | Procede de purification de l'acide acrylique obtenu par oxydation catalytique du propylene |
| DE19547459A1 (de) * | 1995-12-19 | 1996-07-25 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| US6605738B1 (en) | 1996-05-29 | 2003-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butyl acrylate |
| BR9714713A (pt) * | 1997-05-20 | 2000-07-04 | Union Carbide Chem Plastic | Processos para o refino de acrilato de butila |
| JPH10316719A (ja) | 1997-05-20 | 1998-12-02 | Daikin Ind Ltd | 新規重合体およびそれを含む防汚加工剤組成物 |
| WO1998052903A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| DE19721400A1 (de) | 1997-05-22 | 1998-11-26 | Basf Ag | Verfahren zur Herstellung von Dienpolymerisatlösungen in vinylaromatischen Monomeren |
| JPH1112222A (ja) | 1997-06-25 | 1999-01-19 | Nippon Shokubai Co Ltd | アクリル酸の回収方法 |
| JP2001521919A (ja) * | 1997-10-31 | 2001-11-13 | セラニーズ・インターナショナル・コーポレーション | アクリレートの系から硫黄を除去する方法 |
| US6482976B1 (en) | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| WO2000078702A1 (en) * | 1999-06-17 | 2000-12-28 | Union Carbide Chemicals & Plastics | Processes for conducting equilibrium-limited reactions |
| DE10144490A1 (de) | 2001-09-10 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| JP4302934B2 (ja) * | 2002-04-25 | 2009-07-29 | 株式会社日本触媒 | ミカエル型付加物の分解方法 |
| JP2004043448A (ja) * | 2002-05-16 | 2004-02-12 | Mitsubishi Chemicals Corp | （メタ）アクリル酸類の製造方法 |
| DE102004008575A1 (de) * | 2004-02-19 | 2005-09-08 | Stockhausen Gmbh | Spaltung oligomerer (Meth)acrylsäure in flüssiger Phase unter Druck |
| FR2881136B1 (fr) | 2005-01-21 | 2007-03-23 | Arkema Sa | Procede de preparation de l'acide acrylique comprenant une oxydation partielle du propane en propylene |
| CN101516820B (zh) * | 2006-09-15 | 2012-11-21 | 阿克马公司 | 制备丙烯酸的方法 |
| JP2009242286A (ja) * | 2008-03-31 | 2009-10-22 | Mitsubishi Chemicals Corp | アクリル酸の製造方法 |
| FR2934261B1 (fr) * | 2008-07-25 | 2015-04-10 | Arkema France | Procede de synthese d'esters de l'acide acrylique |
| DE102008054587A1 (de) * | 2008-12-12 | 2010-06-17 | Basf Se | Verfahren zur Rückspaltung von in einer Flüssigkeit F enthaltenen Michael-Addukten, die bei der Herstellung von Acrylsäure oder deren Ester gebildet wurde |
| FR2948365B1 (fr) * | 2009-07-22 | 2011-09-09 | Arkema France | Procede de fabrication d'acide acrylique bio-ressource a partir de glycerol |
| WO2012101471A1 (en) * | 2011-01-28 | 2012-08-02 | Arkema France | Improved process for manufacturing acrolein/acrylic acid |
| CA2837448A1 (en) | 2011-06-28 | 2013-01-03 | Wintech Polymer Ltd. | Resin molded body |
-
2013
- 2013-07-29 FR FR1357447A patent/FR3008971B1/fr active Active
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2014
- 2014-07-24 WO PCT/FR2014/051928 patent/WO2015015100A1/fr not_active Ceased
- 2014-07-24 US US14/906,292 patent/US9796651B2/en active Active
- 2014-07-24 BR BR112015032389-8A patent/BR112015032389B1/pt active IP Right Grant
- 2014-07-24 EP EP14750583.8A patent/EP3027586B1/fr active Active
- 2014-07-24 KR KR1020167005525A patent/KR102207641B1/ko active Active
- 2014-07-24 JP JP2016530579A patent/JP6595467B2/ja active Active
- 2014-07-24 CN CN201480042612.5A patent/CN105408299B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9796651B2 (en) | 2017-10-24 |
| KR20160036627A (ko) | 2016-04-04 |
| US20160159725A1 (en) | 2016-06-09 |
| CN105408299A (zh) | 2016-03-16 |
| CN105408299B (zh) | 2018-04-24 |
| JP6595467B2 (ja) | 2019-10-23 |
| FR3008971B1 (fr) | 2016-08-19 |
| KR102207641B1 (ko) | 2021-01-25 |
| WO2015015100A1 (fr) | 2015-02-05 |
| BR112015032389A2 (pt) | 2017-07-25 |
| EP3027586B1 (fr) | 2020-02-26 |
| FR3008971A1 (fr) | 2015-01-30 |
| JP2016525565A (ja) | 2016-08-25 |
| EP3027586A1 (fr) | 2016-06-08 |
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