DE69621902T2 - Verfahren zum Herstellen von Alkylacrylat - Google Patents
Verfahren zum Herstellen von AlkylacrylatInfo
- Publication number
- DE69621902T2 DE69621902T2 DE69621902T DE69621902T DE69621902T2 DE 69621902 T2 DE69621902 T2 DE 69621902T2 DE 69621902 T DE69621902 T DE 69621902T DE 69621902 T DE69621902 T DE 69621902T DE 69621902 T2 DE69621902 T2 DE 69621902T2
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- water
- acid
- aqueous
- acrylic acid
- Prior art date
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 80
- 125000005250 alkyl acrylate group Chemical group 0.000 title description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 318
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 310
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 243
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 222
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 152
- 238000005336 cracking Methods 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 87
- 238000006460 hydrolysis reaction Methods 0.000 claims description 84
- 230000007062 hydrolysis Effects 0.000 claims description 80
- 238000005886 esterification reaction Methods 0.000 claims description 78
- 238000010992 reflux Methods 0.000 claims description 78
- 230000032050 esterification Effects 0.000 claims description 71
- 239000002253 acid Substances 0.000 claims description 64
- 238000000926 separation method Methods 0.000 claims description 64
- 239000008346 aqueous phase Substances 0.000 claims description 51
- 239000012074 organic phase Substances 0.000 claims description 51
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 49
- 238000004821 distillation Methods 0.000 claims description 42
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 239000003377 acid catalyst Substances 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 238000004064 recycling Methods 0.000 claims description 17
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 15
- 239000011707 mineral Substances 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 11
- 238000010924 continuous production Methods 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 5
- 238000000066 reactive distillation Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- MZNDIOURMFYZLE-UHFFFAOYSA-N butan-1-ol Chemical compound CCCCO.CCCCO MZNDIOURMFYZLE-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000047 product Substances 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 238000005191 phase separation Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 235000011149 sulphuric acid Nutrition 0.000 description 14
- 239000000376 reactant Substances 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000003301 hydrolyzing effect Effects 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 239000002699 waste material Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 208000005156 Dehydration Diseases 0.000 description 4
- 238000003514 Retro-Michael reaction Methods 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 241000183024 Populus tremula Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- -1 butyl b-hydroxypropionate Chemical compound 0.000 description 3
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- CUTWSDAQYCQTGD-UHFFFAOYSA-N 2-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)C(C)OC(=O)C=C CUTWSDAQYCQTGD-UHFFFAOYSA-N 0.000 description 2
- OWVMFLLVLFONOO-UHFFFAOYSA-N 3-butoxypropanoic acid Chemical compound CCCCOCCC(O)=O OWVMFLLVLFONOO-UHFFFAOYSA-N 0.000 description 2
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- QJDIMJXVXVDXDE-UHFFFAOYSA-N CCCCC=CC(=O)OC(C)C(=O)O Chemical compound CCCCC=CC(=O)OC(C)C(=O)O QJDIMJXVXVDXDE-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- PEPQUBUZFYZZET-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.C=C.OC(=O)C=C PEPQUBUZFYZZET-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 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
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000011368 organic material 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
- 230000020477 pH reduction Effects 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- 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
- C07C67/08—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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1033495P | 1995-12-15 | 1995-12-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69621902D1 DE69621902D1 (de) | 2002-07-25 |
| DE69621902T2 true DE69621902T2 (de) | 2003-02-13 |
Family
ID=21745257
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69621902T Expired - Lifetime DE69621902T2 (de) | 1995-12-15 | 1996-12-04 | Verfahren zum Herstellen von Alkylacrylat |
| DE69634457T Expired - Lifetime DE69634457T2 (de) | 1995-12-15 | 1996-12-04 | Verfahren zum Wiedergewinnen von Butylacrylat, das im Wesentlichen frei von Acrylsäure ist |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69634457T Expired - Lifetime DE69634457T2 (de) | 1995-12-15 | 1996-12-04 | Verfahren zum Wiedergewinnen von Butylacrylat, das im Wesentlichen frei von Acrylsäure ist |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0779268B1 (enExample) |
| JP (2) | JP3941843B2 (enExample) |
| KR (1) | KR970042475A (enExample) |
| BR (1) | BR9605973A (enExample) |
| CA (1) | CA2192264A1 (enExample) |
| CZ (1) | CZ363896A3 (enExample) |
| DE (2) | DE69621902T2 (enExample) |
| ES (1) | ES2177738T3 (enExample) |
| RU (1) | RU2161150C2 (enExample) |
| SG (1) | SG81213A1 (enExample) |
| TW (1) | TW406070B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19851984A1 (de) * | 1998-11-11 | 2000-05-18 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| DE19922722A1 (de) | 1999-05-18 | 2000-11-23 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| US6482976B1 (en) | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| AU5605400A (en) * | 1999-06-17 | 2001-01-09 | Union Carbide Chemicals And Plastics Company Inc. | Processes for conducting equilibrium-limited reactions |
| WO2005007609A1 (de) * | 2003-07-11 | 2005-01-27 | Basf Aktiengesellschaft | Thermisches trennverfahren zur abtrennung wenigstens eines (meth)acrylmonomere angereichert enthaltenden stoffstroms |
| RU2259399C2 (ru) * | 2003-10-22 | 2005-08-27 | Федеральное государственное унитарное предприятие "Саратовский научно-исследовательский институт химии и технологий акриловых мономеров и полимеров с опытным заводом" | Способ получения эфиров акриловой кислоты и алифатических спиртов c2-c8 |
| JP2011026608A (ja) * | 2004-04-23 | 2011-02-10 | Sumitomo Chemical Co Ltd | 化学増幅型ポジ型レジスト組成物及び（メタ）アクリル酸誘導体とその製法 |
| ATE519728T1 (de) * | 2008-01-18 | 2011-08-15 | Arkema Inc | Verfahren zur rückgewinnung eines sulfonsäurekatalysators und wertprodukten aus acrylatnachlauffraktionen |
| WO2012071158A1 (en) | 2010-11-22 | 2012-05-31 | Rohm And Haas Company | Acrylate production process |
| JP5748482B2 (ja) * | 2011-01-14 | 2015-07-15 | 株式会社ダイセル | カルボン酸エステルの製造方法 |
| US10597350B2 (en) * | 2016-05-25 | 2020-03-24 | Dow Global Technologies Llc | Process for recovering byproducts from MMA |
| MY200321A (en) * | 2017-08-17 | 2023-12-20 | Basf Se | Process for continuously preparing n-butyl acrylate or isobutyl acrylate |
| JP2019156738A (ja) * | 2018-03-09 | 2019-09-19 | 三菱ケミカル株式会社 | （メタ）アクリル酸エステルの製造方法 |
| FR3137090B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137088B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation en batch de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137089B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137091B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation continu de sous-produits lourds issus de la fabrication d’acide acrylique |
| CN115490590A (zh) * | 2022-08-29 | 2022-12-20 | 平湖石化有限责任公司 | 带丙烯酸循环的丙烯酸丁酯连续生产工艺 |
| CN117550667B (zh) * | 2023-11-30 | 2025-10-03 | 中环信(南京)环境服务有限公司 | 丙烯酸及酯类回收过程副产含丁醇有机含盐废水综合利用装置及工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868410A (en) * | 1972-08-03 | 1975-02-25 | Celanese Corp | Conversion of oligomeric acrylates to acrylate monomers |
| DE2449811C2 (de) | 1974-10-19 | 1983-01-05 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
| US3951756A (en) * | 1974-11-08 | 1976-04-20 | Celanese Corporation | Purification of alkyl esters |
| DE2552987C2 (de) * | 1975-11-26 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
| US4968834A (en) | 1990-05-07 | 1990-11-06 | Hoechst Celanese Corporation | Recovery of acrylic acid and/or ethyl acrylate from black acid |
| 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 |
| DE19547485A1 (de) * | 1995-12-19 | 1996-05-09 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
-
1996
- 1996-12-02 SG SG9611492A patent/SG81213A1/en unknown
- 1996-12-04 EP EP96308792A patent/EP0779268B1/en not_active Expired - Lifetime
- 1996-12-04 DE DE69621902T patent/DE69621902T2/de not_active Expired - Lifetime
- 1996-12-04 DE DE69634457T patent/DE69634457T2/de not_active Expired - Lifetime
- 1996-12-04 ES ES96308792T patent/ES2177738T3/es not_active Expired - Lifetime
- 1996-12-06 CA CA002192264A patent/CA2192264A1/en not_active Abandoned
- 1996-12-09 KR KR1019960062981A patent/KR970042475A/ko not_active Ceased
- 1996-12-11 CZ CZ963638A patent/CZ363896A3/cs unknown
- 1996-12-12 BR BR9605973A patent/BR9605973A/pt not_active IP Right Cessation
- 1996-12-13 JP JP35293096A patent/JP3941843B2/ja not_active Expired - Lifetime
- 1996-12-15 RU RU96123848/04A patent/RU2161150C2/ru active
-
1997
- 1997-05-16 TW TW086106515A patent/TW406070B/zh not_active IP Right Cessation
-
2007
- 2007-01-04 JP JP2007000210A patent/JP4335925B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2192264A1 (en) | 1997-06-16 |
| SG81213A1 (en) | 2001-06-19 |
| JP4335925B2 (ja) | 2009-09-30 |
| KR970042475A (ko) | 1997-07-24 |
| JP3941843B2 (ja) | 2007-07-04 |
| DE69634457D1 (de) | 2005-04-14 |
| EP0779268B1 (en) | 2002-06-19 |
| CZ363896A3 (en) | 1997-07-16 |
| EP0779268A1 (en) | 1997-06-18 |
| DE69621902D1 (de) | 2002-07-25 |
| DE69634457T2 (de) | 2006-01-26 |
| BR9605973A (pt) | 1998-08-25 |
| RU2161150C2 (ru) | 2000-12-27 |
| TW406070B (en) | 2000-09-21 |
| JPH09208520A (ja) | 1997-08-12 |
| JP2007153903A (ja) | 2007-06-21 |
| ES2177738T3 (es) | 2002-12-16 |
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| 8364 | No opposition during term of opposition |