KR101136783B1 - 평형 제한 반응의 수행방법 - Google Patents
평형 제한 반응의 수행방법 Download PDFInfo
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- KR101136783B1 KR101136783B1 KR1020057016051A KR20057016051A KR101136783B1 KR 101136783 B1 KR101136783 B1 KR 101136783B1 KR 1020057016051 A KR1020057016051 A KR 1020057016051A KR 20057016051 A KR20057016051 A KR 20057016051A KR 101136783 B1 KR101136783 B1 KR 101136783B1
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- South Korea
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- Expired - Lifetime
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 211
- 238000000034 method Methods 0.000 title claims abstract description 79
- 230000008569 process Effects 0.000 title claims abstract description 50
- 239000007788 liquid Substances 0.000 claims abstract description 96
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 239000007791 liquid phase Substances 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 19
- 238000005886 esterification reaction Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000000376 reactant Substances 0.000 claims description 90
- 238000004821 distillation Methods 0.000 claims description 58
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000003112 inhibitor Substances 0.000 claims description 46
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 36
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 34
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 22
- 238000011084 recovery Methods 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 238000009833 condensation Methods 0.000 claims description 19
- 230000005494 condensation Effects 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 18
- 238000011027 product recovery Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000002253 acid Chemical group 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 6
- 238000006845 Michael addition reaction Methods 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 14
- 238000000354 decomposition reaction Methods 0.000 abstract description 9
- 230000001476 alcoholic effect Effects 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 109
- 150000002148 esters Chemical class 0.000 description 23
- 239000006227 byproduct Substances 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- 239000003377 acid catalyst Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 125000005250 alkyl acrylate group Chemical group 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- 229950000688 phenothiazine Drugs 0.000 description 7
- 238000004064 recycling Methods 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 7
- -1 2-ethylhexyl Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 238000010977 unit operation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000013000 chemical inhibitor Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229910052698 phosphorus Chemical group 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 2
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical group CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 description 1
- SXYRTDICSOVQNZ-UHFFFAOYSA-N 1-(2-methoxyethoxy)ethanol Chemical compound COCCOC(C)O SXYRTDICSOVQNZ-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- UAZLASMTBCLJKO-UHFFFAOYSA-N 2-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UAZLASMTBCLJKO-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JJIXPTZEGGPJAZ-UHFFFAOYSA-N prop-2-enoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)C=C JJIXPTZEGGPJAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/12—Formation or introduction of functional groups containing oxygen of carboxylic acid ester groups
-
- 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
- C07C67/30—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
-
- 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)
- 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 |
|---|---|---|---|
| US45074603P | 2003-02-28 | 2003-02-28 | |
| US60/450,746 | 2003-02-28 | ||
| PCT/US2004/004948 WO2004078679A2 (en) | 2003-02-28 | 2004-02-19 | Process for conducting equilibrium-limited reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20050111337A KR20050111337A (ko) | 2005-11-24 |
| KR101136783B1 true KR101136783B1 (ko) | 2012-04-19 |
Family
ID=32962524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057016051A Expired - Lifetime KR101136783B1 (ko) | 2003-02-28 | 2004-02-19 | 평형 제한 반응의 수행방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7569721B2 (enExample) |
| EP (1) | EP1611082B1 (enExample) |
| JP (1) | JP5059400B2 (enExample) |
| KR (1) | KR101136783B1 (enExample) |
| CN (1) | CN100345816C (enExample) |
| BR (1) | BRPI0408043B1 (enExample) |
| DE (1) | DE602004028591D1 (enExample) |
| MX (1) | MX256948B (enExample) |
| WO (1) | WO2004078679A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020106123A1 (ko) * | 2018-11-23 | 2020-05-28 | 지에스칼텍스 주식회사 | 알킬 카르복실산 에스테르의 제조 방법 및 알킬 카르복실산 에스테르의 제조 장치 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10357222A1 (de) * | 2003-12-08 | 2005-06-30 | Basf Ag | Anschlussstutzen für Messgeräte und mit einem solchen Anschlussstutzen versehene Messsonde |
| DE102005043719A1 (de) * | 2005-09-13 | 2007-03-15 | Röhm Gmbh | Vorrichtung und Verfahren für kontinuierlich durchgeführte Gleichgewichtsreaktionen |
| EP2643288B1 (en) | 2010-11-22 | 2016-04-06 | Rohm and Haas Company | Acrylate production process |
| CN105324163B (zh) | 2013-06-28 | 2017-10-31 | 陶氏环球技术有限责任公司 | 用于制造化合物的防积垢蒸馏塔和方法 |
| FR3014870B1 (fr) * | 2013-12-13 | 2015-12-11 | Arkema France | Procede de production d'esters (meth)acryliques |
| US9963419B2 (en) | 2014-10-31 | 2018-05-08 | Dow Global Technologies Llc | Process for in situ water removal from an oxidative esterification reaction using a coupled reactor-distillation system |
| WO2022270495A1 (ja) * | 2021-06-21 | 2022-12-29 | 旭化成株式会社 | 反応システム及び反応方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09110789A (ja) * | 1995-09-28 | 1997-04-28 | Basf Ag | (メタ)アクリル酸のアルキルエステルを連続的に製造するための方法及び装置 |
| WO2000078702A1 (en) | 1999-06-17 | 2000-12-28 | Union Carbide Chemicals & Plastics | Processes for conducting equilibrium-limited reactions |
| JP2002507194A (ja) | 1997-05-20 | 2002-03-05 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー コーポレイション | アクリル酸ブチルの精製方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3776947A (en) * | 1972-10-10 | 1973-12-04 | Nippon Catalytic Chem Ind | Continuous esterification process |
| DE2548561C2 (de) * | 1975-10-30 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung dioctylätherfreien 2-Äthyl- hexylacrylats |
| JPS6317844A (ja) * | 1986-07-09 | 1988-01-25 | Nippon Shokubai Kagaku Kogyo Co Ltd | 不飽和カルボン酸エステルの製造方法 |
| DE4019781A1 (de) * | 1990-06-21 | 1992-01-02 | Basf Ag | Verfahren zur herstellung von monoethylenisch ungesaettigten carbonsaeureestern |
| US5231222A (en) * | 1991-07-02 | 1993-07-27 | Union Carbide Chemicals & Plastics Technology Corporation | Esterification process |
| JP3346822B2 (ja) * | 1993-03-31 | 2002-11-18 | 三菱化学株式会社 | アクリル酸エステル又はメタクリル酸エステルの製造法 |
| FR2721313B1 (fr) * | 1994-06-17 | 1996-07-19 | Atochem Elf Sa | Procédé de fabrication d'acrylates d'alkyle par estérification directe. |
| DE19536191A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| DE19604253A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| DE19604267A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| WO1998052903A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| CN1113849C (zh) * | 1997-10-31 | 2003-07-09 | 国际人造丝公司 | 丙烯酸酯物流的脱硫方法 |
| JP4242964B2 (ja) * | 1999-03-09 | 2009-03-25 | 株式会社日本触媒 | (メタ)アクリル酸および/またはそのエステルの精製方法 |
| JP3782607B2 (ja) * | 1999-04-20 | 2006-06-07 | 株式会社日本触媒 | エステル化物の製造方法 |
| US6482976B1 (en) * | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
-
2004
- 2004-02-19 WO PCT/US2004/004948 patent/WO2004078679A2/en not_active Ceased
- 2004-02-19 KR KR1020057016051A patent/KR101136783B1/ko not_active Expired - Lifetime
- 2004-02-19 MX MXPA05009158 patent/MX256948B/es active IP Right Grant
- 2004-02-19 CN CNB2004800048414A patent/CN100345816C/zh not_active Expired - Fee Related
- 2004-02-19 US US10/544,817 patent/US7569721B2/en active Active
- 2004-02-19 JP JP2006508773A patent/JP5059400B2/ja not_active Expired - Lifetime
- 2004-02-19 DE DE602004028591T patent/DE602004028591D1/de not_active Expired - Lifetime
- 2004-02-19 EP EP04712871A patent/EP1611082B1/en not_active Expired - Lifetime
- 2004-02-19 BR BRPI0408043-2A patent/BRPI0408043B1/pt not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09110789A (ja) * | 1995-09-28 | 1997-04-28 | Basf Ag | (メタ)アクリル酸のアルキルエステルを連続的に製造するための方法及び装置 |
| JP2002507194A (ja) | 1997-05-20 | 2002-03-05 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー コーポレイション | アクリル酸ブチルの精製方法 |
| WO2000078702A1 (en) | 1999-06-17 | 2000-12-28 | Union Carbide Chemicals & Plastics | Processes for conducting equilibrium-limited reactions |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020106123A1 (ko) * | 2018-11-23 | 2020-05-28 | 지에스칼텍스 주식회사 | 알킬 카르복실산 에스테르의 제조 방법 및 알킬 카르복실산 에스테르의 제조 장치 |
| KR20200061219A (ko) * | 2018-11-23 | 2020-06-02 | 지에스칼텍스 주식회사 | 알킬 카르복실산 에스테르의 제조 방법 및 알킬 카르복실산 에스테르의 제조 장치 |
| KR102151747B1 (ko) | 2018-11-23 | 2020-09-03 | 지에스칼텍스 주식회사 | 알킬 카르복실산 에스테르의 제조 방법 및 알킬 카르복실산 에스테르의 제조 장치 |
| US11608307B2 (en) | 2018-11-23 | 2023-03-21 | Gs Caltex Corporation | Method for preparing alkyl carboxylic acid ester and apparatus for preparing alkyl carboxylic acid ester |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050111337A (ko) | 2005-11-24 |
| DE602004028591D1 (de) | 2010-09-23 |
| WO2004078679A3 (en) | 2004-12-09 |
| JP2006519257A (ja) | 2006-08-24 |
| CN1753859A (zh) | 2006-03-29 |
| JP5059400B2 (ja) | 2012-10-24 |
| US7569721B2 (en) | 2009-08-04 |
| MX256948B (es) | 2008-05-07 |
| BRPI0408043A (pt) | 2006-02-14 |
| EP1611082A2 (en) | 2006-01-04 |
| BRPI0408043B1 (pt) | 2015-08-18 |
| EP1611082B1 (en) | 2010-08-11 |
| WO2004078679A2 (en) | 2004-09-16 |
| CN100345816C (zh) | 2007-10-31 |
| US20060094895A1 (en) | 2006-05-04 |
| MXPA05009158A (es) | 2005-10-20 |
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