CS272223B2 - Method of acrylic acid's or metacrylic acid's ester production - Google Patents
Method of acrylic acid's or metacrylic acid's ester production Download PDFInfo
- Publication number
- CS272223B2 CS272223B2 CS875239A CS523987A CS272223B2 CS 272223 B2 CS272223 B2 CS 272223B2 CS 875239 A CS875239 A CS 875239A CS 523987 A CS523987 A CS 523987A CS 272223 B2 CS272223 B2 CS 272223B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- acrylic acid
- acrylic
- reaction solution
- alcohol
- Prior art date
Links
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 49
- 238000000034 method Methods 0.000 title claims description 34
- 150000002148 esters Chemical class 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000002735 metacrylic acids Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 107
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 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 25
- 239000003729 cation exchange resin Substances 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 23
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 18
- 230000032050 esterification Effects 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- -1 2-ethyl Chemical group 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 47
- 239000000243 solution Substances 0.000 description 41
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- KYXHKHDZJSDWEF-LHLOQNFPSA-N CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 Chemical compound CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 KYXHKHDZJSDWEF-LHLOQNFPSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 3
- 239000004808 2-ethylhexylester Substances 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 238000005243 fluidization Methods 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QCZKLKFGDITLCF-UHFFFAOYSA-N 2-ethoxyprop-2-enoic acid Chemical compound CCOC(=C)C(O)=O QCZKLKFGDITLCF-UHFFFAOYSA-N 0.000 description 1
- FECDACOUYKFOOP-UHFFFAOYSA-N 2-ethylhexyl 2-hydroxypropanoate Chemical compound CCCCC(CC)COC(=O)C(C)O FECDACOUYKFOOP-UHFFFAOYSA-N 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- PRWNDQXXTXXMMW-UHFFFAOYSA-N butan-1-ol;prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C PRWNDQXXTXXMMW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 229950007538 pecazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 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
- C07C67/08—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
- 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61159674A JPS6317844A (ja) | 1986-07-09 | 1986-07-09 | 不飽和カルボン酸エステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS523987A2 CS523987A2 (en) | 1990-04-11 |
| CS272223B2 true CS272223B2 (en) | 1991-01-15 |
Family
ID=15698854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS875239A CS272223B2 (en) | 1986-07-09 | 1987-07-09 | Method of acrylic acid's or metacrylic acid's ester production |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4833267A (ko) |
| EP (1) | EP0273060B1 (ko) |
| JP (1) | JPS6317844A (ko) |
| KR (1) | KR910008371B1 (ko) |
| CN (1) | CN1024190C (ko) |
| BR (1) | BR8707412A (ko) |
| CA (1) | CA1290767C (ko) |
| CS (1) | CS272223B2 (ko) |
| DE (1) | DE3773872D1 (ko) |
| HU (1) | HU204024B (ko) |
| MX (1) | MX168277B (ko) |
| WO (1) | WO1988000180A1 (ko) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2884639B2 (ja) * | 1989-11-28 | 1999-04-19 | 三菱瓦斯化学株式会社 | 不飽和カルボン酸エステルの製造法 |
| EP0594008B1 (en) * | 1992-10-22 | 1997-08-13 | Sumitomo Chemical Company, Limited | Process for producing methyl methacrylate |
| FR2721313B1 (fr) * | 1994-06-17 | 1996-07-19 | Atochem Elf Sa | Procédé de fabrication d'acrylates d'alkyle par estérification directe. |
| US6605738B1 (en) | 1996-05-29 | 2003-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butyl acrylate |
| US6015435A (en) * | 1996-10-24 | 2000-01-18 | International Vision, Inc. | Self-centering phakic intraocular lens |
| US5877345A (en) | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| FR2810316B1 (fr) * | 2000-06-19 | 2002-07-26 | Atofina | Preparation d'esters carboxyliques catalysee par un acide sulfonique |
| JP4205841B2 (ja) | 2000-07-31 | 2009-01-07 | 株式会社日本触媒 | 不均一触媒を用いた反応方法およびその反応装置 |
| FR2818639B1 (fr) * | 2000-12-26 | 2003-02-07 | Atofina | Procede perfectionne de fabrication d'esters carboxyliques insatures |
| EP1611082B1 (en) * | 2003-02-28 | 2010-08-11 | Arkema Inc. | Process for conducting equilibrium-limited reactions |
| US20040192957A1 (en) * | 2003-03-31 | 2004-09-30 | Wickens Danita Inez | Method of recovering 2-ethylhexyl alcohol from a mixture comprising 2-ethylhexyl acrylate |
| CN100445261C (zh) * | 2005-05-24 | 2008-12-24 | 上海华谊丙烯酸有限公司 | 一种(甲基)丙烯酸环己酯的合成方法 |
| CN101041621B (zh) * | 2006-11-24 | 2010-12-01 | 中国石油集团工程设计有限责任公司东北分公司 | 制备（甲基）丙烯酸丁酯的方法 |
| CN101735051B (zh) * | 2009-12-10 | 2014-03-19 | 青岛琅琊台集团股份有限公司 | 一种制备衣康酸二异辛酯的方法 |
| CN105073704A (zh) | 2013-03-15 | 2015-11-18 | 3M创新有限公司 | 通过2-辛醇和丙烯酸的酸催化酯化选择性合成丙烯酸2-辛酯 |
| WO2019189259A1 (ja) | 2018-03-28 | 2019-10-03 | 三菱ケミカル株式会社 | 不飽和カルボン酸エステルの製造方法 |
| CN113670774B (zh) * | 2021-07-25 | 2024-11-22 | 安徽虹泰新材料股份有限公司 | 一种用于二聚酸生产的配料检测装置及方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE590370A (ko) * | 1959-04-29 | 1900-01-01 | ||
| US3470238A (en) * | 1964-11-06 | 1969-09-30 | Mitsubishi Petrochemical Co | Process for recovering acrylic and methacrylic ester |
| DE2226829A1 (de) * | 1972-06-02 | 1973-12-20 | Knapsack Ag | Verfahren zur herstellung von acrylsaeureestern |
| JPS5239620B2 (ko) * | 1973-05-14 | 1977-10-06 | ||
| JPS5912102B2 (ja) * | 1976-11-04 | 1984-03-21 | 日本化薬株式会社 | アクリル酸エステルの製造方法 |
| JPS55122740A (en) * | 1979-03-16 | 1980-09-20 | Nippon Kayaku Co Ltd | Preparation of acrylate or methacrylate |
| JPS5967244A (ja) * | 1982-09-27 | 1984-04-16 | Nippon Kayaku Co Ltd | アクリル酸エチルの製造法 |
| US4733004A (en) * | 1986-06-23 | 1988-03-22 | Ashland Oil, Inc. | Continuous esterification of methacrylic acid and product recovery |
-
1986
- 1986-07-09 JP JP61159674A patent/JPS6317844A/ja active Pending
-
1987
- 1987-07-07 HU HU873812A patent/HU204024B/hu not_active IP Right Cessation
- 1987-07-07 US US07/193,523 patent/US4833267A/en not_active Expired - Lifetime
- 1987-07-07 DE DE8787904331T patent/DE3773872D1/de not_active Expired - Lifetime
- 1987-07-07 BR BR8707412A patent/BR8707412A/pt not_active Application Discontinuation
- 1987-07-07 EP EP87904331A patent/EP0273060B1/en not_active Expired - Lifetime
- 1987-07-07 CA CA000541491A patent/CA1290767C/en not_active Expired - Fee Related
- 1987-07-07 KR KR1019880700262A patent/KR910008371B1/ko not_active Expired
- 1987-07-07 WO PCT/JP1987/000482 patent/WO1988000180A1/ja not_active Ceased
- 1987-07-09 MX MX007275A patent/MX168277B/es unknown
- 1987-07-09 CS CS875239A patent/CS272223B2/cs unknown
- 1987-07-09 CN CN87105726A patent/CN1024190C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0273060B1 (en) | 1991-10-16 |
| MX168277B (es) | 1993-05-14 |
| JPS6317844A (ja) | 1988-01-25 |
| CA1290767C (en) | 1991-10-15 |
| BR8707412A (pt) | 1988-11-01 |
| HU204024B (en) | 1991-11-28 |
| HUT48863A (en) | 1989-07-28 |
| KR910008371B1 (ko) | 1991-10-12 |
| US4833267A (en) | 1989-05-23 |
| CN1024190C (zh) | 1994-04-13 |
| WO1988000180A1 (fr) | 1988-01-14 |
| KR880701702A (ko) | 1988-11-04 |
| EP0273060A4 (en) | 1988-11-09 |
| CN87105726A (zh) | 1988-07-06 |
| CS523987A2 (en) | 1990-04-11 |
| DE3773872D1 (de) | 1991-11-21 |
| EP0273060A1 (en) | 1988-07-06 |
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