JP4561137B2 - (メタ)アクリル酸エステルの製造方法 - Google Patents
(メタ)アクリル酸エステルの製造方法 Download PDFInfo
- Publication number
- JP4561137B2 JP4561137B2 JP2004080725A JP2004080725A JP4561137B2 JP 4561137 B2 JP4561137 B2 JP 4561137B2 JP 2004080725 A JP2004080725 A JP 2004080725A JP 2004080725 A JP2004080725 A JP 2004080725A JP 4561137 B2 JP4561137 B2 JP 4561137B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- meth
- acid ester
- unreacted
- reaction
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 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 13
- 239000003729 cation exchange resin Substances 0.000 claims description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 9
- 238000011084 recovery Methods 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004821 distillation Methods 0.000 description 19
- 238000012856 packing Methods 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- -1 acrylic ester Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- NIUAGEVCVWHMTA-UHFFFAOYSA-N 5-(4-iodophenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(I)=CC=2)=CC(C(F)(F)F)=N1 NIUAGEVCVWHMTA-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
角錐体状など従来から使用されている充填物の他に、近年、高性能充填物として注目されている特殊形状を有する規則的または不規則的充填物が挙げられる。
ポリマー状重質分としては、ポリ(メタ)アクリル酸、ポリ(メタ)アクリル酸エステル、ミカエル付加型高分子ポリエステル等である。また、固形物としては鉄錆などのスラッジ類も含まれる。固形物を分離する際の温度は、上記の様なポリマー状重質分の固体状態の維持を図る観点から、通常50〜90℃である。
図1に示した方法に従ってアクリル酸メチルエステルを連続的に製造した。触媒としては三菱化学製の強酸性陽イオン交換樹脂「PK−216」を固定床として使用した。
また、固形物分離手段(3)には透過粒径3μmのカートリッジフィルターを使用した。
実施例1において、フィルターを設置しないこと以外は、実施例1と全く同一条件で連続運転を実施した。その結果、1.1ケ月経過時点でアクリル酸の転化率は運転開始当初より3.7%低下しており、精製系の能力の限界に近づいたため、定期修理時に触媒を交換した。
2:蒸留塔
3:固形物分離手段
Claims (3)
- (メタ)アクリル酸と炭素数1〜4のアルコールとを強酸性陽イオン交換樹脂触媒の存在下にエステル化反応させて(メタ)アクリル酸エステルを得る反応工程と、当該反応工程で得られた反応液から未反応(メタ)アクリル酸を分離する回収工程とを包含し、上記の反応工程に未反応(メタ)アクリル酸を循環することより成る(メタ)アクリル酸エステルの製造方法において、反応工程に循環される未反応(メタ)アクリル酸中の、ポリマー状重質分および樹脂破砕物を含む固形物の分離を、透過粒径が1〜10μmの濾過器により50〜90℃の温度で行うことを特徴とする(メタ)アクリル酸エステルの製造方法。
- 濾過器がフィルターである請求項1に記載の製造方法。
- (メタ)アクリル酸エステルが、アクリル酸メチル、アクリル酸エチル又はメタクリル酸メチルである請求項1又は2に記載の製造方法。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004080725A JP4561137B2 (ja) | 2004-03-19 | 2004-03-19 | (メタ)アクリル酸エステルの製造方法 |
ES04788221T ES2351216T3 (es) | 2004-03-19 | 2004-09-28 | Procedimiento para producir éster (met)acrílico. |
AU2004233468A AU2004233468A1 (en) | 2004-03-19 | 2004-09-28 | Process for producing (meth) acrylic esters |
PCT/JP2004/014154 WO2005090279A1 (ja) | 2004-03-19 | 2004-09-28 | (メタ)アクリル酸エステルの製造方法 |
BRPI0405627-2A BRPI0405627B1 (pt) | 2004-03-19 | 2004-09-28 | Processo para a produção de ésteres (met)acrílicos |
RU2004136602/04A RU2353611C2 (ru) | 2004-03-19 | 2004-09-28 | Способ получения (мет)акриловых сложных эфиров |
ZA200409731A ZA200409731B (en) | 2004-03-19 | 2004-09-28 | Process for producing (meth) acrylic esters |
CN200480000356.XA CN1697822B (zh) | 2004-03-19 | 2004-09-28 | 制备(甲基)丙烯酸酯的方法 |
EP04788221A EP1726579B1 (en) | 2004-03-19 | 2004-09-28 | Process for producing (meth)acrylic ester |
US11/005,308 US20050209481A1 (en) | 2004-03-19 | 2004-12-07 | Process for producing (meth) acrylic esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004080725A JP4561137B2 (ja) | 2004-03-19 | 2004-03-19 | (メタ)アクリル酸エステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005263731A JP2005263731A (ja) | 2005-09-29 |
JP4561137B2 true JP4561137B2 (ja) | 2010-10-13 |
Family
ID=34993610
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004080725A Expired - Lifetime JP4561137B2 (ja) | 2004-03-19 | 2004-03-19 | (メタ)アクリル酸エステルの製造方法 |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1726579B1 (ja) |
JP (1) | JP4561137B2 (ja) |
CN (1) | CN1697822B (ja) |
AU (1) | AU2004233468A1 (ja) |
BR (1) | BRPI0405627B1 (ja) |
ES (1) | ES2351216T3 (ja) |
RU (1) | RU2353611C2 (ja) |
WO (1) | WO2005090279A1 (ja) |
ZA (1) | ZA200409731B (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102675098A (zh) * | 2012-05-29 | 2012-09-19 | 江门谦信化工发展有限公司 | 一种丙烯酸丁酯连续生产新工艺 |
FR3012447B1 (fr) * | 2013-10-29 | 2017-01-20 | Arkema France | Procede de production d'esters (meth)acryliques legers |
KR101733663B1 (ko) * | 2014-08-18 | 2017-05-10 | 한국화학연구원 | 폴리올 아크릴레이트 에스테르의 제조 공정에서의 미반응 아크릴산 회수 방법 |
LT3194357T (lt) | 2014-09-19 | 2019-09-25 | Public Joint Stock Company "Sibur Holding" | Karboksirūgščių esterių gavimo būdas, naudojant titano turintį katalizatorių |
JP2019172665A (ja) | 2018-03-28 | 2019-10-10 | 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 |
CN109293512A (zh) * | 2018-12-10 | 2019-02-01 | 杭州若水化学科技有限公司 | 丙烯酸酯类产品生产装置 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4733004A (en) * | 1986-06-23 | 1988-03-22 | Ashland Oil, Inc. | Continuous esterification of methacrylic acid and product recovery |
JPH03240753A (ja) * | 1990-02-19 | 1991-10-28 | Tosoh Corp | メタクリル酸エステルの製造方法 |
JP4558870B2 (ja) * | 1999-11-08 | 2010-10-06 | 株式会社日本触媒 | 塔式処理方法および装置 |
-
2004
- 2004-03-19 JP JP2004080725A patent/JP4561137B2/ja not_active Expired - Lifetime
- 2004-09-28 ES ES04788221T patent/ES2351216T3/es active Active
- 2004-09-28 WO PCT/JP2004/014154 patent/WO2005090279A1/ja not_active Application Discontinuation
- 2004-09-28 ZA ZA200409731A patent/ZA200409731B/en unknown
- 2004-09-28 AU AU2004233468A patent/AU2004233468A1/en not_active Abandoned
- 2004-09-28 BR BRPI0405627-2A patent/BRPI0405627B1/pt active IP Right Grant
- 2004-09-28 CN CN200480000356.XA patent/CN1697822B/zh active Active
- 2004-09-28 RU RU2004136602/04A patent/RU2353611C2/ru active
- 2004-09-28 EP EP04788221A patent/EP1726579B1/en active Active
Also Published As
Publication number | Publication date |
---|---|
EP1726579A4 (en) | 2007-12-26 |
CN1697822A (zh) | 2005-11-16 |
RU2004136602A (ru) | 2006-03-20 |
WO2005090279A1 (ja) | 2005-09-29 |
EP1726579B1 (en) | 2010-09-01 |
CN1697822B (zh) | 2010-05-05 |
AU2004233468A1 (en) | 2005-10-27 |
EP1726579A1 (en) | 2006-11-29 |
ZA200409731B (en) | 2007-04-25 |
BRPI0405627A (pt) | 2006-02-21 |
BRPI0405627B1 (pt) | 2014-08-05 |
JP2005263731A (ja) | 2005-09-29 |
ES2351216T3 (es) | 2011-02-01 |
RU2353611C2 (ru) | 2009-04-27 |
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