KR101985985B1 - 직접 에스테르화에 의한 2-옥틸 아크릴레이트의 제조 방법 - Google Patents
직접 에스테르화에 의한 2-옥틸 아크릴레이트의 제조 방법 Download PDFInfo
- Publication number
- KR101985985B1 KR101985985B1 KR1020147014941A KR20147014941A KR101985985B1 KR 101985985 B1 KR101985985 B1 KR 101985985B1 KR 1020147014941 A KR1020147014941 A KR 1020147014941A KR 20147014941 A KR20147014941 A KR 20147014941A KR 101985985 B1 KR101985985 B1 KR 101985985B1
- Authority
- KR
- South Korea
- Prior art keywords
- stream
- reaction
- rich
- octanol
- octyl acrylate
- 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.)
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- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 20
- 230000032050 esterification Effects 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 7
- 238000004821 distillation Methods 0.000 claims abstract description 55
- 238000000746 purification Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000010924 continuous production Methods 0.000 claims abstract description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 117
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 239000011541 reaction mixture Substances 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 30
- 239000008346 aqueous phase Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000003112 inhibitor Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 22
- 239000010408 film Substances 0.000 claims description 22
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- 238000000926 separation method Methods 0.000 claims description 20
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 19
- 239000012074 organic phase Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000006227 byproduct Substances 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 14
- 239000012535 impurity Substances 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 230000000284 resting effect Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 230000003134 recirculating effect Effects 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000011552 falling film Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 16
- 239000003377 acid catalyst Substances 0.000 abstract description 13
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract description 9
- 238000009776 industrial production Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000000605 extraction Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- -1 polyol acrylates Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material 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
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000002998 adhesive polymer Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
Images
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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1159983A FR2982258B1 (fr) | 2011-11-04 | 2011-11-04 | Procede de production d'acrylate de 2-octyle par esterification directe |
| FR1159983 | 2011-11-04 | ||
| FR1256457 | 2012-07-05 | ||
| FR1256457A FR2982259B1 (fr) | 2011-11-04 | 2012-07-05 | Procede de production d'acrylate de 2-octyle par esterification directe |
| PCT/FR2012/052502 WO2013064775A1 (fr) | 2011-11-04 | 2012-10-30 | Procédé de production d'acrylate de 2-octyle par estérification directe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140091573A KR20140091573A (ko) | 2014-07-21 |
| KR101985985B1 true KR101985985B1 (ko) | 2019-06-04 |
Family
ID=46650816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147014941A Active KR101985985B1 (ko) | 2011-11-04 | 2012-10-30 | 직접 에스테르화에 의한 2-옥틸 아크릴레이트의 제조 방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9403750B2 (enExample) |
| EP (1) | EP2773608B1 (enExample) |
| JP (1) | JP6043800B2 (enExample) |
| KR (1) | KR101985985B1 (enExample) |
| CN (1) | CN104024210B (enExample) |
| BR (1) | BR112014010416B1 (enExample) |
| FR (2) | FR2982258B1 (enExample) |
| MY (1) | MY166880A (enExample) |
| SG (1) | SG11201402013YA (enExample) |
| WO (1) | WO2013064775A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3024143B1 (fr) * | 2014-07-28 | 2016-07-15 | Arkema France | Procede perfectionne de fabrication de (meth)acrylates d'alkyle |
| JP2019524999A (ja) | 2016-07-18 | 2019-09-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 縮合反応のための低腐食性アルカンスルホン酸 |
| KR102745052B1 (ko) * | 2019-09-27 | 2024-12-23 | 주식회사 엘지화학 | 디에스터계 물질의 정제 유닛 및 이를 포함하는 디에스터계 물질의 정제 시스템 |
| KR102683132B1 (ko) * | 2019-09-27 | 2024-07-10 | 주식회사 엘지화학 | 디에스터계 물질의 정제 유닛 및 이를 포함하는 디에스터계 물질의 정제 시스템 |
| CN113045421A (zh) * | 2019-12-26 | 2021-06-29 | 江苏怡达化学股份有限公司 | 一种己二酸二异丙酯的制备工艺及其设备 |
| CN113045411A (zh) * | 2019-12-26 | 2021-06-29 | 江苏怡达化学股份有限公司 | 一种乙酸正戊酯的制备工艺及其设备 |
| CN113045412A (zh) * | 2019-12-26 | 2021-06-29 | 江苏怡达化学股份有限公司 | 一种己二酸二元酯的制备工艺及其设备 |
| FI4436948T3 (fi) | 2021-11-25 | 2025-10-23 | Basf Se | Menetelmä 2-oktyyli(met)akrylaatin valmistamiseksi |
| EP4335878A1 (en) | 2022-09-07 | 2024-03-13 | Arkema France | Copolymers, compositions and uses thereof |
| KR20250086752A (ko) * | 2022-11-18 | 2025-06-13 | 가부시키가이샤 닛폰 쇼쿠바이 | (메타)아크릴산 에스테르의 제조방법 |
| WO2023249129A2 (ja) | 2022-11-18 | 2023-12-28 | 株式会社日本触媒 | （メタ）アクリル酸エステルの製造方法 |
| EP4638409A1 (de) | 2022-12-21 | 2025-10-29 | Basf Se | Weichmacher-verbindung |
| WO2024153687A1 (de) | 2023-01-19 | 2024-07-25 | Basf Se | Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern |
| FI130915B1 (en) * | 2023-05-22 | 2024-05-27 | Chempolis Oy | Heteroazeotrope extractive distillation process device and method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010506979A (ja) * | 2006-10-13 | 2010-03-04 | スリーエム イノベイティブ プロパティズ カンパニー | ２−オクチル（メタ）アクリレート接着剤組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19604253A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| DE69812682T2 (de) | 1997-10-31 | 2003-12-18 | Celanese International Corp., Dallas | Entfernung von schwefel aus einem acrylatstrom |
| US6084122A (en) | 1997-10-31 | 2000-07-04 | Celanese International Corporation | Sulfur removal process from an acrylate waste stream |
| DE19851984A1 (de) * | 1998-11-11 | 2000-05-18 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| CN1090610C (zh) * | 2000-12-06 | 2002-09-11 | 北京化学工业集团有限责任公司东方化工厂 | 丙烯酸辛酯的生产方法 |
| DE102005010588A1 (de) * | 2005-03-08 | 2006-05-24 | Basf Ag | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure |
| JP4160087B2 (ja) * | 2006-07-11 | 2008-10-01 | 株式会社日本触媒 | アクリル酸エステルの製造方法 |
| CN102428065B (zh) * | 2009-05-15 | 2014-02-26 | 株式会社日本触媒 | 制备(甲基)丙烯酸的方法 |
-
2011
- 2011-11-04 FR FR1159983A patent/FR2982258B1/fr not_active Expired - Fee Related
-
2012
- 2012-07-05 FR FR1256457A patent/FR2982259B1/fr not_active Expired - Fee Related
- 2012-10-30 JP JP2014539381A patent/JP6043800B2/ja active Active
- 2012-10-30 KR KR1020147014941A patent/KR101985985B1/ko active Active
- 2012-10-30 SG SG11201402013YA patent/SG11201402013YA/en unknown
- 2012-10-30 EP EP12794403.1A patent/EP2773608B1/fr active Active
- 2012-10-30 MY MYPI2014001293A patent/MY166880A/en unknown
- 2012-10-30 BR BR112014010416-6A patent/BR112014010416B1/pt active IP Right Grant
- 2012-10-30 CN CN201280053578.2A patent/CN104024210B/zh active Active
- 2012-10-30 WO PCT/FR2012/052502 patent/WO2013064775A1/fr not_active Ceased
- 2012-10-30 US US14/354,986 patent/US9403750B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010506979A (ja) * | 2006-10-13 | 2010-03-04 | スリーエム イノベイティブ プロパティズ カンパニー | ２−オクチル（メタ）アクリレート接着剤組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2982258A1 (fr) | 2013-05-10 |
| US20150299093A1 (en) | 2015-10-22 |
| JP2014534972A (ja) | 2014-12-25 |
| SG11201402013YA (en) | 2014-11-27 |
| CN104024210B (zh) | 2015-12-02 |
| EP2773608A1 (fr) | 2014-09-10 |
| FR2982259B1 (fr) | 2014-06-06 |
| FR2982258B1 (fr) | 2013-11-15 |
| WO2013064775A1 (fr) | 2013-05-10 |
| FR2982259A1 (fr) | 2013-05-10 |
| CN104024210A (zh) | 2014-09-03 |
| JP6043800B2 (ja) | 2016-12-14 |
| BR112014010416A2 (pt) | 2017-04-25 |
| MY166880A (en) | 2018-07-24 |
| KR20140091573A (ko) | 2014-07-21 |
| US9403750B2 (en) | 2016-08-02 |
| BR112014010416B1 (pt) | 2021-06-29 |
| EP2773608B1 (fr) | 2015-10-21 |
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