JP6606496B2 - 膜分離の脱水による(メタ)アクリル酸エステルの精製 - Google Patents
膜分離の脱水による(メタ)アクリル酸エステルの精製 Download PDFInfo
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- JP6606496B2 JP6606496B2 JP2016538618A JP2016538618A JP6606496B2 JP 6606496 B2 JP6606496 B2 JP 6606496B2 JP 2016538618 A JP2016538618 A JP 2016538618A JP 2016538618 A JP2016538618 A JP 2016538618A JP 6606496 B2 JP6606496 B2 JP 6606496B2
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- 239000012528 membrane Substances 0.000 title claims description 74
- 238000000926 separation method Methods 0.000 title claims description 47
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 35
- 230000018044 dehydration Effects 0.000 title claims description 18
- 238000006297 dehydration reaction Methods 0.000 title claims description 18
- 238000000746 purification Methods 0.000 title claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 239000006227 byproduct Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- -1 acrylic ester Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000004062 sedimentation Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 7
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000005373 pervaporation Methods 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 2
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 description 9
- 238000010924 continuous production Methods 0.000 description 9
- 238000009434 installation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012466 permeate Substances 0.000 description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- 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 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000010923 batch production Methods 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- KUZUWYWVINGZKL-UHFFFAOYSA-N octan-2-yl 2-methylprop-2-enoate Chemical compound CCCCCCC(C)OC(=O)C(C)=C KUZUWYWVINGZKL-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/145—One step being separation by permeation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/02—Inorganic material
- B01D71/028—Molecular sieves
- B01D71/0281—Zeolites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/38—Polyalkenylalcohols; Polyalkenylesters; Polyalkenylethers; Polyalkenylaldehydes; Polyalkenylketones; Polyalkenylacetals; Polyalkenylketals
- B01D71/381—Polyvinylalcohol
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/26—Further operations combined with membrane separation processes
- B01D2311/2669—Distillation
-
- 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)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
試験は、170cm2の膜表面積を有するスルザー膜分離パイロット上で行った。試験された膜は、参照Pervap(R) 1201を用いたポリビニルアルコールに基づく親水性膜である。
試験は、170cm2の膜表面積を有するスルザー膜分離パイロット上で行った。試験された膜は、参照Pervap(R) 4060を用いた疎水性膜である。
試験は、170cm2の膜表面積を有するスルザー膜分離パイロット上で行った。試験された膜は、参照Pervap(R) 1201を用いたポリビニルアルコールに基づく親水性膜である。
Claims (9)
- 触媒の存在下で4から10個の炭素原子を含む直鎖または分岐のアルコールとの(メタ)アクリル酸の直接エステル化により、4から10個の炭素原子を有する直鎖または分岐のアルキル鎖を有するアルキル(メタ)アクリレートを製造する方法であって、所望のエステル、未反応の酸およびアルコール、軽質副生成物および重質副生成物を含む反応混合物の形成をもたらし、該混合物は精製されたアルキル(メタ)アクリレートを得るために、分離手段により精製処理を受け、
該精製処理はそれが、精製された(メタ)アクリル酸エステルの回収をもたらす最終蒸留に供される流れに適用される膜分離による脱水工程を含み、
該精製処理が、
i)反応器からの反応流を中和した後に水を除去する沈降タンクに供給する工程と、
ii)沈降タンクで水が除去された流れを洗浄塔に供給する工程と、
iii)洗浄塔で洗浄された流れを蒸留塔に供給する工程と、
iv)蒸留塔の頂部からの流れを反応にリサイクルする工程と
を含み、
洗浄塔で洗浄された流れが、蒸留塔に供給される前に水を除去するするために膜分離脱水装置に供給される、
ことを特徴とする該製造方法。 - アルコールが、ブタノール、2−エチルヘキサノールまたは2−オクタノールであることを特徴とする請求項1に記載の方法。
- 酸がアクリル酸であることを特徴とする請求項1または2に記載の方法。
- 膜分離による脱水が、パーベーパレーションまたは蒸気透過による脱水であることを特徴とする請求項1から3のいずれか一項に記載の方法。
- 膜分離が、無機膜上または親水性高分子膜上の分離、または疎水性高分子膜上の分離であることを特徴とする請求項1から4のいずれか一項に記載の方法。
- 膜分離が、ゼオライト上またはポリビニルアルコールに基づく親水性膜上で実施されることを特徴とする請求項5に記載の方法。
- 連続、半連続、またはバッチ式タイプであることを特徴とする請求項1から6のいずれか一項に記載の方法。
- 膜分離により処理される流れは、50から70重量%の(メタ)アクリル酸エステル、20から30重量%のアルコール、0から12重量%の(メタ)アクリル酸、および3から12重量%の水を含むことを特徴とする請求項1から7のいずれか一項に記載の方法。
- ブチルアクリレートを製造するための半連続タイプであることを特徴とする請求項1から8のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1362560A FR3014870B1 (fr) | 2013-12-13 | 2013-12-13 | Procede de production d'esters (meth)acryliques |
FR1362560 | 2013-12-13 | ||
PCT/FR2014/053223 WO2015086978A1 (fr) | 2013-12-13 | 2014-12-09 | Purification d'esters (meth)acryliques par déshydratation par séparation membranaire |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017502942A JP2017502942A (ja) | 2017-01-26 |
JP2017502942A5 JP2017502942A5 (ja) | 2018-01-11 |
JP6606496B2 true JP6606496B2 (ja) | 2019-11-13 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP2016538618A Active JP6606496B2 (ja) | 2013-12-13 | 2014-12-09 | 膜分離の脱水による(メタ)アクリル酸エステルの精製 |
Country Status (5)
Country | Link |
---|---|
US (1) | US10647657B2 (ja) |
EP (1) | EP3079797B1 (ja) |
JP (1) | JP6606496B2 (ja) |
FR (1) | FR3014870B1 (ja) |
WO (1) | WO2015086978A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017058851A1 (en) * | 2015-09-30 | 2017-04-06 | Dow Global Technologies Llc | Process for hybrid distillation and membrane separation of organic components from water in making eha (ethylhexyl-acrylate) |
FR3048697B1 (fr) | 2016-03-10 | 2019-09-27 | Arkema France | Procede de production d'esters (meth)acryliques |
CN106748762A (zh) * | 2016-11-15 | 2017-05-31 | 惠州市长润发涂料有限公司 | 一种二丙二醇二丙烯酸酯的制备方法 |
CN106748761A (zh) * | 2016-11-15 | 2017-05-31 | 惠州市长润发涂料有限公司 | 一种三羟甲基丙烷三丙烯酸酯的制备方法 |
JP7537681B2 (ja) | 2020-09-15 | 2024-08-21 | 株式会社日本触媒 | アクリル酸の製造方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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GB770551A (en) * | 1953-08-27 | 1957-03-20 | Celanese Corp | Continuous esterification process |
DE4401405A1 (de) * | 1994-01-19 | 1995-07-20 | Huels Chemische Werke Ag | Verfahren zur Entwässerung von Acrylsäure |
WO1998052904A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butylacrylate |
JP2002047213A (ja) * | 2000-08-03 | 2002-02-12 | Mitsui Eng & Shipbuild Co Ltd | エステル化反応装置およびこれを用いたエステル製造方法 |
US6755975B2 (en) * | 2002-06-12 | 2004-06-29 | Membrane Technology And Research, Inc. | Separation process using pervaporation and dephlegmation |
DE10301007A1 (de) * | 2003-01-13 | 2004-07-22 | Röhm GmbH & Co. KG | Verbessertes Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten mit mehrfacher Katalysatorrezyklierung. |
WO2004078679A2 (en) * | 2003-02-28 | 2004-09-16 | Union Carbide Chemicals & Plastics Technology Corporation | Process for conducting equilibrium-limited reactions |
US8002874B2 (en) * | 2007-03-06 | 2011-08-23 | Membrane Technology And Research, Inc. | Liquid-phase and vapor-phase dehydration of organic/water solutions |
US8496831B2 (en) * | 2007-08-30 | 2013-07-30 | Membrane Technology And Research, Inc. | Dehydration processes using membranes with hydrophobic coating |
FR2980475B1 (fr) * | 2011-09-27 | 2013-08-30 | Arkema France | Procede de production d'esters acryliques |
US8829251B2 (en) * | 2011-11-18 | 2014-09-09 | Celanese International Corporation | Liquid esterification method to produce ester feed for hydrogenolysis |
-
2013
- 2013-12-13 FR FR1362560A patent/FR3014870B1/fr active Active
-
2014
- 2014-12-09 US US15/102,921 patent/US10647657B2/en active Active
- 2014-12-09 WO PCT/FR2014/053223 patent/WO2015086978A1/fr active Application Filing
- 2014-12-09 EP EP14827479.8A patent/EP3079797B1/fr active Active
- 2014-12-09 JP JP2016538618A patent/JP6606496B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
US10647657B2 (en) | 2020-05-12 |
EP3079797A1 (fr) | 2016-10-19 |
FR3014870A1 (fr) | 2015-06-19 |
FR3014870B1 (fr) | 2015-12-11 |
JP2017502942A (ja) | 2017-01-26 |
WO2015086978A9 (fr) | 2018-05-03 |
EP3079797B1 (fr) | 2018-08-15 |
WO2015086978A1 (fr) | 2015-06-18 |
US20160376217A1 (en) | 2016-12-29 |
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