TWI468383B - 由甘油製造丙烯醛及／或丙烯酸的方法 - Google Patents
由甘油製造丙烯醛及／或丙烯酸的方法 Download PDFInfo
- Publication number
- TWI468383B TWI468383B TW99143718A TW99143718A TWI468383B TW I468383 B TWI468383 B TW I468383B TW 99143718 A TW99143718 A TW 99143718A TW 99143718 A TW99143718 A TW 99143718A TW I468383 B TWI468383 B TW I468383B
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- Prior art keywords
- acrolein
- stage
- fluid
- phase
- aqueous phase
- Prior art date
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 305
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 258
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 74
- 238000000034 method Methods 0.000 title claims description 73
- 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 72
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 239000012530 fluid Substances 0.000 claims description 175
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 141
- 239000007789 gas Substances 0.000 claims description 120
- 235000011187 glycerol Nutrition 0.000 claims description 108
- 238000006297 dehydration reaction Methods 0.000 claims description 89
- 238000007254 oxidation reaction Methods 0.000 claims description 80
- 229910052760 oxygen Inorganic materials 0.000 claims description 79
- 239000012071 phase Substances 0.000 claims description 76
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 58
- 239000001301 oxygen Substances 0.000 claims description 58
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229920000247 superabsorbent polymer Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C47/22—Acryaldehyde; Methacryaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00004—Scale aspects
- B01J2219/00006—Large-scale industrial plants
-
- 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
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B30/00—Energy efficient heating, ventilation or air conditioning [HVAC]
- Y02B30/52—Heat recovery pumps, i.e. heat pump based systems or units able to transfer the thermal energy from one area of the premises or part of the facilities to a different one, improving the overall efficiency
-
- 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
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0958937A FR2953830B1 (fr) | 2009-12-14 | 2009-12-14 | Procede de fabrication d'acroleine et/ou d'acide acrylique a partir de glycerol |
| US31423410P | 2010-03-16 | 2010-03-16 |
Publications (2)
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|---|---|
| TW201136887A TW201136887A (en) | 2011-11-01 |
| TWI468383B true TWI468383B (zh) | 2015-01-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW99143718A TWI468383B (zh) | 2009-12-14 | 2010-12-14 | 由甘油製造丙烯醛及／或丙烯酸的方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8609904B2 (enExample) |
| EP (1) | EP2513027B1 (enExample) |
| JP (1) | JP5784627B2 (enExample) |
| KR (1) | KR101802543B1 (enExample) |
| CN (1) | CN102639478B (enExample) |
| BR (1) | BR112012014147A2 (enExample) |
| FR (1) | FR2953830B1 (enExample) |
| IN (1) | IN2012DN04890A (enExample) |
| MY (1) | MY157406A (enExample) |
| SG (1) | SG181693A1 (enExample) |
| TW (1) | TWI468383B (enExample) |
| WO (1) | WO2011080447A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2953829B1 (fr) * | 2009-12-14 | 2011-12-09 | Arkema France | Procede de fabrication d'acroleine et/ou d'acide acrylique a partir de glycerol |
| CN103827070A (zh) * | 2011-09-29 | 2014-05-28 | 株式会社日本触媒 | 丙烯醛、丙烯酸及其衍生物的制备方法 |
| JP2013075842A (ja) * | 2011-09-29 | 2013-04-25 | Nippon Shokubai Co Ltd | アクロレインの製造方法、アクリル酸の製造方法、および親水性樹脂の製造方法 |
| KR102044428B1 (ko) | 2015-12-23 | 2019-12-02 | 주식회사 엘지화학 | 글리세린으로부터 아크릴산의 제조방법 |
| CN106622040B (zh) * | 2017-01-18 | 2019-10-18 | 中国科学院过程工程研究所 | 一种采用移动床反应器制备丙烯酸和/或丙烯酸酯的系统及其制备方法 |
| CN109304190B (zh) * | 2017-07-28 | 2021-06-18 | 中国石油化工股份有限公司 | 甘油制丙烯醛用催化剂 |
| CN108409044B (zh) | 2018-04-04 | 2019-04-16 | 蓝星安迪苏南京有限公司 | 用于处理丙烯醛反应器废水的方法及装置 |
| FR3100243B1 (fr) | 2019-08-28 | 2021-07-30 | Arkema France | Elimination du formaldehyde dans les eaux usees par un traitement d'oxydation |
| TWI823017B (zh) * | 2020-07-22 | 2023-11-21 | 華懋科技股份有限公司 | 節能型雙轉輪高濃度冷側旁通過溫控制系統及其方法 |
| TWI756748B (zh) | 2020-07-22 | 2022-03-01 | 華懋科技股份有限公司 | 節能型雙轉輪冷側旁通過溫控制系統及其方法 |
| US12031719B2 (en) | 2020-07-22 | 2024-07-09 | Desiccant Technology Corporation | System and method to prevent the oxidizer overheating using cold side bypass during high input for a VOCS treatment system with series rotor |
| KR102690125B1 (ko) * | 2020-12-03 | 2024-07-30 | 주식회사 엘지화학 | 아크릴산의 제조 공정 |
| KR102690124B1 (ko) * | 2020-12-03 | 2024-07-30 | 주식회사 엘지화학 | 아크릴산의 제조 공정 |
| BR102020026453A2 (pt) * | 2020-12-22 | 2022-07-05 | Petróleo Brasileiro S.A. - Petrobras | Método de conversão catalítica de glicerina em produtos de alto valor agregado e uso |
| CN114653306B (zh) * | 2022-03-14 | 2023-07-21 | 北京奥科瑞丰新能源股份有限公司 | 一种用于糠醛生产的具有自动加碱机构的中和反应釜 |
| US20250243132A1 (en) * | 2024-01-31 | 2025-07-31 | Gevo, Inc. | Systems and Processes for Catalytic Conversion of Bio-Based Materials |
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| US6348638B1 (en) * | 1996-06-20 | 2002-02-19 | Basf Aktiengesellschaft | Method for removing by-products obtained when producing acrylic acid or methacrylic acids |
| FR2909999A1 (fr) * | 2006-12-19 | 2008-06-20 | Arkema France | Procede de preparation d'acide acrylique a partir de glycerol |
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| FR695931A (fr) | 1929-06-15 | 1930-12-23 | Schering Kahlbaum Ag | Procédé de fabrication d'acroléine |
| US2558520A (en) | 1948-01-29 | 1951-06-26 | Us Ind Chemicals Inc | Production of acrolein from glycerol |
| US3433840A (en) | 1966-12-29 | 1969-03-18 | Sumitomo Chemical Co | Process for recovering acrolein by quenching,absorption and plural distillation |
| BE786398A (fr) | 1971-07-21 | 1973-01-18 | Basf Ag | Procede de preparation de l'acide acrylique anhydre |
| DE4238493C1 (de) | 1992-11-14 | 1994-04-21 | Degussa | Verfahren zur Herstellung von Acrolein und dessen Verwendung |
| DE4308087C2 (de) | 1993-03-13 | 1997-02-06 | Basf Ag | Verfahren zur Abtrennung von Acrylsäure aus den Reaktionsgasen der katalytischen Oxidation von Propylen und/oder Acrolein |
| JPH07133249A (ja) * | 1993-09-17 | 1995-05-23 | Daicel Chem Ind Ltd | 高純度酢酸の製造方法 |
| GB9400081D0 (en) * | 1994-01-05 | 1994-03-02 | Dow Deutschland Inc | Process for producing chlorohydrins |
| TW476746B (en) | 1997-07-23 | 2002-02-21 | Shell Int Research | Hydrogenolysis of glycerol |
| FR2775685B1 (fr) * | 1998-03-05 | 2000-12-29 | Rhone Poulenc Fibres | Procede de separation et de purification de l'acide adipique |
| DE19848208A1 (de) | 1998-10-20 | 2000-04-27 | Deg Engineering Gmbh | Reaktor für die katalytische Umsetzung von Reaktionsmedien, insbesondere von gasförmigen Reaktionsmedien |
| US6303826B1 (en) * | 2000-01-19 | 2001-10-16 | Sunoco, Inc. (R&M) | Method for purification of acetone |
| DE10019381B4 (de) | 2000-04-19 | 2006-05-18 | Daun, Klaus-Dieter, Dipl.-Ing. | Reaktor für die katalytische Umsetzung von Reaktionsmedien, insbesondere von gasförmigen Reaktionsmedien |
| US6515187B1 (en) | 2001-10-03 | 2003-02-04 | Atofina Chemicals, Inc. | Process for recovering acrolein or propionaldehyde from dilute aqueous streams |
| FR2835831B1 (fr) | 2002-02-12 | 2006-09-01 | Aventis Animal Nutrition Sa | Procede de purification de l'acroleine |
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| US7268254B2 (en) | 2003-07-24 | 2007-09-11 | Basf Aktiengesellschaft | Preparation of (meth)acrolein and/or (meth)acrylic acid by heterogeneously catalyzed partial oxidation of C3 and/or C4 precursor compounds in a reactor having thermoplate modules |
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-
2009
- 2009-12-14 FR FR0958937A patent/FR2953830B1/fr not_active Expired - Fee Related
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2010
- 2010-12-13 CN CN201080056513.4A patent/CN102639478B/zh active Active
- 2010-12-13 JP JP2012542608A patent/JP5784627B2/ja not_active Expired - Fee Related
- 2010-12-13 US US13/515,047 patent/US8609904B2/en active Active
- 2010-12-13 BR BR112012014147A patent/BR112012014147A2/pt not_active Application Discontinuation
- 2010-12-13 WO PCT/FR2010/052692 patent/WO2011080447A1/fr not_active Ceased
- 2010-12-13 IN IN4890DEN2012 patent/IN2012DN04890A/en unknown
- 2010-12-13 MY MYPI2012002657A patent/MY157406A/en unknown
- 2010-12-13 EP EP10805799.3A patent/EP2513027B1/fr active Active
- 2010-12-13 SG SG2012043725A patent/SG181693A1/en unknown
- 2010-12-13 KR KR1020127018486A patent/KR101802543B1/ko not_active Expired - Fee Related
- 2010-12-14 TW TW99143718A patent/TWI468383B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6348638B1 (en) * | 1996-06-20 | 2002-02-19 | Basf Aktiengesellschaft | Method for removing by-products obtained when producing acrylic acid or methacrylic acids |
| FR2909999A1 (fr) * | 2006-12-19 | 2008-06-20 | Arkema France | Procede de preparation d'acide acrylique a partir de glycerol |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120105029A (ko) | 2012-09-24 |
| TW201136887A (en) | 2011-11-01 |
| FR2953830B1 (fr) | 2012-01-20 |
| KR101802543B1 (ko) | 2017-11-28 |
| CN102639478A (zh) | 2012-08-15 |
| BR112012014147A2 (pt) | 2017-01-24 |
| JP5784627B2 (ja) | 2015-09-24 |
| JP2013513593A (ja) | 2013-04-22 |
| FR2953830A1 (fr) | 2011-06-17 |
| EP2513027B1 (fr) | 2014-08-13 |
| EP2513027A1 (fr) | 2012-10-24 |
| IN2012DN04890A (enExample) | 2015-09-25 |
| SG181693A1 (en) | 2012-07-30 |
| MY157406A (en) | 2016-06-15 |
| CN102639478B (zh) | 2015-04-01 |
| WO2011080447A1 (fr) | 2011-07-07 |
| US8609904B2 (en) | 2013-12-17 |
| US20120302797A1 (en) | 2012-11-29 |
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