BR112018004525B1 - Processo aperfeiçoado de recuperação e produção de ácido (met)acrílico de grau polímero - Google Patents
Processo aperfeiçoado de recuperação e produção de ácido (met)acrílico de grau polímero Download PDFInfo
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- BR112018004525B1 BR112018004525B1 BR112018004525-0A BR112018004525A BR112018004525B1 BR 112018004525 B1 BR112018004525 B1 BR 112018004525B1 BR 112018004525 A BR112018004525 A BR 112018004525A BR 112018004525 B1 BR112018004525 B1 BR 112018004525B1
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- acrylic acid
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 62
- 230000008569 process Effects 0.000 title claims abstract description 59
- 229920000642 polymer Polymers 0.000 title claims abstract description 48
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 129
- 238000011282 treatment Methods 0.000 claims abstract description 85
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 63
- 239000000126 substance Substances 0.000 claims abstract description 61
- 230000018044 dehydration Effects 0.000 claims abstract description 59
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 59
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 239000002243 precursor Substances 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 15
- 230000003647 oxidation Effects 0.000 claims abstract description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 109
- 238000004821 distillation Methods 0.000 claims description 45
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000007789 gas Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000013043 chemical agent Substances 0.000 claims description 22
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- RNYZJZKPGHQTJR-UHFFFAOYSA-N protoanemonin Chemical compound C=C1OC(=O)C=C1 RNYZJZKPGHQTJR-UHFFFAOYSA-N 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims description 4
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims description 4
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical group CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
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- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000012495 reaction gas Substances 0.000 claims description 3
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 claims description 2
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 2
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
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- 230000002000 scavenging effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Classifications
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1559493 | 2015-10-06 | ||
| FR1559493A FR3041958B1 (fr) | 2015-10-06 | 2015-10-06 | Procede ameliore de production d’acide (meth)acrylique de grade polymere |
| PCT/FR2016/052434 WO2017060583A1 (fr) | 2015-10-06 | 2016-09-26 | Procédé amélioré de production d'acide (meth)acrylique de grade polymère |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112018004525A2 BR112018004525A2 (enExample) | 2018-03-07 |
| BR112018004525B1 true BR112018004525B1 (pt) | 2022-01-25 |
Family
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|---|---|---|---|
| BR112018004525-0A BR112018004525B1 (pt) | 2015-10-06 | 2016-09-26 | Processo aperfeiçoado de recuperação e produção de ácido (met)acrílico de grau polímero |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10961179B2 (enExample) |
| EP (1) | EP3359520B1 (enExample) |
| JP (1) | JP6895954B2 (enExample) |
| KR (1) | KR102698594B1 (enExample) |
| CN (1) | CN108137469B (enExample) |
| BR (1) | BR112018004525B1 (enExample) |
| FR (1) | FR3041958B1 (enExample) |
| TW (1) | TW201730143A (enExample) |
| WO (1) | WO2017060583A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018118702A1 (en) * | 2016-12-22 | 2018-06-28 | Eastman Chemical Company | Acrylic acid purification via dividing wall columns |
| FR3064630B1 (fr) | 2017-04-04 | 2019-09-13 | Arkema France | Procede de purification d'acide (meth)acrylique incluant une colonne de distillation a paroi separatrice |
| FR3094716B1 (fr) * | 2019-04-02 | 2021-06-04 | Arkema France | Production d’acide acrylique de grade polymere |
| FR3108906B1 (fr) | 2020-04-06 | 2022-03-04 | Arkema France | Procede de purification d’acide (meth)acrylique |
| KR102855131B1 (ko) * | 2021-10-15 | 2025-09-03 | 주식회사 엘지화학 | 아크릴산 제조방법 |
| KR102855127B1 (ko) * | 2021-10-15 | 2025-09-03 | 주식회사 엘지화학 | 아크릴산 제조방법 |
| WO2023063549A1 (ko) * | 2021-10-15 | 2023-04-20 | 주식회사 엘지화학 | 아크릴산 제조방법 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725208A (en) | 1971-08-20 | 1973-04-03 | Nippon Kayaku Kk | Process for purification of acrylic acid from aldehydes by distillation with a reagent |
| DE3641996A1 (de) | 1986-12-09 | 1988-06-16 | Basf Ag | Verfahren zum abtrennen von aldehyden aus (alpha),(beta)-olefinisch ungesaettigten carbonsaeuren |
| TW305830B (enExample) | 1993-03-26 | 1997-05-21 | Sulzer Chemtech Ag | |
| US5571386A (en) | 1994-05-31 | 1996-11-05 | Rohm And Haas Company | Process for grade acrylic acid |
| US5759358A (en) * | 1994-05-31 | 1998-06-02 | Rohm And Haas Company | Process for pure grade acrylic acid |
| DE19606877A1 (de) | 1996-02-23 | 1997-08-28 | Basf Ag | Verfahren zur Reinigung von Acrylsäure und Methacrylsäure |
| JP2001058907A (ja) * | 1997-02-17 | 2001-03-06 | Sumitomo Chem Co Ltd | 除草剤組成物 |
| DE19740252A1 (de) | 1997-09-12 | 1999-03-18 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Methacrylsäure |
| TW524796B (en) * | 1997-11-17 | 2003-03-21 | Sumitomo Chemical Co | Method for producing acrylic acid |
| JP4542214B2 (ja) * | 1999-08-20 | 2010-09-08 | 株式会社日本触媒 | アクリル酸の精製方法 |
| JP4361995B2 (ja) | 1999-12-22 | 2009-11-11 | 株式会社日本触媒 | アクリル酸の精製方法 |
| JP3938646B2 (ja) | 2000-01-14 | 2007-06-27 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP2001213839A (ja) * | 2000-02-03 | 2001-08-07 | Nippon Shokubai Co Ltd | （メタ）アクリル酸の製造方法 |
| DE10055221A1 (de) | 2000-11-08 | 2002-05-29 | Bayer Ag | Verfahren zur Herstellung von 4-Aminodiphenylamin |
| JP4765165B2 (ja) * | 2000-12-13 | 2011-09-07 | 東亞合成株式会社 | 高純度アクリル酸の製造方法 |
| JP4759153B2 (ja) * | 2001-03-21 | 2011-08-31 | 株式会社日本触媒 | （メタ）アクリル酸溶液の蒸留方法 |
| JP4440518B2 (ja) * | 2002-07-16 | 2010-03-24 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP4032033B2 (ja) * | 2003-06-30 | 2008-01-16 | ローム アンド ハース カンパニー | 高純度メタクリル酸の製造法 |
| JP2005179352A (ja) * | 2003-11-28 | 2005-07-07 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の精製方法 |
| ZA200603915B (en) * | 2003-11-28 | 2007-09-26 | Mitsubishi Chem Corp | Method of purifying (meth) acrylic acid |
| JP5199260B2 (ja) * | 2006-09-15 | 2013-05-15 | アルケマ インコーポレイティド | アクリル酸の生成方法 |
| KR101165371B1 (ko) * | 2009-03-19 | 2012-07-12 | 주식회사 엘지화학 | 고순도 아크릴산 생산을 위한 분리벽형 증류탑 및 이를 이용한 분별증류방법 |
| FR2957594B1 (fr) * | 2010-03-18 | 2013-04-26 | Arkema France | Procede de fabrication d'acide acrylique bio-ressource de grade polymere a partir de glycerol |
| JP6097181B2 (ja) * | 2012-09-06 | 2017-03-15 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| CN106061934B (zh) * | 2014-02-20 | 2019-05-03 | 阿科玛股份有限公司 | 用于生产丙烯酸的方法和系统 |
-
2015
- 2015-10-06 FR FR1559493A patent/FR3041958B1/fr active Active
-
2016
- 2016-09-26 EP EP16788151.5A patent/EP3359520B1/fr active Active
- 2016-09-26 US US15/765,496 patent/US10961179B2/en active Active
- 2016-09-26 KR KR1020187011761A patent/KR102698594B1/ko active Active
- 2016-09-26 BR BR112018004525-0A patent/BR112018004525B1/pt active IP Right Grant
- 2016-09-26 TW TW105131068A patent/TW201730143A/zh unknown
- 2016-09-26 JP JP2018517502A patent/JP6895954B2/ja active Active
- 2016-09-26 CN CN201680058532.8A patent/CN108137469B/zh active Active
- 2016-09-26 WO PCT/FR2016/052434 patent/WO2017060583A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018531252A (ja) | 2018-10-25 |
| CN108137469A (zh) | 2018-06-08 |
| KR102698594B1 (ko) | 2024-08-23 |
| FR3041958A1 (fr) | 2017-04-07 |
| BR112018004525A2 (enExample) | 2018-03-07 |
| US10961179B2 (en) | 2021-03-30 |
| JP6895954B2 (ja) | 2021-06-30 |
| KR20180064432A (ko) | 2018-06-14 |
| TW201730143A (zh) | 2017-09-01 |
| FR3041958B1 (fr) | 2019-06-14 |
| WO2017060583A1 (fr) | 2017-04-13 |
| US20190071382A1 (en) | 2019-03-07 |
| EP3359520B1 (fr) | 2024-07-10 |
| CN108137469B (zh) | 2021-08-03 |
| EP3359520A1 (fr) | 2018-08-15 |
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Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 26/09/2016, OBSERVADAS AS CONDICOES LEGAIS. |