BR112016009448B1 - Método para a produção de ácido acrílico - Google Patents
Método para a produção de ácido acrílico Download PDFInfo
- Publication number
- BR112016009448B1 BR112016009448B1 BR112016009448-4A BR112016009448A BR112016009448B1 BR 112016009448 B1 BR112016009448 B1 BR 112016009448B1 BR 112016009448 A BR112016009448 A BR 112016009448A BR 112016009448 B1 BR112016009448 B1 BR 112016009448B1
- Authority
- BR
- Brazil
- Prior art keywords
- steam ejector
- steam
- acrylic acid
- ejector
- gas
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 18
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 7
- 239000001294 propane Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 238000006116 polymerization reaction Methods 0.000 abstract description 27
- -1 acrylic ester Chemical class 0.000 abstract description 11
- 230000006837 decompression Effects 0.000 abstract description 10
- 239000007789 gas Substances 0.000 description 43
- 238000004821 distillation Methods 0.000 description 36
- 239000003112 inhibitor Substances 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000005395 methacrylic acid group Chemical class 0.000 description 7
- 150000001253 acrylic acids Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000003440 styrenes Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical group COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-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
- 238000009825 accumulation Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HBWOFFDJTMUANX-UHFFFAOYSA-N copper;dibutylcarbamodithioic acid Chemical compound [Cu].CCCCN(C(S)=S)CCCC HBWOFFDJTMUANX-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 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
- 150000002989 phenols Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000004804 winding Methods 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
- C07C51/42—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
- C07C51/445—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by steam distillation
-
- 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
- B01D3/10—Vacuum distillation
-
- 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
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/38—Steam distillation
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F04—POSITIVE - DISPLACEMENT MACHINES FOR LIQUIDS; PUMPS FOR LIQUIDS OR ELASTIC FLUIDS
- F04F—PUMPING OF FLUID BY DIRECT CONTACT OF ANOTHER FLUID OR BY USING INERTIA OF FLUID TO BE PUMPED; SIPHONS
- F04F5/00—Jet pumps, i.e. devices in which flow is induced by pressure drop caused by velocity of another fluid flow
- F04F5/14—Jet pumps, i.e. devices in which flow is induced by pressure drop caused by velocity of another fluid flow the inducing fluid being elastic fluid
- F04F5/16—Jet pumps, i.e. devices in which flow is induced by pressure drop caused by velocity of another fluid flow the inducing fluid being elastic fluid displacing elastic fluids
- F04F5/20—Jet pumps, i.e. devices in which flow is induced by pressure drop caused by velocity of another fluid flow the inducing fluid being elastic fluid displacing elastic fluids for evacuating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013-224082 | 2013-10-29 | ||
| JP2013224082 | 2013-10-29 | ||
| PCT/JP2014/078603 WO2015064563A1 (ja) | 2013-10-29 | 2014-10-28 | 易重合性化合物の減圧蒸留の方法およびアクリル酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112016009448A2 BR112016009448A2 (pt) | 2017-08-01 |
| BR112016009448B1 true BR112016009448B1 (pt) | 2021-07-13 |
Family
ID=53004165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112016009448-4A BR112016009448B1 (pt) | 2013-10-29 | 2014-10-28 | Método para a produção de ácido acrílico |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9738586B2 (enExample) |
| EP (1) | EP3064485B2 (enExample) |
| JP (3) | JP2015110551A (enExample) |
| CN (1) | CN105683145B (enExample) |
| BR (1) | BR112016009448B1 (enExample) |
| WO (1) | WO2015064563A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202015106097U1 (de) * | 2015-11-11 | 2016-02-01 | Holger Blum | Fördereinrichtung für eine Vakuumdestillationsanlage |
| JP7147567B2 (ja) * | 2018-01-19 | 2022-10-05 | 三菱ケミカル株式会社 | (メタ)アクリル酸又はそのエステルの製造方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4833057Y1 (enExample) * | 1970-07-01 | 1973-10-08 | ||
| US3702346A (en) * | 1971-06-30 | 1972-11-07 | Universal Oil Prod Co | Conversion of ethylbenzene to styrene |
| JPH01105000A (ja) * | 1987-10-15 | 1989-04-21 | Hitachi Ltd | 真空エゼクタ装置 |
| JPH10204030A (ja) * | 1997-01-24 | 1998-08-04 | Toagosei Co Ltd | (メタ)アクリル酸エステルの精製方法及び製造方法並びにその製造装置 |
| JP2000256221A (ja) * | 1999-03-04 | 2000-09-19 | Mitsubishi Chemicals Corp | 易重合性化合物の精製方法 |
| JP4698778B2 (ja) | 1999-06-03 | 2011-06-08 | 株式会社日本触媒 | (メタ)アクリル酸(エステル)の精製方法 |
| JP2000344688A (ja) * | 1999-06-04 | 2000-12-12 | Mitsubishi Chemicals Corp | 易重合性化合物の精製方法 |
| JP3948855B2 (ja) | 1999-06-10 | 2007-07-25 | 株式会社日本触媒 | (メタ)アクリル酸の製造方法 |
| JP2001131116A (ja) * | 1999-11-08 | 2001-05-15 | Nippon Shokubai Co Ltd | 易重合性物質含有液の蒸留方法 |
| US6739288B1 (en) * | 2000-01-14 | 2004-05-25 | Tvl Co., Ltd. | Steam heating device |
| JP2001213839A (ja) | 2000-02-03 | 2001-08-07 | Nippon Shokubai Co Ltd | (メタ)アクリル酸の製造方法 |
| JP3875471B2 (ja) * | 2000-08-28 | 2007-01-31 | 株式会社日立製作所 | 復水器真空ポンプシステム |
| WO2003018162A1 (en) * | 2001-08-22 | 2003-03-06 | Mitsubishi Chemical Corporation | Distilling equipment for lase-of-polymerization compound |
| JP4074455B2 (ja) * | 2001-11-27 | 2008-04-09 | 三菱化学株式会社 | (メタ)アクリル酸の製造方法 |
| JP2003073327A (ja) * | 2001-09-03 | 2003-03-12 | Nippon Shokubai Co Ltd | 有機酸の製造方法 |
| JP2003103105A (ja) * | 2001-09-28 | 2003-04-08 | Sumitomo Chem Co Ltd | 易重合性物質の蒸留方法およびこれに使用する蒸留装置 |
| JP4783530B2 (ja) * | 2001-09-28 | 2011-09-28 | 住友化学株式会社 | 易重合性物質の蒸留方法およびこれに使用する蒸留装置 |
| JP4095471B2 (ja) | 2003-02-28 | 2008-06-04 | 株式会社日本触媒 | 易重合性物質の蒸留方法 |
| JP2004269417A (ja) * | 2003-03-07 | 2004-09-30 | Mitsubishi Rayon Co Ltd | (メタ)アクリル酸エステルの製造方法 |
| JP4715106B2 (ja) * | 2004-04-01 | 2011-07-06 | 三菱化学株式会社 | (メタ)アクリル酸誘導体の製造方法 |
| JP2007162975A (ja) * | 2005-12-09 | 2007-06-28 | Miura Co Ltd | 食品機械 |
| JP5368673B2 (ja) * | 2006-01-20 | 2013-12-18 | 株式会社日本触媒 | (メタ)アクリル酸の製造方法 |
| KR100999428B1 (ko) | 2006-01-20 | 2010-12-09 | 니폰 쇼쿠바이 컴파니 리미티드 | (메타)아크릴산의 제조 방법 |
| JP4822893B2 (ja) * | 2006-03-24 | 2011-11-24 | 中国電力株式会社 | 真空ポンプ装置用ヒータの配線構造 |
| JP5097533B2 (ja) | 2007-12-21 | 2012-12-12 | 三菱レイヨン株式会社 | 易重合性物質取扱装置 |
| JP2009249314A (ja) | 2008-04-03 | 2009-10-29 | Mitsubishi Rayon Co Ltd | (メタ)アクリル酸ヒドロキシアルキルエステルの製造装置 |
| US8932434B2 (en) * | 2009-03-19 | 2015-01-13 | Lg Chem, Ltd. | Dividing wall distillation column for producing high purity acrylic acid and fractional distillation method using the same |
| JP5513279B2 (ja) * | 2010-06-24 | 2014-06-04 | 日本エゼクターエンジニアリング株式会社 | 製鋼用二次精錬における真空脱ガス用の不純物および排ガス処理装置 |
-
2014
- 2014-10-28 BR BR112016009448-4A patent/BR112016009448B1/pt active IP Right Grant
- 2014-10-28 CN CN201480059285.4A patent/CN105683145B/zh active Active
- 2014-10-28 JP JP2014219226A patent/JP2015110551A/ja active Pending
- 2014-10-28 WO PCT/JP2014/078603 patent/WO2015064563A1/ja not_active Ceased
- 2014-10-28 EP EP14857447.8A patent/EP3064485B2/en active Active
-
2016
- 2016-04-21 US US15/134,980 patent/US9738586B2/en active Active
-
2018
- 2018-10-22 JP JP2018198260A patent/JP6777131B2/ja active Active
-
2020
- 2020-10-05 JP JP2020168277A patent/JP2020203957A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015064563A1 (ja) | 2015-05-07 |
| EP3064485A1 (en) | 2016-09-07 |
| BR112016009448A2 (pt) | 2017-08-01 |
| JP2020203957A (ja) | 2020-12-24 |
| EP3064485B2 (en) | 2021-02-24 |
| JP6777131B2 (ja) | 2020-10-28 |
| EP3064485A4 (en) | 2016-11-09 |
| JP2019014750A (ja) | 2019-01-31 |
| CN105683145B (zh) | 2017-11-14 |
| US20160237017A1 (en) | 2016-08-18 |
| CN105683145A (zh) | 2016-06-15 |
| EP3064485B1 (en) | 2017-11-29 |
| JP2015110551A (ja) | 2015-06-18 |
| US9738586B2 (en) | 2017-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B25A | Requested transfer of rights approved |
Owner name: MITSUBISHI RAYON CO. LTD. (JP) |
|
| B25D | Requested change of name of applicant approved |
Owner name: MITSUBISHI CHEMICAL CORPORATION (JP) |
|
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 28/10/2014, OBSERVADAS AS CONDICOES LEGAIS. |