TWI305772B - Method for recovering acrylic acid - Google Patents
Method for recovering acrylic acid Download PDFInfo
- Publication number
- TWI305772B TWI305772B TW094113069A TW94113069A TWI305772B TW I305772 B TWI305772 B TW I305772B TW 094113069 A TW094113069 A TW 094113069A TW 94113069 A TW94113069 A TW 94113069A TW I305772 B TWI305772 B TW I305772B
- Authority
- TW
- Taiwan
- Prior art keywords
- acrylic acid
- recovery unit
- dimer
- acid recovery
- mixture
- Prior art date
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 140
- 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 128
- 238000000034 method Methods 0.000 title claims description 37
- 238000011084 recovery Methods 0.000 claims description 66
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 43
- 239000012535 impurity Substances 0.000 claims description 32
- 238000000197 pyrolysis Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 238000009835 boiling Methods 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims 1
- 229960001058 bupropion Drugs 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 17
- 238000000926 separation method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000010025 steaming Methods 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 239000012530 fluid Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FZYDVDRIQZXXIW-UHFFFAOYSA-N propanoic acid;prop-2-enoic acid Chemical class CCC(O)=O.OC(=O)C=C FZYDVDRIQZXXIW-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
-
- 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
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)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020040029872A KR100714631B1 (ko) | 2004-04-29 | 2004-04-29 | 아크릴산의 회수 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200604162A TW200604162A (en) | 2006-02-01 |
| TWI305772B true TWI305772B (en) | 2009-02-01 |
Family
ID=35187992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094113069A TWI305772B (en) | 2004-04-29 | 2005-04-25 | Method for recovering acrylic acid |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7612231B2 (https=) |
| EP (1) | EP1740526B1 (https=) |
| JP (1) | JP4612041B2 (https=) |
| KR (1) | KR100714631B1 (https=) |
| CN (1) | CN1938256B (https=) |
| TW (1) | TWI305772B (https=) |
| WO (1) | WO2005105721A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100883365B1 (ko) * | 2007-10-12 | 2009-02-11 | 제일모직주식회사 | 폐아크릴계 수지의 재활용 방법 및 이를 이용한 아크릴계인조대리석용 조성물 |
| CN102078699B (zh) * | 2009-12-01 | 2013-06-05 | 宝舜科技股份有限公司 | 一种2-甲基萘的直接蒸馏工艺 |
| CN103159613B (zh) * | 2011-12-15 | 2015-09-23 | 上海华谊丙烯酸有限公司 | 回收设备和使用该设备的回收方法 |
| WO2014046261A1 (ja) * | 2012-09-24 | 2014-03-27 | 株式会社日本触媒 | ヒドロキシアルキルアクリレート、およびその製造方法 |
| KR101760044B1 (ko) | 2014-12-09 | 2017-07-20 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 |
| KR102079773B1 (ko) * | 2015-12-10 | 2020-02-20 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 |
| KR102079772B1 (ko) * | 2015-12-10 | 2020-02-20 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 |
| KR101990058B1 (ko) | 2015-12-22 | 2019-06-17 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 |
| US11214534B2 (en) | 2016-12-22 | 2022-01-04 | Eastman Chemical Company | Acrylic acid purification via dividing wall columns |
| CN110088075A (zh) | 2016-12-22 | 2019-08-02 | 伊士曼化工公司 | 经由共沸蒸馏分离丙酸与丙烯酸 |
| CN110684470B (zh) * | 2019-10-21 | 2022-03-01 | 江苏利田科技股份有限公司 | 一种利用uv单体废水制备丙烯酸酯粘合剂的方法以及一种丙烯酸酯粘合剂 |
| FR3110571B1 (fr) * | 2020-05-19 | 2022-04-15 | Arkema France | Procédé de valorisation de lourds d’acide acrylique et d’esters dudit acide par craquage thermique avec condensation partielle |
| WO2025131819A2 (en) | 2023-12-19 | 2025-06-26 | IFP Energies Nouvelles | Process for production of bio-acrylic acid |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4519281Y1 (https=) | 1965-05-22 | 1970-08-05 | ||
| US3761568A (en) * | 1971-02-16 | 1973-09-25 | Univ California | Method and apparatus for the destructive decomposition of organic wastes without air pollution and with recovery of chemical byproducts |
| JPS5191208A (en) | 1975-02-07 | 1976-08-10 | Akurirusanno jugoboshihoho | |
| JPS54100315A (en) | 1978-01-20 | 1979-08-08 | Nippon Shokubai Kagaku Kogyo Co Ltd | Recovery of acrylic acid |
| US4317926A (en) | 1978-01-19 | 1982-03-02 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for preparing and recovering acrylic acid |
| US4408125A (en) * | 1981-07-13 | 1983-10-04 | University Of Utah | Modular pyrolysis inlet and method for pyrolyzing compounds for analysis by mass spectrometer |
| CN1019011B (zh) * | 1989-04-15 | 1992-11-11 | 北京东方化工厂 | 从丙烯酸废油中回收丙烯酸的方法 |
| US5471937A (en) * | 1994-08-03 | 1995-12-05 | Mei Corporation | System and method for the treatment of hazardous waste material |
| FR2727964B1 (fr) | 1994-12-12 | 1997-01-24 | Atochem Elf Sa | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters |
| JP2907043B2 (ja) * | 1994-12-28 | 1999-06-21 | 東亞合成株式会社 | アクリル酸またはメタクリル酸エステルのミカエル付加物の分解方法 |
| DE19536191A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| US5837107A (en) * | 1995-12-20 | 1998-11-17 | Basf Aktiengesellschaft | Process for production of aqueous solutions of free hydroxylamine |
| JPH1112222A (ja) * | 1997-06-25 | 1999-01-19 | Nippon Shokubai Co Ltd | アクリル酸の回収方法 |
| US6324103B2 (en) * | 1998-11-11 | 2001-11-27 | Hitachi, Ltd. | Semiconductor integrated circuit device, memory module, storage device and the method for repairing semiconductor integrated circuit 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 |
| JP2003160532A (ja) * | 2001-11-28 | 2003-06-03 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の製造方法 |
| WO2003045892A1 (fr) | 2001-11-28 | 2003-06-05 | Mitsubishi Chemical Corporation | Procédé de production d'un composé d'acide (méth)acrylique |
| EP1452518B1 (en) * | 2001-12-04 | 2012-06-20 | Mitsubishi Chemical Corporation | Process for producing (meth)acrylic acid compounds |
| 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 |
-
2004
- 2004-04-29 KR KR1020040029872A patent/KR100714631B1/ko not_active Expired - Fee Related
-
2005
- 2005-04-25 TW TW094113069A patent/TWI305772B/zh not_active IP Right Cessation
- 2005-04-26 JP JP2007507250A patent/JP4612041B2/ja not_active Expired - Fee Related
- 2005-04-26 WO PCT/KR2005/001199 patent/WO2005105721A1/en not_active Ceased
- 2005-04-26 CN CN2005800107099A patent/CN1938256B/zh not_active Expired - Fee Related
- 2005-04-26 EP EP05740834.6A patent/EP1740526B1/en not_active Ceased
- 2005-04-28 US US11/116,367 patent/US7612231B2/en not_active Expired - Lifetime
-
2009
- 2009-09-23 US US12/565,359 patent/US8308913B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005105721A1 (en) | 2005-11-10 |
| CN1938256A (zh) | 2007-03-28 |
| US20100012476A1 (en) | 2010-01-21 |
| TW200604162A (en) | 2006-02-01 |
| CN1938256B (zh) | 2011-01-26 |
| EP1740526B1 (en) | 2016-06-01 |
| KR100714631B1 (ko) | 2007-05-07 |
| US7612231B2 (en) | 2009-11-03 |
| JP4612041B2 (ja) | 2011-01-12 |
| EP1740526A4 (en) | 2008-04-16 |
| JP2007532533A (ja) | 2007-11-15 |
| EP1740526A1 (en) | 2007-01-10 |
| US8308913B2 (en) | 2012-11-13 |
| US20050245763A1 (en) | 2005-11-03 |
| KR20050104544A (ko) | 2005-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |