JP2016520096A5 - - Google Patents
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- Publication number
- JP2016520096A5 JP2016520096A5 JP2016514987A JP2016514987A JP2016520096A5 JP 2016520096 A5 JP2016520096 A5 JP 2016520096A5 JP 2016514987 A JP2016514987 A JP 2016514987A JP 2016514987 A JP2016514987 A JP 2016514987A JP 2016520096 A5 JP2016520096 A5 JP 2016520096A5
- Authority
- JP
- Japan
- Prior art keywords
- boiling solvent
- mixture
- crude product
- acrylic acid
- product mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 claims 18
- 238000009835 boiling Methods 0.000 claims 15
- 239000002904 solvent Substances 0.000 claims 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 6
- 239000012043 crude product Substances 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 claims 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 claims 1
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- -1 phenyl diamine Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361825205P | 2013-05-20 | 2013-05-20 | |
| US61/825,205 | 2013-05-20 | ||
| PCT/US2014/038573 WO2014189829A1 (en) | 2013-05-20 | 2014-05-19 | Method for the purification of acetic acid and acrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016520096A JP2016520096A (ja) | 2016-07-11 |
| JP2016520096A5 true JP2016520096A5 (enExample) | 2017-06-29 |
Family
ID=50942932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016514987A Ceased JP2016520096A (ja) | 2013-05-20 | 2014-05-19 | 酢酸及びアクリル酸の精製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9944582B2 (enExample) |
| EP (1) | EP2999686A1 (enExample) |
| JP (1) | JP2016520096A (enExample) |
| KR (1) | KR20160009598A (enExample) |
| CN (1) | CN105263895B (enExample) |
| AU (1) | AU2014268860B2 (enExample) |
| CA (1) | CA2908710A1 (enExample) |
| WO (1) | WO2014189829A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10239815B2 (en) | 2015-02-05 | 2019-03-26 | Nippon Shokubai Co., Ltd. | Method for producing acrylic acid |
| WO2017114831A1 (en) * | 2015-12-29 | 2017-07-06 | Shell Internationale Research Maatschappij B.V. | Process for converting alkanes and/or alkenes to alkenes and carboxylic acids |
| KR102079775B1 (ko) * | 2016-11-25 | 2020-02-20 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 및 장치 |
| FR3060000B1 (fr) * | 2016-12-08 | 2020-05-01 | Arkema France | Procede pour eviter le depot de polymeres dans un procede de purification d'acide (meth)acrylique. |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748159A (en) | 1952-09-08 | 1956-05-29 | Goodyear Tire & Rubber | Purification and decolorization of esters |
| GB783463A (en) | 1955-05-10 | 1957-09-25 | Distillers Co Yeast Ltd | Esters purification process |
| US2862958A (en) | 1955-10-13 | 1958-12-02 | Hercules Powder Co Ltd | Method of improving electrical properties of plasticizers by treatment with magnesium silicate |
| GB813867A (en) | 1956-12-27 | 1959-05-27 | Distillers Co Yeast Ltd | Purification of esters of dicarboxylic acids |
| DE1173473B (de) | 1962-06-29 | 1964-07-09 | Reichhold Chemie Ag | Verfahren zum Herstellen von aliphatischen oder aromatischen Carbonsaeureestern |
| DE1264762B (de) | 1963-09-03 | 1968-03-28 | Reichhold Chemie Ag | Weichmacher fuer organische Polymere |
| JPS5011364B1 (enExample) * | 1965-06-30 | 1975-04-30 | ||
| US3433831A (en) | 1965-06-30 | 1969-03-18 | Asahi Chemical Ind | Separation and purification of acrylic acid from acetic acid by solvent extraction and azeotropic distillation with a two component solvent-entrainer system |
| NL6715465A (enExample) * | 1966-11-14 | 1968-05-15 | ||
| US3422831A (en) * | 1967-02-20 | 1969-01-21 | Gen Electric | Turbine control system |
| US3666632A (en) * | 1968-10-08 | 1972-05-30 | Asahi Chemical Ind | Method for the separation of acrylic acid from aqueous solution containing acrylic acid and acetic acid |
| JPS4946942B1 (enExample) | 1971-04-05 | 1974-12-12 | ||
| JPS5522462B2 (enExample) | 1972-05-24 | 1980-06-17 | ||
| JPS4995918A (enExample) | 1973-01-24 | 1974-09-11 | ||
| JPS5011364A (enExample) | 1973-05-30 | 1975-02-05 | ||
| US5243069A (en) * | 1981-12-11 | 1993-09-07 | Rohm And Haas Company | Ester of Michael addition homopolymers of acrylic acid |
| JPS62267341A (ja) | 1986-05-16 | 1987-11-20 | Mitsubishi Kasei Vinyl Co | 可塑剤の製造法 |
| JPH0341051A (ja) | 1989-07-07 | 1991-02-21 | Idemitsu Petrochem Co Ltd | アクリル酸エステル又はメタクリル酸エステルの製造方法 |
| US5198580A (en) * | 1991-11-18 | 1993-03-30 | The Standard Oil Company | Process for oxidation of propane |
| TW295580B (enExample) | 1992-01-09 | 1997-01-11 | Nippon Catalytic Chem Ind | |
| JPH089567B2 (ja) | 1992-01-09 | 1996-01-31 | 株式会社日本触媒 | アクリル酸製造においてアクリル酸を高純度に精製する方法 |
| JP3832868B2 (ja) | 1994-07-27 | 2006-10-11 | 三菱化学株式会社 | アクリル酸の精製法 |
| JP3937462B2 (ja) | 1994-08-04 | 2007-06-27 | 三菱化学株式会社 | アクリル酸精製法 |
| JP3202150B2 (ja) * | 1995-08-04 | 2001-08-27 | 昭和電工株式会社 | 酢酸の精製方法 |
| JP3219682B2 (ja) * | 1995-09-29 | 2001-10-15 | 昭和電工株式会社 | 酢酸の精製方法、及び酢酸の製造方法 |
| JP3028925B2 (ja) | 1995-12-05 | 2000-04-04 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JPH09263566A (ja) | 1996-03-29 | 1997-10-07 | Cosmo Sogo Kenkyusho:Kk | 粗ベンゼンジカルボン酸の精製方法、精製に使用する触媒およびその製造方法 |
| FR2753445B1 (fr) * | 1996-09-16 | 1998-10-30 | Atochem Elf Sa | Procede perfectionne de purification de l'acide acrylique |
| JP3937495B2 (ja) | 1997-02-28 | 2007-06-27 | 株式会社日本触媒 | アクリル酸の回収方法 |
| US6084127A (en) | 1997-02-28 | 2000-07-04 | Nippon Shokubai Co Ltd | Method for recovering acrylic acid |
| JP3880128B2 (ja) | 1997-05-08 | 2007-02-14 | 株式会社日本触媒 | アクリル酸の回収方法 |
| US5880310A (en) | 1997-05-21 | 1999-03-09 | Mitsubishi Gas Chemical Company, Inc. | Process for producing plasticizer esters |
| US6114278A (en) | 1998-11-16 | 2000-09-05 | Saudi Basic Industries Corporation | Catalysts for catalytic oxidation of propane to acrylic acid, methods of making and using the same |
| DE60005870T2 (de) | 1999-03-05 | 2004-08-19 | Rohm And Haas Co. | Verfahren zur Herstellung von Acrylsäure |
| JP5073129B2 (ja) * | 1999-03-31 | 2012-11-14 | 株式会社日本触媒 | （メタ）アクリル酸の精製方法 |
| JP4809532B2 (ja) | 1999-11-15 | 2011-11-09 | サウディ ベーシック インダストリーズ コーポレイション | プロパンのアクリル酸への接触酸化用触媒、その製造法及び使用法 |
| CN1209332C (zh) * | 2000-06-14 | 2005-07-06 | 巴斯福股份公司 | 丙烯醛和/或丙烯酸的制备方法 |
| JP2005232008A (ja) | 2001-12-27 | 2005-09-02 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の蒸留方法 |
| WO2003064367A1 (en) * | 2002-01-29 | 2003-08-07 | Mitsubishi Chemical Corporation | Process for production of (meth)acrylic acid |
| GB0320206D0 (en) | 2003-08-29 | 2003-10-01 | Exxonmobil Chem Patents Inc | Improvements in or relating to plasticiser |
| FR2861724B1 (fr) | 2003-11-04 | 2005-12-30 | Arkema | Procede de purification de l'acide (meth)acrylique obtenu par oxydation d'un substrat gazeux |
| AU2004293259A1 (en) * | 2003-11-28 | 2005-06-09 | Mitsubishi Chemical Corporation | Method of purifying (meth)acrylic acid |
| JP2005179352A (ja) | 2003-11-28 | 2005-07-07 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の精製方法 |
| JP4333471B2 (ja) | 2004-05-11 | 2009-09-16 | 新日本理化株式会社 | ジカルボン酸ジエステルの製造方法 |
| JP4621174B2 (ja) | 2006-06-19 | 2011-01-26 | 株式会社日本触媒 | （メタ）アクリル酸および／またはそのエステルの蒸留方法 |
| CN1884249A (zh) | 2006-07-11 | 2006-12-27 | 天津天溶化工有限公司 | 邻苯二甲酸二辛酯清洁生产方法 |
| CN101269899B (zh) | 2008-05-13 | 2011-05-11 | 吉林大学 | 一种丙烯酸废水的综合处理方法 |
| CN101367720A (zh) | 2008-09-18 | 2009-02-18 | 中国石油大学(华东) | 一种隔壁共沸精馏塔提纯丙烯酸的工艺方法及装置 |
| CN101530780B (zh) | 2009-04-21 | 2011-08-24 | 浙江工商大学 | 一种两步分离提纯柱及其应用 |
| KR20160018515A (ko) | 2013-06-07 | 2016-02-17 | 사우디 베이식 인더스트리즈 코포레이션 | 다이옥틸 프탈레이트의 정제 방법 |
-
2014
- 2014-05-19 US US14/787,683 patent/US9944582B2/en not_active Expired - Fee Related
- 2014-05-19 WO PCT/US2014/038573 patent/WO2014189829A1/en not_active Ceased
- 2014-05-19 KR KR1020157034638A patent/KR20160009598A/ko not_active Withdrawn
- 2014-05-19 CA CA2908710A patent/CA2908710A1/en not_active Abandoned
- 2014-05-19 JP JP2016514987A patent/JP2016520096A/ja not_active Ceased
- 2014-05-19 AU AU2014268860A patent/AU2014268860B2/en not_active Ceased
- 2014-05-19 CN CN201480029153.7A patent/CN105263895B/zh not_active Expired - Fee Related
- 2014-05-19 EP EP14730395.2A patent/EP2999686A1/en not_active Ceased
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