CA3008401A1 - Process for purification of methyl methacrylate - Google Patents
Process for purification of methyl methacrylate Download PDFInfo
- Publication number
- CA3008401A1 CA3008401A1 CA3008401A CA3008401A CA3008401A1 CA 3008401 A1 CA3008401 A1 CA 3008401A1 CA 3008401 A CA3008401 A CA 3008401A CA 3008401 A CA3008401 A CA 3008401A CA 3008401 A1 CA3008401 A1 CA 3008401A1
- Authority
- CA
- Canada
- Prior art keywords
- distillation column
- stream
- water
- bottoms stream
- mma
- 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.)
- Pending
Links
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000000746 purification Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000004821 distillation Methods 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000012074 organic phase Substances 0.000 claims abstract description 22
- 239000008346 aqueous phase Substances 0.000 claims abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 15
- -1 alkali metal salts Chemical class 0.000 claims description 11
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 10
- 238000010980 drying distillation Methods 0.000 claims description 9
- 238000006709 oxidative esterification reaction Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 238000001035 drying Methods 0.000 abstract description 5
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 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
- 241000183024 Populus tremula Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KNXDBHJMMVAXJS-UHFFFAOYSA-N hexane;2-methylprop-2-enoic acid Chemical compound CCCCCC.CC(=C)C(O)=O KNXDBHJMMVAXJS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UOWWZCANEJESES-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;sodium Chemical compound [Na].COC(=O)C(C)=C UOWWZCANEJESES-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by 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
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/04—Methanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- 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)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562269461P | 2015-12-18 | 2015-12-18 | |
| US62/269,461 | 2015-12-18 | ||
| PCT/US2016/065490 WO2017105977A1 (en) | 2015-12-18 | 2016-12-08 | Process for purification of methyl methacrylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3008401A1 true CA3008401A1 (en) | 2017-06-22 |
Family
ID=57681749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3008401A Pending CA3008401A1 (en) | 2015-12-18 | 2016-12-08 | Process for purification of methyl methacrylate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10487038B2 (enExample) |
| EP (1) | EP3390342B1 (enExample) |
| JP (1) | JP6913091B2 (enExample) |
| KR (1) | KR102638548B1 (enExample) |
| CN (1) | CN108368025B (enExample) |
| BR (1) | BR112018011104B1 (enExample) |
| CA (1) | CA3008401A1 (enExample) |
| MX (1) | MX2018007379A (enExample) |
| SA (1) | SA518391736B1 (enExample) |
| SG (1) | SG11201804741TA (enExample) |
| TW (1) | TW201739730A (enExample) |
| WO (1) | WO2017105977A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201722903A (zh) * | 2015-12-18 | 2017-07-01 | 陶氏全球科技責任有限公司 | 用於純化甲基丙烯酸甲酯之方法 |
| CN112955427B (zh) * | 2019-04-04 | 2024-04-19 | 株式会社Lg化学 | 用于连续纯化酯化反应产物的系统 |
| WO2020261720A1 (ja) * | 2019-06-28 | 2020-12-30 | 旭化成株式会社 | メタクリル酸メチルの製造方法 |
| CN114539060B (zh) * | 2022-04-27 | 2022-07-05 | 太原理工大学 | 一种无排放甲醇脱氢制甲酸甲酯的方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1490688A (fr) * | 1966-06-22 | 1967-08-04 | Melle Usines Sa | Procédé pour séparer les constituants de mélanges azéotropiques de méthanol et d'ester aliphatique inférieur |
| EP0044409B1 (en) * | 1980-06-20 | 1984-01-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for purifying methyl methacrylate |
| JPS579740A (en) * | 1980-06-20 | 1982-01-19 | Asahi Chem Ind Co Ltd | Purification of methyl methacrylate |
| JPS579739A (en) * | 1980-06-20 | 1982-01-19 | Asahi Chem Ind Co Ltd | Purification of methyl methacrylate |
| JPS5877845A (ja) * | 1981-11-02 | 1983-05-11 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
| JP2582127B2 (ja) * | 1988-07-04 | 1997-02-19 | 株式会社クラレ | メタクリル酸メチルの精製法 |
| JP2859682B2 (ja) * | 1989-03-31 | 1999-02-17 | 三井化学株式会社 | メタクリル酸メチルの精製方法及び製造方法 |
| CA2012935A1 (en) * | 1989-03-31 | 1990-09-30 | Hirozo Segawa | Purification and preparation processes for methyl methacrylate |
| US5435892A (en) | 1993-08-30 | 1995-07-25 | Mitsubishi Rayon Co., Ltd. | Process for separating methanol and methyl acrylate or methyl methacrylate |
| JP3585989B2 (ja) * | 1995-03-29 | 2004-11-10 | 大阪有機化学工業株式会社 | アクリル酸メチルまたはメタクリル酸メチルとメタノールの分離方法 |
| JP3999926B2 (ja) * | 2000-05-12 | 2007-10-31 | 三菱レイヨン株式会社 | メタクリル酸エステルの精製方法 |
| JP3672818B2 (ja) * | 2000-12-26 | 2005-07-20 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの精製方法 |
| JP4733275B2 (ja) * | 2001-01-10 | 2011-07-27 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの精製方法 |
| JP4942878B2 (ja) * | 2001-02-07 | 2012-05-30 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの精製方法 |
| JP3819419B2 (ja) | 2006-04-21 | 2006-09-06 | 旭化成ケミカルズ株式会社 | メタクロレイン及びメタノールの回収方法 |
| CN103833551A (zh) * | 2012-11-27 | 2014-06-04 | 华东理工大学工程设计研究院有限公司 | 一种甲基丙烯酸甲酯的分离设备及分离方法 |
| JP6036402B2 (ja) * | 2013-02-26 | 2016-11-30 | 三菱化学株式会社 | （メタ）アクリル酸エステルの製造方法 |
| JP6094258B2 (ja) * | 2013-02-26 | 2017-03-15 | 三菱化学株式会社 | （メタ）アクリル酸エステルの製造方法 |
| JP6036400B2 (ja) * | 2013-02-26 | 2016-11-30 | 三菱化学株式会社 | （メタ）アクリル酸エステルの製造方法 |
| JP2014162763A (ja) * | 2013-02-26 | 2014-09-08 | Mitsubishi Chemicals Corp | （メタ）アクリル酸エステルの製造方法 |
| JP6036401B2 (ja) * | 2013-02-26 | 2016-11-30 | 三菱化学株式会社 | （メタ）アクリル酸エステルの製造方法 |
| TWI715627B (zh) * | 2015-09-16 | 2021-01-11 | 德商羅伊姆公司 | 含鈉鹽之mma-甲醇混合物的萃取後處理 |
-
2016
- 2016-11-22 TW TW105138316A patent/TW201739730A/zh unknown
- 2016-12-08 SG SG11201804741TA patent/SG11201804741TA/en unknown
- 2016-12-08 CN CN201680070894.9A patent/CN108368025B/zh active Active
- 2016-12-08 MX MX2018007379A patent/MX2018007379A/es unknown
- 2016-12-08 JP JP2018528038A patent/JP6913091B2/ja active Active
- 2016-12-08 KR KR1020187018564A patent/KR102638548B1/ko active Active
- 2016-12-08 EP EP16820070.7A patent/EP3390342B1/en active Active
- 2016-12-08 BR BR112018011104-0A patent/BR112018011104B1/pt active IP Right Grant
- 2016-12-08 WO PCT/US2016/065490 patent/WO2017105977A1/en not_active Ceased
- 2016-12-08 US US15/776,850 patent/US10487038B2/en active Active
- 2016-12-08 CA CA3008401A patent/CA3008401A1/en active Pending
-
2018
- 2018-06-05 SA SA518391736A patent/SA518391736B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112018011104A2 (pt) | 2018-12-04 |
| US20180346403A1 (en) | 2018-12-06 |
| EP3390342B1 (en) | 2020-03-11 |
| TW201739730A (zh) | 2017-11-16 |
| US10487038B2 (en) | 2019-11-26 |
| CN108368025A (zh) | 2018-08-03 |
| BR112018011104B1 (pt) | 2021-03-23 |
| WO2017105977A1 (en) | 2017-06-22 |
| EP3390342A1 (en) | 2018-10-24 |
| JP6913091B2 (ja) | 2021-08-04 |
| KR102638548B1 (ko) | 2024-02-20 |
| SA518391736B1 (ar) | 2021-12-06 |
| CN108368025B (zh) | 2021-06-01 |
| JP2018537466A (ja) | 2018-12-20 |
| KR20180094937A (ko) | 2018-08-24 |
| SG11201804741TA (en) | 2018-07-30 |
| MX2018007379A (es) | 2018-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |
|
| EEER | Examination request |
Effective date: 20211203 |