CA2965482C - A process to separate methanol from mma - Google Patents
A process to separate methanol from mma Download PDFInfo
- Publication number
- CA2965482C CA2965482C CA2965482A CA2965482A CA2965482C CA 2965482 C CA2965482 C CA 2965482C CA 2965482 A CA2965482 A CA 2965482A CA 2965482 A CA2965482 A CA 2965482A CA 2965482 C CA2965482 C CA 2965482C
- Authority
- CA
- Canada
- Prior art keywords
- column
- mma
- stream
- methanol
- distillation
- 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.)
- Active
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 238000000034 method Methods 0.000 title claims description 44
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000000895 extractive distillation Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000183024 Populus tremula Species 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006709 oxidative esterification reaction Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- -1 e.g. Natural products 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003339 best practice Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 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 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010998 test method Methods 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
-
- 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
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462073406P | 2014-10-31 | 2014-10-31 | |
| US62/073,406 | 2014-10-31 | ||
| PCT/US2015/054479 WO2016069227A1 (en) | 2014-10-31 | 2015-10-07 | Separation process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2965482A1 CA2965482A1 (en) | 2016-05-06 |
| CA2965482C true CA2965482C (en) | 2023-03-28 |
Family
ID=54337912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2965482A Active CA2965482C (en) | 2014-10-31 | 2015-10-07 | A process to separate methanol from mma |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10059651B2 (enExample) |
| EP (1) | EP3212598B1 (enExample) |
| JP (1) | JP6659680B2 (enExample) |
| KR (1) | KR102583533B1 (enExample) |
| CN (1) | CN107074729B (enExample) |
| BR (1) | BR112017007961B1 (enExample) |
| CA (1) | CA2965482C (enExample) |
| MX (1) | MX2017005023A (enExample) |
| SA (1) | SA517381346B1 (enExample) |
| SG (1) | SG11201703297QA (enExample) |
| TW (1) | TW201615600A (enExample) |
| WO (1) | WO2016069227A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106966903B (zh) * | 2017-04-12 | 2021-05-14 | 中国矿业大学(北京) | 一种甲基丙烯酸甲酯、甲苯混合物的分离方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4837012B1 (enExample) * | 1970-12-28 | 1973-11-08 | ||
| DE2706684A1 (de) * | 1977-02-17 | 1978-08-24 | Basf Ag | Verfahren zur reindarstellung von dimethylcarbonat |
| JPS5424812A (en) * | 1977-07-22 | 1979-02-24 | Mitsubishi Chem Ind Ltd | Separation of methyl methacrylate |
| GB2008430B (en) | 1977-11-17 | 1982-04-28 | Asahi Chemical Ind | Process for producing carboxylic esters |
| DE3018071C2 (de) | 1979-05-17 | 1985-06-05 | Asahi Kasei Kogyo K.K., Osaka | Verfahren zur Herstellung von Carbonsäureestern |
| EP0044409B1 (en) * | 1980-06-20 | 1984-01-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for purifying methyl methacrylate |
| DE3211901A1 (de) * | 1982-03-31 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur abtrennung von methanol aus wasser enthaltenden mischungen von methylmethacrylat und methanol |
| 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 |
| CA2012935A1 (en) | 1989-03-31 | 1990-09-30 | Hirozo Segawa | Purification and preparation processes for methyl methacrylate |
| KR930006144B1 (ko) * | 1990-07-12 | 1993-07-07 | 삼성전자 주식회사 | 반도체 장치 및 방법 |
| US5435892A (en) | 1993-08-30 | 1995-07-25 | Mitsubishi Rayon Co., Ltd. | Process for separating methanol and methyl acrylate or methyl methacrylate |
| JPH0853393A (ja) * | 1994-06-06 | 1996-02-27 | Mitsui Toatsu Chem Inc | メタクリル酸メチルの連続製造方法 |
| ATE280750T1 (de) | 1995-07-18 | 2004-11-15 | Asahi Kasei Chemicals Corp | Verfahren zur herstellung von carbonsäureestern |
| JPH09216850A (ja) | 1996-02-09 | 1997-08-19 | Mitsubishi Rayon Co Ltd | カルボン酸エステルの製造方法 |
| TW385304B (en) | 1996-09-10 | 2000-03-21 | Asahi Chemical Ind | Process for producing methacrylic acid ester or acrylic acid ester |
| SG71815A1 (en) | 1997-07-08 | 2000-04-18 | Asahi Chemical Ind | Method of producing methyl methacrylate |
| US6680405B1 (en) | 1998-02-09 | 2004-01-20 | Mitsubishi Rayon Co., Ltd. | Process for the preparation of methyl methacrylate |
| JP2003252825A (ja) * | 2001-12-25 | 2003-09-10 | Mitsubishi Chemicals Corp | （メタ）アクリル酸類製造時の副生物の分解方法 |
| JP2007045803A (ja) * | 2005-08-12 | 2007-02-22 | Asahi Kasei Chemicals Corp | 精製されたメタクリル酸メチルを得る方法 |
| 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 |
| JP5801296B2 (ja) | 2010-05-24 | 2015-10-28 | 株式会社日本触媒 | α位置換アクリル酸エステル類及びそれを含む組成物、並びに、それらの製造方法 |
| 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 |
| CN103304371A (zh) * | 2013-07-01 | 2013-09-18 | 济南大学 | 甲醇－丙烯酸甲酯共沸混合物的间歇萃取精馏分离方法 |
-
2015
- 2015-10-07 WO PCT/US2015/054479 patent/WO2016069227A1/en not_active Ceased
- 2015-10-07 MX MX2017005023A patent/MX2017005023A/es unknown
- 2015-10-07 KR KR1020177012820A patent/KR102583533B1/ko active Active
- 2015-10-07 CA CA2965482A patent/CA2965482C/en active Active
- 2015-10-07 SG SG11201703297QA patent/SG11201703297QA/en unknown
- 2015-10-07 US US15/522,054 patent/US10059651B2/en active Active
- 2015-10-07 CN CN201580056032.6A patent/CN107074729B/zh active Active
- 2015-10-07 BR BR112017007961-5A patent/BR112017007961B1/pt active IP Right Grant
- 2015-10-07 JP JP2017521118A patent/JP6659680B2/ja active Active
- 2015-10-07 EP EP15784233.7A patent/EP3212598B1/en active Active
- 2015-10-27 TW TW104135276A patent/TW201615600A/zh unknown
-
2017
- 2017-04-17 SA SA517381346A patent/SA517381346B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SA517381346B1 (ar) | 2020-12-14 |
| KR102583533B1 (ko) | 2023-09-27 |
| WO2016069227A1 (en) | 2016-05-06 |
| CN107074729B (zh) | 2020-08-04 |
| US10059651B2 (en) | 2018-08-28 |
| EP3212598A1 (en) | 2017-09-06 |
| MX2017005023A (es) | 2017-07-19 |
| US20170334829A1 (en) | 2017-11-23 |
| JP2017533198A (ja) | 2017-11-09 |
| TW201615600A (zh) | 2016-05-01 |
| EP3212598B1 (en) | 2018-09-12 |
| JP6659680B2 (ja) | 2020-03-04 |
| SG11201703297QA (en) | 2017-05-30 |
| KR20170076709A (ko) | 2017-07-04 |
| BR112017007961A2 (pt) | 2018-01-23 |
| CN107074729A (zh) | 2017-08-18 |
| BR112017007961B1 (pt) | 2021-12-28 |
| CA2965482A1 (en) | 2016-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |
|
| EEER | Examination request |
Effective date: 20200928 |