CN103833537A - Absorption and refining method for high-purity methylacrolein - Google Patents
Absorption and refining method for high-purity methylacrolein Download PDFInfo
- Publication number
- CN103833537A CN103833537A CN201410071066.XA CN201410071066A CN103833537A CN 103833537 A CN103833537 A CN 103833537A CN 201410071066 A CN201410071066 A CN 201410071066A CN 103833537 A CN103833537 A CN 103833537A
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- Prior art keywords
- absorption
- tower
- purification
- purity
- removing column
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- 238000010521 absorption reaction Methods 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims abstract description 37
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 title abstract 8
- 238000007670 refining Methods 0.000 title abstract 3
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 53
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 15
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 13
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 claims description 8
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 claims description 8
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 6
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 4
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 claims description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
- 238000005265 energy consumption Methods 0.000 abstract description 11
- 239000000543 intermediate Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract 2
- 239000002250 absorbent Substances 0.000 abstract 2
- 239000012847 fine chemical Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000006709 oxidative esterification reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410071066.XA CN103833537B (en) | 2014-02-28 | 2014-02-28 | Absorption and refining method for high-purity methylacrolein |
Applications Claiming Priority (1)
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CN201410071066.XA CN103833537B (en) | 2014-02-28 | 2014-02-28 | Absorption and refining method for high-purity methylacrolein |
Publications (2)
Publication Number | Publication Date |
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CN103833537A true CN103833537A (en) | 2014-06-04 |
CN103833537B CN103833537B (en) | 2015-04-01 |
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CN201410071066.XA Active CN103833537B (en) | 2014-02-28 | 2014-02-28 | Absorption and refining method for high-purity methylacrolein |
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CN (1) | CN103833537B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109467610A (en) * | 2018-11-27 | 2019-03-15 | 华南理工大学 | A kind of method that acetate starch production process and row prepare high substituted degree crosslinked starch |
CN110256395A (en) * | 2019-07-02 | 2019-09-20 | 菏泽学院 | A kind of synthetic method of 4,4- dimethyl-2-isopropyl -1,3- dioxolane |
CN113845409A (en) * | 2021-10-18 | 2021-12-28 | 浙江皇马科技股份有限公司 | Absorption and refining method of high-purity methacrolein |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003192627A (en) * | 2001-12-27 | 2003-07-09 | Mitsubishi Rayon Co Ltd | Method for producing methacrolein |
CN101020625A (en) * | 2007-03-12 | 2007-08-22 | 中国科学院过程工程研究所 | Process of absorbing methyl acraldehyde with ionic liquid |
CN101844973A (en) * | 2010-06-01 | 2010-09-29 | 上海华谊丙烯酸有限公司 | Method for absorbing and separating methacrolein |
US8273313B2 (en) * | 2007-02-14 | 2012-09-25 | Saudi Basic Industries Corporation | System for producing methacrylic acid |
-
2014
- 2014-02-28 CN CN201410071066.XA patent/CN103833537B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003192627A (en) * | 2001-12-27 | 2003-07-09 | Mitsubishi Rayon Co Ltd | Method for producing methacrolein |
US8273313B2 (en) * | 2007-02-14 | 2012-09-25 | Saudi Basic Industries Corporation | System for producing methacrylic acid |
CN101020625A (en) * | 2007-03-12 | 2007-08-22 | 中国科学院过程工程研究所 | Process of absorbing methyl acraldehyde with ionic liquid |
CN101844973A (en) * | 2010-06-01 | 2010-09-29 | 上海华谊丙烯酸有限公司 | Method for absorbing and separating methacrolein |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109467610A (en) * | 2018-11-27 | 2019-03-15 | 华南理工大学 | A kind of method that acetate starch production process and row prepare high substituted degree crosslinked starch |
CN110256395A (en) * | 2019-07-02 | 2019-09-20 | 菏泽学院 | A kind of synthetic method of 4,4- dimethyl-2-isopropyl -1,3- dioxolane |
CN113845409A (en) * | 2021-10-18 | 2021-12-28 | 浙江皇马科技股份有限公司 | Absorption and refining method of high-purity methacrolein |
Also Published As
Publication number | Publication date |
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CN103833537B (en) | 2015-04-01 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Absorption and refining method for high-purity methylacrolein Effective date of registration: 20170615 Granted publication date: 20150401 Pledgee: Heze rural commercial bank Limited by Share Ltd Pledgor: Shandong Yidali Chemical Co., Ltd. Registration number: 2017990000489 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20180727 Granted publication date: 20150401 Pledgee: Heze rural commercial bank Limited by Share Ltd Pledgor: Shandong Yidali Chemical Co., Ltd. Registration number: 2017990000489 |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180929 Address after: 274000 Shandong province Heze Development Zone Haihe road to the North Patentee after: Heze HOLLEY New Material Co Ltd Address before: 274000 Haihe Road, Heze Development Zone, Shandong Province Patentee before: Shandong Yidali Chemical Co., Ltd. |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20140604 Assignee: Zibo Qixian Tengda Chemical Co., Ltd. Assignor: Heze HOLLEY New Material Co Ltd Contract record no.: 2018370000065 Denomination of invention: Absorption and refining method for high-purity methylacrolein Granted publication date: 20150401 License type: Exclusive License Record date: 20181214 |
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CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: No. 333, Haihe Road, Heze Development Zone, 274000 Shandong Province Patentee after: Qixiang Huali New Material Co., Ltd Address before: 274000 Shandong province Heze Development Zone Haihe road to the North Patentee before: HEZE HUALI NEW MATERIAL Co.,Ltd. |