CN111875487A - 一种四甲基环丁二酮的制备方法 - Google Patents
一种四甲基环丁二酮的制备方法 Download PDFInfo
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- CN111875487A CN111875487A CN202010683346.1A CN202010683346A CN111875487A CN 111875487 A CN111875487 A CN 111875487A CN 202010683346 A CN202010683346 A CN 202010683346A CN 111875487 A CN111875487 A CN 111875487A
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- Prior art keywords
- absorption
- tetramethylcyclobutane
- dimethyl ketene
- temperature
- reactor
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- 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.)
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- -1 tetramethylcyclobutane ketone Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000010521 absorption reaction Methods 0.000 claims abstract description 98
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 claims abstract description 95
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 46
- 230000002745 absorbent Effects 0.000 claims abstract description 35
- 239000002250 absorbent Substances 0.000 claims abstract description 35
- YNJCGEDVIOLRLB-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclobutane Chemical compound CC1(C)CCC1(C)C YNJCGEDVIOLRLB-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 239000007791 liquid phase Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000002425 crystallisation Methods 0.000 claims abstract description 19
- 230000008025 crystallization Effects 0.000 claims abstract description 19
- 238000000926 separation method Methods 0.000 claims abstract description 19
- 238000001704 evaporation Methods 0.000 claims abstract description 15
- 230000008020 evaporation Effects 0.000 claims abstract description 15
- 239000012071 phase Substances 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 239000002002 slurry Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 29
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 12
- MJPHOVOZASUQHP-UHFFFAOYSA-N 3,3,4,4-tetramethylcyclobutane-1,2-dione Chemical compound CC1(C)C(=O)C(=O)C1(C)C MJPHOVOZASUQHP-UHFFFAOYSA-N 0.000 claims description 11
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 claims description 9
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical group CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 7
- JSLCOZYBKYHZNL-UHFFFAOYSA-N butylisobutyrate Chemical compound CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims description 6
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- AZFUASHXSOTBNU-UHFFFAOYSA-N Propyl 2-methylpropanoate Chemical compound CCCOC(=O)C(C)C AZFUASHXSOTBNU-UHFFFAOYSA-N 0.000 claims description 3
- 238000007664 blowing Methods 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000011084 recovery Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000012043 crude product Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 20
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000005336 cracking Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000861 blow drying Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VIJZZJKGTNSBLL-UHFFFAOYSA-N 1,1,3,3-tetramethylcyclobutane Chemical compound CC1(C)CC(C)(C)C1 VIJZZJKGTNSBLL-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/76—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton with the aid of ketenes
-
- 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
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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)
Abstract
Description
实施例12 | 实施例13 | 实施例14 | 实施例15 | |
DMK转化率(%) | 98.35 | 97.56 | 99.51 | 99.93 |
CBDK选择性(%) | 99.83 | 99.65 | 98.95 | 98.31 |
实施例16 | 实施例17 | 实施例18 | |
DMK转化率(%) | 91.53 | 99.01 | 99.58 |
CBDK选择性(%) | 99.55 | 99.48 | 99.67 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202010683346.1A CN111875487A (zh) | 2020-07-15 | 2020-07-15 | 一种四甲基环丁二酮的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN202010683346.1A CN111875487A (zh) | 2020-07-15 | 2020-07-15 | 一种四甲基环丁二酮的制备方法 |
Publications (1)
Publication Number | Publication Date |
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CN111875487A true CN111875487A (zh) | 2020-11-03 |
Family
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CN202010683346.1A Pending CN111875487A (zh) | 2020-07-15 | 2020-07-15 | 一种四甲基环丁二酮的制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN111875487A (zh) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3201474A (en) * | 1959-09-24 | 1965-08-17 | Eastman Kodak Co | Process of manufacturing dialkyl ketenes |
US5258556A (en) * | 1993-02-01 | 1993-11-02 | Eastman Kodak Company | Process for the manufacture of 2,2,4,4-tetramethylcyclobutanediol |
US20080154069A1 (en) * | 2006-12-02 | 2008-06-26 | Eastman Chemical Company | Process for the preparation of a tetraalkylcyclobutane-1,3-diol using an ruthenium-promoted cobalt-based catalyst |
CN105732354A (zh) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | 一种合成2,2,4,4-四甲基-1,3-环丁二酮的方法 |
KR20190054646A (ko) * | 2017-11-14 | 2019-05-22 | 롯데케미칼 주식회사 | 2,2,4,4-테트라메틸-1,3-사이클로부탄디올의 제조 방법 |
CN110105186A (zh) * | 2019-05-14 | 2019-08-09 | 浙江恒澜科技有限公司 | 一种制备烯酮类化合物的方法 |
TWI698423B (zh) * | 2019-03-21 | 2020-07-11 | 財團法人工業技術研究院 | 2,2,4,4-四甲基-1,3-環丁二酮的合成方法 |
-
2020
- 2020-07-15 CN CN202010683346.1A patent/CN111875487A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3201474A (en) * | 1959-09-24 | 1965-08-17 | Eastman Kodak Co | Process of manufacturing dialkyl ketenes |
US5258556A (en) * | 1993-02-01 | 1993-11-02 | Eastman Kodak Company | Process for the manufacture of 2,2,4,4-tetramethylcyclobutanediol |
WO1994018146A1 (en) * | 1993-02-01 | 1994-08-18 | Eastman Chemical Company | Process for the manufacture of 2,2,4,4-tetramethylcyclobutanediol |
US20080154069A1 (en) * | 2006-12-02 | 2008-06-26 | Eastman Chemical Company | Process for the preparation of a tetraalkylcyclobutane-1,3-diol using an ruthenium-promoted cobalt-based catalyst |
CN105732354A (zh) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | 一种合成2,2,4,4-四甲基-1,3-环丁二酮的方法 |
KR20190054646A (ko) * | 2017-11-14 | 2019-05-22 | 롯데케미칼 주식회사 | 2,2,4,4-테트라메틸-1,3-사이클로부탄디올의 제조 방법 |
TWI698423B (zh) * | 2019-03-21 | 2020-07-11 | 財團法人工業技術研究院 | 2,2,4,4-四甲基-1,3-環丁二酮的合成方法 |
CN110105186A (zh) * | 2019-05-14 | 2019-08-09 | 浙江恒澜科技有限公司 | 一种制备烯酮类化合物的方法 |
Non-Patent Citations (2)
Title |
---|
李燕: "《化工原理》", 31 July 2015, 延吉:延边大学出版社 * |
程光剑等: "2,2,4,4-四甲基-1,3-环丁二醇的合成技术及应用现状", 《石化技术与应用》 * |
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Address after: 311200 29 Chenghu Road, Yaqian Town, Xiaoshan District, Hangzhou City, Zhejiang Province Applicant after: Zhejiang Hengyi Petrochemical Research Institute Co.,Ltd. Applicant after: Zhejiang University Address before: 311200 Room 501, 3 Blocks, Pearl Plaza, South Bank of Xiaoshan Economic and Technological Development Zone, Xiaoshan District, Hangzhou City, Zhejiang Province Applicant before: ZHEJIANG HENGLAN TECHNOLOGY Co.,Ltd. Applicant before: Zhejiang University |
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Application publication date: 20201103 |