CN101823962B - 制备顺丁烯二酸二甲酯的方法 - Google Patents
制备顺丁烯二酸二甲酯的方法 Download PDFInfo
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- CN101823962B CN101823962B CN2010101728677A CN201010172867A CN101823962B CN 101823962 B CN101823962 B CN 101823962B CN 2010101728677 A CN2010101728677 A CN 2010101728677A CN 201010172867 A CN201010172867 A CN 201010172867A CN 101823962 B CN101823962 B CN 101823962B
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- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 381
- 239000000463 material Substances 0.000 claims abstract description 206
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 117
- 238000006243 chemical reaction Methods 0.000 claims abstract description 95
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 79
- 238000005886 esterification reaction Methods 0.000 claims abstract description 66
- 239000007788 liquid Substances 0.000 claims abstract description 46
- 239000003377 acid catalyst Substances 0.000 claims abstract description 35
- 239000012535 impurity Substances 0.000 claims abstract description 27
- 238000000926 separation method Methods 0.000 claims abstract description 27
- 238000001704 evaporation Methods 0.000 claims abstract description 26
- 230000008020 evaporation Effects 0.000 claims abstract description 26
- 230000018044 dehydration Effects 0.000 claims abstract description 22
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 22
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims abstract description 21
- 239000007791 liquid phase Substances 0.000 claims abstract description 20
- 238000002156 mixing Methods 0.000 claims abstract description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 38
- -1 monomethyl cis-butenedioic acid Chemical compound 0.000 claims description 35
- 230000032050 esterification Effects 0.000 claims description 33
- 239000012071 phase Substances 0.000 claims description 19
- 238000009833 condensation Methods 0.000 claims description 18
- 230000005494 condensation Effects 0.000 claims description 18
- 239000007792 gaseous phase Substances 0.000 claims description 18
- 239000002994 raw material Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000011084 recovery Methods 0.000 claims description 12
- 239000007790 solid phase Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 8
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 230000008929 regeneration Effects 0.000 claims description 6
- 238000011069 regeneration method Methods 0.000 claims description 6
- 238000013517 stratification Methods 0.000 claims description 6
- 239000000292 calcium oxide Substances 0.000 claims description 4
- 235000012255 calcium oxide Nutrition 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000007787 solid Substances 0.000 abstract 2
- 238000005292 vacuum distillation Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 description 29
- 239000006227 byproduct Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
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Abstract
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CN2010101728677A CN101823962B (zh) | 2010-05-17 | 2010-05-17 | 制备顺丁烯二酸二甲酯的方法 |
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CN2010101728677A CN101823962B (zh) | 2010-05-17 | 2010-05-17 | 制备顺丁烯二酸二甲酯的方法 |
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CN101823962A CN101823962A (zh) | 2010-09-08 |
CN101823962B true CN101823962B (zh) | 2012-11-14 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103360206B (zh) * | 2012-04-01 | 2016-03-02 | 中国石油化工股份有限公司 | 生产1,4-丁二醇、四氢呋喃、γ-丁内酯和丁醇的方法 |
CN104557536B (zh) * | 2013-10-24 | 2016-03-30 | 中国石油化工股份有限公司 | 一种丁二酸单甲酯的制备方法 |
CN104478722A (zh) * | 2014-12-12 | 2015-04-01 | 江南大学 | 一种环己烷-1,2-二甲酸二(2-丙基庚)酯增塑剂的制备方法 |
CN114736144B (zh) * | 2022-04-27 | 2023-10-13 | 武汉百科药物开发有限公司 | 一种多库酯钙的工业制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1616400A (zh) * | 2004-09-23 | 2005-05-18 | 李文佳 | 反丁烯二酸单甲酯的制备工艺 |
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2010
- 2010-05-17 CN CN2010101728677A patent/CN101823962B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1616400A (zh) * | 2004-09-23 | 2005-05-18 | 李文佳 | 反丁烯二酸单甲酯的制备工艺 |
Non-Patent Citations (2)
Title |
---|
王莹淑等.顺丁烯二酸二甲酯的合成过程研究.《化学工程与装备》.2007,(第4期),第13-15,23页. * |
郝兴仁等.顺丁烯二酸二甲酯合成反应宏观动力学研究.《化学反应工程与工艺》.2002,第18卷(第2期),第103-108页. * |
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Address after: Hebei Dongguang County South 061600 DAZHANGZHUANG Patentee after: Choi Yue chemical (Cangzhou) Limited Address before: Cangzhou City, Hebei province 061600 DAZHANGZHUANG south of Dongguang County Patentee before: Cangzhou Ge Pharmaceutical Chemical Co., Ltd. |
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Address after: 061600 DAZHANGZHUANG, Chengnan, Dongguang County, Hebei Province Patentee after: Hebei caike New Material Technology Co.,Ltd. Address before: 061600 DAZHANGZHUANG, Chengnan, Dongguang County, Hebei Province Patentee before: TSAKER CHEMICAL (ZHANGZHOU) CO.,LTD. |
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