CN103420833A - 一种对甲苯磺酸催化的丙二酸二甲酯合成方法 - Google Patents
一种对甲苯磺酸催化的丙二酸二甲酯合成方法 Download PDFInfo
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- CN103420833A CN103420833A CN2013103488402A CN201310348840A CN103420833A CN 103420833 A CN103420833 A CN 103420833A CN 2013103488402 A CN2013103488402 A CN 2013103488402A CN 201310348840 A CN201310348840 A CN 201310348840A CN 103420833 A CN103420833 A CN 103420833A
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- Prior art keywords
- acid
- reaction
- dimethyl malonate
- catalyzed
- esterification
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- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000005886 esterification reaction Methods 0.000 claims abstract description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000020477 pH reduction Effects 0.000 claims abstract description 11
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 7
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 30
- 230000032050 esterification Effects 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 13
- 238000010189 synthetic method Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- NLBFDFIZQKPFKP-UHFFFAOYSA-N [Na].C(#N)CC(=O)O Chemical compound [Na].C(#N)CC(=O)O NLBFDFIZQKPFKP-UHFFFAOYSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000010612 desalination reaction Methods 0.000 claims description 8
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010025 steaming Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 5
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- SJELIDWGIUVECV-UHFFFAOYSA-N methanol;propanedioic acid Chemical compound OC.OC(=O)CC(O)=O SJELIDWGIUVECV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000002386 leaching Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229940106681 chloroacetic acid Drugs 0.000 abstract 1
- 238000007333 cyanation reaction Methods 0.000 abstract 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- HUBWASIQNZELSG-UHFFFAOYSA-N [Ca].C(#N)CC(=O)O Chemical compound [Ca].C(#N)CC(=O)O HUBWASIQNZELSG-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019600 saltiness Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- -1 stir 30 minutes Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
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- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Claims (8)
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CN201310348840.2A CN103420833B (zh) | 2013-08-12 | 2013-08-12 | 一种对甲苯磺酸催化的丙二酸二甲酯合成方法 |
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CN201310348840.2A CN103420833B (zh) | 2013-08-12 | 2013-08-12 | 一种对甲苯磺酸催化的丙二酸二甲酯合成方法 |
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CN103420833A true CN103420833A (zh) | 2013-12-04 |
CN103420833B CN103420833B (zh) | 2015-09-16 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103724191A (zh) * | 2014-01-28 | 2014-04-16 | 重庆紫光化工股份有限公司 | 丙二酸二甲酯制备方法 |
CN103936588A (zh) * | 2014-03-31 | 2014-07-23 | 河北诚信有限责任公司 | 制备丙二酸酯的绿色清洁工艺 |
CN104072369A (zh) * | 2014-07-15 | 2014-10-01 | 潍坊滨海石油化工有限公司 | 一种制备丙二酸二异丙酯的工艺 |
CN105294491A (zh) * | 2015-11-20 | 2016-02-03 | 重庆紫光化工股份有限公司 | 一种氰乙酸及其衍生物的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1222503A (zh) * | 1998-11-23 | 1999-07-14 | 河北省固安县宏峰化工有限公司 | 柠檬酸三甲酯的合成方法 |
JP2002030071A (ja) * | 2000-07-19 | 2002-01-29 | Fuji Photo Film Co Ltd | 3,5−ピラゾリジンジオン化合物の製造方法 |
CN1834081A (zh) * | 2006-04-20 | 2006-09-20 | 重庆紫光化工有限责任公司 | 丙二酸酯的制备方法 |
CN101066921A (zh) * | 2007-06-14 | 2007-11-07 | 重庆紫光化工有限责任公司 | 丙二酸酯的制备方法 |
CN101838377A (zh) * | 2010-05-11 | 2010-09-22 | 张春华 | 可辐射固化的多官能(甲基)丙烯酸酯的组合物 |
-
2013
- 2013-08-12 CN CN201310348840.2A patent/CN103420833B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1222503A (zh) * | 1998-11-23 | 1999-07-14 | 河北省固安县宏峰化工有限公司 | 柠檬酸三甲酯的合成方法 |
JP2002030071A (ja) * | 2000-07-19 | 2002-01-29 | Fuji Photo Film Co Ltd | 3,5−ピラゾリジンジオン化合物の製造方法 |
CN1834081A (zh) * | 2006-04-20 | 2006-09-20 | 重庆紫光化工有限责任公司 | 丙二酸酯的制备方法 |
CN101066921A (zh) * | 2007-06-14 | 2007-11-07 | 重庆紫光化工有限责任公司 | 丙二酸酯的制备方法 |
CN101838377A (zh) * | 2010-05-11 | 2010-09-22 | 张春华 | 可辐射固化的多官能(甲基)丙烯酸酯的组合物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103724191A (zh) * | 2014-01-28 | 2014-04-16 | 重庆紫光化工股份有限公司 | 丙二酸二甲酯制备方法 |
CN103936588A (zh) * | 2014-03-31 | 2014-07-23 | 河北诚信有限责任公司 | 制备丙二酸酯的绿色清洁工艺 |
CN104072369A (zh) * | 2014-07-15 | 2014-10-01 | 潍坊滨海石油化工有限公司 | 一种制备丙二酸二异丙酯的工艺 |
CN105294491A (zh) * | 2015-11-20 | 2016-02-03 | 重庆紫光化工股份有限公司 | 一种氰乙酸及其衍生物的制备方法 |
CN105294491B (zh) * | 2015-11-20 | 2017-06-23 | 重庆紫光化工股份有限公司 | 一种氰乙酸及其衍生物的制备方法 |
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CN103420833B (zh) | 2015-09-16 |
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C06 | Publication | ||
PB01 | Publication | ||
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A synthesis method of dimethyl Malonate Catalyzed by p-toluenesulfonic acid Effective date of registration: 20210809 Granted publication date: 20150916 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2021500000036 |
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Date of cancellation: 20220727 Granted publication date: 20150916 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2021500000036 |
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PC01 | Cancellation 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: A kind of synthetic method of dimethyl malonate catalyzed by p-toluenesulfonic acid Effective date of registration: 20220811 Granted publication date: 20150916 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2022500000056 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
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Date of cancellation: 20230310 Granted publication date: 20150916 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2022500000056 |
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Denomination of invention: A Synthesis Method of Dimethyl Malonate Catalyzed by p-Toluenesulfonic Acid Effective date of registration: 20230317 Granted publication date: 20150916 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2023500000020 |
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