JPS597136A - マロン酸エステルの製法 - Google Patents
マロン酸エステルの製法Info
- Publication number
- JPS597136A JPS597136A JP11663082A JP11663082A JPS597136A JP S597136 A JPS597136 A JP S597136A JP 11663082 A JP11663082 A JP 11663082A JP 11663082 A JP11663082 A JP 11663082A JP S597136 A JPS597136 A JP S597136A
- Authority
- JP
- Japan
- Prior art keywords
- water
- reaction
- malonic acid
- liquid
- acid ester
- 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.)
- Granted
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 30
- -1 malonic acid ester Chemical class 0.000 title claims abstract description 21
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- JAUCIKCNYHCSIR-UHFFFAOYSA-M sodium;2-cyanoacetate Chemical compound [Na+].[O-]C(=O)CC#N JAUCIKCNYHCSIR-UHFFFAOYSA-M 0.000 claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 38
- 239000003960 organic solvent Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000011541 reaction mixture Substances 0.000 abstract description 7
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 description 20
- 239000010410 layer Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CUHBTBZRFUWVNF-UHFFFAOYSA-N 3-amino-3-oxopropanoic acid;sulfuric acid Chemical compound OS(O)(=O)=O.NC(=O)CC(O)=O CUHBTBZRFUWVNF-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- QRVSDVDFJFKYKA-UHFFFAOYSA-N dipropan-2-yl propanedioate Chemical compound CC(C)OC(=O)CC(=O)OC(C)C QRVSDVDFJFKYKA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KNWQCSNHLISUDU-UHFFFAOYSA-N acetamide;sulfuric acid Chemical compound CC(N)=O.OS(O)(=O)=O KNWQCSNHLISUDU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 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 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11663082A JPS597136A (ja) | 1982-07-05 | 1982-07-05 | マロン酸エステルの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11663082A JPS597136A (ja) | 1982-07-05 | 1982-07-05 | マロン酸エステルの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS597136A true JPS597136A (ja) | 1984-01-14 |
| JPH0142254B2 JPH0142254B2 (en, 2012) | 1989-09-11 |
Family
ID=14691946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11663082A Granted JPS597136A (ja) | 1982-07-05 | 1982-07-05 | マロン酸エステルの製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS597136A (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999008988A1 (en) * | 1997-08-13 | 1999-02-25 | Trikem S.A. | Malonic acid and esters thereof |
| CN1059430C (zh) * | 1997-05-27 | 2000-12-13 | 淄博东风化工厂 | 丙二酸酯的生产方法 |
| CN100424066C (zh) * | 2006-04-20 | 2008-10-08 | 重庆紫光化工股份有限公司 | 丙二酸酯的制备方法 |
| 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 |
-
1982
- 1982-07-05 JP JP11663082A patent/JPS597136A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1059430C (zh) * | 1997-05-27 | 2000-12-13 | 淄博东风化工厂 | 丙二酸酯的生产方法 |
| WO1999008988A1 (en) * | 1997-08-13 | 1999-02-25 | Trikem S.A. | Malonic acid and esters thereof |
| US6395931B1 (en) | 1997-08-13 | 2002-05-28 | Trikem S.A. | Malonic acid and esters thereof |
| CN100424066C (zh) * | 2006-04-20 | 2008-10-08 | 重庆紫光化工股份有限公司 | 丙二酸酯的制备方法 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0142254B2 (en, 2012) | 1989-09-11 |
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