CS217995B2 - Method of making the ester of the 2-chloracetovinegar acid - Google Patents
Method of making the ester of the 2-chloracetovinegar acid Download PDFInfo
- Publication number
- CS217995B2 CS217995B2 CS812363A CS236381A CS217995B2 CS 217995 B2 CS217995 B2 CS 217995B2 CS 812363 A CS812363 A CS 812363A CS 236381 A CS236381 A CS 236381A CS 217995 B2 CS217995 B2 CS 217995B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chloride
- acid
- diketene
- temperatures
- chlorine
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 title description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- -1 2-chloroacetic acid ester Chemical class 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- WNVYZJSJUQUVSZ-UHFFFAOYSA-N 2-chloro-3-oxobutanoyl chloride Chemical compound CC(=O)C(Cl)C(Cl)=O WNVYZJSJUQUVSZ-UHFFFAOYSA-N 0.000 abstract 2
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH260680 | 1980-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS217995B2 true CS217995B2 (en) | 1983-02-25 |
Family
ID=4237538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS812363A CS217995B2 (en) | 1980-04-02 | 1981-03-30 | Method of making the ester of the 2-chloracetovinegar acid |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0037015B1 (es) |
| JP (1) | JPS56154438A (es) |
| AT (1) | ATE3852T1 (es) |
| CS (1) | CS217995B2 (es) |
| DD (1) | DD157794A5 (es) |
| DE (1) | DE3160460D1 (es) |
| IN (1) | IN151753B (es) |
| MX (1) | MX152284A (es) |
| PL (1) | PL134443B1 (es) |
| SU (1) | SU988187A3 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65246A (en) * | 1981-03-26 | 1985-11-29 | Lonza Ag | Process for the preparation of 2-chloroacetoacetamides |
| JPS6025955A (ja) * | 1983-07-22 | 1985-02-08 | Nippon Synthetic Chem Ind Co Ltd:The | γ−クロルアセト酢酸エステルの製造方法 |
| CA2987775C (en) | 2011-04-01 | 2019-01-08 | Lonza Ltd | Preparation of 3,5-dioxo hexanoate ester in two steps |
| EP3383874A1 (de) | 2015-12-03 | 2018-10-10 | Bayer CropScience Aktiengesellschaft | Mesolonische halogenierte 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olat derivate und verwandte verbindungen als insektizide |
| CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
| CN109503381B (zh) * | 2018-12-12 | 2022-04-29 | 安徽金禾实业股份有限公司 | 4-氯乙酰乙酸乙酯微通道反应方法及装置 |
| CN113877504A (zh) * | 2021-11-03 | 2022-01-04 | 江苏恒安化工有限公司 | 一种4-氯乙酰乙酸乙酯的制备装置及方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2209683A (en) * | 1936-06-27 | 1940-07-30 | Carbide & Carbon Chem Corp | Halogenation of diketene |
| CH492670A (de) * | 1968-04-24 | 1970-06-30 | Lonza Ag | Verfahren zur Herstellung von y-Chloracetessigsäureester |
-
1981
- 1981-03-12 IN IN271/CAL/81A patent/IN151753B/en unknown
- 1981-03-18 DE DE8181102029T patent/DE3160460D1/de not_active Expired
- 1981-03-18 AT AT81102029T patent/ATE3852T1/de not_active IP Right Cessation
- 1981-03-18 EP EP81102029A patent/EP0037015B1/de not_active Expired
- 1981-03-26 PL PL1981230340A patent/PL134443B1/pl unknown
- 1981-03-30 CS CS812363A patent/CS217995B2/cs unknown
- 1981-03-30 SU SU813262355A patent/SU988187A3/ru active
- 1981-03-31 DD DD81228780A patent/DD157794A5/de unknown
- 1981-04-01 JP JP4924781A patent/JPS56154438A/ja active Granted
- 1981-04-02 MX MX186693A patent/MX152284A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD157794A5 (de) | 1982-12-08 |
| ATE3852T1 (de) | 1983-07-15 |
| EP0037015A3 (en) | 1981-12-30 |
| MX152284A (es) | 1985-06-20 |
| JPS56154438A (en) | 1981-11-30 |
| PL134443B1 (en) | 1985-08-31 |
| JPH0125735B2 (es) | 1989-05-19 |
| SU988187A3 (ru) | 1983-01-07 |
| EP0037015B1 (de) | 1983-06-22 |
| EP0037015A2 (de) | 1981-10-07 |
| DE3160460D1 (en) | 1983-07-28 |
| PL230340A1 (es) | 1981-11-27 |
| IN151753B (es) | 1983-07-23 |
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