CA1159085A - PROCESS FOR THE PRODUCTION OF .alpha.-CHLOROACETOACETIC ACID CHLORIDE - Google Patents
PROCESS FOR THE PRODUCTION OF .alpha.-CHLOROACETOACETIC ACID CHLORIDEInfo
- Publication number
- CA1159085A CA1159085A CA000363082A CA363082A CA1159085A CA 1159085 A CA1159085 A CA 1159085A CA 000363082 A CA000363082 A CA 000363082A CA 363082 A CA363082 A CA 363082A CA 1159085 A CA1159085 A CA 1159085A
- Authority
- CA
- Canada
- Prior art keywords
- diketene
- chlorine
- inert solvent
- percent
- solvent
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 31
- 239000000460 chlorine Substances 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000012442 inert solvent Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 238000007700 distillative separation Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- -1 l-chlorobutane Chemical compound 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- YNKZSBSRKWVMEZ-UHFFFAOYSA-N bromo-chloro-fluoromethane Chemical compound FC(Cl)Br YNKZSBSRKWVMEZ-UHFFFAOYSA-N 0.000 description 1
- FMWLUWPQPKEARP-UHFFFAOYSA-N bromodichloromethane Chemical compound ClC(Cl)Br FMWLUWPQPKEARP-UHFFFAOYSA-N 0.000 description 1
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 1
- YSLFMGDEEXOKHF-UHFFFAOYSA-N difluoro(iodo)methane Chemical compound FC(F)I YSLFMGDEEXOKHF-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- RIHYOLCRHKZJPJ-UHFFFAOYSA-N fluoro(diiodo)methane Chemical compound FC(I)I RIHYOLCRHKZJPJ-UHFFFAOYSA-N 0.000 description 1
- XGVXNTVBGYLJIR-UHFFFAOYSA-N fluoroiodomethane Chemical compound FCI XGVXNTVBGYLJIR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9803/79 | 1979-11-01 | ||
| CH980379A CH642611A5 (de) | 1979-11-01 | 1979-11-01 | Verfahren zur herstellung von gamma-chloracetessigsaeurechlorid. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159085A true CA1159085A (en) | 1983-12-20 |
Family
ID=4355809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000363082A Expired CA1159085A (en) | 1979-11-01 | 1980-10-23 | PROCESS FOR THE PRODUCTION OF .alpha.-CHLOROACETOACETIC ACID CHLORIDE |
Country Status (15)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CH666483A5 (de) * | 1985-01-16 | 1988-07-29 | Lonza Ag | Verfahren zur herstellung von thiotetronsaeure. |
| CH667655A5 (de) * | 1986-09-24 | 1988-10-31 | Lonza Ag | Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen. |
| US5258523A (en) * | 1991-06-28 | 1993-11-02 | Lonza Ltd. | Process for the production of 2-aryl-2H-1,2,3-triazoles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950412A (en) * | 1971-06-08 | 1976-04-13 | Lonza Ltd. | Method for the production of haloacetoacetic acids |
| US3769338A (en) * | 1971-11-09 | 1973-10-30 | Ethyl Corp | Process for synthesizing citric acid |
| JPS4936210A (enrdf_load_stackoverflow) * | 1972-08-04 | 1974-04-04 | ||
| JPS5823373B2 (ja) * | 1975-03-27 | 1983-05-14 | 日本合成化学工業株式会社 | ガンマ− − クロルアセトサクサンクロライドノセイゾウホウホウ |
-
1979
- 1979-11-01 CH CH980379A patent/CH642611A5/de not_active IP Right Cessation
-
1980
- 1980-10-08 EP EP80106117A patent/EP0028709B1/de not_active Expired
- 1980-10-08 DE DE8080106117T patent/DE3071396D1/de not_active Expired
- 1980-10-08 AT AT80106117T patent/ATE17712T1/de not_active IP Right Cessation
- 1980-10-15 ZA ZA00806349A patent/ZA806349B/xx unknown
- 1980-10-23 CA CA000363082A patent/CA1159085A/en not_active Expired
- 1980-10-28 JP JP15024480A patent/JPS5675454A/ja active Granted
- 1980-10-29 BR BR8006943A patent/BR8006943A/pt not_active IP Right Cessation
- 1980-10-29 CS CS807319A patent/CS215076B2/cs unknown
- 1980-10-30 DD DD80224838A patent/DD153825A5/de not_active IP Right Cessation
- 1980-10-30 MX MX184562A patent/MX155608A/es unknown
- 1980-10-31 AR AR283087A patent/AR223902A1/es active
- 1980-10-31 HU HU802635A patent/HU185915B/hu not_active IP Right Cessation
- 1980-10-31 PL PL1980227594A patent/PL126702B1/pl unknown
- 1980-10-31 ES ES496428A patent/ES496428A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH642611A5 (de) | 1984-04-30 |
| ES8107144A1 (es) | 1981-10-01 |
| ZA806349B (en) | 1981-10-28 |
| ES496428A0 (es) | 1981-10-01 |
| EP0028709B1 (de) | 1986-01-29 |
| BR8006943A (pt) | 1981-05-05 |
| JPS5675454A (en) | 1981-06-22 |
| AR223902A1 (es) | 1981-09-30 |
| DE3071396D1 (en) | 1986-03-13 |
| HU185915B (en) | 1985-04-28 |
| MX155608A (es) | 1988-04-06 |
| PL126702B1 (en) | 1983-08-31 |
| JPH0244825B2 (enrdf_load_stackoverflow) | 1990-10-05 |
| ATE17712T1 (de) | 1986-02-15 |
| DD153825A5 (de) | 1982-02-03 |
| EP0028709A1 (de) | 1981-05-20 |
| CS215076B2 (en) | 1982-07-30 |
| PL227594A1 (enrdf_load_stackoverflow) | 1981-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |