GB871836A - Improvements in or relating to methods of synthesizing 2, 4, 4, 4-tetrachloro-butyric acid - Google Patents
Improvements in or relating to methods of synthesizing 2, 4, 4, 4-tetrachloro-butyric acidInfo
- Publication number
- GB871836A GB871836A GB9549/58A GB954958A GB871836A GB 871836 A GB871836 A GB 871836A GB 9549/58 A GB9549/58 A GB 9549/58A GB 954958 A GB954958 A GB 954958A GB 871836 A GB871836 A GB 871836A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetate
- acid
- tetrachlorobutyric
- tetrachlorobutanol
- hours
- 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
- DSTQWCFEDAQVAU-UHFFFAOYSA-N 2,4,4,4-tetrachlorobutanoic acid Chemical compound OC(=O)C(Cl)CC(Cl)(Cl)Cl DSTQWCFEDAQVAU-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- PNDXSZVXDBLZCY-UHFFFAOYSA-N 1,1,2,2-tetrachlorobutan-1-ol Chemical compound CCC(Cl)(Cl)C(O)(Cl)Cl PNDXSZVXDBLZCY-UHFFFAOYSA-N 0.000 abstract 1
- QFPRKSPAULXGPL-UHFFFAOYSA-N 2,2,3,3-tetrachlorobutanoic acid Chemical compound CC(Cl)(Cl)C(Cl)(Cl)C(O)=O QFPRKSPAULXGPL-UHFFFAOYSA-N 0.000 abstract 1
- PHPDBVLDVIRSHU-UHFFFAOYSA-N 2,4,4,4-tetrachlorobutan-1-ol Chemical compound OCC(Cl)CC(Cl)(Cl)Cl PHPDBVLDVIRSHU-UHFFFAOYSA-N 0.000 abstract 1
- GOMNSEFSMITHSC-UHFFFAOYSA-N 2,4,4,4-tetrachlorobutyl acetate Chemical compound CC(=O)OCC(Cl)CC(Cl)(Cl)Cl GOMNSEFSMITHSC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
2,4,4,4-Tetrachlorobutyric acid is prepared by reacting carbon tetrachloride with allyl acetate in the presence of a peroxide or other catalyst capable of releasing free radicals or of ultra-violet light, the reaction being carried out by bringing the reactants together very gradually, whereby 2,4,4,4 - tetrachlorobutyl acetate is formed, converting the said acetate into 2,4,4,4-tetrachlorobutanol by alcoholysis of the acetate in the presence of 0.001 to 0.1 moles of hydrochloric, sulphuric or phosphoric acid per mole of the acetate, and oxidation of the tetrachlorobutanol to 2,4,4,4-tetrachlorobutyric acid with from 25 to 100% excess chromic anhydride in solution in aqueous acetic acid over a period of at least 5 hours, the reaction mixture being strongly cooled during the addition of the chromic anhydride and then left at room temperature for a time necessary for the formation of the tetrachlorobutyric acid, or held at a temperature of 30 DEG to 40 DEG C. for from 1 to 2 hours.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1109662X | 1957-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB871836A true GB871836A (en) | 1961-07-05 |
Family
ID=9625771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9549/58A Expired GB871836A (en) | 1957-04-11 | 1958-03-25 | Improvements in or relating to methods of synthesizing 2, 4, 4, 4-tetrachloro-butyric acid |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1109662B (en) |
| FR (1) | FR1171147A (en) |
| GB (1) | GB871836A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750773A (en) * | 1995-07-17 | 1998-05-12 | Zeneca Limited | Process for preparing 4,4,4-trichlorobutyl acetate |
-
1957
- 1957-04-11 FR FR1171147D patent/FR1171147A/en not_active Expired
-
1958
- 1958-03-25 GB GB9549/58A patent/GB871836A/en not_active Expired
- 1958-04-10 DE DER23101A patent/DE1109662B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750773A (en) * | 1995-07-17 | 1998-05-12 | Zeneca Limited | Process for preparing 4,4,4-trichlorobutyl acetate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1109662B (en) | 1961-06-29 |
| FR1171147A (en) | 1959-01-22 |
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