DE2152323C3 - Verfahren zur gleichzeitigen Herstellung von Trichloracrylsäure und organischen Säurechloriden - Google Patents
Verfahren zur gleichzeitigen Herstellung von Trichloracrylsäure und organischen SäurechloridenInfo
- Publication number
- DE2152323C3 DE2152323C3 DE2152323A DE2152323A DE2152323C3 DE 2152323 C3 DE2152323 C3 DE 2152323C3 DE 2152323 A DE2152323 A DE 2152323A DE 2152323 A DE2152323 A DE 2152323A DE 2152323 C3 DE2152323 C3 DE 2152323C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- hexachloropropene
- trichloroacrylic
- chloride
- organic acid
- 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
- WMUBNWIGNSIRDH-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoic acid Chemical compound OC(=O)C(Cl)=C(Cl)Cl WMUBNWIGNSIRDH-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 organic acid chlorides Chemical class 0.000 title description 2
- VFDYKPARTDCDCU-UHFFFAOYSA-N hexachloropropene Chemical compound ClC(Cl)=C(Cl)C(Cl)(Cl)Cl VFDYKPARTDCDCU-UHFFFAOYSA-N 0.000 claims description 25
- 150000007524 organic acids Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 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 description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 230000001476 alcoholic effect Effects 0.000 claims 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
- JHQWTQQYCNWHHX-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl 2,3,3-trichloroprop-2-eneperoxoate Chemical compound ClC(Cl)=C(Cl)C(=O)OOC(=O)C(Cl)=C(Cl)Cl JHQWTQQYCNWHHX-UHFFFAOYSA-N 0.000 description 1
- BCOSEZGCLGPUSL-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=C(Cl)C(Cl)=O BCOSEZGCLGPUSL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7037960A FR2109485A5 (enExample) | 1970-10-21 | 1970-10-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2152323A1 DE2152323A1 (de) | 1972-04-27 |
| DE2152323B2 DE2152323B2 (de) | 1975-04-10 |
| DE2152323C3 true DE2152323C3 (de) | 1975-11-20 |
Family
ID=9063045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2152323A Expired DE2152323C3 (de) | 1970-10-21 | 1971-10-20 | Verfahren zur gleichzeitigen Herstellung von Trichloracrylsäure und organischen Säurechloriden |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE774231A (enExample) |
| CA (1) | CA947315A (enExample) |
| DE (1) | DE2152323C3 (enExample) |
| ES (1) | ES396161A1 (enExample) |
| FR (1) | FR2109485A5 (enExample) |
| GB (1) | GB1320869A (enExample) |
| IL (1) | IL37969A (enExample) |
| IT (1) | IT942720B (enExample) |
| NL (1) | NL7113842A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7500046A (nl) * | 1974-01-11 | 1975-07-15 | Montedison Spa | Werkwijze voor de bereiding van nieuwe insek- e verbindingen. |
-
1970
- 1970-10-21 FR FR7037960A patent/FR2109485A5/fr not_active Expired
-
1971
- 1971-10-08 NL NL7113842A patent/NL7113842A/xx unknown
- 1971-10-19 IT IT70439/71A patent/IT942720B/it active
- 1971-10-19 IL IL37969A patent/IL37969A/xx unknown
- 1971-10-20 DE DE2152323A patent/DE2152323C3/de not_active Expired
- 1971-10-20 ES ES396161A patent/ES396161A1/es not_active Expired
- 1971-10-20 CA CA125,658A patent/CA947315A/en not_active Expired
- 1971-10-20 GB GB4873571A patent/GB1320869A/en not_active Expired
- 1971-10-20 BE BE774231A patent/BE774231A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2109485A5 (enExample) | 1972-05-26 |
| IL37969A (en) | 1974-06-30 |
| ES396161A1 (es) | 1974-04-01 |
| IL37969A0 (en) | 1971-12-29 |
| GB1320869A (en) | 1973-06-20 |
| IT942720B (it) | 1973-04-02 |
| CA947315A (en) | 1974-05-14 |
| BE774231A (fr) | 1972-04-20 |
| DE2152323B2 (de) | 1975-04-10 |
| NL7113842A (enExample) | 1972-04-25 |
| DE2152323A1 (de) | 1972-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |