DE2130629C3 - Verfahren zur Herstellung von selek tiv in 3 Stellung mono oder dichloner tem Butanon - Google Patents
Verfahren zur Herstellung von selek tiv in 3 Stellung mono oder dichloner tem ButanonInfo
- Publication number
- DE2130629C3 DE2130629C3 DE2130629A DE2130629A DE2130629C3 DE 2130629 C3 DE2130629 C3 DE 2130629C3 DE 2130629 A DE2130629 A DE 2130629A DE 2130629 A DE2130629 A DE 2130629A DE 2130629 C3 DE2130629 C3 DE 2130629C3
- Authority
- DE
- Germany
- Prior art keywords
- butanone
- reaction
- chloride
- production
- copper
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000003963 dichloro group Chemical group Cl* 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 238000005660 chlorination reaction Methods 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000000717 retained effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- 239000007789 gas Substances 0.000 description 6
- WBVOVRCGXKWAQT-UHFFFAOYSA-N 3,3-dichlorobutan-2-one Chemical compound CC(=O)C(C)(Cl)Cl WBVOVRCGXKWAQT-UHFFFAOYSA-N 0.000 description 5
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2130629A DE2130629C3 (de) | 1971-06-21 | 1971-06-21 | Verfahren zur Herstellung von selek tiv in 3 Stellung mono oder dichloner tem Butanon |
| US00258161A US3843731A (en) | 1971-06-21 | 1972-05-31 | Process for preparing butanone selectively mono-or dichloro-substituted in 3-position |
| IT50780/72A IT965818B (it) | 1971-06-21 | 1972-06-09 | Procedimento per produrre butanone mono o biclorurato e prodotto cosi ottenuto |
| JP47059976A JPS5034531B1 (https=) | 1971-06-21 | 1972-06-15 | |
| GB2851472A GB1367373A (en) | 1971-06-21 | 1972-06-19 | Process for the manufacture of butanone selectively monochlorinated or dichlorinated in the 3-position |
| FR727222157A FR2143103B1 (https=) | 1971-06-21 | 1972-06-20 | |
| CH921972A CH567446A5 (https=) | 1971-06-21 | 1972-06-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2130629A DE2130629C3 (de) | 1971-06-21 | 1971-06-21 | Verfahren zur Herstellung von selek tiv in 3 Stellung mono oder dichloner tem Butanon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2130629A1 DE2130629A1 (de) | 1973-01-11 |
| DE2130629B2 DE2130629B2 (de) | 1973-05-03 |
| DE2130629C3 true DE2130629C3 (de) | 1973-11-22 |
Family
ID=5811305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2130629A Expired DE2130629C3 (de) | 1971-06-21 | 1971-06-21 | Verfahren zur Herstellung von selek tiv in 3 Stellung mono oder dichloner tem Butanon |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3843731A (https=) |
| JP (1) | JPS5034531B1 (https=) |
| CH (1) | CH567446A5 (https=) |
| DE (1) | DE2130629C3 (https=) |
| FR (1) | FR2143103B1 (https=) |
| GB (1) | GB1367373A (https=) |
| IT (1) | IT965818B (https=) |
-
1971
- 1971-06-21 DE DE2130629A patent/DE2130629C3/de not_active Expired
-
1972
- 1972-05-31 US US00258161A patent/US3843731A/en not_active Expired - Lifetime
- 1972-06-09 IT IT50780/72A patent/IT965818B/it active
- 1972-06-15 JP JP47059976A patent/JPS5034531B1/ja active Pending
- 1972-06-19 GB GB2851472A patent/GB1367373A/en not_active Expired
- 1972-06-20 FR FR727222157A patent/FR2143103B1/fr not_active Expired
- 1972-06-20 CH CH921972A patent/CH567446A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2143103A1 (https=) | 1973-02-02 |
| GB1367373A (en) | 1974-09-18 |
| US3843731A (en) | 1974-10-22 |
| IT965818B (it) | 1974-02-11 |
| DE2130629B2 (de) | 1973-05-03 |
| FR2143103B1 (https=) | 1974-07-05 |
| JPS5034531B1 (https=) | 1975-11-10 |
| DE2130629A1 (de) | 1973-01-11 |
| CH567446A5 (https=) | 1975-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |