DE2223239C3 - Verfahren zur Herstellung von 2-Chlor-äthanphosphonsäure BASF AG, 6700 Ludwigshafen - Google Patents
Verfahren zur Herstellung von 2-Chlor-äthanphosphonsäure BASF AG, 6700 LudwigshafenInfo
- Publication number
- DE2223239C3 DE2223239C3 DE2223239A DE2223239A DE2223239C3 DE 2223239 C3 DE2223239 C3 DE 2223239C3 DE 2223239 A DE2223239 A DE 2223239A DE 2223239 A DE2223239 A DE 2223239A DE 2223239 C3 DE2223239 C3 DE 2223239C3
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic acid
- chloroethane
- cleavage
- reaction
- chloroethane phosphonic
- 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 description 23
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 title claims description 13
- 239000003795 chemical substances by application Substances 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000003776 cleavage reaction Methods 0.000 claims description 11
- 230000007017 scission Effects 0.000 claims description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 8
- 231100000331 toxic Toxicity 0.000 description 8
- 230000002588 toxic effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- -1 chloroethyl ester Chemical class 0.000 description 4
- 238000007257 deesterification reaction Methods 0.000 description 4
- CNGZUJQPNVPPCJ-UHFFFAOYSA-N 1-chloroethylphosphonic acid Chemical compound CC(Cl)P(O)(O)=O CNGZUJQPNVPPCJ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 101001059930 Drosophila melanogaster Transcription factor kayak, isoforms A/B/F Proteins 0.000 description 2
- 101001059931 Drosophila melanogaster Transcription factor kayak, isoforms D/sro Proteins 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- SEHJHHHUIGULEI-UHFFFAOYSA-N 2-hydroxyethylphosphonic acid Chemical compound OCCP(O)(O)=O SEHJHHHUIGULEI-UHFFFAOYSA-N 0.000 description 1
- 206010004966 Bite Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
- C07F9/425—Acid or estermonohalides thereof, e.g. RP(=X)(YR)(Hal) (X, Y = O, S; R = H, or hydrocarbon group)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2223239A DE2223239C3 (de) | 1972-05-12 | 1972-05-12 | Verfahren zur Herstellung von 2-Chlor-äthanphosphonsäure BASF AG, 6700 Ludwigshafen |
| JP4230173A JPS5550958B2 (US08063081-20111122-C00044.png) | 1972-05-12 | 1973-04-16 | |
| US00351155A US3833645A (en) | 1972-05-12 | 1973-04-16 | Preparation of 2-chloroethane-phosphonic acid |
| IL42055A IL42055A (en) | 1972-05-12 | 1973-04-18 | Preparation of 2-chloroethanephosphonic acid |
| CH645773A CH570412A5 (US08063081-20111122-C00044.png) | 1972-05-12 | 1973-05-07 | |
| ZA733099A ZA733099B (en) | 1972-05-12 | 1973-05-08 | Preparation of 2-chloroethanephosphonic acid |
| NLAANVRAGE7306543,A NL180834C (nl) | 1972-05-12 | 1973-05-10 | Werkwijze voor de bereiding van 2-chloorethaanfosfonzuur. |
| FR7317180A FR2184748B1 (US08063081-20111122-C00044.png) | 1972-05-12 | 1973-05-11 | |
| SU1920010A SU475782A3 (ru) | 1972-05-12 | 1973-05-11 | Способ получени 2-хлорэтилфосфоновой кислоты |
| GB2248973A GB1422362A (en) | 1972-05-12 | 1973-05-11 | Preparation of 2-chlorethanephosphonic acid |
| BE131029A BE799431A (fr) | 1972-05-12 | 1973-05-11 | Procede de preparation d'acide chloro-2-ethane-phosphonique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2223239A DE2223239C3 (de) | 1972-05-12 | 1972-05-12 | Verfahren zur Herstellung von 2-Chlor-äthanphosphonsäure BASF AG, 6700 Ludwigshafen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2223239A1 DE2223239A1 (de) | 1973-11-22 |
| DE2223239B2 DE2223239B2 (de) | 1980-04-24 |
| DE2223239C3 true DE2223239C3 (de) | 1981-01-15 |
Family
ID=5844755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2223239A Expired DE2223239C3 (de) | 1972-05-12 | 1972-05-12 | Verfahren zur Herstellung von 2-Chlor-äthanphosphonsäure BASF AG, 6700 Ludwigshafen |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3896163A (en) * | 1974-05-31 | 1975-07-22 | Amchem Prod | Purification of aliphatic phosphonic acids |
| US4728466A (en) * | 1985-10-18 | 1988-03-01 | Rhone-Poulenc Nederland B.V. | Process for the production of aliphatic phosphonic acids |
-
1972
- 1972-05-12 DE DE2223239A patent/DE2223239C3/de not_active Expired
-
1973
- 1973-04-16 US US00351155A patent/US3833645A/en not_active Expired - Lifetime
- 1973-04-16 JP JP4230173A patent/JPS5550958B2/ja not_active Expired
- 1973-04-18 IL IL42055A patent/IL42055A/xx unknown
- 1973-05-07 CH CH645773A patent/CH570412A5/xx not_active IP Right Cessation
- 1973-05-08 ZA ZA733099A patent/ZA733099B/xx unknown
- 1973-05-10 NL NLAANVRAGE7306543,A patent/NL180834C/xx not_active IP Right Cessation
- 1973-05-11 FR FR7317180A patent/FR2184748B1/fr not_active Expired
- 1973-05-11 GB GB2248973A patent/GB1422362A/en not_active Expired
- 1973-05-11 SU SU1920010A patent/SU475782A3/ru active
- 1973-05-11 BE BE131029A patent/BE799431A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH570412A5 (US08063081-20111122-C00044.png) | 1975-12-15 |
| IL42055A (en) | 1975-06-25 |
| DE2223239B2 (de) | 1980-04-24 |
| DE2223239A1 (de) | 1973-11-22 |
| IL42055A0 (en) | 1973-06-29 |
| GB1422362A (en) | 1976-01-28 |
| BE799431A (fr) | 1973-11-12 |
| FR2184748A1 (US08063081-20111122-C00044.png) | 1973-12-28 |
| JPS4924920A (US08063081-20111122-C00044.png) | 1974-03-05 |
| NL180834B (nl) | 1986-12-01 |
| JPS5550958B2 (US08063081-20111122-C00044.png) | 1980-12-20 |
| NL180834C (nl) | 1987-05-04 |
| FR2184748B1 (US08063081-20111122-C00044.png) | 1978-04-21 |
| ZA733099B (en) | 1974-05-29 |
| NL7306543A (US08063081-20111122-C00044.png) | 1973-11-14 |
| US3833645A (en) | 1974-09-03 |
| SU475782A3 (ru) | 1975-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete renunciation |