DE865742C - Verfahren zur Herstellung von organischen Phosphorverbindungen - Google Patents
Verfahren zur Herstellung von organischen PhosphorverbindungenInfo
- Publication number
- DE865742C DE865742C DEP2967A DE0002967A DE865742C DE 865742 C DE865742 C DE 865742C DE P2967 A DEP2967 A DE P2967A DE 0002967 A DE0002967 A DE 0002967A DE 865742 C DE865742 C DE 865742C
- Authority
- DE
- Germany
- Prior art keywords
- compound
- pyridine
- potassium
- basicity
- reacted
- 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 13
- 150000002903 organophosphorus compounds Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 8
- 239000011698 potassium fluoride Substances 0.000 description 8
- 235000003270 potassium fluoride Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PGJBQBDNXAZHBP-UHFFFAOYSA-N Dimefox Chemical compound CN(C)P(F)(=O)N(C)C PGJBQBDNXAZHBP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NHEULQMXMXIOJY-UHFFFAOYSA-N Cl[PH2]=O Chemical compound Cl[PH2]=O NHEULQMXMXIOJY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- XDGQKYBDSAFVEH-UHFFFAOYSA-N N-[dimethylamino(fluoro)phosphoryl]-N-ethylcyclohexanamine Chemical compound CN(C)P(F)(N(C1CCCCC1)CC)=O XDGQKYBDSAFVEH-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- -1 amine hydrochloride Chemical class 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- MWVMKRRNRAEZOI-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCN(C)CCCC MWVMKRRNRAEZOI-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1195350A GB688760A (en) | 1950-05-12 | 1950-05-12 | Improvements in or relating to organic phosphorus-containing compounds |
| GB29782/50A GB688787A (en) | 1950-05-12 | 1950-12-05 | Improvements in or relating to phosphorus-containing organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE865742C true DE865742C (de) | 1953-02-05 |
Family
ID=32299771
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP2967A Expired DE865742C (de) | 1950-05-12 | 1950-08-10 | Verfahren zur Herstellung von organischen Phosphorverbindungen |
| DEP5506A Expired DE972208C (de) | 1950-05-12 | 1951-05-06 | Verfahren zur Herstellung von Bis-isopropylamino-fluor-phosphinoxyd |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP5506A Expired DE972208C (de) | 1950-05-12 | 1951-05-06 | Verfahren zur Herstellung von Bis-isopropylamino-fluor-phosphinoxyd |
Country Status (8)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853515A (en) * | 1951-08-09 | 1958-09-23 | Coates Harold | Production of alkyl phosphonyl fluorides |
| US2882303A (en) * | 1953-05-05 | 1959-04-14 | Kellogg M W Co | Process for producing organophosphorus compounds |
| US3155659A (en) * | 1959-02-16 | 1964-11-03 | Stauffer Chemical Co | Phosphonic diamides and methods of making same |
| US4105759A (en) * | 1977-03-28 | 1978-08-08 | Colgate-Palmolive Company | Amine monofluorophosphates in dentifrices |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2146356A (en) * | 1935-07-02 | 1939-02-07 | Winthrop Chem Co Inc | Dialkylaminophosphorous fluorides and a process for preparing the same |
| GB602446A (en) * | 1944-04-17 | 1948-05-27 | Hamilton Mccombie | A process for the production of fluorophosphonic acid compounds |
| US2502966A (en) * | 1948-05-22 | 1950-04-04 | Monsanto Chemicals | Alkyl substituted amido pyrophosphates |
-
0
- BE BE503072D patent/BE503072A/xx unknown
- NL NL77260D patent/NL77260C/xx active
- LU LU30725D patent/LU30725A1/xx unknown
- NL NL75557D patent/NL75557C/xx active
- BE BE497548D patent/BE497548A/xx unknown
-
1950
- 1950-08-08 FR FR1026806D patent/FR1026806A/fr not_active Expired
- 1950-08-10 DE DEP2967A patent/DE865742C/de not_active Expired
- 1950-12-05 GB GB29782/50A patent/GB688787A/en not_active Expired
-
1951
- 1951-05-06 DE DEP5506A patent/DE972208C/de not_active Expired
- 1951-05-08 FR FR1036548D patent/FR1036548A/fr not_active Expired
- 1951-05-08 US US225264A patent/US2678334A/en not_active Expired - Lifetime
-
1953
- 1953-12-30 MY MY116/53A patent/MY5300116A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE972208C (de) | 1959-06-04 |
| NL77260C (US06605200-20030812-C00035.png) | |
| FR1036548A (fr) | 1953-09-08 |
| US2678334A (en) | 1954-05-11 |
| BE503072A (US06605200-20030812-C00035.png) | |
| BE497548A (US06605200-20030812-C00035.png) | |
| LU30725A1 (US06605200-20030812-C00035.png) | |
| GB688787A (en) | 1953-03-11 |
| MY5300116A (en) | 1953-12-31 |
| NL75557C (US06605200-20030812-C00035.png) | |
| FR1026806A (fr) | 1953-05-05 |
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