DE2418984A1 - Verfahren zur herstellung von fluorphosphorsaeuretetramethyldiamid - Google Patents
Verfahren zur herstellung von fluorphosphorsaeuretetramethyldiamidInfo
- Publication number
- DE2418984A1 DE2418984A1 DE19742418984 DE2418984A DE2418984A1 DE 2418984 A1 DE2418984 A1 DE 2418984A1 DE 19742418984 DE19742418984 DE 19742418984 DE 2418984 A DE2418984 A DE 2418984A DE 2418984 A1 DE2418984 A1 DE 2418984A1
- Authority
- DE
- Germany
- Prior art keywords
- dimefox
- tris
- reaction
- production
- dimethylamide
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 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 14
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 8
- RHFUXPCCELGMFC-UHFFFAOYSA-N n-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-phenylmethoxyacetamide Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(=O)C)OCC1=CC=CC=C1 RHFUXPCCELGMFC-UHFFFAOYSA-N 0.000 claims description 4
- PGJBQBDNXAZHBP-UHFFFAOYSA-N Dimefox Chemical compound CN(C)P(F)(=O)N(C)C PGJBQBDNXAZHBP-UHFFFAOYSA-N 0.000 description 24
- 239000007983 Tris buffer Substances 0.000 description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 4
- 229960004838 phosphoric acid Drugs 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- YNHXBEVSSILHPI-UHFFFAOYSA-N dimethylamidophosphoric dichloride Chemical compound CN(C)P(Cl)(Cl)=O YNHXBEVSSILHPI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- XFCFYXYRYOKBJS-UHFFFAOYSA-N [F-].[F-].[F-].[NH4+].[NH4+].[NH4+] Chemical compound [F-].[F-].[F-].[NH4+].[NH4+].[NH4+] XFCFYXYRYOKBJS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BVZPKXNHIPEDHB-UHFFFAOYSA-N azane;n-methylmethanamine Chemical compound N.CNC BVZPKXNHIPEDHB-UHFFFAOYSA-N 0.000 description 1
- SPUCQBCMTXYUBA-UHFFFAOYSA-N bis(dimethylamino)phosphinic acid hydrochloride Chemical compound Cl.CN(C)P(O)(=O)N(C)C SPUCQBCMTXYUBA-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742418984 DE2418984A1 (de) | 1974-04-19 | 1974-04-19 | Verfahren zur herstellung von fluorphosphorsaeuretetramethyldiamid |
| CS189275A CS181174B2 (en) | 1974-04-19 | 1975-03-20 | Method of preparing tetramethyldiamide of fluorophophoric acid |
| GB1407875A GB1462339A (en) | 1974-04-19 | 1975-04-07 | Manufacture of fluorophosphoric acid tetramethyldiamide |
| BE155487A BE828036A (fr) | 1974-04-19 | 1975-04-17 | Procede de preparation du fluorure tetramethyl-phosphorodiamique |
| FR7512299A FR2268021B1 (cs) | 1974-04-19 | 1975-04-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742418984 DE2418984A1 (de) | 1974-04-19 | 1974-04-19 | Verfahren zur herstellung von fluorphosphorsaeuretetramethyldiamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2418984A1 true DE2418984A1 (de) | 1975-10-30 |
Family
ID=5913374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742418984 Pending DE2418984A1 (de) | 1974-04-19 | 1974-04-19 | Verfahren zur herstellung von fluorphosphorsaeuretetramethyldiamid |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE828036A (cs) |
| CS (1) | CS181174B2 (cs) |
| DE (1) | DE2418984A1 (cs) |
| FR (1) | FR2268021B1 (cs) |
| GB (1) | GB1462339A (cs) |
-
1974
- 1974-04-19 DE DE19742418984 patent/DE2418984A1/de active Pending
-
1975
- 1975-03-20 CS CS189275A patent/CS181174B2/cs unknown
- 1975-04-07 GB GB1407875A patent/GB1462339A/en not_active Expired
- 1975-04-17 BE BE155487A patent/BE828036A/xx unknown
- 1975-04-21 FR FR7512299A patent/FR2268021B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2268021A1 (cs) | 1975-11-14 |
| CS181174B2 (en) | 1978-03-31 |
| GB1462339A (en) | 1977-01-26 |
| FR2268021B1 (cs) | 1977-04-15 |
| BE828036A (fr) | 1975-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |