DE1173469B - Verfahren zur Herstellung von Phosphor-isocyaniddichloriden bzw. -bromiden - Google Patents
Verfahren zur Herstellung von Phosphor-isocyaniddichloriden bzw. -bromidenInfo
- Publication number
- DE1173469B DE1173469B DEF38640A DEF0038640A DE1173469B DE 1173469 B DE1173469 B DE 1173469B DE F38640 A DEF38640 A DE F38640A DE F0038640 A DEF0038640 A DE F0038640A DE 1173469 B DE1173469 B DE 1173469B
- Authority
- DE
- Germany
- Prior art keywords
- bromides
- phosphorus
- isocyanide
- chlorine
- carbon tetrachloride
- 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
- -1 phosphorus isocyanide dichlorides Chemical class 0.000 title claims description 10
- 150000001649 bromium compounds Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000008164 mustard oil Substances 0.000 claims description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- QXZFLJVUSSWAFT-UHFFFAOYSA-N isocyano-dimethoxy-sulfanylidene-lambda5-phosphane Chemical compound COP(=S)(OC)[N+]#[C-] QXZFLJVUSSWAFT-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910010165 TiCu Inorganic materials 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MVSPLISYISOQCN-UHFFFAOYSA-N 1-[ethoxy(isocyano)phosphoryl]oxyethane Chemical compound CCOP(=O)([N+]#[C-])OCC MVSPLISYISOQCN-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 1
- GHCUTEQEZBWUGS-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C(=C(C=CC=1)OCCC)OCCC Chemical group O(C1=CC=CC=C1)C=1C(=C(C=CC=1)OCCC)OCCC GHCUTEQEZBWUGS-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HXKKQDLJUNWJLZ-UHFFFAOYSA-N dichlorophosphorylazaniumylidynemethane Chemical class P(=O)([N+]#[C-])(Cl)Cl HXKKQDLJUNWJLZ-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- LXUMNUAVISZZPN-UHFFFAOYSA-N triisocyanatophosphane Chemical class O=C=NP(N=C=O)N=C=O LXUMNUAVISZZPN-UHFFFAOYSA-N 0.000 description 1
- SYVVLAYMPOPKJS-UHFFFAOYSA-N triisothiocyanatophosphane Chemical class S=C=NP(N=C=S)N=C=S SYVVLAYMPOPKJS-UHFFFAOYSA-N 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- 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
- C07F9/24—Esteramides
-
- 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
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- 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)]
- C07F9/44—Amides thereof
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 (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38640A DE1173469B (de) | 1962-12-22 | 1962-12-22 | Verfahren zur Herstellung von Phosphor-isocyaniddichloriden bzw. -bromiden |
| CH1401463A CH426774A (de) | 1962-12-22 | 1963-11-15 | Verfahren zur Herstellung stickstoffhaltiger Phosphorverbindungen |
| US325456A US3328495A (en) | 1962-12-22 | 1963-11-21 | Phosphorus isocyanide dichloride compounds |
| GB47734/63A GB1002235A (en) | 1962-12-22 | 1963-12-03 | Phosphorus isocyanide dihalide compounds |
| NL63302211A NL141201B (nl) | 1962-12-22 | 1963-12-19 | Werkwijze voor de bereiding van isocyaandihalogeenverbindingen. |
| BE641531A BE641531A (ref) | 1962-12-22 | 1963-12-19 | |
| FR957878A FR1378501A (fr) | 1962-12-22 | 1963-12-20 | Dichlorures de phosphoro-isonitriles, et procédé pour les fabriquer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38640A DE1173469B (de) | 1962-12-22 | 1962-12-22 | Verfahren zur Herstellung von Phosphor-isocyaniddichloriden bzw. -bromiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1173469B true DE1173469B (de) | 1964-07-09 |
Family
ID=7097434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF38640A Pending DE1173469B (de) | 1962-12-22 | 1962-12-22 | Verfahren zur Herstellung von Phosphor-isocyaniddichloriden bzw. -bromiden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3328495A (ref) |
| BE (1) | BE641531A (ref) |
| CH (1) | CH426774A (ref) |
| DE (1) | DE1173469B (ref) |
| FR (1) | FR1378501A (ref) |
| GB (1) | GB1002235A (ref) |
| NL (1) | NL141201B (ref) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3911057A (en) * | 1974-07-01 | 1975-10-07 | Velsicol Chemical Corp | N-benzylthiomethylenephosphonamidates and phosphoramidates |
| US3961050A (en) * | 1974-07-01 | 1976-06-01 | Velsicol Chemical Corporation | Insecticidal compositions and methods of killing insects using benzylthiomethylenephosphonamidates and phosphoramidates |
| FR2407978A1 (fr) * | 1977-11-02 | 1979-06-01 | Orogil | Nouvelles compositions lubrifiantes contenant du phosphore et de l'azote |
| US4252660A (en) * | 1979-11-23 | 1981-02-24 | Mobil Oil Corporation | Reaction products of organophosphorus halides with inorganic thiocyanates as load-carrying additives in lubricating oil compositions |
| US5652207A (en) * | 1996-08-12 | 1997-07-29 | Lever Brothers Company, Division Of Conopco, Inc. | Phosphinoyl imines for use as oxygen transfer agents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1139494B (de) * | 1960-03-26 | 1962-11-15 | Bayer Ag | Verfahren zur Herstellung von phosphorhaltigen Thioharnstoffen |
-
1962
- 1962-12-22 DE DEF38640A patent/DE1173469B/de active Pending
-
1963
- 1963-11-15 CH CH1401463A patent/CH426774A/de unknown
- 1963-11-21 US US325456A patent/US3328495A/en not_active Expired - Lifetime
- 1963-12-03 GB GB47734/63A patent/GB1002235A/en not_active Expired
- 1963-12-19 BE BE641531A patent/BE641531A/fr unknown
- 1963-12-19 NL NL63302211A patent/NL141201B/nl unknown
- 1963-12-20 FR FR957878A patent/FR1378501A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1139494B (de) * | 1960-03-26 | 1962-11-15 | Bayer Ag | Verfahren zur Herstellung von phosphorhaltigen Thioharnstoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL141201B (nl) | 1974-02-15 |
| BE641531A (ref) | 1964-06-19 |
| US3328495A (en) | 1967-06-27 |
| FR1378501A (fr) | 1964-11-13 |
| GB1002235A (en) | 1965-08-25 |
| NL302211A (nl) | 1965-10-11 |
| CH426774A (de) | 1966-12-31 |
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