GB1021820A - Dicarbamoyl phosphines and phosphine oxides - Google Patents
Dicarbamoyl phosphines and phosphine oxidesInfo
- Publication number
- GB1021820A GB1021820A GB5165464A GB5165464A GB1021820A GB 1021820 A GB1021820 A GB 1021820A GB 5165464 A GB5165464 A GB 5165464A GB 5165464 A GB5165464 A GB 5165464A GB 1021820 A GB1021820 A GB 1021820A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- unsubstituted
- acid
- phosphine
- formula
- 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
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 title abstract 2
- GGVVWWSXSOLNDT-UHFFFAOYSA-N carbamoylphosphanylformamide Chemical class NC(=O)PC(N)=O GGVVWWSXSOLNDT-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 1
- 101100305864 Alteromonas mediterranea (strain DSM 17117 / CIP 110805 / LMG 28347 / Deep ecotype) rph2 gene Proteins 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 101100135363 Yarrowia lipolytica (strain CLIB 122 / E 150) RIM101 gene Proteins 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000007654 immersion Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/50—Organo-phosphines
- C07F9/5036—Phosphines containing the structure -C(=X)-P or NC-P
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives 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)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Fireproofing Substances (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1021820/C2/1> wherein R is a substituted or unsubstituted branched or straight chain alkyl radical containing from 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl radical or a substituted or unsubstituted aryl radical and n is 0 or 1. They are prepared by reacting, under substantially anaerobic conditions, a secondary phosphine of the formula RPH2 with isocyanic acid, and if desired, the product so obtained is oxidized to form the corresponding tertiary phosphine oxide. The isocyanic acid reactant may be introduced into the reaction mixture or it may be generated in situ by mixing an alkali metal derivative of isocyanic acid such as NaNCo or KNCO with the phosphine reactant in the presence of an acid. Suitable acids are mineral acids such as HCl, HBr and H2So4 and organic acids such as acetic acid and propionic acid. The reaction is preferably carried out in an aqueous medium at a temperature between - 10 DEG C. and 200 DEG C. Non-aqueous conditions using an inert organic solvent such as CH3CN, tetrahydrofuran, dioxane or the dimethyl ether of ethylene glycol may also be employed. The dicarbonoyl-substituted tertiary phosphines and phosphine oxides of the invention are useful as flameproofing agents (see Division D1).ALSO:Cotton cloth is flame-proofed by immersion in a solution containing 0.5% to 10% of a compound of the formula: <FORM:1021820/D1-D2/1> (see Division C2) wherein R is a substituted or unsubstituted, branched or straight chain alkyl radical containing from 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl radical or a substituted or unsubstituted aryl radical and n is 0 or 1, and the cloth subsequently dried.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5165464A GB1021820A (en) | 1964-12-18 | 1964-12-18 | Dicarbamoyl phosphines and phosphine oxides |
| FR2697A FR87278E (en) | 1964-12-18 | 1965-01-21 | Novel tertiary disubstituted carbamoylphosphines and their oxides and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5165464A GB1021820A (en) | 1964-12-18 | 1964-12-18 | Dicarbamoyl phosphines and phosphine oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1021820A true GB1021820A (en) | 1966-03-09 |
Family
ID=10460873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5165464A Expired GB1021820A (en) | 1964-12-18 | 1964-12-18 | Dicarbamoyl phosphines and phosphine oxides |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR87278E (en) |
| GB (1) | GB1021820A (en) |
-
1964
- 1964-12-18 GB GB5165464A patent/GB1021820A/en not_active Expired
-
1965
- 1965-01-21 FR FR2697A patent/FR87278E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR87278E (en) | 1966-07-08 |
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