GB1005154A - Carbamoyl phosphines and phosphine oxides and preparation thereof - Google Patents
Carbamoyl phosphines and phosphine oxides and preparation thereofInfo
- Publication number
- GB1005154A GB1005154A GB3380164A GB3380164A GB1005154A GB 1005154 A GB1005154 A GB 1005154A GB 3380164 A GB3380164 A GB 3380164A GB 3380164 A GB3380164 A GB 3380164A GB 1005154 A GB1005154 A GB 1005154A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- tertiary
- phosphine
- acid
- reaction
- 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 4
- QHUZHCCUWPRJEU-UHFFFAOYSA-N phosphanylformamide Chemical class NC(P)=O QHUZHCCUWPRJEU-UHFFFAOYSA-N 0.000 title 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 8
- -1 alkyl radical Chemical class 0.000 abstract 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000003003 phosphines Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 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
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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)
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)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises monocarbamoyl-substituted tertiary organic phosphines and phosphine oxides of the formula <FORM:1005154/C2/1> wherein R1 and R2 each represent a substituted or unsubstituted, branched or straight chain alkyl radical having from 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl radical, a substituted or unsubstituted aryl radical and n is 0 or 1. They may be prepared by reacting under substantially anaerobic conditions a secondary phosphine of the formula R1R2PH and isocyanic acid to give the tertiary phosphine (n=0) which if desired may be oxidized to the corresponding tertiary phosphine oxide (n=1). The anaerobic conditions may be set up by carrying the reaction out under nitrogen or a similar inert gas. Water is a preferred solvent but an inert organic solvent such as acetonitrile, tetrahydrofuran dioxane, and the dimethyl ether of ethylene glycol may be used. The isocyanic acid may be introduced as such into the reaction mixture or it may be generated is situ, e.g. an alkali metal derivative of isocyanic acid such as KNCO or KNCO may be admixed with the phosphine reactant in the presence of an acid, thus liberating the isocyanic acid. Suitable acids are HCl, HBr, H2SO4, acetic acid and propionic acid. A preferred range of reaction temperatures is between 22 DEG C. and 110 DEG C. The initially formed tertiary phosphine may be oxidized to the tertiary phosphine oxide by reaction with a peroxide such as hydrogen peroxide or dinitrogen tetroxide or with sulphuric acid. Alternatively, if the reaction is carried out in a vessel open to the air then only the tertiary phospine oxide is produced. The radicals R1 and R2 are described as being substituted by cyano, lower alkyl containing 1 to 6 carbon atoms, phenyl, halogen or lower alkoxy containing 1 to 6 carbon atoms substituents. Numerous examples are given of the tertiary phosphines and tertiary phosphine oxides and the products may be used as flameproofing agents (see Division D1). Specification 912,269 is referred to.ALSO:Compounds suitable for use as flame-proofing agents are monocarbamoyl-substituted tartiary organic phosphines and phosphine oxides of the formula <FORM:1005154/D1-D2/1> wherein R1 and R2 each represent a substituted or unsubstituted, branched or straight chain alkyl radical having from 1 to 18 carbon atoms, a substituted or unsubstituted aryl radical or a substituted or unsubstituted cycloalkyl radical and n is 0 or 1. (see Division C2). For example, cotton cloth may be immersed in a suitable solution containing from 0.5% to 10% of one of the above compounds, and the cloth subsequently dried. Specification 912,269 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US308083A US3214457A (en) | 1963-09-11 | 1963-09-11 | Carbamoyl phosphines and preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1005154A true GB1005154A (en) | 1965-09-22 |
Family
ID=23192472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3380164A Expired GB1005154A (en) | 1963-09-11 | 1964-08-19 | Carbamoyl phosphines and phosphine oxides and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1005154A (en) |
-
1964
- 1964-08-19 GB GB3380164A patent/GB1005154A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1029442A (en) | A process for the production of halogenated sulphones | |
| GB899842A (en) | Process for producing 1:3:4-thiadiazines having aromatic substituents | |
| GB1009302A (en) | Organic peroxides and a process for preparing them | |
| GB1005154A (en) | Carbamoyl phosphines and phosphine oxides and preparation thereof | |
| GB861472A (en) | N-arylmaleamic acids and the manufacture of ª‡:ª‰-di-(arylazolyl)-ethylene derivatives | |
| GB864438A (en) | A process for the preparation of organosiloxane esters | |
| GB977071A (en) | Hydroxylamine derivatives and process for making them | |
| GB1021820A (en) | Dicarbamoyl phosphines and phosphine oxides | |
| GB985984A (en) | A process for the manufacture of thiophosphoric esters | |
| GB1055184A (en) | A process for the manufacture of 2-styryl-oxazole compounds | |
| GB970670A (en) | Phosphorus-containing esters | |
| US3135779A (en) | Process for preparing ortho-aminophenol-beta-hydroxyethylsulfone sulfuric acid esters | |
| GB978550A (en) | Acylacetylaminobenzene compounds containing sulphonic acid groups and process for their manufacture | |
| GB1363758A (en) | Process for the production of 1,2,4-oxa-diazoles and novel 1,2,4- oxadiazoles | |
| US3159663A (en) | Process for preparing amino-substituted sulfate esters | |
| US3314993A (en) | Carbamoyl phosphines | |
| US3214457A (en) | Carbamoyl phosphines and preparation thereof | |
| US3415630A (en) | Boron-nitrogen compound | |
| ES393839A1 (en) | Process for the preparation of percarboxylic acids | |
| US2464004A (en) | Stable quinoline salt for electrolysis | |
| US2543341A (en) | Aroylacetamidine | |
| GB957827A (en) | New phosphorus-containing esters | |
| GB950897A (en) | New piperidine derivatives and processes for their manufacture | |
| GB808259A (en) | Thiophosphoric acid esters | |
| GB956221A (en) | Tertiary phosphines and methods of preparing same |