GB1356180A - Tertiary phosphine oxides and a process for their preparation - Google Patents
Tertiary phosphine oxides and a process for their preparationInfo
- Publication number
- GB1356180A GB1356180A GB3823171A GB3823171A GB1356180A GB 1356180 A GB1356180 A GB 1356180A GB 3823171 A GB3823171 A GB 3823171A GB 3823171 A GB3823171 A GB 3823171A GB 1356180 A GB1356180 A GB 1356180A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- radical
- alkyl
- group
- hydrogen atom
- 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 group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 18
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- 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
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1356180 Tertiary phosphine oxides FARBWERKE HOECHST AG 13 Aug 1971 [13 Aug 1970 30 Dec 1970 7 July 1971 (2)] 38231/71 Heading C2P The invention comprises tertiary phosphine oxides of the general formula wherein R and R<SP>1</SP> which may be the same or different, represent an alkyl or cycloalkyl group having up to 12 carbon atoms and R<SP>2</SP> represents a hydrogen atom, an alkyl radical having up to 4 carbon atoms or a cycloalkyl radical having from 4 to 8 carbon atoms, these radicals R<SP>2</SP> being unsubstituted or substituted by one or more hydroxyl groups, alkoxy groups of up to 4 carbon atoms or acyloxy groups of up to 4 carbon atoms, R<SP>3</SP> represents a hydrogen atom, an alkyl radical having up to 5 carbon atoms, hydroxyalkyl, alkoxyalkyl or acyloxyalkyl radical, the alkyl moieties of which have up to 4 carbon atoms, R<SP>4</SP> represents a hydrogen atom or an alkyl radical having up to 4 carbon atoms, a represents an integer of from zero to 4 and Z represents an alkyl radical having up to 4 carbon atoms or a cycloalkyl radical having from 4 to 8 carbon atoms, which radical is substituted by at least one OH or alkoxy, acyloxy or alkylmercapto group of up to 4 carbon atoms each, or wherein two of such substituents are combined together to form a ring, or Z is a group - OR<SP>5</SP> or -NR<SP>6</SP>R<SP>7</SP> in which R<SP>5</SP> is alkyl having up to 4 carbon atoms, an alkanoyl radical of up to 4 carbon atoms or a carbamoyl group and when a is other than zero R 5 may also represent a hydrogen atom, R 6 is H, an alkyl radical having up to 4 carbon atoms or an alkanoyl or carboalkoxy radical of up to 4 carbon atoms, R<SP>7</SP> is H or alkyl having up to 4 carbon atoms and R<SP>6</SP> and R<SP>7</SP> together with the N atom may stand for a 4- to 7-membered heterocyclic radical, with the proviso that when any one of the substituents on the P atom (as appropriate to its definition) is an alkyl or hydroxyalkyl group of more than nine carbon atoms neither of the other two substituents is an alkyl or hydroxyalkyl group having up to 3 carbon atoms. The compounds are obtained by reacting a secondary phosphine oxide of the general formula (R)(R<SP>1</SP>)P(O)H at 50-250‹ C. in the presence of a free radicalforming agent as catalyst and/or during exposure to ultra-violet light, with an olefinic compound of the formula Preferred free radical-forming agents are di-tbutyl peroxide and azobisisobutyronitrile and the reaction is suitably effected under an inert gas. The products are useful for flame-proofing flammable material and as corrosion inhibitors. They also have insecticidal and fungicidal properties and for this purpose they may be used in admixture with an inert carrier or diluent.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2040280A DE2040280C3 (en) | 1970-08-13 | 1970-08-13 | Tertiary phosphine oxides and processes for their preparation |
| DE2064574A DE2064574C3 (en) | 1970-12-30 | 1970-12-30 | Tertiary phosphine oxides and processes for their preparation |
| DE2133794A DE2133794A1 (en) | 1971-07-07 | 1971-07-07 | Tertiary phosphine oxides - from dialkylphosphine oxides and olefines |
| DE2133795A DE2133795A1 (en) | 1971-07-07 | 1971-07-07 | Tertiary phosphine oxides - as insecticides fungicides - flame retardants and corrosion inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1356180A true GB1356180A (en) | 1974-06-12 |
Family
ID=27431115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3823171A Expired GB1356180A (en) | 1970-08-13 | 1971-08-13 | Tertiary phosphine oxides and a process for their preparation |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA944349A (en) |
| FR (1) | FR2104344A5 (en) |
| GB (1) | GB1356180A (en) |
| IT (1) | IT945930B (en) |
| NL (1) | NL7110875A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8005204A (en) * | 1980-09-17 | 1982-04-16 | Gist Brocades Nv | ETHENYL-IMIDAZOLE DERIVATIVES WITH ANTIMYCOTIC EFFICACY. |
-
1971
- 1971-08-06 NL NL7110875A patent/NL7110875A/xx not_active Application Discontinuation
- 1971-08-11 IT IT27445/71A patent/IT945930B/en active
- 1971-08-12 CA CA120,375A patent/CA944349A/en not_active Expired
- 1971-08-13 FR FR7129708A patent/FR2104344A5/fr not_active Expired
- 1971-08-13 GB GB3823171A patent/GB1356180A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7110875A (en) | 1972-02-15 |
| IT945930B (en) | 1973-05-10 |
| FR2104344A5 (en) | 1972-04-14 |
| CA944349A (en) | 1974-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |