GB1215157A - New phosphetane-1-oxide compounds, their manufacture and use - Google Patents
New phosphetane-1-oxide compounds, their manufacture and useInfo
- Publication number
- GB1215157A GB1215157A GB3439467A GB3439467A GB1215157A GB 1215157 A GB1215157 A GB 1215157A GB 3439467 A GB3439467 A GB 3439467A GB 3439467 A GB3439467 A GB 3439467A GB 1215157 A GB1215157 A GB 1215157A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- phosphetane
- isocyanate
- formula
- phenyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000012948 isocyanate Substances 0.000 abstract 3
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000001718 carbodiimides Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 abstract 1
- XUNRSVNAHRPKRH-UHFFFAOYSA-N 2,2,3,4,4-pentamethyl-1-phenyl-1$l^{5}-phosphetane 1-oxide Chemical compound CC1(C)C(C)C(C)(C)P1(=O)C1=CC=CC=C1 XUNRSVNAHRPKRH-UHFFFAOYSA-N 0.000 abstract 1
- XMRNRYZTDXDPDU-UHFFFAOYSA-N 2,2,3-trimethyl-1-phenyl-1$l^{5}-phosphetane 1-oxide Chemical compound CC1(C)C(C)CP1(=O)C1=CC=CC=C1 XMRNRYZTDXDPDU-UHFFFAOYSA-N 0.000 abstract 1
- HJHZRZFONUPQAA-UHFFFAOYSA-N 2-isocyanato-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C(C)=C1 HJHZRZFONUPQAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 abstract 1
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical compound ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 isocyanate compounds Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000126 substance Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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)
- Catalysts (AREA)
Abstract
1,215,157. Phosphetane-1-oxides. IMPERIAL CHEMICAL INDUSTRIES Ltd. 5 July, 1968 [26 July, 1967], No. 34394/67. Heading C2C. Novel phosphetane-1-oxide compounds of the general formula wherein R is a hydrocarbon radical and each of R 1 and R 2 is a hydrogen atom or a methyl group, are prepared either by reacting together an olefine of the formula and a dichlorophosphine of the formula RPCl 2 in the presence of a Friedel-Crafts catalyst, e.g. aluminium chloride, and then adding water to hydrolyse the resultant complex, or, if in the final product both R 1 and R 2 represent methyl groups, also by treating 2,2,3,4,4 - pentamethyltrimethylene phosphinic acid chloride with a Grignard reagent of the formula RMgBr, heating to effect reaction and then treating with water. The products can be used as catalysts for the conversion of isocyanate compounds into carbodiimides in accordance with the general reaction wherein X is an organic radical. Examples describe the preparation of 1-phenyl and 1-nbutyl - 2,2,3,4,4 - pentamethylphosphetane - 1- oxide and 1-phenyl-2,2,3-trimethylphosphetane- 1-oxide. Examples also describe the conversion to the corresponding carbodiimide of naphthyl- 1 - isocyanate, m - chlorophenylisocyanate and 2,4,6 - trimethylphenylisocyanate using 1 - nbutyl - 2,2,3,4,4 - pentamethyl phosphetane oxide as catalyst, and also of naphthyl-1-isocyanate, cyclohexyl isocyanate, m-chlorophenylisocyanate and p - methoxyphenylisocyanate using 1 - phenyl - 2,2,3,4,4 - pentamethylphosphetane-1-oxide as catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3439467A GB1215157A (en) | 1967-07-26 | 1967-07-26 | New phosphetane-1-oxide compounds, their manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3439467A GB1215157A (en) | 1967-07-26 | 1967-07-26 | New phosphetane-1-oxide compounds, their manufacture and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1215157A true GB1215157A (en) | 1970-12-09 |
Family
ID=10365113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3439467A Expired GB1215157A (en) | 1967-07-26 | 1967-07-26 | New phosphetane-1-oxide compounds, their manufacture and use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1215157A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147710A (en) | 1973-08-21 | 1979-04-03 | Bayer Aktiengesellschaft | Compounds containing phosphorous and a method for making polycarbodiimide foams with the compounds as a catalyst |
| EP3868803A1 (en) * | 2020-02-18 | 2021-08-25 | Covestro Deutschland AG | Method for carbodiimide formation |
-
1967
- 1967-07-26 GB GB3439467A patent/GB1215157A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147710A (en) | 1973-08-21 | 1979-04-03 | Bayer Aktiengesellschaft | Compounds containing phosphorous and a method for making polycarbodiimide foams with the compounds as a catalyst |
| EP3868803A1 (en) * | 2020-02-18 | 2021-08-25 | Covestro Deutschland AG | Method for carbodiimide formation |
| WO2021165126A1 (en) * | 2020-02-18 | 2021-08-26 | Covestro Deutschland Ag | Process for carbodiimidization |
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