Substituted cyclic phosphine oxides
AssigneeBayer Aktiengesellschaft
InventorsReinhard Schliebs, Hans-Dieter Block
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AssigneeBayer Aktiengesellschaft
InventorsReinhard Schliebs, Hans-Dieter Block
Estimating the term…
A cyclic phosphine oxide of the formula ##STR1## in which R.sup.1 is an alkyl or an aryl radical having up to 14 carbon atoms, R.sup.2, r.sup.3 and R.sup.4 each independently is a C.sub.1 -C.sub.4 -alkyl radical, hydrogen, chlorine or bromine, X and Y each independently is oxygen or sulfur, a, b, and c each independently is 0 or 1, and R.sup.5 is a C.sub.1 -C.sub.12 -alkyl radical and, where a = 0, also an aryl radical and, where a = 1, an equivalent of a cation, R.sup.6 is a C.sub.1 -C.sub.12 -alkyl radical and, where b = 0, also an aryl radical and, where b = 1, an equivalent of a cation, Is produced by reacting an unsaturated 5-membered cyclic phosphine oxide of the formula ##STR2## with a compound containing a phosphorus-hydrogen bond and of the formula ##STR3## in which R.sup.7 is a C.sub.1 -C.sub.12 -alkyl radical or, where a = 0, also an aryl radical, and R.sup.8 is a C.sub.1 -C.sub.12 -alkyl radical or, where b = 0, also an aryl radical, In the presence of free radicals at a temperature of about 50.degree. C to about 300.degree. C, and the reaction product is optionally hydrolyzed and converted into a salt.
A cyclic phosphine oxide of the formula ##STR12## in which R.sup.1 is an alkyl or an aryl radical having up to 14 carbon atoms,
Dependencies are inferred from the claim text.
No related US applications are recorded in the indexed filing history.
This invention relates to new substituted cyclic phosphine oxides corresponding to the general formula (I): ##STR4## in which R.sup.1 represents an alkyl or an aryl radical having up to 14 carbon atoms,
R.sup.2 r.sup.3 and R.sup.4 represent a C.sub.1 -C.sub.4 -alkyl radical, hydrogen, chlorine or bromine,
R.sup.5 represents a C.sub.1 -C.sub.12 -alkyl radical and, where a = 0, an aryl radical and, where a = 1, 1/n of an n-valent cation, such as a metal, ammonium, guanidinium, phosphonium or hydrogen,
The process according to the invention is illustrated by the following Examples:
A total of 117 g of an approximately 1:1-mixture of 1-methyl-1-oxophospholine-2 and 1-methyl-1-oxophospholine-3 is added dropwise with intensive stirring over a period of 1 hour at a temperature of 113.degree. to 115.degree. C to 550 g of dimethyl phosphite accommodated in a 1 liter glass flask. At the same time, a suspension of 8 g of dibenzoyl peroxide in silicone oil is added dropwise over the reaction time. All the materials used have been freed from traces of oxygen by repeated evacuation and venting with nitrogen.
On completion of the reaction, first the dimethyl phosphite and then the unreacted part of the 1-methyl-1-oxophospholine (81 g), which consists of substantially equal parts of the two isomers, are distilled off in vacuo. 28 g of an almost colorless oil (b.p. .sub.0.5 :185.degree. to 190.degree. C) distil over during distillation of the residue, thickening in the receiver into a white crystalline paste which becomes liquid again between 40.degree. and 55.degree. C.
Having phosphorus atoms as the only ring hetero atoms: the ring phosphorus atom being part of a phosphine oxide or thioxide
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen
Term ended 4 Oct 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
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