US3980738A
Expired / Lapsed
US
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Process for the preparation of (thio)phosphoric (phosphonic) acid esters
Assignee: Bayer AG
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Filing: 1975-03-12
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Granted: 1976-09-14
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Expires: 1995-03-12
Abstract
Abstract A process for the preparation of a (thio)phosphoric(phosphonic) acid ester of the formula ##EQU1## in which R 1 is a straight-chain or branched alkyl, alkylmercapto or alkoxy group with up to 8 carbon atoms, R 2 is alkyl with 1 to 8 carbon atoms optionally substituted by chlorine, R 3 , r 4 , r 5 and R 6 each independently is hydrogen or some other radical, X, y and Z each independently is oxygen or sulfur, and Hal is chlorine or bromine, Which comprises reacting an olefin of the formula ##EQU2## in a one-step process with a halogenating agent and a (thio)phosphoric(phosphonic) acid ester of the formula ##EQU3##
Inventors
- 👤 Dieter Arlt
- 👤 Kurt Ley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 18:40
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/49; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/16; C07F9/165; C07F9/1651; C07F9/28; C07F9/38; C07F9/40; C07F9/4071; C07F9/4075
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
259 words
A process for the preparation of a (thio)-phosphoric (phosphonic) acid ester of the formula ##EQU4## in which R 1 is a straight-chain or branched alkyl, alkylmercapto or alkoxy group with up to 8 carbon atoms, R 2 is alkyl with 1 to 8 carbon atoms optionally substituted by chlorine, R 4 and R 6 each individually is hydrogen, C 1 -C 4 -alkyl or halogen. X, y and Z each individually is oxygen or sulfur, Hal is chlorine or bromine, and R 3 and R 5 each individually is hydrogen; halogen; a C 1 -C 18 -alkyl, acyloxy or C 2 -C 12 -alkenyl radical which can be substituted by halogen, an acyloxy or alkoxy group with up to 18 carbon atoms, isocyano, dichloroisocyano, chlorocarbonyl, cyano, chlorosulfonyl, a carbalkoxy group with up to 8 carbon atoms in the alkoxy moiety, or an optionally substituted carbamino group with up to 12 carbon atoms; phenyl; halogen-substituted phenyl; or C 1 -C 4 -alkyl-substituted phenyl; or R 3 and R 5 together form a 4- to 12-membered aliphatic or heterocyclic ring, or R 5 may alternatively be chlorocarbonyl; cyano; a carbalkoxy or an optionally substituted carbamino group with up to 9 carbon atoms; an alkylcarbonyl, alkylsulfonyl, arylcarbonyl or arylsulfonyl group, each with up to 7 carbon atoms; or an aldehyde group, which comprises reacting at a temperature of about -50°C to 120°C an olefin of the formula ##EQU5## in a one-step process with a halogenating agent and at least an equivalent amount of a (thio)phosphoric (phosphonic) acid ester of the formula ##EQU6##
Claim 2
Dependent Claim
259 words
A process for the preparation of a (thio)-phosphoric (phosphonic) acid ester of the formula ##EQU4## in which R 1 is a straight-chain or branched alkyl, alkylmercapto or alkoxy group with up to 8 carbon atoms, R 2 is alkyl with 1 to 8 carbon atoms optionally substituted by chlorine, R 4 and R 6 each individually is hydrogen, C 1 -C 4 -alkyl or halogen. X, y and Z each individually is oxygen or sulfur, Hal is chlorine or bromine, and R 3 and R 5 each individually is hydrogen; halogen; a C 1 -C 18 -alkyl, acyloxy or C 2 -C 12 -alkenyl radical which can be substituted by halogen, an acyloxy or alkoxy group with up to 18 carbon atoms, isocyano, dichloroisocyano, chlorocarbonyl, cyano, chlorosulfonyl, a carbalkoxy group with up to 8 carbon atoms in the alkoxy moiety, or an optionally substituted carbamino group with up to 12 carbon atoms; phenyl; halogen-substituted phenyl; or C 1 -C 4 -alkyl-substituted phenyl; or R 3 and R 5 together form a 4- to 12-membered aliphatic or heterocyclic ring, or R 5 may alternatively be chlorocarbonyl; cyano; a carbalkoxy or an optionally substituted carbamino group with up to 9 carbon atoms; an alkylcarbonyl, alkylsulfonyl, arylcarbonyl or arylsulfonyl group, each with up to 7 carbon atoms; or an aldehyde group, which comprises reacting at a temperature of about -50°C to 120°C an olefin of the formula ##EQU5## in a one-step process with a halogenating agent and at least an equivalent amount of a (thio)phosphoric (phosphonic) acid ester of the formula ##EQU6##
Claim 3
Dependent Claim
33 words
A process according to claim 1, in which R 1 is alkyl or alkoxy with 1 to 6 carbon atoms, and R 2 is optionally chlorine-substituted alkyl with 1 to 6 carbon atoms.
Claim 4
Dependent Claim
22 words
A process according to claim 2, in which R 1 is methyl, methoxy, or ethoxy and R 2 is methyl or ethyl.
Claim 5
Dependent Claim
65 words
A process according to claim 1, in which R 3 and R 5 each individually is hydrogen; fluorine, chlorine; bromine; or acyloxy with up to 5 carbon atoms, or alkyl or alkenyl with 1 to 6 carbon atoms optionally substituted by chlorine, bromine, isocyano, dichloroisocyano, chlorocarbonyl, cyano, chlorosulfonyl, a carbalkoxy, acyloxy or alkoxy group containing up to 5 carbon atoms, or an alkylated carbamino group.
Claim 6
Dependent Claim
19 words
A process according to claim 1, in which the radicals R 3 and R 4 are fluorine or chlorine.
Claim 7
Dependent Claim
51 words
A process according to claim 1, in which R 3 and R 5 together form a 5-membered or 6-membered ring which contains oxygen, a carbonyl group or a sulfone group, in addition to carbon atoms, as ring members and R 4 and R 6 each independently is hydrogen, chlorine or methyl.
Claim 8
Dependent Claim
35 words
A process according to claim 2, in which R 3 and R 5 each independently is carbalkoxy with up to 5 carbon atoms and R 4 and R 6 each independently is hydrogen or chlorine.
Claim 9
Dependent Claim
20 words
A process according to claim 1, in which the starting material of the formula (III) is an O,O,O-trialkylphosphoric acid ester.
Claim 10
Dependent Claim
20 words
A process according to claim 1, in which the starting material of the formula (III) is an O,O,O-trialkylthionophosphoric acid ester.
Claim 11
Dependent Claim
18 words
A process according to claim 1, in which the reaction is carried out at about -10°C to 50°C.
Claim 12
Dependent Claim
20 words
A process according to claim 1, in which the reaction is effected in the presence of a solvent or diluent.
Claim 13
Dependent Claim
23 words
A process according to claim 11 in which an excess of the (thio)phosphoric(phosphonic) acid ester (III) is used as the solvent or diluent.
Claim 14
Dependent Claim
19 words
A process according to claim 1, in which the halogenating agent is elementary chlorine or bromine, or sulfuryl chloride.
Claim 15
Dependent Claim
27 words
A process according to claim 1, in which between 1 and 5 moles of (thio)phosphoric(phosphonic) acid ester (III) are used per mole of the olefinic reactant (II).
Claim 16
Dependent Claim
17 words
A process according to claim 1, in which a Friedel-Crafts catalyst is added to the reaction mixture.
Claim 17
Dependent Claim
19 words
A process according to claim 15, in which the Friedel-Crafts catalyst is iron(III) chloride, zinc chloride or aluminum chloride.
Claim 18
Dependent Claim
91 words
A process according to claim 4, in which R 1 is methyl, methoxy, or ethoxy and R 2 is methyl or ethyl, the reaction is effected at a temperature of about -10° to 50°C in the presence of a solvent or diluent, between 1 and 5 moles of (thio)phosphoric(phosphonic) acid ester (III) are used per mole of the olefinic reactant (II), the halogenating agent is elementary chlorine or bromine or sulfuryl chloride, and at least one of iron (III) chloride, zinc chloride and aluminum chloride is added to the reaction mixture.
References Cited (Backward Citations)
US3691275A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-14 | 1980-03-15 | 1980-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-14 | 1984-03-15 | 1984-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-14 | 1988-03-15 | 1988-09-14 | $7700.00 | Window Closed / Lapsed |