← Back to Patent Explorer
US4327040A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of phosphoric acid propargyl esters

Assignee: Bayer AG
•
Filing: 1980-06-09
•
Granted: 1982-04-27
•
Expires: 2000-06-09
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract A process for the preparation of a phosphoric acid propargyl ester of the formula ##STR1## wherein R 1 and R 2 each independently is an aryl radical or a C 1-4 -alkyl, C 1-4 -alkenyl or C 1-4 -alkynyl radical, and X, Y and Z each independently is oxygen or sulphur, comprising reacting a phosphoric acid monoester chloride or diester chloride with at least the equivalent amount of propargyl alcohol in a two-phase system in the presence of an inorganic base as an acid-trapping agent, and a catalyst comprising about 0.001 to 100 mol %, relative to the phosphoric acid ester chloride, of a tertiary amine or quaternary ammonium or phosphonium salt with at least 9 C atoms. Advantageously the catalyst is present in about 0.01 to 10 mol % relative to the phosphoric acid ester chloride and is a tertiary amine or quaternary ammonium salt, X, Y and Z are oxygen, R 1 is propargyl and R 2 is C 1-4 -alkyl, the reaction is effected in the presence of methylene chloride, chloroform or toluene as solvent, the base is used in at least the equivalent amount and is selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates and alkaline earth metal carbonates.

Inventors

  • 👤 Gunter Arend
  • 👤 Peter Feyen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 01:27
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/16; C07F9/165; C07F9/173; C07F9/08; C07F9/09; C07F9/113; C07F9/14; C07F9/1403

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 124 words
A process for the preparation of a phosphoric acid propargyl ester of the formula ##STR12## wherein R 1 and R 2 each independently is an aryl radical or a C 1-4 -alkyl, C 1-4 -alkenyl or C 1-4 -alkynyl radical, and X, Y and Z each independently is oxygen or sulphur, comprising reacting a phosphoric acid monoester chloride or diester chloride with at least the equivalent amount of propargyl alcohol in a two-phase water-organic solvent system in the presence of an aqueous solution of an inorganic base as an acid-trapping agent, and a catalyst comprising about 0.001 to 100 mol %, relative to the phosphoric acid ester chloride, of a tertiary amine or quaternary ammonium or phosphonium salt with at least 9 C atoms.
Claim 2
Dependent Claim 124 words
A process for the preparation of a phosphoric acid propargyl ester of the formula ##STR12## wherein R 1 and R 2 each independently is an aryl radical or a C 1-4 -alkyl, C 1-4 -alkenyl or C 1-4 -alkynyl radical, and X, Y and Z each independently is oxygen or sulphur, comprising reacting a phosphoric acid monoester chloride or diester chloride with at least the equivalent amount of propargyl alcohol in a two-phase water-organic solvent system in the presence of an aqueous solution of an inorganic base as an acid-trapping agent, and a catalyst comprising about 0.001 to 100 mol %, relative to the phosphoric acid ester chloride, of a tertiary amine or quaternary ammonium or phosphonium salt with at least 9 C atoms.
Claim 3
Dependent Claim 25 words
A process according to claim 1, wherein the catalyst is present in about 0.01 to 10 mol % relative to the phosphoric acid ester chloride.
Claim 4
Dependent Claim 13 words
A process according to claim 2, wherein the catalyst is a tertiary amine.
Claim 5
Dependent Claim 45 words
A process according to claim 2, wherein the catalyst is a quaternary ammonium salt with at least 9 C atoms in the cationic part of the molecule and it is present in about 0.01 to 1 mol % relative to the phosphoric acid ester chloride.
Claim 6
Dependent Claim 13 words
A process according to claim 1, wherein X, Y and Z are oxygen.
Claim 7
Dependent Claim 18 words
A process according to claim 1, wherein R 1 is propargyl and R 2 is C 1-4 -alkyl.
Claim 8
Dependent Claim 36 words
A process according to claim 1, wherein the reaction is effected in the presence of an inert substantially water-immiscible organic solvent selected from the group consisting of hydrocarbons, halogenated hydrocarbons, nitro-substituted hydrocarbons, ethers, ketones and esters.
Claim 9
Dependent Claim 15 words
A process according to claim 7, wherein the solvent comprises methylene chloride, chloroform or toluene.
Claim 10
Dependent Claim 31 words
A process according to claim 1, wherein the base is selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates and alkaline earth metal carbonates.
Claim 11
Dependent Claim 17 words
A process according to claim 1, wherein the base is used in at least the equivalent amount.
Claim 12
Dependent Claim 18 words
A process according to claim 1, wherein the reaction is effected at about -10° C. to +80° C.
Claim 13
Dependent Claim 17 words
A process according to claim 11, wherein the reaction is effected at about 0° to 40° C.
Claim 14
Dependent Claim 87 words
A process according to claim 9, wherein the catalyst is present in about 0.01 to 10 mol % relative to the phosphoric acid ester chloride and is a tertiary amine or quaternary ammonium salt, X, Y and Z are oxygen, R 1 is propargyl and R 2 is C 1-4 -alkyl, the reaction is effected in the presence of methylene chloride, chloroform or toluene as solvent, the base is used in at least the equivalent amount and the reaction is effected at about 0° to 40° C.

References Cited (Backward Citations)

US2471464A Cited
US2865801A Cited
US3005001A Cited
US3087957A Cited
US3189636A Cited
US3336422A Cited
US3972887A Cited
US4007197A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-04-26 1985-10-26 1986-04-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-04-26 1989-10-26 1990-04-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-04-26 1993-10-26 1994-04-27 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag