Preparation of alkane phosphonic and phosphinic acid aryl esters

• US 4,377,537 A
• Filed: 01/02/1981
• Issued: 03/22/1983
• Est. Priority Date: 01/19/1980
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Block, Hans-Dieter, Frohlen, Hans-Gunther
• Primary Examiner(s): Sutto, Anton H.
• Application Number:
  US06/222,221
• Time in Patent Office: 809 Days
• Field of Search: 260/961, 260/969
• US Class Current: 558/122
• CPC Class Codes: C07F 9/3282 Esters with hydroxyaryl compounds
• CPC Class Codes: C07F 9/4084 Esters with hydroxyaryl compounds

Abstract

A process for the preparation of an alkane phosphonic acid diaryl ester or an alkane phosphinic acid aryl ester of the formula ##STR1## wherein R¹ is C₁ -C₂₀ alkyl or alkenyl group,

R² is a C₁ -C₂₀ alkyl or alkenyl group or a C₆ -C₁₀ aryl or aryloxy group,

R³ is C₆ -C₁₀ aryl group,

k is 0 or 1,

p is 1 or 2,

k+p=2,

plus an alkane phosphonic acid diaryl ester, alkane phosphinic acid aryl ester or phosphine oxide of the formula ##STR2## R⁴ and R⁵ each independently is C₁ -C₂₀ alkyl group, a C₆ -C₁₀ aryl group or a C₆ -C₁₀ aryloxy group,

R⁶ is C₁ -C₂₀ alkyl or alkenyl group,

n and m each is 0, 1 or 2, and

n+m=2,

comprising reacting an aryloxy compound of trivalent phosphorus of the formula ##STR3## (a) with an alkyl phosphite or alkyl phosphonite of the formula ##STR4## in the presence of an Arbusow catalyst, or (b) a rearrangement product formed in the presence of an Arbusow catalyst and of the formula ##STR5##

Claims

1. A process for the preparation of a phosphonic acid diaryl ester of the formula ##STR19## wherein R¹ is a C₁ -C₂₀ alkyl or alkenyl group, and

R³ is a C₆ -C₁₀ aryl group,

comprising reacting a triaryl phosphite of the formula ##STR20## with approximately half the molar amount of an alkyl phosphite of the formula ##STR21## in the presence of an Arbusow catalyst at a temperature from about 170°

to 300°

C.

2. A process for the preparation of a phosphinic acid aryl ester of the formula ##STR22## wherein R¹ is a C₁ -C₂₀ alkyl or alkenyl group,

R² is a C₁ -C₂₀ alkyl or alkenyl group or an aryl group, and

R³ is a C₆ -C₁₀ aryl group,

comprising reacting a phosphonous acid diaryl ester of the formula ##STR23## with approximately an equimolar amount of a phosphonous acid dialkyl ester of the formula ##STR24## in the presence of an Arbusow catalyst at a temperature from about 170°

to 300°

C.