Claims
- 1. A method for preparing esters of polyhaloaromatic carboxylic acids and anhydrides of the formula: ##STR62## wherein: (a) the aromatic rings can have all possible isomeric arrangements;
- (b) A is Br or Cl;
- (c) m is 3, 4, or 5;
- (d) q is an integer of 1 to 6;
- (e) R.sup.7 is
- (i) a substituted or unsubstituted, C.sub.1-30 alkyl or an aryl having up to 30 carbon atoms, and with a valence (v) which is an integer of 1 to 4; ##STR63## where: R.sup.3 is H or a substituted or unsubstituted C.sub.1-30 alkyl, or an aryl having up to 30 carbon atoms,
- R.sup.4 is, independently, H or CH.sub.3,
- p is an integer of 1 to 50, and
- t is an integer of 1 to 49; or ##STR64## where R.sup.5 is a substituted or unsubstituted, C.sub.1-30 alkyl or an aryl having up to 30 carbon atoms; and ##EQU2## q, m, and v being as defined above; which comprises reacting: (I) at least one polyhaloaromatic carboxylic acid or anhydride of the formulae ##STR65## wherein A and m are as defined above and n is 3 or 4; with (II) at least a stoichiometric quantity of alcohol or polyol of the formula
- R.sup.7 (OH).sub.v
- wherein R.sup.7 and v are as defined above; and
- (III) a catalytically effective amount of Ti(OR.sup.2).sub.4, wherein R.sup.2, independently, is a substituted or unsubstituted C.sub.1-30 alkyl or a substituted or unsubstituted C.sub.2-22 alkylene, in the absence of an alkali or alkaline salt.
- 2. A method according to claim 1 wherein said catalyst is at least one of:
- titanium tetraisopropoxide;
- titanium tetrabutoxide;
- titanium tetra(2-ethyl-1-hexoxide); or
- titanium bis(ethyl acetoacetato)diisopropoxy.
- 3. A method according to claim 1 wherein said polyhaloaromatic carboxylic acid or anhydride is at least one of: ##STR66##
- 4. A method according to claim 1 wherein said alcohol or polyol is at least one of: ##STR67## (2) C.sub.12 H.sub.25 OH, (3) C.sub.18 H.sub.37 OH,
- (4) CH.sub.3 OCH.sub.2 CH.sub.2 OH,
- (5) i-C.sub.9 H.sub.19 OH,
- (6) CH.sub.3 O(CH.sub.2 CH.sub.2 O).sub.2 H,
- (7) C.sub.4 H.sub.9 OCH.sub.2 CH.sub.2 OH,
- (8) HO(CH.sub.2 CH.sub.2 O).sub.4 H,
- (9) i-C.sub.10 H.sub.21 OH,
- (10) HO(CH.sub.2 CH.sub.2 O).sub.6 H,
- (11) HO(CH.sub.2 CH.sub.2 O).sub.12 H, or
- (12) CH.sub.3 O(CH.sub.2 CH.sub.2 O).sub.7 H.
- 5. A method according to claim 1 wherein said polyhaloaromatic carboxylic acid or anhydride of reactant I is at least one of:
- tetrabromophthalic anhydride;
- tetrachlorophthalic anhydride;
- 2,3,5,6-tetraromoterephthalic acid;
- 2,4,5,6-tetrabromoisophthalic acid; or
- tribromophthalic anhydride.
- 6. A method according to claim 1 wherein said alcohol or polyol of reactant II is at least one of:
- 2-ethyl-1-hexanol;
- 1-dodecanol;
- 1-octanol;
- isononyl alcohol;
- 2-(2-methoxyethoxy)-ethanol;
- 2-(2-ethoxyethoxy)-ethanol;
- isodecyl alcohol;
- n-butanol;
- 1-octadecanol;
- cyclohexanol;
- 1,12-dodecandiol;
- 1-hexanol;
- 1-decanol; or
- 2-ethyl-1-butanol.
Parent Case Info
This application is a continuation-in-part of Ser. No. 244,421, filed Sep. 16, 1988, now U.S. Pat. No. 5,049,697, which is a continuation-in-part of Ser. No. 99,361, filed Sep. 21, 1987, now abandoned.
US Referenced Citations (14)
Foreign Referenced Citations (3)
Number |
Date |
Country |
47-47981 |
Dec 1972 |
JPX |
50-05701 |
Mar 1975 |
JPX |
810381 |
Mar 1959 |
GBX |
Non-Patent Literature Citations (5)
Entry |
Chemical Abstracts, vol. 70, No. 20: 88598e, (1969). |
Chemical Abstracts, vol. 90, No. 16: 122565s, (1979). |
Chemical Abstracts, vol. 104, No. 22: 187714s, (1986). |
Pape, et al., Journal of Cellular Plastics, Nov., 1968, pp. 438-442. |
Nordlander et al., Journal of the American Chemical Society, vol. 69, Nov. 1947, pp. 2679-2682. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
244421 |
Sep 1988 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
99361 |
Sep 1987 |
|