Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1986-06-03
1988-10-11
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 1, 560 72, 560 76, 560 83, 560 84, 560 85, 560 86, 560112, 560127, 560263, 558234, C07C 6976
Patent
active
047772824
DESCRIPTION:
BRIEF SUMMARY
This invention relates to the preparation of organic compounds and especially to the preparation of monomers for subsequent use in polymerisation reactions.
Known industrial methods for producing monomers, especially aromatic monomers wherein an aromatic group is bonded directly to a functional group such as an ester, thioester or carbonate, often have a number of disadvantages. For example high temperatures are usually required and/or unpleasant solvents such as pyridine are necessary. Aromatic ester monomers, for example can be prepared using a phase-transfer catalysis method, but this method has the disadvantage that two or more recrystallisations of the product are usually necessary in order to obtain a satisfactorily pure monomer.
In a paper by J Valade and M Pereyre entitled `Etude de la scission de la liaison Sn-O-C dans les monoalcoxytrialcoyetains`, Compt. Rend. 254, 3693(1962) there is described a method for making simple aliphatic esters by reacting methoxytributyltin with acetyl chloride or benzoyl chloride, the reaction producing methyl acetate or methyl benzoate. The use of tin in intermediates for making polymers is described in European Patent Publication No. 0,154,506.
In a first aspect the present invention provides a method for the preparation of an organic compound comprising reacting a first compound of the formula: element M used; the Periodic Table (IUPAC 1965 revision) or a transition metal, excluding carbon, silicon, nitrogen, phosphorus, boron, aluminium and titanium; nitrogen atom other than ##STR2## or a substituted phosphorus atom other than ##STR3## and A.sup.1 is an aromatic, aliphatic, aromatic/aliphatic, heterocyclic, alicyclic, siloxyl or silane group, ##STR4## where X is a halogen atom or a group capable of reacting with the first compound to eliminate a compound containing M and X; sulphur or zero if B is silicon; B is phosphorus, or from an aromatic group, aliphatic group or --OR' if B is silicon, where R' is a substituted or unsubstituted alkyl or aryl group; silicon; and alicyclic, siloxyl or silane group, formula: ##STR5## where G is either the group --M--(R).sub.r, or the group ##STR6##
Preferably the stoichiometric ratio of the first compound to the second compound is 1:2 to produce a compound, usually a monomer, of the formula: ##STR7## An example of this reaction is as follows: ##STR8##
In a second aspect the present invention provides a method for the preparation of an organic compound comprising reacting a first compound of the formula: element M used; the Periodic Table (IUPAC 1965 revision) or a transition metal, excluding carbon, silicon, nitrogen, phosphorus, boron, aluminium and titanium; atom other than ##STR9## or a substituted phosphorus atom other than ##STR10## and A.sup.1 is an aromatic, aliphatic, aromatic/aliphatic, heterocyclic, alicyclic, siloxyl or silane group, ##STR11## where X is a halogen atom or a group capable of reacting with the first compound to eliminate a compound containing M and X; sulphur or zero if B is silicon; B is phosphorus, or from an aromatic group, aliphatic group or --OR' if B is silicon, where R' is a substituted or unsubstituted alkyl or aryl group; silicon; alicyclic, siloxyl, or silane group; and formula: ##STR12## where Q is the either the group (R).sub.r M--, or the group ##STR13## and T is either the atom or group X, or the group --Y--A.sup.1 --Y--M--(R).sub.r.
The method according to this second aspect is especially useful when it is desired to produce a monomer having reactive end groups of the type (R).sub.r M-- or ##STR14## which can then be used directly in polymerisation reactions. An especially preferred monomer is one having acid chloride, ##STR15## end groups.
When carrying out the method according to the second aspect of the invention, the reaction conditions should be selected so as to prevent a polymerisation reaction between the first and second compounds. Therefore it is preferred to add a solution of the first compound gradually, for example dropwise, to a solution of the second compound. Also it is p
REFERENCES:
patent: 4129594 (1978-12-01), Baker et al.
Chemical Abstracts, vol. 77, No. 21, 20 Nov. 1972, see p. 407, col. 2, Abstract No. 139625r; and JP, B, 7227502, 22 Jul. 1972.
Chem. Abs. 77:139625r (Abstract of JP 72-27,502).
Chem. Abs. 53:22096A (Abstract of FR 1,058,341).
Valade et al., Compt. Rend. 254, 3693 (1962), p. 1, line 18.
Chem. Abs. 57:5940h (Abstract of Valade et al.).
Kricheldorf et al., Polym. Bull. 1, 383 (1979).
Chem. Abs. 72:12133v (1970), Abstract of FR 1,566,217.
Chem. Abs. 70:115281e (1969), Abstract of Bull. Soc. Chim. Fr., 1969, pp. 262-263.
Burkard Herbert G.
Chao Yuan
Killos Paul J.
Raychem Limited
Rice Edith A.
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