Mixture of esters and use thereof

Details Mixture of esters and use thereof Mixture of esters and use thereof

1998-08-12

2000-10-10

Short, Patricia A.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

525 7, 526320, 560217, 560224, 560225, C07C 6703, C07C 69527, C08L 6708, C08F22226

Patent

active

061302759

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a composition comprising a mixture of esters derivable from maleic and/or fumaric acid, anhydrides and alkyl esters thereof, a process for producing said mixture of esters and use of said ether esters as diluents in paint and polymer formulations.
One of the processes used hitherto to produce 2-substituted succinate esters is the combined transesterification and Michael addition reaction of an alcohol or a monoether of a polyoxyalkylene glycol as described in GB-A-552715 in which ether esters of hydroxysuccinic acid and unsaturated alcohols are prepared by reacting in a single step under anhydrous conditions an alkyl ester of maleic acid with an unsaturated alcohol in the presence of magnesium alkoxide as a catalyst. However, this method when repeated for instance with an octadienol/dimethyl maleate system using magnesium methoxide as described in GB-A-552715 gives products which have a deep red colour. It may be possible to overcome this colour problem in the products described in this prior art by distillation. However, such a distillation is unlikely to be practicable with the synthesis of esters contemplated in the present invention since these esters are all meant to have relatively low volatility and hence are not amenable to purification by distillation.
It has now been found that a mixture of esters can be produced in commercially viable yields and purity by using selective catalysts and process.
Accordingly, the present invention relates to a composition comprising a mixture of a fumarate, maleate and 2-allyloxy-succinate esters falling within the area defined by points A, B, C and D of a triangular chemical composition diagram (hereafter "TCCD") said points representing respectively the ranges of concentration of said maleate, fumarate and succinate in said composition.
Referring to the drawings:
FIG. 1 represents a chemical composition diagram according to the present invention.
Thus, the compositions of the present invention represented by the area defined by points A, B, C and D in the TCCD (see attached FIG. 1) suitably contain the fumarate, maleate and 2-allyloxy succinate esters in the following ranges in parts by weight percent (%): fumarate:maleate:2-allyoxysuccinate=3-90:0-50:10-97 and is preferably in the range from 3-97:0-20:10-97 represented by the area under points A', B', C and D, and more preferably in the range 25-75:0-5:25-75 represented by the area under points E, F G and H.
Specific examples of such mixed esters include:
According to a further embodiment the present invention relates to a process for producing a mixture of esters (hereafter "MOE") represented by formula (I) said process comprising reacting a dicarboxylic compound selected from the group consisting of maleic acid, maleic anhydride, fumaric acid and the dialkyl ester of maleic or fumaric acid with a reactant alcohol R'O[CHR".CH.sub.2 O].sub.x H where x is 0 or an integer from 1-6 in the presence of a catalyst to form said MOE, the catalyst being selected from the group consisting of: para-toluene sulphonic acid and phosphoric acid, and then ##STR1## in which R'.dbd.R and R" is H or an alkyl or an alkylene group having 1 to 2 carbon atoms and, each of a and b is same or different and has a value of 0 or is an integer from 1-6.
By the expression "alkylene" as used herein and throughout the specification is meant a divalent hydrocarbyl group such as eg a --CH.sub.2 --(CHR").sub.t --CH.sub.2 -- group wherein t=0 or an integer and R" has the same notation as above.
R' is derived from the reactant alcohol containing allylic unsaturation which can be modified by reaction with epoxides such as eg ethylene oxide and propylene oxide. Thus, R'O[CHR".CH.sub.2 O].sub.x H where x is 0 or an integer from 1-6 which is used for making the MOE and can be an allylic hydrocarbyl or an allylic hydrocarbyloxy alkylene group. Thus, the first reactant alcohol may be an allylic alcohol and includes inter alia 2-ethyl-hex-2-en-1-ol (which compound will hereafter be referred to as "2-ethylhexenol" for convenience)

Affiliated with

Also associated with

Rating

Mixture of esters and use thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Mixture of esters and use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Mixture of esters and use thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2257477