Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2001-08-30
2003-02-04
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C554S068000, C564S123000, C564S133000, C564S138000
Reexamination Certificate
active
06515153
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for forming esters and amides wherein said process is conducted using a spinning disc reactor. The invention also relates to a process for making ester and amide precursors, inter alla, acid chlorides wherein a spinning disc reactor is used in combination with reaction intermediates to increase reaction yields and purity. In addition, the present process relates to transesterfication reactions which can be conducted using a spinning disc reactor.
BACKGROUND OF THE INVENTION
Setting aside the ubiquity of side reactions, even the most direct organic reactions result in the need for purification, for example, removal of excess reagent, solvent. Impurities, however, are typically reaction products which have been formed by an alternate reaction pathway or can be products having an undesirable spatial orientation, therefore, in many instances, they resemble the final desired reaction product. The organic chemist seeks to ameliorate the formation of these product-like impurities by adjusting the reaction strategy, the reaction condition, inter alia, temperature, rate of addition, as well as the reactant stoichiometry. In fact, purification costs for some organic reactions may exceed the cost of raw materials.
The formation of amides and esters by the reaction of a carboxylic acid and an amine or an alcohol are two of the oldest, but most utilitarian reactions known since the amide and ester group are perhaps the most abundant of organic functional groups. Their ease of formation also makes the preparation of these functional groups highly susceptible to undesirable by-products. Peptide chemsists have dealt with the formation of amide and ester bonds for over a century and have worked out many procedures for the facile formation of amide and ester bonds in the presence of other reactive functional groups, however, many of these procedures are not applicable on either an intermediate or a large, industrial scale.
One problem faced with esters and amides is the fact the reactants, by the very nature of their own functional groups, carboxylic acids, amines, and alcohols, are more water soluble than the corresponding products. Therefore, during formation of the final product, there can be phase separations, as well as the formation of final products (esters and amides) which are more reactive than the carboxylic acid starting material. This latter case can lead to unwanted transamidation or transesterification.
Certain types of amides and esters necessarily have like reactive units, inter alia, N-acyl amino acids. In the area of bleach catalysts many of the compounds are carboxylic acids comprising an amide bond within the molecule. There is a long felt need to be able to directly form these materials without the high cost of purification or without the need to engage in several processing steps which would added cost to the final product.
It has now been surprisingly found that carboxylic acids comprising an amide functional group can be prepared by the use of a spinning disc reactor, said reactor affording a final product which has enhanced purity and yield.
SUMMARY OF THE INVENTION
The present invention meets the aforementioned need in that it has been surprisingly discovered that the use of a spinning disc reactor when conducting amide and ester forming reactions provides a reaction product having enhanced yields and reduced reaction side products.
The first aspect of the present invention relates to a process for preparing a compound having the formula:
R
1
—CO—NR
3
—R
2
—COOH
or
R
1
—NR
3
—CO—R
2
—COOH
wherein R
1
is C
1
-C
12
linear or branched alkyl, C
6
-C
14
aryl, C
7
-C
14
alkyl substituted aryl unit; R
2
is C
1
-C
14
alkylene, C
6
-C
14
arylene, C
7
-C
14
alkyl substituted arylene; R
3
is hydrogen, C
1
-C
10
alkyl, C
6
-C
10
aryl, C
7
-C
10
alkyl substituted aryl, said process comprising the steps of:
a) charging to a spinning disc reactor a carboxylic acid having the formula:
R
1
—COOH;
with an amine having the formula:
HNR
3
—R
2
—COOH;
or a carboxylic acid having the formula:
HOOC—R
2
—COOH;
with an amine having the formula:
R
1
—NR
3
H;
to form an amide; and
b) isolating said amide.
A further aspect of the present invention relates to a process wherein a reactive intermediate is formed, inter alia, a acid chloride prior to addtion of the amine.
These and other objects, features, and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims. All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C.) unless otherwise specified. All documents cited are in relevant part, incorporated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION
Spinning Disc Reactor
The present invention relates to the use of a spinning disc reactor. The reactor itself may be configured in any manner which is convenient to the formulator, however, each of the one or more discs or plates rotate about an axis. The plates themselves are enclosed within a container suitable for carrying out the herein described reactions. For the purposes of the present invention, the reactants can by charged to the plate at any point along the surface, however, one embodiment relates to addition of all reactants, including solvents at the axis and allowing the centrifugal created by the rotating disc to provide a means for admixing the reactants.
Non-limiting examples of spinning disc reactors are disclosed in “Process Intensification: The opportunity presented by spinning disk reactor technology;”
Inst. of Chem. Eng. Symp. Ser
. 1997; R. Jachuck, C. Ramshaw, K. Boodhoo, and J Dalgleish, 141, 417-424; “Photo-initiated polymerisation using spinning disc reactor,” Jachuck, R. J. and Ramshaw, C., Third International Conference on PI, Antwerp 25-27 October 1999; and “Process Intensification: spinning disc polymeriser,” IchemE Research Event—First European Conference for Young Researchers in Chemical Engineering.
The speed of rotation of the disc and the rate at which the reactants are introduced ontot the disc can be modified by the formulator to meet the requirements of the process. For example, depending upon the time necessary for the reaction be complete, the viscosity of the reactant admixture, the rotational velocity can be adjusted to shorten or lengthen the resonance time of the reactants on each plate. In one embodiment, the plates have a velocity in acess of 100 revolution per minute (rpm), while another embodiment relates to speeds of from 1000 rpm to 2000 rpm. Depending upon the size of the rotating plates and the rotational velocity, resonance times are from 1 second to 15 seconds. Another embodiment employs resonace times of from about 2 to about 10 seconds.
The process of the present invention can be conducted at any temperature within the operable limits of the spinning disc reactor. For exothermic reactions, the apparatus is cooled within a range of from about 0° C. to about 50° C.
The following is a description of the process of the present invention.
Step (a)
Step (a) of the process of the present invention relates to formation of an amide bond by reacting a carboxylic acid having the formula:
R
1
—COOH
with an amine having the formula:
HNR
3
—R
2
—COOH;
to form an amide having the formula:
R
1
—CO—NR
3
—R
2
—COOH
or a carboxylic acid having the formula:
HOOC—R
2
—COOH;
with an amine having the formula:
R
1
—NR
3
H;
to form an amide having the formula:
R
1
—NR
3
—CO—R
2
—COOH
wherein R
1
is C
1
-C
12
linear or branched alkyl, C
6
-C
14
aryl, C
7
-C
14
alkyl substituted aryl unit; R
2
is C
1
-C
14
alkylene, C
6
-C
14
arylene, C
7
-C
14
alkyl substituted arylene; R
3
is hydrogen, C
1
-C
10
alkyl, C
6
-C
10
aryl, C
7
-C
10
alkyl substituted aryl.
Either of the starting materials can be dissolved in a suitable solvent, non-limiting examples of which include tetrahydrofuran, dimethylformamide, methylene chloride, benzene, toluene, and
Burns Michael Eugene
Gibson Michael Steven
York David William
Carr Deborah D.
McBride James F.
Miller Steven W.
The Procter & Gamble & Company
Zerby Kim W.
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