5-Butylbarbituric Acid Synthesis Essay

10 tion of acyl ureas.

15 is to produce new and useful diureides.

Patented Aug. 17, 1937 UNITED STATES ACYL UREAS AND PROCESS FOR THE PREPARATION THEREOF Ralph A. Jacobson, Wilmington, DeL, assignor to E. I. du Pont de Nemours 8: Company, Wilmington, Dei., a corporation 01' Delaware No Drawing. Application January 24, 1936,

Serial No. 60,706

14 Claims. (Cl. 260-33) This invention relates'to acyl ureas and to a process for the preparation thereof.

Certain acyl ureas have previously been pre-' pared. For example, barbituric acid is ordinarily prepared by condensing urea with malonic ester derivatives by means of sodium ethylate. Acetyl urea is another known acyl urea.

It is an object of the present invention to provide a new and improved process for the prepara- A further object is the provision of a process for the preparation of acyl ureas in which readily available raw materials are employed. An additional object is to produce new and useful acyl ureas. A more specific object Other objects will appear hereinafter.

These objects are accomplished in accordance with the present invention by reacting an alkali metalurea with an ester of a carboxylic acid. The resultant product is an acyl urea, the acyl radical being that present originally in the carboxylic acid.

In practising the invention, it is preferable to carry out the reaction in one of two ways: namely, either in the presence of a catalyst such as, for example, acetone, or by forming the sodium urea in situ in liquid ammonia in the presence of the ester.

The invention will be further illustrated but is not limited by the following examples, in which the quantities given, unless otherwise indicated, are in parts by weight.

EXAMPLE I Acetyl urea A mixture of 880 grams mols) of ethyl acetate, 735 cc. (10 mols) of acetone and 410 grams (5 mols) of sodium urea was placed in a five-liter flask. The mixture was stirred for one hour, during which period considerable heat was developed and a thick precipitate formed. After three hours, the supernatant liquid was decanted off and the solid cooled externally with a freezing mixture. The contents of the reaction vesel were then treated gradually with 300 cc. of 18% hydrochloric acid. Crystalline acetyl urea was obtained which, upon recrystallization from' hot water, gave 193 grams of pure acetyl urea melting at 214 C. I

EXAMPLE II B67120? l urea To 136.1 parts of methyl benzoate were added 82.1 parts of sodium urea and 58.1 parts of acetone. The mixture was stirred vigorously for approximately four hours, allowed to stand overnight, and then treated with 500 parts of water containing 36.5 parts of hydrogen chloride. The crystalline precipitate was filtered, washed on the filter with water and purified by crystallization from hot alcohol. The product obtained melted at 210-212 C. The melting point for pure benzoyl urea is 215 C.

ExAMrLn III Oleyl urea EXAMPLE IV Methacrylyl urea The synthesis of methacrylyl urea was carried out in the cold in a vessel equipped with a stirrer driven by a fairly powerful motor. A five-liter flask was surrounded by an ice bath, and a mixture of 2400 grams (24 mols) of methyl methacrylate, 656 grams (8 mols) of sodium urea and 600 cc. of acetone was added, with vigorous stirring, over a period of three hours, the temperature being kept at 8l2 C. The mixture thickened considerably and acquired a yellow color. The flask was immediately packed in a freezingmixture and 1520 cc. of 18% hydrochloric acid was added, with stirring, at such a rate as not to raise the temperature about 25 C. The slightly acid mixture was then cooled to 2 C. with stirring, and the acyl urea separated by suction filtration. The upper oily layer in the filtrate weighed 1980 grams and contained most of the excess methyl methacrylate. The methacrylyl urea was Washed with several small portions of alcohol and recrystallized from 1300 cc. of alcohol. After cooling to 0 C., the alcoholic solution yielded 843 grams of pure white crystalline methacrylyl urea melting at 132-134 C. Evaporation of the alcoholic mother liquor under reduced pressure gave an additional 41 grams of methacrylyl urea, making a total yield of 37.5%.

The following example illustrates the preparation of methacrylyl urea by forming the sodium urea in situ in liquid ammonia in the presence of the ester. Suitable condensation in this case is obtained without the use of a catalyst.

EXAMPLE V 5 Methacmlyl urea:

To a solution of 200 parts of methyl methacrylate and 120 parts of urea in about 623 parts of liquid ammonia was added 46=parts of sodium metal overa period of three hours. The mixture 0 was allowed to stand for a few hours at about 0., during which time practically all the ammonia evaporated ofif. The residue in the flask was taken up with a small amount of water, the clear solution acidified at about 25 C. with hy- 'drochloric acid, cooled, and the precipitate filtered. The product was purified by crystallization from'hot water. The identity of the product was established by a. nitrogen determination.

The product prepared as described above polymerizes readily upon heating alone or in the presence of a polymerization catalyst, e. g., benzoyl peroxide.

EXAMPLE VI (A) Acyl urea from coconut oil A mixture of 300 parts of coconut oil, about 160 parts of acetone and 100 parts of sodium urea was stirred vigorously for about five minutes, then about 400 parts of additional acetone were added, and stirring continued for about one-half hour. The mixture was allowed to stand overnight, water was added, and the product filtered. The product was dispersed in warm alcohol, filtered,

r and then purified by crystallization from acetic acid. A snow-White crystalline waxy solid melting at 172 C. was obtained.

The acyl urea of coconut oil may also be synthesized by forming the sodium urea in situ in the presence of the ester. Condensation in this 40 case proceeds satisfactorily without a catalyst,

as exemplified below:

EXAMPLE VI (B) Acyl urea from coconut oil 45 A mixture of 60 parts of urea and 213 parts of coconut oil was dissolved in about 930 parts oi. liquid ammonia and to this mixture were added slowly 23 parts of metallic sodium. The clear' solution was allowed to stand overnight, during 0 which time most of the ammonia evaporated 011. Water was added, the mixture acidified with acetic acid, the precipitate filtered, and the product purified by repeated crystallization from acetic 55 acid. The purified product melted at l6 8-1 71 C.

EXAMPLE VII Acyl urea from linseed oil I EXAMPLE VIII Acyl urea from China-wood oil To amixture of '12 parts of acetone and 59 parts of China-wood oil were added, with stir- 7 ring, 10 parts of sodium urea. The mixture was allowed to stand overnight. The product in the fiask was taken up with water, the mixture aciditied with hydrochloric acid, filtered, and the precipitate washed with hot alcohol. The product obtained after repeated crystallizations from toluene melted at 150'l60 C. and had an iodine number 01' 108.8. Analysis of the product showed it to contain 8.13% nitrogen, whereas the theoretical nitrogen content ofeleostearyl urea is 8.97%.

The process of this invention is also applicable to esters of dibasic acids to form compounds of two classes:

(1) With malonic acid esters or with substituted malonic acid esters, ring closure occurs to yield barbituric acid. and substituted barbituric acids. Thus, malonic ester yields barbiturlc acid, while ethyl malonic ester, isopropyl malonic ester and butyl malonic ester yield ethyl barbituric acid, isopropyi barbituric acid and butyl barbituric acid, respectively.

(2) With esters of aliphatic dicarboxylic acids containing more than one carbon atom between the carboxyl groups, diureides are obtained. Thus, diethyl glutarate reacts with two mols of sodium urea to give gt'utaryl diureide.

2NaNHCONHz-l-C2HsOOC(CH2):COOCzHsnniconnco (CH2) :CONHCONI-Ia-l-ZNaOCaHs The above features of the invention are illustrated by the following examples:

EXAMPLE IX 7 Barbituric acid To a solution of 8.8parts of acetone in 40 parts of malonic ester were added 10 parts of sodium urea. The mixture was allowed to stand at room temperature for several days, water added, and then acetic acid ,until slightly acid to litmus. The white precipitate was filtered ofl, dissolved in parts of hot water, acidified with hydrochloric acid, the precipitate filtered. The product obtained was purified by crystallization from alcohol,, 4and analysis showed it to contain 17.48% nitrogen, whereas the theoretical nitrogen content" of barbituric acid dihydrate is 17.07%.

EXAMPLE X Butyl barbituric acid To a solution of 8.8;parts of acetone in 43 parts of n-butyl malonic ester were added, with stirring, 10 parts of powdered sodium urea. The mixture was stirred for one-half hour, allowed to stand at room temperature for several days. treated with a small amount of water, and then filtered. The precipitate wasdissolved in water, acidified and filtered. The product obtained after purification by crystallization from alcohol melted at 208 C. and contained 14.8% nitrogen, whereas the theoretical quantity of nitrogen in butyl barbituric acid is 15.2%.

Exlmrrr XI Ethyl barbituflc acid To a solution of 8.8 parts of acetone in 38 parts of ethyl malonic ester were added, with stirring, 10 parts of sodium urea, and the mixture was stirred for about fit en minutes. After standing for several days at r m temperature, the product in the flask was taken up with a small amount of water, acidified with hydrochloric acid, and the precipitate filtered. The product obtained after purification by crystallization from alcohol melted at 185 C.

ExAMPLi: XII

Isopropyl barbituric acid To a solution of 8.8 parts of acetone in 40 parts of isopropyi malonic ester were added 10 parts of sodium urea. The mixture was stirred for fifteen minutes and allowed to stand at room temperature 10 for several days. To the product in the flask was added a small amount of water, the mixture acidified and filtered. The product obtained was purified by crystallization from alcohol and found to melt at 212 C., which is the known melting point 15 for isopropyl barbituric acid.

EXAMPLE XIII Glutaryl diureide To a mixture of 20 parts of sodium urea, 20 parts of acetone and 23 parts of ethyl glutarate were added 20 parts of additional acetone, and the resultant mixture was allowed to stand at room temperature for twenty-four hours. The mixture was then taken up with a small amount of water, the mass acidified with hydrochloric acid, the precipitate filtered and purified by crystallization from hot acetic acid. The white crystalline product obtained melted at 247248 .0., and analysis showed it to contain 24.6%

nitrogen, whereas the calculated nitrogen content of glutaryl diureide is 25.95%.

EXAMPLE XIV Pimelyl diureide A mixture of 21.6 parts of ethyl pimelate, 16 parts of sodium urea and 20 parts of acetone was allowed to stand overnight. The product in the flask was taken up with a small amount of water,

40 then acidified with hydrochloric acid, and the precipitate filtered. The product obtained after purification by crystallization from hot acetic acid melted at 240-245 C.

EXAMPLE XV Ethyl allophanate To a mixture of parts of diethyl carbonate and 14 parts of sodium urea were added 20 parts of acetone, and the mixture was stirred for several minutes. The reaction mixture was cooled with ice .vater, an additional 12 parts of acetone added, and allowed to stand overnight at room temperature. The semi-solid brown paste was diluted with water, acidified with acetic acid, filtered, and the precipitatepurified by crystallization from hot alcohol. The white crystalline solid obtained melted at 190 C. and was identified as ethyl allophanate. Analysis of the product obtained showed it to contain 21.82% nitrogen, whereas the theoretical nitrogen content of ethyl allophanate is 21.2%.

Similarly, the process of the invention may be applied to the treatment of other esters of monoor polycarboxylic acids. As further examples of such esters may be mentioned propyl acetate, butyl acetate, ethyl propionate, ethyl isobutyrate, ethyl laurate, ethyl undecylenate, ethyl abietate, amyl acetate, lauryl acetate, glycol laurate, stearyl oleate, ethyl levulinate, butyl levulinate, methylricinoleate, amyl benzoate, diethylene glycol phthalate, di(butoxyethoxyethyl)-phthaate, ethyl succinate, propyl maleate, hexyl malonic ester, esters of heterocyclic acids such as pyridine carboxylic acids and quinolinic acid, esters of car- 75 boxylic acids corresponding to the higher alcohols preferred catalysts are ketone catalysts.

obtainable in the synthesis of methanol from carbon monoxide and hydrogen, and carboxylic acid esters of said alcohols as described, for example, in U. S. Patent No. 2,015,077.

As illustrated by the examples, the process is applicable to the preparation of acyl ureas by the reaction of glycerides of fatty acids, e. g., coconutoil, linseed oil and China wood oil, with sodium urea. Similarly, other oils, fats and waxes may be employed, such as, for example,

alfalfa seed oil, hempseed oil, Perilla oil, poppyseed oil, rubberseed oil, sunflowerseed oil, cottonseed oil, kapokseed oil, corn oil, castor oil, teaseed oil, rapeseed oil, pumpkinseed oil, apricot kernel oil, sesame oil, olive oil, palm oil, sperm oil, neats-foot oil, palm nut oil, cod liver oil, lard oil, menhaden oil, sardine oil, candelilla wax, Chinese vegetable tallow, japan wax, carnauba wax, spermaceti and wool grease.

In place of monosodium urea, polyalkali metal ureas such as disodium urea and the corresponding potassium ureas may be employed.

When the reaction is carried out by the formation of sodium urea in situ in liquid ammonia in the presence of carboxylic acid ester, suitable condensation is often obtained without the use of a catalyst. This is illustrated, for instance, in Examples V and VI. Otherwise, for practical purposes it is desirable to employ a catalyst. The use of acetone as a catalyst has given especially desirable results. As further examples of catalysts may be mentioned, methyl ethyl ketone, dipropyl ketone, methyl propyl ketone, dibutyl ketone, and ethyl propyl ketone. In general, the

Likewise in the process where the sodium urea is not formed in situ in liquid ammonia, alcohols, for example, ethyl alcohol, tertiary amyl alcohol, the higher alcohols from the methanol synthesis, propyl alcohol, butyl alcohol, isobutyl alcohol, and

amyl alcohol may be employed as catalysts. It

will be apparent that such catalysts may also function as a solvent or diluent.

The proportions of the various materials employed in carrying out the reaction will vary with the reactants employed and the products desired. For instance, by reacting together monosodium urea and a monocarboxylic acid ester in substantially chemically equivalent proportions a monoacyl urea is obtained. By reacting one molecular proportion of disodium urea with two molecular proportions of the ester, a diacyl urea may be obtained. Usually, in pre paring polyacyl derivatives it is preferable to first form the monoacylatcd derivative, then convert the monoacylated derivative to its alkali metal salt, and finally react this salt with another molecular proportion of the ester. Similarly, in the reaction of monosodium urea with malonic esters to form barbituric acids, substantially equimolar proportions are satisfactory. However, in the preparation of diureides from esters of higher aliphatic dicarboxylic acids, I employ generally two mols of the ester for each mol. of sodium urea.

A number of the diureides described herein are new compounds. These diureides are obtained from esters of acids having the general formula:

HOOC (CH2) nCOOH NHzCONI-ICO (CH2) nCONHCONHZ,

n in both formulas being an integer having a value of at least 3..

In order to produce more complex polyacylated polyureides, diureides of the above type may be converted to the alkali metal derivatives and the latter further reacted with carboxylic acid esters.

The temperatures and pressures of reaction are subject to variation. Usually, it is desirable to conduct the reaction at temperatures as low as practicable. For instance, in most cases, temperatures within the range of 40 C. when liquid ammonia. is used as the reaction medium, to 50 C. have been employed. Higher or lower temperatures may in some cases be used. Ordinarily the reactionis effected under atmospheric pressure, but sub-atmospheric and super atmospheric pressures may be used.

The invention provides a new and useful method for the synthesis of all types of acyl ureas both open and closed chain. Among the latter are barbituric acid and substituted barbituric acids, which products are highly useful as hypnotics.

of diureides. The processes of this invention are particularly valuable in connection with the preparation of long chain acyl ureas, especially those obtained by the direct reaction of sodium urea with naturally occurring oils fats and waxes (fatty acid glycerides). No pretreatment of the fatty oil, for example, saponiflcation, is necessary to obtain directly long chain compounds which are useful as wetting and dispersing agents or as intermediates in the synthesis of wetting and dispersing agents, wax substi-,

tutes, moisture-proofing agents and sizing agents for paper, cloth and the like. By this new and relatively simple reaction, it is possible to obtain a great variety of acyl ureas from natural oils, fats and waxes. These products are also new.

The invention is therefore particularly advantageous in providing new and useful prodnets and a new and improved method of producing well known products such as barbituricacid and derivatives thereof, from readily available raw materials.

The present application is not concerned with the preparation of acyl ureas'from alkali metal ureas and acyl or aralkyl halides, which process is described in my co-pending application Serial No. 60,705 filed of even date herewith. So much of the present application as relates to the preparation of methacrylyl ureas and polymers thereof is claimed in my co-pending application Serial No. 60,739 filed of even date herewith. So much of the presentapplication as relates to the new and improved acyl ureas obtained from naturally occurring oils, fats and waxes is claimed'in my co-pending application Serial No. 60,707 filed of even date herewith.

Among the former are a new group- As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that I do not limit myself to the specific embodiments thereof except as defined in the appended claims. 7

I claim:

1. The process of preparing acyl ureas which comprises reacting an alkali metal urea with an ester of a carboxylic acid.

2. In a process of producing acyl 'ureas by the reaction of sodium urea with an ester of a carboxylic acid, the step which comprises forming the sodium urea in situ'in liquid ammonia in the presence of the ester.

8. The process of producing acyl ureas which comprises reacting sodium urea with an ester of a carboxylic acid in the presence of a ketone as a catalyst.

4. The process of producing acyl ureas which comprises reacting sodium urea with an ester of a carboxylic acid in the presence of acetone.

5. The process of producing acyl ureas which comprises reacting sodium urea with an ester of a carboxylic acid.

6. The process of producing acyl ureas which comprises reacting sodium urea with an ester of a monocarboxylic acid.

7. The process of producing acyl ureas which comprises reacting sodium urea with glycerides of fatty acids.

8. The process of producing acyl ureas which comprises reacting sodium urea with an ester of a polycarboxylic acid.

9. The process of producing cyclic acyl ureas which comprises reacting sodium urea with an ester of an acid selected from the class consisting of malonic acid and alkyl malonic acids.

10. The process of producing barbituric acid which comprises reacting sodium urea with an ester of malonic acid.

11. The process of producing diureides which comprises reacting sodium urea with an ester -of an aliphatic dicarboxylic acid containing a chain of more than one carbon atom between the ester groups.

12. A polyureide of a dicarboxylic acid of the formula HOOC (CH2) nCOOH wherein n is an integer having a value of at least three. 13. A diureide having the general formula NHzCONHCO (CH2) nCONHCONI-h where n is an integer having a value of at least three.

14. Glutaryl diureide.

RALPH A. JACOBSON.

CERTIFICATE OF CORRECTION.

?atent No. 2,090,594. August 17, 1937.

RALPH A. JACOBSON.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows Page 1, second column, line 39, for the Word "about" read above; page 4, first column, line 28, after "oils" insert a comma; and that the said Letters Patent should be read with these corrections therein that the same 'may; conform to the record of the case in the Patent Office.

Signed and sealed this 5th day of October, A. D. 1937.

7 Henry Van Arsdale a- A Acting Commissioner of Patents.

Unformatted text preview: Organic Chemistry II Post-Laboratory Report Experiment #: 12 Malonic Ester Synthesis of Butylbarbituric Acid Introduction: The Malonic Ester Synthesis is very important n the field of organic chemistry because it allows experimenters to make substituted derivatives of acetic acid. This reaction denotes a chemical reaction where diethylmalonate is alkylated at the carbon alpha to both carbonyl groups and then converted to a substituted acetic acid[ CITATION Wel \l 1033 ]. Using the malonic ester synthesis, barbituates can be synthesized. The malonic ester is treated with potassium carbonate, which is added in order to abstract protons from diethylmalonate. The addition of trioctylammonium chloride helps with the transfer of the carbonate ion. Beta-dicarbonyl compounds can be prepared via, Claisden condensation as well as Dieckman condensation. They can thus be utilized in synthesis reactions to perform enolate alkylations. They can also be used for beta-keto acid decarboxylation as well as acetoacetic ester synthesis[ CITATION Jimnd \l 1033 ]. In this experiment, the beta-dicarbonyl synthesis reaction performed is the malonic ester synthesis. This process allows carboxylic acids to be substituted once or twice. In this case butylbarbituric acid is synthesized. The Mechanism for the Malonic ester synthesis of butylbarbituric acid is as follows: Two possible side reactions that could take place are illustrated as follows: A) B) Procedure: PART A: The following compounds were weighed out and mixed into a 5ml conical vial: 400mg of diethylmalonate, 40mg of trioctylmethylammonium chloride, 350 mg of 1bromobutane and 415mg of anhydrous potassium carbonate. A reflux condenser was then attached and the mixture heated at reflux for an hour. The mixture was then transferred to a separatory funnel, rinsing the thick mixture out of the flask with 2.5mL of water. The mixture was then shaken, the water allowed to separate, draining it out and saving it. the remaianing organic layer was then transferred to a storage flask. The water layer was then exracted with two 1.0mL portions of diethyl ether, combining these with the organic layer. The ether mixture was then dried over anhydrous sodium sulphate, and then the solution was decanted into a 5mL round bottomed-flask. The solvent was then evaporated under a vacuum using a vacuum pump. The removal of the ether was then completed by connecting the flask to the vacuum pump. The weight was then determined and the percent yield calculated. The product was then analyzed by TLC on silica gel using dichloromethane. The product was then compared to pure diethyl n-butylmalonate. PART B: 100mg of diethyl butylmalonate, 30mg of urea and boiling stones were placed into a 5mL conical vial. 3mL of 21% sodium ethoxide in ethanol was added and refluxed on sand for 1.5 hr. The reflux apparatus was then cooled, the solution transferred to a 25mL beaker and 2M HCL was added carefully until indicated acidic by the pH paper. The beaker was heated until half the volume has decreased and the mixture was allowed to cool along with occasional scratching. The solid was then suction-filtered and the funnel washed with hexane added dropwise. The product was then recrystallized from hot water. The product was then air dried and the melting point and percent yield was determined. Table 1. Showing the physical and chemical properties of the chemical used during this experiment[ CITATION Che08 \l 1033 ]. Chemical Molar mass Melting point Boiling point (g) °C °C Diethylmalonate 160.17 Trioctylmethylammonium 404.16 -50 -20 199 240 chloride 1-bromobutane 137.02 -112 100-104 Diethyl n-butylmalonate Butylbarbituric acid 216.27 224.25 - 235-240 - Chemical Properties Colorless liquid Vixcous colorless to pale orange liquid Clear-yellow liquid Clear liquid - Toxicity/Hazards: Table 2. Showing the toxicity of the chemicals used during this experiment[ CITATION Che08 \l 1033 ] Chemical Hazards 1-bromobutane Irritating to the eyes, nose, throat and upper HCl respiratory tract Concentrations of 1000 to 2000 ppm are dangerous even for brief exposures. Results: Table 3. Showing the physical properties of the product, Diethyl butylmalonate, obtained in the experiment: Weight (g) Melting Point (°C) Rf 0.243 * 0.70 * No melting point was obtained, as the second part of the experiment was not conducted due to a very low success rate. Percentage Yield Calculation: Moles Diethylmalonate = 0.4g/160.17g/mol =0.00249 Moles 1-bromobutane = 0.35g/137.02g/mol = 0.00255 Moles Diethyl butylmalonate = 0.243g/216.27g/mol = 0.0011 Percent Yield = (actual moles/ theoretical moles) x 100 = (0.0011/0.00249) x 100 = 44% Rf Calculation: Diethyl n-butylmalonate = 37/58 = 0.64 Diethylmalonate = 32.5/58 = 0.56 Product (Diethyl butylmalonate = 41/58 = 0.70 1-bromobutane = 0/58 = 0 Discussion: Based on the experiment carried out, it was found that the percent yield of the obtained Diethyl butylmalonate product was found to be 44%. The fact that the percent yield is below 50% could be due to human error, faulty experimental construction, as well as inaccurate measurements. Also, this low percent yield could be due to over-washing of the final product. Additionally, TLC was utilized throughout this experiment to ensure the successful conversion of starting materials to products. The Rf of the diethyl butylmalonate product was found to be 0.7, which is indeed similar to the literature value of 0.64. This Rf value is very much expected as the product is less polar than the starting materials and will thus be pulled further along the solvent front by the non-polar eluent, dichloromethane. Conclusion: Based on this experiment done, it can be confirmed that part one of this experiment successful, whereas part 2 was poorly constructed and was not carried out due to its low success rate. However, the Rf value of the diethyl butylmalonate product confirmed that all starting materials were converted into product. However, the percent yield was found to be lower than 50% due to many contributing factors. The techniques utilized during this experiment can be applied to chemical industries worldwide as organic chemists utilize barbituric acid quite often. References: Works Cited Chemical Book. Chemical Book. nd nd 2008. 26 October 2014 <www.chemicalbook.com>. Hollister, Jim. Preparation of Bea Dicarbonyl Compounds. nd nd nd. 9 April 2015 <sasc-specialists.ucdavis.edu>. Solomons, T.W. Graham. Organic Chemistry. Danvers: Wiley, n.d. Weldegirma, Solomon. Experimental Organic Chemistry Laboratory Manual: CHM 2210L. Tampa: Department of Chemistry, n.d. ...
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