Butyric anhydrides

Butyric anhydride is a wafer-white liquid which hydrolyzes to butyric acid in the presence of water. Like butyric acid, it is used in making butyrates, flavors, drugs and tanning agents. 

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Yields of the order of 85% were secured in the dry reaction (48). (Propionic anhydride and butyric anhydride can be obtained similarly from their sodium salts.) Inasmuch as dinitrogen tetroxide can be regenerated, the economic prospects of this novel way of making anhydride are feasible. 

Cellulose acetate [9004-35-7], prepared by reaction of cellulose with acetic anhydride, acetic acid, and sulfuric acid, is spun into acetate rayon fibers by dissolving it in acetone and spinning the solution into a column of warm air that evaporates the acetone. Cellulose acetate is also shaped into a variety of plastic products, and its solutions are used as coating dopes. Cellulose acetate butyrate [9004-36-8], made from cellulose, acetic anhydride, and butyric anhydride in the presence of sulfuric acid, is a shock-resistant plastic. 

V,7V,7V, 7V -Tetramethylethylenediamine (TMEDA, TEMED) [110-18-9] M 116.2, b 122°, d 1.175, n 1.4153, pK 5.90, pKj 9.14. Partially dried with molecular sieves (Linde type 4A), and distd in vacuum from butyl lithium. This treatment removes all traces of primary and secondary amines and water. [Hay, McCabe and Robb J Chem Soc, Faraday Trans 1 68 1 1972.] Or, dried with KOH pellets. Refluxed for 2h with one-sixth its weight of n-butyric anhydride (to remove primary and secondary amines) and fractionally distd. Refluxed with fresh KOH, and distd under nitrogen. [Cram and Wilson 7 Am C/iem Soc 85 1245 796i.] Also distd from sodium. 

Coumarin formation proceeds via an intramolecular attack by enol ester 9 on the ketone to give 10. Dehydration of 10 then affords coumarin 11. It has been observed that coumarins are favored when higher order homologs of acetic anhydride and their corresponding salts such as propionic anhydride/sodium propionate and butyric anhydride/ sodium butyrate are used. 

A Preparation of a-Ethyl-m-Nitrocinnamic Acid This acid is prepared from 100 g of m-nitrobenzaldehyde, 210 g of butyric anhydride and 73 g of sodium butyrate. The crude a-ethyl-m-nitrocinnamic acid is crystallized from ethanol giving about 105 g, MP 140° to 142°C. From the filtrates there may be isolated a small amount of a stereoisomer, which when pure melts at 105° to 106°C. 

The reaction mixture was then kept at room temperature for 1 hour and thereafter poured into a mixture of 5.0N HCI and crushed ice. The benzene solution was immediately washed with water, with cold 1. ON NaHCOsand finally with cold water. After drying over anhydrous sodium sulfate, the benzene was removed in vacuo. The residue is the p-[N-bis(/3-chloroethyD-amino] phenyl butyric anhydride which could be used without any further purification. 

To a solution of 42.0 g of p-[N-bis(/3-chloroethyl)amino] phenyl butyric anhydride in 500 ml dry pyridine was added 24.4 g of prednisolone. The reaction mixture was kept at room temperature for 24 hours under anhydrous condition. It was then poured into a mixture of concentrated HCI and crushed ice and extracted with ether-ethyl acetate (1 1). 

Methohexital sodium Butyramidophenol Acebutolol Butyric anhydride lopanoic acid Tyropanoate sodium n-Butyryl chloride Ethacrynic acid... 

Acetic anhydride Propionic anhydride Butyric anhydride Maleic anhydride Phthalic anhydride Acetyl chloride Propionyi chloride Butyryl chloride Hexonyl chloride Benzoyl chloride Oxalyl chloride Chloroacetyl chloride Dichloroacetyl chloride Trichloroacteyl dtloride... 

Aluminum phosphide Amyl trichlorosilane Benzoyl chloride Boron tribromide Boron trifluoride Boron trifluoride etherate Bromine pentafluoride Bromine trifluoride n-Butyl isocyanate Butyllithium Butyric anhydride Calcium Calcium carbide Chlorine trifluoride Chloro silanes Chlorosulfonic acid Chromium oxychloride Cyanamide Decaborane Diborane... 

Suttie etal. (1997, 1998) tested wood samples modified with acetic, propionic or butyric anhydride in EN113 tests, and in vermiculate overlay tests based upon BS 1982. 

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