Adipic acid diethyl ester

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

Adipic acid, diethyl ester. See Diethyl adipate Adipic acid, dihexyl ester. See Dihexyl adipate Adipic acid dihydrazide CAS 1071-93-8 EINECS/ELINCS 213-999-5 Synonyms Adipic dihydrazide Adipodihydrazide Adipoyl hydrazide Hexanedioic acid, dihydrazide Ciassification Nonaromatic amide hydrazide Definition Reaction prod, of hydrazine and adipic acid... 

CAS 141-28-6 EINECS/ELINCS 205-477-0 Synonyms Adipic acid, diethyl ester Diethyl adipatate Diethyl hexanedioate 1,6-Diethyl hexanedioate Ethyl adipate Ethyl 5-carboethoxyvalerate Hexanedioic acid, diethyl ester Empirical C10H18O4 Formula (-CH2CH2COOC2H5)2 Properties Colorless liq. sol. in alcohol, many other org. soivs. insol. in water m.w. 202.25 sp.gr. 1.009 m.p. -18 C b.p. 240-251 C flash pt. (CC) > 100 C ref. index 1.427 (20 C)... 

Intramolecular acylations often go very well indeed when a five- or a six-membered ring is being formed, A classic case is the cyclization of the diethyl ester of adipic acid (diethyl hexanedioate), a component in nylon manufacture. 

It may also help to distil out the water that is formed in the reaction diethyl adipate (the diethyl ester of hexanedioic acid) can be made in toluene solution using a sixfold excess of ethanol, concentrated H2SO4 as catalyst, distilling out the water using a Dean Stark apparatus. You can tell from the yield that the equilibrium is very favourable. 

Hexanedioic acid, diethyl ester. See Diethyl adipate... 

Divinyl esters reported first by us are efficient monomers for polyester production under mild reaction conditions. In the lipase PF-catalyzed polymerization of divinyl adipate and 1,4-butanediol in diisopropyl ether at 45°C, a polyester with molecular weight of 6.7 x 10 was formed, whereas adipic acid and diethyl adipate did not afford the polymeric materials under similar reaction conditions (Scheme 3). 

Moreover, succinic diethyl ester was former 1 from the malotnc acid, and adipic diethyl ester from the suermie acid. 

Adipic Acid.—The ethyl potassium salt was converted into the sebaeic diethyl ester by Brown and Walker1 ... 

Note DES-diethyl sebacate, DBS-dibutyl sebacate, DOS-dioctyl sebacate, DMP-dimethyl phthalate, DOP-dio-ctyl phthalate, DHP-dihexyl phthalate, DBP-dibutyl phthalate, DNP-dinonyl phthalate, DDP-didodecyl phtha-late, DEPh-diethyl phosphate, DBPh-dibutyl phosphate, DBA-dibutyl adipate, DOA-dioctyl adipate, TCPh-tricresyl phosphate, TBPh-tributyl phosphate, BBP-hutyl henzyl phthalate, BBS-butyl benzyl sebacate, BBA-butyl benzyl adipate, DNBAA-dinonyl ester of benzylsuccinic acid, TGM-3-trioxyethylene-a,C0-dimethacrylate, LZ-7-ester of diethyleneglycol and synthetic fatty acids of the C -Cg fraction, DBCF-dibutylcarbitol formal, DBE-dibenzyl ether. 

Just as there is an intramolecular version of the aldol condensation (see Section 22.2), there is an intramolecular version of the Claisen condensation. A simple illustration is treatment of an a,(0-diester such as diethyl 1,6-hexanedioate (77, the diethyl ester of adipic acid called diethyl adipate see Chapter 20, Section 20.9) with sodium ethoxide in refluxing ethanol. When this experiment is done, triphenylmethide (19 introduced in Section 22.1) is used as the base, and reaction in the solvent benzene gives the isolated flnal product (86) in 70% yield. Note that benzene is rarely used now-a-days because it is a suspected carcinogen and its use is being phased out. This reaction sequence uses the same mechanism as the Claisen condensation. 

In lipase-catalyzed transesterifications, enol esters have been used as acyl agents (4), since the leaving unsaturated alcohol irreversibly tautomerizes to an aldehyde or a ketone, leading to the desired product in high yields. Bis(enol ester)s were reported to be much effective for the enzymatic synthesis of polyesters imder mild reaction conditions (Fig. 6) (108) the polymerization of divinyl adipate and 1,4-butanediol proceeded by lipase PF at 45°C, and adipic acid and diethyl adipate did not afford the pol5mieric materials under the similar reaction conditions. 

Scheme 9.146. A representation of an intramolecular Claisen-type condensation (an acyloin condensation) in which the diethyl ester of 1,6-hexanedicarboxylic acid (diethyl adipate, CH3CH202C(CH2)4C02CH2CH3)) undergoes cychzation to yield ethyl 2-oxocyclopentanecarboxylate in the presence of ethoxide anion ( OCH2CH3) in ethanol (ethyl alcohol, CH3CH2OH) solvent.

Ethyl maleate of almost equal purity may be obtained by refluxing a mixture of 20 g. of pure maleic a.oid, 37 g. (47 ml.) of absolute ethyl alcohol, 05 ml. of sodium-dried benzene and 4 ml. of concentrated sulphuric acid for 12 hours. The ester is isolated as described for Diethyl Adipate (Section 111,100). The yield of diethyl maleate, b.p. 219-220°, is 26 g. 

Several modifications of the simple direct esterification procedure described above have been developed. For example, it is sometimes convenient to prepare an ester by heating the organic acid, the alcohol and sulphuric acid in a solvent such as toluene. This method is illustrated by the preparation of diethyl adipate for which the procedure is particularly well suited (Expt 5.144). 

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