reactive acetylemic alcohols and halides - C&EN Global Enterprise

Nov 5, 2010 - Chem. Eng. News , 1954, 32 (25), p 2509. DOI: 10.1021/cen-v032n025.p2509. Publication Date: June 21, 1954. Copyright © 1954 AMERICAN ...
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reactive ocetyiemc alcohols and naiides PROPARGYL

ALCOHOL reactions

HC=CCH2OH

Oxidation —^Propiolaldehyde HC==CCH0 Oxidative Coupling—^2,4-Hexadiyne-l,6-dioI H0CH2C=C--C=CCH20H Replacement of OH—*.Propargyl halides HC=CCH2X Halogenation—>>3-Halo-2-propyn-l-ol CIC=CCH20H Also reduction, esterification, hydration, trimerization, etc.

Three centers of reactivity —primary alcohol —active hydrogen—triple bond

suggested PROPARGYL

applications

BROMIDE

Chemical intermediate for Sulfadiazine and other pharmaceuticals, for agricultural chemicals, textile auxiliaries, etc. Corrosion inhibitor and stabilizer for halogenated compounds.

CHLORIDE

reactions

HC=CCH,Br PROPARGYL HC=CCH,CI

Reformatsky type-

CHa •Acetylenic carbinols Η0=0ΟΗ20-ΟΗ=ΟΗ2 OH

Three centers of reactivity—active halide—active hydrogen—triple bond

Amination—^Propargyl amines HC=CCH2NHR Etherification—^Propargyl ethers HC==CCH20R

suggested

applications

Chemical intermediates for terpenes and pharmaceuticals including vitamins, hormones, etc. Agricultural uses as soil fumigants, etc.

2-BUTYNE-1.4-DIOL HOCH,C=CCH,OH

reactions Replacement of OH—^l,4-Dihalo-2-butyne XCH2C=CCH2X Isomerization-—^Hydroxymethyl vinyl ketone H0CH2COCH=CH2 Trimerization—^HexamethylolbenzeneC6(CH2OH)6 Alcohol Addition—^Alkyl ether of 1,4 dihydroxy-2-butanone H0CH2C0CH2CH20R Also hydrogénation, esterification, halogenation, hydration, etherification, etc.

Reacts as a glycol and a disubstituted acetylene

suggested

applications

Chemical intermediate for pharmaceuticals, solvents, explosives, plasticizers, plastics, etc. Corrosion inhibitor and stabilizer for halogenated compounds.

GENERAL ANILINE & FILM CORPORATION

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