Butynes butynediol

The feed materials, acetylene and formaldehyde are reacted in the presence of CuC2 or Si02 catalyst at 90-100°C at 5 atm to form 1,4—dihydroxy-3— butyne(butynediol), which is then hydrogenated in the presence of Ni or Pd at 100°C to form 1,4-dihydroxy-butane. The 1,4—dihydroxy-butane in the presence of H3PO4 at 100—130°C cyclizes to form THF and water as a byproduct [117]. 

Butynediol. Butynediol, 2-butyne-l,4-diol, [110-65-6] was first synthesized in 1906 by reaction of acetylene bis(magnesium bromide) with paraformaldehyde (43). It is available commercially as a crystalline soHd or a 35% aqueous solution manufactured by ethynylation of formaldehyde. Physical properties are Hsted in Table 2. 

Acetylene is condensed with carbonyl compounds to give a wide variety of products, some of which are the substrates for the preparation of families of derivatives. The most commercially significant reaction is the condensation of acetylene with formaldehyde. The reaction does not proceed well with base catalysis which works well with other carbonyl compounds and it was discovered by Reppe (33) that acetylene under pressure (304 kPa (3 atm), or above) reacts smoothly with formaldehyde at 100°C in the presence of a copper acetyUde complex catalyst. The reaction can be controlled to give either propargyl alcohol or butynediol (see Acetylene-DERIVED chemicals). 2-Butyne-l,4-diol, its hydroxyethyl ethers, and propargyl alcohol are used as corrosion inhibitors. 2,3-Dibromo-2-butene-l,4-diol is used as a flame retardant in polyurethane and other polymer systems (see Bromine compounds Elame retardants). 

Butynediol (2-butyne-l,4-diol melting point 58°C, boiling point 248°C, density 1.114, flash point 152°C) is a stable crystalline solid but violent reactions can take place in the presence of certain contaminants, particularly at elevated temperatures. In the presence of certain heavy-metal salts, such as mercuric chloride, dry butynediol can decompose violently. Heating with strongly alkaline materials should be avoided. 

Electrolytic oxidation gives acetylene dicarboxylic acid (2-butyne-dioic acid) in good yields. Butynediol can be hydrogenated partway to butenediol (HOCH2CH=CHCH2OH) or completely to butanediol (HOCH2CH2CH2CH2OH). 

BUTYNE, 1-CHLORO-4-MERCAPTO-, S-ESTER WITH DIPHENYLPHOSPHINOTHIOATE see CEV840 2-BUTYNE-1.4-DIOL see BST500 1,4-BUTYNEDIOL (DOT) see BST500 BUTYNOIC ACID, 3-PHENYL-2-PROPENYL ESTER see CMQ800... 

Synonyms Butynediol 1,4-Bulynediol 2-Butyne-1,4-dk)l Errpnca/ C4HA Famida HOCH2=CCH20H... 

Dihydroxyethylaniline N,N-Di-(2-hydroxyethyl) aniline N,N-Di(P-hydroxyethyl) aniline. See Phenyidiethanolamine Di-(2-hydroxyethyl) butynediol CAS 1606-85-5 EINECS/ELINCS 216-526-0 Synonyms 1,4-Bis (2-hydroxyethoxy)-2-butyne 2,2 -(2-Butyne-1,4-diylbis (oxy)) bisethanol 1,4-Di-(2-hydroxyethoxy) but-2-yne Ethanol, 2,2 -(2-butyne-1,4-diylbis (oxy)) bis- Ethanol, 2,2 -(2-butynylenedioxy) di-Classification Alkyne Empirical C8H14O4... 

The continuous hydrogenation of butynediol in a cocurrently operated bubble column reactor is chosen as an example for a second order reaction where a sparingly soluble gas phase component (H2) reacts on the catalyst surface with a liquid phase component in excess (butyne-... 

Synonyms Bis (hydroxymethyl) acetylene 2-Butin-1,4-diol Butynediol 1,4-Butynediol 2-Butynediol 2-Butyne-1,4-diol 1,4-Dihydroxy-2-butyne Empirical C4Hg02 Formula H0CH2=CCH20H... 

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