2-butyne-1,4-diol

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Structural formula
Structural formula of 2-butyne-1,4-diol
General
Surname 2-butyne-1,4-diol
other names
  • But-2-yn-1,4-diol ( IUPAC )
  • 1,4-butynediol
  • Bis (hydroxymethyl) acetylene
  • Butynediol
Molecular formula C 4 H 6 O 2
Brief description

colorless, crystalline solid

External identifiers / databases
CAS number 110-65-6
EC number 203-788-6
ECHA InfoCard 100.003.445
PubChem 8066
ChemSpider 7775
Wikidata Q209328
properties
Molar mass 86.09 g mol −1
Physical state

firmly

density

1.11 g cm −3

Melting point

58 ° C

boiling point

238 ° C

solubility
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 05 - Corrosive 08 - Dangerous to health

danger

H and P phrases H: 301 + 311 + 331-314-317-373
P: 261-280-301 + 310-305 + 351 + 338-310
MAK
  • DFG : 0.1 ml m −3 or 0.36 mg m −3
  • Switzerland: 0.1 ml m −3 or 0.36 mg m −3
Toxicological data

105 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Butyne-1,4-diol (according to IUPAC nomenclature : but-2-yne-1,4-diol , often simply referred to as butynediol ) is an organochemical compound from the group of alcohols , more precisely the alkynols . The substance comes on the market as a 34% aqueous solution and as crystalline flakes. It is an intermediate product in the chemical industry that is processed into numerous products.

Extraction and presentation

For the industrial synthesis of 2-butyne-1,4-diol are employed acetylene with 10 - 30% strength formaldehyde solution with bismuth -modified on silica supported copper (I) acetylide - catalysts at temperatures of 65 to 90 ° C and pressures from 0.9 to 10 bar. The by-product is propargyl alcohol , which is separated off by distillation and returned to the reaction stage again. The selectivity to 2-butyne-1,4-diol is> 90% based on formaldehyde and approx. 80% based on acetylene. The complete reaction takes place in a cascade of two or more fixed bed reactors , which are operated in the sump or trickle mode.

Reaction of acetylene with formaldehyde to give 2-butyne-1,4-diol in the presence of a bismuth / copper acetylide catalyst

A large-scale plant for this synthesis method was built as early as 1941.

The European annual production of butynediol is around 200,000 t. One of the largest manufacturers in Europe is u. a. ISP Marl GmbH, a subsidiary of Ashland Inc.

use

Butynediol is the starting point for the synthesis of other diols. It can be converted to 1,4-butenediol and further to 1,4-butanediol by hydrogenation . Furthermore, it is used for the production of drugs, e.g. B. used as a raw material for vitamin B6 , defoliants , flame retardants , corrosion inhibitors , plasticizers and polyurethanes (chain-extending agents). It is also used as a brightener in electroplating baths (for nickel and copper) and as a saving additive to remove scale or oxide layers on metals and in paint strippers.

safety instructions

2-Butyne-1,4-diol decomposes easily when heated (from 160 ° C), whereby the reaction can be very violent in the presence of impurities or at higher temperatures (flash point 136 ° C).

Individual evidence

  1. ↑ a b c d e f g h i Entry on 2-butyne-1,4-diol in the GESTIS substance database of the IFA , accessed on October 1, 2019(JavaScript required) .
  2. ↑ Entry on but-2-yn-1,4-diol. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2019.
  3. ↑ Entry on But-2-yne-1,4-diol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 1, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Data sheet 2-Butyne-1,4-diol purum from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).
  5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 110-65-6 or 2-butyne-1,4-diol ), accessed on October 1, 2019.
  6. ↑ Rolf Pinkos, Rudolf Erich Lorenz, York Alexander Best: A process for producing 1,4-butanediol. In: Google Patents. BASF SE, June 7, 2017, accessed April 24, 2019 .
  7. ↑ Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , p. 108 .
  8. ^ History of BASF ( Memento from September 29, 2007 in the Internet Archive ).
  9. ↑ a b Toxicological assessment of butynediol (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
  10. ↑ Performance Materials. (No longer available online.) In: chemsite.de. Archived from the original on April 12, 2016 ; Retrieved May 19, 2016 . Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / www.chemsite.de
  11. ↑ Linde / Yukong process for the production of butanediol via butynediol ( Memento from September 29, 2007 in the Internet Archive ) (PDF file; 37 kB)
  12. ↑ Data sheet 2-Butyne-1,4-diol (Crystal) ( Memento from March 18, 2014 in the Internet Archive ) from BASF, accessed on December 18, 2014.
  13. ↑ Data sheet 2-butyne-1,4-diol from Gischem, accessed on December 18, 2014.

Web links