1,4-Butynediol: Difference between revisions

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	{{chembox		{{chembox
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~444003443~~		\| verifiedrevid = 477205983
	\| Name = 1,4-Butynediol		\| Name = 1,4-Butynediol
	\| Reference =<ref></ref>		\| Reference =<ref></ref>
	\| ImageFile = Butynediol.png		\| ImageFile = Butynediol.png
	\| ImageSize = ~~150px~~		\| ImageSize = 160px
			\| ImageAlt = Skeletal formula
	\| ImageName = 1,4-Butynediol
			\| ImageFile1 = Butynediol-3D-balls.png
⚫	\| ~~IUPACName~~ = But-2-yne-1,4-diol
			\| ImageSize1 = 180
⚫	\| OtherNames = Butynediol<br />2-Butyne-1,4-diol<br />1,4-Dihydroxy-2-butyne
			\| ImageAlt1 = Ball-and-stick model
⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| PIN = But-2-yne-1,4-diol
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| OtherNames = Butynediol<br />2-Butyne-1,4-diol<br />1,4-Dihydroxy-2-butyne
		⚫	\|Section1={{Chembox Identifiers
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 16413		\| ChEBI = 16413
			\| ChEMBL = 3187551
	\| ChemSpiderID = 7775		\| ChemSpiderID = 7775
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C02497		\| KEGG = C02497
			\| PubChem = 8066
			\| EC_number = 203-788-6
			\| RTECS = ES0525000
			\| UNNumber = 2716
			\| UNII = AXH202FPQM
	\| InChI = 1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2		\| InChI = 1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2
	\| InChIKey = DLDJFQGPPSQZKI-UHFFFAOYAT		\| InChIKey = DLDJFQGPPSQZKI-UHFFFAOYAT
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	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 110-65-6		\| CASNo = 110-65-6
	\| SMILES = OCC#CCO		\| SMILES = OCC#CCO
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=4\|H=6\|O=2
	\| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>
			\| Density = 1.11 g/cm<sup>3</sup> (at 20 °C)<ref name=GESTIS>{{GESTIS\|ZVG=29180}}</ref>
	\| MolarMass = 86.09 g/mol
			\| Appearance = Colorless crystalline solid<ref name=GESTIS/>
	\| Density = 1.2 g/cm³
			\| Solubility = 3740 g/L<ref name=GESTIS/>
	\| MeltingPt = 52–55 °C
			\| MeltingPtC = 58
	\| BoilingPt = 238 °C
			\| MeltingPt_ref= <ref name=GESTIS/>
			\| BoilingPtC = 238
			\| BoilingPt_ref= <ref name=GESTIS/>
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| NFPA-H = 2		\| NFPA-H = 2
	\| NFPA-F = 1		\| NFPA-F = 1
	\| NFPA-R = 0		\| NFPA-R = 0
			\| FlashPt = ~{{convert\|136\|C\|F}}
			\| FlashPt_ref = <ref name=GESTIS/>
			\| GHSPictograms = {{GHS05}} {{GHS06}} {{GHS07}} {{GHS08}}
			\| GHSSignalWord = Danger
			\| HPhrases = {{H-phrases\|301\|312\|314\|317\|331\|373}}
			\| PPhrases = {{P-phrases\|260\|261\|264\|270\|271\|272\|280\|301+310\|301+330+331\|302+352\|303+361+353\|304+340\|305+351+338\|310\|311\|312\|314\|321\|322\|330\|333+313\|363\|403+233\|405\|501}}
	}}		}}
	}}		}}

	'''1,4-Butynediol''' is an ] that is an ] and a ]. ~~This~~ ~~yellow~~ ~~crystalline~~ solid is soluble in water and ].		'''1,4-Butynediol''' is an ] that is an ] and a ]. It is a colourless, hygroscopic solid that is soluble in water and polar ]s. It is a commercially significant compound in its own right and as a precursor to other products.

	==Synthesis==		==Synthesis==
	1,4-Butynediol can be produced in the ], where ] and ] are the reactants:		1,4-Butynediol can be produced in the ], where ] and ] are the reactants:<ref name="Ullmann">{{Ullmann\|first1=Heinz\|last1=Gräfje\|first2=Wolfgang\|last2=Körnig\|first3=Hans-Martin\|last3=Weitz\|first4=Wolfgang\|last4=Reiß\|first5=Guido\|last5=Steffan\|first6=Herbert\|last6=Diehl\|first7=Horst \|last7=Bosche\|first8=Kurt\|last8=Schneider\|first9=Heinz\|last9=Kieczka\|title=Butanediols, Butenediol, and Butynediol\|year=2000\|doi=10.1002/14356007.a04_455}}</ref>
	:2 CH<sub>2</sub>O + ~~HCCH~~ → HOCH<sub>2</sub>CCCH<sub>2</sub>OH		:2 CH<sub>2</sub>O + HC≡CH → HOCH<sub>2</sub>CCCH<sub>2</sub>OH

	Several patented production methods use ] ] ]s coated on an inert material. The normal temperature range for the reaction is 90 °C up to 150 °C, depending on the pressure used for the reaction which can range from 1 to 20 bar.<ref>{{cite journal		Several patented production methods use ] ] ]s coated on an inert material. The normal temperature range for the reaction is 90 °C up to 150 °C, depending on the pressure used for the reaction which can range from 1 to 20 bar.<ref>{{cite journal
	\| title = Butynediol synthesis. A kinetic study		\| title = Butynediol synthesis. A kinetic study
	\| author = Kale S. S., Chaudhari R. V., Ramachandran P. A.		\| author = Kale S. S.
			\| author2 = Chaudhari R. V.
			\| author3 = Ramachandran P. A.
	\| journal = Industrial & Engineering Chemistry Product Research and Development		\| journal = Industrial & Engineering Chemistry Product Research and Development
	\| year = 1981		\| year = 1981
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	}}</ref>		}}</ref>

	==Applications==		== Applications ==
	1,4-Butynediol is a precursor to ]. It is also used in the manufacture of ~~plant protection~~ ~~agents, pesticides~~, textile additives, corrosion inhibitors, ~~platicizers~~, synthetic resins, and ]s.~~<ref name="NJ"></ref>~~ It is the major raw material of ].<ref></ref> It is also used for brightening, preserving, and inhibiting nickel plating.		1,4-Butynediol is a precursor to ] and ] by ]. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and ]s. It is the major raw material used in the synthesis of ].<ref>{{Cite web \|url=http://www.swchemical.com.cn/1,4butynediol.htm \|title=1,4-Butynediol at Sanwei \|access-date=2006-11-11 \|archive-url=https://web.archive.org/web/20101204134416/http://www.swchemical.com.cn/1,4butynediol.htm \|archive-date=2010-12-04 \|url-status=dead }}</ref> It is also used for brightening, preserving, and inhibiting nickel plating.<ref name="Ullmann"/>

			It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO<sub>2</sub>CC(Cl)=C(Cl)CHO (see ]).
	==Safety==
⚫	1,4-Butynediol is corrosive and irritates the skin and ~~eyes.<ref~~ ~~name="NJ"/>~~

	==~~References~~==		== Safety ==
		⚫	1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.

			==See also==
			*] (but-2-ynedioic acid, 2-butynedioic acid)
			*]
			*] (but-2-yne)

			== References ==
	<references/>		<references/>

	{{DEFAULTSORT:~~Butynediol, 1,4-~~}}		{{DEFAULTSORT:Butynediol14}}
	]		]
	]		]

	]
	]
	]
	]
	]

Latest revision as of 21:35, 21 April 2024

1,4-Butynediol
Names


Preferred IUPAC name But-2-yne-1,4-diol
Other names Butynediol 2-Butyne-1,4-diol 1,4-Dihydroxy-2-butyne
Identifiers
CAS Number	110-65-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16413
ChEMBL	ChEMBL3187551
ChemSpider	7775
ECHA InfoCard	100.003.445
EC Number	203-788-6
KEGG	C02497
PubChem CID	8066
RTECS number	ES0525000
UNII	AXH202FPQM
UN number	2716
CompTox Dashboard (EPA)	DTXSID4021921
InChI InChI=1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2Key: DLDJFQGPPSQZKI-UHFFFAOYSA-N InChI=1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2Key: DLDJFQGPPSQZKI-UHFFFAOYAT
SMILES OCC#CCO
Properties
Chemical formula	C₄H₆O₂
Molar mass	86.090 g·mol
Appearance	Colorless crystalline solid
Density	1.11 g/cm (at 20 °C)
Melting point	58 °C (136 °F; 331 K)
Boiling point	238 °C (460 °F; 511 K)
Solubility in water	3740 g/L
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H314, H317, H331, H373
Precautionary statements	P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	~136 °C (277 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

1,4-Butynediol is an organic compound that is an alkyne and a diol. It is a colourless, hygroscopic solid that is soluble in water and polar organic solvents. It is a commercially significant compound in its own right and as a precursor to other products.

Synthesis

1,4-Butynediol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants:

2 CH₂O + HC≡CH → HOCH₂CCCH₂OH

Several patented production methods use copper bismuth catalysts coated on an inert material. The normal temperature range for the reaction is 90 °C up to 150 °C, depending on the pressure used for the reaction which can range from 1 to 20 bar.

Applications

1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes. It is the major raw material used in the synthesis of vitamin B₆. It is also used for brightening, preserving, and inhibiting nickel plating.

It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO₂CC(Cl)=C(Cl)CHO (see mucobromic acid).

Safety

1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.

References

1,4-Butynediol at chemicalland21.com
^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 978-3527306732.
Kale S. S.; Chaudhari R. V.; Ramachandran P. A. (1981). "Butynediol synthesis. A kinetic study". Industrial & Engineering Chemistry Product Research and Development. 20 (2): 309–315. doi:10.1021/i300002a015.
"1,4-Butynediol at Sanwei". Archived from the original on 2010-12-04. Retrieved 2006-11-11.

Categories:

Latest revision as of 21:35, 21 April 2024

Synthesis

Applications

Safety

See also

References