Dibutyltin dilaurate

Dibutyltin dilaurate
Names
	IUPAC name [Dibutyl(dodecanoyloxy)stannyl] dodecanoate
	Other names Butynorate; Davainex; DBTDL; DBTL; Dibutylbis(lauroyloxy)tin; Dibutylstannylene dilaurate; Dibutyltin didodecanoate; Dibutyltindilaurate; Lauric acid, 1,1'-(dibutylstannylene) ester; Stabilizer D-22; T 12 (catalyst); Tinostat;
Identifiers
CAS Number	77-58-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106564;
ECHA InfoCard	100.000.946
EC Number	201-039-8;
PubChem CID	16682738;
RTECS number	WH7000000;
UNII	L4061GMT90 ;
UN number	3146
CompTox Dashboard (EPA)	DTXSID6024961 ;
	InChI InChI=1S/2C12H24O2.2C4H9.Sn/c21-2-3-4-5-6-7-8-9-10-11-12(13)14;21-3-4-2;/h22-11H2,1H3,(H,13,14);21,3-4H2,2H3;/q;;;;+2/p-2 Key: UKLDJPRMSDWDSL-UHFFFAOYSA-L; InChI=1/2C12H24O2.2C4H9.Sn/c21-2-3-4-5-6-7-8-9-10-11-12(13)14;21-3-4-2;/h22-11H2,1H3,(H,13,14);21,3-4H2,2H3;/q;;;;+2/p-2/rC32H64O4Sn/c1-5-9-13-15-17-19-21-23-25-27-31(33)35-37(29-11-7-3,30-12-8-4)36-32(34)28-26-24-22-20-18-16-14-10-6-2/h5-30H2,1-4H3 Key: UKLDJPRMSDWDSL-PFKFAYPQAT;
	SMILES CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC;
Properties
Chemical formula	(CH3(CH2)10CO2)2Sn((CH2)3CH3)2
Molar mass	631.570 g·mol−1
Appearance	Colourless oily liquid or soft waxy crystals
Odor	Fatty
Density	1.066 g/cm3
Melting point	22 to 24 °C (72 to 75 °F; 295 to 297 K)
Boiling point	205 °C at 1.3 kPa
Solubility in water	Practically insoluble (less than 1 mg/mL at 68 °F (20 °C))
Solubility	Practically insoluble in methanol; Soluble in petroleum ether, benzene, acetone, ether, carbon tetrachloride, organic esters
Vapor pressure	<0.01 hPa (0.2 mmHg at 160 °C)
Refractive index (nD)	1.4683 at 20 °C (for light at wavelength of 589.29 nm)
Viscosity	42 cP
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H341, H360FD, H372
Precautionary statements	P260, P264, P270, P280, P281, P319, P405, P501
Flash point	191 °C
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	175 mg/kg (oral, rat); 33 mg/kg (intravenous, rat); 210 mg/kg (oral, mouse); 100 mg/kg (oral, rabbit);
LC50 (median concentration)	150 mg/m3 (inhalation, mouse, 2 hours)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dibutyltin dilaurate (abbreviated DBTDL) is an organotin compound with the formula (CH₃(CH₂)₁₀CO₂)₂Sn((CH₂)₃CH₃)₂. It is a colorless viscous and oily liquid. It is used as a catalyst .

Description edit

In terms of its structure, the molecule of dibutyltin dilaurate consists of two laurate groups and two butyl groups attached to a tin(IV) atom. The molecular geometry at tin is tetrahedral. Based on the crystal structure of the related bis(bromobenzoate), the oxygen atoms of the carbonyl groups are weakly bonded to tin atom.^[3]

Decomposition edit

Upon heating to decomposition temperature (which is above 250 °C^[2]), dibutyltin dilaurate emits acrid smoke and fumes.^[1]

Uses edit

Dibutyltin dilaurate is used as a paint additive.^[1] Together with dibutyltin dioctanoate, dibutyltin dilaurate is used as a catalyst for polyurethane production from isocyanates and diols. It is also useful as a catalyst for transesterification and for the room temperature vulcanization of silicones. It is also used as a stabilizer in polyvinyl chloride,^[4]^[1] vinyl ester resins, lacquers, and elastomers.^[1] It is also added to animal feed to remove cecal worms, roundworms, and tapeworms in chickens and turkeys and to prevent or provide treatment against hexamitosis and coccidiosis.^[5]

Hazards and toxicity edit

Dibutyltin dilaurate can be absorbed through the skin. It irritates skin and eyes (causes redness of skin and eyes). It is a neurotoxin. It can cause injuries to the liver, kidneys, and gastrointestinal tract. The symptoms of poisoning with dibutyltin dilaurate include nausea, headache, muscular weakness and even paralysis. Dibutyltin dilaurate is combustible.^[1] Its vapor is denser than air (21.8 times denser than air^[1]), so it can spread on the floors, forming explosive mixtures with air. On fire, it emits irritating and toxic fumes and smoke which contain tin, tin oxides and carbon oxides.^[2] Dibutyltin dilaurate is very reactive with acids and oxidizers.^[1]

Related compounds edit

Dibutyltin dioctanoate: CAS#4731-77-5
Dibutyltin diacetate: CAS #1067-33-0

References edit

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x ^y ^z "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b ^c ^d ^e "Dibutyltin dilaurate 95 77-58-7".
^ Weng Ng, Seik; Das, V. G. Kumar; Yip, Wai-Hing; Wang, Ru-Ji; Mak, Thomas C. W. (1990-08-28). "Di-n-butyltin(IV) di-o-bromobenzoate, a weakly-bridged dimer". Journal of Organometallic Chemistry. 393 (2): 201–204. doi:10.1016/0022-328X(90)80199-A. ISSN 0022-328X.
^ Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1.
^ PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.

[pubchem-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x ^y ^z "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.

[sigmaaldrich-2] "Dibutyltin dilaurate 95 77-58-7".

[3] Weng Ng, Seik; Das, V. G. Kumar; Yip, Wai-Hing; Wang, Ru-Ji; Mak, Thomas C. W. (1990-08-28). "Di-n-butyltin(IV) di-o-bromobenzoate, a weakly-bridged dimer". Journal of Organometallic Chemistry. 393 (2): 201–204. doi:10.1016/0022-328X(90)80199-A. ISSN 0022-328X.

[4] Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1.

[5] PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.

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[2]

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[4]

[5]

Names

IUPAC name [Dibutyl(dodecanoyloxy)stannyl] dodecanoate
Other names Butynorate Davainex^[1] DBTDL DBTL^[1] Dibutylbis(lauroyloxy)tin^[1] Dibutylstannylene dilaurate^[1] Dibutyltin didodecanoate^[1] Dibutyltindilaurate Lauric acid, 1,1'-(dibutylstannylene) ester^[1] Stabilizer D-22^[1] T 12 (catalyst)^[1] Tinostat^[1]
Identifiers
CAS Number	77-58-7^Y
3D model (JSmol)	Interactive image
ChemSpider	21106564
ECHA InfoCard	100.000.946
EC Number	201-039-8
PubChem CID	16682738
RTECS number	WH7000000
UNII	L4061GMT90^Y
UN number	3146
CompTox Dashboard (EPA)	DTXSID6024961
InChI InChI=1S/2C12H24O2.2C4H9.Sn/c21-2-3-4-5-6-7-8-9-10-11-12(13)14;21-3-4-2;/h22-11H2,1H3,(H,13,14);21,3-4H2,2H3;/q;;;;+2/p-2 Key: UKLDJPRMSDWDSL-UHFFFAOYSA-L InChI=1/2C12H24O2.2C4H9.Sn/c21-2-3-4-5-6-7-8-9-10-11-12(13)14;21-3-4-2;/h22-11H2,1H3,(H,13,14);21,3-4H2,2H3;/q;;;;+2/p-2/rC32H64O4Sn/c1-5-9-13-15-17-19-21-23-25-27-31(33)35-37(29-11-7-3,30-12-8-4)36-32(34)28-26-24-22-20-18-16-14-10-6-2/h5-30H2,1-4H3 Key: UKLDJPRMSDWDSL-PFKFAYPQAT
SMILES CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC
Properties
Chemical formula	(CH₃(CH₂)₁₀CO₂)₂Sn((CH₂)₃CH₃)₂
Molar mass	631.570 g·mol⁻¹
Appearance	Colourless oily liquid or soft waxy crystals
Odor	Fatty^[2]
Density	1.066 g/cm³
Melting point	22 to 24 °C (72 to 75 °F; 295 to 297 K) ^[1]
Boiling point	205 °C at 1.3 kPa^[1]^[2]
Solubility in water	Practically insoluble (less than 1 mg/mL at 68 °F (20 °C))^[1]
Solubility	Practically insoluble in methanol Soluble in petroleum ether, benzene, acetone, ether, carbon tetrachloride, organic esters
Vapor pressure	<0.01 hPa (0.2 mmHg at 160 °C)^[2]
Refractive index (n_D)	1.4683 at 20 °C (for light at wavelength of 589.29 nm)^[1]
Viscosity	42 cP^[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H341, H360FD, H372^[1]
Precautionary statements	P260, P264, P270, P280, P281, P319, P405, P501^[1]
Flash point	191 °C^[1]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	175 mg/kg (oral, rat) 33 mg/kg (intravenous, rat) 210 mg/kg (oral, mouse) 100 mg/kg (oral, rabbit) ^[1]
LC₅₀ (median concentration)	150 mg/m³ (inhalation, mouse, 2 hours)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references