Dibutyltin dilaurate

Last updated
Dibutyltin dilaurate
Dibutyltin dilaurate molecule structure.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.946 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-039-8
PubChem CID
RTECS number
  • WH7000000
UNII
UN number 3146
  • InChI=1S/2C12H24O2.2C4H9.Sn/c2*1-2-3-4-5-6-7-8-9-10-11-12(13)14;2*1-3-4-2;/h2*2-11H2,1H3,(H,13,14);2*1,3-4H2,2H3;/q;;;;+2/p-2
    Key: UKLDJPRMSDWDSL-UHFFFAOYSA-L
  • InChI=1/2C12H24O2.2C4H9.Sn/c2*1-2-3-4-5-6-7-8-9-10-11-12(13)14;2*1-3-4-2;/h2*2-11H2,1H3,(H,13,14);2*1,3-4H2,2H3;/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
  • CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC
Properties
(CH3(CH2)10CO2)2Sn((CH2)3CH3)2
Molar mass 631.570 g·mol−1
AppearanceColourless oily liquid or soft waxy crystals
Odor Fatty [2]
Density 1.066 g/cm3 [2]
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]
Practically insoluble (0.00143 g/l at 68 °F (20 °C)) [1] [2]
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 25 °C) [2]
1.4683 at 20 °C (for light at wavelength of 589.29 nm) [1]
Viscosity 42 cP [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very toxic, very flammable, causes serious injuries to skin, eyes, thymus, lungs and other organs. Can cause paralysis.
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H317, H319, H341, H360, H360FD, H370, H372, H410 [1] [2]
P201, P202, P260, P264, P270, P272, P273, P280, P281, P302+P352, P305+P351+P338, P307+P311, P319, P333+P313, P337+P313, P363, P391, P405, P501 [1] [2]
Flash point 191 °C [1]
Lethal dose or concentration (LD, LC):
  • 175 mg/kg (oral, rat)
  • 33 mg/kg (intravenous, rat)
  • 210 mg/kg (oral, mouse)
  • 100 mg/kg (oral, rabbit)
[1]
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).

Dibutyltin dilaurate (abbreviated DBTDL) is an organotin compound with the formula (C H 3(CH2)10CO 2)2 Sn(CH2CH2CH2CH3)2. It is a colorless viscous and oily liquid. It is used as a catalyst.

Contents

Description

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] According to some authors, this compound is a dibutyltin(IV) ester of lauric acid. [1] [4]

Decomposition

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

Uses

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, [5] [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. [6]

Hazards and toxicity

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 very reactive with acids and oxidizers, and it is combustible. [1] It emits irritating and toxic fumes and smoke when burned, which contain tin, tin oxides and carbon oxides. [2] Moreover, its vapor is much denser than air (21.8 times so [1] ), so it can spread on floors, resulting in explosive conditions or asphyxiation hazards.

Related Research Articles

Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. It was first discovered by Andreas Libavius (1550–1616) and was known as spiritus fumans libavii.

<span class="mw-page-title-main">Cyclohexyl nitrite</span> Chemical compound

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<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

<span class="mw-page-title-main">Phosphorous acid</span> Chemical compound (H3PO3)

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<span class="mw-page-title-main">Rhenium(VII) oxide</span> Chemical compound

Rhenium(VII) oxide is the inorganic compound with the formula Re2O7. This yellowish solid is the anhydride of HOReO3. Perrhenic acid, Re2O7·2H2O, is closely related to Re2O7. Re2O7 is the raw material for all rhenium compounds, being the volatile fraction obtained upon roasting the host ore.

<span class="mw-page-title-main">Tungsten(VI) oxytetrachloride</span> Chemical compound

Tungsten(VI) oxytetrachloride is the inorganic compound with the formula WOCl4. This diamagnetic solid is used to prepare other complexes of tungsten. The red crystalline compound is soluble in nonpolar solvents but it reacts with alcohols and water and forms adducts with Lewis bases.

Tin(II) bromide is a chemical compound of tin and bromine with a chemical formula of SnBr2. Tin is in the +2 oxidation state. The stability of tin compounds in this oxidation state is attributed to the inert pair effect.

<span class="mw-page-title-main">Tetrafluorohydrazine</span> Chemical compound

Tetrafluorohydrazine or perfluorohydrazine, N2F4, is a colourless, nonflammable, reactive inorganic gas. It is a fluorinated analog of hydrazine.

<span class="mw-page-title-main">Trimethyltin chloride</span> Chemical compound

Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.

<span class="mw-page-title-main">Dibutyltin oxide</span> Chemical compound

Dibutyltin oxide, or dibutyloxotin, is an organotin compound with the chemical formula (C4H9)2SnO. It is a colorless solid that, when pure, is insoluble in organic solvents. It is used as a reagent and a catalyst.

<span class="mw-page-title-main">Methanetetracarboxylate</span> Ion

In chemistry, methanetetracarboxylate is a tetravalent anion with formula C5O4−8 or C(−CO−2)4. It has four carboxylate groups attached to a central carbon atom; so it has the same carbon backbone as neopentane. It is an oxocarbon anion, that is, consists only of carbon and oxygen.

<span class="mw-page-title-main">Stannole</span> Organotin compound

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<span class="mw-page-title-main">Tetravinyltin</span> Chemical compound

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<span class="mw-page-title-main">Dipropyltin dichloride</span> Organotin compound

Dipropyltin dichloride is an organotin compound with the chemical formula (CH3CH2CH2)2SnCl2. It is a white solid. This chemical belongs to a subclass of organotin compounds called diorganotin dihalides.

<i>S</i>,<i>S</i>-Dimethyl dithiocarbonate Chemical compound

S,S'-Dimethyl dithiocarbonate is an organic compound with the chemical formula OC(SCH3)2. It is a colorless liquid. It is a methyl ester of dithiocarbonic S,S-acid. It is a thioester. It is an analog of dimethyl carbonate, where the two oxygen atoms from the −OCH3 groups are replaced by sulfur atoms. In terms of the name of this thioester, it is derived from an esterification of dithiocarbonic S,S-acid with methanethiol.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 3 4 5 6 7 8 9 https://www.sigmaaldrich.com/US/en/sds/aldrich/291234?userType=anonymous [ bare URL ]
  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. ↑ "Trimethyltin acetate | C5H12O2Sn | ChemSpider".
  5. ↑ Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN   3-527-31023-1.
  6. ↑ PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.
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