Trimethylsilanol

TMS is a contaminant in the atmospheres of spacecraft, where it arises from the degradation of silicone-based materials.[http://books.nap.edu/openbook.php?record_id=9062&page=177 Trimethylsilanol], Harold L. Kaplan, Martin E. Coleman, John T. James: Spacecraft Maximum Allowable Concentrations for Selected Airborne Contaminants, Volume 1 (1994). Specifically, it is the volatile product from the hydrolysis of polydimethylsiloxane, which are generally terminated with trimethylsilyl groups:

:{{chem2|(CH3)3SiO[Si(CH3)2O]_{n}R + H2O → (CH3)3SiOH + HO[Si(CH3)2O]_{n}R}}

TMS and related volatile siloxanes are formed by hydrolysis of silicones-based containing materials, which are found in detergents and cosmetic products.

Traces of trimethylsilanol, together with other volatile siloxanes, are present in biogas and landfill gas, again resulting from the degradation of silicones. As their combustion forms particles of silicates and microcrystalline quartz, which cause abrasion of combustion engine parts, they pose problems for the use of such gases in combustion engines.http://epics.ecn.purdue.edu/bgi/Documents/Fall%25202009/Removal_of_Siloxanes_.pdf {{dead link|date=July 2015}}

Trimethylsilanol cannot be produced by simple hydrolysis of chlorotrimethylsilane as this reaction leads to the etherification product hexamethyldisiloxane, because of the by-product hydrochloric acid.Didier Astruc: Organometallic Chemistry and Catalysis. Springer Science & Business Media, 2007, {{ISBN|978-3-540-46129-6}}, S. 331 ({{Google books|aVyfo52-nRsC||page=331}}).$$\backslash ce\{2ClSi(CH3)3\; ->[\{\}\backslash atop\backslash ce\{+H2O,\; -HCl\}]\}\; \backslash ce\{2HOSi(CH3)3\; ->[\{\}\backslash atop\backslash ce\{-H2O\}]\; (CH3)3Si-O-Si(CH3)3\}$$

Trimethylsilanol is accessible by weakly basic hydrolysis of chlorotrimethylsilane, since the dimerization can thus be avoided.J.A. Cella, J.C. Carpenter: Procedures for the preparation of silanols in J. Organomet. Chem. 480 (1994), 23–23; {{doi|10.1016/0022-328X(94)87098-5}} Trimethylsilanol can also be obtained by the basic hydrolysis of hexamethyldisiloxane.M. Lovric, I. Cepanec, M. Litvic, A. Bartolincic, V. Vinkovic: Croatia Chem. Acta 80 (2007), 109–115

Trimethylsilanol is a weak acid with a pK_a value of 11.T. Kagiya, Y. Sumida, T. Tachi: An Infrared Spectroscopic Study of hydrogen Bonding Interaction. Structural Studies of Proton-donating and -accepting Powers in Bull. Chem. Soc. Jpn. 43 (1970), 3716–3722. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol (pK_a 19). Deprotonation with sodium hydroxide gives sodium trimethylsiloxide.

TMS reacts with the silanols ({{chem2|R3SiOH}}) giving silyl ethers.

In terms of its structure, the molecule is tetrahedral. The compound forms monoclinic crystals.R. Minkwitz, S. Schneider: Die Tieftemperaturkristallstruktur von Trimethylsilanol. In: Zeitschrift für Naturforschung B. 53, 1998, S. 426–429 ([http://zfn.mpdl.mpg.de/data/Reihe_B/53/ZNB-1998-53b-0426.pdf PDF], freier Volltext).

The heat of evaporation is 45.64 kJ·mol⁻¹, the evaporation entropy 123 J·K⁻¹·mol⁻¹. The vapor pressure function according to Antoine is obtained as log₁₀(P/1{{nbsp}}bar) = A − B/(T + C) (P in bar, T in K) with A = 5.44591, B = 1767.766{{nbsp}}K and C = −44.888{{nbsp}}K in a temperature range from 291{{nbsp}}K to 358{{nbsp}}K. Below the melting point at −4.5 °C,Batuew et al. in Doklady Akademii Nauk SSSR 95 (1954) 531. The ¹H NMR in CDCl₃ shows a singlet at δ=0.14 ppm.{{cite journal |last1=Hamada |first1=Tomoaki |last2=Manabe |first2=Kai |last3=Kobayashi |first3=Shū |date=13 January 2006 |title=Catalytic Asymmetric Mannich-Type Reactions Activated by ZnF2 Chiral Diamine in Aqueous Media |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.200500673 |journal=Chemistry - A European Journal |volume=12 |issue=4 |pages=1205–1215 |doi=10.1002/chem.200500673 |pmid=16267871 |access-date=16 March 2021}}

Like other silanols, trimethylsilanol exhibits antimicrobial properties.{{cite journal| journal=Electronic Journal of Biotechnology |volume= 9 |issue= 2 |year=2006 |title=Silanol – A novel class of antimicrobial agent |author=Yun-mi Kim, Samuel Farrah, Ronald H. Baney |url=http://www.ejbiotechnology.info/content/vol9/issue2/full/4/index.html |doi=10.2225/vol9-issue2-fulltext-4 |pages=176–180|doi-broken-date= 14 May 2025 }}

Category:Silanols

Category:Trimethylsilyl compounds