Difference between revisions of "Trimethyl borate"

From Sciencemadness Wiki
Jump to: navigation, search
 
(6 intermediate revisions by 2 users not shown)
Line 1: Line 1:
−
[[File:Trimethyl_borate.png|thumb]]
+
{{Chembox
−
'''Trimethyl borate''' is a boron tri[[ester]] consisting of a single [[boron]] atom bound to three [[methoxide]] groups. It is a volatile liquid that ignites easily to give a brilliant green flame, purer than one of barium or copper. It may be produced readily in large quantities.
+
| Name = Trimethyl borate
 +
| Reference =
 +
| IUPACName = Trimethyl borate
 +
| PIN =
 +
| SystematicName =
 +
| OtherNames = Boron trimethoxide<br>Trimethoxyborane<br>Trimethoxyboron
 +
<!-- Images -->
 +
| ImageFile =
 +
| ImageSize =
 +
| ImageAlt =
 +
| ImageName =
 +
| ImageFile1 = Trimethyl borate methanol azeotrope distilled by NurdRage.png
 +
| ImageSize1 = 300
 +
| ImageAlt1 =
 +
| ImageName1 =
 +
| ImageCaption1 = Azeotrope of 75% trimethyl borate and 25% methanol
 +
| ImageFile2 = Trimethyl_borate.png
 +
| ImageSize2 = 250
 +
| ImageAlt2 =
 +
| ImageName2 =
 +
| ImageCaption2 = Structure of the compound
 +
| ImageFile3 =
 +
| ImageSize3 =
 +
| ImageAlt3 =
 +
| ImageName3 =
 +
| ImageFileL1 =
 +
| ImageSizeL1 =
 +
| ImageAltL1 =
 +
| ImageNameL1 =
 +
| ImageFileR1 =
 +
| ImageSizeR1 =
 +
| ImageAltR1 =
 +
| ImageNameR1 =
 +
| ImageFileL2 =
 +
| ImageSizeL2 =
 +
| ImageAltL2 =
 +
| ImageNameL2 =
 +
| ImageFileR2 =
 +
| ImageSizeR2 =
 +
| ImageAltR2 =
 +
| ImageNameR2 =
 +
<!-- Sections -->
 +
| Section1 = {{Chembox Identifiers
 +
| 3DMet =
 +
| Abbreviations =
 +
| SMILES =
 +
  }}
 +
| Section2 = {{Chembox Properties
 +
| AtmosphericOHRateConstant =
 +
| Appearance = Colorless liquid
 +
| BoilingPt =
 +
| BoilingPtC = 68
 +
| BoilingPt_ref =
 +
| BoilingPt_notes =
 +
| Density = 0.932 g/cm<sup>3</sup>
 +
| Formula = C<sub>3</sub>H<sub>9</sub>BO<sub>3</sub>
 +
| HenryConstant =
 +
| LogP = -1.9
 +
| MolarMass = 103.91 g/mol
 +
| MeltingPt =
 +
| MeltingPtC = −34
 +
| MeltingPt_ref =
 +
| MeltingPt_notes =
 +
| pKa =
 +
| pKb =
 +
| Solubility = Reacts
 +
| SolubleOther = Reacts with [[carboxylic acid]]s<br>Miscible with [[acetone]], [[diethyl ether]], [[ethanol]], [[heptane]], [[hexane]], [[isopropanol]], [[isopropylamine]], [[methanol]], [[mineral oil]], [[tetrahydrofuran|THF]]
 +
| Solvent =
 +
| VaporPressure = 137 mmHg at 25 °C
 +
  }}
 +
| Section3 = {{Chembox Structure
 +
| Coordination =
 +
| CrystalStruct =
 +
| MolShape =
 +
  }}
 +
| Section4 = {{Chembox Thermochemistry
 +
| DeltaGf =
 +
| DeltaHc =
 +
| DeltaHf =
 +
| Entropy =
 +
| HeatCapacity =
 +
  }}
 +
| Section5 = {{Chembox Explosive
 +
| ShockSens =
 +
| FrictionSens =
 +
| DetonationV =
 +
| REFactor =
 +
  }}
 +
| Section6 = {{Chembox Hazards
 +
| AutoignitionPt = 308 °C
 +
| ExploLimits =
 +
| ExternalMSDS = [https://www.docdroid.net/HVGtXYZ/trimethyl-borate-sa.pdf.html Sigma-Aldrich]
 +
| FlashPt = -8 °C
 +
| LD50 = 6.140 mg/kg (rat, oral)<br>1.845 mg/kg (rabbit, dermal)
 +
| LC50 =
 +
| MainHazards = Flammable
 +
| NFPA-F =
 +
| NFPA-H =
 +
| NFPA-R =
 +
| NFPA-S =
 +
  }}
 +
| Section7 = {{Chembox Related
 +
| OtherAnions =
 +
| OtherCations =
 +
| OtherFunction =
 +
| OtherFunction_label =
 +
| OtherCompounds = [[Triethyl borate]]
 +
  }}
 +
}}
 +
'''Trimethyl borate''' is a boron tri[[ester]] consisting of a single [[boron]] atom bound to three [[methoxide]] groups. It is a volatile liquid that ignites easily to give a brilliant green flame, purer than that of [[barium]]. It may be produced readily in large quantities.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
Trimethyl borate, being produced by dehydration, decomposes into [[methanol]] and [[boric acid]] on exposure to water. It is a reducing agent and burns in the presence of oxygen to form [[boron trioxide]]. In flames, it emits a brilliant green color that overpowers many other flame colors, as evidenced here.
+
Trimethyl borate, being produced by dehydration, decomposes into [[methanol]] and [[boric acid]] on exposure to water. It burns in the presence of oxygen to form [[boron trioxide]]. In flames, it emits a brilliant green color that overpowers many other flame colors, as evidenced here.
  
 
[[File:Trimethyl borate igniting in a volumetric flask|thumb|right|335 px]]
 
[[File:Trimethyl borate igniting in a volumetric flask|thumb|right|335 px]]
  
 
===Physical===
 
===Physical===
−
Trimethyl borate is a colorless liquid at room temperature, that evaporates easily. It has a melting point of −34 °C and boils at 68 °C. It will decompose in water.
+
Trimethyl borate is a colorless liquid at room temperature, that evaporates easily. It has a melting point of −34 °C and boils at 68 °C. It will decompose in water and acids.
  
 
==Availability==
 
==Availability==
Line 15: Line 124:
  
 
==Preparation==
 
==Preparation==
−
Trimethyl borate can be produced by adding an excess of dry [[methanol]] to [[boric acid]] or, preferably, [[Boron trioxide|boric oxide]], with a small amount of [[sulfuric acid]] and/or some heating to dehydrate the mixture if needed.
+
Trimethyl borate can be produced by adding an excess of dry [[methanol]] to [[boric acid]] or, preferably, [[Boron trioxide|boric oxide]], with a small amount of [[sulfuric acid]] and/or some heating to dehydrate the mixture if needed. Since an excess of methanol is used, the final product will be an azeotropic mixture of methanol (25%) and trimethyl borate (75%). It's possible to obtain pure trimethyl borate by turning the methanol into trimethyl borate using a boron trihalide, such as boron tribromide. However, the trihalide should be added slowly to prevent the already present boron tribromide from hydrolyzing.
  
 
==Projects==
 
==Projects==
Line 30: Line 139:
 
===Disposal===
 
===Disposal===
 
Trimethyl borate can be safely burned. It will hydrolyze in water to yield methanol and boric acid, which can be safely disposed of.
 
Trimethyl borate can be safely burned. It will hydrolyze in water to yield methanol and boric acid, which can be safely disposed of.
 +
 +
==Gallery==
 +
<gallery widths="200" position="center" columns="4" orientation="none">
 +
Trimethyl_borate_methanol_azeotrope.jpg|Trimethyl borate as the methanol azeotrope
 +
Trimethyl_borate_flame.jpg|Flame color of trimethyl borate
 +
</gallery>
  
 
==See also==
 
==See also==
Line 50: Line 165:
 
[[Category:Materials that react with water]]
 
[[Category:Materials that react with water]]
 
[[Category:Easily prepared chemicals]]
 
[[Category:Easily prepared chemicals]]
 +
[[Category:Liquids]]

Latest revision as of 19:50, 9 September 2021

Trimethyl borate
Trimethyl borate methanol azeotrope distilled by NurdRage.png
Azeotrope of 75% trimethyl borate and 25% methanol
Trimethyl borate.png
Structure of the compound
Names
IUPAC name
Trimethyl borate
Other names
Boron trimethoxide
Trimethoxyborane
Trimethoxyboron
Properties
C3H9BO3
Molar mass 103.91 g/mol
Appearance Colorless liquid
Density 0.932 g/cm3
Melting point −34 °C (−29 °F; 239 K)
Boiling point 68 °C (154 °F; 341 K)
Reacts
Solubility Reacts with carboxylic acids
Miscible with acetone, diethyl ether, ethanol, heptane, hexane, isopropanol, isopropylamine, methanol, mineral oil, THF
Vapor pressure 137 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point -8 °C
Lethal dose or concentration (LD, LC):
6.140 mg/kg (rat, oral)
1.845 mg/kg (rabbit, dermal)
Related compounds
Related compounds
 Triethyl borate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethyl borate is a boron triester consisting of a single boron atom bound to three methoxide groups. It is a volatile liquid that ignites easily to give a brilliant green flame, purer than that of barium. It may be produced readily in large quantities.

Properties

Chemical

Trimethyl borate, being produced by dehydration, decomposes into methanol and boric acid on exposure to water. It burns in the presence of oxygen to form boron trioxide. In flames, it emits a brilliant green color that overpowers many other flame colors, as evidenced here.

File:Trimethyl borate igniting in a volumetric flask
335 px

Physical

Trimethyl borate is a colorless liquid at room temperature, that evaporates easily. It has a melting point of −34 °C and boils at 68 °C. It will decompose in water and acids.

Availability

Relatively pure trimethyl borate can be bought from only a few chemical suppliers as it has few commercial applications. It is by far cheaper and more practical to produce it.

Preparation

Trimethyl borate can be produced by adding an excess of dry methanol to boric acid or, preferably, boric oxide, with a small amount of sulfuric acid and/or some heating to dehydrate the mixture if needed. Since an excess of methanol is used, the final product will be an azeotropic mixture of methanol (25%) and trimethyl borate (75%). It's possible to obtain pure trimethyl borate by turning the methanol into trimethyl borate using a boron trihalide, such as boron tribromide. However, the trihalide should be added slowly to prevent the already present boron tribromide from hydrolyzing.

Projects

Handling

Safety

There is little data on the toxicity of trimethyl borate. Nevertheless, it is a good idea not to consume or inhale it, and its hydrolysis products aren't exactly healthy. Keep away from open flame. Water may be used to put out trimethyl borate flames. When igniting trimethyl borate, goggles should be worn to prevent boric oxide dust from irritating the eyes.

Storage

Trimethyl borate should only be stored in closed bottles, away from light or any heat source. Since it is sensitive to water, it's best to keep the bottle airtight or put it into a desiccator.

Disposal

Trimethyl borate can be safely burned. It will hydrolyze in water to yield methanol and boric acid, which can be safely disposed of.

Gallery

  • Trimethyl borate as the methanol azeotrope

  • Flame color of trimethyl borate

See also

References

Relevant Sciencemadness threads

Retrieved from "https://www.sciencemadness.org/smwiki/index.php?title=Trimethyl_borate&oldid=14070"