Sciencemadness Wiki - User contributions [en]

Talk:Trimethyl phosphate

2020-12-22T21:10:24Z

Draeger: Added new discussion

== Unfinished safety section ==
There seems to be something missing in the safety section. In the last sentence, it says: "Being non-volatile" and nothing more. How could the sentence be continued, or should it be removed?
--[[User:Draeger|Draeger]] ([[User talk:Draeger|talk]]) 21:10, 22 December 2020 (UTC)

Iodine

2020-12-20T20:16:15Z

Draeger: Fixed group, made astatine a link

{{Infobox element

|image name=Iodine vapors hotplate.jpg
|image alt=
|image size=300
|image name comment=Iodine sublimating in a fume hood.
|image name 2=
|image alt 2=
|image size 2=
|image name 2 comment=

|name=Iodine
|symbol=I
|pronounce=
|pronounce ref=
|pronounce comment=
|pronounce 2=
|alt name=
|alt names=
|allotropes=
|appearance=Lustrous metallic gray (solid) Violet (gas)

|above=[[Bromine|Br]]
|below=[[Astatine]]
|left=[[Tellurium]]
|right=[[Xenon]]
|number=53
|atomic mass=126.90447(3)
|atomic mass 2=
|atomic mass ref=
|atomic mass comment=
|series=
|series ref=
|series comment=
|series color=
|group=17
|group ref=
|group comment=17
|period=5
|period ref=
|period comment=
|block=p
|block ref=
|block comment=
|electron configuration=[Kr] 4d10 5s2 5p5
|electron configuration ref=
|electron configuration comment=
|electrons per shell=2, 8, 18, 18, 7
|electrons per shell ref=
|electrons per shell comment=

|physical properties comment=
|color=Metallic gray
|phase=Solid
|phase ref=
|phase comment=
|melting point K=386.85
|melting point C=113.7
|melting point F=236.66
|melting point ref=
|melting point comment=
|boiling point K=457.4
|boiling point C=184.3
|boiling point F=363.7
|boiling point ref=
|boiling point comment=
|sublimation point K=
|sublimation point C=
|sublimation point F=
|sublimation point ref=
|sublimation point comment=
|density gplstp=
|density gplstp ref=
|density gplstp comment=
|density gpcm3nrt=4.933
|density gpcm3nrt ref=
|density gpcm3nrt comment=
|density gpcm3nrt 2=
|density gpcm3nrt 2 ref=
|density gpcm3nrt 2 comment=
|density gpcm3nrt 3=
|density gpcm3nrt 3 ref=
|density gpcm3nrt 3 comment=
|density gpcm3mp=
|density gpcm3mp ref=
|density gpcm3mp comment=
|density gpcm3bp=
|density gpcm3bp ref=
|density gpcm3bp comment=
|molar volume=
|molar volume unit =
|molar volume ref=
|molar volume comment=
|triple point K=386.65
|triple point kPa=12.1
|triple point ref=
|triple point comment=
|triple point K 2=
|triple point kPa 2=
|triple point 2 ref=
|triple point 2 comment=
|critical point K=819
|critical point MPa=11.7
|critical point ref=
|critical point comment=
|heat fusion=15.52
|heat fusion ref=
|heat fusion comment=
|heat fusion 2=
|heat fusion 2 ref=
|heat fusion 2 comment=
|heat vaporization=41.57
|heat vaporization ref=
|heat vaporization comment=
|heat capacity=54.44
|heat capacity ref=
|heat capacity comment=
|heat capacity 2=
|heat capacity 2 ref=
|heat capacity 2 comment=
|vapor pressure 1=260
|vapor pressure 10=282
|vapor pressure 100=309
|vapor pressure 1 k=342
|vapor pressure 10 k=381
|vapor pressure 100 k=457
|vapor pressure ref=
|vapor pressure comment=
|vapor pressure 1 2=
|vapor pressure 10 2=
|vapor pressure 100 2=
|vapor pressure 1 k 2=
|vapor pressure 10 k 2=
|vapor pressure 100 k 2=
|vapor pressure 2 ref=
|vapor pressure 2 comment=

|atomic properties comment=
|oxidation states=7, 6, 5, 4, 3, 1, −1
|oxidation states ref=
|oxidation states comment=(a strongly acidic oxide)
|electronegativity=2.66
|electronegativity ref=
|electronegativity comment=
|ionization energy 1=1008.4
|ionization energy 1 ref=
|ionization energy 1 comment=
|ionization energy 2=1845.9
|ionization energy 2 ref=
|ionization energy 2 comment=
|ionization energy 3=3180
|ionization energy 3 ref=
|ionization energy 3 comment=
|number of ionization energies=
|ionization energy ref=
|ionization energy comment=
|atomic radius=140
|atomic radius ref=
|atomic radius comment=
|atomic radius calculated=
|atomic radius calculated ref=
|atomic radius calculated comment=
|covalent radius=139±3
|covalent radius ref=
|covalent radius comment=
|Van der Waals radius=198
|Van der Waals radius ref=
|Van der Waals radius comment=

|crystal structure=
|crystal structure prefix=
|crystal structure ref=
|crystal structure comment= Orthorhombic
|crystal structure 2=
|crystal structure 2 prefix=
|crystal structure 2 ref=
|crystal structure 2 comment=
|speed of sound=
|speed of sound ref=
|speed of sound comment=
|speed of sound rod at 20=
|speed of sound rod at 20 ref=
|speed of sound rod at 20 comment=
|speed of sound rod at r.t.=
|speed of sound rod at r.t. ref=
|speed of sound rod at r.t. comment=
|thermal expansion=
|thermal expansion ref=
|thermal expansion comment=
|thermal expansion at 25=
|thermal expansion at 25 ref=
|thermal expansion at 25 comment=
|thermal conductivity=0.449
|thermal conductivity ref=
|thermal conductivity comment=
|thermal conductivity 2=
|thermal conductivity 2 ref=
|thermal conductivity 2 comment=
|thermal diffusivity=
|thermal diffusivity ref=
|thermal diffusivity comment=
|electrical resistivity=1.3×107
|electrical resistivity unit prefix=
|electrical resistivity ref=
|electrical resistivity comment=
|electrical resistivity at 0=
|electrical resistivity at 0 ref=
|electrical resistivity at 0 comment=
|electrical resistivity at 20=
|electrical resistivity at 20 ref=
|electrical resistivity at 20 comment=
|band gap=
|band gap ref=
|band gap comment=
|Curie point K=
|Curie point ref=
|Curie point comment=
|magnetic ordering=Diamagnetic
|magnetic ordering ref=
|magnetic ordering comment=
|tensile strength=
|tensile strength ref=
|tensile strength comment=
|Young's modulus=
|Young's modulus ref=
|Young's modulus comment=
|Shear modulus=
|Shear modulus ref=
|Shear modulus comment=
|Bulk modulus=7.7
|Bulk modulus ref=
|Bulk modulus comment=
|Poisson ratio=
|Poisson ratio ref=
|Poisson ratio comment=
|Mohs hardness=
|Mohs hardness ref=
|Mohs hardness comment=
|Mohs hardness 2=
|Mohs hardness 2 ref=
|Mohs hardness 2 comment=
|Vickers hardness=
|Vickers hardness ref=
|Vickers hardness comment=
|Brinell hardness=
|Brinell hardness ref=
|Brinell hardness comment=
|CAS number=7553-56-2
|CAS number ref=
|CAS number comment=

|naming=
|predicted by=
|prediction date ref=
|prediction date=
|discovered by=
|discovery date ref=
|discovery date=
|first isolation by=
|first isolation date ref=
|first isolation date=
|discovery and first isolation by=Bernard Courtois (1811)
|named by=
|named date ref=
|named date=
|history comment label=
|history comment=

|isotopes=
|isotopes comment=
|engvar=
}}
'''Iodine''' is the element with the symbol '''I''' and atomic number 53. It is a reactive [[halogen]] which is volatile and has many uses in inorganic and organic chemistry.

Unlike the other halogens, iodine is solid at standard conditions and does not sublime rapidly, thus can be handled much safer.

==Properties==
===Physical===
[[File:Iodine beaker.jpg|thumb|300px|Metallic crystals of iodine encrusting the inside of a beaker.]]
Iodine can be seen in the form of royal dark purple crystals, or in a gas in a lighter color. It is most commonly found as a silvery metallic looking chemical. Iodine, like other halogens, has its own unique smell, somewhat similar to [[chlorine]], or described as being "clean". Contrary to some sources, iodine will melt if heated, though it tends to sublime a lot. This can be done very easy by using high heat or hot concentrated [[sulfuric acid]].

===Chemical===
Iodine is not very soluble in water, but is very soluble in a solution of sodium or [[potassium iodide]] in water. When dissolved like this, the solution has a color from light yellow to dark orange, to almost black brown. This change in color and solubility is due to the formation of the triiodide(I3-) ion. If reacted while in water with a sufficient reducing agent, such as [[phosphorus]] or [[hydrogen sulfide]], iodine is converted to hydrogen iodide, which dissolves in solution as [[hydroiodic acid]]. Iodine possesses some metallic properties, despite being a [[Halogen]].

==Availability/Isolation==
[[File:Iodine Good Crystals.jpg|thumb|250px|Metallic iodine prepared by melting in H2SO4]]
Elemental iodine is sold by chemical suppliers, but it's not easy to get hold of.

Iodine is best extracted from iodine tinctures, though you will need large amounts of such tincture to obtain useful amounts of iodine. Iodine can be isolated by acidifying a soluble iodide (I-) solution to form [[hydroiodic acid]], adding an oxidizing agent like [[hydrogen peroxide]] to precipitate insoluble iodine, and purifying by sublimation. Adding concentrated [[sulfuric acid]] or [[nitric acid]] will produce iodine directly. Wet iodine can be dried by melting under concentrated sulfuric acid.

Another convenient source of iodine is seaweed, which contains a few percentages of iodine. To extract the iodine, you will need lots of dry seaweed, a few kg minimum. Old seaweed mattresses tend to be a good source. You can also collect it directly from beaches if it's permitted (check the local law before you do anything). Dry the seaweed then burn it in a container until it turns into ash. Add some water to the seaweed ash, then filter the suspension to separate the soluble part, which includes the iodine. Concentrate the solution until it crystals begin to form. To extract the iodine simply add conc. sulfuric acid, followed by conc. hydrogen peroxide. Dry and purify the resulting iodine. Keep in mind that seaweed also contains bromine and lots of chlorine (from sodium bromide and sodium chloride aka sea salt) and this may contaminate you iodine.<ref>https://www.youtube.com/watch?v=jmWB1Sl2uzE</ref>

===Legality===
Iodine is not easily purchased in the United States and other countries that tightly control drug precursors, as iodine is often used in the clandestine manufacture of methamphetamine.

Iodine is a controlled substance in many countries due to its use in producing illicit drugs, and while possession of iodine itself may not be a crime, its presence in a lab may be used to build a case against an innocent amateur chemist.

However, in most countries elemental iodine can be purchased freely, with no restrictions.

==Projects==
*Make [[nitrogen triiodide]]
*Make organoiodine compounds ([[methyl iodide]], [[ethyl iodide]], [[iodoform]], etc.)
*Anhydrous metal iodides
*Make [[hydrogen iodide]] and [[hydroiodic acid]]
*Activating magnesium for [[Grignard reagent]] prep
*Make purple smoke (dangerous)
*Iodoform test (detecting aldehydes and ketones)

==Handling==
===Safety===
Iodine, like other halogens, is toxic in large quantities and its vapors should not be inhaled. Objects stained with iodine solution or with solid iodine on them should not be brought inside or left out, as any iodine will sublimate given time. Iodine stains can be cleaned with a solution of [[sodium thiosulfate]].

Iodine is corrosive to most common metals, which is why it should only be handled with glass or plastic tools.

===Storage===
Elemental iodine is very difficult to store properly, as it tends to sublime at ambient temperatures and its vapors will escape the storage bottle, and stain the environment where it's stored. Sealing the bottle with [[parafilm]] or teflon tape will reduce the escaping iodine vapors. Do NOT use aluminium or any other metal foil, as it will corrode.

A more permanent way is to store the iodine in a sealed glass ampoule.

===Disposal===
Iodine can be neutralized by reacting it with a reducing agent, like sodium or potassium thiosulfate.

==References==
<references />
===Relevant Sciencemadness threads===
*[http://www.sciencemadness.org/talk/viewthread.php?tid=1869 Finally! Povidone iodine extraction (this one works way better than Rhodiums extraction method)]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=14229 Iodine from seaweed]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=10887 Iodine preparation for who needs it]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=19745 Synthesis of Iodine from KI and sulfuric acid question.]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=6200 Liquid Iodine]

[[Category:Elements]]
[[Category:Halogens]]
[[Category:Diatomic elements]]
[[Category:Nonmetals]]
[[Category:P-block]]
[[Category:DEA List I chemicals]]

Glyoxal

2020-09-27T19:34:27Z

Draeger: Added SMILES code and added image.

{{Chembox
| Name = Glyoxal
| Reference =
| IUPACName = Ethanedial
| PIN =
| SystematicName =
| OtherNames = Ethane-1,2-dial Ethanedione Ketoethanal Oxalaldehyde Oxaldehyde

| ImageFile = Glyoxal structural formula.png
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| Section1 = {{Chembox Identifiers
| 3DMet =
| Abbreviations =
| SMILES = C(=O)C=O
}}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance = Colorless to yellow solid, yellow liquid giving off greenish vapors (pure) Colorless liquid (solution)
| BoilingPt =
| BoilingPtC = 51
| BoilingPt_ref =
| BoilingPt_notes =
| Density = 1.14 g/cm3 (liquid) (20 °C)<ref>Debus; Justus Liebigs Annalen der Chemie; vol. 102; (1857); p. 28</ref> 1.27 g/cm3 (40% aq. solution) (20 °C)
| Formula = C2H2O2 CHOCHO
| HenryConstant =
| LogP = -1.66
| MolarMass = 58.036 g/mol
| MeltingPt =
| MeltingPtC = 15
| MeltingPt_ref =
| MeltingPt_notes = <ref>Debus; Justus Liebigs Annalen der Chemie; vol. 102; (1857); p. 28</ref>
| Odor = Mild odor
| pKa =
| pKb =
| Solubility = Miscible
| SolubleOther = Reacts with [[amine]]s Miscible with [[alcohol]]s, [[ether]]s, [[ketone]]s
| Solvent =
| VaporPressure = 18 mmHg (20 °C)
}}
| Section3 = {{Chembox Structure
| Coordination =
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}}
| Section4 = {{Chembox Thermochemistry
| DeltaGf =
| DeltaHc =
| DeltaHf =
| Entropy =
| HeatCapacity =
}}
| Section5 = {{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor =
}}
| Section6 = {{Chembox Hazards
| AutoignitionPt = 285 °C (545 °F; 558 K)
| ExploLimits =
| ExternalMSDS = [https://www.docdroid.net/mbFbNnK/glyoxal-40-percent-aq-solution-sa-pdf Sigma-Aldrich] (40% aq. sol.)
| FlashPt = −4 °C (25 °F; 269 K)
| LD50 = 3,300 mg/kg (rat, oral)
| LC50 =
| MainHazards = Irritant Toxic Flammable
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
}}
| Section7 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = [[Acetaldehyde]] [[Ethylene glycol]] [[Oxalic acid]]
}}
}}
'''Glyoxal''' is an organic compound with the chemical formula '''CHOCHO''' or '''C2H2O2'''. It is the simplest dialdehyde (a compound with two aldehyde groups).

==Properties==
===Chemical===
Pure glyoxal is said to burn in air/oxygen with a purple flame.

: C2H2O2 + 3/2 O2 → 2 CO2 + H2O

Pure glyoxal is not commonly encountered because it forms hydrates, which oligomerize. For many purposes, these hydrated oligomers behave equivalently to glyoxal.

Glyoxal is oxidized by dilute [[nitric acid]] to glyoxyl acid, while conc. nitric acid will oxidize it to [[oxalic acid]].

===Physical===
Glyoxal is a volatile liquid that freezes just slightly below room temperature. The compound is interesting, because unlike other small weight CHO compounds, it is not colorless. The liquid and solid forms are yellow, while the vapors of this compound are green.

==Availability==
Glyoxal is sold as 40% solution by chemical suppliers.

==Preparation==
Glyoxal can be prepared by careful oxidation of [[ethanol]] with [[nitric acid]].

Another lab route involves oxidation of [[acetaldehyde]] with [[selenous acid]]. Yield is given to be 70%. If selenium dioxide is used, the yield varies between 60-84%, and selenous acid/selenium dioxide is preferred over nitric acid, as it is more selective.<ref>http://www.orgsyn.org/demo.aspx?prep=cv3p0438</ref>

Commercial glyoxal is prepared either by the gas-phase oxidation of [[ethylene glycol]] in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of [[acetaldehyde]] with [[nitric acid]]. Cooper oxide can be used as catalyst at 300 °C.<ref>http://www.inchem.org/documents/cicads/cicads/cicad57.htm#4.1</ref>

Decarboxylation of dihydroxy-tartaric acid salts in the presence of [[sodium bisulfite]] has been shown to yield glyoxal.<ref>https://books.google.ro/books?id=AQ42AQAAMAAJ&dq=editions:y5IMLeQql-4C&source=gbs_navlinks_s&redir_esc=y&hl=ro</ref>

Ozonolysis of [[benzene]] has been shown to produce glyoxal.<ref>https://pubs.acs.org/doi/abs/10.1021/i360029a017</ref>

Anhydrous glyoxal is prepared by heating solid glyoxal hydrate(s) with [[phosphorus pentoxide]] and condensing the vapors in a cold trap.<ref>https://zenodo.org/record/1426217#.XzrghFBS_IU</ref>

Another route to anhydrous glyoxal involves adding [[1,2-Dichloroethane|dichloroethane]] to [[oleum]] at 58-60 °C, in the presence of [[mercury(II) chloride]] as catalyst. Glyoxal sulfate is produced, which is neutralized with calcium carbonate to yield glyoxal.<ref>Brudz, V. G.; Drapkina, D. A.; Markovich, I. S., Sb. Statei, Vses. Nauchn.-Issled. Inst. Khim. Reaktivov i Osobo Chistykh Khim. Veshchestv (1961), (No. 24), 98-101</ref>

==Projects==
*Colored compound
*Preparation of imidazoles and other similar heterocyclic compounds
*Synthesis of [[Hexanitrohexaazaisowurtzitane|HNIW]]
*Synthesis of [[glycoluril]] and [[tetranitroglycoluril]] (TNGU)
*Solubilizer and cross-linking agent in polymer chemistry
*Fixative for histology
*Wrinkle-resistant chemical treatments of clothing

==Handling==
===Safety===
Glyoxal is volatile, flammable, irritant and like most simple aldehydes, suspected carcinogen. Wear proper protection when working with this compound.

===Storage===
Should be kept at constant temperature. In solution may precipitate on storage, and can be redissolved by heating at 50-60 °C.

===Disposal===
Glyoxal can be neutralized by precipitating it with a base. Can also be mixed with acetone or ethanol and burned.

==References==
<references/>
===Relevant Sciencemadness threads===
*[https://sciencemadness.org/talk/viewthread.php?tid=4425 Glyoxal Synthesis]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=61441 Glyoxal + hydrazine]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=80481 2 Questions about Glyoxal]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=25682 incomplete glyoxal amide reaction]

[[Category:Chemical compounds]]
[[Category:Organic compounds]]
[[Category:Aldehydes]]
[[Category:Volatile chemicals]]
[[Category:Carcinogenic]]
[[Category:Contact poisons]]
[[Category:Liquids]]
[[Category:Air-sensitive materials]]

File:Glyoxal structural formula.png

2020-09-27T19:31:46Z

Draeger: The structural formula of glyoxal. The license is public domain.

The structural formula of glyoxal. The license is public domain.

Propionic anhydride

2020-09-27T19:07:08Z

Draeger: Fixed grammar and made disposal recommendation more clear.

{{Chembox
| Name = Propionic anhydride
| Reference =
| IUPACName = Propanoic anhydride
| PIN =
| SystematicName =
| OtherNames = Propanoic acid, anhydride Propanoyl propanoate

| ImageFile = Propionic anhydride skeletal structure.png
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| Section1 = {{Chembox Identifiers
| 3DMet =
| Abbreviations =
| SMILES = CCC(=O)OC(=O)CC
}}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance = Colorless liquid
| BoilingPt =
| BoilingPtC = 167-170
| BoilingPt_ref =
| BoilingPt_notes =
| Density = 1.015 g/cm3 (20 °C)
| Formula = C6H10O3 (CH3CH2CO)2O
| HenryConstant =
| LogP = 0.40
| MolarMass = 130.14 g/mol
| MeltingPt =
| MeltingPtC = −42
| MeltingPt_ref =
| MeltingPt_notes =
| Odor = Pungent, rancid odor
| pKa =
| pKb =
| Solubility = Slowly hydrolyzes
| SolubleOther = Miscible with [[chloroform]], [[diethyl ether]], [[ethanol]], [[isopropanol]], [[methanol]] Slightly soluble in [[carbon tetrachloride|CCl4]]
| Solvent =
| VaporPressure = 1.36 mm Hg at 25 °C
}}
| Section3 = {{Chembox Structure
| Coordination =
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| DeltaGf =
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| Section5 = {{Chembox Explosive
| ShockSens =
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| DetonationV =
| REFactor =
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| Section6 = {{Chembox Hazards
| AutoignitionPt = 285 °C (545 °F; 558 K)
| ExploLimits = 1.48-11.9%
| ExternalMSDS = [https://www.docdroid.net/dN4ZkSd/propionic-anhydride-sa.pdf Sigma-Aldrich]
| FlashPt = 63 °C (145 °F; 336 K)
| LD50 = 2,360 mg/kg (rat, oral)
| LC50 =
| MainHazards = Irritant Corrosive
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
}}
| Section7 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = [[Acetic anhydride]]
}}
}}
'''Propanoic anhydride''' or '''propionic anhydride''' is an organic compound with the formula '''(CH3CH2CO)2O'''.

==Properties==
===Chemical===
Propanoic anhydride slowly hydrolyzes in water to [[propionic acid]].

===Physical===
Propionic anhydride is a colorless liquid, with a strong pungent smell, which is insoluble in water, but slowly hydrolyzes upon contact. It is miscible with most organic solvents.

==Availability==
Propionic anhydride is sold by chemical suppliers.

In the US, is it classified as a List I compound, due to its use in the illicit manufacturing of fentanyl and its analogues. As such it cannot be acquired by private individuals, and a license is required to purchase and use the compound.

==Preparation==
Propionic anhydride can be easily prepared by dry distilling a mixture of dry [[calcium propionate]] and [[propionyl chloride]].

Alternatively, distilling a mixture [[propionic acid]] and [[oxalyl chloride]] will produce propionic anhydride, with a yield of 51%.<ref>https://www.prepchem.com/synthesis-of-propionic-anhydride</ref>

Propanoic anhydride can also be obtained by dehydration of dry [[propionic acid]] using [[ethenone]].

: 2 CH3CH2CO2H + CH2=C=O → (CH3CH2CO)2O + CH3CO2H

Another route is the Reppe carbonylation of [[ethylene]] with propionic acid and nickel carbonyl as the catalyst:<ref>https://onlinelibrary.wiley.com/doi/10.1002/14356007.a22_223.pub4</ref>

: CH2=CH2 + CH3CH2CO2H + CO → (CH3CH2CO)2O

==Projects==
*Make esters

==Handling==
===Safety===
Propanoic anhydride is strong smelling and corrosive and will cause burns on contact with skin. Vapour can burn the eyes and lungs.

===Storage===
In closed bottles, away from moisture.

===Disposal===
Can be neutralized by adding it in a diluted NaOH or KOH solution, which causes it to hydrolyze to propionic acid and finally sodium or potassium propionate, respectively, which is harmless and can be poured down the drain or dumped in soil.

==References==
<references/>
===Relevant Sciencemadness threads===
*[http://www.sciencemadness.org/talk/viewthread.php?tid=12855 propionic anhydride]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=76492 proprionic anhydride new rt synthesis]

[[Category:Chemical compounds]]
[[Category:Organic compounds]]
[[Category:Carboxylic acid anhydrides]]
[[Category:Foul smelling compounds]]
[[Category:Materials that react with water]]
[[Category:Materials unstable in basic solution]]
[[Category:DEA List I chemicals]]
[[Category:Liquids]]
[[Category:Irritants]]

Sodium methyl sulfate

2020-09-26T22:44:16Z

Draeger: Fixed a grammar mistake and added SMILES code.

{{Chembox
| Name = Sodium methyl sulfate
| Reference =
| IUPACName = Sodium methyl sulfate
| PIN =
| SystematicName =
| OtherNames = Methyl sodium sulfate Methylsulfuric Acid Sodium Salt Sodium methyl sulphate

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| Section1 = {{Chembox Identifiers
| 3DMet =
| Abbreviations =
| SMILES = COS(=O)(=O)[O-].[Na+]
}}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance = White solid
| BoilingPt =
| BoilingPtC =
| BoilingPt_ref =
| BoilingPt_notes = Decomposes
| Density =
| Formula = CH3NaSO4
| HenryConstant =
| LogP = -0.45
| MolarMass = 134.081 g/mol
| MeltingPt =
| MeltingPtC = 210
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| Odor =
| pKa =
| pKb =
| Solubility = Reacts
| SolubleOther = Reacts with alkali
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| Section4 = {{Chembox Thermochemistry
| DeltaGf =
| DeltaHc =
| DeltaHf =
| Entropy =
| HeatCapacity =
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| Section5 = {{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor =
}}
| Section6 = {{Chembox Hazards
| AutoignitionPt =
| ExploLimits =
| ExternalMSDS = [https://www.docdroid.net/f6RwyIY/sodium-methyl-sulfate-sa.pdf Sigma-Aldrich]
| FlashPt =
| LD50 =
| LC50 =
| MainHazards = Corrosive Toxic
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
}}
| Section7 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = [[Dimethyl sulfate]] [[Sodium sulfate]]
}}
}}
'''Sodium methyl sulfate''' is a chemical compound sometimes used as a methylating agent.

==Properties==
===Chemical===
Heating methyl sodium sulfate yields [[dimethyl sulfate]]:

:2 CH3NaSO4 → Na2SO4 + (CH3)2SO4

===Physical===
Sodium methyl sulfate is a white solid, that dissolves exothermically in water.

==Availability==
Sodium methyl sulfate is sold by various lab suppliers.

==Preparation==
Sodium methyl sulfate can be prepared by reacting [[sulfur trioxide]] with [[sodium methoxide]].

==Projects==
*Make [[nitromethane]]

==Handling==
===Safety===
Sodium methyl sulfate is corrosive and toxic.

===Storage===
In air-tight bottles and containers.

===Disposal===
Should be added in large amounts of water and neutralized with a base.

==References==
<references/>
===Relevant Sciencemadness threads===
*[http://www.sciencemadness.org/talk/viewthread.php?tid=145447 Sodium methyl sulfate]

[[Category:Chemical compounds]]
[[Category:Organic compounds]]
[[Category:Sodium compounds]]
[[Category:Organosulfates]]
[[Category:Methylating agents]]
[[Category:Materials that react with water]]
[[Category:Materials unstable in basic solution]]

Lithium hydride

2020-09-26T16:24:03Z

Draeger: Added SMILES code.

{{Chembox
| Name = Lithium hydride
| Reference =
| IUPACName = Lithium hydride
| PIN =
| SystematicName =
| OtherNames = Lithium monohydride

| ImageFile = Lithium hydride crystal by ChemicalForce.jpg
| ImageSize = 300
| ImageAlt =
| ImageName =
| ImageCaption = Crystallized LiH. It's blue not because of the reflection of the glove color, but because lithium hydride turns blue as it ages.
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| Section1 = {{Chembox Identifiers
| 3DMet =
| Abbreviations =
| SMILES = [LiH]
}}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance = White or light gray samples
| BoilingPt =
| BoilingPtC = 900
| BoilingPt_ref =
| BoilingPt_notes = (decomposes)
| Density = 0.78 g/cm3
| Formula = LiH
| HenryConstant =
| LogP =
| MolarMass = 7.95 g/mol
| MeltingPt =
| MeltingPtC = 688.7
| MeltingPt_ref =
| MeltingPt_notes =
| Odor = Odorless
| pKa =
| pKb =
| Solubility = Reacts
| SolubleOther = Reacts with [[alcohol]]s, [[aldehyde]]s, [[amine]]s, [[ammonia]], [[carboxylic acid]]s, [[dimethyl sulfoxide|DMSO]], [[ester]]s, [[ether]]s, [[halocarbon]]s, [[ketone]]s Soluble in molten [[lithium borohydride]], [[lithium fluoride]] and [[sodium hydride]] Slightly soluble in [[dimethylformamide]] Insoluble in hydrocarbons
| Solvent =
| VaporPressure = ~0 mmHg
}}
| Section3 = {{Chembox Structure
| Coordination =
| CrystalStruct = fcc (NaCl-type)
| MolShape =
}}
| Section4 = {{Chembox Thermochemistry
| DeltaGf = -69.98 kJ/mol
| DeltaHc =
| DeltaHf = -90.65 kJ/mol
| Entropy = 170.8 J·mol-1K-1
| HeatCapacity = 34.49 J·mol-1K-1
}}
| Section5 = {{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor =
}}
| Section6 = {{Chembox Hazards
| AutoignitionPt = 200 °C (392 °F; 473 K)
| ExploLimits =
| ExternalMSDS = [https://www.docdroid.net/scXX7JO/lithium-hydride-sa.pdf Sigma-Aldrich]
| FlashPt =
| LD50 =
| LC50 =
| MainHazards = Pyrophoric
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
}}
| Section7 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = [[Sodium hydride]] [[Calcium hydride]]
}}
}}
'''Lithium hydride''' is an inorganic compound with the formula '''LiH'''.

==Properties==
===Chemical===
Lithium hydride reacts with water to release hydrogen.

: LiH + H2O → LiOH + H2

===Physical===
Lithium hydride is an odorless white or slight grayish solid, which reacts with most solvents and is insoluble in those with which it doesn't react, like hydrocarbons.

==Availability==
Lithium hydride is sold by chemical suppliers, though it's not cheap, and it's hard to find.

On Alibaba one can find many sellers selling what is described as "lihium hydride", but be very careful if you want to purchase the product from there, since most of the prices listed for this compound are very low, which may be suspicious, since lithium compounds aren't cheap, let alone a hydrogen-rich and potentially pyrophoric powdered lithium compound.

==Preparation==
Can be prepared by reacting molten [[lithium]] metal with [[hydrogen]]. The reaction takes place in a [[nickel]] [[crucible]], between 450-500 °C, and the hydrogen used must be air and water-free. The yield of this reaction is 95%.<ref>[http://actachemscand.org/pdf/acta_vol_03_p1050-1057.pdf Brandt, P.; Acta Chemica Scandinavica (1947-1973); vol. 3; (1949); p. 1050 - 1057]</ref>

However, the reaction can proceed at temperatures as low as 29 °C. The yield is 60% at 99 °C and 85% at 125 °C, and the rate depends significantly on the surface condition of LiH and the purity of the inert gas used as inert conditions.

Hydrogenolysis of n-butyllithium at normal temperature and atmospheric pressure in the absence of catalyst will yield LiH.<ref>Gilman, H.; Jacoby, A. L.; Ludeman, H.; Journal of the American Chemical Society; vol. 60; (1938); p. 2336 - 2338</ref>

==Projects==
*Desiccant
*Make [[lithium aluminium hydride]]

==Handling==
===Safety===
Lithium hydride is very reactive towards most common solvents, it will even slowly attack ethers. It may spontaneously ignite in moist air.

===Storage===
Lithium hydride must be kept in air-tight containers, in an inert atmosphere, away from moisture. [[Schlenk flask]]s are good storage containers.

===Disposal===
Lithium hydride can be safely neutralized by slowly adding it in a large volume of alcohol, followed by slow addition of water.

==References==
<references/>
===Relevant Sciencemadness threads===
*[http://www.sciencemadness.org/talk/viewthread.php?tid=64720 Lithium hydride]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=75444 Lithium Hydride synthesis]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=23944 Lithium Hydride Preperation]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=80616 LiH Production Apparatus Design and Operation]

[[Category:Chemical compounds]]
[[Category:Inorganic compounds]]
[[Category:Lithium compounds]]
[[Category:Hydrogen compounds]]
[[Category:Metal hydrides]]
[[Category:Bases]]
[[Category:Insoluble compounds]]
[[Category:Reducing agents]]
[[Category:Desiccants]]
[[Category:Materials unstable in acidic solution]]
[[Category:Materials that react with water]]
[[Category:Irritants]]
[[Category:Air-sensitive materials]]
[[Category:Pyrophoric materials]]

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