Salicylic acid

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Revision as of 21:38, 2 December 2024 by Admin (talk | contribs) (Created page with "{{Compound|name=Salicylic acid|chemf=C7H6O3|struct=SalicylicAcid.png|mm=138.12|density=1.443|mp=158.6|bp=200|sol_aq=2.2-2.48|sol_et=275 (35%w/w)|medicine=yes|listed_who=yes|nfpa_h=2|nfpa_f=1}} ==Uses== * Precursor to acetylsalicylic acid * Precursor to bismuth subsalicylate * Topical treatment for warts and dandruff * Potential precursor for '''salbutamol''' ==Natural occurence== * '''Does''' occur natually in several plants. See methyl salicylate ==Hazards==...")
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Legality: DEA Listed Chemicals

Production of this substance may be illegal in some jurisdictions under certain circumstances.

21CFR1310.02 a & b

In 1995/6, two lists were created "List I" and "List II", for which commercial manufacturers and distributors must register, and for which possession with the intent to manufacture illegal substances (such as methamphetamine, ecstasy, etc) is illegal. On these a few dozen "precursor" compounds commonly used in the manufacture of illegal drugs. <ref>{{

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Bottom line: Do not produce this chemical without checking to make sure that you may do so legally.

 

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Legality: CWC Schedule 3

CONVENTION ON THE PROHIBITION OF THE DEVELOPMENT, PRODUCTION, STOCKPILING AND USE OF CHEMICAL WEAPONS AND ON THEIR DESTRUCTION
ANNEX ON CHEMICALS
A. GUIDELINES FOR SCHEDULES OF CHEMICALS
Guidelines for Schedule 3
The following criteria shall be taken into account in considering whether a toxic chemical or precursor, not listed in other Schedules, should be included in Schedule 3:
(a) It has been produced, stockpiled or used as a chemical weapon;
(b) It poses otherwise a risk to the object and purpose of this Convention because it possesses such lethal or incapacitating toxicity as well as other properties that might enable it to be used as a chemical weapon;
(c) It poses a risk to the object and purpose of this Convention by virtue of its importance in the production of one or more chemicals listed in Schedule 1 or Schedule 2, part B;
(d) It may be produced in large commercial quantities for purposes not prohibited under this Convention.

Production of this substance may be illegal in some jurisdictions under certain circumstances. Bottom line: Do not produce this chemical without checking to make sure that you may do so legally.

 

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Legality: Controlled Substance

USC Title 21<ref>21 USC §812{{
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Production, Possession, or distribution of this substance without permission or defined legal justification may be illegal.

Bottom line: Do not produce this substance without checking to make sure that you may do so legally.

 

[[Category:US Schedule {{#ifeq: |1|I|{{#ifeq:|2|II|{{#ifeq:|3|III|{{#ifeq:|4|IV|{{#ifeq:|5|V|}}}}}}}}}} Substances]]}}

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DEA LIST I/II SUBSTANCE}} {{#if:|
CWC LIST I/II/III SUBSTANCE}} {{#if:||
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NFPA 704
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Uses

Natural occurence

Hazards

  • LD50 (rat, oral): 0.4g/kg

Production

Synthesis

From methyl salicylate

From phenol

carbonylation
  • React phenol with sodium hydroxide, producing sodium phenoxide
    {{#Chem: C6H5OH + NaOH --> NaC6H5O + H2O }}
  • React the sodium phenoxide with carbon dioxide at 180°C, producing sodium salicylate
    {{#Chem: NaC6H5O + CO2 { = 180°C } NaC7H5O3|t=180}}
  • React sodium salicylate with sulfuric acid producing salicylic acid and sodium sulfate
    {{#Chem: NaC7H5O3 + H2SO4 = C7H6O3 + Na2SO4}}
carbon tetrachloride

React phenol with carbon tetrachloride and sodium hydroxide giving salicylic acid

{{#Chem: C6H5OH + CCl4 + 4 NaOH(aq) { = strong stirring } C6H4OHCOOH + 4 NaCl + 2 H2O }}
The reaction must be heated to begin reaction, then cooled as it progresses.
Reaction must be stirred thoroughly or some additional solvent (dioxane) added to get the three materials to contact one another
trichloromethane
  1. React Phenol with trichloromethane and sodium hydroxide giving salicylaldehyde
    {{#Chem: C6H5OH + CHCl3 + 3 NaOH(aq) { = strong stirring } C6H4OHCOH + 3 NaCl + 2 H2O }}
    The reaction must be heated to begin reaction, then cooled as it progresses.
    Reaction must be stirred thoroughly or some additional solvent (dioxane) added to get the three materials to contact one another
  2. react salicylaldehyde with potassium dichromate to give salicylic acid
    {{#Chem: C6H4OHCOH + 2 K2Cr2O7 + H2O {H2SO4 = } C6H4OHCOOH + 2 K2CrO4 + 2 HCrO3 }}

Preparations

Testing

Purification

  1. REPEAT
    1. Dissolve acid in diethyl ether (333g/L) or ethanol (275g/L)
    2. Add water
    3. Neutralize to sodium salicylate (via sodium carbonate or sodium bicarbonate) to make it water soluble
    4. Extract aq layer
    5. Acidify w/ dilute sulfuric acid precipitates it from the aqueous layer
    6. Filter, discard filtrate
    7. The residue is pure(er) salicylic acid.
  2. UNTIL pure enough

Storage

Disposal

See Also

Web

See Also

References

<references/>

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