4-aminophenol

From NOWA-CL
Revision as of 22:59, 2 December 2024 by Admin (talk | contribs) (Created page with "{{Compound|struct=4-AminoPhenol.png|chemf=C6H7NO|mm=109.126|density=1.13|mp=187.5|bp=284|sol_aq=15|nfpa_h=2|nfpa_f=1|stp_p=crystals|stp_q=white or red/yellow}} ==Uses== * Vital precursor to paracetamol ==Natural occurrence== * 4-aminophenol '''does not''' occur naturally ==Hazards== * Flammable * Mutagen, Irritant, lowers blood oxygen via methemoglobin. ==Production== ===Synthesis=== ====Chemical reduction of nitrophenol==== =====sodium borohydride===== Combine the [...")
(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to navigation Jump to search

{{

  1. ifeq:|yes|

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>{{

  1. if:Emphasizing the "Control" in controlled substances||Template:Cite pub: Must have title}}{{
  2. if: |{{{last1}}}{{#if:|, {{{first1}}}}}{{
 #if:|; {{{last2}}}{{#if:|, {{{first2}}}}}}}{{
 #if:|; {{{last3}}}{{#if:|, {{{first3}}}}}}}{{
 #if:|; {{{last4}}}{{#if:|, {{{first4}}}}}}}{{
 #if:|; {{{last5}}}{{#if:|, {{{first5}}}}}}}{{
 #if:|; et al.}}}}{{
  1. if:| ({{{year}}})}} {{
  2. if:http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf%7C"Emphasizing the "Control" in controlled substances"|"Emphasizing the "Control" in controlled substances".}}{{
  3. if:| ([[media:{{{lc}}}|local copy]])}}{{
  4. if:||{{#if:|; pp{{{pages}}}.}}}}{{
  5. if:United States Drug Enforcement Agency|
    {{
  6. if:|{{
 #if:|{{{publication}}}{{
 #if:| {{{volume}}}}}{{
 #if:|({{{issue}}})}}{{
 #if:|; pp{{{pages}}}.}} }}}}{{
  1. if:United States Drug Enforcement Agency|United States Drug Enforcement Agency}}}}{{
  2. if:|
    {{
  3. if:|DOI:{{{doi}}}{{
 #if: |, }}}}{{
 #if: |ISBN: ERROR}}}}{{
  1. if:http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf%7C{{
 #if:{{#if:|11 September 2012|}}|
link courtesy {{{courtesy}}}, last accessed 11 September 2012.|{{
   #if:|
link courtesy {{{courtesy}}}.}}{{
   #if:11 September 2012|
link last accessed 11 September 2012.}}}}}}</ref>

<ref>{{

  1. if:Controlled Substances Act; Title 21; Chapter 13; Subchapter I||Template:Cite pub: Must have title}}{{
  2. if: |{{{last1}}}{{#if:|, {{{first1}}}}}{{
 #if:|; {{{last2}}}{{#if:|, {{{first2}}}}}}}{{
 #if:|; {{{last3}}}{{#if:|, {{{first3}}}}}}}{{
 #if:|; {{{last4}}}{{#if:|, {{{first4}}}}}}}{{
 #if:|; {{{last5}}}{{#if:|, {{{first5}}}}}}}{{
 #if:|; et al.}}}}{{
  1. if:| ({{{year}}})}} {{
  2. if:http://www.fda.gov/regulatoryinformation/legislation/ucm148726.htm%7C"Controlled Substances Act; Title 21; Chapter 13; Subchapter I"|"Controlled Substances Act; Title 21; Chapter 13; Subchapter I".}}{{
  3. if:| ([[media:{{{lc}}}|local copy]])}}{{
  4. if:||{{#if:|; pp{{{pages}}}.}}}}{{
  5. if:United States Food & Drug Administration|
    {{
  6. if:|{{
 #if:|{{{publication}}}{{
 #if:| {{{volume}}}}}{{
 #if:|({{{issue}}})}}{{
 #if:|; pp{{{pages}}}.}} }}}}{{
  1. if:United States Food & Drug Administration|United States Food & Drug Administration}}}}{{
  2. if:|
    {{
  3. if:|DOI:{{{doi}}}{{
 #if: |, }}}}{{
 #if: |ISBN: ERROR}}}}{{
  1. if:http://www.fda.gov/regulatoryinformation/legislation/ucm148726.htm%7C{{
 #if:{{#if:|11 September 2012|}}|
link courtesy {{{courtesy}}}, last accessed 11 September 2012.|{{
   #if:|
link courtesy {{{courtesy}}}.}}{{
   #if:11 September 2012|
link last accessed 11 September 2012.}}}}}}</ref>

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

 

{{#ifeq: |nocat||}}|}}{{

  1. if:|


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.

 

{{#ifeq: |nocat||}}|}}{{

  1. if:|

Legality: Controlled Substance

USC Title 21<ref>21 USC §812{{
  1. if: |, by {{{last1}}}{{#if:|, {{{first1}}}}}{{
 #if:|; {{{last2}}}{{#if:|, {{{first2}}}}}}}{{
 #if:|; {{{last3}}}{{#if:|, {{{first3}}}}}}}{{
 #if:|; {{{last4}}}{{#if:|, {{{first4}}}}}}}{{
 #if:|; {{{last5}}}{{#if:|, {{{first5}}}}}}}{{
 #if:|; et al.}}}}{{
  1. if:US Gov|
    courtesy US Gov.}}{{
  2. if:|
    Last accessed {{{accessdate}}}.}}{{
  3. if:| [[Media:{{{lc}}}|local copy]]}}</ref> defines five "schedules" of legally controlled substances
This substance is currently {{#if
|listed in Schedule {{#ifeq: |1|I|{{#ifeq:|2|II|{{#ifeq:|3|III|{{#ifeq:|4|IV|{{#ifeq:|5|V|}}}}}}}}}}|unlisted}}

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]]}}

{{
  1. ifeq:{{
  2. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  3. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  4. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}|none||{{
  5. ifexist:File:{{
  6. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  7. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  8. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}|{{
  9. if:|
{{#if:|  }}
4-aminophenol {{#if:|
aka }} {{#if:|
DEA LIST I/II SUBSTANCE}} {{#if:|
CWC LIST I/II/III SUBSTANCE}} {{#if:||
"{{
  1. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  2. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  3. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}"
 exists}}
[[Image:{{
  1. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  2. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  3. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}|300px]]|{{
  4. if:|
"{{
  1. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  2. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  3. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}"
 {{
  1. if:|
"{{
  1. if: 4-AminoPhenol.png|{{#ifexist:File:4-AminoPhenol.png|4-AminoPhenol.png|}}|{{
  2. ifexist:File:{{#if:|_struct.png|}}|{{#if:|_struct.png|}}|{{
  3. ifexist:File:{{#if:4-aminophenol|4-aminophenol_struct.png|}}|{{#if:4-aminophenol|4-aminophenol_struct.png|}}}}}}}}"
 IS EMPTY}}}}}}
13|{{#if:|14|10}}}}em;"|Chemical formula {{#Chem:C6H7NO}}|unspecified}}
Atomic Number  }}}}{{#if:white or red/yellow crystals| 
()}}  
Index of refraction  {{{3}}}}}}}{{#if:109.126| 
(g/mol)}}  
(kJ/mol)}}  
(g/cc)}}  
(°C)}}  
(°C)}}  
(×10-6 °C-1)}}  
(MJ/kg)}}  
(pH)}}  
(°C)}}  
(°C)}}  
(g/L)}}  
(g/L)}}  
(g/L)}}  
(g/L)}}  
(g/L)}}  
(mol%)}}  
(%v/v)}}  
(%w/w)}}  
(°C)}}  
(m/s)}}  
Immediate Danger to Life and Health  {{{3}}}}}}}{{#if:| 
LD50  {{{3}}}}}}}

{{#ifeq:"0x0x0x_"|"2x1x0x0"||

NFPA 704
1
2
0
{{#ifeq:0|0| |0}}
}}

{{

  1. if:| 

{{

  1. ifeq:|q|}}{{
  2. if:||}}{{
  3. if:|}}{{
  4. if:|[[Category:]]{{
#ifeq:|metal|}}{{
#ifeq:|metals|}}}}{{
  1. if:|}}{{
  2. if:|}}{{
  3. if:|}}{{
  4. if:|}}{{
  5. if:|}}{{
  6. if:|}}{{
  7. if:|}}

Uses

Natural occurrence

  • 4-aminophenol does not occur naturally

Hazards

  • Flammable
  • Mutagen, Irritant, lowers blood oxygen via methemoglobin.

Production

Synthesis

Chemical reduction of nitrophenol

sodium borohydride

Combine the 4-nitrophenol and sodium borohydride giving 4-aminophenol

{{#Chem:HO-C6H4-NO2 + NaBH4 { 1M/L NaOH, Pd/C = 13-17°C } HO-C6H4-NH2 + NaBO2 + H2}}
tin / hydrochloric acid
  1. Combine the 4-nitrophenol with tin in a reflux apparatus
  2. Drip in hydrochloric acid
    {{#Chem: 2 HOC6H4NO2 + 12 HCl + 3 Sn = 2 HOC6H4NH2 + 3 SnCl4 + 4 H2O}}
  3. Neutralize the solution with an icy saturated solution of sodium hydroxide
  4. Separate the remaining materials via distillation, salting, and liq/liq extractions

Electroreduction of nitrobenzene

JAE

The Journal of Applied Electrochemistry outlines the electrolysis (375mV) of a solution of nitrobenzene in 20% sulfuric acid produces an amine which rearranges into 4-aminophenol and aniline<ref>{{

  1. if:Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques||Template:Cite pub: Must have title}}{{
  2. if:Polat |Polat{{#if:K.|, K.}}{{
 #if:Aksu|; Aksu{{#if:M. L.|, M. L.}}}}{{
 #if:Pekel|; Pekel{{#if:A. T.|, A. T.}}}}{{
 #if:|; {{{last4}}}{{#if:|, {{{first4}}}}}}}{{
 #if:|; {{{last5}}}{{#if:|, {{{first5}}}}}}}{{
 #if:|; et al.}}}}{{
  1. if:2002| (2002)}} {{
  2. if:http://w3.gazi.edu.tr/~maksu/m21.pdf%7C"Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques"|"Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques".}}{{
  3. if:| ([[media:{{{lc}}}|local copy]])}}{{
  4. if:Journal of Applied Electrochemistry||{{#if:217-223|; pp217-223.}}}}{{
  5. if:Journal of Applied Electrochemistry|
    {{
  6. if:Journal of Applied Electrochemistry|{{
 #if:Journal of Applied Electrochemistry|Journal of Applied Electrochemistry{{
 #if:32| 32}}{{
 #if:|({{{issue}}})}}{{
 #if:217-223|; pp217-223.}} }}}}{{
  1. if:|{{{publisher}}}}}}}{{
  2. if:|
    {{
  3. if:|DOI:{{{doi}}}{{
 #if: |, }}}}{{
 #if: |ISBN: ERROR}}}}{{
  1. if:http://w3.gazi.edu.tr/~maksu/m21.pdf%7C{{
 #if:{{#if:||}}|
link courtesy {{{courtesy}}}, last accessed {{{lastaccessed}}}.|{{
   #if:|
link courtesy {{{courtesy}}}.}}{{
   #if:|
link last accessed {{{lastaccessed}}}.}}}}}}</ref>
{{#Chem: C6H5NO2 + 4H = C6H5NHOH + H2O // benzene amino hydrate}}
{{#Chem: C6H5NHOH + H = NH2-C6H4-OH // 4-aminophenol }}
{{#Chem: C6H5NHOH + 2H = C6H5NH2 + H2O // aniline and water }}}
SCV

SCV<ref>{{

  1. if:Aromatic nitro compounds||Template:Cite pub: Must have title}}{{
  2. if: |{{{last1}}}{{#if:|, {{{first1}}}}}{{
 #if:|; {{{last2}}}{{#if:|, {{{first2}}}}}}}{{
 #if:|; {{{last3}}}{{#if:|, {{{first3}}}}}}}{{
 #if:|; {{{last4}}}{{#if:|, {{{first4}}}}}}}{{
 #if:|; {{{last5}}}{{#if:|, {{{first5}}}}}}}{{
 #if:|; et al.}}}}{{
  1. if:2009| (2009)}} {{
  2. if:https://books.google.com/books?id=FX1nblFIoS4C&pg=PT43&lpg=PA25%7C"Aromatic nitro compounds"|"Aromatic nitro compounds".}}{{
  3. if:| ([[media:{{{lc}}}|local copy]])}}{{
  4. if:Competition Science Vision||{{#if:849-856|; pp849-856.}}}}{{
  5. if:Competition Science Vision|
    {{
  6. if:Competition Science Vision|{{
 #if:Competition Science Vision|Competition Science Vision{{
 #if:12| 12}}{{
 #if:139|(139)}}{{
 #if:849-856|; pp849-856.}} }}}}{{
  1. if:|{{{publisher}}}}}}}{{
  2. if:|
    {{
  3. if:|DOI:{{{doi}}}{{
 #if: |, }}}}{{
 #if: |ISBN: ERROR}}}}{{
  1. if:https://books.google.com/books?id=FX1nblFIoS4C&pg=PT43&lpg=PA25%7C{{
 #if:{{#if:||}}|
link courtesy {{{courtesy}}}, last accessed {{{lastaccessed}}}.|{{
   #if:|
link courtesy {{{courtesy}}}.}}{{
   #if:|
link last accessed {{{lastaccessed}}}.}}}}}}</ref>

Purification

Phase I

This phase eliminates materials like ethers, esters, and analine.<ref>{{#if:{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|3845129}}}}|{{#if:|US patent {{ safesubst:#if:1|3845129}} "[{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|3845129}}}} ]"|[{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|3845129}}}} US patent {{ safesubst:#if:1|3845129}}]}}|US patent {{ safesubst:#if:1|3845129}}{{#if:|, ""}}}}{{#if:| , }}{{#if:{{#ifeq:US|US|Google}}|
Link courtesy {{#ifeq:US|US|Google}}}}</ref> From an acidic aqueous solution of 4-aminophenol

  1. Neutralize pH to ~5.0-5.5 using ammonia
    N.B. should keep the 4-aminophenol dissolved in water (higher pH will cause it to precipitate)
  2. Repeat
    1. Exclude oxygen from the environment, maintain temperature at 60-70°C
    2. Mix thoroughly (countercurrent wash) with trichloromethane
    3. Evaporate the TCM and recycle
    4. Discard the acidic material left behind by the TCM
  3. Until satisfied
  4. Filter through carbon
  5. Discard carbon residue

Phase II

This phase eliminates 2-aminophenol<ref>{{#if:{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|4870209}}}}|{{#if:|US patent {{ safesubst:#if:1|4870209}} "[{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|4870209}}}} ]"|[{{#ifeq:US|US|http://www.google.com/patents/US{{ safesubst:#if:1|4870209}}}} US patent {{ safesubst:#if:1|4870209}}]}}|US patent {{ safesubst:#if:1|4870209}}{{#if:|, ""}}}}{{#if:| , }}{{#if:{{#ifeq:US|US|Google}}|
Link courtesy {{#ifeq:US|US|Google}}}}</ref>

  1. Prepare an aqueous solutionof 4- and 2- aminophenol at 75°C
  2. Increase pH of solution to 7.2 using ammonia
  3. Lower temperature to 1°C
  4. Filter
  5. Discard filtrate, potentially containing 2-aminophenol
  6. Retain residue, purified

See Also

References

<references/>

Retrieved from "http://nowa-cl.com/index.php?title=4-aminophenol&oldid=2008"