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Revision as of 19:25, 26 June 2012 editJü (talk | contribs)Extended confirmed users2,896 editsm names← Previous edit Latest revision as of 05:37, 20 November 2024 edit undo2600:1700:60bb:c810:a871:628e:4f46:e44f (talk) It was not the first azo dye, that would be aniline yellow, discovered about 20 years prior.Tags: Mobile edit Mobile web edit 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 400841579
| Watchedfields = changed
⚫ | ImageFile = Para Red.png
⚫ | verifiedrevid = 476994415
⚫ | ImageSize =
⚫ | ImageFile = Para Red Formula V.1.svg
⚫ | IUPACName = 1--2-naphthol
⚫ | ImageSize = 250px
⚫ | OtherNames = 1--2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1--2-naphthalenol, 1--2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS
⚫ | PIN = 1-naphthalen-2-ol
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = <nowiki>1--2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1--2-naphthalenol, 1--2-naphthol, 1--2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS</nowiki>
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13544963 | ChemSpiderID = 13544963
| InChI = 1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+ | InChI = 1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+
Line 14: Line 16:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WOTPFVNWMLFMFW-ISLYRVAYSA-N | StdInChIKey = WOTPFVNWMLFMFW-ISLYRVAYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|PubChem}}
| CASNo = 6410-10-2 | CASNo = 6410-10-2
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EINECS = 229-093-8
| PubChem = | UNII = D54Q24K2EI
⚫ | EINECS = 229-093-8
⚫ | SMILES = O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O
| PubChem = 22917
| ChEMBL = 1967257
⚫ | SMILES = O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=16
| Formula = C<sub>16</sub>H<sub>11</sub>N<sub>3</sub>O<sub>3</sub>
| H=11
| MolarMass =
| Appearance = Red solid | N=3
| O=3
| Appearance = Red solid
| Density = | Density =
| MeltingPt = 248 - 252 °C | MeltingPtC = 248 to 252
| BoilingPt = | MeltingPt_notes =
| Solubility = | BoilingPt =
| Solubility =
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
| RPhrases = {{R36/37/38}}
| SPhrases = {{S26}}, {{S36}}
| FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
⚫ }}
}} }}
'''Para Red''' ('''paranitraniline red''', '''Pigment Red 1''', '''C.I. 12070''') is a chemical ]. Chemically, the dye is similar to ]. The dye was discovered in 1880 by von Gallois and Ullrich, and was the first ]. It dyes cellulose fabrics a brilliant red, but is not very fast. The dye can be washed away easily from cellulose fabrics if not dyed correctly. Throughout making Para Red, the solution will become acidic and basic. Small amounts of byproducts may be left over after the Para Red dye is made that may be acidic or basic, but if made correctly there are little of these and the byproducts have no effect. '''Para red''' ('''paranitraniline red''', '''Pigment Red 1''', '''C.I. 12070''') is a ]. Chemically, it is similar to ]. It was discovered in 1880 by von Gallois and Ullrich. It dyes cellulose fabrics a brilliant red color, but is not very ]. The dye can be washed away easily from ] fabrics if not dyed correctly. Acidic and basic stages both occur during the standard formation of Para Red, and acidic or basic byproducts may be present in the final product.


==Synthesis== ==Synthesis==
Para Red is prepared by ] of ] at ice-cold temperatures, followed by coupling with ]:<ref>{{cite book Para red is prepared by ] of ] at ice-cold temperatures, followed by coupling with ]:<ref>{{cite book
| last = Williamson | last = Williamson
| first = Kenneth L. | first = Kenneth L.
| title = Macroscale and Microscale Organic Experiments, Fourth Edition | title = Macroscale and Microscale Organic Experiments, Fourth Edition
| publisher = ] | publisher = ]
| year = 2002 | year = 2002
| isbn = 0-618-19702-8}} | isbn = 0-618-19702-8
| url-access = registration
| url = https://archive.org/details/macroscalemicros00will_0
}}
</ref> </ref>
] :]{{clear-left}}


==UK food alert== ==Regulation==
In the ], the dye is not permitted in food. The UK's ] (FSA) stated that "''the Agency’s independent scientific experts have advised that, although there are very limited data available, it would be prudent to assume that it could be a genotoxic carcinogen''". <ref name=fsa>{{cite news | url = http://www.food.gov.uk/news/newsarchive/2005/apr/oldelpaso | title = Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye | publisher = ] | format = press release | date = 21 April 2005}}</ref> Para red is not approved for use in food in any jurisdiction. In 2005, ] dinner kits were found to be contaminated with the dye and removed from supermarket shelves.<ref name=fsa>{{cite news | url = http://www.food.gov.uk/news/newsarchive/2005/apr/oldelpaso | title = Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye | publisher = ] | format = press release | date = 21 April 2005}}</ref><ref>{{cite news | url = http://news.bbc.co.uk/1/hi/health/4518139.stm | title = Banned dye found in more products | publisher = ] | date = 5 May 2005}}</ref>

On 21 April 2005, the FSA announced that some batches of ] dinner kits had been contaminated with the dye, and issued an alert.<ref name=fsa/> Also, reported on the 5 May 2005, the dye was found in 35 products which have now been taken off supermarket shelves. The products were mainly cooking sauces, though some are also spices.<ref>{{cite news | url = http://news.bbc.co.uk/1/hi/health/4518139.stm | title = Banned dye found in more products | publisher = ] | date = 5 May 2005}}</ref>


==References== ==References==
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] ]
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Latest revision as of 05:37, 20 November 2024

Para red
Names
Preferred IUPAC name 1-naphthalen-2-ol
Other names 1--2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1--2-naphthalenol, 1--2-naphthol, 1--2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.449 Edit this at Wikidata
EC Number
  • 229-093-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+Key: WOTPFVNWMLFMFW-ISLYRVAYSA-N
  • InChI=1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+Key: WOTPFVNWMLFMFW-ISLYRVAYBR
SMILES
  • O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O
Properties
Chemical formula C16H11N3O3
Molar mass 293.282 g·mol
Appearance Red solid
Melting point 248 to 252 °C (478 to 486 °F; 521 to 525 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Para red (paranitraniline red, Pigment Red 1, C.I. 12070) is a dye. Chemically, it is similar to Sudan I. It was discovered in 1880 by von Gallois and Ullrich. It dyes cellulose fabrics a brilliant red color, but is not very fast. The dye can be washed away easily from cellulose fabrics if not dyed correctly. Acidic and basic stages both occur during the standard formation of Para Red, and acidic or basic byproducts may be present in the final product.

Synthesis

Para red is prepared by diazotization of para-nitroaniline at ice-cold temperatures, followed by coupling with β-naphthol:

Synthesis of Para Red
Synthesis of Para Red

Regulation

Para red is not approved for use in food in any jurisdiction. In 2005, Old El Paso dinner kits were found to be contaminated with the dye and removed from supermarket shelves.

References

  1. Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0-618-19702-8.
  2. "Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye" (press release). Food Standards Agency. 21 April 2005.
  3. "Banned dye found in more products". BBC News. 5 May 2005.

External links

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