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D&C ORANGE NO. 4
"Descrizione"
by admin (19362 pt) 		2024-May-22 13:14

D&C ORANGE NO.4 (Acid Orange 7, CI 15510) is a synthetic, azoic chemical dye, a class of commercial organic dyes.

The name Acid Orange 7 defines the structure of the molecule:

  • "Acid" means that this is an acid dye, therefore soluble in water and with anionic functional groups.
  • "Orange 7" is the specific identifier for this dye within the color index.

The synthesis process takes place in several stages:

  • Step 1: Preparation of raw materials. The raw materials for the synthesis of Acid Orange 7 are typically aromatic compounds, such as naphthalene or aniline, which are chemically modified to produce the desired color.
  • Step 2: Diazotization. The first step in the synthesis of many dyes, including Acid Orange 7, is diazotization. This involves treating an aromatic amine with nitrous acid to produce a diazonium salt.
  • Step 3: Coupling. The diazonium salt is reacted with another aromatic compound in a process known as coupling. This forms the azo dye.
  • Step 4: Purification. The resulting dye Acid Orange 7 is then purified to remove any unreacted raw materials and by-products. This is typically done through a series of washing and filtration steps.
  • Step 5: Drying. The purified dye Acid Orange 7 is then dried to remove any residual solvent.
What it is for and where
 

Cosmetics

CI 15510 is a restricted ingredient as IV/21  a Relevant Item in the Annexes of the European Cosmetics Regulation 1223/2009. Ingredient at risk: 

It is a dye added in liquid soaps, shampoos, etc. It is used in the textile field for the coloring of garments.
 
The dyes are divided into two categories:
  • natural compounds or additives derived from the natural ingredient (i)
  • synthetic chemicals (ii)
this dye belongs to the azo group, the largest group of dyes.
 
Safety
 

It is an ingredient that has some important contraindications regarding the health profile: it must not come into contact with areas close to the eyes.

It may cause damage to skin, eyes, chronic toxicity and carcinogenicity (1).
 
With the increase in textile consumption and the commercial interest in color diversification, industries have increased the use of color additives in the production of garments, for example Acid Orange 7 or Orange II. Acid Orange 7 is a synthetic acid dye which is toxic at a concentration of 0.011 mg / mL as expressed by the EC 50 acute toxicity test. Therefore, technologies and studies have been developed to try to remove this component from water (2).
 
Another system for the removal of CI 15510 from water uses nanosized ordered magnetic mesoporous Fe-Ce bimetal oxides (3).
 
Electrochemistry coupled with granulated activated carbon catalysis of peroxymonosulfate (electro/GAC/PMS) as a novel wastewater treatment process was performed for the degradation of Acid Orange 7 (AO7) in aqueous solution (4).

The problem with azo dyes (monoazo or diazo) is photocatalytic degradation leading to oxidation and subsequent formation of impurities such as aromatic amines, some of which have carcinogenic activity (5).

 
Synonyms :
  • ACID ORANGE 7
  • DC ORANGE NO. 4
  • CI 15510
  • NSC-101008
  • Orange 4


Molecular formula    C16H11N2NaO4S
 
Molecular weight   350.32 g / mol
 
CAS   633-96-5
 
References_____________________________________________________________________
 
(1) Zhang L, Cheng Z, Guo X, Jiang X, Liu R  Process optimization, kinetics and equilibrium of orange G and acid orange 7 adsorptions onto chitosan/surfactant. .  Journal of Molecular Liquids. 2014;197:353–67. doi: 10.1016/j.molliq.2014.06.007


(2) Batista AC, Silva MC, Batista JB, Nascimento AE, Campos-Takaki GM.  Eco-friendly chitosan production by Syncephalastrum racemosum and application to the removal of acid orange 7 (AO7) from wastewaters. Molecules. 2013 Jul

Hamzeh Y, Ashori A, Azadeh E, Abdulkhani A Removal of Acid Orange 7 and Remazol Black 5 reactive dyes from aqueous solutions using a novel biosorbent.  Mater Sci Eng C Mater Biol Appl. 2012 Aug.

(3) Wen Z, Zhang Y, Cheng G, Wang Y, Chen R. Simultaneous removal of As(V)/Cr(VI) and acid orange 7 (AO7) by nanosized ordered magnetic mesoporous Fe-Ce bimetal oxides: Behavior and mechanism.   Chemosphere. 2019 Mar;218:1002-1013. doi: 10.1016/j.chemosphere.2018.11.208. Epub 2018 Nov 30.

(4) Li J, Lin H, Zhu K, Zhang H. Degradation of Acid Orange 7 using peroxymonosulfate catalyzed by granulated activated carbon and enhanced by electrolysis.   Chemosphere. 2017 Dec;188:139-147. doi: 10.1016/j.chemosphere.2017.08.137. Epub 2017 Aug 28

(5) Chung KT, Stevens SE Jr, Cerniglia CE. The reduction of azo dyes by the intestinal microflora. Crit Rev Microbiol. 1992;18(3):175-90. doi: 10.3109/10408419209114557.

Abstract. Azo dyes are widely used in the textile, printing, paper manufacturing, pharmaceutical, and food industries and also in research laboratories. When these compounds either inadvertently or by design enter the body through ingestion, they are metabolized to aromatic amines by intestinal microorganisms. Reductive enzymes in the liver can also catalyze the reductive cleavage of the azo linkage to produce aromatic amines. However, evidence indicates that the intestinal microbial azoreductase may be more important than the liver enzymes in azo reduction. In this article, we examine the significance of the capacity of intestinal bacteria to reduce azo dyes and the conditions of azo reduction. Many azo dyes, such as Acid Yellow, Amaranth, Azodisalicylate, Chicago Sky Blue, Congo Red, Direct Black 38, Direct Blue 6, Direct Blue 15, Direct Brown 95, Fast Yellow, Lithol Red, Methyl Orange, Methyl Red, Methyl Yellow, Naphthalene Fast Orange 2G, Neoprontosil, New Coccine, Orange II, Phenylazo-2-naphthol, Ponceau 3R, Ponceau SX, Red 2G, Red 10B, Salicylazosulphapyridine, Sunset Yellow, Tartrazine, and Trypan Blue, are included in this article. A wide variety of anaerobic bacteria isolated from caecal or fecal contents from experimental animals and humans have the ability to cleave the azo linkage(s) to produce aromatic amines. Azoreductase(s) catalyze these reactions and have been found to be oxygen sensitive and to require flavins for optimal activity. The azoreductase activity in a variety of intestinal preparations was affected by various dietary factors such as cellulose, proteins, fibers, antibiotics, or supplementation with live cultures of lactobacilli.

 

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