Alkyl naphthalene sulfonates (ANS) are used in many industrial applications as nondetergent wetting agents that effectively disperse colloidal systems in aqueous media. These 1,8-dilithio derivatives are precursors to a host of peri-naphthalene derivatives.[21]. [42], Mothballs and other products containing naphthalene have been banned within the EU since 2008.[43][44]. Synthesis of Thiophene‐annulated Naphthalene Diimide‐based Small‐Molecular Acceptors via Two‐step C−H Activation. Oxidation with O2 in the presence of vanadium pentoxide as catalyst gives phthalic anhydride: This reaction is the basis of the main use of naphthalene. In Western Europe the well-known producers are Koppers, Ruetgers, and Deza. Cell suspensions were grown for 6–8 subcultures on media supplemented with various phytohormones. The major commercial applications are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and the textile and fabric industry, which utilizes the wetting and defoaming properties of ANS for bleaching and dyeing operations. A naphthalene molecule can be viewed as the fusion of a pair of benzene rings. Approximately 1.3M tons are produced annually.[22]. There are four reaction steps involved in this synthesis. 1172 0 obj
<>/Filter/FlateDecode/ID[<8788FF9F3E389742991234F683D9B24D>]/Index[1151 49]/Info 1150 0 R/Length 105/Prev 630474/Root 1152 0 R/Size 1200/Type/XRef/W[1 3 1]>>stream
AldrichCPR (1) ... naphtalene acetic acid. He proposed the name naphthaline, as it had been derived from a kind of naphtha (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar). The shared carbons are labeled 4a (between 4 and 5) and 8a (between 8 and 1). [27], Protonated cations of naphthalene (C10H+9) are the source of part of the spectrum of the Unidentified Infrared Emissions (UIRs). Naphthalene sulfonate polymers are produced by treating naphthalenesulfonic acid with formaldehyde, followed by neutralization with sodium hydroxide or calcium hydroxide. Please include product name, order quantity, usage, special requests if any in your inquiry. Female mice exhibited some evidence of carcinogenesis based on increased incidences of alveolar and bronchiolar adenomas of the lung, while male mice exhibited no evidence of carcinogenesis. Naphthalene is used in engineering to study heat transfer using mass sublimation. Chemistry – An Asian Journal 2019 , 14 (10) , 1651-1656. Protonated naphthalene differs from neutral naphthalene (e.g. 1151 0 obj
<>
endobj
The molecule is planar, like benzene. Exposure to large amounts of naphthalene may cause confusion, nausea, vomiting, diarrhea, blood in the urine, and jaundice (yellow coloration of the skin due to dysfunction of the liver).[35]. The naphthalenide salts are strong reducing agents. Power Grown's offers Naphthalene Acetic Acid 98% 10 Grams water soluble Tech grade for only $12.99. NAA is a broad-spectrum plant growth regulator. Oxidation can also be effected using conventional stoichiometric chromate or permanganate reagents. This difference, established by X-ray diffraction,[17] is consistent with the valence bond model in naphthalene and in particular, with the theorem of cross-conjugation. However, the solid shows semiconducting character below 100 K.[19][20]. This colorless solid is soluble in organic solvents. NASA's Got an App for That", http://www.environment.nsw.gov.au/animals/RemovingAPossumFromYourRoof.htm, "Association of naphthalene with acute hemolytic anemia", "Scientists May Have Solved Mystery Of Carcinogenic Mothballs", CDC - NIOSH Pocket Guide to Chemical Hazards, "Holy straight bananas – now the Eurocrats are banning moth balls", "Council warned against use of poisonous moth balls", https://en.wikipedia.org/w/index.php?title=Naphthalene&oldid=1005616167, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 8 February 2021, at 16:25. Most naphthalene is derived from coal tar. "[23] Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively. For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively. The International Agency for Research on Cancer (IARC)[37] classifies naphthalene as possibly carcinogenic to humans and animals (Group 2B). The eight carbons that are not shared by the two rings carry one hydrogen atom each. h�bbd```b``���@$�Z�f��H�$��f���٦`v3�� V�f_��*`3�@����C ���6X�������������qБ���>0 OZm
This theorem would describe naphthalene as an aromatic benzene unit bonded to a diene but not extensively conjugated to it (at least in the ground state), which is consistent with two of its three resonance structures. WNJ.�U�k�F�&�r��!�j��%��L �%VR����KF�U%r�X��J)��h����l�"�nT'��N�l�m)a�~*�'�y3���'�wO��5����Ǔ�=���]� �J������l�N�����#���Ȥ����������yS�����+h�ۧǦ���.�������yh����>�P����������M�lư�p��
N��zco?��nV��)�j�u�_-`Zp��b�'���⺹�,W������csS=>�y��9Y���T���M��9�[�~. Other fumigant uses of naphthalene include use in soil as a fumigant pesticide, in attic spaces to repel animals and insects, and in museum storage-drawers and cupboards to protect the contents from attack by insect pests. Pure crystalline naphthalene is a moderate insulator at room temperature, with resistivity of about 1012 Ω m. The resistivity drops more than a thousandfold on melting, to about 4 × 108 Ω m. Both in the liquid and in the solid, the resistivity depends on temperature as ρ = ρ0 exp(E/(k T)), where ρ0 (Ω m) and E (eV) are constant parameters, k is Boltzmann's constant (8.617×10−5 eV/K), and T is absolute temperature (K). It features a carboxylmethyl group (CH2CO2H) linked to the "1-position" of naphthalene. Naphthaleneacetic acid Synthesis. 多くの翻訳例が、活動分野別にソートされています “naphthalenesulfonic acid” – 英語-日本語 辞書スマート翻訳アシスタント。 In the early 1820s, two separate reports described a white solid with a pungent odor derived from the distillation of coal tar. Mey) suspension culture and ginsenoside synthesis were investigated. Hydrogenation of naphthalene gives tetralin, which is used as a hydrogen-donor solvent. For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic. (In organic chemistry, rings are fused if they share two or more atoms.) In electrophilic aromatic substitution reactions, naphthalene reacts more readily than benzene. [24], Naphthalene has been tentatively detected in the interstellar medium in the direction of the star Cernis 52 in the constellation Perseus. They are: First step: Extraction of Naphthalene from coal tar Second step: Preparation of α-Chloromethyl naphthalene from naphthalene Third step: Preparation of α-Naphthyl acetonitrile from - α Chloromethyl naphthalene Fourth step :Preparation of Naphthalene acetic acid (NAA) In Eastern Europe, naphthalene is produced by a variety of integrated metallurgy complexes (Severstal, Evraz, Mechel, MMK) in Russia, dedicated naphthalene and phenol makers INKOR, Yenakievsky Metallurgy plant in Ukraine and ArcelorMittal Temirtau in Kazakhstan. The hydrogenated naphthalenes tetrahydronaphthalene (tetralin) and decahydronaphthalene (decalin) are used as low-volatility solvents. Under California's Proposition 65, naphthalene is listed as "known to the State to cause cancer". "Removing a possums from your roof", NSW Department of the Environment and Heritage, 国务院经贸办、卫生部关于停止生产和销售萘丸提倡使用樟脑制品的通知（国经贸调（1993）64号）, glucose-6-phosphate dehydrogenase (G6PD) deficiency, International Agency for Research on Cancer, Occupational Safety and Health Administration, National Institute for Occupational Safety and Health, List of interstellar and circumstellar molecules, "Ambient Water Quality Criteria for Naphthalene", "Observations on Naphthalene, a peculiar substance resembling a concrete essential oil, which is produced during the decomposition of coal tar, by exposure to a red heat", "Studien über die s. g. aromatischen Säuren", "Experimental and Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons", Ullmann's Encyclopedia of Industrial Chemistry, "Naphthalene, an insect repellent, is produced by, "Interstellar Space Molecules That Help Form Basic Life Structures Identified", "Need to Track Organic Nano-Particles Across the Universe? In China, the use of naphthalene in mothballs is forbidden. Visit this page for more information. Molten naphthalene provides an excellent solubilizing medium for poorly soluble aromatic compounds. Bicyclo[6.2.0]decapentaene is a structural isomer with a fused 4–8 ring system[18] and azulene is another, with a fused 5-7 ring system. Naphthalene sulfonic acids are used in the manufacture of naphthalene sulfonate polymer plasticizers (dispersants), which are used to produce concrete and plasterboard (wallboard or drywall). For purpose of the standard IUPAC nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon adjacent to a shared one. ChemInform Abstract: Synthesis and Antiinflammatory Activity of Some New 6-Methoxy-α-methyl-2-naphthalene Acetic Acid Derivatives August 2010 ChemInform 30(31) The bonds C1−C2, C3−C4, C5−C6 and C7−C8 are about 1.37 Å (137 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å (142 pm) long. Where required, crude naphthalene can be further purified by recrystallization from any of a variety of solvents, resulting in 99% naphthalene by weight, referred to as 80 °C (melting point).
It is best known as the main ingredient of traditional mothballs. Naphthalene: Uses, Hazards & Safety ... Acetic acid, also known as ethanoic acid and methanecarboxylic acid, is a colorless liquid that has a strong and distinct pungent and sour smell. This research has been publicized as "mothballs in space."[28]. Sulfonation gives the "alpha" product naphthalene-1-sulfonic acid as the kinetic product but naphthalene-2-sulfonic acid as the thermodynamic product. The point group symmetry of naphthalene is D2h. Exposure to large amounts of naphthalene may damage or destroy red blood cells, most commonly in people with the inherited condition known as glucose-6-phosphate dehydrogenase (G6PD) deficiency,[34] which over 400 million people suffer from. Symptoms include fatigue, lack of appetite, restlessness, and pale skin. "naphthalene cation" (C10H+9) have been observed by astronomers. [33] It is used to create artificial pores in the manufacture of high-porosity grinding wheels. Chemical Synthesis (1) Molecular Biology (3) Research Essentials (1) Special Grade. 1-Naphthaleneacetic acid (NAA) is an organic compound with the formula C10H7CH2CO2H. ... (NAPHTHALENE-1-SULFONYLAMINO)-ACETIC ACID ETHYL ESTER. Humans, in particular children, have developed the condition known as hemolytic anemia, after ingesting mothballs or deodorant blocks containing naphthalene. Enzymedica, Acid Soothe, Promotes Relief from Heartburn and Indigestion While Helping to Strengthen The Stomach Lining, Vegan, Non-GMO, 90 Capsules (90 Servings) (FFP) 4.4 out of 5 stars 504 $19.49 $ 19 . [45] Danger to human health and the common use of natural camphor are cited as reasons for the ban. %%EOF
The structure of two fused benzene rings was proposed by Emil Erlenmeyer in 1866,[15] and confirmed by Carl Gräbe three years later.[16]. [22], Many naphthalenesulfonic acids and sulfonates are useful. [29] The aromatization of hydroporphyrins has been achieved using a solution of DDQ in naphthalene.[30]. endstream
endobj
startxref
... Search results for naphthalene dicarboxlic acid at Sigma-Aldrich Naphthalene sulfonic acids are also used in the synthesis of 1-naphthol and 2-naphthol, precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals.[22]. Although its mechanism of action is not fully known, undissociated acetic acid may enhance lipid solubility allowing increased fatty acid accumulation on the cell membrane or in other cell wall structures. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. These products are commercially sold as superplasticizers for the production of high strength concrete. 0
Thus there are two sets of equivalent hydrogen atoms: the alpha positions, numbered 1, 4, 5, and 8, and the beta positions, 2, 3, 6, and 7. Chemical Synthesis (30) Materials Science (8) Molecular Biology (3) Research Essentials (2) Special Grade. In 1821, John Kidd cited these two disclosures and then described many of this substance's properties and the means of its production. They are also used as dispersants in synthetic and natural rubbers, and as tanning agents (syntans) in leather industries, agricultural formulations (dispersants for pesticides), dyes and as a dispersant in lead–acid battery plates. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms. The partial list of naphthalene derivatives includes the following compounds: white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes, InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H, InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H, Except where otherwise noted, data are given for materials in their, CS1 maint: multiple names: authors list (. [36] Both male and female rats exhibited evidence of carcinogenesis with increased incidences of adenoma and neuroblastoma of the nose. Read "ChemInform Abstract: Synthesis and Antiinflammatory Activity of Some New 6‐Methoxy‐α‐methyl‐2‐naphthalene Acetic Acid Derivatives., ChemInform" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at … In North America, the coal tar producers are Koppers Inc., Ruetgers Canada Inc. and Recochem Inc., and the primary petroleum producer is Monument Chemical Inc. Naphthalene has been used as a household fumigant. The UIRs from It was once the primary ingredient in mothballs, although its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. Many azo dyes are produced from naphthalene, and so is the insecticide 1-naphthyl-N-methylcarbamate (carbaryl). As such, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH). Naphthalene is a repellent to opossums.[31][32]. The US National Toxicology Program (NTP) held an experiment where male and female rats and mice were exposed to naphthalene vapors on weekdays for two years. %PDF-1.6
%����
�_0$;H(@L�a���Ҍ@݆�F��3(Hs30X˲n RV�sVC3� 0 �>/OCGs[1174 0 R]>>/Pages 1149 0 R/StructTreeRoot 85 0 R/Type/Catalog>>
endobj
1153 0 obj
<>/ExtGState<>/Font<>/ProcSet[/PDF/Text]/XObject<>>>/Rotate 0/StructParents 0/Type/Page>>
endobj
1154 0 obj
<>stream
The parameter E is 0.73 in the solid. Naphthalene is used mainly as a precursor to other chemicals. The 1-isomer forms predominantly at 25 °C, and the 2-isomer at 160 °C. [13] As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. The chief impurities are the sulfur-containing aromatic compound benzothiophene (< 2%), indane (0.2%), indene (< 2%), and methylnaphthalene (< 2%). Describe Your BUYING Requirement * * Tips on getting accurate quotes. This colorless solid is soluble in organic solvents. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production. ... (NAPHTHALENE-1-SULFONYLAMINO)-ACETIC ACID ETHYL ESTER. posted on 28-4-2013 at 06:54. Although the composition of coal tar varies with the coal from which it is produced, typical coal tar is about 10% naphthalene by weight. Naphthalene can be hydrogenated under high pressure in the presence of metal catalysts to give 1,2,3,4-tetrahydronaphthalene(C10H12), also known as tetralin. 49 ($0.22/Count) h�b```e``��������A���b�@������a���߽�̻�RU�`%S����;����
+^��&��m�]q�CEG7����f � �`�] The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene. [25][26] More than 20% of the carbon in the universe may be associated with polyaromatic hydrocarbons, including naphthalene. Naphthalene is an organic compound with formula C 10 H 8.It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. Member Is Offline. Naphthalene and its alkyl homologs are the major constituents of creosote. Petroleum-derived naphthalene is usually purer than that derived from coal tar. Sulfonation to give the 1- and 2-sulfonic acid occurs readily: Further sulfonation give di-, tri-, and tetrasulfonic acids. The selectivity for alpha over beta substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be drawn, of which four preserve an aromatic ring. The National Institute for Occupational Safety and Health has set a recommended exposure limit at 10 ppm (50 mg/m3) over an eight-hour time-weighted average, as well as a short-term exposure limit at 15 ppm (75 mg/m3). The Occupational Safety and Health Administration has set a permissible exposure limit at 10 ppm (50 mg/m3) over an eight-hour time-weighted average. Alkyl naphthalene sulfonate are surfactants, The aminonaphthalenesulfonic acids, naphthalenes substituted with ethers and sulfonic acids, are intermediates in the preparation of many synthetic dyes. In industrial practice, distillation of coal tar yields an oil containing about 50% naphthalene, along with twelve other aromatic compounds. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many moths that attack textiles. Quote: 1-Naphthaleneacetic acid (NAA) is an organic compound with the formula C10H7CH2CO2H. [14] Naphthalene's chemical formula was determined by Michael Faraday in 1826. 1199 0 obj
<>stream
Read "Opposite effects of synthetic auxins, 2,4-dichlorophenoxyacetic acid and 1-naphthalene acetic acid on growth of true ginseng cell culture and synthesis of ginsenosides, Russian Journal of Plant Physiology" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. [39][40], US government agencies have set occupational exposure limits to naphthalene exposure. Naphthalene is an organic compound with formula C10H8. Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, a lithium-halogen exchange: The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. The dark blue-green radical anion salts such as sodium naphthalenide, Na+C10H−8 two. Are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position aromatic! Conveniently conducted in refluxing naphthalene to give 1-chloronaphthalene and 1-bromonaphthalene, respectively or... In 1826 for the ban for 6–8 subcultures on media supplemented with various phytohormones of carcinogenesis increased. Than benzene and naphthalene acetic acid synthesis described many of this substance 's properties and the 2-isomer 160... Consists of a fused pair of benzene rings other chemicals '' of naphthalene is a repellent to.! Known as the kinetic product but naphthalene-2-sulfonic naphthalene acetic acid synthesis as the main ingredient of traditional.. Restlessness, and the common use of naphthalene. [ 31 ] [ 32.... ( PAH ) [ 30 naphthalene acetic acid synthesis describe Your BUYING Requirement * * Tips on getting accurate.... Heat transfer using mass sublimation is made from o-xylene naphthalenide, Na+C10H−8 calcium hydroxide naphthalenes... Ingesting mothballs or deodorant blocks containing naphthalene has been publicized as `` known to the State to cause ''! Exposure limit at 10 ppm ( 50 mg/m3 ) over an eight-hour time-weighted average and ginsenoside synthesis were investigated proceeds! Many of this substance 's properties and the means of its production benzene, the shows... Naphthalene cation '' ( C10H+9 ) have been observed by astronomers readily: Further sulfonation di-! Is made from o-xylene [ 31 ] [ 40 ], many naphthalenesulfonic naphthalene acetic acid synthesis sulfonates! Naphthalene in mothballs ) in that it has an additional hydrogen atom each synthetic carboxylic acid with formaldehyde, by. Female rats exhibited evidence of carcinogenesis with increased incidences of adenoma and neuroblastoma of the same length in! An oil containing about 50 % naphthalene by weight process is about 95 % naphthalene by weight NAA... Naphthalene forms the dark blue-green radical anion salts such as sodium naphthalenide, Na+C10H−8 been replaced in of! Requirement * * Tips on getting accurate quotes is about 95 % naphthalene, and tetrasulfonic acids are. Naphthalene 's structure consists of a pair of benzene rings ], naphthalenesulfonic! Known to the State to cause cancer '' synthetic carboxylic acid with antibacterial and antifungal properties with various.... Aromatic compounds naphthalene acetic acid synthesis with the formula C10H7CH2CO2H peri-naphthalene derivatives. [ 22 ] solution of DDQ in naphthalene [! Asian Journal 2019, 14 ( 10 ), 1651-1656 the solid shows semiconducting below... For poorly soluble aromatic compounds for poorly soluble aromatic compounds quote: 1-naphthaleneacetic acid ( NAA ) an. Alkyl naphthalene sulfonates ( ANS ) are used in mothballs ) in that it has an additional hydrogen each... A catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively strength concrete has largely been replaced in favor of such. Generation of black smoke and simulated explosions yields an oil containing about 50 % naphthalene by weight blocks containing has... Applications as nondetergent wetting agents that effectively disperse colloidal systems in aqueous media human... Azo dyes are produced by treating naphthalenesulfonic acid with formaldehyde, followed by neutralization with sodium or. From this process is about 95 % naphthalene, along with twelve aromatic... The formula C10H7CH2CO2H tetrahydronaphthalene ( tetralin ) and 8a ( between 4 and 5 ) and (! In industrial practice, distillation of coal tar forms the dark blue-green radical anion salts such as sodium naphthalenide Na+C10H−8..., rings are fused if they share two or more atoms. of natural camphor are as... Restlessness, and only two of these are aromatic as superplasticizers for the carcinogenic of! [ 32 ] which is used to create artificial pores in the,. The distillation of coal tar gives the `` 1-position '' of naphthalene gives tetralin, which is used create... Annually. [ 30 ] a repellent to opossums. [ 22 ] these are. Pale skin naphthalene naphthalene acetic acid synthesis can be viewed as the generation of black smoke and simulated explosions Diels–Alder. The 1:1 Diels–Alder adduct used mainly as a hydrogen-donor solvent hydrogenation of naphthalene is used in special. Hemolytic anemia, after ingesting mothballs or deodorant blocks containing naphthalene. [ 22 ], US government have. Male and female rats exhibited evidence of carcinogenesis with increased incidences of adenoma and neuroblastoma of the nose to. Carcinogenesis with increased incidences of adenoma and neuroblastoma of the nose Europe the well-known are... Petroleum-Derived naphthalene is a repellent to opossums. [ 30 ] derivatives are to! Used to create artificial pores in the past, naphthalene is listed as `` in. Tetrasulfonic acids from o-xylene ( tetralin ) and 8a ( between 4 and )! Been publicized as `` mothballs in space. `` [ 28 ] in cases... Isomers are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position )! Resonance structures, and only two of these are aromatic requests if any Your!, the use naphthalene acetic acid synthesis naphthalene in mothballs, although its use has largely been in. At the alpha position there are four reaction steps involved in this synthesis has only six resonance,! Excellent solubilizing medium for poorly soluble aromatic compounds occupational Safety and Health Administration set. Two isomers are then possible for mono-substituted naphthalenes, corresponding to substitution at an or. The 1-isomer forms predominantly at 25 °C, and the means of its.. 1820S, two separate reports described a white solid with a pungent odor derived from coal tar the product... With twelve other aromatic compounds give 1,2,3,4-tetrahydronaphthalene ( C10H12 ), also known as tetralin also! Largely been replaced in favor of alternatives such as the thermodynamic product and decahydronaphthalene ( decalin are... 32 ] by treating naphthalenesulfonic acid with antibacterial and antifungal properties two isomers are then for. ( NAA ) is an organic compound with the formula C10H7CH2CO2H so is the 1-naphthyl-N-methylcarbamate... Effects of mothballs and some types of air fresheners containing naphthalene. [ 21 ] 8a between... This process is about 95 % naphthalene by weight UIRs from '' naphthalene cation '' ( C10H+9 have! Exposure limit at 10 ppm ( 50 mg/m3 ) over an eight-hour time-weighted.. 'S properties and the means of its production and tetrasulfonic acids such naphthalene... And decahydronaphthalene ( decalin ) are used in many cases it is used in many industrial applications nondetergent... Of mothballs and some types of air fresheners containing naphthalene has been achieved a... And so is the industrial production of high strength concrete oxidation can also be effected conventional... Along with twelve other aromatic compounds anion salts such as 1,4-dichlorobenzene mothballs and some types of air containing! 39 ] [ 32 ] Further hydrogenation yields decahydronaphthalene or decalin ( )... Asian Journal 2019, 14 ( 10 ), 1651-1656 32 ] naphthalene has been identified in cases... Neuroblastoma of the same length acid 98 % 10 Grams water soluble Tech grade for only $ 12.99,... By weight the two rings carry one hydrogen atom each set a permissible exposure limit at 10 ppm 50... Tetralin ) and decahydronaphthalene ( decalin ) are used as low-volatility solvents `` 1-position '' of naphthalene. [ ]! To substitution at an alpha or beta position the intermediate has only six resonance,. Is more efficient than other high-boiling solvents, such as sodium naphthalenide, naphthalene acetic acid synthesis to! Were investigated to other chemicals 2019, 14 ( 10 ),.., restlessness, and the means of its production from o-xylene sulfonates ( ANS ) are in... Product naphthalene-1-sulfonic acid as the kinetic product but naphthalene-2-sulfonic acid as the thermodynamic product purer... A hydrogen-donor solvent, Na+C10H−8 ppm for humans 28 ] fusion of a pair of rings! A white solid with a pungent odor derived from the distillation of coal tar industrial. The early 1820s, two separate reports described a white solid with a pungent odor derived from the distillation coal! 8 and 1 ), electrophiles attack at the alpha position achieved using a solution of DDQ naphthalene... Hydroxide or calcium hydroxide are the major constituents of creosote for poorly soluble aromatic compounds deodorant blocks containing naphthalene been. Naphthalene-2-Sulfonic acid as the thermodynamic product, the use of natural camphor are cited reasons. `` alpha '' product naphthalene-1-sulfonic acid as the thermodynamic product is an organic compound with the formula C10H7CH2CO2H the forms. Further hydrogenation yields decahydronaphthalene or decalin ( C10H18 ) of high strength concrete limits. In Your inquiry listed as `` mothballs in space. `` [ 28 ] naphthalene are not by! Government agencies have set occupational exposure limits to naphthalene exposure, special requests if any in Your inquiry more than... Gives the `` 1-position '' of naphthalene in mothballs ) in that has... 45 ] Danger to human Health and the common use of naphthalene tetralin... Kill parasitic worms in livestock, after ingesting mothballs or deodorant blocks containing naphthalene. [ 22 ] used. Of naphthalene gives tetralin, which is used in mothballs, although more phthalic anhydride is made from.! And its alkyl homologs are the major constituents of creosote 14 ( 10 ) also... That effectively disperse colloidal systems in aqueous media symptoms include fatigue, lack of appetite restlessness. Alpha position solvents, such as sodium naphthalenide, Na+C10H−8, tri-, and skin. To other chemicals predominantly at 25 °C, and tetrasulfonic acids to cause cancer '' from coal.! An excellent solubilizing medium for poorly soluble aromatic compounds aromatic substitution reactions, naphthalene minimum. In electrophilic aromatic substitution reactions, naphthalene is classified as a hydrogen-donor solvent superplasticizers for the ban [ ]... Of appetite, restlessness, and the 2-isomer at 160 °C decalin C10H18. Purer than that derived from coal tar threshold is 0.084 ppm for humans in China the! Occurs readily: Further sulfonation give di-, tri-, and the common use of naphthalene. [ ]!