A2, Designated state(s): 2017-02-16T10:10:56+01:00 This composition is color stabilized and cosmetically elegant. The toxicology of hydroquinone - relevance to occupational and environmental exposure. [21][25][23] NTP evaluation showed some evidence of long-term carcinogenic and genotoxic effects[26], While hydroquinone remains widely prescribed for treatment of hyperpigmentation, questions raised about its safety profile by regulatory agencies in the EU, Japan, and USA encourage the search for other agents with comparable efficacy. STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN. Solubility of Hydroquinone in Different Solvents from 276.65 K to ChemPoint will not under any circumstances release personal user information to individuals or companies. Place an order online, track your orders, download SDS and TDS, and see your quotes, all in one secure place. Data 51, 16681671 (2006), C. L. Yaws, S.-C. Lin, Enthalpy of fusion at freezing pointOrganic compounds, in Thermophysical Properties of Chemicals and Hydrocarbons, William Andrew Publishing (Elsevier, 2009), pp. volume42, Articlenumber:1 (2021) Conversion factors (at 25 oc and normal atmospheric pressure) 1 ppm = 4.5 mg!m 3 Re: How to dissolve Hydroquinone to make 4 oz. 109. The Molecular Weight is 110.11 g/mol. 15, 188196 (1996), U. Domaska, Fluid Phase Equilib. 0000005306 00000 n Hydroquinone is highly susceptible to ring substitution by Friedel-Crafts reactions such as alkylation. All Rights Reserved, View All Eastman Hydroquinone USP Articles. While the hydroquinone is effective for the pigmentation disorder treatment, retinoid is used for its skin treatment benefits. Heat Mass Transf. NR 1L~tyj|ZZ3]jFlszH#bd]="nVj =rBF-=Y?Pe 3(\[3;wR-+7Fn ~pSQ(Rpiw^zYr''t@\vobE]u'C}io0q;^k5C@|zZNNA>,XOrztV;qO*w:MC$OI\_$Io 'v [ By rejecting non-essential cookies, Reddit may still use certain cookies to ensure the proper functionality of our platform. Compositions according to this invention may include dermatologically acceptable carriers. Hydroquinone occurs in the environment as a result of anthropogenic processes, as well as in natural products from plants and animals. Thermodyn. Hydroquinone occurs as fine, white needles. vz >I d50dwp?i4,H3. Diamines, useful in the rubber industry as antiozone agents, are similarly produced from aniline: Hydroquinone has a variety of uses principally associated with its action as a reducing agent that is soluble in water. Some products also contain sunscreens. Editor's Rating: . I can't use water because I cannot dissolve enough Hydroquinone into it to reach the desired concentration. endstream endobj 1 0 obj <> endobj 2 0 obj <> endobj 12 0 obj <>stream 2005 Wiley-VCH, Weinheim. These phases (described below) are combined in a mixing tank with an in-line homogenizer as follows. [33], Hydroquinone has been shown to be one of the chemical constituents of the natural product propolis. Reference Tables: SOLUBILITIES - uspbpep.com Water Solubility 73000 mg/L at 25C 2.6B pH pKa 4.0 - 4.7 pK1 = 9.9 2.12 Oxidation:Reduction Potential +286 mV at 25C and pH 7 ENVIRONMENTAL FATE/BIODEGRADATION The amount of crosslinking was controlled by the reaction conditions, including temperature, reaction time, and . In the environment, hydroquinone showed increased toxicity for aquatic organisms, being less harmful for bacteria and fungi. Calorim. It would be desirable to combine the pigmentation disorder treatment with this skin benefit ingredient in one composition. Treatment with hydroquinone interferes with the action of tyrosinase, which is an enzyme used in the synthesis of melanin, and compositions are sold across the counter at about 2% hydroquinone and by prescription at higher concentrations. 20, 14331442 (1986), G. Wienke, J. Gmehling, Toxicol. nQt}MA0alSx k&^>0|>_',G! 49, 313321 (2015). Retinoids are included in the invention from about 0.01 to about 5%, preferably from about 0.025% to about 2.0%, more preferably from about 0.05% to about 1%, and most preferably from about 0.025% to about 0.5%. ~lgM~Gc{1S_1Q/_/v">S 9 Solubility of Hydroquinone in Different Solvents from 276.65 K to 345. J. Azelaic acid - Wikipedia The solubility in water is 6.72g/L. We have found that a cream containing 5% of hydroquinone and 0.05 % of laevo-ascorbic acid remains white, and the emulsion remains unbroken after many months of storage, The laevo-ascorbic or cevitamic acid is pr'eferably employed in the free condition; but if desired, the salts, and especially the water-soluble salts thereof, may be employed . Recent pieces of . The natural pH for conventional hydroquinone compositions is acidic, generally less than about 4 even though this is harsh to the skin and to other components of the product. One of these, 4-butylresorcinol, has been proven to be more effective at treating melanin-related skin disorders by a wide margin, as well as safe enough to be made available over the counter. Glycerol derivatives solubilise natural, hydrophilic antioxidants in biofuels. https://doi.org/10.1007/s10765-020-02750-4, DOI: https://doi.org/10.1007/s10765-020-02750-4. The experimental solubility data was well-correlated with the data, calculated by . Eng. 0 7 r @ &. 114, 175188 (1996), I. Hahnenkamp, G. Graubner, J. Gmehling, Int. Hydroquinone (C6H4(OH)2), also known as benzene-1,4-diol or quinol, is an aromatic organic compound, with a variety of uses in chemistry. An improvement in the color stability of the 4% hydroquinone compositions is seen at and above 2.0% magnesium ascorbyl phosphate in the 6-7 pH range. Protected retinoid, with its skin benefit capabilities, may also be included with the hydroquinone composition. EP, Kind code of ref document: Hydroquinone, 99.5%, Thermo Scientific Chemicals Using a laser-monitoring observation technique, the solubility of hydroquinone in water, methanol, ethanol, 2-propanol, ethyl acetate, butyl acetate, and acetic acid were measured at temperatures ranging from 276.65 K to 345.10 K under the atmospheric pressure. 0000053439 00000 n [O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(O)=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1, OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C, Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE, CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O, [(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2H-furan-4-yl] dihydrogen phosphate, [Na+]. The present invention is not to be limited by any mechanism described in the specification, because it is defined by the claims. A further embodiment of the invention includes a method for stabilizing a hydroquinone composition (with about 1% to about 12% hydroquinone, preferably about 2% to about 10%, more preferably about 2% to about 8%, and most preferably about 3% to about 4%) with a neutral pH of from about 5.5 to about 8.0, more preferably a pH of from about 5.5 to about 7.5, and most preferably at a pH of from about 6.0 to about 7.5, by adding a water-soluble antioxidant, preferably sulfite, including but not limited to sulfites, bisulfites, metabisulfites, their salts and their derivatives, most preferably sodium metabisulfite, and a cationic salt of acidic ascorbyl esters, preferably sodium ascorbyl phosphate, more preferably aminopropyl ascorbyl phosphate, most preferably magnesium ascorbyl phosphate. PDF HYDROQUINONE - Centers for Disease Control and Prevention Hope it helps 6 yrs later. If youd like my help or recipes for this bleaching cream please contact me on Instagram @kaylinell and @kay.linell or Facebook at kay linell. For use herein, the encapsulation forms a protective system to prohibit or inhibit the oxidation of the retinoid. The drug is freely soluble in water and in alcohol. Eng. An acceptable carrier also possesses suitable aesthetic and cosmetic qualities and may include emollients, conditioners and the like. wG xR^[ochg`>b$*~ :Eb~,m,-,Y*6X[F=3Y~d tizf6~`{v.Ng#{}}jc1X6fm;'_9 r:8q:O:8uJqnv=MmR 4 Magnesium ascorbyl phosphate (also called magnesium ascorbityl phosphate or magnesium L-ascorbyl-2-phosphate) has a chemical formula of C. In another embodiment, sodium metabisulfite and magnesium ascorbyl phosphate are used in about 0.01% (preferably from about 0.05% to about 0.5%, most preferably at least about 0.1%,) and about 0.5% (preferably from about 0.25% to about 3%, more preferably from about 0.25% to about 1%, and most preferably at least about 0.5%) respectively in a composition with about 4% hydroquinone. Hydroquinone is soluble in alcohol solvents such as ethanol and methanol [17]. For more information, please see our Int J Thermophys 42, 1 (2021). Tests, which results are detailed in the following two tables, are performed at 5C and 40C for certain percentages of magnesium ascorbyl phosphate at specific pHs. Approximate Solubilities of USP and NF Articles, methanol, 13; ethyl acetate, >10,000; hexanes, >10,000, 0.1 N hydrochloric acid, 1; 0.1 N sodium hydroxide, 1, boiling alcohol, 50; boiling chloroform, 80; acetone at 50, methanol, 3; isopropanol, 69; benzene, 2500; petroleum ether, 5000, dimethylformamide, 10; 10 N sodium hydroxide, 3.5, dimethylacetamide, 2; dimethylformamide, 3.5; dimethylsulfoxide, 3.5, 0.1 N hydrochloric acid, 2500; 0.1 N sodium hydroxide, 100, isopropyl alcohol, 4; propylene glycol, 9; methanol, 5.3, isopropyl alcohol, 1408; propylene glycol, 119; methanol, 75, alcohol solution (1 in 2), 2; diethylphthalate, <1; benzyl benzoate, <1, acetone, 100; methanol, 1000; 0.1 N hydrochloride acid, >1000, absolute alcohol, 8; methanol, 8; propylene glycol, 19, pyridine, 10; methanol, 71; acetone, 130; methylene chloride, 286; toluene, 2000; dioxane, 2000, carbon disulfide, 2 (slowly and usually incompletely), carbon disulfide, 2 (slowly and usually incompletely) olive oil, 100, methylenedichloride, 43; 4-methyl-2-pentanone, 100. Will glycerol and citric acid react? If yes, under what conditions? If you are already a ChemPoint customer then sign up for access to our online ordering website. Toxicol. Variations in pH have proven to result in excessive discoloration ranging from brownish to black. ;O,1Y+%8#oKT^VWtew4>@V.SR :hmBZ>#ey!UC5! / /n At 40C, 4% hydroquinone compositions have the same color stability with slightly more sodium metabisulfite, at least about 0.01% at about 3.5 to about 4.0 pH; at least about 0.05% sodium metabisulfite at about 4.5 to about 6.0 pH; and at pH; at least about 0.05% sodium metabisulfite at about 4.5 to about 6.0 pH; and at least about 0.10% sodium metabisulfite at about 6.5 to about 7.0 pH. Antioxidants in the hydroquinone phase and inorganic or amino acyl cationic salts of acidic ascorbyl esters, preferably sodium metabisulfite and magnesium ascorbyl phosphate respectively, are effective in stabilizing such hydroquinone compositions, which are used in treatment of pigmentation disorders. Eastman has active ingredients, thickeners, plasticizers, film formers, and more for your personal care formulations. It is understood that while the invention has been described in conjunction with the detailed description thereof, that the foregoing description is intended to illustrate and not limit the scope of the invention, which is defined by the scope of the appended claims. It is a reducmg agent that is reversibly oxidized to semiquinone and quinone. Chem. Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Except where otherwise noted, data are given for materials in their, Hydroquinone oxidation with V2O5/NaClO3/H2SO4, http://www.sciencemadness.org/smwiki/index.php?title=Hydroquinone&oldid=11523, Articles containing unverified chemical infoboxes, GNU Free Documentation License 1.3 or later. Cat No. : H329-500 0000002585 00000 n Bioaccumulative potential Hydroquinone (123 -31 -9) Bioaccumulative potential Not established. Stir until uniform. 4]DYR@'c antiphlogistics and cardiaca, Cosmetics or similar toilet preparations characterised by the composition, Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients, Sulfur; Selenium; Tellurium; Compounds thereof, Cosmetics or similar toilet preparations characterised by the composition containing organic compounds, Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen, . GHS H Statement: Causes serious eye damage.Suspected of causing genetic defects.May cause an allergic skin reaction.Suspected of causing cancer.Harmful if swallowed.Very toxic to aquatic life. How to dissolve Hydroquinone to make 4 oz. With respect to organic solvents, the solubility varies from 57% in ethanol to less than 0.1% in benzene. Classical photo shops . D-170D Solubility of EASTMAN Hydroquinone and Derivatives Subject: Hydroquinone and hydroquinone derivatives listed in this publication are used as intermediates for manufacturing a variety of products and as polymerization inhibitors for vinyl monomers and unsaturated polyester resins. 230, 176183 (2005), A. Apelblat, E. Manzurola, N. A. Balal, J. Chem. 0000008514 00000 n Belhachemi, B., Makhlouf, H. & Belhachemi, M.H. In hydroquinone and sodium metabisulfite compositions, it is believed that the sodium metabisulfite oxidizes first and delays the start of any oxidation of the hydroquinone, so that excessive discoloration is delayed or totally avoided. It is not to be considered as either a warranty or quality specification. 388, 7381 (2010), H. Li, G. Hu, F. Guo, L. Zhao, J. Zhu, Y. Zhang, Can. Cite this article. The present invention addresses the problem of excessive discoloration in hydroquinone compositions of a neutral pH. Appearance: Free-flowing white crystalsOdor: OdorlessMolecular weight: 110.11Empirical formula: C6H6O2Assay (Anhydrous basis): 99.0-100.5 %Melting point: 172-174CWater: 0.5 wt % max.Residue on ignition: 0.5 % maxSolubility: Moderately soluble in water, glycerin, propylene glycol, and highly soluble in ethanol, Can work in conjunction with glycolic acid to help reduce pigment in melasma Non-GMOExtremely low vapor pressureUSP GradeEuropean Pharma GradeDrug master file available upon request. It is a major component in most black and white photographic developers for film and paper where, with the compound metol, it reduces silver halides to elemental silver. It is a reducing agent that is reversibly oxidized to semiquinone and quinone. Monobenzone: Uses, Interactions, Mechanism of Action - DrugBank The solubilities in binary and ternary systems of hydroquinone (1,4-dihydroxybenzene) and p-quinone (1,4-benzoquinone) in supercritical carbon dioxide were measured in the pressure range 10.0 to 35.0 MPa at temperatures of 333, 348 and 363 K.In binary systems, the solubility of hydroquinone was three orders of magnitude lower than that of p-quinone. Can be destroyed by oxidizing it with an oxidizing mixture. The preferred protected retinoid is in the form of small beads or vesicles which are of a form that can be adjusted to be incorporated into varied topical compositions. Rev. Hydroquinone: Environmental Pollution, Toxicity, and Microbial Answers endstream endobj 276 0 obj <>stream Van Haelst, P. Heesen, F. Van Der Wielen, H. Govers, Chemosphere 29, 16511660 (1994), Article One skilled in the art is familiar with the known protective system technologies, such as encapsulation and entrapment methodologies. The Beaver: Its Life and Impact. Eastman Hydroquinone, USP, meets or exceeds the requirements of the United States Pharmacopoeia and is produced under conditions of current good manufacturing practices (cGMP). InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H, InChI=1/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H, Except where otherwise noted, data are given for materials in their. Methods and products for nucleic acid production and delivery, Nucleic acid product and its administration method, Nucleic acid product and method of administration thereof, Compositions and systems for the treatment of hyperpigmentation, Methods for prevention of post-inflammatory hyperpigmentation, Skin care compositions containing retinoids, Improved method for stability of ageing comprising thirosinase inhibitor activity, Use of ascorbic acid to reduce irritation of topically applied active ingredients, COSMETIC COMPOSITIONS WITH ANTIMICOTIC PROPERTIES, EFFECTIVE AGAINST PSORIASIS AND HAIR LOSS AND COSMETIC METHOD FOR, Treatment or prevention of undesired skin pigmentation, Skin care compositions and method of improving skin appearance, Ultrasound enhancement of percutaneous drug absorption, Skin whiteners containing hydroxytetronic acid, Stabilized retinoid-containing skin care compositions, Retinoid compositions containing a water soluble antioxidant and a chelator, Composition and method for treating rosacea and sensitive skin with free radical scavengers, Skin care compositions containing imidazoles and retinoids, Stable compositions containing a retinoid and an enzyme based antioxidant system, Self-tanning compositions containing dha and propolis extract, Composition and process for stabilizing oxygen-unstable species, Bleaching preparation and cosmetic for preventing and improving aging of skin, Composition and method for the treatment of pigmentation disorders, Composition for cosmetic or pharmaceutical use, Remedies for pigmentation and melanocyte proliferation inhibitors, Public reference made under article 153(3) epc to a published international application that has entered the european phase, Divisional application: reference to earlier application, Information on the status of an ep patent application or granted ep patent. Cationic salts of acidic ascorbyl esters, including inorganic salts, preferably magnesium ascorbyl phosphate, and amino acyl derivatives, preferably aminopropyl ascorbyl phosphate, are preferred in this invention. ORIGINAL CODE: 0009013, Ref document number: The document was not able to download due to an unknown error. Hydroquinone Revision Date 24-Dec-2021 General Advice If symptoms persist, call a physician. Hydroquinone - an overview | ScienceDirect Topics Ferulic acid 0.5% 0.15g. 0000002198 00000 n The composition is preferably formulated in separate phases as designated below. 0000002544 00000 n Azelaic acid (AzA) is a organic compound with the formula HOOC(CH 2) 7 COOH. As a polymerisation inhibitor, exploiting its antioxidant properties, hydroquinone prevents polymerization of acrylic acid, methyl methacrylate, cyanoacrylate, and other monomers that are susceptible to radical-initiated polymerization. 420, 2429 (2016), W. E. Acree Jr, Thermochim Acta 189, 3756 (1991), F. L. Nordstrm, . C. Rasmuson, J. Chem. vitamin C; Salts thereof, Medicinal preparations containing active ingredients not provided for in groups A61K31/00-A61K41/00, Mixtures of active ingredients without chemical characterisation, e.g. Chem. 330, 4851 (2012), A. Shalmashi, A. Eliassi, J. Chem. Hydroquinone is a white crystalline solid, poorly soluble in water, but more soluble in organic solvents. Chemically, hydroquinone is designated as p-dihydroxybenzene; the empirical formula is C 6 H 6 O 2; molecular weight is 110.0. 0000002221 00000 n Some hydroquinone compositions include antioxidants, such as ascorbyl palmitate. Solubility of Hydroquinone : r/OrganicChemistry Color stability improvement is evident at all levels. A specific embodiment of the invention is listed in the following table. J. Chem. Airborne hydroquinone may be oxidized to quinone at ordinary . Exceptional antioxidant qualities are seen at 0.10% (all percentages in the application are weight percent) and above, preferably from about 0.05% to about 0.5% for sodium metabisulfite. V)gB0iW8#8w8_QQj@&A)/g>'K t;\ $FZUn(4T%)0C&Zi8bxEB;PAom?W= stearic, palmitic, arachidic acids, Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. Retinoids, in particular retinoic acid, retinal, and their derivatives, isomers and analogs (such as adapalene, tazarotene and isotretoin), are beneficial for improving rough skin texture, mottled pigmentation, sallow complexion, lines and wrinkles. Found. The process of making a stable hydroquinone composition having a pH of about 5.5 to about 8.0 comprising: combining the following ingredients, in a carbon dioxide atmosphere: first, magnesium ascorbyl phosphate and sodium metabisulfite, then, third, magnesium ascorbyl phosphate, then, Application filed by Medicis Pharmaceutical Corp, [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O*, OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C, 3-aminopropyl [(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2H-furan-4-yl] hydrogen phosphate, NCCCOP(O)(=O)OC1=C(O)[C@@H]([C@@H](O)CO)OC1=O, OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C, OC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C, trisodium;[(5R)-5-[(1S)-1,2-dihydroxyethyl]-2-oxido-4-oxofuran-3-yl] phosphate, [Na+].[Na+]. It is moderately soluble in water and highly soluble in alcohol. 58 / Monday, March 26, 2012 / Rules and Regulations 10/31/2017 EN (English US) 6/8 12.3. It is soluble in water. Anal. All information collection is solely used to support ChemPoint customers service communications. PDF HYDROQUINONE HEALTH AND SAFETY GUIDE - World Health Organization The obtained results show that the . The solubilities of benzoic acid, salicylic acid, resorcinol and hydroquinone in water and in 1-octanol were measured by the dynamic method which is also called the synthetic method from 297.25 K to 334.45 K. Using differential scanning calorimetry (DSC Q2000 and SDT Q600), the melting temperature and the enthalpy of fusion of these solutes were determined. Determination and Correlation of Solubilities of Benzoic Acid, Salicylic Acid, Resorcinol and Hydroquinone in Water and in 1-Octanol at Temperatures from 297.25K to 334.45K. Hydrquinone Cas N: 123-31-9 - Oecd 0000002379 00000 n It is also used to prepare 2% bleaching creams and certain intermediates for the synthesis of dyes, and it has some activity as an antitumoragent. This is a preview of subscription content, access via your institution. Some may double boil the hydroquinone and ester, I was too scared of the possibility of combustion. The preferred form of protected retinol is manufactured by SunSmart (also known as Particle Sciences, Inc. of Bethlehem, PA) under the brand name of SunCaps A-1283. It does not have the same predisposition to cause dermatitis as metol does. Tests, which results are detailed in the following two tables, are performed to show how well sodium metabisulfite ("SMBS") stabilizes color at each pH at 5C and 40C in 4% hydroquinone ("HQ") compositions. 0000008435 00000 n Protected retinoid may be added to these compositions for additional skin benefit effects. Obagi Nu-Derm Clear (Hydroquinone USP, 4%) Skin Bleaching Cream Obagi One embodiment of the invention is a composition which comprises hydroquinone (about 1% to about 12%, preferably about 2% to about 10%, more preferably about 2% to about 8%, more preferably with about 2% to about 4%, and most preferably about 3% to about 4%) and has a neutral pH of from about 5.5 to about 8.0, more preferably a pH of from about 5.5 to about 7.5, and most preferably at a pH of from about 6.0 to about 7.5. The FDA had classified hydroquinone in 1982 as a safe product - generally recognized as safe and effective (GRASE), however additional studies under the National Toxicology Program (NTP) were suggested in order to determine whether there is a risk to humans from the use of hydroquinone. The color stability of the hydroquinone composition is promoted by one or more antioxidants in the hydroquinone phase, preferably sulfite, including but not limited to sulfites, bisulfites, metabisulfites, their salts and their derivatives, most preferably sodium metabisulfite, and a cationic salt of acidic ascorbyl esters, most preferably magnesium ascorbyl phosphate. However, hydroquinone discolors at the pH range of 7.0 to 8.5. HlRMo0WB:NnVCnE4(i0 (1* )@NzHR!>i;8XaXnsO0LNT0l$B%"NAb0I9V *6/-\vn0W"fKF:AAgl:psRZ?k`&eB IUQ0ET;W#vL=@XwRG{-LHlTz]^s%OB(GF 11'I Thank you for your inquiry and interest in ChemPoint. Availability. Solubility of Hydroquinone in Different Solvents from 276.65 K to 345. This website uses cookies. 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Do not put this product in the microwave. 0000000731 00000 n Consistent with a condensation reaction, water was determined to be the primary byproduct. 0000003660 00000 n The solubility was increased by addition of ethanol, reached a maximum . Solubilities of hydroquinone and p-quinone in - ScienceDirect