[ CAS No. 20427-59-2 ] {[proInfo.proName]}

Name: 20427-59-2|Cuprichydroxide|99%
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CAS No. :	20427-59-2	MDL No. :	MFCD00010968
Formula :	CuH₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AEJIMXVJZFYIHN-UHFFFAOYSA-N
M.W :	97.56	Pubchem ID :	30154
Synonyms :

Safety of [ 20427-59-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P260-P264-P270-P271-P273-P280-P284-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P391-P403+P233-P405-P501	UN#:	3288
Hazard Statements:	H302-H318-H330-H410	Packing Group:	Ⅱ
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 20427-59-2 ]
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[ 20427-59-2 ] Synthesis Path-Upstream 1~2

1
[ 20427-59-2 ]
[ 57-11-4 ]
[ 660-60-6 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, [2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1938, vol. 207, p. 1097 - 1099
[3] , Gmelin Handbook: Cu: MVol.B2, 44, page 715 - 717,

2
[ 1493-13-6 ]
[ 20427-59-2 ]
[ 34946-82-2 ]

Reference： [1] C.A., 1972, vol. 76, p. 112691
[2] C.A., 1976, vol. 84, p. 58630
[3] , Gmelin Handbook: F: PerFHalOrg.SVol.3, 6.2.3.1, page 48 - 120,
[4] Inorganic Chemistry, [5] Inorganic Chemistry, 1981, vol. 20, p. 2438 - 2448

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Yield	Reaction Conditions	Operation in experiment
	In water addn. of an aq. soln. of 15g CuCL2*2H2O to 350ml 1.5n-NaOH in the cold while stirring, washing several times with boiled H2O, filtration (exclusion of CO2), drying in vac. for several times;; contents traces of Cl(1-);;
	With sodium dodecylbenzenesulfonate In water CuCl2*2H2O, sodium dodecyl benzenesulfonate and NaOH (2:1:40) dissolved in H2O under stirring, crystd. in air for several h; ppt.separated, washed, dried, XRD;
	In water addn. of an aq. soln. of 15g CuCL2*2H2O to 350ml 1.5n-NaOH in the cold while stirring, washing several times with boiled H2O, filtration (exclusion of CO2), drying in vac. for several times;; contents traces of Cl(1-);;

	In water aq. CuCl2 added dropwise to aq. NaOH under magnetic stirring at 20 °C, aged for 20 min; product centrifuged, washed (H2O, etahnol), dried (oven, 2 h, 60 °C); detd. by XRD;
	In water mixed, pptd.;
	In water equimolar amts. of aq. solns. of CuCl2*2H2O and NaOH stirred for 10 min at room temp.; filtered;
	With polyethylene glycol In water	All of the chemical reagents used in this experiment were analytical grade. Cu2O was synthesized as follows: 200mg of polyethylene glycol (PEG, Mw 20 000) and 180mg of copper(II) chloride dehydrate (CuCl2·2H2O) were dissolved in 200mL H2O, which was stirred with a magnetic stirrer. This solution was stirred for 30min to ensure that the PEG and CuCl2 completely dissolved. Then, 2mL of 6M NaOH was added dropwise to the solution of CuCl2 and PEG under constant stirring. A blue precipitate of Cu(OH)2 was rapidly produced.
	In ethanol; water
	With sodium chloride In water for 0.0833333h;
	In water	Synthesis of cubic Cu₂O nanoparticles Nanodomain Cu2O was synthesized as follows. To the aqueous solution of CuCl2 (0.01 M, 100 mL), NaOH (0.2 M, prepared in water, 10 mL) was added dropwise under slow stirring. The colour of the solution was noticed to be changed gradually from green to blue due to the formation of Cu(OH)2. Glucose (1 M, 10 mL) in water was then added slowly into it and stirring was allowed to continue at 60 °C for 1 h more. The color of the precipitates gradually changed from green to yellow which indicates the formation of Cu2O nanoparticles. The solution was then allowed to settle for 1 h. These allow complete nucleation of the particles. It was then centrifuged, followed by repeated washing with water and ethanol. The particles were dried under vacuum before use.
	In water	The Cu(dmha)2 complex (2) was synthesized using the procedure described in [14]. Aqueous solutions of CuCl22H2O (1.296 g, 7.73 mmol) and NaOH (0.155 g, 3.87 mmol) were mixed; the resulting precipitate of Cu(OH)2 was filtered off, washed with acetone, and added to a Hdmha (1.00 g, 7.03 mmol) solution in isopropanol (20 ml). After evaporation of alcohol, the target product was extracted with chloroform and purified by vacuum sublimation (T = 90 °C,P = 210-2 Torr). Yield was 65%. The elemental analysis (wt.%) for CuC14H26N4O2 (2) calculated N 16.2, C 48.5, H 7.5,found N 16.0, C 48.4, H 7.6. IR spectrum (ν, cm-1): 3430, 2980, 2945, 2860, 2780, 1575, 1500, 1460, 1400, 750.
	With sodium dodecyl-sulfate In water

Yield	Reaction Conditions	Operation in experiment
	With urea In water generation of basic nitrate by heating Cu(NO3)2 with urea, pptn. of Cu(OH)2 with NaOH-soln.;;
	In water washed, dried at 373 K;
	In water

	In water mixed in aq. soln.;
	In H₂O NaOH added dropwise to aq. soln. of Cu(NO3)2 under magnetic stirring at room temp.;
	In water
	With urea In water generation of basic nitrate by heating Cu(NO3)2 with urea, pptn. of Cu(OH)2 with NaOH-soln.;;
	With NH₃H₂O In water to H2O-soln. of Cu(NO3)2 NH3H2O soln. added with stirring, NaOH-soln. added dropwise, pH=9-10; ppt. filtered, washed, dried at room temp.;
	With water for 4h;	Synthesis of CuO NPs CuO NPs were synthesized by precipitation method. Copper nitrate was used as a precursor and sodium hydroxide as hydrolyzing agent. In brief, the requisite amount of caffeine was dissolved in 0.1M of the copper nitrate solution, which taken in a 250 ml conical flask and heated on magnetic stirrerat 80 deg.C for half an hour. Then, the sodium hydroxide solution was slowly added to the above reaction mixtureand continuously stirred for 4 h. The precipitate formed wasthoroughly washed with distilled water to remove untreated reactants and organic matter. The precipitate was dried in an oven at 100 deg.C for 3 h. The copper hydroxide was annealed at 500 deg.C in a muffle furnace for 3 h to obtain the copper oxide. The samples prepared using 50, 100, and200 mg of caffeine with the same procedure were named asCF1, CF2, and CF3. A blank one prepared without caffeine was named as CF0.
	In water	As illustrated in Fig. 1, Cu(OH)2 was first prepared using a simpleprecipitation method. Typically, 1.208 of g Cu(NO3)2 and 0.2 g ofNaOH were dissolved in 100 mL and 20 mL of deionized water,respectively. Next, the aqueous solution of NaOH was slowlypoured into the aqueous solution of Cu(NO3)2 under constant stirring.Cu(OH)2 was then obtained via filtration and dried at 60 C for8 h under vacuum.

[ CAS No. 20427-59-2 ] {[proInfo.proName]}

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[ 20427-59-2 ] Synthesis Path-Upstream 1~2

[ 20427-59-2 ] Synthesis Path-Downstream 1~88

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Yield	Reaction Conditions	Operation in experiment
	In water
	In water mixing NaOH and metal acetate soln. in various ratios (total soln. concn. ca. 0.25 or 0.125 M, NaOH>=66.7 mol-% in the mixt.), pptn., mother liquor sepn. (filtration) from. ppt. after equilibration; chem. and phys.-chem. anal. of mother liquor;
	In water

	In water at 20℃;	2 Experimental method 0.1M Cu(OH)2 solution was also prepared by mixing 0.1M Cu(CH3COO)2 and adjusting the solution to pH=6.5 by adding 1M NaOH in the solution at room temperature.
	at 60℃;

Yield	Reaction Conditions	Operation in experiment
	In water NaOH added to CuSO4*5H2O, pH > 10; ppt. rapidly centrifuged off, washed with water to pH 7;
	In water pptd.;
	In H₂O byproducts: Na2SO4; CuSO4*5H2O (0.125 mmol) soln. added slowly to soln. of NaOH (0.25 mmol); ppt. washed with H2O, dried in vac. at 50°C;

	In not given
	With NH₄OH In water Cu-compd. was dissolved in a 0.05-15 M aq. NH4OH soln., stirring for 15 min, 1.2 M NaOH was added dropwise, stirring for 15 min; ppt. was several washed with distd. H2O, filtered, dried in an oven at 35 °C for 24 h;
	In water reacting cold aq. Cu salt with cold aq. NaOH;
	In water	2.2. Synthesis of [Cu₂(phen)₄(GeW₁₂O₄₀)] (1) CuSO4·5H2O (0.245 g, 1.00 mM) was dissolved in water and then 1M NaOH solution was added. Cu(OH)2 was obtained by filtration, which was then washed with distilled water five times. The freshly prepared Cu(OH)2, phen·H2O (0.200 g, 1.00 mM) H4GeW12O40·nH2O (3.110 g, 1.00 mM), and CH3OH/H2O (v/v = 1 : 2, 15 mL) were mixed and stirred for 2 h. The resulting blue suspension was heated in a 23 mL Teflon-lined stainless steel autoclave at 433 K for 100 h. After the autoclave was cooled to room temperature over 12 h, blue block single crystals of 1 were obtained and then washed with distilled water and finally dried in air (yield: 33.98% based on the initial phen·H2O input).
	In water Sonication;	Typically, 56 mL NaOH solution (1.5 mol L-1) was added dropwise into 28 mL CuSO4 solution (0.5 mol L-1) under ultrasonication and magnetic stirring. The resulting solution turned light blue immediately, indicating the formation of Cu(OH)2 precipitate.
	In water
	Stage #1: copper(ll) sulfate pentahydrate With sodium citrate In water at 30℃; Stage #2: sodium hydroxide In water	2.2. Preparation of Copper Nanoparticles Copper sulfate and organic modifier were dissolved indeionized water in a 500 mL volumetric flask, denoted assolution A. Sodium hydroxide and organic modifier weredissolved in deionized water in a 500 mL volumetric flask,denoted as solution B. Hydrazine hydrate was diluted indeionized water in a 500 mL volumetric flask, denoted assolution C. The concentrations of copper sulfate, sodiumhydroxide, and organic modifiers are listed in Table I. Thetotal dose of organic modifier was evenly divided into twoparts and added in solutions A and B, respectively. Thepreparation procedures of copper nanoparticles are illustrated as follows.Solution A was added into a 2 L three-necked, roundbottomflask under stirring and heated to a given temperature.Solution B was added into solution A dropwise witha constant flow pump at a flow rate of 8 mL min-1. Copperhydroxide suspension was obtained. And then, solution Cwas added into the resultant copper hydroxide suspensiondropwise at a flow rate of 6 mL min-1. The reaction mixturewas keep at the given temperature and stirred for2 h. The Cu2+ cations were completely reduced to metallicCu0. The resultant copper nanoparticles were separatedfrom the solution by centrifugation at 8000-10000 rpmand washed with ethanol for 5 times. The organic modifiers,such as SCP, PVP, and SDBS, were completelyremoved from the metallic Cu nanoparticles by washingwith anhydrous ethanol. The asprepared copper nanoparticle samples were stored in methanol before using. Afterdrying at 40 C in a vacuum oven for 12 h, the dried coppernanoparticles were used for tribological performancemeasurement.
	In water Cooling;	2.1.2. Synthesis of leaf-shaped CuO About 4.7 g CuSO4.5H2O was dissolved in 35 ml of deionized watervery slowly to get a greenish-blue solution. Then around 1.7 g of NaOH was dissolved gradually in 5.5 ml deionized water with constant stirringto keep the temperature low. To the above CuSO4 clear solution, NaOHsolution was added very slowly with constant stirring. A bluish-blackprecipitate appears suddenly. The reaction flask was heated for 45 minto 1 h while maintaining the temperature at 80C and stirring the reactionmixture intermediately. The brownish-black thick precipitate ofcopper oxide thus obtained was washed with a sufficient amount ofdeionized water and filtered free of alkali. It was then dried to removeany trace of water. The precipitate was ground using mortar and pestleand used for further synthesis.

Yield	Reaction Conditions	Operation in experiment
87%	With ammonia In water ammonia added dropwise to soln. of CuSO4 at 60 °C, soln. of NaOH added dropwise; filtration, washing (water), drying;
	In ammonia 70°C;
	In water addn. of aq. NaOH to CuSO4-soln: first pptn. of basic Cu-sulfate, formation of Cu(OH)2 with excess NaOH (about 0.5 mol); addn. of CuSO4-soln. to aq. NaOH: first pptn. of Cu(OH)2;;

	In water at 35°C;;
	In water
	In ammonia addn. of aq. NH3 to a CuSO4-soln. until pptd. dissolves, addn. of aq. NaOH at 0°C, microcryst. pptn.;;
	In ammonia addn. of aq. NH3 to a CuSO4-soln. until pptd. dissolves, slow addn. of aq. NaOH at 0°C, washing with H2O, alcohol, ether, drying in vac., microcryst. pptn.;;
	In ammonia addn. of concd. NaOH-soln. to CuSO4 in aq. NH3 (small excess of NH3);;
	In ammonia; water formation of basic CuSO4 by slow addn. of 6n NH3 soln. to boiling 1n CuSO3-soln., washing with H2O, triuration with 5% NH3-soln., washing free from SO4(2-), drying on clay in the air;;
	In sodium hydroxide addn. of 0.2 M CuSO4 to 0.1018 M NaOH;;
	In sodium hydroxide aq. NaOH; addn. of 0.2 M CuSO4 to 0.1018 M NaOH;;
	In water at 35°C;;
	In water
	In ammonia aq. ammonia=NH3; addn. of concd. NaOH-soln. to CuSO4 in aq. NH3 (small excess of NH3);;
	In ammonia aq. ammonia=NH3; addn. of aq. NH3 to a CuSO4-soln. until pptd. dissolves, slow addn. of aq. NaOH at 0°C, washing with H2O, alcohol, ether, drying in vac., microcryst. pptn.;;
	In not given metathesis reactio of copped sulfate with NaOH;
	In water
	Stage #1: copper(II) sulfate With sodium citrate In water for 0.0833333h; Stage #2: sodium hydroxide In water for 0.0833333h;
	Stage #1: copper(II) sulfate With polyvinylpyrrolidone In water for 0.5h; Sonication; High pressure; Stage #2: sodium hydroxide In water at 20℃; for 0.5h; High pressure;	Cu2O nanoparticles were synthesized by the hydrothermal method referred to our previouswork [18]. Specifically, 50 mg of CuSO4.5H2O and 24 mg of PVP were added into 10 mL deionizedwater and then stirred with ultrasonication for 30 min. Afterwards, 2 mL of 0.2 mol/L NaOHsolution was added and stirred for 30 min at room temperature to obtain blue Cu(OH)2 precipitates.Subsequently, 6 μL of N2H4.H2O was added as reductant and then stirred for 20 min at roomtemperature to form a brick red suspension. The precipitate was separated by centrifugation at5000 rpm, and washed repeatedly with deionized water and ethanol for three times, and vacuum-driedat 60 °C to obtain Cu2O nanoparticles.

Yield	Reaction Conditions	Operation in experiment
	In ammonia with theoretical amounts of OH(1-);;
	In water an excess of 6N NaOH was added to a soln. of CuCl2; ppt. was washed with water to get it free from chloride ions;
	In water

	In water
	In ammonia aq. ammonia=NH3; with theoretical amounts of OH(1-);;
	In water pptn. on mixing aq. solns. of components, molar ratio NaOH:CuCl2>=2.0; 20+/-0.05°C; washing (water); chem. anal.;
	In sodium hydroxide aq. NaOH; copper hydroxide ppt. prepd. from soln. of NaOH and soln. of CuCl2;
	In further solvent(s) reacted in the presence of small amount of polyethylene glycol ather at 0°C;
	With HCl In water soln. of NaOH was dropped into soln. of CuCl2 under agitation at room temp.; when pH value of soln. reached 12.5, the pH value was maintained for 30 min by dropping soln. of NaOH or HCl; after 1.5 h agitation was stopped; ppt. aged for 1-3 ds; ppt. washed (H2O, abs. EtOH) several times;
	In water
	With sodium dodecyl-sulfate In water at 30 - 32℃; for 0.00277778h;
	In water	Synthesis of nanodomain cubic Cu₂O: To the aqueous solution of CuCl2 (0.01 M, 100 mL), NaOH (0.2 M, 10 mL) was added drop wise under stirring. The color of the solution was found to change from green to blue due to the formation of Cu(OH)2. Fructose (1 M,10 mL) in water was then added drop wise to it and stirring was continued at 60-65 °C for 1 h. The precipitates slowly changed from green to yellow which indicated formation of Cu2O nanoparticles. The solution was then allowed to settle down for 1 h for complete nucleation. It was then centrifuged, and the precipitate was washed with water and then ethanol for three to four times and dried under vacuum before use.
	In water
	In water at 20℃;	Preparation and characterization of CuONPs CuONPs were synthesized by precipitation technique, utilizing copper chloride and sodium hydroxide as precursors; both were dissolved separately in deionized water. Sodium hydroxide solution was added dropwise into copper chloride solution with continuous magnetic stirring at room temperature resulting in a bluish gel of Cu(OH)2. The precipitates obtained were filtered and washed with deionized water that upon drying and annealing yielded CuONPs (Manimaran et al.2014).

Yield	Reaction Conditions	Operation in experiment
	In ammonia with theoretical amounts of OH(1-);;
	In water reaction in 2:1 KOH:CuCl2 molar ratio;
	In ammonia with theoretical amounts of OH(1-); washing with ice-water, alcohol and ether, drying in vac.;;

	In ammonia aq. ammonia=NH3; with theoretical amounts of OH(1-);;
	In water	Cu(II) complexes. General procedure: [Cu(acacen)] and [Cu(hfac)2] were synthesized according to the method described in the literature [28] by interaction of H2acacen (1.00g, 4.5mmol) or Hhfac (1.28ml, 9.0mmol) with as-precipitated Cu(OH)2 (0.50g, 5.1mmol, 13% excess) in the presence of acetone (15mL). Cu(OH)2 was obtained by mixing aqueous solutions of CuCl2(0.68g, 5.1mmol) and KOH(0.58g, 10.3mmol). After acetone evaporation, Cu (II) complexes were extracted with chloroform and purified by double vacuum sublimation.

	In solid nanoribbons, nanowires or nanoplatelets prepd. from Cu(OH)2 nanostructures by heating at 120°C for 2 h and subsequently at 180°C for 3 h;
	In water aging on synthesis by pptn.;; Cu(OH)2 isolable only at low temperatures and under special conditions;;
	In water byproducts: H2O; High Pressure; on heating to 190°C in an autoclave for 1h;;
	In water byproducts: H2O; aging in boiling H2O;;
	In water byproducts: H2O; dehydratisation-rate of electrolytically synthesized Cu(OH)2 (on standing in electrolyte-soln.) depending on current density, period of electrolysis, concn. of electrolyte, temp.;;
	In water byproducts: H2O; increased decompn.-rate in presence of H2O2-traces;;
	In water nanoribbons, nanowires or nanoplatelets prepd. directly from alkaline soln. of Cu(OH)2 nanostructures by heating (e.g., 30 and 50°C) for 12 h; alternatively sepd. Cu(OH)2 redispersed in deionized H2O and heated at 70°C for 1-12 h;
	In neat (no solvent) Cu(OH)2 gel aged at 80°C for 2 days; thoroughly washed with doubly distilled water, freeze dried;
	In neat (no solvent) byproducts: H2O; aging process depending on snthesis method;;
	In neat (no solvent) byproducts: H2O; aging-rate depending on crystal form;;
	In neat (no solvent) byproducts: H2O; aging-rate depending on starting material for hydroxide synthesis, increase of rate from Cu-acetate to CuSO4;;
	In neat (no solvent) byproducts: H2O; aging-rate depending on starting material for hydroxide synthesis, increase of rate from CuBr2 to CuCl2 to Cu(NO3)2;;
	In neat (no solvent) byproducts: H2O; aging-rate depending on starting material for hydroxide synthesis, increase of rate from K-Cu-sulfate to CuSO4 to basic Cu-nitrate;;
	In neat (no solvent) byproducts: H2O; at 150°C, mixture of CuO, Cu(OH)2 and H2O;;
	In neat (no solvent) byproducts: H2O; complete dehydration on heating to 450°C for a longer period of time in a stream of dry air;;
	In neat (no solvent) byproducts: H2O; dehydratisation-rate increases with increasing temp.;;
	In neat (no solvent) byproducts: H2O; heating slowly to 110°C, mixtures of CuO and Cu(OH)2;;
	In neat (no solvent) byproducts: H2O; heating to 125°C in a stream of dry air;; contents up to 1% H2O;;
	In neat (no solvent) byproducts: H2O; heating to 220°C for 4h in a N2-stream;;
	In neat (no solvent) byproducts: H2O; mechanochemical decompn. by dry grinding (3h) or by wet grinding (in cyclohexane);; detn. by X-ray, IR, DTA, ESR;
	In neat (no solvent) byproducts: H2O; on heating to 100°C;;
	In neat (no solvent) byproducts: H2O; on heating;;
	In neat (no solvent) byproducts: H2O; slow aging in presence of a small excess of NaOH at low temperatures;;
	In neat (no solvent) byproducts: H2O; stabilization in presence of NH4Cl or (NH4)2SO4, no influence of NH4NO3 and KCl;;
	In neat (no solvent) byproducts: H2O; stabilization in presence of chlorides or sulfates of Mn, Ni, Co, Cr, Fe, Cd, Mg, Ca, Sr, Al, Zn or Pb;;
	In neat (no solvent) byproducts: H2O;
	In neat (no solvent) sample decompn. at 260°C; XRD;
	In neat (no solvent) stabilizing effects investigated;;
	In neat (no solvent) thermal dehydroxylation of Cu(OH)2 at 200°C;;
	In neat (no solvent) byproducts: H2O; heated under N2; DTA;
	In potassium hydroxide byproducts: H2O; aging;;
	In potassium hydroxide byproducts: H2O; on standing for a longer period of time in the alcaline mother-liquor, rate depending on concn. of KOH;;
	In sodium hydroxide at temp. higher than 18°C, in contact with mother-liquor and in absence of a stabilizator;; mixture of Cu(OH)2 and CuO;;
	In sodium hydroxide byproducts: H2O; aging under influence of current, suspension of Cu(OH)2 in NaOH-soln.;;
	In sodium hydroxide byproducts: H2O; aging;;
	In sodium hydroxide byproducts: H2O; in moderate concd. NaOH-soln.;;
	In sodium hydroxide byproducts: H2O; on standing for a longer period of time in the alcaline mother-liquor at temperatures higher than 20°C;;
	In sodium hydroxide byproducts: H2O; on standing for a longer period of time in the alcaline mother-liquor, rate depending on concn. of NaOH;;
	In sodium hydroxide electrochemical react:;;
	In sodium hydroxide stabilisation in presence of sugar;;

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide
	With NH₃*H₂O; NaOH; hexadecyl trimethyl ammonium bromide In water; cyclohexene; butan-1-ol ammonia added to aq. soln. of CuSO4; hexadecyl trimethyl ammonium bromide, n-butanol added to cyclohexane; aq. soln. of Cu(NH3)4(2+) added; stirred; NaOH added by dropping; stirred for 30 min and resy at room temp. for 8 h; dried at 60°C for 3 h; SEM; TEM; XRD: TGA;
	Stage #1: copper(ll) sulfate pentahydrate With D-glucose In water Inert atmosphere; Stage #2: With sodium hydroxide In water for 0.5h;

	With sodium hydroxide In water at 25℃; for 0.5h;	The preparation of Cu2O nanoparticles was illustrated as follows. NaOH aqueous solution (250 mL) with the concentrations of 0.1-0.4 mol/L was added into 250 mL of CuSO4 aqueous solution with the concentrations of 0.05-0.2 mol/L under stirring with a constant flow ratepump at 25°C for 30 min to form Cu(OH)2 suspension.Then 250 mL of ascorbic acid aqueous solution with the concentrations of 0.1-0.4 mol/L was added into the resultant suspension with a constant flow rate pump understirring at 25°C for 30 min to prepare Cu2O nanoparticles.To change particle sizes of Cu2O nanoparticles, given amount of polyvinyl pyrrolidone was first dissolved inCuSO4 aqueous solution. Then NaOH and ascorbic acid solutions were added subsequently. The as prepared Cu2O nanoparticles were washed with water and ethanol for three times, and then kept in an ethanol solution. After drying in an vacuum oven at 60°C for 60 min, the asprepared Cu2O nanoparticles were used as the catalysts for the hydrothermal conversion of glycerol
	With sodium hydroxide In water
	With ammonium hydroxide; sodium hydroxide In water

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In water 1% H2O2-soln.;;
	In solid Cu(OH)2 nanoneedle sample heated to 150°C for 3 h, then at 200°c for 3 h under N2, naturally cooled to room temp.; CuO nanoneedles obtained;
	In solid calcined at 450-500°C for 4 h;

Yield	Reaction Conditions	Operation in experiment
	With D-glucose
	With carbon monoxide In ammonia aq. suspension of Cu(OH)2 containing NH3 (even small amounts are sufficient);;
	With chromium(III) oxide In sodium hydroxide heating Cu(OH)2 in an alkaline soln. of Cr2O3 to 100°C;;

>99	With copper In sodium hydroxide reduction on shaking the mixture with NaOH-soln. in a closed vessel for several days;;
	With hydrazine In water reduction;;
	With NH₂NHOH In water N2-atmosphere, 20°C, pH=10.2;;
	With sodium sulfite
	With cane-sugar In potassium hydroxide pouring concd. aq. sugar-soln. on pressed moist Cu(OH)2, addn. of aq. KOH, filtration after shaking, heating on a water-bath, pptn.;; filtration, washing, drying;;
	With D-glucose In water reduction in neutral soln.;;
	With hydrazine In ammonia addn. of hydrazine-soln. (H2- or N2-atmoshere);; contains about 3.5% H2O;;
	With hyroxylammonium sulfate or hydroxylammonium chlori; de In water H2O-contenting mixture of Cu(OH)2 and Cu2O, less violent react. in presence of OH(1-);;
	With laevulose or dextrose or invert-sugar or cane-; sugar; In water reduction; increase of react.-rate in presence of Ba(OH)2;;
	With phenylhyrazine In potassium hydroxide; ammonia pptn. from the NH3-soln. on addn. of hot 10% KOH-soln. and phenylhydrazine;;
	With Sucrose 92°C;
	With Sucrose In potassium hydroxide heating with KOH-containing sugar-soln., pptn.;;
	With D-(+)-glucose In water Cu(OH)2 was decomposed at 60°C, reducted with D-(+)-glucose; X-ray diffraction;
	In sulfuric acid aq. H2SO4; pptn. from a satd. soln. of Cu(OH)2 in NaOH on standing;;
	With hydrazine In ammonia aq. ammonia=NH3; addn. of hydrazine-soln. (H2- or N2-atmoshere);; contains about 3.5% H2O;;
	With CO In ammonia aq. ammonia=NH3; aq. suspension of Cu(OH)2 containing NH3 (even small amounts are sufficient);;
>99	With Cu In sodium hydroxide aq. NaOH; shaking in NaOH-soln. for several days;;
	With N₂H₄ In water reduction;;
	With NH₂NHOH In water N2-atmosphere, 20°C, pH=10.2;;
	With hyroxylammonium sulfate or hydroxylammonium chlori; de In water H2O-contenting mixture of Cu(OH)2 and Cu2O, less violent react. in presence of OH(1-);;
	In sulfuric acid aq. H2SO4; pptn. from a satd. soln. of Cu(OH)2 in NaOH on standing;;
	With hydrazine hydrate In water at 80 - 140℃; Autoclave;	After stirring for 30min, 2mL of a 14M solution of hydrazine (N2H4·H2O) was added dropwise to the solution with the blue Cu(OH)2 precipitate under constant stirring for 30min to reduce Cu2+ to Cu1+. The Cu(OH)2 precipitate gradually turned red. After the Cu(OH)2 precipitate was completely reduced by the N2H4, the red gel was transferred into an autoclave and was heated for 10h at different temperatures (80, 100, 120 and 140°C). The produced precipitates were filtered, were washed with distilled water several times, and were dried in a vacuum oven at 60°C for 3h.
	With ascorbic acid for 0.166667h;

Yield	Reaction Conditions	Operation in experiment
	at 100℃; for 10h;
	at 500℃; for 1h; Calcination;
	With air at 400℃; for 2h;

	at 130℃; for 8h; Autoclave; High pressure;
	Stage #1: copper hydroxide at 150℃; for 0.5h; Stage #2: for 0.5h; Sonication;
	With N-butylamine at 100℃; for 2h; Autoclave;
	In water at 130℃; for 10h; Autoclave;
	With air at 300℃; for 1h;
	In neat (no solvent, solid phase) Heating;	Preparation and characterization of CuONPs CuONPs were synthesized by precipitation technique, utilizing copper chloride and sodium hydroxide as precursors; both were dissolved separately in deionized water. Sodium hydroxide solution was added dropwise into copper chloride solution with continuous magnetic stirring at room temperature resulting in a bluish gel of Cu(OH)2. The precipitates obtained were filtered and washed with deionized water that upon drying and annealing yielded CuONPs (Manimaran et al.2014).
	at 500℃; for 3h;	Synthesis of CuO NPs CuO NPs were synthesized by precipitation method. Copper nitrate was used as a precursor and sodium hydroxide as hydrolyzing agent. In brief, the requisite amount of caffeine was dissolved in 0.1M of the copper nitrate solution, which taken in a 250 ml conical flask and heated on magnetic stirrerat 80 deg.C for half an hour. Then, the sodium hydroxide solution was slowly added to the above reaction mixtureand continuously stirred for 4 h. The precipitate formed wasthoroughly washed with distilled water to remove untreated reactants and organic matter. The precipitate was dried in an oven at 100 deg.C for 3 h. The copper hydroxide was annealed at 500 deg.C in a muffle furnace for 3 h to obtain the copper oxide. The samples prepared using 50, 100, and200 mg of caffeine with the same procedure were named asCF1, CF2, and CF3. A blank one prepared without caffeine was named as CF0.
	at 250℃; for 1h; Calcination;	2.3. Synthesis of copper oxide nanostructures Leaf extract (30 mL) was taken in a separate beaker, in which Cu(NO3)23H2O (1 g) was added under stirring at 80 C. The stirring wascontinued until the solution was turned from dark green to green colorpaste indicating formation of copper hydroxide (Cu(OH)2), which waswashed two or three times by distilled water. The Cu(OH)2 precipitatewas transferred into a silica crucible and calcinated at 250 C for 1 h in amuffle furnace, the resultant dark color powder indicates the formationof CuO nanostructures.
	With urea In neat (no solvent, solid phase) at 750℃;
	In neat (no solvent, solid phase) at 500℃; for 4h;

Yield	Reaction Conditions	Operation in experiment
	With hydroxyamino hydrochloride for 1h;
	With D-Fructose In lithium hydroxide monohydrate at 60 - 65℃; for 1h;	Synthesis of nanodomain cubic Cu₂O: To the aqueous solution of CuCl2 (0.01 M, 100 mL), NaOH (0.2 M, 10 mL) was added drop wise under stirring. The color of the solution was found to change from green to blue due to the formation of Cu(OH)2. Fructose (1 M,10 mL) in water was then added drop wise to it and stirring was continued at 60-65 °C for 1 h. The precipitates slowly changed from green to yellow which indicated formation of Cu2O nanoparticles. The solution was then allowed to settle down for 1 h for complete nucleation. It was then centrifuged, and the precipitate was washed with water and then ethanol for three to four times and dried under vacuum before use.
	With L-ascorbic acid In lithium hydroxide monohydrate for 1h; Sonication;	50 mL of freshly prepared ascorbic acid solution (0.1 mol L1) was immediately added dropwise to the above suspension Cu(OH)2. The resulting mixture was then ultrasonicated and stirred for another 1 h. Finally, the red precipitate was collected by filtration, washed repeatedly with deionized water untilthe pH of the aqueous effluent was neutral, and dried at 60 C in an oven.

	With D-glucose In lithium hydroxide monohydrate at 80℃; for 1h;
	With L-ascorbic acid In lithium hydroxide monohydrate at 20℃; for 0.166667h;
	With hydrazine hydrate monohydrate In lithium hydroxide monohydrate
	With hexose In lithium hydroxide monohydrate at 60℃; for 1h;	Synthesis of cubic Cu₂O nanoparticles Nanodomain Cu2O was synthesized as follows. To the aqueous solution of CuCl2 (0.01 M, 100 mL), NaOH (0.2 M, prepared in water, 10 mL) was added dropwise under slow stirring. The colour of the solution was noticed to be changed gradually from green to blue due to the formation of Cu(OH)2. Glucose (1 M, 10 mL) in water was then added slowly into it and stirring was allowed to continue at 60 °C for 1 h more. The color of the precipitates gradually changed from green to yellow which indicates the formation of Cu2O nanoparticles. The solution was then allowed to settle for 1 h. These allow complete nucleation of the particles. It was then centrifuged, followed by repeated washing with water and ethanol. The particles were dried under vacuum before use.
	With sodium hydroxide In lithium hydroxide monohydrate for 0.5h;
	With hydroxyamino hydrochloride for 1h; Sonication;
	With hydrazine hydrate monohydrate at 20℃; for 0.333333h;	3.2. Synthesis of Cu2O Nanoparticles Cu2O nanoparticles were synthesized by the hydrothermal method referred to our previouswork [18]. Specifically, 50 mg of CuSO4.5H2O and 24 mg of PVP were added into 10 mL deionizedwater and then stirred with ultrasonication for 30 min. Afterwards, 2 mL of 0.2 mol/L NaOHsolution was added and stirred for 30 min at room temperature to obtain blue Cu(OH)2 precipitates.Subsequently, 6 μL of N2H4.H2O was added as reductant and then stirred for 20 min at roomtemperature to form a brick red suspension. The precipitate was separated by centrifugation at5000 rpm, and washed repeatedly with deionized water and ethanol for three times, and vacuum-driedat 60 °C to obtain Cu2O nanoparticles.
	With ethylene glycol at 220℃; for 2h; Inert atmosphere;
	With L-ascorbic acid In lithium hydroxide monohydrate for 1.25h;	The synthesis of Cu2O NPs Ascorbic acid of 15.6 g was added to 40 mL of distilledwater and stirred for 30 min. The solution was addeddrop by drop to the previous solutions, and a change incolor from green to orange indicated the formation ofCu2O particles.The solution was stirred for 45 min, then the fi lterwas washed twice with distilled water, and the preparedprecipitate was placed in a vacuum oven at 150°C for 4 h.
	With H₃NO*3ClH for 1h; Sonication;
	With hydroxyamino hydrochloride for 1h; Sonication;

Yield	Reaction Conditions	Operation in experiment
	With ethylenediamine; sodium hydroxide; hydrazine In water at 70℃; for 1h; Green chemistry;
	Stage #1: copper hydroxide With hydrazine hydrate In water at 60℃; for 0.5h; Inert atmosphere; Stage #2: In water for 5h; Sonication; Inert atmosphere;	Ultrasonication of Copper Compounds General procedure: 1 g of any copper precursor was used in all experiments. Typically, an aqueous solution or suspension of copper precursorwas contained in a 500 mL round-bottom flask (Figure 1)and purged with argon for 30 minutes before starting ultrasonic treatment. The solution was then subjected to a highintensity ultrasound irradiation under argon from animmersed ultrasonic horn (20 kHz, 48 W) for 5 h. To avoidoverheating of the solution by the ultrasound, a pulsed irradiation was used (on for 7 s, off for 3 s). The reaction flask wascooled with a water-ice mixture in case of low-temperatureexperiments (15-20C) and with a regulated air flow in caseof high-temperature experiments (60-70C). Upon completion of the sonication process, the resulting powders were separated from the solution by centrifugation, washed repeatedlywith distilled water, and then dried under vacuum. All ultrasonic reactions were carried out without any surfactants andstabilizing agents, in order not to affect reaction course. pHin solutions/suspensions was not changed before or duringthe processes for the same reason in order not to introducenew cations or anions into reaction systems. As it will beshown subsequently, even a small quantity of organic matter,being present in aqueous solution, inhibits formation of copper-containing nanoparticles in the conditions of ultrasonictreatment
	With hydrazine hydrate In water at 30℃; for 2h;	2.2. Preparation of Copper Nanoparticles Copper sulfate and organic modifier were dissolved indeionized water in a 500 mL volumetric flask, denoted assolution A. Sodium hydroxide and organic modifier weredissolved in deionized water in a 500 mL volumetric flask,denoted as solution B. Hydrazine hydrate was diluted indeionized water in a 500 mL volumetric flask, denoted assolution C. The concentrations of copper sulfate, sodiumhydroxide, and organic modifiers are listed in Table I. Thetotal dose of organic modifier was evenly divided into twoparts and added in solutions A and B, respectively. Thepreparation procedures of copper nanoparticles are illustrated as follows.Solution A was added into a 2 L three-necked, roundbottomflask under stirring and heated to a given temperature.Solution B was added into solution A dropwise witha constant flow pump at a flow rate of 8 mL min-1. Copperhydroxide suspension was obtained. And then, solution Cwas added into the resultant copper hydroxide suspensiondropwise at a flow rate of 6 mL min-1. The reaction mixturewas keep at the given temperature and stirred for2 h. The Cu2+ cations were completely reduced to metallicCu0. The resultant copper nanoparticles were separatedfrom the solution by centrifugation at 8000-10000 rpmand washed with ethanol for 5 times. The organic modifiers,such as SCP, PVP, and SDBS, were completelyremoved from the metallic Cu nanoparticles by washingwith anhydrous ethanol. The asprepared copper nanoparticle samples were stored in methanol before using. Afterdrying at 40 C in a vacuum oven for 12 h, the dried coppernanoparticles were used for tribological performancemeasurement.

Yield	Reaction Conditions	Operation in experiment
	In neat (no solvent, solid phase) at 300℃; for 2h; Calcination; Inert atmosphere;	Next, 0.3 g of Cu(OH)2 and 1.5 g of NaH2PO2 wereground in an agate mortar and transferred into a porcelain boat. The mixture was then calcined at 300 C for 2 h at a rate of 2 Cmin1 in a N2 atmosphere. After cooling, the black Cu3P waswashed several times with deionized water and ethanol, and then dried at 80 C for 12 h.
	at 300℃; for 1h; Calcination; Inert atmosphere;

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