104-38-1

Basic information

• Product Name: Hydroquinone bis(2-hydroxyethyl)ether
• Synonyms: Vernatzer 30/10;Hydroquinone bis(2-hydroxyethyl)ether 99+%;2,2'-(p-Phenylenebisoxy)diethanol;Hydroquinone di(2-hydroxyeth;1,4-Di(2-hydroxyethoxy)benzene Hydroquinone Bis(2-hydroxyethyl) Ether Hydroquinone Di(2-hydroxyethyl) Ether;2,2'-(1,4-Phenylenebis(oxy))diethanol;Hydroquinone bis(2-hydroxyethyl) ether 98%;chain extender
• CAS NO: 104-38-1
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• EINECS: 203-197-3
• Product Categories: Benzene derivates
• Mol File: 104-38-1.mol

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 185-200 °C (0.3 mmHg)
• Flash Point: 183.618 °C
• Appearance: White to off-white/Crystalline Powder or Flakes
• Density: 1.0143 (rough estimate)
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Refractive Index: 1.4720 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.99±0.10(Predicted)
• Water Solubility: practically insoluble
• Sensitive: Hygroscopic
• CAS DataBase Reference: Hydroquinone bis(2-hydroxyethyl)ether(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroquinone bis(2-hydroxyethyl)ether(104-38-1)
• EPA Substance Registry System: Hydroquinone bis(2-hydroxyethyl)ether(104-38-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 104-38-1(Hazardous Substances Data)

Usage

Uses

1. Used in Plastics and Polymer Industry:
Hydroquinone bis(2-hydroxyethyl)ether is used as a monomer for the production of polyester, polyolefins, polyurethanes, and hard waxy resins. Its application in this industry is due to its ability to form strong and durable polymers with excellent mechanical and thermal properties.
2. Used in Organic Synthesis:
Hydroquinone bis(2-hydroxyethyl)ether is used as an intermediate in organic synthesis, particularly for the production of 1,4-bis-(2-bromo-ethoxy)-benzene. Its use in this application is attributed to its reactive functional groups, which allow for further chemical modifications and the creation of a wide range of compounds with diverse properties and applications.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 163, 1988 DOI: 10.1016/S0040-4039(00)80042-8

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H14O4/c11-5-7-13-9-1-2-10(4-3-9)14-8-6-12/h1-4,11-12H,5-8H2

Synthetic route

oxirane (75-21-8) + hydroquinone (123-31-9) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
Stage #1: hydroquinone With 1,1'-bis-(diphenylphosphino)ferrocene In diethylene glycol dimethyl ether at 100℃; Autoclave; Inert atmosphere; Stage #2: oxirane In diethylene glycol dimethyl ether at 130 - 135℃; for 4h; Solvent; Temperature;	99.3%
anion exchange resin A (Cl-type) In 2-methoxy-ethanol; toluene at 100℃; for 6h;	73%
anion exchange resin A (Cl-type) In 2-methoxy-ethanol at 100℃; for 4.5h;	69 %Chromat.

ethylene glycol (107-21-1) + hydroquinone (123-31-9) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With urea; sodium carbonate; zinc(II) oxide at 180℃; for 3h; Product distribution / selectivity;	98%
With sodium carbonate; urea; zinc(II) oxide at 170 - 190℃;	85%

[1,3]-dioxolan-2-one (96-49-1) + hydroquinone (123-31-9) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 140℃;	89%
With 1,4-dioxane; N-benzyl-trimethylammonium hydroxide
With sodium hydride In N,N-dimethyl-formamide

hydroquinone (123-31-9) + 2-chloro-ethanol (107-07-3) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
Stage #1: hydroquinone With sodium hydroxide In water for 2h; Inert atmosphere; Reflux; Stage #2: 2-chloro-ethanol In water for 40h; Reflux; Inert atmosphere;	74%
With sodium hydroxide In water for 24h; Heating;	60%
With sodium hydroxide Inert atmosphere;

sodium 4-hydroxybenzen-1-olate (30008-10-7) + 2-chloro-ethanol (107-07-3) → 4-(2-hydroxyethoxy)-phenol (13427-53-7) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With ethanol

C20H30O6 → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane for 4h; Ambient temperature;

hydroquinone (123-31-9) + <(η6-1,2-dichlorobenzene)(η5-cyclopentadienyl)>iron(II) hexafluorophosphate → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH, sodium dithionite / butan-1-ol / 30 h / Heating 2: conc. HCl / methanol; CH2Cl2 / 4 h / Ambient temperature View Scheme

1,4-Phenylen-bis-oxyacetaldehyd (24535-81-7) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃;	3.87 g

(4-ethoxycarbonylmethoxy-phenoxy)-acetic acid ethyl ester (5897-78-9) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Reflux; Inert atmosphere;

hydroquinone (123-31-9) → 1,4-bis(2-hydroxyethoxy)benzene (104-38-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux; Inert atmosphere View Scheme

methanesulfonyl chloride (124-63-0) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-(methylsulfonyloxy)ethoxy)benzene (133633-40-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.416667h;	100%
With pyridine In dichloromethane at 0 - 20℃;	94%
With triethylamine In dichloromethane	73%
With triethylamine In dichloromethane for 9h; Reflux;	71.3%
With triethylamine In dichloromethane for 1.5h; Cooling with ice; Inert atmosphere;

cis-5-methyl-2-phenyl-1,3-dioxane-5-carboxylic anhydride (1257583-43-9) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-((cis-5-methyl-r-2-phenyl-1,3-dioxan-5-yl)methanoyloxy)ethoxy)benzene (1257583-47-3)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;	97%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + 2,2,5-trimethyl-1,3-dioxane-5-carboxylic anhydride (408322-03-2) → 1,4-bis(2-((2,2,5-trimethyl-1,3-dioxan-5-yl)methanoyloxy)ethoxy)benzene (1431636-34-8)

Conditions	Yield
With dmap In pyridine; dichloromethane at 20℃; for 4h; Inert atmosphere;	96%

formaldehyd (50-00-0) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + trimethylamine (75-50-3) → ammonium pillar[5]arene

Conditions	Yield
Stage #1: 1,4-bis(2-hydroxyethoxy)benzene With carbon tetrabromide; triphenylphosphine In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: formaldehyd With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #3: trimethylamine In ethanol Reflux;	95%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-bromoethoxy)benzene (5471-84-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In acetonitrile at 20℃; for 4h; Cooling with ice;	94%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 20℃; for 4h; Cooling with ice;	94%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;	93%

3-(benzyloxy)-2,2-bis(benzyloxymethyl)propanoic anhydride (1257583-44-0) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-(2,2',2''-tris(benzyloxymethyl)ethanoyloxy)ethoxy)benzene (1257583-51-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 12h; Inert atmosphere;	94%

3-(benzyloxy)-2,2-bis(methoxymethyl)propanoic anhydride (1613034-66-4) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-(3-benzyloxy-2,2-bis-(methoxymethyl)propanoyloxy)ethoxy)benzene

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 12h; Inert atmosphere;	94%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + p-toluenesulfonyl chloride (98-59-9) → 2,2'-[1,4-phenylenebis(oxy)]bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) (37108-78-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 2h;	90%
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h;	82%
With pyridine; dmap In tetrahydrofuran at 20℃;	72%

C30H36N16O10 (865813-91-8) + acetic anhydride (108-24-7) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → C58H68N16O20

Conditions	Yield
With trifluoroacetic acid at 70℃; for 3.5h;	90%
With trifluoroacetic acid at 70℃; for 3.5h;	90%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-dibromo-2,5-di(2'-hydroxyethoxy)benzene (56466-44-5)

Conditions	Yield
With N-Bromosuccinimide In butanone at 65 - 70℃; Inert atmosphere;	90%

C30H36N16O10 + acetic anhydride (108-24-7) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → C58H68N16O20

Conditions	Yield
With trifluoroacetic acid at 70℃; for 3.5h;	90%

3-(benzyloxy)propanoic acid (27912-85-2) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis((3-benzyloxypropanoyloxy)ethoxy)benzene

Conditions	Yield
Stage #1: 3-(benzyloxy)propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-bis(2-hydroxyethoxy)benzene In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;	89%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-Bis(2-chloroethoxy)benzene (37142-37-3)

Conditions	Yield
With pyridine; thionyl chloride at 20℃;	88%
With pyridine; thionyl chloride In toluene for 24h; Heating;

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 2,2'-(1,4-phenylenedioxo)diethyl diiodide (888721-91-3)

Conditions	Yield
With carbon tetraiodide; triphenylphosphine In acetonitrile at 0 - 20℃; for 3h; Inert atmosphere;	87%
With carbon tetraiodide; triphenylphosphine Inert atmosphere;	83%
Multi-step reaction with 2 steps 1: 94 percent / pyridine / CH2Cl2 / 0 - 20 °C 2: 93 percent / sodium iodide / acetone / Heating View Scheme

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-hydroxyethoxy)-2,5-diiodobenzene

Conditions	Yield
With Iodine monochloride In methanol at 15℃; for 4h; Reflux;	86%
With potassium iodate; iodine Acidic conditions; Reflux;

bis-2,2-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)methyl-3-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)propanoic acid + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis-(2-(2,2,2-tris((cis-5-methyl-r-2-phenyl-1,3-dioxan-5-yl)methanoyloxymethyl)ethanoyloxy)ethoxy)benzene

Conditions

Yield

Stage #1: bis-2,2-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)methyl-3-(5-methyl-2-phenyl-1,3-dioxane-5-carbonyloxy)propanoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 1,4-bis(2-hydroxyethoxy)benzene In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; chemoselective reaction;

82%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + Propiolic acid (471-25-0) → 1,4-bis(2-(2-propynyloxy)ethoxy)benzene

Conditions	Yield
Stage #1: Propiolic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-bis(2-hydroxyethoxy)benzene In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	78%

2,2'-Bis(2,2'-bis-(2-propynyloxymethyl)propanoyloxymethyl)propanoic anhydride + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → C64H78O22

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 12h; Inert atmosphere;	73%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoylchloride (61960-57-4) → benzene-1,4-diylbis(oxyethane-2,1-diyl)bis[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate]

Conditions	Yield
With triethylamine In benzene at 20 - 55℃; for 4h;	72%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-fluoroethoxy)benzene

Conditions	Yield
With pyridine-2-sulfonyl fluoride; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine In toluene at 20℃; for 48h;	72%

4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride (29305-46-2) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → benzene-1,4-diylbis(oxyethane-2,1-diyl)bis[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate]

Conditions	Yield
With triethylamine In benzene at 20 - 55℃; for 4h;	70%

1,4-bis(2-hydroxyethoxy)benzene (104-38-1) + benzoic acid (65-85-0) → 1,4-bis(2-benzoyloxyethoxy)benzene (1309460-14-7)

Conditions	Yield
Stage #1: benzoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1,4-bis(2-hydroxyethoxy)benzene In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; chemoselective reaction;	69%

2,2'-bis-(2-propynyloxymethyl)propanoyl anhydride + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis-2-(2,2'-bis-(((2-propynyloxy)methyl)propanoyloxy)ethoxy)benzene

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 12h; Inert atmosphere;	69%

phenylacetic acid (103-82-2) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 1,4-bis(2-(2-phenylacetyloxy)ethoxy)benzene (1309460-16-9)

Conditions	Yield
Stage #1: phenylacetic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1,4-bis(2-hydroxyethoxy)benzene In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; chemoselective reaction;	67%

formaldehyd (50-00-0) + acetic acid (64-19-7) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → 2,2'-(2,5-bis(bromomethyl)-1,4-phenylene)bis(oxy)bis(ethane-2,1-diyl) diacetate (1244947-44-1)

Conditions	Yield
With sulfuric acid; sodium bromide at 20℃;	54%

2-(ethyl sulfanylthiocarbonyl sulfanyl)-propionic acid (1035996-09-8) + 1,4-bis(2-hydroxyethoxy)benzene (104-38-1) → C22H30O6S6 (1035996-15-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 23℃; for 6h; Inert atmosphere;	53%

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 123-31-9 hydroquinone 
• 107-07-3 2-chloro-ethanol 
• 30008-10-7 sodium 4-hydroxybenzen-1-olate 
• 75-21-8 oxirane 
• 107-21-1 ethylene glycol 
• 24535-81-7 1,4-Phenylen-bis-oxyacetaldehyd 
• 5897-78-9 (4-ethoxycarbonylmethoxy-phenoxy)-acetic acid ethyl ester 

Downstream Products

• 133633-36-0 1,4-bis-(2-ethoxycarbonyloxy-ethoxy)-benzene 
• 47096-64-0 1,4-bis-(2-acetoxy-ethoxy)-benzene 
• 35057-36-4 1,4-bis-(2-methacryloyloxy-ethoxy)-benzene 
• 103330-51-4 1,6-bis-{2-[4-(2-hydroxy-ethoxy)-phenoxy]-ethoxycarbonylamino}-hexane 
• 142070-21-1 2,5-bis-(2-hydroxy-ethoxy)-aniline 
• 5471-84-1 1,4-bis(2-bromoethoxy)benzene 
• 134881-64-4 1,4-bis<2-<2-<2-<2-(4-benzyloxyphenoxy)ethoxy>ethoxy>ethoxy>ethoxy>benzene 
• 181725-36-0 {2-[4-(2-Carboxymethoxy-ethoxy)-phenoxy]-ethoxy}-acetic acid 
• 186963-33-7 {2-[4-(2-tert-Butoxycarbonylmethoxy-ethoxy)-phenoxy]-ethoxy}-acetic acid tert-butyl ester 
• 37142-37-3 1,4-Bis(2-chloroethoxy)benzene 
• 37108-78-4 2,2'-[1,4-phenylenebis(oxy)]bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) 
• 571201-62-2 C₅₂H₄₆O₆ 
• 943857-84-9 2-(4-(2-hydroxyethoxy)phenoxy)ethyl 4-methylbenzenesulfonate 
• 943857-85-0 (2-hydroxylethoxy)-4-(2-phthalimidoethoxy)benzene 

Relevant articles and documents

PHOTOCHEMICAL REARRANGEMENTS OF QUINONE MONOKETALS. SYNTHESIS OF SUBSTITUTED CYCLOPENTENONES

The irradiation of quinone ethylene monoketals in acetic acid leads in high yield to substituted 4-(alkoxycarbonyl)cyclopentenones.

Ultrasensitive electrochemical detection of methyl parathion pesticide based on cationic water-soluble pillar[5]arene and reduced graphene nanocomposite

We report a rapid, sensitive and selective electrochemical sensor based on pillar[5]arene (CP5) reduced graphene (rGO) nanohybrid-modified glassy carbon electrode CP5-rGO/GCE for the trace detection of methyl parathion (MP) by differential pulse voltammetry (DPV) for the first time. Compared to beta-cyclodextrin (β-CD)-functionalized reduced graphene (rGO)-modified GCE β-CD-rGO/GCE, the proposed CP5-rGO/GCE sensor exhibits excellent electrochemical catalytic activity, rapid response, high sensitivity, good reproducibility and anti-interference ability towards MP. The recognition mechanism of β-CD/MP and CP5/MP was studied by 1H NMR. The results indicate a higher supramolecular recognition capability between CP5 and MP compared to that between β-CD and MP. The β-CD-rGO and CP5-rGO nano-composites were prepared via a wet chemistry approach. The resulting nano-composites have been characterized by thermogravimetric analysis (TGA), fourier transform infrared spectrometry (FTIR), charge transfer resistance (Rct) and zeta potential. The CP5-rGO/GCE combines the merits of CP5 and rGO, and is used for quantitative detection of MP. It has a low detection limit of 0.0003 μM (S/N = 3) and a linear response range of 0.001-150 μM for MP. This method has been used to detect MP in soil and waste water samples with satisfactory results. This study provides a promising electrochemical sensing platform and is a promising tool for the rapid, facile and sensitive analysis of MP.

A new class of flavonoids bearing macrocyclic polyethers by stereoselective photochemical cycloaddition reaction

A new class of flavonoids bearing cyclic polyethers involving a phenyl ring was conveniently provided by the intramolecular photochemical dimerization of 2-chromonecarboxylic esters. Irradiation of 2-chromonecarboxylate with a polyether tethered at both ends promoted intramolecular [2 + 2] cyclobutane formation leading to 14- to 27-membered cyclic polyethers. The efficiency depended on the substituted position of the phenyl ring, with ortho- and meta-substituted derivatives giving cycloadducts in good chemical yields and quantum efficiencies, whereas the para-derivatives were inert toward photolysis. X-ray crystallographic analysis revealed that the stereochemistry of the macrocyclic cycloadducts exhibited C2-symmetry.

Method for synthesizing hydroquinone dihydroxyl diethyl ether

The invention relates to a method for synthesizing hydroquinone dihydroxyl diethyl ether and belongs to the technical field of synthesis of organic compounds. The method comprises the steps: carrying out synthesis by taking hydroquinone and epoxyethane as raw materials, adding hydroquinone, a ferrocene catalyst and an ether solvent into a reactor, carrying out vacuumizing, heating the reactor until hydroquinone is completely dissolved in the ether solvent under nitrogen protection, then, adding a chain extender into the reactor, heating the reactor to a polymerization reaction temperature, and carrying out hydroquinone dihydroxyl diethyl ether synthesis under polymerization reaction pressure; and after the reaction ends, carrying out cooling, and subjecting crystallizing mother liquor to normal-pressure or reduced-pressure rectification, so as to separate out the ether solvent. The hydroquinone dihydroxyl diethyl ether is synthesized by the method, the problems in the conventional technologies that the preparation process is complicated and the quality of product is poor are solved, and the obtained product is reasonable in distribution, light in color and luster and low in byproduct content.

One-pot synthesis of cyclophane-type macrocycles using manganese(iii)- mediated oxidative radical cyclization

Cyclophane-type macrocyclic compounds from 21 to 56 members having two fused dihydrofuran rings were synthesized by the manganese(iii)-mediated oxidation of terminal dienes with bis(3-oxobutanoate)s containing aromatics. The reaction detail, characterization and reaction pathways are described. The Royal Society of Chemistry 2011.

One-pot alkoxylation of phenols with urea and 1,2-glycols

A one-pot epoxide-free alkoxylation process has been developed for phenolic compounds. The process involves heating phenols and urea in 1,2-glycols at 170-190 °C using Na2CO3/ZnO as co-catalysts under atmospheric conditions. During the course of this new alkoxylation reaction, a five-membered ring cyclic carbonate intermediate, ethylene carbonate (EC) or propylene carbonate (PPC), was produced in-transit as the key intermediate and was subsequently consumed by phenols to form alkoxylated ether alcohols as final products in excellent yields. For instance, phenol, bisphenol A (BPA), hydroquinone and resorcinol were converted into their respective mono-alkoxylated ether alcohols on each of their phenolic groups in 80-95% isolated yields. In propoxylation of phenols, this approach shows great product selectivity favoring production of high secondary alcohols over primary alcohols in isomeric ratios of nearing 95/5. Since ammonia (NH3) and carbon dioxide (CO2) evolving from the reaction can be re-combined in theory into urea for re-use, the overall net-alkoxylation by this approach can be regarded as a simple condensation reaction of phenols with 1,2-glycols giving off water as its by-product. This one-pot process is simple, safe and environmentally friendlier than the conventional alkoxylated processes based on ethylene oxide (EO) or propylene oxide (PO). Moreover, this process is particularly well-suited for making short chain-length alkoxyether alcohols of phenols.

Synthesis of new cores and their use in the preparation of polyester dendrimers

Six dendrimer and dendron cores terminated by hydroxyl groups that are neither phenolic nor cleavable by hydrogenolysis have been prepared in a consistent one-pot manner from terminal allyl groups by reduction of the product of reductive ozonolysis. Some of the terminal allyl derivatives are new and others have been prepared by new methods. The well-known O-benzylidene derivative of 2,2′-bis(hydroxymethyl)propanoic acid was shown to be the cis-stereoisomer. A new AB3-type anhydride, tris(benzyloxymethyl) acetic anhydride has been prepared. It was demonstrated that these cores and dendrons could be assembled into first and second generation homo- and mixed polyester dendrimers.

Highly ordered assembly of π-stacked distyrylbenzenes by oligoadenines

A well-defined nanofibrous structure with lengths of several hundred nanometers and cross-sectional width of a single size (～6±0.5 nm) was self-assembled by oligoadenines, dA20, and thymine-appended distyrylbenzene through binary complementary A-T hydrogen bond formation and the strong π-π stacking interactions. This demonstrated a useful supramolecular self-assembling approach to control the packing order of π-conjugated molecules and provided a practical means to enhance the optical properties of a material.

Alkoxylation process for preparing ether alkanol derivatives of phenolic compounds

This invention provides an alkoxylation process for creating alkoxylating chain extension of phenolic compounds by reacting phenolic compounds with alkylene glycol and urea in the presence of suitable catalysts to obtain alkoxylated compounds, which may be used as polymer intermediates, especially for use as raw materials to synthesize polyurethane (PU) or polyester.

Preparation, characterization and luminescent properties of lanthanide complexes with a new aryl amide bridging ligand

A new aryl amide type bridging ligand 1,4-bis{[(2′-benzylaminoformyl)phenoxyl]ethoxyl}benzene (L) and its complexes with lanthanide ions (Ln = Pr, Nd, Sm, Eu, Gd, Tb, Dy, Er) were synthesized and characterized by elemental analysis, infrared spectra and electronic spectra. At the same time, the luminescent properties of the Sm, Eu, Tb and Dy complexes in solid state and the Tb complex in solvents were also investigated. At room temperature, these four complexes exhibited characteristic luminescence emissions of the central metal ions under UV light excitation and could be significant in the field of supramolecular photonic devices.