35958-30-6

Basic information

• Product Name: 2,2'-ETHYLIDENEBIS(4,6-DI-TERT-BUTYLPHENOL)
• Synonyms: VANOX 1290;2,2'-ETHYLIDENE BIS(4,6-DI-T-BUTYLPHENOL);2,2'-ETHYLIDENEBIS(4,6-DI-TERT-BUTYLPHENOL);1,1-BIS(3,5-DI-TERT-BUTYL-2-HYDROXYPHENYL)ETHANE;2,2’-ethylidenebis[4,6-bis(1,1-dimethylethyl)-pheno;2,2’-ethylidenebis[4,6-bis(1,1-dimethylethyl)-Phenol;2,2'-Ethylidenebis (4,5-di-tert.-butylphenol);Ethylidenebisdibutylphenol
• CAS NO: 35958-30-6
• Molecular Formula: C₃₀H₄₆O₂
• Molecular Weight: 438.69
• EINECS: 252-816-3
• Product Categories: Organics;Polymer Additives;Polymer Science;Stabilizers
• Mol File: 35958-30-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 162-164 °C(lit.)
• Boiling Point: 464.8 °C at 760 mmHg
• Flash Point: 177.7 °C
• Appearance: /
• Density: 0.976 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.28±0.50(Predicted)
• CAS DataBase Reference: 2,2'-ETHYLIDENEBIS(4,6-DI-TERT-BUTYLPHENOL)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-ETHYLIDENEBIS(4,6-DI-TERT-BUTYLPHENOL)(35958-30-6)
• EPA Substance Registry System: 2,2'-ETHYLIDENEBIS(4,6-DI-TERT-BUTYLPHENOL)(35958-30-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 35958-30-6(Hazardous Substances Data)

Usage

Uses

Antioxidant

Synthetic route

2,4-di-tert-Butylphenol (96-76-4) + acetaldehyde (75-07-0) → 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6)

Conditions	Yield
With benzenesulfonic acid In hexane for 24h; Reflux; Schlenk technique; Inert atmosphere; Glovebox;

tris(cyclopentadienyl)(tetrahydrofuran)samarium(III) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [(η5-C5H5)Sm(2,2'-ethylidene-bis(4,6-di-tert-butylphenoxo))(THF)2] (933453-74-8)

Conditions	Yield
In tetrahydrofuran (Ar, Schlenk) a THF-soln. of diphenol-compound was slowly added to a THF-soln. of complex, the mixt. was stirred overnight at room temp.; the solvent was removed under vac., toluene-soln. was concd.; elem. anal.;	95%

tricyclopentadienyl(tetrahydrofurane)neodymium + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [(η5-C5H5)Nd(2,2'-ethylidene-bis(4,6-di-tert-butylphenoxo))(THF)2] (933453-75-9)

Conditions	Yield
In tetrahydrofuran (Ar, Schlenk) a THF-soln. of diphenol-compound was slowly added to a THF-soln. of complex, the mixt. was stirred overnight at room temp.; the solvent was removed under vac., toluene-soln. was concd.; elem. anal.;	95%

methanol (67-56-1) + trimethyl indium (3385-78-2) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Me6In3(OMe)(2,2'-ethylidenebis(4,6-di-tert-butylphenolate)] (1187925-66-1)

Conditions	Yield
In methanol; diethyl ether byproducts: CH4; (N2); std. Schlenk technique; soln. of MeOH in Et2O was added to stirredsoln. of Me3In in Et2O at -76°C; warmed to room temp.; soln. of ligand in Et2O was added at 0°C; warmed to room temp.; elem. anal.;	94%

(1,4,7,10-tetraoxacyclododecane) (294-93-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → C38H61LiO6

Conditions	Yield
With n-butyllithium In hexane; toluene at 20℃; for 12h; Inert atmosphere;	94%

(η5-C5H5)3Yb(tetrahydrofuran) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [(η5-C5H5)Yb(2,2'-ethylidene-bis(4,6-di-tert-butylphenoxo))(THF)2] (933453-73-7)

Conditions	Yield
In tetrahydrofuran (Ar, Schlenk) a THF-soln. of diphenol-compound was slowly added to a THF-soln. of complex, the mixt. was stirred overnight at room temp.; the solvent was removed under vac., toluene was added to extract, -10°C; elem. anal.;	93%

titanium(IV) tetraethanolate + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Ti2(μ-OEt)2(2,2-ethylidenebis(4,6-di-tert-butylphenol)(-2H))2(OEt)2] (851091-55-9)

Conditions	Yield
In hexane byproducts: EtOH; to rapidly stirred hexane soln. of edbp (4.9 mmol) Ti(OEt)4 (4.9 mmol) added, stirred for 48 h at room temp.; filtered, washed (hexane), recrystd. (hexane/toluene 1:1) at room temp.;elem. anal.;	92%

tetrahydrofuran (109-99-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [EDBPH*K*(THF)2]

Conditions	Yield
With potassium	92%

tetrahydrofuran (109-99-9) + trimethylaluminum (75-24-1) + sodium (7440-23-5) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [(2,2-ethylidenebis(4,6-di-tert-butylphenolato))Al(CH3)2Na(tetrahydrofuran)2] (1229666-03-8)

Conditions	Yield
In tetrahydrofuran; hexane under N2; soln. of ethylidenebis(phenol) deriv. and Na in THF stirred at50°C for 4.0 h, Al(CH3)3 in hexane added slowly, mixt. stirred f or 12 h; evapn. under vac., residue dissolved in THF, hexane added, soln. filtered through Celite, filtrate stored at room temp. for several d; elem. anal.;	91%

WO[OC(CH3)3]4 (58832-09-0) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + acetonitrile (75-05-8) → [W(O)(di-phenol 2,2’-ethylidenebis(4,6-di-tertbutylphenol))2]·MeCN

Conditions	Yield
Stage #1: WO[OC(CH3)3]4; 2,2-ethylidenebis(4,6-tert-butylphenol) In diethyl ether for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: acetonitrile Inert atmosphere; Schlenk technique;	91%

tris(1,2-ethanediolate)tungsten(VI) (54153-67-2) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [C(CH3)3C6H2C(CH3)3O]2CHCH3W(OC2H4O)2

Conditions	Yield
In toluene byproducts: 1,2-ethanediol; mixed at reflux; distilled (toluene, 4 h), evapd., chromy.(silica gel-CH2Cl2), crystd.(CH3CN), dried.(vac.) 40°C for 6 h, elem. anal.;	90%

titanium(IV) isopropylate (546-68-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Ti(2,2-ethylidenebis(4,6-di-tert-butylphenol)(-2H))(O(i-Pr))2] (709671-04-5)

Conditions	Yield
In hexane byproducts: i-PrOH; to rapidly stirred hexane soln. of edbp (4.9 mmol) Ti(O(i-Pr))4 (4.9 mmol) added, stirred for 48 h at room temp.; filtered, washed (hexane), recrystd. (CH2Cl2); elem. anal.;	90%
In toluene byproducts: isopropanol; complex obtained by react. of CH3CH2(C6H2(OH)(t-Bu)2)2 and Ti(OPri)4 in toluene at 60°C for 3 h; elem. anal.; complex washed with toluene and azeotropic distilated;

18-crown-6 ether (17455-13-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → C42H69NaO8

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran; toluene at 20℃; for 12h; Inert atmosphere;	90%

toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester (50586-80-6) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → 2,4-di-tert-butyl-6-(1-(3,5-di-tert-butyl-2-(2-(2-methoxyethoxy)ethoxy)phenyl)ethyl)phenol (1264748-97-1)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 12h;	89%

tetrahydrofuran (109-99-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → (2,2'-ethylidenebis(4,6-di-tert-butylphenolato))Li∙(tetrahydrofuran)3

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h;	88%

tetrahydrofuran (109-99-9) + trimethylaluminum (75-24-1) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + sodium hydroxide (1310-73-2) → [(2,2-ethylidenebis(4,6-di-tert-butylphenolato))Al(CH3)(μ2-OH)Na(THF)3]

Conditions	Yield
In tetrahydrofuran; hexane under N2; soln. of ethylidenebis(phenol) deriv. and NaOH in THF stirred at 50°C for 12 h, Al(CH3)3 in hexane added slowly, mixt. stirred for 12 h; evapn. under vac., residue dissolved in THF, hexane added, soln. filtered through Celite, filtrate stored at room temp. for several h; elem. anal.;	88%

hexane (110-54-3) + titanium(IV) bromide (7789-68-6) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Ti(Br)2(6,6'-(ethane-1,1-diyl)bis(2,4-di-tert-butylphenolato))]*hexane

Conditions	Yield
at 60℃; for 16h; Inert atmosphere;	88%

2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → C30H45O2(1-)*Na(1+)

Conditions	Yield
With sodium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	87%

diethylaluminium chloride (96-10-6) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → chloro-(2,2'-ethylidene-bis(4,6-di-tert-butylphenolato))aluminum(III) (251310-99-3)

Conditions	Yield
In hexane dry N2-atmosphere; addn. of Et2AlCl to ligand at 0°C, stirring for 3 h; evapn. (vac.), dissoln. in PhMe, crystn. on cooling to room temp.; elem.anal.;	86%

18-crown-6 ether (17455-13-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → C42H69KO8

Conditions	Yield
With potassium hexamethylsilazane In hexane; toluene at 20℃; for 12h; Inert atmosphere;	86%

tetrahydrofuran (109-99-9) + trimethylaluminum (75-24-1) + sodium (7440-23-5) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + benzyl alcohol (100-51-6) → [(2,2'-ethylidenebis(4,6-di-tert-butylphenol(-2H))AlMe(μ2-OBn)Na(THF)3] (1295558-43-8)

Conditions	Yield
In tetrahydrofuran EDBP-H2, AlMe3, BnOH, Na (1:1:1:1 molar ratio) in THF; NMR;	85%

diethyl ether (60-29-7) + trimethylaluminum (75-24-1) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → (diethyl ether)methyl(2,2'-ethylidenebis(4,6-di-tert-butylphenato))aluminum(III)*0.5(diethyl ether)

Conditions	Yield
In diethyl ether; toluene under N2; soln. of AlMe3 in toluene added slowly to ice cold (0°C) soln. of ligand (molar ratio 1.2:1) in Et2O; stirred for 2.5 h; dried in vac.; extd. with Et2O; filtered; filtrate concd.; cooled to -20°C; elem. anal.;	84%

trimethylaluminum (75-24-1) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → bis[methyl(2,2'-ethylidenebis(4,6-di-tert-butylphenato))aluminum(III)]

Conditions	Yield
In hexane; toluene under N2; soln. of AlMe3 in toluene added slowly to ice cold (0°C) soln. of ligand (molar ratio 1.2:1) in hexane; stirred for 2.5 h; dried in vac.; dissolved in hot (85°C) toluene; cooled to ambient temp.; elem. anal.;	84%

2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + dimethyl sulfate (77-78-1) → 2,4-di-tert-butyl-6-(1-(3,5-di-tert-butyl-2-methoxyphenyl)ethyl)phenol (1203204-44-7)

Conditions	Yield
Stage #1: 2,2-ethylidenebis(4,6-tert-butylphenol) With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: dimethyl sulfate In acetone for 48h;	84%

tetrahydrofuran (109-99-9) + neodymium trichloride (10024-93-8) + trimethylsilylmethyllithium (1822-00-0) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → bis(6,6'-(ethane-1,1-diyl)bis(2,4-di-tert-butylphenolate)NdLi(THF)3 (1350461-07-2)

Conditions	Yield
In tetrahydrofuran NdCl3 reacted with 3 equiv. of LiCH2SiMe3 in THF, treated in one portionwith ligand (2 equiv.), reacted at room temp.;	83%

18-crown-6 ether (17455-13-9) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → C42H69O8Rb

Conditions	Yield
With rubidium tert-butoxide In toluene at 20℃; for 12h; Inert atmosphere;	83%

titanium(IV) iodide (7720-83-4) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Ti(I)2(6,6'-(ethane-1,1-diyl)bis(2,4-di-tertbutylphenolate))]

Conditions	Yield
In hexane at 60℃; for 16h; Inert atmosphere;	83%

2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + benzyl alcohol (100-51-6) → 2CHCH2(C6H2OH(C4H9)2)2(1-)*2Li(1+)*2(C6H5CH2OH)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane at 0℃; for 1h;	81%

tetrahydrofuran (109-99-9) + trimethylaluminum (75-24-1) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → (tetrahydrofuran)methyl(2,2'-ethylidenebis(4,6-di-tert-butylphenato))aluminum(III)

Conditions	Yield
In tetrahydrofuran; toluene under N2; soln. of AlMe3 in toluene added slowly to ice cold (0°C) soln. of ligand (molar ratio 1.2:1) in THF; stirred for 2.5 h; dried in vac.; extd. with toluene; filtered; filtrate concd.; cooled to-20°C; elem. anal.;	81%

2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) + dimethylsilicon dichloride (75-78-5) → 2,4,8,10-Tetra-t-butyl-6,6,12-trimethyl-12H-dibenzo[d,g][1,3,2]dioxasilocin (88946-12-7)

Conditions	Yield
With triethylamine In toluene Ambient temperature;	79%
With triethylamine	79%
With triethylamine In toluene for 2h; Ambient temperature;

diethyl ether (60-29-7) + iodine (7553-56-2) + trimethylaluminum (75-24-1) + 2,2-ethylidenebis(4,6-tert-butylphenol) (35958-30-6) → [Al(2,2'-ethylidenebis(4,6-di-tert-butylphenolato))I(Et2O)] (264916-84-9)

Conditions	Yield
In diethyl ether; toluene (N2); AlMe3/toluene added slowly to I2/toluene at 0°C; after 20 min, ligand/ether added, stirred for 2 h; dried (vac.), extd. (ether), concd., crystd. (cooling); elem. anal.;	79%

Upstream product

• 96-76-4 2,4-di-tert-Butylphenol 
• 75-07-0 acetaldehyde 

Downstream Products

• 154437-29-3 2-<1-<3,5-bis(1,1-dimethylethyl)-2-<<2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo<1,3,2>dioxaphosphepin-6-yl>oxy>phenyl>ethyl>-4,6-bis(1,1-dimethylethyl)phenol 
• 116954-20-2 2,2'-ethylidenebis(4,6-di-tert-butylphenyl)fluorophosphite 
• 199737-28-5 Mo2(NMe2)2(μ-2,2'-ethylidenebis(4,6-di-tert-butylphenolate)2) 
• 862130-14-1 2,2'-ethylidenebis(4,6-di-tert-butylphenyl)-4-nitrophenylphosphite 
• 1200399-03-6 [V(Np-(Cl)C₆H₄)(2,2'-CH₃CH[4,6-(t-Bu)2C₆H₂O]2)(OEt)]2*dichloromethane 
• 1199604-16-4 [V(Np-(OCH₃)C₆H₄)(2,2'-CH₃CH[4,6-(t-Bu)2C₆H₂O]2)(Oi-Pr)]2 
• 1199604-14-2 [V(Np-(Cl)C₆H₄)(2,2'-CH₃CH[4,6-(t-Bu)2C₆H₂O]2)(Oi-Pr)]2 
• 1199604-15-3 [V(Np-(CF₃)C₆H₄)(2,2'-CH₃CH[4,6-(t-Bu)2C₆H₂O]2)(Oi-Pr)]2 
• 1200399-00-3 [V(Np-(CF₃)C₆H₄)(2,2'-CH₃CH[4,6-(t-Bu)2C₆H₂O]2)(On-Pr)]2 
• 1203204-44-7 2,4-di-tert-butyl-6-(1-(3,5-di-tert-butyl-2-methoxyphenyl)ethyl)phenol 
• 1264748-97-1 2,4-di-tert-butyl-6-(1-(3,5-di-tert-butyl-2-(2-(2-methoxyethoxy)ethoxy)phenyl)ethyl)phenol 
• 1295558-43-8 [(2,2'-ethylidenebis(4,6-di-tert-butylphenol(-2H))AlMe(μ2-OBn)Na(THF)3] 
• 264916-85-0 [(Ph₃P=O)Al(2,2'-ethylidenebis(4,6-di-tert-butylphenolato))I] 
• 264916-86-1 [Al(2,2'-ethylidenebis(4,6-di-tert-butylphenolato))(triphenylphosphine oxide)]I 

Relevant articles and documents

Coordinating effect in ring-opening polymerization of ε-caprolactone using aluminum complexes bearing bisphenolate as catalysts

A series of Al complexes bearing diphenolate ligands was synthesized and their application for the ring-opening polymerization of ε-caprolactone was studied. Positional variation of the substituent on the aryl ring of the RCH(4,6-di-t-butylphenol)2 ligand was shown to have a considerable influence on the catalysis result. Complexes with a ortho-substituent showed greater catalytic activity than those with a para-substituent. Substitutions of an aryl moiety by H or methyl groups resulted in the catalytic activity falling between that of the ortho-substitution Al complexes and that of the para ones. Our results demonstrate that the coordinated functional group in the ortho-position of the phenyl ring could increase the catalytic activity. Moreover, X-rays of the structure and DFT analysis revealed that the coordinated functional group in the ortho-position could bridge two Al centers resulting in the transformation of a dinuclear Al complex with bridging benzyl alkoxide into a complex with terminal benzyl alkoxide, further promoting the efficacy of the initiator.

Thioether substituted hydroxybenzophenones and stabilized compositions

2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.

Amorphous modification of 1,1',1"-nitrilo(tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl] phosphite)

The new amorphous modification of 1,1',1"-nitrilo{tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl)]phosphite } is obtained by cooling rapidly said compound from the melt to ambient temperature. This amorphous form is an effective process stabilizer for polyolefins, particularly polypropylene.