32509-66-3

Usage

Uses

Used in Polymer Industry:
Ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate] is used as a stabilizer for polymers for its high resistance to hydrolysis and high temperatures. This application helps in preventing the oxidative degradation of polymers, which can lead to a decline in their mechanical and physical properties over time.
Used in Plastics and Rubber Industry:
In the plastics and rubber industry, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate] is used as an additive to enhance the stability and durability of the materials. Its antioxidant properties help in protecting the plastics and rubber from the harmful effects of heat, light, and oxygen, ensuring that they maintain their structural integrity and performance even under harsh conditions.
Used in Adhesives and Coatings Industry:
Ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate] is also utilized in the adhesives and coatings industry as an additive to improve the resistance of these materials to oxidative degradation. By incorporating this antioxidant into the formulations, the shelf life and performance of adhesives and coatings can be significantly enhanced, making them more reliable and durable for various applications.
Used in Lubricant Industry:
In the lubricant industry, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate] is used as an additive to improve the oxidative stability of lubricants. This helps in reducing the formation of sludge and deposits in the lubricated systems, thereby extending the life of the lubricants and ensuring the smooth operation of the machinery.
Overall, ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate] is a versatile antioxidant compound that finds applications in various industries due to its ability to protect materials from oxidative degradation, ensuring their longevity and performance.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C50H66O8/c1-45(2,3)35-25-31(15-19-39(35)51)49(13,32-16-20-40(52)36(26-32)46(4,5)6)29-43(55)57-23-24-58-44(56)30-50(14,33-17-21-41(53)37(27-33)47(7,8)9)34-18-22-42(54)38(28-34)48(10,11)12/h15-22,25-28,51-54H,23-24,29-30H2,1-14H3

Synthetic route

3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyric acid methyl ester (32509-69-6) + ethylene glycol (107-21-1) → ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3)

Conditions	Yield
With lithium methanolate at 160 - 180℃; under 5 - 10 Torr; for 20h; Reagent/catalyst; Inert atmosphere;	62%

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) + bis(2,4-di-tert-butylphenyl)phosphorous oxychloride → C162H230O16P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	90%
With triethylamine In toluene at 0 - 20℃; Solvent; Schlenk technique;	90%

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) → C50H62Cl8O8P4

Conditions	Yield
With triethylamine; phosphorus trichloride In tetrahydrofuran at 0 - 20℃;	78%
With triethylamine; phosphorus trichloride In tetrahydrofuran at 0 - 20℃;	78%

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) + binaphthol chlorophosphite (137156-22-0, 171878-71-0, 155613-52-8) → C130H110O16P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	74%

6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin (16611-68-0) + ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) → C98H94O16P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	54%
With triethylamine In tetrahydrofuran at 0 - 20℃;

2-chloro-4,4',5,5'-tetraphenyl-1,3,2-dioxaphospholane (1033130-16-3) + ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) → C154H142O16P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 70℃;	49%
With triethylamine In tetrahydrofuran at 0 - 20℃;

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) + 4,8-di-tert-butyl-6-chloro-2,10-dimethoxy-5,7,6-dioxaphosphadibenzo[a,c]cycloheptene (240134-26-3, 108609-95-6) → C130H158O24P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	48%

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) + 4,8-di-tert-butyl-6-chloro-2,10-dimethoxy-5,7,6-dioxaphosphadibenzo[a,c]cycloheptene (240134-26-3, 108609-95-6) → C138H174O24P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	48%

ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate] (32509-66-3) + [(R)-1,1'-binaphthyl-2,2'-diyl]chlorophosphite → C130H110O16P4

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;

Upstream product

• 32509-69-6 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyric acid methyl ester 
• 107-21-1 ethylene glycol 

Relevant academic research and scientific papers

Preparation method of hindered phenol antioxidant and intermediate thereof

The invention provides a preparation method of a hindered phenol antioxidant and an intermediate thereof. The preparation method comprises the following steps of: carrying out Friedel-Crafts reactionon a compound a and a compound b under the action of a main catalyst organic sulfonic acid and/or trifluoroacetic acid and a cocatalyst to obtain a hindered phenol antioxidant intermediate shown as aformula I; wherein the structural formulas of the compound a, the compound b and formula I are shown as the specification, wherein R1 is selected from H and substituted or unsubstituted alkyl of C1-C4, and R2 is selected from substituted or unsubstituted alkyl of C1-C4. According to the preparation of the hindered phenol antioxidant intermediate, the organic sulfonic acid and/or trifluoroacetic acid are/is adopted to replace a hydrogen chloride gas catalyst, so that the reaction safety is greatly improved, the requirements on equipment are reduced, and the equipment cost is also reduced.

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.

Lubricant composition

A composition comprising a) a lubricant or a hydraulic fluid and b) at least one compound of the general formula I STR1 in which x=1 or 2 and, if x=1, R is as defined for R1 or R3 --O-- or, if x=2, R is as defined for R8, and R1 and R3 are, for example, alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, or alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3, or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR2 or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3 and interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR3 and R2 is NR4 R5, --OR6 or --SR7, and R4 and R5 are identical or different and are, for example, --H, alkyl, phenyl, naphthyl, aralkyl or alkaryl, or R4 and R5, together with the N atom linking them, form, for example, a piperidine or morpholine radical, and R6 and R7 can be alkyl which may be interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR4 or are, for example, phenyl, naphthyl, alkaryl or aralkyl, and R8 can be alkylene which may be interrupted by at least one --O-- group or alkylidene which may be interrupted by at least one --O-- group. Some of the compounds of the formula I are novel. The compositions show an improved stability towards oxidative degradation, confer protection under extreme pressures and reduce frictional wear.

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.

3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers

Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.

Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite]

The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures. The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.

Substituted 1,4-diamino-2-butene stabilizers

N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.

Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions

Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.

Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers

Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.

Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives

1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.