dodecyl 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoate

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Then, 58 g of styrenated phenol, 44 g of dilaurylthiodipropionate, and 58 g of triphenyl phosphite were added to the obtained polymer latex. The mixture was coagulated at 50° C. with an aqueous 0.25% sulfuric acid so that the latex/water ratio was 1/2, and the mixture was maintained at 85° C. for 5 minutes.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: dimyristyl-3,3'-thiodipropionate (molecular weight, 571; melting point 47 to 54° C.; commercial name, DMTD "YOSHITOMI" (YOSHITOMI), SUMILIZER TPM (SUMITOMO), ANTIOX M (NICHI-YU)). distearyl-3,3'-thiodipropionate (molecular weight, 683; melting point 61 to 68° C.; commercial name, DSTP "YOSHITOMI" (YOSHITOMI), SUMILIZER TPS (SUMITOMO), ANTIOX S (NICHI-YU)). pentaerythritol-tetrakis-(β-lauryl-thiopropionate) (molecular weight, 1162; melting point >46° C.; commercial name, SEENOX 412S (CYPRO), MARK AO-412S (ADECA ARGUS), SUMILIZER TP-D (SUMITOMO)). bis[2-methyl-4{3-n-alkylthio propionyloxy}-5-tert-butylphenyl]sulfide (molecular weight, 874 to 927; commercial name, MARK AO-23 (ADECA ARGUS). phosphorus acide [1,1-biphenyl-4,4'-zyl-bis tetrakis [2,4- bis(1,1-dimethylethyl)phenyl]ester (molecular weight, 1035; melting point 75 to 95° C.; commercial name, SANDSTAB P-EPQ (SAND), IRGAFOS P-EPQ FF (CIBA-GEIGY)). 3,5-di-tert-butyl-4-hydroxy benzyl phosphite di-ethylester (molecular weight, 356; melting point 117 to 122° C.; commercial name, IRGANOX 1222 (CIBA-GEIGY)). tris (mixed mono-di-nonylphenyl-phosphite (molecular weight, 815; commercial name, MARK 329K (ADECA ARGUS), WESTON 399 (BORGWARNER)). tetra tridecyl 4,4'-butylidene bis-(3-methyl-6-t-butylphenol)-di-phosphite (molecular weight, 1238; commercial name, MARK 260 (ADECA ARGUS)). hexa tridecyl 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite (molecular weight, 1828; commercial name, MARK 522A (ADECA ARGUS)).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: dimyristyl-3,3'-thiodipropionate (molecular weight, 571; melting point 47 to 54° C.; commercial name, DMTD "YOSHITOMI" (YOSHITOMI), SUMILIZER TPM (SUMITOMO), ANTIOX M (NICHI-YU)). distearyl-3,3'-thiodipropionate (molecular weight, 683; melting point 61 to 68° C.; commercial name, DSTP "YOSHITOMI" (YOSHITOMI), SUMILIZER TPS (SUMITOMO), ANTIOX S (NICHI-YU)). pentaerythritol-tetrakis-(β-lauryl-thiopropionate) (molecular weight, 1162; melting point >46° C.; commercial name, SEENOX 412S (CYPRO), MARK AO-412S (ADECA ARGUS), SUMILIZER TP-D (SUMITOMO)). bis[2-methyl-4{3-n-alkylthio propionyloxy}-5-tert-butylphenyl]sulfide (molecular weight, 874 to 927; commercial name, MARK AO-23 (ADECA ARGUS). phosphorus acide [1,1-biphenyl-4,4'-zyl-bis tetrakis [2,4- bis(1,1-dimethylethyl)phenyl]ester (molecular weight, 1035; melting point 75 to 95° C.; commercial name, SANDSTAB P-EPQ (SAND), IRGAFOS P-EPQ FF (CIBA-GEIGY)). 3,5-di-tert-butyl-4-hydroxy benzyl phosphite di-ethylester (molecular weight, 356; melting point 117 to 122° C.; commercial name, IRGANOX 1222 (CIBA-GEIGY)). tris (mixed mono-di-nonylphenyl-phosphite (molecular weight, 815; commercial name, MARK 329K (ADECA ARGUS), WESTON 399 (BORGWARNER)). tetra tridecyl 4,4'-butylidene bis-(3-methyl-6-t-butylphenol)-di-phosphite (molecular weight, 1238; commercial name, MARK 260 (ADECA ARGUS)). hexa tridecyl 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite (molecular weight, 1828; commercial name, MARK 522A (ADECA ARGUS)).

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Then, 58 g of styrenated phenol, 44 g of dilaurylthiodipropionate, and 58 g of triphenyl phosphite were added to the obtained polymer latex. The mixture was coagulated at 50° C. with an aqueous 0.25% sulfuric acid so that the latex/water ratio was 1/2, and the mixture was maintained at 85° C. for 5 minutes.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preferably, the outer and inner layers comprise antioxidants as authorized by the European Pharmacopeia, such as butylhydroxytoluene; ethylene bis(3,3-bis(3(1,1-dimethylethyl)-4-hydroxy-phenyl) butanoate); pentaerythrityl tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate) or IRGANOX 1010®, 4,4′,4″-(2,4,6 trimethylbenzene-1,3,5-tri-yltrismethylene)-tris(2,6-bis(1,1-dimethyl-ethyl)phenol) also designated IRGANOX 1330®; octadecyle 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or IRGANOX 1076®; phosphite tris(2,4-bis(1,1-dim ethylethyl)-phenyl) or IRGAPHOS 168®; 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-s-triazine-2,4,6(1H,3H,5H)-trione or IRGANOX 3114®; 2,2′-bis(octadecyloxy)-5,5′-spirobi(1,3,2-dioxaphosphinane); dioctadecyle disulfide, didodecyl 3,3′-thiodipropanoate; dioctadecyle 3,3′-thiodipropanoate; or a mixture of seven components that are obtained from the reaction of di-tert-butyl phosphite with trichloride biphosphorus, with biphenyle and 2,4-bis(1,1-dimethylethyl)phenol; copolymer of dimethyl succinate and of (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethanol, or a mixture of at least two of these additives. or a mixture of seven components that

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preferably, the outer and inner layers comprise antioxidants as authorized by the European Pharmacopeia, such as butylhydroxytoluene; ethylene bis(3,3-bis(3(1,1-dimethylethyl)-4-hydroxy-phenyl) butanoate); pentaerythrityl tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate) or IRGANOX 1010®, 4,4′,4″-(2,4,6 trimethylbenzene-1,3,5-tri-yltrismethylene)-tris(2,6-bis(1,1-dimethyl-ethyl)phenol) also designated IRGANOX 1330®; octadecyle 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or IRGANOX 1076®; phosphite tris(2,4-bis(1,1-dim ethylethyl)-phenyl) or IRGAPHOS 168®; 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-s-triazine-2,4,6(1H,3H,5H)-trione or IRGANOX 3114®; 2,2′-bis(octadecyloxy)-5,5′-spirobi(1,3,2-dioxaphosphinane); dioctadecyle disulfide, didodecyl 3,3′-thiodipropanoate; dioctadecyle 3,3′-thiodipropanoate; or a mixture of seven components that are obtained from the reaction of di-tert-butyl phosphite with trichloride biphosphorus, with biphenyle and 2,4-bis(1,1-dimethylethyl)phenol; copolymer of dimethyl succinate and of (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethanol, or a mixture of at least two of these additives. or a mixture of seven components that

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preferably, the outer and inner layers comprise antioxidants as authorized by the European Pharmacopeia, such as butylhydroxytoluene; ethylene bis(3,3-bis(3(1,1-dimethylethyl)-4-hydroxy-phenyl) butanoate); pentaerythrityl tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate) or IRGANOX 1010®, 4,4′,4″-(2,4,6 trimethylbenzene-1,3,5-tri-yltrismethylene)-tris(2,6-bis(1,1-dimethyl-ethyl)phenol) also designated IRGANOX 1330®; octadecyle 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or IRGANOX 1076®; phosphite tris(2,4-bis(1,1-dim ethylethyl)-phenyl) or IRGAPHOS 168®; 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-s-triazine-2,4,6(1H,3H,5H)-trione or IRGANOX 3114®; 2,2′-bis(octadecyloxy)-5,5′-spirobi(1,3,2-dioxaphosphinane); dioctadecyle disulfide, didodecyl 3,3′-thiodipropanoate; dioctadecyle 3,3′-thiodipropanoate; or a mixture of seven components that are obtained from the reaction of di-tert-butyl phosphite with trichloride biphosphorus, with biphenyle and 2,4-bis(1,1-dimethylethyl)phenol; copolymer of dimethyl succinate and of (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethanol, or a mixture of at least two of these additives. or a mixture of seven components that

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3Me--THPA was produced by a combination of replacement and liquid phase aeration method. Thus, the reaction procedure of Example 8 was repeated except that the respective amounts of maleic anhydride, radical polymerization inhibitor p-tert-butylcatechol and auxiliary polymerization inhibitor dilauryl thiodipropionate were melted at 60° C. and the internal atmosphere was replaced with nitrogen gas containing 1 volume % of oxygen. Then, the same oxygen-containing nitrogen gas was introduced into the liquid phase at a rate of 5 ml/min. The procedure gave 164 g of 3Me--THPA. The investigation revealed no gels in the product. Thus, the reaction procedure of Example 8 was introduced into the liquid phase at a rate of 5 ml/min

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3Me--THPA was produced by the liquid phase aeration method. Thus, the air in a 300 ml four-necked flask similar to the one used in Example 5 was replaced with nitrogen and, then, the flask was charged with 98 g of maleic anhydride, 300 ppm of p-tert-butylcatechol by way of auxiliary polymerization inhibitor and 800 ppm of dilauryl thiodipropionate by way of auxiliary polymerization inhibitor and the charge was melted at 60° C. Then, the internal atmosphere of the reaction system was replaced with nitrogen gas, and thereafter nitrogen gas containing 1 volume % of oxygen was passed into the reaction mixture at a rate of 5 ml/min throughout the reaction. Under this atmosphere, 374 g of crude trans-1,3-pentadiene of the same composition as that used in Example 1 was continuously added at 60° C. for 4 hours. Major portion of unreactive fractions was distilled off from the reaction mixture in the course of reaction. Thereafter, the reaction mixture was treated in the same manner as in Example 5 to give 164 g of 3Me--THPA. The investigation revealed no gels in the product. Thus, the air in a 300 ml four-necked flask similar to the one used in Example 5 was passed into the reaction mixture at a rate of 5 ml/min throughout the reaction was continuously added at 60° C. for 4 hours Major portion of unreactive fractions was distilled off from the reaction mixture in the course of reaction Thereafter, the reaction mixture was treated in the same manner as in Example 5

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3Me--THPA was produced by the gas phase aeration method. Thus, the air in a 300-ml four-necked flask equipped with a stirrer, thermometer, condenser, a dropping funnel for feeding crude trans-1,3-pentadiene, and an unreactive fraction recovery vessel was replaced with nitrogen and, then, the flask was charged with 98 g of maleic anhydride, 500 ppm of p-tert-butylcatechol by way of radical polymerization inhibitor and 1000 ppm of dilauryl thiodipropionate as auxiliary polymerization inhibitor. The charge was melted at 50° to 55° C. and after the internal atmosphere was replaced with nitrogen gas, nitrogen gas containing 4% of oxygen was passed through the gas phase at a rate of 10 ml/min throughout the reaction period. Under this atmosphere, 374 g of crude trans-1,3-pentadiene of the same composition as that used in Example 1 was continuously added at 50° to 55° C. over a period of 4 hours. During the reaction, major portion of unreactive fractions was distilled off from the reaction system. After completion of addition, the reaction was conducted at 70° C. for 30 minutes. After completion of the reaction, the reaction mixture was distilled at 85° C. under atmospheric pressure and, then, under reduced pressure to remove the volatile fraction. In this manner, 164 g of 3Me--THPA was obtained. The investigation revealed no gels in the product. Thus, the air in a 300-ml four-necked flask equipped with a stirrer thermometer, condenser, a dropping funnel for feeding was passed through the gas phase at a rate of 10 ml/min throughout the reaction period was continuously added at 50° to 55° C. over a period of 4 hours During the reaction, major portion of unreactive fractions was distilled off from the reaction system After completion of addition After completion of the reaction the reaction mixture was distilled at 85° C. under atmospheric pressure under reduced pressure to remove the volatile fraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3Me--THPA was produced by the gas phase aeration method. Thus, the air in a 300-ml four-necked flask equipped with a stirrer, thermometer, condenser, a dropping funnel for feeding crude trans-1,3-pentadiene, and an unreactive fraction recovery vessel was replaced with nitrogen and, then, the flask was charged with 98 g of maleic anhydride, 500 ppm of p-tert-butylcatechol by way of radical polymerization inhibitor and 1000 ppm of dilauryl thiodipropionate as auxiliary polymerization inhibitor. The charge was melted at 50° to 55° C. and after the internal atmosphere was replaced with nitrogen gas, nitrogen gas containing 4% of oxygen was passed through the gas phase at a rate of 10 ml/min throughout the reaction period. Under this atmosphere, 374 g of crude trans-1,3-pentadiene of the same composition as that used in Example 1 was continuously added at 50° to 55° C. over a period of 4 hours. During the reaction, major portion of unreactive fractions was distilled off from the reaction system. After completion of addition, the reaction was conducted at 70° C. for 30 minutes. After completion of the reaction, the reaction mixture was distilled at 85° C. under atmospheric pressure and, then, under reduced pressure to remove the volatile fraction. In this manner, 164 g of 3Me--THPA was obtained. The investigation revealed no gels in the product. Thus, the air in a 300-ml four-necked flask equipped with a stirrer thermometer, condenser, a dropping funnel for feeding was passed through the gas phase at a rate of 10 ml/min throughout the reaction period was continuously added at 50° to 55° C. over a period of 4 hours During the reaction, major portion of unreactive fractions was distilled off from the reaction system After completion of addition After completion of the reaction the reaction mixture was distilled at 85° C. under atmospheric pressure under reduced pressure to remove the volatile fraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3Me--THPA was produced by the gas phase aeration method. Thus, the air in a 300-ml four-necked flask equipped with a stirrer, thermometer, condenser, a dropping funnel for feeding crude trans-1,3-pentadiene, and an unreactive fraction recovery vessel was replaced with nitrogen and, then, the flask was charged with 98 g of maleic anhydride, 500 ppm of p-tert-butylcatechol by way of radical polymerization inhibitor and 1000 ppm of dilauryl thiodipropionate as auxiliary polymerization inhibitor. The charge was melted at 50° to 55° C. and after the internal atmosphere was replaced with nitrogen gas, nitrogen gas containing 4% of oxygen was passed through the gas phase at a rate of 10 ml/min throughout the reaction period. Under this atmosphere, 374 g of crude trans-1,3-pentadiene of the same composition as that used in Example 1 was continuously added at 50° to 55° C. over a period of 4 hours. During the reaction, major portion of unreactive fractions was distilled off from the reaction system. After completion of addition, the reaction was conducted at 70° C. for 30 minutes. After completion of the reaction, the reaction mixture was distilled at 85° C. under atmospheric pressure and, then, under reduced pressure to remove the volatile fraction. In this manner, 164 g of 3Me--THPA was obtained. The investigation revealed no gels in the product. Thus, the air in a 300-ml four-necked flask equipped with a stirrer thermometer, condenser, a dropping funnel for feeding was passed through the gas phase at a rate of 10 ml/min throughout the reaction period was continuously added at 50° to 55° C. over a period of 4 hours During the reaction, major portion of unreactive fractions was distilled off from the reaction system After completion of addition After completion of the reaction the reaction mixture was distilled at 85° C. under atmospheric pressure under reduced pressure to remove the volatile fraction