3-triethoxysilylpropane-1-thiol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Crompton Corp. of Greenwich, Conn.), 433 grams of triethylamine, and 3,000 ml hexane. The solution was cooled in an ice bath, and 693 grams of octanoyl chloride were added over a two hour period via the addition funnel. After addition of the acid chloride was complete, the mixture was filtered two times, first through a 0.1 μm filter and then through a 0.01 μm filter, using a pressure filter, to remove the salt. The solvent was removed under vacuum. The remaining yellow liquid was vacuum distilled to yield 1,349 grams of octanoylthiopropyltriethoxysilane as a clear, very light yellow liquid. The yield was 87 percent. Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel The solution was cooled in an ice bath the mixture was filtered two times first through a 0.1 μm filter through a 0.01 μm filter filter to remove the salt The solvent was removed under vacuum distilled

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

Procedure: Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 3-mercaptopropyltriethoxysilane (1,021 grams, 3.73 moles purchase as SILQUEST® A-1891 silane from General Electric Company), triethylamine (433 grams), and hexane (3,000 ml). The solution was cooled in an ice bath, and octanoyl chloride (693 grams, 4.25 moles) were added over a two hour period via the addition funnel. After addition of the acid chloride was complete, the mixture was filtered two times, first through a 0.1 μm filter and then through a 0.01 μm filter, using a pressure filter, to remove the salt. The solvent was removed under vacuum. The remaining yellow liquid was vacuum distilled to yield 1,349 grams of octanoylthiopropyltriethoxysilane as a clear, very light yellow liquid. The yield was 87 percent. Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel The solution was cooled in an ice bath the mixture was filtered two times first through a 0.1 μm filter through a 0.01 μm filter filter to remove the salt The solvent was removed under vacuum distilled

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

Procedure: A 1-quart (0.946 l) glass reactor was charged with 400 ml of chloroform, 55.4 g (0.21 mole) of N-cyclohexylthiophthalimide, and 47.6 g (0.20 mole) of 3-mercaptopropyltriethoxysilane dissolved in 400 ml of chloroform. The reaction was stirred and allowed to stand overnight to give white needles of phthalimide (35.2 g) which were separated by filtration and identified by mass spectrometry analysis. The solvent was distilled from the filtrate to give 56.9 g of an oil identified as cyclohexyl-3-dithiopropyltriethoxysilane by mass spectrometry analysis. This oil (53 g) was dissolved in 100 ml of acetone and homogeneously dispersed into N330 carbon black, with the acetone being stripped away.

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suitable method for the preparation of bis-[γ-(trialkoxysilyl)-propyl]-disulfides is disclosed in copending application Ser. No. 529,203 filed Dec. 3, 1974 entitled "Bis-[γ-(Trialkoxysilyl)-Propyl]-Disulfides of High Purity", the disclosure of which is hereby incorporated specifically herein by reference. According to the process therein disclosed such a disulfide can be prepared by reacting a γ-chloropropyl-triethoxy silane with thiourea and sodium iodide in alcohol for 24 hours at ebullition. After the reaction mixture is cooled to room temperature and over a period of 4 hours a strong current of ammonia is passed through the solution. This causes ammonium chloride to precipitate. The filtrate and precipitate are separated and the filtrate can be concentrated whereby to obtain γ-mercaptopropyl-triethoxy silane. This latter material can be reacted with sulfuryl chloride in a solvent such as anhydrous benzene at a temperature of +8 - + 12°C. The SO2Cl2 is added to the γ-mercapto-propyl-triethoxy silane dropwise over a period of about 55 minutes. Sulfur dioxide and hydrogen chloride gas which are formed are removed by a nitrogen gas purge. After a period of about 6 hours at room temperature with stirring triethylamine can be added whereby to precipitate the amine hydrochloride. The filtrate is then fractionally distilled whereby there is recovered a bis-[γ-(triethoxysilyl)-propyl]-disulfide. can be prepared for 24 hours This causes ammonium chloride to precipitate The filtrate and precipitate are separated the filtrate can be concentrated whereby

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

Procedure: A suitable method for the preparation of bis-[γ-(trialkoxysilyl)-propyl]-disulfides is disclosed in copending application Ser. No. 529,203 filed Dec. 3, 1974 entitled "Bis-[γ-(Trialkoxysilyl)-Propyl]-Disulfides of High Purity", the disclosure of which is hereby incorporated specifically herein by reference. According to the process therein disclosed such a disulfide can be prepared by reacting a γ-chloropropyl-triethoxy silane with thiourea and sodium iodide in alcohol for 24 hours at ebullition. After the reaction mixture is cooled to room temperature and over a period of 4 hours a strong current of ammonia is passed through the solution. This causes ammonium chloride to precipitate. The filtrate and precipitate are separated and the filtrate can be concentrated whereby to obtain γ-mercaptopropyl-triethoxy silane. This latter material can be reacted with sulfuryl chloride in a solvent such as anhydrous benzene at a temperature of +8 - + 12°C. The SO2Cl2 is added to the γ-mercapto-propyl-triethoxy silane dropwise over a period of about 55 minutes. Sulfur dioxide and hydrogen chloride gas which are formed are removed by a nitrogen gas purge. After a period of about 6 hours at room temperature with stirring triethylamine can be added whereby to precipitate the amine hydrochloride. The filtrate is then fractionally distilled whereby there is recovered a bis-[γ-(triethoxysilyl)-propyl]-disulfide. can be prepared for 24 hours This causes ammonium chloride to precipitate The filtrate and precipitate are separated the filtrate can be concentrated whereby

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of α-damascone (9.60 g; 50.0 mmol) and 3-mercaptopropyltriethoxysilane (95% pure, 12.52 g, 50.0 mmol) in THF (40 ml) was treated with DBU (1.52 g, 10.0 mmol) and stirred at 40° C. for 90 min. The reaction solution was treated with 5% HCl, extracted twice with ether, washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl, dried over Na2SO4 and concentrated at 70° C./0.01 mbar. The reaction yielded 21.2 g (99%). of crude product: extracted twice with ether washed with water, saturated aqueous NaHCO3 with saturated aqueous NaCl, dried over Na2SO4 concentrated at 70° C./0.01 mbar The reaction yielded 21.2 g (99%)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of α-damascone (9.60 g; 50.0 mmol) and 3-mercaptopropyltriethoxysilane (95% pure, 12.52 g, 50.0 mmol) in THF (40 ml) was treated with DBU (1.52 g, 10.0 mmol) and stirred at 40° C. for 90 min. The reaction solution was treated with 5% HCl, extracted twice with ether, washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl, dried over Na2SO4 and concentrated at 70° C./0.01 mbar. The reaction yielded 21.2 g (99%). of crude product: extracted twice with ether washed with water, saturated aqueous NaHCO3 with saturated aqueous NaCl, dried over Na2SO4 concentrated at 70° C./0.01 mbar The reaction yielded 21.2 g (99%)