A method for production of alkyl - or alkylalkoxysilane

IPC classes for russian patent A method for production of alkyl - or alkylalkoxysilane (RU 2220134):

C07C321/18 - of an acyclic unsaturated carbon skeleton

C07C321/14 - of an acyclic saturated carbon skeleton

C07C319/14 - of sulfides

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Invention relates to compound. In formula (I) Alk represents alkyl substituent: C₄H₉, C₆H₁₃, C₁₀H₂₁, C₁₅H₃₁; R₁ represents substituents, selected from group: aryl - phenyl, 4-CH₃C₆H₄, 3-CH₃C₆H₄, 2-CH₃C₆H₄, 4-ClC₆H₄, 4-FC₆H₄, 2-FC₆H₄, 4-CH₃OC₆H₄, 4-i-PrC₆H₄, 4-i-BuC₆H₄, 4-(n-C₈H₁₇)C₆H₄, 2-naphthyl; X represents oxygen or sulphur, n=0, 1 or 2, CH_nCF_n represents fragment: if n=2 CH₂-CF₂, if n=1 CH=CF, if n=0 C≡C. Invention also relates to method of compound obtaining.

The invention relates to a method for producing alkyl - or alkylalkoxysilane, which can serve as extractants of noble metals, flotation reagents, additives in oils, and can be used as starting compounds for the production of biologically active compounds, alkyl - or alkylalkoxysilane interaction of the corresponding mercaptan with alkyl - or alkenylphenol in the presence of an alkaline agent. As the alkaline agent used alcoholate of an alkali metal, pre-prepared by the interaction of alcohol with the alkali, and the process is done, mixing consistently received the alcoholate with a mercaptan and a halide. Then produce the target product. The invention allows to increase the output of the lower alkyl - or alkylalkoxysilane and tertiary alkyl - or alkylalkoxysilane. 2 C.p. f-crystals, 6 ill.

The invention relates to a method for producing alkyl - or alkylalkoxysilane interaction of mercaptans with alkyl - or alkanolammonium, which can serve as extractants of noble metals, flotation reagents, additives to oils and can be used as starting compounds to obtain biologicheskiye of alcohol and hydrogen sulfide". Uspekhi khimii 64 (12) S. 1210-1226, 1995) gives an overview on gas-phase heterogeneous catalytic synthesis of diallylsulfide: process temperature of 350-400^oWith the catalysts of various nature (alkaline, acid). A disadvantage of the proposed method is to carry out the process at elevated temperatures. At this detail the receipt of only the lower alkylsulfides.

(USSR author's certificate 558908, 25.05.1977) describes a method for tert-dodecylthiophene-1-in-3 by reacting tert-dodecylmercaptan with diacetylene at a temperature of from -10^oC to +35^oWith methanol in the presence of powdered alkaline agent. Yield 70%. The drawback of the proposed method is the low yield of product.

A method of obtaining organic sulfides (patent of the USSR 1230465, 16.04.1986), where as serosoderjaschei connections use dithiocarbonate General formula (R₁S)₂CO., subjected to interaction with alkylhalogenide in the presence of a base 30%-aqueous solution of sodium hydroxide as a catalyst compounds of the type tetraalkylammonium. The drawback of the proposed method is the complication of the process, as you need to get the pre-dithio who eat mercaptan with alkylhalogenide in the presence of base and catalyst the Lewis acid (USSR author's certificate 1505930, 07.09.1989). As a mercaptan is used an aqueous solution containing about 15% of the mercaptans C₁-C₃in the form of sodium salts. The disadvantage of this method is the process using dilute solutions of mercaptides that after the process need to be cleaned of residual mercaptan.

Closest to the proposed invention the technical essence is a method of obtaining a lower alkylarylsulfonate from the corresponding mercaptans (USSR author's certificate 810684, 07.03.1981), in which the mercaptan is subjected to interaction with allyl chloride in the presence of sodium hydroxide at a molar ratio 0,5-1,5 : 0,5-1,5 : 0,5-1,5, accordingly, the temperature of 20-60^oWith that adopted for the prototype. The disadvantage of this method is the low output alkylarylsulfonate - 70-80% depending on the mercaptan, with the increase in length of the radical output alkylarylsulfonate reduced.

The purpose of the invention is to increase the output of the lower alkyl - or alkylalkoxysilane and higher alkyl - or alkylalkoxysilane.

This goal is achieved by the fact that in the proposed method for production of alkyl - or pre-cook the alcoholate of an alkali metal interaction of alcohol with the alkali, which is then mixed with mercaptan and then subjected to interaction with an organic halide, followed by separation of the target product in a known manner. In private cases, the execution of the invention as mercaptans can be used n-artilleryman or tert-dodecylmercaptan, and as the organic halide, alkylhalogenide selected from the group comprising ethylbromide, n-exelrod, n-activated, or alkenylamine, for example, allyl - or metalloid.

It is known ("preparation and properties of organic sulfur compounds". Ed. by L. I. Belenky, M. , "Chemistry", 1998, S. 11) that tertiary mercaptans with a large molecular weight, for example, tert-dodecylmercaptan, do not form mercaptides with alkalis and even with the alkaline metals. The proposed method allows to obtain alkyl - or alkylalkoxysilane not through mercaptide alkali metals, and directly through the mercaptan in the presence of an alcoholic solution of the alcoholate, that is, as the alkaline agent used alcoholate, which is mixed with mercaptan and then subjected to interaction with the halide.

The relationship between these features of the invention and the technical result set sub>1-C₄and potassium hydroxide, the mixture is heated to dissolve the alkaline agent, receiving the corresponding alcoholate, and then add mercaptan. To the resulting solution was added the organic halide, the reaction mass is maintained at a temperature of 20-100^oC for 0,5-5,0 hours After filtration of the reaction mixture and distillation of alcohol receive appropriate organic sulfide containing not more than 0.5% of residual mercaptan. The output of 95-98%.

The essence of the method is illustrated by the following examples.

Example 1. Getting atractylenolide. In a round bottom flask, equipped with stirrer, thermometer, dropping funnel and reflux condenser, load 255 cm³isopropyl alcohol, heated to 65^oC, add to 65.7 g of potassium hydroxide and stirred until complete dissolution, getting isopropylate potassium. The resulting solution is cooled to 50-55^oWith a load of 142.8 g of n-artilleryman. The reaction mass is then cooled to 20^oC, add 111,7 g of methyl ethyl maintaining the temperature (20-25)^oWith, heat the mass to 30^oC and stirred at (30-35)^oWith 30 minutes the resulting suspension is cooled to 20^oWith filter from potassium bromide is distilled off at atmospheric pressure isdale basic substance 99,63%, residual mercaptan is missing. The yield of 97.7%. The refractive index (n_D²⁰) 1,4570, according to literature data 1,4565 (USSR author's certificate 1154273, 1985). Range of TMR (Fig.1),

, M. D.: 0.70 to 0.76 to (6N, CH₃C-); of 1.05 to 1.14 (10H, -CH₂-); 1,38-is 1.51 (2H, CH₃CH₂-); 2,31-to 2.42 (2H, -CH₃S, 2H, CH₂CH₂-S-). An NMR spectrum¹³With (Fig.2); in CDCl₃;

_C, M. D.: 13,97 (CH₃-C); 14,7 (CH₃CH₂-S-); 22,64-29,25 (-CH₂-); 29,65 (-CH₂-CH₂-S-); 31,62 (CH₃-CH₂-S-). GC (

_beatssee; the content of, %): 1,4, 0,36; 1,9, 99,63 (atractylenolide). Found, %: S 17,98. C₁₀H₂₂S. Calculated, %: S 18,35.

Example 2. Getting ethyldimethylamine conduct similar to that described in example 1 with the difference that the solution to 65.7 g of potassium hydroxide in 210 cm³methyl alcohol at 50^oC. Then, to the obtained solution of potassium methylate are added 197,6 g of tert-dodecylmercaptan. Get 222,42 g ethyldimethylamine containing 97.8% of the basic substance. Residual mercaptan 0.5 percent. Output 96,7%. The refractive index (n_D²⁰) 1,4690. Range of TMR (Fig.3);

memorial plaques : 0,6-0,79 (N, CH₃-C); the 1.04 to 1.31 (4H, -CH₂-; 3H, CH₃-CH₂>/img>_C, M. D.: 8,63 (CH₃CH); 14,14-14,54 (CH₃CH); to 21.15 (-CH₂-) 21,09 (-CH-); 25,77 (-CH₂-S-); 28,15-28,43 (-CH-CH₃); 40-45 (-C-S-). GC (

_beatssee; the content of, %): 0,5, 0,04; 1,1, 1,14; 1,78, 0,50 (mercaptan); 2,75, 0,53; 4,0, 97,79 (acidogenicity).

Example 3. Getting metallicawelcome carried out analogously to example 1, with the difference that prepare a solution of potassium hydroxide in 396 cm³isopropyl alcohol. In the resulting solution of the alcoholate download at 50-55^oWith 197,6 g of tert-dodecylmercaptan. The reaction mass is then cooled to 20^oWith a gain of 92.8 g of metallicgold. After loading metallicgold the reaction mass is heated to 60^oC and stirred for 1.0 to 2.0 hours Get 251,9 g metallicawelcome containing 97,7% of the basic substance, the residual mercaptan of 0.15%. The yield of 98.3%. The refractive index (n_D²⁰) 1,4791. Range of TMR (Fig. 5);

, M. D. : 0,73-0.83 (M, CH₃- ); Of 1.10-1.20 (4H, -CH₂-; 6H, CH₃-C-S); TO 1.38 (3H, -CH-); and 1.8 (3H, CH₃-C=); 2,99 (2H, -CH₂S); 4,73 of 4.83 (2H, CH₂=). An NMR spectrum¹³With (Fig.6); in Dl₃;

_C, M. D.: 42,10 (-CH₂-S) 112,98 (CH₂=); 142,5 (C= CH₂). GC (

_beats, cm; content, %): 0,25, 0,13; W ill result analogously to example 1, with the difference that receive butyl potassium, which loads artilleryman and then 197,9 g of methyl Attila. Get 246,1 g dioctyladipate containing 97,6% of the basic substance, the residual mercaptan is missing. The output is 95.2%. The refractive index (n_D²⁰) 1,4590, according to literature data 1,4600 (product firms All Chem International Ltd). GC (

_beatssee; the content of, %): 0,4, 1,70; 0,6, 0,08; 1,6, 0,25; 2,6, 0,37; 7,6, 97,60 (dioctyladipate).

Example 5. Getting amitotically carried out analogously to example 3, with the difference that a mixture of ethylate and potassium tert-dodecylmercaptan add 154,96 g methyl amyl. Get 282,7 g amitotically containing 96.5% of the basic substance, the residual mercaptan is missing. Output 96,8%. The refractive index (n_D²⁰) 1,4690. GC (

_beatssee; the content of, %): 0,25, 0,16; 0,40, 1,74; 0,65, 1,56; 5,30, 96,54 (amidocarbonyl).

Example 6. Getting hexidecimal carried out analogously to example 3, with the difference that as the alkylating agent used hexyl bromide. Get 284,1 g hexidecimal containing 95,8% of the basic substance, the residual mercaptan is missing. The yield of 97.3%. The refractive index (n_D²⁰) 1,4687. >Example 7. Getting octyldodecanol carried out analogously to example 4, with the difference that as the alkylating agent used bromide octyl. The process is carried out at 100^oC for 5 hours Get 309,0 g octyldodecanol containing 97,2% of the basic substance, the residual mercaptan is missing. The yield of 97.8%. The refractive index (n_D²⁰) 1,4683. GC (

_beatssee; the content of, %): 0,60, 0,83; 0,70, 1,98; 4,43, 97,19 (octyldodecanol).

Example 8. Getting allyldimethylsulfonium carried out analogously to example 1, with the difference that in the solution, and 65.7 g of potassium hydroxide in 396 cm³isopropyl alcohol if (50-55)^oTo download 197,6 g of tert-dodecylmercaptan. The reaction mass is cooled to (20-25)^oWith a gain of 78.5 g of allylchloride, keeping the temperature (20-25)^oWith, heat the mass to 30^oC and stirred at (30-35)^o0.5-1 h After filtering from potassium chloride, distillation of isopropyl alcohol, and washing the product with water get 231,9 g allyldimethylsulfonium containing 98.1 per cent of the basic substance, the residual mercaptan is missing. Output 96,0%. The refractive index (n_D²⁰) 1,4788. GC (

_beatssee; the content of, %): 0,35, 0,20; 0,82, 1,65; 4,11, 98,15 (�t₂to C₁₂. At the same time, managed to get alkyl derivatives of tert-dodecylmercaptan. (USSR author's certificate 810684, 07.03.1981) shows that the interaction of mercaptans in the presence of an alkaline agent with alkenylsilanes with increasing length of the radicals output of organic sulfides (lower alkylarylsulfonate) decreases dramatically: from 80% to ethicallysourced to 68.1% for emeraldisle. The proposed method allows to obtain a high yield (95-98%) any alkyl - or alkylalkoxysilane as normal structure and branched, with mass fraction of residual mercaptan in the finished product does not exceed 0.5%, which is important from the point of view of environmental protection. Such a low content of residual mercaptan in the product allows you to apply special measures by further use of the product (removal of mercaptan from sulfide or special insulation product to prevent contamination of the atmosphere by mercaptan).

Claims

1. A method for production of alkyl - or alkylalkoxysilane, including the interaction of the mercaptan with alkyl - or alkenylphenol in the presence of an alkaline agent, characterized in that ctiam alcohol with the alkali, and the process is done, mixing consistently received the alcoholate with a mercaptan and a halide, and then produce the target product.

2. The method according to p. 1, characterized in that as mercaptans use n-artilleryman or tert-dodecylmercaptan.

3. The method according to p. 1, characterized in that the organic halide used alkylhalogenide selected from the group comprising ethylbromide, milbrae, n-exelrod, n-activated, or alkenylamine, for example, allyl - or metalloid.