SU175502A1 - METHOD OF SIMULTANEOUS PREPARATION OF DIALKYLMERCAPTOLS AND DIALKILMERCAPTALS OF ACETALDEHYDE - Google Patents
METHOD OF SIMULTANEOUS PREPARATION OF DIALKYLMERCAPTOLS AND DIALKILMERCAPTALS OF ACETALDEHYDEInfo
- Publication number
- SU175502A1 SU175502A1 SU935040A SU935040A SU175502A1 SU 175502 A1 SU175502 A1 SU 175502A1 SU 935040 A SU935040 A SU 935040A SU 935040 A SU935040 A SU 935040A SU 175502 A1 SU175502 A1 SU 175502A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetaldehyde
- dialkylmercaptols
- dialkilmercaptals
- simultaneous preparation
- dialkyl
- Prior art date
Links
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- FBAIECLGOSCYQM-UHFFFAOYSA-N 4-(ethenoxymethyl)-2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCC(COC=C)O1 FBAIECLGOSCYQM-UHFFFAOYSA-N 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N Butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- -1 2-methyl-2-ethyl-4-vinyloxymethyl 1, 3-dioxolane Chemical compound 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Известны способы раздельного получени диалкилмеркаптолов и диалкилмеркапталей. С целью расширени сырьевой базы предложен способ одновременного получени этих соединений, который состоит в том, что на 2,2-диалкил-4- винилоксиметил-1,3- диоксолан действуют меркаптаном при нагревании при 50-90°С в присутствии кислых катализаторов . Полученную реакционную смесь разгон ют с выделением индивидуальных продуктов. Пример. Смесь 15,8 г (0,1 моль) 2,2-диметил-4-винилоксиметил-1 ,3-диоксолана и 36 г (0,4 моль) бутилмеркаптана в присутст зии 0,2 г «-толуолсульфокислоты при перемешивании нагреваетс при 80-90°С в течение 3- 4 час. После охлаждени реакционна смесь подвергаетс фракционированию при пониженном давлении. Выделены: 1)16,4 г (79,6о/о) Дибутилмеркаптал аце88 (1 мм рт. ст.) тальдегида, т. кип 1,4889; d2o.( 0,9258. Найдено, о/о: С 58,2; Н 10,86; S 30,85. Вычислено, о/о: С 58,3; Н 10,7; S 31,1. 2)15,4 г (70э/о) Дибутилмеркаитола ацетона , т. кип. 104,5-105°С (3 мм рт. ст.) с 60,0; Н 10,9; S 29,1. Вычислено, 0/0 глицерина, т. кип. 125-128 3) 5,6 г (60о/о) (1 ММ рт. ст.), По 1,4730. Таким же способом из 2,2 диметил-4-винилоксиметил-1 ,3-диоксолана и изопропилмеркаптана , из 2-метил-2-этил-4-винилоксиметил1 ,3-диоксолана, бутилмеркаптана и изопропилмеркаптана получены диизопропилмеркапталь ацетальдегида.т. кип. ,5°С (8 мм рт.ст.) 1,4872; df 0,9326; выход 73,4о/о Дибутилметилэтилкетона , т. кип. 10 - меркаптол 1,4909; df 0,9226; 107,5°С (1 ЛЫ1 рг. ст.); По выход 75,30/0. Предмет изобретени Способ одновременного получени диалкилмеркаптолов и диалкилмеркапталей ацетал -.дегида , отличающийс тем, что 2,2-диалкил4-винилоксиметил-1 ,3-диоксолан нагревают с меркаптаном при 50-90°С в присутствии кислых катализаторов, например п-толуолсульфокислоты , с последующим выделением целевых продуктов перегонкой.Methods are known for the separate preparation of dialkyl mercaptols and dialkyl mercaptals. In order to expand the raw material base, a method has been proposed for the simultaneous production of these compounds, which consists in the fact that 2,2-dialkyl-4-vinyloxymethyl-1,3-dioxolane is acted upon by mercaptan when heated at 50-90 ° C in the presence of acid catalysts. The resulting reaction mixture is distilled to isolate individual products. Example. A mixture of 15.8 g (0.1 mol) of 2,2-dimethyl-4-vinyloxymethyl-1, 3-dioxolane and 36 g (0.4 mol) of butylmercaptan in the presence of 0.2 g of α-toluenesulfonic acid is heated at stirring 80-90 ° C for 3-4 hours. After cooling, the reaction mixture is fractionated under reduced pressure. Selected: 1) 16.4 g (79.6 o / o) Dibutyl mercaptal ace 88 (1 mmHg) of thaldehyde, m.p. 1,4889; d2o. (0.9258. Found, o / o: C 58.2; H 10.86; S 30.85. Calculated, o / o: C 58.3; H 10.7; S 31.1. 2 ) 15.4 g (70 e / o) Dibutylmercaitol acetone, t. Kip. 104.5–105 ° C (3 mmHg) with 60.0; H 10.9; S 29.1. Calculated, 0/0 glycerin, t. Kip. 125-128 3) 5.6 g (60o / o) (1 MM mercury.), According to 1.4730. In the same way, diisopropylmercaptal acetaldehyde was obtained from 2,2-dimethyl-4-vinyloxymethyl-1, 3-dioxolane and isopropyl mercaptan, from 2-methyl-2-ethyl-4-vinyloxymethyl 1, 3-dioxolane, butyl mercaptan and isopropyl mercaptan. kip , 5 ° С (8 mm Hg) 1.4872; df 0.9326; output 73,4o / o Dibutylmethyl ethyl ketone, t. Kip. 10 - mercaptol 1.4909; df 0.9226; 107.5 ° С (1 ЛЫ1 рг. Ст.); On exit 75.30 / 0. The subject of the invention is a process for the simultaneous production of dialkyl mercaptols and dialkyl mercapalts acetal-dehydate, characterized in that 2,2-dialkyl-4-vinyloxymethyl-1, 3-dioxolane is heated with mercaptan at 50-90 ° C in the presence of acid catalysts, for example p-toluenesulfonic acid, the subsequent isolation of the desired products by distillation.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU175502A1 true SU175502A1 (en) |
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