SU65065A1 - Method for producing saccharin - Google Patents
Method for producing saccharinInfo
- Publication number
- SU65065A1 SU65065A1 SU3953A SU3953A SU65065A1 SU 65065 A1 SU65065 A1 SU 65065A1 SU 3953 A SU3953 A SU 3953A SU 3953 A SU3953 A SU 3953A SU 65065 A1 SU65065 A1 SU 65065A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- saccharin
- mixture
- ester
- chlorine
- Prior art date
Links
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 title description 5
- 229940081974 saccharin Drugs 0.000 title description 5
- 235000019204 saccharin Nutrition 0.000 title description 5
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- AJQLEJAVGARHGQ-UHFFFAOYSA-N dithiosalicylic acid Chemical compound OC1=CC=CC=C1C(S)=S AJQLEJAVGARHGQ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- -1 sulfobenzoic acid ester Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 229930189308 salarin Natural products 0.000 description 1
- 101150061131 salarin gene Proteins 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
r NcOOH HOOC/ ROH ( ROH - спирт). эфир тио-иЛИ диггиосалициловой кислоты (или смесь этих эфиров) получаетс с хорошим .выходом при нагревании дитиосалищиловой кислоты с соответствующим спиртом в автоклаве под давлением при температуре выще 180°С с катализатором (H2SO4, ZnCb) ИЛИ1 без него. Хлорга«гидрид эфира сульфобензойной кислоты образуетс с хорошим выходом при пропускании хлора .в смесь эфира тио- или дитиосалициловой «ислоты (или смеси эфиров) с соответствующим сйиртом . COOR OC/Nci- СООК NHs .SOaCi ч/ / Действве.м раствора аммиака хлорангидрид переводитс в сахарин по способам, описанным в литературе . Пример. часть дитиосалициловой кислоты, 0,8 ч. метилового или этилового спирта и 0,05 ч. хлористого цинка нагреваютс в автх)клаве при температуре 185-IQC C в течение 10--12 часов. В полученную после автоклавировани смесь, содержащую метил- или этилдитиосалицилат , пропускают хлор в количестве , почти равном вычисленному по реакции. Жидка смесьr NcOOH HOOC / ROH (ROH - alcohol). The ester of thio-OR or diggiosalicylic acid (or a mixture of these esters) is obtained with a good yield by heating dithiosalicylic acid with the corresponding alcohol in an autoclave under pressure at a temperature higher than 180 ° C with a catalyst (H2SO4, ZnCb) OR1 without it. The chlorine "hydride of sulfobenzoic acid ester is formed with a good yield by passing chlorine into a mixture of thio- or dithiosalicylic ester" (or a mixture of esters) with an appropriate syirt. COOR OC / Nci-COOK NHs .SOaCi h / / The action of the ammonia solution of the acid chloride is converted to saccharin according to the methods described in the literature. Example. a part of dithiosalicylic acid, 0.8 parts of methyl or ethyl alcohol and 0.05 parts of zinc chloride are heated in the autoclave at a temperature of 185-IQC C for 10-12 hours. The mixture obtained after autoclaving containing methyl or ethyl dithiosalicylate is passed in chlorine in an amount almost equal to that calculated by the reaction. Liquid mixture
после хлорировани раэмешИваетс с 1-2 объемами холодной воды (лучше с н-ебольшим количеством льда). Отсто вшийс нижний слой сулъфо хлорид а при температуре 10-20°С размешиваетс с 10-20процентньш раствором аймиака. После окончани реакции жидкость нагреваетс до кипени , сливаетс со смолистого остатка, обрабатываетс небольшим количеством раствора КМпО4 (2-3% КМпО4 от саларина ) и фильтруетс . Сахарин осаждаетс мйнеральиой кислотой. Продукт слегка окрашен. Достаточмо чистый продукт получаетс приafter chlorination, it is mixed with 1-2 volumes of cold water (preferably with a large amount of ice). The separated bottom layer of sulfo chloride and at a temperature of 10–20 ° C is stirred with a 10–20% solution of aimiac. After completion of the reaction, the liquid is heated to boiling, drained from the gummy residue, treated with a small amount of KMnO4 solution (2-3% KMnO4 from salarin) and filtered. Saccharin is precipitated by minergic acid. The product is slightly colored. A sufficiently pure product is obtained by
повторном переводе в нагрозую солЬ, обработке КМпО4 и оса-ждении .reassigned to saline, treatment of KMnO4 and precipitated.
Предмет изобретени Subject invention
Способ получени сахарина, о тл и ч а ю ш и и с тем, что продукт этерификации тиосалициловой кислоты или соответствуюшей дисульфндокислоты (дитиосалициловой кислоты) или же их смеси, без выделени сложного эфира в чистом состо нии, обрабатывают вычисленным количеством хлора, образовавшийс сульфохлорид превраш; ют в сахарин нз вестными npHep 3(Nf иThe method of obtaining saccharin, tl and h and w and the fact that the esterification product of thiosalicylic acid or the corresponding disulphonic acid (dithiosalicylic acid) or their mixture, without isolating the ester in a pure state, is treated with a calculated amount of chlorine, the resulting sulfonyl chloride is ; in saccharin are known npHep 3 (Nf and
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU3953A SU65065A1 (en) | 1944-05-26 | 1944-05-26 | Method for producing saccharin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU3953A SU65065A1 (en) | 1944-05-26 | 1944-05-26 | Method for producing saccharin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU65065A1 true SU65065A1 (en) | 1944-11-30 |
Family
ID=48245471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU3953A SU65065A1 (en) | 1944-05-26 | 1944-05-26 | Method for producing saccharin |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU65065A1 (en) |
-
1944
- 1944-05-26 SU SU3953A patent/SU65065A1/en active
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