PL443B1 - Method for producing esters of diethyl dioxide sulphide. - Google Patents
Method for producing esters of diethyl dioxide sulphide. Download PDFInfo
- Publication number
- PL443B1 PL443B1 PL443A PL44321A PL443B1 PL 443 B1 PL443 B1 PL 443B1 PL 443 A PL443 A PL 443A PL 44321 A PL44321 A PL 44321A PL 443 B1 PL443 B1 PL 443B1
- Authority
- PL
- Poland
- Prior art keywords
- sulphide
- diethyl dioxide
- diethyl
- producing esters
- parts
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- 229950006389 thiodiglycol Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- -1 sulfuric acid ester Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Description
Stwierdzono, ze mozna otrzymac siarczek dwutlenku dwuetylowego przez nagrzewanie go z kwasami organiczne- mi lub nieorganicznemi. Pod mianem kwasów rozumiemy równiez te, zawie¬ rajace wodorotlenek zwiazki, które, jak to ma miejsce np. z wodorotlenkiem glinu, kwasza bardzo slabo i posiadaja charakter dwoisty. Szczególnie przy zastosowaniu kwasów mineralnych na¬ lezy dbac o dobranie warunków tak la¬ godnych, aby nie zaszlo latwo mogace sie przytrafic powstawanie siarczku dwu- etylenotlenowego z siarczku dwutlenku etylowego.Przyklad 1.Szesc czesci na wage bezwodnika kwasu octowego nagrzewamy, z odply¬ wem wstecznym, do 120°, dodajac don zwolna, kroplami piec czesci wagowych siarczku dwutlenku dwuetylowego. Po ukonczeniu reakcji destylujemy w próz¬ ni, przyczem przechodzi okolo 5 cze¬ sci wagowych nowego estru dwuetylo¬ wego przy 142—150° i 12 mm cisnienia.Otrzymany w ten sposób klarowny plyn, który, w przeciwienstwie do produktu wyjsciowego, z woda sie nie miesza, daje nastepujace wyniki analizy; Znaleziono S—15,73% C-46,61% H— 6,99% Obliczono dla C8H1404S S—15,5% C—46,6% H-6,79% Ester acetylowy mozna wytwarzac równiez przez stosowanie octu lodowa¬ tego lub rozcienczonego kwasu octo-wego, podobnie, jak to podano w przy¬ kladzie 2-im dla kwasu mrówkowego.Przyklad 2.Jedna czesc na wage siarczku dwu¬ tlenku etylowego nagrzewamy przez trzy godziny z 5 czesciami wagowemi 90% kwasu mrówkowego, poczem odpedza sie zbyteczny kwas mrówkowy. Pozo¬ stajacy w wodzie nierozpuszczalny eter diformylowy odpedza sie w ilosci mniej wiecej równoznacznej przy 7 mm i 130—137°.Przez podstawienie w przykladzie 1, zamiast bezwodnika kwasu octowego, innych bezwodników, np. kwasu benzo¬ esowego lub ftalowego, powstaja rów¬ niez odpowiednie estry.Przyklad 3. 244 czesci tiodwuglikolu nagrzewamy z 2000 czesciami kwasu siarczanego (podwójnej normalnosci) w prózni do zupelnego odpedzenia wody. Pozostaje gumowaty osad, latwo dajacy sie zetrzec na biala bezksztaltna mase znacznej objetosci i elastyczna. Otrzymany w ten sposób ester kwasu siarczanego mozna traktowac woda lub alkoholem. Po dluz- szem odstaniu z woda, otrzymany ester kwasu siarczanego przechodzi w postac galaretowata. Mozna zen otrzymac od¬ powiednie sole estrów kwasu siarcza¬ nego thiohydrynowego, przez zmiesza¬ nie, np. z weglanami lub wodorotlen¬ kami.Przyklad 4. 244 czesci tiodwuglikolu nagrzewa¬ my z 3000 czesci pasty np. 5% wodoro¬ tlenku glinowego w prózni, az do zu¬ pelnego odpedzenia wody. Pozostaly galaretowaty osad mozna zastosowac do wskazanych celów, badz to bezpo¬ srednio, badz w rozcienczeniu, np. z thio- dwuglikolem. PLIt has been found that diethyl dioxide sulphide can be obtained by heating it with organic or inorganic acids. Acids are also understood to mean those hydroxide-containing compounds which, as is the case with aluminum hydroxide, for example, are very weak and have a dual character. Especially when using mineral acids, care should be taken to select conditions that are so mild that the formation of diethylene oxide sulphide from ethyl dioxide sulphide, which may occur, does not occur. Example 1 We heat up some parts of the weight of acetic anhydride with drainage. retrograde, up to 120 °, adding the don slowly, dropwise five parts by weight of diethyl dioxide sulfide. After the reaction is complete, we distill in a vacuum, with about 5 parts by weight of the new diethyl ester passing at 142-150 ° and 12 mm pressure. The resulting clear liquid, which, unlike the starting product, turns into water. does not mix, gives the following analysis results; Found S — 15.73% C — 46.61% H — 6.99% Calculated for C8H1404S S — 15.5% C — 46.6% H — 6.79% Acetyl ester can also be produced by using ice vinegar of this or diluted acetic acid, similarly to the example given in example 2 for formic acid. Example 2: One part by weight of the ethyl oxide sulphide is heated for three hours with 5 parts by weight of 90% formic acid, then unnecessary formic acid is chased away. The water-insoluble diphormyl ether is stripped off approximately equivalent to 7 mm and 130-137 °. By substituting in example 1, for acetic acid anhydride, other anhydrides, e.g. benzoic acid or phthalic acid, are formed. not suitable esters. Example 3. We heat 244 parts of thiodiglycol with 2000 parts of sulfuric acid (double normal) in a vacuum until the water is completely drained. A rubbery deposit remains, easily rubbed off into a white, shapeless mass of considerable volume and elastic. The sulfuric ester obtained in this way can be treated with water or alcohol. After a longer standing with water, the obtained sulfuric acid ester turns into a gelatinous form. The corresponding salts of the sulfated esters of thiohydrinic acid can be obtained by mixing e.g. with carbonates or hydroxides. Example 4 244 parts of thiodiglycol are heated with 3000 parts of paste, e.g. vacuum until the water is completely drained. The remaining gelatinous precipitate can be used for the indicated purposes, either directly or in dilution, eg with thio-diglycol. PL
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL443B1 true PL443B1 (en) | 1924-08-30 |
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