CS273089B1 - Method of l(+) tartaric acid's diethyl ester production - Google Patents
Method of l(+) tartaric acid's diethyl ester production Download PDFInfo
- Publication number
- CS273089B1 CS273089B1 CS772788A CS772788A CS273089B1 CS 273089 B1 CS273089 B1 CS 273089B1 CS 772788 A CS772788 A CS 772788A CS 772788 A CS772788 A CS 772788A CS 273089 B1 CS273089 B1 CS 273089B1
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- CS
- Czechoslovakia
- Prior art keywords
- tartaric acid
- esterification
- deta
- diethyl ester
- solvent
- Prior art date
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 title abstract 3
- 235000011002 L(+)-tartaric acid Nutrition 0.000 title abstract 3
- 239000001358 L(+)-tartaric acid Substances 0.000 title abstract 3
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000032050 esterification Effects 0.000 claims abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 9
- 238000000199 molecular distillation Methods 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 235000002906 tartaric acid Nutrition 0.000 claims description 9
- 239000011975 tartaric acid Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 4
- YSAVZVORKRDODB-UHFFFAOYSA-N Diethyl tartrate Chemical compound CCOC(=O)C(O)C(O)C(=O)OCC YSAVZVORKRDODB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims 1
- 239000010409 thin film Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 150000002500 ions Chemical class 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 229910006069 SO3H Inorganic materials 0.000 abstract description 2
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000004753 textile Substances 0.000 abstract description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 239000007809 chemical reaction catalyst Substances 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000003899 tartaric acid esters Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Vynález sa týká sposobu výroby dietylesteru kyseliny L/+/ vinnéj pre potravinářské účely esterifikáciou kyseliny hl+t vínnej s etanolom a následného čistenia produktu.The present invention relates to a process for the production of diethyl L / + / tartaric acid ester for food use by esterification of hl + tartaric acid with ethanol and subsequent purification of the product.
Diestylester kyseliny vínnej sa najčastejšie vyrába azeotropickou esterifikáciou kyseliny vínnej s etanolom za použitia chloroformu alebo tetraphlórmetánu ako azeotropického činidla. Reakcia sa urýchluje katalyzátorom vo formě koncentrovanéj kyseliny sírovej alebo katexom v H+ cykle (Kolektiv! Organická synthesa, Academia Praha, 1971). Zbytokpo esterifikácii, po odstránení ionexu a rozpúštadla, sa destiluje.Diestyl tartaric ester is most commonly produced by azeotropic esterification of tartaric acid with ethanol using chloroform or tetraphloromethane as an azeotropic agent. The reaction is accelerated by a catalyst in the form of concentrated sulfuric acid or by cation exchange in an H + cycle (Kolektiv! Organic Synthesis, Academia Praha, 1971). The residue after esterification, after removal of the ion exchanger and solvent, is distilled.
Doteraz známe sposoby umožňovali získavanie tejto látky len s malou výtažnostou a nedostatočnou čistotou. Použitím vákuovej destilácie dochádzalo k chemickým změnám dietylesteru kyseliny L/+/ vínnej v dósledku jeho termolability.Hitherto known processes have allowed to obtain this substance with only a low yield and poor purity. The use of vacuum distillation resulted in chemical changes in diethyl ester of L / + / tartaric acid due to its thermolability.
Podlá vynálezu možno dietylester kyseliny L/+/ vínnej vyrotít azeotropickou esterifikáciou kyseliny L/+/ vínnej s absolutným etanolom a chloroformom ako činidlom vytvárajúcim azeotropídcú zmes. Ako katalyzátor možno použit silné kyslý katex v H+ formě typu kopolyméru styrénu s divinylbenzénom s -SOg H funkčnými skupinami zrnenia 0,3 až 1,2.mm. Produkt po esterifikácii, po odfiltrovaní ionexu a_oddestilovaní rozpúštadla sa čistí molekulovou destiláciou pri tlaku 9 Pa a teplote 100 ’c. Táto operácia umožňuje zníŽením tlaku znížit pracovnú teplotu a odpařováním látky v tenkom stieranom filme podstatné skrátiť čas posobenia zvýšenej teploty. Prietok destilovanej vzorky třeba přitom upravit tak, aby čas posobenia zvýšenej teploty bol minimálny.According to the invention, the diethyl ester of L (tartaric acid) can be etched by azeotropic esterification of L (tartaric acid) with absolute ethanol and chloroform as the azeotropic mixture forming agent. A strong acid cation exchanger in the H + form of a styrene-divinylbenzene-type copolymer with -SOg H grain size groups of 0.3 to 1.2 mm can be used as the catalyst. The product after esterification, filtration of the ion exchanger and distillation of the solvent is purified by molecular distillation at a pressure of 9 Pa and a temperature of 100 ° C. This operation makes it possible to reduce the working temperature by decreasing the pressure and by vaporizing the substance in a thin wiped film to substantially reduce the residence time of the elevated temperature. The flow rate of the distilled sample must be adjusted so that the time of elevated temperature is kept to a minimum.
Uvedeným sposobom možme získat dietylester kyseliny L/+/ vínnej požadovaných fyzikálnochemických parametrov, s minimálnym obsahom nežiadúcich příměsí.In this way, it is possible to obtain diethyl ester of L / + / tartaric acid of the desired physicochemical parameters, with a minimum content of undesirable additives.
Příklad 1:Example 1:
Zmes 1 mol kyseliny L/+/ vínnej a 3,5 mol absolutného etanolu bola esterifikovaná pri teplote varu zmesi 24 hodin s 10 g silné kyslého katexu typu kopolyméru styrénu s divinylbenzénom s -SOjH funkčnými skupinami v H+ formě, zrnenia 0,5 až 1,2 mm, s kapacitou 3,65 mval/g suchého ionexu a 200 ml chloroformu. V priebehu reakcie sa odoberala vzniknutá voda. Po odfiltrovaní ionexu a oddestilovaní rozpúštadla bol získaný produkt s obsahom 94,44% dietylesteru kyseliny L/+/ vínnej, ktorý bol čištěný molekulovou destiláciou za nasledovných podmienok;A mixture of 1 mole of L / + / tartaric acid and 3.5 mole of absolute ethanol was esterified at boiling point for 24 hours with 10 g of a strong acidic cation exchanger of the styrene-divinylbenzene type with -SO3H functional groups in H + form. 1.2 mm, with a capacity of 3.65 mval / g dry ion exchange resin and 200 ml of chloroform. The resulting water was collected during the reaction. Filtration of the ion exchanger and distillation of the solvent yielded a product containing 94.44% of diethyl L / + / tartaric acid ester, which was purified by molecular distillation under the following conditions;
odparná plocha: 75 cm2 nástrek vzorky: 80 ml/h praoovná teplota: 100 'c tlak v odparke: 9 Paevaporation area: 75 cm 2 sample injection: 80 ml / h Roasting temperature: 100 'c Evaporator pressure: 9 Pa
Získaný produkt obsahoval 99,88% dietýlesteru kyseliny L/+/ vínnej. Jeho fyzikálnoohemické parametre boli následovně: optická otáčavost /«0/ = 8,372’ index lomu n^ = 1,445 20 špecifická hustota = 1,207 kg/m3 The product obtained contained 99.88% L / + / tartaric acid diethyl ester. Its physico-chemical parameters were as follows: optical rotation (00) = 8.372 'refractive index n ^ = 1.4545 20 specific density = 1.207 kg / m 3
Příklad 2:Example 2:
Zmes 1 mol kyseliny L/+/ vínnej a 3,5 mol absolutného etanolu bola esterifikovaná pri teplote varu zmesi 18 hodin s 10 g silné kyslého katexu typu kopolyméru styrénu s divinylbenzénom s -SOjH funkčnými skupinami v H+ formě, zrnenia 0,3 až 0,8 mm, kapacity 3,34 mval/g suchého ionexu a 200 ml chloroformu. V priebehu reakcie sa odoberala vzniknutá voda. Po odfiltrovaní ionexu a oddestilovaní rozpúštadla bol získaný produkt s obsahom 99,24 % dietýlesteru kyseliny L/+/ vínnej, ktorý bol dalej čištěný molekulovou destiláciou za podmienok podlá příkladu 1. Získaný produkt obsahoval 99,85 % dietýlesteru kyseliny L/+/ vínnej. Jeho fyzikálnoohemioké parametre boli následovně:A mixture of 1 mole of L / + / tartaric acid and 3.5 mole of absolute ethanol was esterified at boiling point for 18 hours with 10 g of a strong acidic cation exchange resin of styrene-divinylbenzene type with -SO2H functional groups in H + form. 0.8 mm, capacities of 3.34 mval / g dry ion exchanger and 200 ml of chloroform. The resulting water was collected during the reaction. Filtration of the ion exchanger and distillation of the solvent gave a product containing 99.24% diethyl L / + / tartaric acid ester, which was further purified by molecular distillation under the conditions of Example 1. The product obtained contained 99.85% diethyl L / + / tartaric acid ester. Its physico-chemical parameters were as follows:
CS 273 089 Bl %CS 273 089 Bl
a?and?
Ω optická otáčivost/tf/ = 8,050 20 index lomu nD =1,445 20Ická optical rotation (tf) = 8,050 20 refractive index n D = 1,445 20
Specifická hustota = 1,205Specific Density = 1.205
Dietylester kyseliny L/+/ vínnej uvedenej čistoty možno využit v potravinárstve ako aromatická látku a nosné rozpúštadlo (FAO Food and Nutrition Paper. Specifications for identity and purity, 19. Rome, 1981.), alebo v kozmetike ako účinná dezodoračnú látku (patenty NSR 29 18 362 a 28 36 759), ale aj v iných oblastiach národného hospodárstva (organická technologie, textilný priemysel).The L / + / tartaric acid diethyl ester of the indicated purity can be used in the food industry as a flavoring and carrier solvent (FAO Food and Nutrition Paper. Specifications for identity and purity, 19 Rome, 1981.) or in cosmetics as an effective deodorant 29 18 362 and 28 36 759), but also in other areas of the national economy (organic technology, textile industry).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS772788A CS273089B1 (en) | 1988-11-24 | 1988-11-24 | Method of l(+) tartaric acid's diethyl ester production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS772788A CS273089B1 (en) | 1988-11-24 | 1988-11-24 | Method of l(+) tartaric acid's diethyl ester production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS772788A1 CS772788A1 (en) | 1990-07-12 |
| CS273089B1 true CS273089B1 (en) | 1991-03-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS772788A CS273089B1 (en) | 1988-11-24 | 1988-11-24 | Method of l(+) tartaric acid's diethyl ester production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS273089B1 (en) |
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1988
- 1988-11-24 CS CS772788A patent/CS273089B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS772788A1 (en) | 1990-07-12 |
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