SU235009A1 - METHOD OF OBTAINING ALMOND ACID - Google Patents
METHOD OF OBTAINING ALMOND ACIDInfo
- Publication number
- SU235009A1 SU235009A1 SU1212016A SU1212016A SU235009A1 SU 235009 A1 SU235009 A1 SU 235009A1 SU 1212016 A SU1212016 A SU 1212016A SU 1212016 A SU1212016 A SU 1212016A SU 235009 A1 SU235009 A1 SU 235009A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- obtaining
- yield
- almond acid
- almond
- Prior art date
Links
- IWYDHOAUDWTVEP-UHFFFAOYSA-N Mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 title description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- -1 phenyl halide acetic acids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- ABFRBTDJEKZSRM-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanol Chemical compound ClC(Cl)(Cl)C(O)C1=CC=CC=C1 ABFRBTDJEKZSRM-UHFFFAOYSA-N 0.000 description 1
- 241000191291 Abies alba Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 102000037197 Anion exchangers Human genes 0.000 description 1
- 108091006437 Anion exchangers Proteins 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000003068 static Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Способ относитс к методам получени «./-миндальной кислоты, котора южет служить нолупродуктом дл синтеза гербицидны.х препаратов, ьаирпмер фенилгалоидуксусных кислот, а также сравпительио малотокспчных фосфорорганических инсектицидов тигга «циднал .The method relates to the methods of obtaining "./- alindic acid, which will serve as a product for the synthesis of herbicidal preparations, pigment phenyl halide acetic acids, and sravpitelio of low-toxic organophosphorus insecticide tigg" cydnal.
Известно получение миндальной кислоты при гидролизе фенилтрихлорметплкарбинола lOVo-HbiM раствором едкого кали; прп этом получаетс фенилхлоруксусна кислота (выход 26,4%), миндальна кислота с примесью фепилхлоруксусной (выход 25;Vo), а также ироисходит разложение фенилтрихлорметилкарбинола с образованием бензальдегида (выход 25,8;Ус). Таким образом миндальна кислота получаетс нз фенилтрихлорметилкарбппола с довольно низким выходом, загр зиеппа продуктами реакции, что не позвол ет примеи ть гидролиз карбинола дл получепп миндальной кислоты в промышленном масшгабе. Дл увеличени выхода и повышенп чистоты продукта предложено проводить иропесс в водном диоксане иа анионите АВ-17 (ОНформа ).It is known to obtain mandelic acid by hydrolysis of phenyltrichloromethylphenol carbinol with lOVo-HbiM potassium hydroxide solution; This produces phenyl chloroacetic acid (yield 26.4%), almond acid mixed with phenyl chloroacetic acid (yield 25; Vo) and decomposes phenyltrichloromethylcarbinol to form benzaldehyde (yield 25.8; C). Thus, almond acid is obtained from phenyltrichloromethylcarbppol in a rather low yield, contamination is caused by reaction products, which prevents the use of carbinol hydrolysis to obtain almond acid in an industrial scale. In order to increase the yield and increase the purity of the product, it was proposed to conduct an iropess in aqueous dioxane and anion exchanger AB-17 (ONform).
Преи.мушество сиособа состоит в , что и елочной агент можно регенерировать и исиользовать повторно.The advantage of this method is that the Christmas tree agent can be regenerated and reused.
АВ-17 (статическа AB-17 (static
ооменна oomenna
емкостьcapacity
75%-ного водного ди;о , 2.4 мг 5лв/г) и 300 лг.г75% aqueous di; o, 2.4 mg 5Lv / g) and 300 lg.g
оксаиа кип т т при перемешиванип 6 час апионит отфильтровывают, промывают Ю-/оиым раствором едкого натра и водой, от объединенного водподиоксанового раствора отгон ют диоксан, остаток экстрагируют эфиром (2X100 мл}, подкисл ют 10%-ной серной кислотой , экстрагируют эфиром в жидкостном экстракторе в течение 6 час; экстракт сушат сульфатом магни , упаривают, получают d,iмпндальную кислоту- 10,4 г (); т. пл. 113-115°С (неочищенна ); т. ил. 118°С (после кристаллизации из бензола).oxia is boiled under stirring for 6 hours; the apionite is filtered off, washed with sodium hydroxide solution and sodium hydroxide, dioxane is distilled off from the combined water-dioxane solution, the residue is extracted with ether (2X100 ml), acidified with 10% sulfuric acid, extracted with ether liquid extractor for 6 hours; the extract is dried with magnesium sulfate, evaporated to give d, impedic acid — 10.4 g (); mp. 113-115 ° C (crude); soot. 118 ° C (after crystallization from benzene).
П р и м е р 2. Смесь 22,55 г карбинола, 170 г анионпта АВ-17 и 200 .мл 75%-ного д;1оксана кип т т при перемешивании б час, фильтруют, ионит промывают водой. Фильтрат и промывные воды подпделачивают Ю/с-ным раствором едкого натра, диоксан отгон ют, остаток экстрагируют эфиром (2X100 -нл), подкисл ют 10%-ной серной кислотой, эфиром в жидкостном экстракторе пзвлекают .миндальную кислоту . Выход 6,72 г (44,2;0/о).PRI mme R 2. A mixture of 22.55 g of carbinol, 170 g of AB-17 anionpta and 200 ml of 75% d; 1oxane is boiled with stirring for an hour, filtered, the ion exchanger is washed with water. The filtrate and the washings are triturated with 10 N sodium hydroxide solution, the dioxane is distilled off, the residue is extracted with ether (2X100 -nl), acidified with 10% sulfuric acid, and an imminent acid is extracted with ether. Yield 6.72 g (44.2; 0 / o).
Предмет изобретени 3 мами, отличающийс тем, что, с целью увеличени выхода и повышени чистоты целевого 4 продукта, процесс провод т в водном дноксапе па апионите, например АВ-17 (ОН-форма).The subject matter of the invention is 3 mami, characterized in that, in order to increase the yield and increase the purity of the target 4 product, the process is carried out in an aqueous dixone of the apionite, for example AB-17 (OH-form).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU235009A1 true SU235009A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713485A (en) * | 1984-11-29 | 1987-12-15 | SANOFI and Industria Chimica Prodotti FRANCIS S.p.A. | Process for preparing α-hydroxy-alkanoic acids and compounds obtained by this process |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713485A (en) * | 1984-11-29 | 1987-12-15 | SANOFI and Industria Chimica Prodotti FRANCIS S.p.A. | Process for preparing α-hydroxy-alkanoic acids and compounds obtained by this process |
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