SU191577A1 - METHOD OF OBTAINING PHYLENE ESTERS OF PHENYLACETIC ACID - Google Patents
METHOD OF OBTAINING PHYLENE ESTERS OF PHENYLACETIC ACIDInfo
- Publication number
- SU191577A1 SU191577A1 SU1054602A SU1054602A SU191577A1 SU 191577 A1 SU191577 A1 SU 191577A1 SU 1054602 A SU1054602 A SU 1054602A SU 1054602 A SU1054602 A SU 1054602A SU 191577 A1 SU191577 A1 SU 191577A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenylacetic acid
- esters
- phylene
- obtaining
- acetic acid
- Prior art date
Links
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 title claims description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 7
- 229960003424 phenylacetic acid Drugs 0.000 title claims description 7
- 239000003279 phenylacetic acid Substances 0.000 title claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- USVNNHYNCCJCCP-UHFFFAOYSA-N phenyl 2-phenylacetate Chemical class C=1C=CC=CC=1OC(=O)CC1=CC=CC=C1 USVNNHYNCCJCCP-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 230000036826 Excretion Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области получени фениловых эфиров фенилуксусной кислоты , которые могут найти применение в парфюмерной промышленности.The invention relates to the field of phenyl esters of phenylacetic acid, which can be used in the perfume industry.
Известно получение фениловых эфиров фенилуксусной кислоты путем нагревани алкилфенолов с фенилуксусной кислотой в присутствии 2о/о катализатора д-толуолсульфокислоты в течение 8-10 час. По окончании реакции из массы под вакуумом отгон ют воду, оставшуюс массу раствор ют в бензоле и промывают последовательно водой, раствором пделочи и снова водой до нейтральной реакции . Затем бензольный раствор сушат над хлористым кальцием и отгон ют бензол. Выход сырого продукта от теоретического количества. Недостаток способа состоит в продолжительном по времени процессе и невысоком выходе целевого продукта.Phenylacetic acid phenyl esters are known to be prepared by heating alkylphenols with phenylacetic acid in the presence of a 2 ° / o d-toluene sulfonic acid catalyst for 8-10 hours. At the end of the reaction, water is distilled off from the mass under vacuum, the remaining mass is dissolved in benzene and washed successively with water, a baking solution and again with water until neutral. The benzene solution is then dried over calcium chloride and benzene is distilled off. The yield of raw product from the theoretical amount. The disadvantage of this method is a time-consuming process and a low yield of the target product.
Предлагаемый способ заключаетс во взаимодействии соответствуюшего алкилфенола и фенилуксусной кислоты в присутствии уксусного ангидрида с последуюшим нагреванием смеси до температуры кипени в услови х куба ректификационной колонки с последуюш .ей отгонкой выделившейс в результате реакции этерификации уксусной кислоты. Реакцию ведут без катализатора.The proposed method consists in the interaction of the corresponding alkylphenol and phenylacetic acid in the presence of acetic anhydride, followed by heating the mixture to the boiling point under the conditions of the bottom of the distillation column, followed by distilling off the acetic acid produced by esterification. The reaction is carried out without a catalyst.
насадочной ректификационной колонки высотой 400 см загружают эквимолекул рные количества соответствуюш.его алкилфенола, уксусного агидрида и фенилуксусной кислоты сa 400 cm high packed distillation column was charged with equimolecular amounts of its corresponding alkylphenol, acetic acid and phenylacetic acid with
70/о-ным избытком от теоретического. Смесь нагревают до кипени и по достижении температуры паров в дефлегматоре колонки 118°С отбирают выдел юш.уюс в результате этерификации уксусную кислоту. Окончание70 / o-nym excess from theoretical. The mixture is heated to boiling and, when the vapor temperature in the column reflux condenser reaches 118 ° C, an excretion of acetic acid is selected by etherification. Ending
процесса контролируют прекраш.ением отгонки уксусной кислоты, а также количеством отобранной уксусной кислоты.the process is controlled by the termination of the distillation of acetic acid, as well as the amount of acetic acid selected.
1313
2020
2525
зола или толуола, последовательно промывают водой, 50/о-ным раствором щелочи и снова водой до нейтральной реакции промывных вод. Далее промытый раствор разгон ют. При атмосферном давлении отгон ют растворитель , а затем под вакуумо.м выдел ют целевой продукт.ash or toluene is successively washed with water, 50 / alkaline solution of alkali and again with water until neutral wash water. Next, the washed solution is dispersed. At atmospheric pressure, the solvent is distilled off, and then the desired product is isolated under vacuum.
Результаты отдельных опытов синтеза сложных фениловых эфиров фенилуксусной кислоты приведены в таблице.The results of individual experiments on the synthesis of phenyl esters of phenylacetic acid are given in the table.
4 Предмет изобретени 4 Subject of the invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU191577A1 true SU191577A1 (en) |
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