SU166036A1 - METHOD OF OBTAINING N-ALKYL-R-ANISIDINES - Google Patents
METHOD OF OBTAINING N-ALKYL-R-ANISIDINESInfo
- Publication number
- SU166036A1 SU166036A1 SU805087A SU805087A SU166036A1 SU 166036 A1 SU166036 A1 SU 166036A1 SU 805087 A SU805087 A SU 805087A SU 805087 A SU805087 A SU 805087A SU 166036 A1 SU166036 A1 SU 166036A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- anisidines
- obtaining
- temperature
- catalyst
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241001676573 Minium Species 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical class [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- -1 cyclic alcohols Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002829 reduced Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Известен способ получени N-алкил-р-апизидинов восстановительным алкилировапием р-анизидина при температуре выше 100° С.A known method for the preparation of N-alkyl-p-apizidines by reductive alipylation of p-anisidine at temperatures above 100 ° C.
С целью упрощени технологической схемы предложен способ получепи N-алкил-р-анизидинов алкилированием р-анизидина первичными , вторичными и циклическими спиртами, а также (3-нафтолом. Процесс ведут при атмосферном давлении и температуре 100- 220° С на никеле Репе .. In order to simplify the technological scheme, a method is proposed for obtaining N-alkyl-p-anisidines by alkylation of p-anisidine with primary, secondary and cyclic alcohols, as well as (3-naphtol. The process is carried out at atmospheric pressure and a temperature of 100-220 ° C on Nickel Reppe ..
Полученные продукты используютс в качестве противостарителей дл резипы и других полимерных материалов.The resulting products are used as antioxidants for resips and other polymeric materials.
Пример 1. В трехгорлую колбу емкостью 250 мл, снабжеппую мешалкой, термометром, обратным холодильником и насадкой Дина и Старка дл отгона реакционной воды, загружают 20 г (0,162 г. моль} р-апизидина, 65,08 г (0,649 г. моль) циклогексапола и 4 г катализатора Ni-Репе . (Катализатор Ni- Рене получают из цикельалЮ Миниевого сплава вышслачиванием 25%-ным раствором NaOn при 50-60° С в течение 2 час). Катализатор перед употреблением промывают циклогексанолом . Включают мешалку и реакционную массу подогревают на масл ной бане. При температуре реакционна масса начинает кипеть и при 146° С начинает отгон тьс реакционна вода с небольшой примесью циклогексанола, которын сооираетс над водой.Example 1. A 250 ml three-neck flask supplied with a stirrer, a thermometer, a reflux condenser and a Dean and Stark nozzle for distillation of the reaction water was charged with 20 g (0.162 g mol} p-apisidine, 65.08 g (0.649 g mol) cyclohexapol and 4 g of Ni-Repe catalyst. (Ni-Rene catalyst is obtained from Cyclogel Minium alloy by extracting with 25% NaOn solution at 50-60 ° C for 2 hours.) The catalyst is washed with cyclohexanol before use. The stirrer is turned on and the reaction mass is heated in an oil bath. At a temperature the reaction mass starts At 146 ° C, the boiling water begins to be distilled off with a small admixture of cyclohexanol, which is placed above the water.
Реакционную массу выдерживают при температуре 146-164°С и интенсивно работающей мешалке в течение 2,5 час, затем при температуре 60 С отфильтровывают от катализатора . Катализатор промывают 10 мл циклогексапола . Затем реакционную массу разгон ют под вакуумом. Вначале отгон етс избыточный циклогексанол при температуре 52-55° С и давлении 10 мм рт. ст. Отогнанный циклогексанол носле разгонки при атмосферном давлении может употребл тьс в последующих синтезах.The reaction mass is maintained at a temperature of 146-164 ° C and vigorously working stirrer for 2.5 hours, then at a temperature of 60 ° C is filtered from the catalyst. The catalyst is washed with 10 ml of cyclohexapol. Then the reaction mass is distilled under vacuum. Initially, excess cyclohexanol is distilled off at a temperature of 52-55 ° C and a pressure of 10 mm Hg. Art. Distilled cyclohexanol during distillation at atmospheric pressure can be used in subsequent syntheses.
Конечный продукт N-циклогексил-р-апизидин отгоп етс при температуре 136-141° С и давлении 2 мм рт. ст. в виде масл нистой бесцветпо жидкости, кристаллизующейс в приемниках , т. нл. 35,4-36,9° С.The final product, N-cyclohexyl-p-apizidine, is recovered at a temperature of 136-141 ° C and a pressure of 2 mm Hg. Art. in the form of an oily, colorless liquid that crystallizes in the receivers, i.e. 35.4-36.9 ° C.
Выделено 30,62 г N-циклогексил-р-анизидипа , что составл ет выход 91,5% от теории, счита па р-анизидин.30.62 g of N-cyclohexyl-p-anisidipa were isolated, which constitutes a yield of 91.5% of theory, considered as p-anisidine.
Пайдено: в о/о: С 76,39; ,22; N 6,85. CisHiaON.Paideno: in c / o: C 76.39; , 22; N 6.85. CisHiaON.
Вычислено, в С 76,03; ,33; N 6.83.Calculated in C 76.03; , 33; N 6.83.
Пример 2. В трехгорлую колбу емкостью 250 мл, снабженную мешалкой, термометром, обратным холодильником и насадкой Дина и Старка дл отгона реакционной воды, загружают 40 г (0,324 г. моль) р-анизидина,Example 2. A 250 ml three-neck flask equipped with a stirrer, a thermometer, a reflux condenser and a Dean and Stark nozzle for distillation of the reaction water was charged with 40 g (0.324 g) mol of p-anisidine,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU166036A1 true SU166036A1 (en) |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015773A (en) * | 1988-08-18 | 1991-05-14 | Bp Chemicals Limited | Reductive amination of hydroxy-containing compounds |
| RU2472774C1 (en) * | 2011-09-28 | 2013-01-20 | Закрытое Акционерное Общество "Ифохим" | Method for selective production of n-methyl-para-anisidine |
| RU2631510C1 (en) * | 2016-06-21 | 2017-09-25 | Публичное акционерное общество "Химпром" | Method for producing n-methyl-para-anisidine |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015773A (en) * | 1988-08-18 | 1991-05-14 | Bp Chemicals Limited | Reductive amination of hydroxy-containing compounds |
| RU2472774C1 (en) * | 2011-09-28 | 2013-01-20 | Закрытое Акционерное Общество "Ифохим" | Method for selective production of n-methyl-para-anisidine |
| WO2013048279A1 (en) | 2011-09-28 | 2013-04-04 | Закрытое Акционерное Общество "Ифохим" | Method for the selective production of n-methyl-para-anisidine |
| US9856205B2 (en) | 2011-09-28 | 2018-01-02 | Ifotop Limited Liability Company | Method for the selective production of N-methyl-para-anisidine |
| RU2631510C1 (en) * | 2016-06-21 | 2017-09-25 | Публичное акционерное общество "Химпром" | Method for producing n-methyl-para-anisidine |
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