SU979322A1 - Process for producing alpha-methyl-p-tert-butylhydrocinnamic aldehyde - Google Patents
Process for producing alpha-methyl-p-tert-butylhydrocinnamic aldehyde Download PDFInfo
- Publication number
- SU979322A1 SU979322A1 SU813314540A SU3314540A SU979322A1 SU 979322 A1 SU979322 A1 SU 979322A1 SU 813314540 A SU813314540 A SU 813314540A SU 3314540 A SU3314540 A SU 3314540A SU 979322 A1 SU979322 A1 SU 979322A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- tert
- aldehyde
- hydrogen
- producing alpha
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- -1 -tert-butyl hydroxyl aldehyde Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Изобретение относитс к усовершенствованному способу получени oZ -метил- п-трет-бутилгидрокоричного альдегида, который используют в пар4 омерии в качестве ценного душистого вещества.This invention relates to an improved process for the preparation of oZ -methyl-p-tert-butyl hydroxyl aldehyde, which is used in parmery as a valuable fragrance.
Известен способ получени of-метил -h-трет-бутилгидрокрричного альдегида гидрированием ot-метил-п-трет-бутилкоричного альдегида эквимол рным количеством водорода в присутствии катализатора - паллади на угле при 75-80С и 5%-ного водного раствора углекислого натри tl3.A known method of producing of methyl-h-tert-butyl hydroxymerdehyde by hydrogenating ot-methyl-p-tert-butylcinnarmaldehyde with an equimolar amount of hydrogen in the presence of a catalyst, palladium on carbon at 75-80 ° C and a 5% aqueous solution of sodium carbonate tl3.
Недостатком данного способа вл етс использование дорогого и дефицитного палладиевЬго катализатора.The disadvantage of this method is the use of an expensive and scarce palladium catalyst.
Наиболее близким техническим рещением данной задачи вл етс способ получени о1-метил-п-трет-бутилгйдрокоричного альдегида гидрированием ot-метил-п-трет-бутилкоричного альдегида 1,45-кратным мольным избытком водорода в присутствии катализатора - никел Рене и водного раствора К 2 СОа.при , селективность процесса 56,5% 23.The closest technical solution to this problem is the method of obtaining o1-methyl-p-tert-butyl hydroquoric aldehyde by hydrogenating ot-methyl-p-ter-butylcinnamic aldehyde with 1.45-fold molar excess of hydrogen in the presence of a catalyst — Rene nickel and K 2 aqueous solution SOA.pri, process selectivity 56.5% 23.
Недостатком данного способа вл етс низкое содержание целевого продукта.The disadvantage of this method is the low content of the target product.
Целью изобретени вл етс повышение селективности процесса.The aim of the invention is to increase the selectivity of the process.
Поставленна цель достигаетс предложенным способом получени Ы-метил-п-трет-бутилгидрокоричного альдегида гидрированием ot-метил-п-трет-бутилкоричного альдегида 1,2 1,25-кратным мольным избытком водорода в водном изопропилспиртовом ра10 створе углекислого кали при 95-120 С в присутствии никельсодержащего катализатора Ni/Cr Oj .The goal is achieved by the proposed method for the preparation of N-methyl-p-tert-butyl hydroquoric aldehyde by hydrogenation of ot-methyl-p-ter-butylcinnarmaldehyde with 1.2 1.2-fold molar excess of hydrogen in an aqueous isopropyl alcohol solution of potassium carbonate at 95-120 ° C in the presence of a nickel-containing catalyst Ni / Cr Oj.
Особенностью предложенного способа вл етс то, что в качестве никель15 содержащего кат ализатора используют Ni/СгаОз, в качестве водосодержащего раствора углекислого кали - водный изопропиловый спирт и процесс ведут при 95-120 С и кратном мольном из20 бытке водорода, равном 1,2-1,25.The peculiarity of the proposed method is that Ni / CgaOz is used as the nickel15 containing catalyst, and the aqueous isopropyl alcohol is used as the aqueous solution of potassium carbonate and the process is carried out at 95–120 ° C and a 1.2–1 fold hydrogen mole rate. 25
Выбор кратного мольного избытка водорода обусловлен следующими факторами; ведение процесса при кратности по водороду менее 1,2 приводит The choice of a multiple molar excess of hydrogen is due to the following factors; conducting the process at a hydrogen multiplicity of less than 1.2 leads
25 к образованию продукта гидрировани -, в котором содержитс более jif.. нежелательной примеси исходного ot-метил-п-трет-бутйлкоричного гшьдегйда, а при кратности более 1,25 продукт гидрировани содержит более 27%25 to the formation of the hydrogenation product -, which contains more than jif. Undesirable impurities of the original ot-methyl-p-tert-butylcinnamic acid, and with a multiplicity of more than 1.25, the hydrogenation product contains more than 27%
30thirty
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU813314540A SU979322A1 (en) | 1981-07-10 | 1981-07-10 | Process for producing alpha-methyl-p-tert-butylhydrocinnamic aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU813314540A SU979322A1 (en) | 1981-07-10 | 1981-07-10 | Process for producing alpha-methyl-p-tert-butylhydrocinnamic aldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU979322A1 true SU979322A1 (en) | 1982-12-07 |
Family
ID=20968070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813314540A SU979322A1 (en) | 1981-07-10 | 1981-07-10 | Process for producing alpha-methyl-p-tert-butylhydrocinnamic aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU979322A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2662835C2 (en) * | 2013-05-08 | 2018-07-31 | Живодан Са | 3-(4-isobutyl-2-methylphenyl)propanal as perfume ingredient |
| US10138195B2 (en) | 2014-11-10 | 2018-11-27 | Givaudan, S.A. | Organic compounds |
| RU2697708C2 (en) * | 2014-11-10 | 2019-08-19 | Живодан Са | Compounds based on phenyl substituted with aldehyde fragments, and their use in perfumes |
| US10457891B2 (en) | 2013-05-08 | 2019-10-29 | Givaudan S.A. | Organic compounds |
-
1981
- 1981-07-10 SU SU813314540A patent/SU979322A1/en active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2662835C2 (en) * | 2013-05-08 | 2018-07-31 | Живодан Са | 3-(4-isobutyl-2-methylphenyl)propanal as perfume ingredient |
| US10457891B2 (en) | 2013-05-08 | 2019-10-29 | Givaudan S.A. | Organic compounds |
| US10138195B2 (en) | 2014-11-10 | 2018-11-27 | Givaudan, S.A. | Organic compounds |
| RU2697708C2 (en) * | 2014-11-10 | 2019-08-19 | Живодан Са | Compounds based on phenyl substituted with aldehyde fragments, and their use in perfumes |
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