Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of low-cost indoline

A low-cost technology for indoline, which is applied in the field of low-cost indoline preparation, can solve the problems of high equipment requirements and equipment investment, high hydrogenation temperature and pressure, and increased environmental protection pressure, and achieve solid waste volume The effect of reduction, good purity, and saving manpower and material resources

Pending Publication Date: 2021-02-02
河北中化鑫宝化工科技有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the patent CN103664733A, a synthetic method of indoline is proposed, and the indoline product is obtained by vacuum distillation after hydrogenation of indole, but on the one hand, the hydrogenation temperature and pressure are relatively high, and the requirements for equipment and High investment in equipment leads to high cost of survival; on the other hand, the catalyst after hydrogenation is not used mechanically, resulting in high cost of hydrogenation, and the catalyst after hydrogenation becomes solid waste, increasing the pressure on environmental protection

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of low-cost indoline
  • Preparation method of low-cost indoline
  • Preparation method of low-cost indoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Weigh 100 grams of indole and 5 grams of catalyst, add them to the autoclave and seal them;

[0034] 2) After nitrogen replacement, the temperature in the kettle was raised to 135°C, and the stirring was started;

[0035] 3) Pulse hydrogen into the hydrogenation tank for hydrogenation, the pressure in the tank is 3.0-4.0Mpa;

[0036] 4) hydrogenation reaction time 3 hours;

[0037] 5) Cool down to 35° C., stop stirring, open the hydrogenation tank, and take out the supernatant to obtain crude indoline.

[0038] 6) The crude product was rectified under reduced pressure at -87kpa to obtain the indoline product.

[0039] Three hydrogenation catalysts of binary nickel, ternary nickel and palladium carbon were selected for screening. Under the same reaction conditions, the crude indoline prepared by different catalysts was analyzed by GC. The experimental results are as follows: figure 1 shown. From figure 1 It can be seen that under the same conditions, the catalyti...

Embodiment 2

[0041] 1) Weigh 100 grams of indole and several grams of ternary nickel catalyst, join in the autoclave and seal;

[0042] 2) After nitrogen replacement, the temperature in the kettle was raised to 135°C, and the stirring was started;

[0043] 3) Pulse hydrogen into the hydrogenation tank for hydrogenation, the pressure in the tank is 3.0-4.0Mpa;

[0044] 4) hydrogenation reaction time 3 hours;

[0045] 5) Cool down to 35° C., stop stirring, open the hydrogenation tank, and take out the supernatant to obtain crude indoline.

[0046] 6) The crude product was rectified under reduced pressure at -87kpa to obtain the indoline product.

[0047] Under the premise that other conditions are consistent, the catalytic hydrogenation experiment of indole and ternary nickel catalyst charging amount 100g: 4g; 100g: 5g; 100g: 6g; analysis, the result is as figure 2 shown. From figure 2 It can be seen from the figure that when the ratio of indole and ternary nickel catalyst for the in...

Embodiment 3

[0049] 1) Weigh 100 grams of indole and 6 grams of ternary nickel catalyst, join in the autoclave and seal;

[0050] 2) After nitrogen replacement, the temperature in the kettle is raised to 120-140°C, and the stirring is started;

[0051] 3) Pulse hydrogen into the hydrogenation tank for hydrogenation, the pressure in the tank is 3.0-4.0Mpa;

[0052] 4) hydrogenation reaction time 3 hours;

[0053] 5) Cool down to 35° C., stop stirring, open the hydrogenation tank, and take out the supernatant to obtain crude indoline.

[0054] 6) The crude product was rectified under reduced pressure at -87kpa to obtain the indoline product.

[0055] Under the premise of other conditions being the same, catalytic hydrogenation experiments with hydrogenation temperatures of 120°C, 130°C, 135°C, and 140°C were carried out, and the prepared crude indoline was analyzed by GC. The results are as follows image 3 shown. From image 3 It can be seen from the figure that when the hydrogenation ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the technical field of indoline, and discloses a low-cost preparation method of indoline. The method comprises the following steps: 1) adding indole extracted from tar and a hydrogenation catalyst into a high-pressure reaction kettle; 2) sealing the reaction kettle, replacing air in the kettle with nitrogen, and heating the reaction kettle to 100-150 DEG C; (3) introducinghydrogen in a pulse manner under the pressure of 3.0-4.0 Mpa, and carrying out hydrogenation reaction; (4) after the reaction is finished, reducing the temperature in the reaction kettle to 35+ / -5 DEG C, then relieving the pressure, taking out the supernatant-indoline crude product, and carrying out reduced pressure rectification to obtain high-quality indoline; and 5) recycling the catalyst at the bottom of the autoclave, and supplementing a trace amount of catalyst during each hydrogenation. The method disclosed by the invention has the advantages of no strict requirements on hydrogenationequipment, high process intrinsic safety, high purity of the prepared indoline, high yield, low cost and less generated solid waste amount, is very suitable for industrial production, reduces the costof waste treatment, and saves a large amount of manpower and material resources.

Description

technical field [0001] The invention relates to the technical field of preparation of indole downstream derivatives, in particular to a low-cost preparation method of indoline. Background technique [0002] Indoline is a very important organic intermediate. The unique chemical structure of indole endows indoline with unique physiological activity when applied to pesticides. Therefore, indoline has a very important position in the field of pesticides. Indoline Phyloline can also be widely used in pharmaceuticals, indoline can be used as a pharmaceutical intermediate, and a series of -3-benzylidene-2 ​​and 3-dihydroindoline can be synthesized by using triethylbenzyl ammonium chloride as a catalyst to react with aromatic aldehydes Indol-2-one derivatives can be used to synthesize bromfenac sodium, which is a non-steroidal anti-inflammatory drug and has a strong analgesic effect. Indoline dyes can also be used as sensitizers for quasi-solid-state dye-sensitized solar cells, with...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/08
CPCC07D209/08Y02P20/584
Inventor 卞长波吕国华纪烈义
Owner 河北中化鑫宝化工科技有限公司