Process for preparing tricyclodecane dimethylamine from dicyclopentadiene and application of tricyclodecane dimethylamine

A technology of dicyclopentadiene and decane dimethylamine, applied in the field of IPCC07C, can solve the problems of tricyclodecane diformaldehyde thermal instability, high overall cost, catalyst loss, etc., achieve good industrial application prospects and improve reaction Depth, the effect of avoiding yield loss

Pending Publication Date: 2022-07-01
广东希必达新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent No. 7,301,057B2 discloses a method for preparing tricyclodecane dicarbaldehyde by hydroformylation of dicyclopentadiene, but the catalyst used is a noble metal Rh system. Due to the high cost of Rh, even if there is a loss of catalyst ppm level It is also unacceptable; the current Rh recovery method is to reclaim and separate the Rh catalyst (patent WO0220451) by membrane after the reaction finishes; Or in the air, it is easy to polycondense into high-boiling-point high-viscosity substances, which can easily block the membrane for recycling precious metal catalysts, resulting in the loss of catalysts and greatly increasing the cost
Chinese patent CN1446793A discloses a method for forming diamines from dialdehyde and ammonia under the action of a catalyst, using tricyclodecane dimethylaldehyde as a substrate to prepare tricyclodecane dimethylamine by catalytic amination, but the patent does not mention and the source of tricyclodecane diformaldehyde; and it is well known in the industry that tricyclodecane diformaldehyde is unstable when heated, and under existing separation conditions, side reactions such as condensation easily occur and consume tricyclodecane diformaldehyde, resulting in tricyclodecane diformaldehyde The yield of alkanedicarbaldehyde is extremely low, so the overall cost of preparing diamine from the double ring is high, and the economic benefit is low

Method used

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  • Process for preparing tricyclodecane dimethylamine from dicyclopentadiene and application of tricyclodecane dimethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The present embodiment provides a process for preparing tricyclodecane dimethanol with dicyclopentadiene, and the process steps are specifically:

[0052] In a 250ml autoclave, add 60g of solvent, 50g of dicyclopentadiene, 0.36g of metal catalyst, 0.1g of tris(2,4-di-tert-butyl) phenyl phosphite, seal the reactor, and use nitrogen and synthesis gas in turn Each autoclave was purged three times, filled with synthesis gas, and the temperature was increased. The conditions in the control reactor were kept at 120°C and 6MPa. The reaction was terminated after 6 hours of reaction, the temperature was lowered and the pressure was lowered, the synthesis gas was vented, and the obtained product was distilled to obtain 62 g of tricyclodecane dimethanol with a yield of 84%.

[0053] The solvent is tetrahydrofuran.

[0054] The catalyst is cobalt acetylacetonate and ruthenium trichloride with a weight ratio of 35:1.

[0055] The ligand is tris(2,4-di-tert-butyl) phenyl phosphite...

Embodiment 2

[0058] The present embodiment provides a process for preparing tricyclodecane dimethanol with dicyclopentadiene, and the process steps are specifically:

[0059] In a 1000ml autoclave, add 300g solvent, 300g dicyclopentadiene, 1.64g metal catalyst, 1.1g ligand, seal the autoclave, use nitrogen and syngas to purge the autoclave three times in turn, fill with syngas to start Heat up and boost. The conditions in the control reactor were kept at 110°C and 8MPa. After the reaction for 8 hours, the reaction was terminated, the temperature was lowered and the pressure was lowered, the synthesis gas was vented, and the obtained product was distilled to obtain 347 g of tricyclodecane dimethanol with a yield of 78%.

[0060] The solvent is toluene.

[0061] The catalyst is cobalt chloride and carbonyl ruthenium chloride in a weight ratio of 15:1.4.

[0062] The ligand is triphenylphosphine.

[0063] The synthesis gas is a combination of carbon monoxide and hydrogen; the volume ratio...

Embodiment 3

[0065] The present embodiment provides a process for preparing tricyclodecane dimethanol with dicyclopentadiene, and the process steps are specifically:

[0066] In a 2000ml autoclave, add 500g solvent, 550g dicyclopentadiene, 3.92g metal catalyst, 0.9g ligand, seal the autoclave, use nitrogen and syngas to purge the autoclave three times in turn, fill with syngas to start Heat up and boost. The conditions in the control reactor were kept at 120°C and 6MPa. The reaction was terminated after 6 hours of reaction, the temperature was lowered and the pressure was lowered, the synthesis gas was vented, and the obtained product was distilled to obtain 661 g of tricyclodecane dimethanol with a yield of 81%.

[0067] The solvent is tetrahydrofuran.

[0068] The catalyst is cobalt acetylacetonate and ruthenium trichloride in a weight ratio of 38.5:0.7.

[0069] The ligand is tris(2,4-di-tert-butyl) phenyl phosphite.

[0070] The synthesis gas is a combination of carbon monoxide and...

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Abstract

The invention relates to the technical field of IPC C07C, in particular to a process for preparing tricyclodecane dimethylamine from dicyclopentadiene and application of the tricyclodecane dimethylamine. The process comprises the following steps: S1, adding dicyclopentadiene, a metal catalyst and a ligand into a reaction device, and reacting to obtain tricyclodecane dimethyl carbinol; s2, reacting the tricyclodecane dimethyl carbinol obtained in the step S1 with mixed gas under the action of a supported catalyst to obtain a tricyclodecane dimethylamine finished product, the mixed gas is a combination of hydrogen and ammonia gas. The method provided by the invention is simple in process route and high in raw material economy, material loss in the separation process is avoided, and the production cost is remarkably reduced.

Description

technical field [0001] The invention relates to the technical field of IPC CO7C, in particular to a process for preparing tricyclodecane dimethylamine from dicyclopentadiene and application thereof. Background technique [0002] Tricyclodecane dimethylamine (Chinese alias: dicyclopentane dimethylamine, English name: TCD-diamine, CAS number: 129680-22-4) as an important chemical raw material, has good stability and can be combined with Polycondensation of a variety of dibasic acids to prepare new functional materials for special purposes. The special tricyclodecane structure endows tricyclodecanedimethylamine with extremely excellent heat resistance, and its thermal decomposition temperature is significantly higher than that of aliphatic amines, which has broad application prospects in the field of special functional materials. [0003] US Patent US7317128B2 discloses a method for preparing tricyclodecanedicarbaldehyde from dicyclopentadiene through hydroformylation reaction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/16C07C211/19C07C29/36C07C31/27
CPCC07C209/16C07C29/36C07C2603/68C07C31/278C07C211/19
Inventor 张晓超左洪亮刘阳李燕平李红仙曾庆亮黄杰
Owner 广东希必达新材料科技有限公司
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