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Application of catalyst, and preparation method for disubstituted cyclohexane carboxylate with adjustable cis-trans ratio

A technology of cyclohexane carboxylate and di-substitution, applied in the field of preparation of di-substituted cyclohexane carboxylate

Active Publication Date: 2018-06-15
SHANGHAI HUAYI ENERGY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the current research on this type of reaction is relatively comprehensive, there are few reports on the influence of the catalyst system and process conditions on the cis-trans content of the product.

Method used

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  • Application of catalyst, and preparation method for disubstituted cyclohexane carboxylate with adjustable cis-trans ratio
  • Application of catalyst, and preparation method for disubstituted cyclohexane carboxylate with adjustable cis-trans ratio
  • Application of catalyst, and preparation method for disubstituted cyclohexane carboxylate with adjustable cis-trans ratio

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Weigh 0.3298g Pd(NO 3 ) 2 (Pd content 15.16wt%), add 6.5g deionized water, add 4.95g Al after it is completely dissolved 2 O 3 The carrier is stirred uniformly, immersed in an equal volume at 25°C for 12 hours, dried at 95°C and calcined at 400°C for 4 hours to obtain a catalyst precursor. Put the catalyst precursor in 10% H 2 / N 2 (Volume fraction) Activated at 300℃ for 4h in the atmosphere, then 1wt% Pd-Al is obtained 2 O 3 Finished catalyst.

[0028] The hydrogenation reaction of diisobutyl phthalate was carried out in a fixed-bed reactor equipped with a stainless steel tube with an inner diameter of 10 mm. The reaction temperature was 120°C, the hydrogen pressure was 5.0 MPa, and H 2 / Ester molar ratio 125, reactant mass space velocity is 0.6h -1 , Sampling and analysis 24h after the start of the reaction (see figure 1 ), RT=22.2min corresponds to trans-diisobutyl 1,2-cyclohexanedicarboxylate, and RT=23.2min corresponds to cis-1,2-cyclohexanedicarboxylate diisobutyl, ob...

Embodiment 2

[0030] Weigh 1.6490g Pd(NO 3 ) 2 (Pd content 15.16wt%), add 6.2g deionized water, add 4.75g Al after it is completely dissolved 2 O 3 The carrier was stirred uniformly, immersed in an equal volume at 25°C for 12h, dried at 95°C and calcined at 400°C for 4h to obtain a catalyst precursor. Put the catalyst precursor in 10% H 2 / N 2 (Volume Fraction) Activated at 300℃ for 4h in the atmosphere, then 5wt% Pd-Al is obtained 2 O 3 Finished catalyst.

[0031] The hydrogenation reaction of diisobutyl phthalate was carried out in a fixed-bed reactor equipped with a stainless steel tube with an inner diameter of 10 mm. The reaction temperature was 120°C, the hydrogen pressure was 5.0 MPa, and H 2 / Ester molar ratio 125, reactant mass space velocity is 0.6h -1 , Sampling and analysis 24 hours after the start of the reaction, the reaction evaluation results obtained are shown in Table 1.

Embodiment 3

[0033] Weigh 3.2980g Pd(NO 3 ) 2 (Pd content 15.16wt%), add 5.9g deionized water, and add 4.50g Al after it is completely dissolved 2 O 3 The carrier was stirred uniformly, immersed in an equal volume at 25°C for 12h, dried at 95°C and calcined at 400°C for 4h to obtain a catalyst precursor. Put the catalyst precursor in 10% H 2 / N 2 (Volume fraction) Activated at 300℃ for 4h in the atmosphere, then 10wt% Pd-Al is obtained 2 O 3 Finished catalyst.

[0034] The hydrogenation reaction of diisobutyl phthalate was carried out in a fixed-bed reactor equipped with a stainless steel tube with an inner diameter of 10 mm. The reaction temperature was 120°C, the hydrogen pressure was 5.0 MPa, and H 2 / Ester molar ratio 125, reactant mass space velocity is 0.6h -1 , Sampling and analysis 24 hours after the start of the reaction, the reaction evaluation results obtained are shown in Table 1.

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Abstract

The invention relates to application of a catalyst, and a preparation method for disubstituted cyclohexane carboxylate with an adjustable cis-trans ratio. The catalyst is used for adjusting the cis-trans ratio of disubstituted cyclohexane carboxylate produced by a hydrogenation reaction of aromatic carboxylate. The preparation method comprises a step of, with aromatic carboxylate as a raw material, carrying out a hydrogenation reaction in the presence of the catalyst so as to produce disubstituted cyclohexane carboxylate, wherein the produced disubstituted cyclohexane carboxylate comprises cis-disubstituted cyclohexane carboxylate and trans-disubstituted cyclohexane carboxylate, and the active component of the catalyst is one or more selected from a group consisting of Ru, Pd and Ni. Withthe preparation method, cis-disubstituted cyclohexane carboxylate and trans-disubstituted cyclohexane carboxylate in different ratios can be prepared; when the active component of the catalyst is Ni,cis-disubstituted cyclohexane carboxylate accounts for 40 to 65%; when the active component of the catalyst is Ru, cis-disubstituted cyclohexane carboxylate accounts for 75 to 90%; and when the activecomponent of the catalyst is Pd, cis-disubstituted cyclohexane carboxylate accounts for 95 to 98%.

Description

Technical field [0001] The invention relates to the use of a catalyst and a preparation method of disubstituted cyclohexane carboxylate with adjustable cis-trans ratio. Background technique [0002] As an important industrial raw material, aromatic carboxylic acid ester compounds are widely used in medicine, perfume, pesticide and other fields. However, due to the presence of its benzene ring, some products cannot meet people's requirements in terms of toxicity and environmental protection, and there is an urgent need to seek alternative products. [0003] Cyclohexane dicarboxylic acid diester compounds (taking o-cyclohexane carboxylic acid ester as an example) are one of the non-aromatic plasticizers, which are characterized by relatively low element mobility and excellent toxicological properties. Biodegradable, it is a kind of excellent performance toys, medical equipment and food contact phthalate diester PVC plasticizer replacement products. [0004] Cyclohexane carboxylate is...

Claims

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Application Information

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IPC IPC(8): B01J23/755B01J23/44B01J23/46C07C67/303C07C69/75
CPCB01J23/44B01J23/462B01J23/755C07B2200/09C07C67/303C07C69/75
Inventor 马金强赵雷蒋文应于舟
Owner SHANGHAI HUAYI ENERGY CHEM
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