CN112142557B - Low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenation of dimethyl sebacate - Google Patents
Low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenation of dimethyl sebacate Download PDFInfo
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
Abstract
The invention belongs to the field of fine chemical engineering, and provides a low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenating dimethyl sebacate, which comprises the following steps of (1) heating a raw material dimethyl sebacate to a certain temperature, injecting the raw material dimethyl sebacate into a closed type atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw material into fine mist with a certain particle size; (2) mixing hydrogen with the atomized raw materials in the step (1) and feeding the mixture into a premixer of a fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a fixed bed reactor filled with a catalyst, and carrying out hydrogenation reaction under certain process conditions; (4) and the product enters a gas-liquid separator to be separated to obtain the 1, 10-decanediol. The invention innovatively utilizes the atomizing nozzle to atomize the raw material, thereby improving the contact between the dimethyl sebacate and the hydrogen, increasing the solubility of the hydrogen in the raw material and further reducing the reaction pressure.
Description
Technical Field
The invention belongs to the field of catalytic hydrogenation, and relates to a low-pressure synthesis process for preparing 1, 10-decanediol by hydrogenation of dimethyl sebacate.
Background
1, 10-decanediol is a new fine chemical raw material, has two hydroxyl groups positioned at two ends of a carbon chain, has high reaction activity, and can react with organic acid, isocyanate, anhydride and the like to generate different types of derivatives. Due to the unique performance, the polyurethane resin can be used for producing a series of novel fine chemical products and is increasingly applied to the fields of novel polyurethane, polyester, plasticizer, pesticide, medicine, lubricant additive and the like. The method is mainly used for improving the mechanical strength of the product and improving the hydrolysis resistance, heat resistance, chemical corrosion resistance and other performances of the product.
At present, the 1, 10-decanediol production process adopted by researchers at home and abroad is to esterify decanedioic acid with methanol to generate dimethyl decanedioate, then prepare 1, 10-decanediol by hydrogenation, and finally obtain pure 1, 10-decanediol by rectification and purification.
Research institutions at home and abroad carry out a great deal of research on ester hydrogenation reaction, and copper catalysts are generally adopted, and the composition of the catalysts and the reaction process conditions are adjusted according to different raw materials.
CN1011113128 discloses a method for preparing 1, 6-hexanediol by hydrogenation of 1, 6-dimethyl adipate, wherein the hydrogen-ester ratio is 50-150: 1, the load of a catalyst is 0.1-0.5 kg of ester/h, the catalyst is kg, the temperature is 150-300 ℃, the reaction pressure is 4-7 MPa, and Cu/ZnO/Al is adopted2O3The catalyst and the fixed bed reactor have the advantages that the conversion rate of 1, 6-dimethyl adipate is more than 99 percent, and the selectivity of 1, 6-hexanediol is more than 96 percent.
CN102372604A discloses a method for preparing 1, 6-hexanediol by hydrogenation of 1, 6-dimethyl adipate, wherein the reaction time is 5-12 h, the conversion rate of 1, 6-dimethyl adipate is 60-99.9% by adopting a noble metal catalyst and a batch reaction kettle, and the selectivity of 1, 6-hexanediol is more than 70% under the conditions that the hydrogen-ester ratio is 50-200: 1, the temperature is 150-220 ℃, the reaction pressure is 3-5 MPa, the stirring speed is 500-1000 rpm.
CN1565728A discloses a catalyst and a method for preparing 1, 5-pentanediol by hydrogenating 1, 5-dimethyl glutarate, wherein the reaction pressure is 3-5 MPa, the hydrogen-ester ratio is 130-190: 1, and Cu/ZnO/Al is adopted in the presence of a kilogram of catalyst at the reaction temperature of 150-350 ℃ and the catalyst load of 0.01-0.3 kilogram of ester/hour2O3The catalyst and the fixed bed reactor have the advantages that the conversion rate of the 1, 5-dimethyl glutarate is more than 95 percent, and the selectivity is more than 95 percent.
A process for preparing 1, 4-Cyclohexanedimethanol (CHDM) by hydrogenating dimethyl 1, 4-cyclohexanedicarboxylate (DMCD) developed by Ikonbo et al, Japan, chemical and physical Co., Ltd, adopts copper chromite as a catalyst, and adopts palladium and manganese oxides for modification so as to improve the reaction activity. The composition was 47% copper oxide, 48% chromium oxide, 2.5% zinc oxide and 2.5% manganese oxide. The conversion rate is up to 100 percent and the selectivity is up to 95 percent under the conditions that the reaction temperature is 230-280 ℃ and the hydrogenation pressure is 20-25 MPa, and the process has the defect of high pressure, so the application is limited.
In the above ester hydrogenation reaction process, the yield of the higher alcohols depends on the partial pressure of hydrogen and the amount of hydrogen in the reactor. In the traditional process, three phases coexist, namely: a hydrogen gas phase, which is enriched with hydrogen; a fatty acid methyl ester liquid phase which is rich in fatty acid methyl ester, wherein the dissolved hydrogen depends on the partial pressure of hydrogen in the system and the circulation amount of the hydrogen; and (3) solid phase of the catalyst. Because hydrogen is difficult to dissolve in the liquid phase of fatty acid methyl ester, a large hydrogen partial pressure can ensure that the hydrogen has certain solubility in the liquid phase of fatty acid methyl ester. Therefore, the conventional reaction process requires a large hydrogenation pressure.
Disclosure of Invention
The invention aims to atomize the raw material dimethyl sebacate by using an atomizing nozzle, improve the two-phase contact of hydrogen and the dimethyl sebacate and reduce the hydrogenation pressure. Provides a low-pressure synthesis process for preparing 1, 10-decanediol by hydrogenation of dimethyl sebacate, which overcomes the defect of high hydrogen partial pressure in the prior ester hydrogenation technology.
The invention relates to a low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenating dimethyl sebacate, which is characterized in that the 1, 10-decanediol is prepared by heating and atomizing a raw material dimethyl sebacate and then carrying out hydrogenation reaction.
Generally, the synthesis method of the present invention comprises the steps of: heating a raw material dimethyl sebacate to a certain temperature, injecting the raw material into a closed type atomizing nozzle by a plunger pump according to a certain flow rate, and atomizing the raw material into fine mist with a certain particle size; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a fixed bed reactor filled with a catalyst, and carrying out hydrogenation reaction under certain process conditions; (4) and the product enters a gas-liquid separator to be separated to obtain the 1, 10-decanediol.
The heating temperature of the raw material dimethyl sebacate is 60-75 ℃.
The closed atomizing spray head can adopt a centrifugal atomizing spray head.
The closed atomizing spray head can adopt an impact atomizing spray head.
The particle size of the atomized fine mist of the raw materials is 20-150 mu m.
The ratio of the hydrogen to the ester is 1: 15-1: 85.
The catalyst is Cu/ZnO/Al2O3A catalyst.
The catalyst comprises 35-50% of Cu, 15-40% of ZnO and Al2O3The content is 10-50%.
The hydrogenation conditions of the invention are that the reaction pressure is 1.5-5 MPa, the reaction temperature is 220-280 ℃, and the volume space velocity is 0.1-1.5 h-1。
In order to improve the solubility of hydrogen in dimethyl sebacate and reduce the reaction pressure in the hydrogenation process, the invention innovatively applies an atomizing nozzle to atomize the raw material dimethyl sebacate so as to improve the two-phase contact of the hydrogen and the dimethyl sebacate.
The low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenating dimethyl sebacate provided by the invention has the advantages of simple process steps, low reaction pressure and higher reaction performance.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1
(1) Heating dimethyl sebacate to 60 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 20-50 microns; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 40% wt, ZnO 30% wt, Al2O330 wt%) of a fixed bed reactor, under certain conditions. (the specific conditions are shown in Table 1); (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol.
Table 1 example 1 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to acid ratio | pressure/MPa | X/% | S/% |
| 185 | 0.1 | 85:1 | 5 | 94.82 | 96.87 |
| 250 | 0.5 | 60:1 | 4 | 97.15 | 94.68 |
| 200 | 1.2 | 70:1 | 3 | 91.94 | 98.46 |
| 215 | 0.9 | 20:1 | 1.5 | 97.65 | 95.76 |
| 195 | 1.0 | 25:1 | 2 | 90.08 | 98.45 |
| 255 | 1.8 | 15:1 | 2.5 | 93.85 | 92.53 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Example 2
(1) Heating dimethyl sebacate to 65 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 50-120 microns; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 50% wt, ZnO 30% wt, Al2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in Table 2).
Table 2 example 2 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Ratio of hydrogen to acid | pressure/MPa | X/% | S/% |
| 190 | 0.7 | 80:1 | 4 | 93.18 | 94.99 |
| 225 | 0.6 | 60:1 | 2 | 94.95 | 98.78 |
| 245 | 1.4 | 20:1 | 3 | 93.94 | 92.27 |
| 260 | 0.9 | 25:1 | 4.5 | 95.35 | 96.76 |
| 190 | 1.2 | 65:1 | 2 | 95.45 | 96.35 |
| 215 | 0.9 | 20:1 | 5 | 95.75 | 96.23 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Example 3
(1) Heating dimethyl sebacate to 65 ℃, injecting the dimethyl sebacate into a closed impact atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 100-220 microns; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to separate the product into 1, 10-decanediol (the specific reaction conditions are shown in Table 3).
Table 3 example 3 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to acid ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 20:1 | 5 | 93.75 | 97.23 |
| 245 | 1.4 | 20:1 | 3 | 91.94 | 97.27 |
| 190 | 0.7 | 80:1 | 4 | 92.18 | 95.99 |
| 215 | 0.9 | 20:1 | 1.5 | 94.65 | 96.86 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Example 4
(1) Heating dimethyl sebacate to 65 ℃, injecting the dimethyl sebacate into a closed impact atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 180-250 microns; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in the table 4).
Table 4 example 4 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to ester ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 20:1 | 5 | 92.05 | 97.93 |
| 190 | 0.7 | 80:1 | 4 | 91.98 | 96.99 |
| 215 | 0.9 | 20:1 | 1.5 | 90.69 | 97.86 |
| 235 | 0.8 | 45:1 | 3 | 92.99 | 97.86 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Example 5
(1) Heating dimethyl sebacate to 75 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 20-100 microns; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) mixing the raw materials in the step (2) uniformlyContinuously feeding the material into a furnace filled with 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 40 wt%, ZnO 40 wt%, Al2O320 wt%) of a fixed bed reactor, carrying out hydrogenation reaction under certain conditions; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in Table 5).
Table 5 example 5 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to ester ratio | pressure/MPa | X/% | S/% |
| 190 | 0.7 | 80:1 | 4 | 94.68 | 95.89 |
| 225 | 0.6 | 60:1 | 2 | 95.95 | 97.78 |
| 245 | 1.4 | 20:1 | 3 | 94.74 | 93.34 |
| 260 | 0.9 | 25:1 | 4.5 | 95.95 | 96.36 |
| 190 | 1.2 | 65:1 | 2 | 95.55 | 96.45 |
| 215 | 0.9 | 20:1 | 5 | 97.75 | 95.27 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Example 6
(1) Heating dimethyl sebacate to 75 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 40-180 mu m; (2) mixing hydrogen with the atomized raw material in the step (1) and feeding the mixture into a premixer of the fixed bed reactor; (3) Continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in Table 6).
Table 6 example 6 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to ester ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 20:1 | 5 | 97.35 | 96.84 |
| 190 | 0.7 | 80:1 | 4 | 94.88 | 97.89 |
| 215 | 0.9 | 20:1 | 1.5 | 94.59 | 97.85 |
| 235 | 0.8 | 45:1 | 3 | 93.99 | 96.87 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Comparative example 6
(1) Heating dimethyl sebacate to 75 ℃, and injecting the dimethyl sebacate into a premixer at a certain flow rate by a plunger pump; (2) mixing hydrogen with the raw materials in the step (1) and feeding the mixture into a premixer of a fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol.
TABLE 7 comparative example 6 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to ester ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 90:1 | 8 | 95.86 | 94.23 |
| 190 | 0.7 | 80:1 | 9 | 95.88 | 97.89 |
| 215 | 0.9 | 20:1 | 1.5 | 69.57 | 89.85 |
| 235 | 0.8 | 45:1 | 3 | 79.67 | 90.82 |
Note:X1, 10-sebacic acid conversion;S，and (4) selectivity of decanediol.
Example 7
(1) Heating dimethyl sebacate to 75 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 50-200 microns; (2) mixing hydrogen with the atomized raw materials in the step (1) and feeding the mixture into a premixer of a fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in Table 8).
Table 8 example 7 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to oil ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 20:1 | 5 | 95.76 | 96.24 |
| 245 | 1.4 | 20:1 | 2 | 93.95 | 96.27 |
| 190 | 0.7 | 80:1 | 4 | 93.18 | 95.78 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
Comparative example 7
(1) Heating dimethyl sebacate to 75 ℃, injecting the dimethyl sebacate into a closed centrifugal atomizing nozzle by a plunger pump at a certain flow rate, and atomizing the raw materials into fine mist with a certain particle size of 50-200 microns; (2) mixing hydrogen with the atomized raw materials in the step (1) and feeding the mixture into a premixer of a fixed bed reactor; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a container containing 10ml of 20-40 mesh Cu/ZnO/Al2O3Catalyst (Cu 45 wt%, ZnO 35 wt%, Al)2O320 wt%) of a fixed bed reactor, under certain conditions to carry out a hydrogenation reaction; (4) and the product enters a separator to be separated to obtain the 1, 10-decanediol (the specific reaction conditions are shown in Table 9).
TABLE 9 comparative example 7 reaction conditions and results
| Reaction temperature/. degree.C | Space velocity/h-1 | Hydrogen to oil ratio | pressure/MPa | X/% | S/% |
| 215 | 0.9 | 110:1 | 8 | 97.74 | 95.26 |
| 245 | 1.4 | 20:1 | 2 | 68.48 | 90.31 |
| 190 | 0.7 | 80:1 | 4 | 88.59 | 93.75 |
Note:X1, 10-sebacic acid conversion;S，decanediol selectivity.
From the above examples, it can be seen that the low-pressure synthesis process for preparing 1, 10-decanediol by hydrogenating dimethyl sebacate provided by the invention has the advantages of simple process steps, low reaction pressure and high reaction performance.
Claims (7)
1. A low-pressure synthesis method for preparing 1, 10-decanediol by hydrogenating dimethyl sebacate is characterized in that a raw material dimethyl sebacate is heated and atomized and then subjected to hydrogenation reaction to prepare the 1, 10-decanediol, and comprises the following steps: (1) heating the raw material dimethyl sebacate, injecting the heated raw material dimethyl sebacate into a closed type atomizing nozzle by a plunger pump, and atomizing the raw material into fine mist; (2) mixing hydrogen and the atomized raw material in the step (1) and feeding the mixture into a premixer of a fixed bed reactor, wherein the hydrogen-ester ratio is 1: 15-1: 85; (3) continuously feeding the uniformly mixed raw materials in the step (2) into a fixed bed reactor filled with a catalyst to carry out hydrogenation reaction, wherein the hydrogenation conditions are as follows: the reaction pressure is 1.5-5 MPa, the reaction temperature is 220-280 ℃, and the volume space velocity is 0.1-1.5 h-1(ii) a (4) And the product enters a gas-liquid separator to be separated to obtain the 1, 10-decanediol.
2. The synthesis method according to claim 1, wherein the heating temperature of the raw material dimethyl sebacate is 60-75 ℃.
3. The synthesis method according to claim 1, wherein the closed atomizer is a centrifugal atomizer.
4. The synthesis method according to claim 1, wherein the closed atomizer is an impact atomizer.
5. The synthesis process according to claim 1, wherein the atomized fine mist has a particle size of 20 to 150 μm.
6. The synthesis method according to claim 1, characterized in that the catalyst is Cu/ZnO/Al2O3A catalyst.
7. The synthesis method according to claim 1 or 6, wherein the catalyst component comprises 35-50% of Cu, 15-40% of ZnO, and Al2O3The content is 10-50%.
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