CN101186554B - Method for preparing endo-tetrahydrodicyclopentadiene from ethylene by-product C9 - Google Patents
Method for preparing endo-tetrahydrodicyclopentadiene from ethylene by-product C9 Download PDFInfo
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- CN101186554B CN101186554B CN2007101510073A CN200710151007A CN101186554B CN 101186554 B CN101186554 B CN 101186554B CN 2007101510073 A CN2007101510073 A CN 2007101510073A CN 200710151007 A CN200710151007 A CN 200710151007A CN 101186554 B CN101186554 B CN 101186554B
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Abstract
The invention relates to a preparation method of endo-tetrahydro-dicyclopentadiene. The method of preparing endo-tetrahydro-dicyclopentadiene with ethylene byproduct C9 is that: the ethylene byproductC9 is filled into a hydrogenator 1 that is filled with catalyst; hydrogenation is carried out under warming and pressuring condition and with the function of catalyst; hydrogenated materials that com e out of the hydrogenator 1 enter a second hydrogenator that is filled with catalyst, and hydrogenation is carried out under the warming and pressuring condition and the function of catalyst; hydrogenated materials that come out of the hydrogenator 2 enter a rectifying tower 1, and distillate of 120 DEG C to 190 DEG C that is produced under normal pressure distillation is acquired from the top of the tower; materials that come out of the rectifying tower 1 enters a rectifying tower 2, and distillate of 190 DEG C to 192 DEG C that is produced under normal pressure distillation is acquired from the top of the tower, and the distillate is the endo-tetrahydro-dicyclopentadiene product with the purity higher than 97 percent.
Description
Technical field
The present invention relates to a kind of method of producing bridge-type tetrahydro-dicyclopentadiene, be specially adapted to produce bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9.
Background technology
Along with the development of aerospace industry and national defense industry, more and more higher to the requirement of the air speed of aircraft and flying distance.The size of aircraft power has directly determined its voyage, the speed of a ship or plane and load.Under the long-pending condition of limited of aircraft fuel casing, the fuel of high-density and high volume calorific value can be aircraft provides more energy, and the application of high-density propellant is just more and more important.The high-density hydrocarbon fuel be in order to develop modern high performance tactics, strategic cruise missiles and a class of synthetic have high-density, a high volume calorific value can storage type liquid hydrocarbon fuel.Compare with conventional kerosene stock, the aircraft voyage is increased more than 15%, improve aircraft performance so can be used as the power fuel of aircraft.Hanging type tetrahydrochysene dicyclopentadiene (being JP-10 fuel) has lower freezing point (78 ℃) and the higher combustion heat (39.6GJm
3), improved the use properties of fuel under the low temperature greatly, be present consumption maximum, the widest, the good comprehensive properties high-density hydrocarbon fuel of purposes, be the ideal fuels of modern novel hypersonic vehicle.JP-10 fuel is rare pure compound in the class high-density hydrocarbon fuel, and it not only can act as a fuel but also can be used as the thinner of other heavy fuels separately, was a kind of liquid fuel of excellent property.
Past industrial production hanging type tetrahydrochysene dicyclopentadiene, be to be raw material with cyclopentadiene, at first allow the cyclopentadiene dimerization be bridge dicyclopentadiene, again the bridge dicyclopentadiene shortening is obtained bridge-type tetrahydro-dicyclopentadiene, bridge-type tetrahydro-dicyclopentadiene catalysis again makes the transition, and promptly obtains hanging type tetrahydrochysene dicyclopentadiene.US4270014, JP81103122, SU1576561, CN1911878 have described such method.
Produce the raw material cyclopentadiene of hanging type tetrahydrochysene dicyclopentadiene, from coal tar and ethylene by-product C5, extract and obtain.Because cyclopentadiene has special chemical activity and inflammable and explosive danger, in the production process of cyclopentadiene, must take strict security measures, make production cost improve greatly, loss increases greatly.And the cyclopentadiene that makes also must be through polymerization, obtain the dipolymer dicyclopentadiene after, just can be used for hydrogenation to produce bridge-type tetrahydro-dicyclopentadiene, and obtain hanging type tetrahydrochysene dicyclopentadiene final transition.
Therefore, adopt more cheap raw material and simpler explained hereafter bridge-type tetrahydro-dicyclopentadiene necessary.
Summary of the invention
The object of the present invention is to provide that the more cheap raw material of a kind of employing---ethylene by-product C9 produces the method for bridge-type tetrahydro-dicyclopentadiene.
Ethylene by-product C9 and C5 are similar, also contain a large amount of dicyclopentadiene.The present invention is directly ethylene by-product C9 shortening, and the material behind the hydrogenation carries out rectifying separation, obtains high-quality hydrogenation solvent oil and bridge-type tetrahydro-dicyclopentadiene.
Realized by following technical proposals:
Ethylene by-product C9 is fed the hydrogenator 1 that catalyzer is housed, heating, carrying out hydrogenation, 30 ℃～150 ℃ of hydrogenator 1 hydrogenation reaction temperature under pressurization and the catalyst action; Reaction pressure 2.0MPa～6.0MPa; Oil, gas air speed h
-10.3～7.0; Hydrogen-oil ratio 200～1200V/V.
Material behind the hydrogenation that hydrogenator 1 comes out enters second hydrogenator that catalyzer is housed, and is heating, is carrying out hydrogenation, 100 ℃～300 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 2.0MPa～6.0MPa under pressurization and the catalyst action; Oil, gas air speed h
-10.3～5.0; Hydrogen-oil ratio 200～800V/V.
The hydrogenation material that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges; Rectifying tower 1 can atmospheric operation, also can negative-pressure operation.During atmospheric operation, 190 ℃ of tower top temperatures, 210 ℃～230 ℃ of tower still temperature.During negative-pressure operation, 70 ℃～145 ℃ of tower top temperatures, 160 ℃～190 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges; Rectifying tower 2 can atmospheric operation, also can negative-pressure operation.During atmospheric operation, 192 ℃ of rectifying tower 2 tower top temperatures, 215 ℃～235 ℃ of tower still temperature.During negative-pressure operation, 115 ℃～150 ℃ of tower top temperatures, 165 ℃～195 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.The bottom product of the overhead product of rectifying tower 1 and rectifying tower 2 can further handle obtaining high-quality hydrogenation solvent oil.
Above-mentioned hydrogenator 1 and hydrogenator 2 use fixed-bed reactor; The catalyzer that installs additional is general nickel series hydrogenating catalyst or cobalt-molybdenum series catalyst, QLC-1 type hydrogenation catalyst for example, active ingredient NiO-D-F/Al
2O
3-MO
2
Above-mentioned rectifying tower 1, rectifying tower 2 can be used packing tower, also can use tray column.
Aforesaid operations pressure all is gauge pressure.
Method of the present invention also can be used for producing bridge-type tetrahydro-dicyclopentadiene from ethylene by-product C5.
The invention has the advantages that, directly utilize ethene C9 hydrogenation, rectifying, produce bridge-type tetrahydro-dicyclopentadiene, overcome and produced bridge-type tetrahydro-dicyclopentadiene technology inherent defective in the past, efficiently the comprehensive utilization that has realized the ethylene by-product thing, great positive effect is all arranged for chemical industry and national defense construction.
Description of drawings
Fig. 1 is a device synoptic diagram of the present invention.Among Fig. 1: 1 hydrogenator 1,2nd, hydrogenator 2; The 3rd, rectifying tower 1, the 4th, rectifying tower 2, S1 is a raw material---ethylene by-product C9, S2 is come out a material behind the hydrogenation of hydrogenator 1, S3 is the hydrogenation material that hydrogenator 2 comes out, and S4 is the material that comes out at the bottom of rectifying tower 1 tower, and S5 is the material that rectifying tower 1 cat head comes out, S6 is the bottom product of rectifying tower 2, and S7 is the bridge-type tetrahydro-dicyclopentadiene product.
Embodiment
Referring to accompanying drawing 1, hydrogenator 1 (1), hydrogenator 2 (2), hydrogenator 1 and hydrogenator 2 all are fixed-bed reactor, QLC-1 type hydrogenation catalyst is housed, rectifying tower 1 (3) and rectifying tower 2 (4) orders are cascaded, and rectifying tower 1, rectifying tower 2 can be used packing tower, also can use tray column.Ethylene by-product C9S1 feeds the hydrogenator 1 that catalyzer is housed, and is heating, is carrying out hydrogenation, 30 ℃～150 ℃ of hydrogenator 1 hydrogenation reaction temperature under pressurization and the catalyst action; Reaction pressure 2.0MPa～6.0MPa; Oil, gas air speed h
-10.3～7.0; Hydrogen-oil ratio 200～1200V/V.
Material S2 behind the hydrogenation that hydrogenator 1 comes out enters second hydrogenator that catalyzer is housed, and is heating, is carrying out hydrogenation, 100 ℃～300 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 2.0MPa～6.0MPa under pressurization and the catalyst action; Oil, gas air speed h
-10.3～5.0; Hydrogen-oil ratio 200～800V/V.
The hydrogenation material S3 that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges; Rectifying tower 1 can atmospheric operation, also can negative-pressure operation.During atmospheric operation, 190 ℃ of tower top temperatures, 210 ℃～230 ℃ of tower still temperature.During negative-pressure operation, 70 ℃～145 ℃ of tower top temperatures, 160 ℃～190 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
The material S4 that comes out at the bottom of rectifying tower 1 tower enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges, the material S5 that rectifying tower 1 cat head comes out; Enter rectifying tower 2, rectifying tower 2 can atmospheric operation, also can negative-pressure operation.During atmospheric operation, 192 ℃ of rectifying tower 2 tower top temperatures, 215 ℃～235 ℃ of tower still temperature.During negative-pressure operation, 115 ℃～150 ℃ of tower top temperatures, 165 ℃～195 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product S7.The bottom product S6 of the overhead product of rectifying tower 1 and rectifying tower 2 can further handle obtaining high-quality hydrogenation solvent oil.
Following examples are used for further specifying content of the present invention, do not limit application of the present invention.Percentage ratio among the embodiment is mass percent without exception except that dated person is arranged, and pressure is gauge pressure without exception.
Ethylene by-product C9 feeds the hydrogenator 1 that QLC-1 type hydrogenation catalyst is housed, 30 ℃ of hydrogenator 1 hydrogenation reaction temperature; Reaction pressure 6.0MPa; Oil, gas air speed h
-10.3; Hydrogen-oil ratio 200V/V.
The material that hydrogenator 1 comes out enters the hydrogenator 2 that QLC-1 type hydrogenation catalyst is housed, 300 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 2.0MPa; Oil, gas air speed h
-15.0; Hydrogen-oil ratio 800V/V.
The hydrogenation material that hydrogenator 2 (2) comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges.Atmospheric operation, 190 ℃ of tower top temperatures, 230 ℃ of tower still temperature.Rectifying tower 1 adopts packing tower.
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges; Rectifying tower 2 negative-pressure operations.115 ℃ of tower top temperatures, 165 ℃ of tower still temperature, tower top pressure-0.095MPa.Rectifying tower 2 adopts tray column.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.
Ethylene by-product C9 feeds the hydrogenator 1 that QLC-1 type hydrogenation catalyst is housed, 150 ℃ of hydrogenator 1 hydrogenation reaction temperature; Reaction pressure 2.0MPa; Oil, gas air speed h
-17.0; Hydrogen-oil ratio 1200V/V.
The material that hydrogenator 1 comes out enters the hydrogenator 2 that QLC-1 type hydrogenation catalyst is housed, 100 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 6.0MPa; Oil, gas air speed h
-10.3; Hydrogen-oil ratio 200V/V.
The hydrogenation material that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges.Atmospheric operation, 190 ℃ of tower top temperatures, 210 ℃ of tower still temperature.Rectifying tower 1 adopts packing tower.
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges; Rectifying tower 2 negative-pressure operations.150 ℃ of tower top temperatures, 195 ℃ of tower still temperature, tower top pressure-0.070MPa.Rectifying tower 2 adopts packing tower.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.
Ethylene by-product C9 feeds the hydrogenator 1 that QLC-1 type hydrogenation catalyst is housed, 150 ℃ of hydrogenator 1 hydrogenation reaction temperature; Reaction pressure 2.0MPa; Oil, gas air speed h
-17.0; Hydrogen-oil ratio 1200V/V.
The material that hydrogenator 1 comes out enters the hydrogenator 2 that QLC-1 type hydrogenation catalyst is housed, 100 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 6.0MPa; Oil, gas air speed h
-10.3; Hydrogen-oil ratio 200V/V.
The hydrogenation material that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges.Negative-pressure operation, 145 ℃ of tower top temperatures, 190 ℃ of tower still temperature, tower top pressure-0.095MPa.Rectifying tower 1 adopts tray column.
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges; Rectifying tower 2 atmospheric operations.192 ℃ of rectifying tower 2 tower top temperatures, 215 ℃ of tower still temperature.Rectifying tower 2 adopts packing tower.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.
Ethylene by-product C9 feeds the hydrogenator 1 that QLC-1 type hydrogenation catalyst is housed, 150 ℃ of hydrogenator 1 hydrogenation reaction temperature; Reaction pressure 2.0MPa; Oil, gas air speed h
-17.0; Hydrogen-oil ratio 1200V/V.
The material that hydrogenator 1 comes out enters the hydrogenator 2 that QLC-1 type hydrogenation catalyst is housed, 100 ℃ of the temperature of reaction of hydrogenator 2, reaction pressure 6.0MPa; Oil, gas air speed h
-10.3; Hydrogen-oil ratio 200V/V.
The hydrogenation material that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges.Negative-pressure operation, 70 ℃ of tower top temperatures, 160 ℃ of tower still temperature, tower top pressure-0.070MPa.Rectifying tower 1 adopts tray column.
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, and cat head obtains the cut of 190 ℃～192 ℃ of normal pressure boiling ranges; Rectifying tower 2 atmospheric operations.192 ℃ of rectifying tower 2 tower top temperatures, 235 ℃ of tower still temperature.Rectifying tower 2 adopts tray column.
The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.
Claims (10)
1. produce the method for bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9, it is characterized in that, ethylene by-product C9 is fed the hydrogenator 1 that catalyzer is housed, heating, carrying out hydrogenation under pressurization and the catalyst action;
Material behind the hydrogenation that hydrogenator 1 comes out enters second hydrogenator that catalyzer is housed, and is heating, is carrying out hydrogenation under pressurization and the catalyst action;
The hydrogenation material that hydrogenator 2 comes out enters rectifying tower 1, and cat head obtains the cut of 120 ℃～190 ℃ of normal pressure boiling ranges; Rectifying tower 1 atmospheric operation or negative-pressure operation;
The material that rectifying tower 1 tower still comes out enters rectifying tower 2, rectifying tower 2 atmospheric operations or negative-pressure operation; The cut that the normal pressure boiling range that rectifying tower 2 cats head obtain is 190 ℃～192 ℃ is purity greater than 97% bridge-type tetrahydro-dicyclopentadiene product.
2. the method for producing bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9 according to claim 1 is characterized in that 30 ℃～150 ℃ of described hydrogenator 1 hydrogenation reaction temperature; Reaction pressure 2.0MPa～6.0MPa; Oil, gas air speed h
-10.3～7.0; Hydrogen-oil ratio 200～1200V/V.
3. the method for producing bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9 according to claim 1 is characterized in that 100 ℃～300 ℃ of the temperature of reaction of described hydrogenator 2, reaction pressure 2.0MPa～6.0MPa; Oil, gas air speed h
-10.3～5.0; Hydrogen-oil ratio 200～800V/V.
4. according to claim 1ly produce the method for bridge-type tetrahydro-dicyclopentadiene, it is characterized in that by ethylene by-product C9, during described rectifying tower 1 atmospheric operation, 190 ℃ of tower top temperatures, 210 ℃～230 ℃ of tower still temperature.
5. the method for producing bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9 according to claim 1, it is characterized in that, during described rectifying tower 1 negative-pressure operation, 70 ℃～145 ℃ of tower top temperatures, 160 ℃～190 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
6. according to claim 1ly produce the method for bridge-type tetrahydro-dicyclopentadiene, it is characterized in that by ethylene by-product C9, during described rectifying tower 2 atmospheric operations, 215 ℃～235 ℃ of tower still temperature.
7. the method for producing bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9 according to claim 1, it is characterized in that, during described rectifying tower 2 negative-pressure operations, 115 ℃～150 ℃ of tower top temperatures, 165 ℃～195 ℃ of tower still temperature, tower top pressure-0.070MPa～-0.095MPa.
8. the method for producing bridge-type tetrahydro-dicyclopentadiene by ethylene by-product C9 according to claim 1 is characterized in that described hydrogenator 1 and hydrogenator 2 use fixed-bed reactor.
9. ethylene by-product C9 according to claim 1 produces the method for bridge-type tetrahydro-dicyclopentadiene, it is characterized in that, the catalyzer that installs additional in described hydrogenator 1 and the hydrogenator 2 is general nickel series hydrogenating catalyst or cobalt-molybdenum series catalyst.
10. according to claim 1ly produce the method for bridge-type tetrahydro-dicyclopentadiene, it is characterized in that, described rectifying tower 1, rectifying tower 2 usefulness packing towers or use tray column by ethylene by-product C9.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101510073A CN101186554B (en) | 2007-12-13 | 2007-12-13 | Method for preparing endo-tetrahydrodicyclopentadiene from ethylene by-product C9 |
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|---|---|---|---|
| CN2007101510073A CN101186554B (en) | 2007-12-13 | 2007-12-13 | Method for preparing endo-tetrahydrodicyclopentadiene from ethylene by-product C9 |
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| Publication Number | Publication Date |
|---|---|
| CN101186554A CN101186554A (en) | 2008-05-28 |
| CN101186554B true CN101186554B (en) | 2010-12-15 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924216B (en) * | 2012-11-02 | 2014-12-24 | 中科合成油技术有限公司 | Synthetic method for exo-tetrahydrodicyclopentadiene (THDCPD) |
| CN105294381A (en) * | 2015-09-10 | 2016-02-03 | 西安近代化学研究所 | Method for separating and purifying bridge type tetrahydrodicyclopentadiene |
| CN109232163A (en) * | 2018-10-24 | 2019-01-18 | 濮阳市联众兴业化工有限公司 | A kind of dicyclopentadiene hydrogenated method for preparing bridge-type tetrahydro-dicyclopentadiene |
| CN114436753B (en) * | 2020-10-20 | 2024-01-30 | 中国石油化工股份有限公司 | Adamantane and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4270014A (en) * | 1979-04-30 | 1981-05-26 | Ashland Oil, Inc. | Production of high energy fuel |
| CN1911878A (en) * | 2005-08-09 | 2007-02-14 | 中国石化上海石油化工股份有限公司 | Method of preparing tetrahydrobicyclo pentadiene by continuous hydrogenation of bicyclopentadiene |
| CN1948441A (en) * | 2006-10-08 | 2007-04-18 | 广东省茂名华粤集团有限公司 | Petroleum hydrocarbon cracking carbon nine cut fraction hydrogenation technology |
| CN101066902A (en) * | 2007-05-16 | 2007-11-07 | 天津天大天海化工新技术有限公司 | Process of separating cyclopentadiene and methyl cydopentadiene from ethylene side C9 product |
-
2007
- 2007-12-13 CN CN2007101510073A patent/CN101186554B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4270014A (en) * | 1979-04-30 | 1981-05-26 | Ashland Oil, Inc. | Production of high energy fuel |
| CN1911878A (en) * | 2005-08-09 | 2007-02-14 | 中国石化上海石油化工股份有限公司 | Method of preparing tetrahydrobicyclo pentadiene by continuous hydrogenation of bicyclopentadiene |
| CN1948441A (en) * | 2006-10-08 | 2007-04-18 | 广东省茂名华粤集团有限公司 | Petroleum hydrocarbon cracking carbon nine cut fraction hydrogenation technology |
| CN101066902A (en) * | 2007-05-16 | 2007-11-07 | 天津天大天海化工新技术有限公司 | Process of separating cyclopentadiene and methyl cydopentadiene from ethylene side C9 product |
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