CN106673940A - Entrainer for separating bicyclic alkane and polycyoalkane and method using entrainer to separate bicyclic alkane and polycyoalkane - Google Patents
Entrainer for separating bicyclic alkane and polycyoalkane and method using entrainer to separate bicyclic alkane and polycyoalkane Download PDFInfo
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- CN106673940A CN106673940A CN201611227560.6A CN201611227560A CN106673940A CN 106673940 A CN106673940 A CN 106673940A CN 201611227560 A CN201611227560 A CN 201611227560A CN 106673940 A CN106673940 A CN 106673940A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/47—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
- C07C13/48—Completely or partially hydrogenated naphthalenes
- C07C13/50—Decahydronaphthalenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/61—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with a bridged indene ring, e.g. dicyclopentadiene
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Abstract
The invention discloses an entrainer for separating bicyclic alkane and polycyoalkane and a method using the entrainer to separate bicyclic alkane and polycyoalkane, in particular to a multi-element entrainer for separating trans-decalin and exo-tetrahydrodicyclopentadiene with same boiling point. The entrainer is prepared from water and an organic oxygen-containing compound with certain polarity, wherein the organic oxygen-containing compound and the water can form azeotrope. The entrainer has the advantages that the bicyclic alkane and polycyoalkane can be effectively separated at normal pressure, especially the distillation separation of the trans-decalin and the exo-tetrahydrodicyclopentadiene; the condensation reaction of the exo-tetrahydrodicyclopentadiene in the distilling process is avoided.
Description
Technical field
The present invention relates to a kind of separate bicyclic and polycyoalkane entrainer and separate bicyclic and polycyoalkane with entrainer
Method, particularly separate the polynary entrainer of the almost identical trans-decalin of boiling point and hanging type tetrahydrochysene dicyclopentadiene, category
In the separation engineering field of petrochemical industry.
Background technology
Polycyoalkane typically has higher density and combustion heat value, can be used as high-density propellant, such as dicyclopentadiene
(DCPD) it is hydrogenated to prepare bridge-type tetrahydro-dicyclopentadiene (endo-THDCPD), then it is obtained hanging four through isomerization reaction
Hydrogen dicyclopentadiene (exo-THDCPD), hanging type tetrahydrochysene dicyclopentadiene (exo-THDCPD) is a kind of Low Temperature Liquid of function admirable
Body high-density propellant, is widely used as the propellant of guided missile, aircraft and torpedo.
Isomerization of bridge-type tetrahydro-dicyclopentadiene can compare traditional L strong acid AlCl using molecular sieve as catalyst3Have
It is reusable, the advantages of reduce environmental pollution, but because surface acid density is relatively low, need higher reaction temperature, so as to
By-product growing amount is larger.As shown in figure 1, by-product mainly includes trans-decalin and its isomerization product, diamantane (obsolete) etc., lead
Cause product purification relatively difficult.
The metal component of hydrogen can be activated in molecular sieve surface load, the generation of diamantane (obsolete) can be suppressed, but while can be led
Causing the growing amount of trans-decalin increases, and because its boiling point is almost identical with purpose product hanging type tetrahydrochysene dicyclopentadiene, is
185-186 DEG C, thus the detached difficulty of rectification is larger, needs using special rectification isolation technics, can just reach target product
The requirement of thing purity 98.5%.
Prior art proposes the rectifying column operating condition for separating hanging type tetrahydrochysene dicyclopentadiene：Operating pressure 5kPa, column plate
26 pieces of number, feed entrance point is the 12nd block of column plate, and reflux ratio is 10, and condenser and reboiler temperature are respectively 64.6 DEG C and 76.4
DEG C, tower top hanging type tetrahydrochysene dicyclopentadiene purity is up to 98.8%.In prior art, isomerization of bridge-type tetrahydro-dicyclopentadiene is anti-
The method for answering product to carry out rectification under vacuum, operating pressure 2-10kPa, tower top temperature is 60-105 DEG C, and bottom temperature is 70-120
℃.The method of above prior art separates hanging type tetrahydrochysene dicyclopentadiene using rectification under vacuum, and does not propose trans-decalin
It is difficult to detached problem.
Consideration is additionally needed, hanging type tetrahydrochysene dicyclopentadiene is at relatively high temperatures it may happen that condensation reaction, essence
Bottom temperature is unsuitable too high when evaporating operation, and bottom temperature should be controlled at 100 DEG C or so no more than 150 DEG C, typically.Send out in test
It is existing, although gasification temperature can be reduced using rectification under vacuum, it can be difficult to separating trans-decalin.
The content of the invention
In view of problem above, the present invention is devised and a kind of can separate the essentially identical bicyclic alkane of boiling point --- trans ten
The polynary entrainer of hydrogen naphthalene and polycyoalkane --- hanging type tetrahydrochysene dicyclopentadiene.In order to meet separating effect and rectification temperature simultaneously
Two kinds of restrictive conditions of degree, polynary entrainer is made up of water and the organic oxygen-containing compound with certain polarity.Due to the presence of water,
Rectification temperature is conducive to keeping the stability of hanging target product typically not over 100 DEG C, reduces its thermal condensation and generates colloid
Probability.And water is immiscible with bicyclic and polynaphthene hydrocarbon compound, thus overhead extraction liquid can be realized by point water
Oil-water separation, the oxygen-bearing organic matter in entrainer then can be separated by rectification under vacuum and recycled.
Concrete technical scheme of the present invention is as follows：
It is a kind of to separate bicyclic and polycyoalkane entrainer, by percentage to the quality, by the water and 10%- of 10%-90%
90% organic oxygen-containing compound composition.
The organic oxygen-containing compound be carbon three, carbon four, carbon five, the low-carbon (LC) alcohols of carbon six, furfuryl alcohol, tetrahydrofurfuryl alcohol, positive third
One or more in alcohol, n-butyl alcohol, cyclopentanol or dioxane.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 50%-70%'s
The n-butyl alcohol composition of water and 30%-50%.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 40%-70%'s
The cyclopentanol composition of water, the n-butyl alcohol of 20%-35% and 10%-25%.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 40%-70%'s
The cyclopentanol composition of water and 30%-60%.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 50%-70%'s
The tetrahydrofurfuryl alcohol composition of water and 30%-50%.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 30%-50%'s
The normal propyl alcohol composition of water and 50%-70%.
Preferably, described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by 30%-50%'s
The dioxane composition of water and 50%-70%.
Separate bicyclic and polycyoalkane entrainer and separate bicyclic and polycyoalkane method, bicyclic and polycyoalkane is mixed
Close, add and separate bicyclic and polycyoalkane entrainer, it is bicyclic and multi-ring to separate bicyclic and polycyoalkane entrainer consumption
0.1-5 times of paraffins mixture quality, distills on theoretical cam curve 30-200 rectifying column, and rectification pressure is 101KPa, is flowed back
Than 10:1 —50:1, tower top temperature is 80-105 DEG C, and column bottom temperature is 85-110 DEG C.
Preferably, described bicyclic and polycyoalkane the entrainer of separation separates bicyclic and polycyoalkane method, will be double
Ring and polycyoalkane mix, and add and separate bicyclic and polycyoalkane entrainer, separate bicyclic and polycyoalkane entrainer and use
Measure as bicyclic and polycyoalkane mixture quality 0.5-3 times, distillation, rectification pressure on theoretical cam curve 50-150 rectifying column
For 101KPa, reflux ratio 20:1—30:1, tower top temperature is 80-100 DEG C, and column bottom temperature is 90-105 DEG C.
It is described to separate bicyclic and polycyoalkane entrainer and be particularly suited for separating the almost identical trans-decalin of boiling point
And hanging type tetrahydrochysene dicyclopentadiene.
Beneficial effects of the present invention：Bicyclic alkane and polycyoalkane that boiling point is very close to, such as trans decahydro can be realized
Naphthalene and hanging type tetrahydrochysene dicyclopentadiene are efficiently separated, and can obtain higher separation accuracy.The polynary entrainer letter of the present invention
Singly it is easy to get, and due to the presence for having water so that distillation operation temperature is relatively low, such that it is able to avoid polycyoalkane at relatively high temperatures
Generation condensation reaction, while relatively low operation temperature also causes distillation operation easily controllable.
Description of the drawings
Fig. 1 is isomerization of bridge-type tetrahydro-dicyclopentadiene reaction.
Specific embodiment
The present invention is further illustrated with reference to the preferred embodiments of the present invention.
Embodiment 1
It is a kind of to separate bicyclic and polycyoalkane entrainer, by percentage to the quality, by the water and 10%- of 10%-90%
90% organic oxygen-containing compound composition.The organic oxygen-containing compound is carbon three, carbon four, carbon five, the low-carbon (LC) alcohols of carbon six, bran
One or more in alcohol, tetrahydrofurfuryl alcohol, normal propyl alcohol, n-butyl alcohol, cyclopentanol or dioxane.
Embodiment 2
Bicyclic and polycyoalkane the entrainer of described separation, by percentage to the quality, by 50%-70% water and
The n-butyl alcohol composition of 30%-50%.
Embodiment 3
Described bicyclic and polycyoalkane the entrainer of separation, by percentage to the quality, by the water of 40%-70%, 20%-
35% n-butyl alcohol and the cyclopentanol composition of 10%-25%.
Embodiment 4
Bicyclic and polycyoalkane the entrainer of described separation, by percentage to the quality, by 40%-70% water and
The cyclopentanol composition of 30%-60%.
Embodiment 5
Bicyclic and polycyoalkane the entrainer of described separation, by percentage to the quality, by 50%-70% water and
The tetrahydrofurfuryl alcohol composition of 30%-50%.
Embodiment 6
Bicyclic and polycyoalkane the entrainer of described separation, by percentage to the quality, by 30%-50% water and
The normal propyl alcohol composition of 50%-70%.
Embodiment 7
Bicyclic and polycyoalkane the entrainer of described separation, by percentage to the quality, by 30%-50% water and
The dioxane composition of 50%-70%.
Embodiment 8
Separate bicyclic and polycyoalkane entrainer and separate bicyclic and polycyoalkane method, bicyclic and polycyoalkane is mixed
Close, add and separate bicyclic and polycyoalkane entrainer, it is bicyclic and multi-ring to separate bicyclic and polycyoalkane entrainer consumption
0.1-5 times of paraffins mixture quality, distills on theoretical cam curve 30-200 rectifying column, and rectification pressure is 101KPa, is flowed back
Than 10:1—50:1, tower top temperature is 80-105 DEG C, and column bottom temperature is 85-110 DEG C.
Embodiment 9
Described bicyclic and polycyoalkane the entrainer of separation separates bicyclic and polycyoalkane method, will be bicyclic and multi-ring
Alkane mixes, and adds and separates bicyclic and polycyoalkane entrainer, and it is bicyclic to separate bicyclic and polycyoalkane entrainer consumption
And 0.5-3 times of polycyoalkane mixture quality, on theoretical cam curve 50-150 rectifying column distill, rectification pressure for
101KPa, reflux ratio 20:1—30:1, tower top temperature is 80-100 DEG C, and column bottom temperature is 90-105 DEG C.
Embodiment 10
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using n-butyl alcohol 810g and water 990g mixture as polynary entrainer, on the rectifying column of theoretical cam curve 120,
Control reflux ratio 25：1, tower top temperature is 90-96 DEG C, and column bottom temperature is 98-102 DEG C.The accumulation extraction of Jing chromatography tower top is anti-
Formula decahydronaphthalene and hanging type tetrahydrochysene dicyclopentadiene mixture 52g, wherein trans-decalin weight/mass percentage composition 45%.Bottom of towe liquid
Trans-decalin weight/mass percentage composition is 1.44%, and hanging type tetrahydrochysene dicyclopentadiene of the trans-decalin content less than 1.5% is returned
Yield is 93.2%.
Embodiment 11
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using n-butyl alcohol 350g, cyclopentanol 250g and water 600g mixture as polynary entrainer, in theoretical cam curve 120
Rectifying column on, control reflux ratio 30：1, tower top temperature is 92-97 DEG C, and column bottom temperature is 99-102 DEG C.Jing chromatography tower tops
Accumulation extraction trans-decalin and hanging type tetrahydrochysene dicyclopentadiene mixture 43g, wherein trans-decalin weight/mass percentage composition
55%.Bottom of towe liquid trans-decalin weight/mass percentage composition is 1.41%, hanging tetrahydrochysene of the trans-decalin content less than 1.5%
The dicyclopentadiene response rate is 93.8%.
Embodiment 12
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using cyclopentanol 450g and water 650g mixture as polynary entrainer, on the rectifying column of theoretical cam curve 120,
Control reflux ratio 25：1, tower top temperature is 95-98 DEG C, and column bottom temperature is 99-103 DEG C.The accumulation extraction of Jing chromatography tower top is anti-
Formula decahydronaphthalene and hanging type tetrahydrochysene dicyclopentadiene mixture 60g, wherein trans-decalin weight/mass percentage composition 39%.Bottom of towe liquid
Trans-decalin weight/mass percentage composition is 1.45%, and hanging type tetrahydrochysene dicyclopentadiene of the trans-decalin content less than 1.5% is returned
Yield is 91.6%.
Embodiment 13
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using tetrahydrofurfuryl alcohol 400g and water 600g mixture as polynary entrainer, in the rectifying column of theoretical cam curve 120
On, control reflux ratio 28：1, tower top temperature is 98-100 DEG C, and column bottom temperature is 99-105 DEG C.The accumulation of Jing chromatography tower top is adopted
Go out trans-decalin and hanging type tetrahydrochysene dicyclopentadiene mixture 55g, wherein trans-decalin weight/mass percentage composition 42%.Bottom of towe
Liquid trans-decalin weight/mass percentage composition is 1.47%, hanging tetrahydrochysene bicyclic penta two of the trans-decalin content less than 1.5%
The alkene response rate is 92.1%.
Embodiment 14
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using normal propyl alcohol 1200g and water 800g mixture as polynary entrainer, on the rectifying column of theoretical cam curve 120,
Control reflux ratio 25：1, tower top temperature is 82-87 DEG C, and column bottom temperature is 90-96 DEG C.The accumulation extraction of Jing chromatography tower top is trans
Decahydronaphthalene and hanging type tetrahydrochysene dicyclopentadiene mixture 65g, wherein trans-decalin weight/mass percentage composition 36%.Bottom of towe liquid is anti-
Formula decahydronaphthalene weight/mass percentage composition is 1.46%, and hanging type tetrahydrochysene dicyclopentadiene of the trans-decalin content less than 1.5% is reclaimed
Rate is 90.4%.
Embodiment 15
Trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin quality percentage are contained
Amount 3.33%.Using dioxane 1500g and water 700g mixture as polynary entrainer, in the rectifying column of theoretical cam curve 120
On, control reflux ratio 30：1, tower top temperature is 85-89 DEG C, and column bottom temperature is 92-97 DEG C.The accumulation extraction of Jing chromatography tower top
Trans-decalin and hanging type tetrahydrochysene dicyclopentadiene mixture 68g, wherein trans-decalin weight/mass percentage composition 35%.Tower bottom liquid
Body trans-decalin weight/mass percentage composition is 1.43%, hanging type tetrahydrochysene dicyclopentadiene of the trans-decalin content less than 1.5%
The response rate is 90.2%.
Contrast experiment：By trans-decalin 40g and hanging type tetrahydrochysene dicyclopentadiene 1160g mix homogeneously, trans-decalin
Weight/mass percentage composition 3.33%.On the rectifying column of theoretical cam curve 120, distillation operation pressure 6.7KPa, reflux ratio 30 are controlled：
1, tower top temperature is 78-80 DEG C, and column bottom temperature is 106-108 DEG C.Jing chromatography tower top accumulation extraction trans-decalin and extension
Formula tetrahydro-dicyclopentadiene mixture 800g, wherein trans-decalin weight/mass percentage composition 4.2%, bottom of towe liquid trans-decalin
Weight/mass percentage composition is 1.58%.
From above example, it is difficult to obtain trans-decalin weight/mass percentage composition less than 1.5% using rectification under vacuum
Hanging type tetrahydrochysene dicyclopentadiene product, and adopt the present invention polynary azeotropic distillation can obtain higher separation accuracy, it is trans
The hanging type tetrahydrochysene dicyclopentadiene response rate of the decahydro naphthalene content less than 1.5% is above 90%, and column bottom temperature is also below decompression essence
Evaporate, be conducive to keeping stablizing for polycyoalkane.
The above, only present pre-ferred embodiments, therefore can not according to this limit the scope of present invention enforcement, i.e., according to
Equivalence changes that the scope of the claims of the present invention and description are made and modification, all should still belong in the range of the present invention covers.
Claims (10)
- It is 1. a kind of to separate bicyclic and polycyoalkane entrainer, it is characterised in that：By percentage to the quality, by 10%-90%'s The organic oxygen-containing compound composition of water and 10%-90%.
- It is 2. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：The organic oxygen-containing Compound is carbon three, carbon four, carbon five, the low-carbon (LC) alcohols of carbon six, furfuryl alcohol, tetrahydrofurfuryl alcohol, normal propyl alcohol, n-butyl alcohol, cyclopentanol or dioxy One or more in six rings.
- It is 3. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the water of 50%-70% and the n-butyl alcohol of 30%-50%.
- It is 4. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the cyclopentanol of the water of 40%-70%, the n-butyl alcohol of 20%-35% and 10%-25%.
- It is 5. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the water of 40%-70% and the cyclopentanol of 30%-60%.
- It is 6. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the water of 50%-70% and the tetrahydrofurfuryl alcohol of 30%-50%.
- It is 7. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the water of 30%-50% and the normal propyl alcohol of 50%-70%.
- It is 8. according to claim 1 to separate bicyclic and polycyoalkane entrainer, it is characterised in that：With mass percent Meter, is made up of the water of 30%-50% and the dioxane of 50%-70%.
- 9. bicyclic and polycyoalkane method is separated with bicyclic and polycyoalkane the entrainer of separation described in claim 1, its It is characterised by：Bicyclic and polycyoalkane is mixed, is added and is separated bicyclic and polycyoalkane entrainer, separate bicyclic and polynaphthene The entrainer consumption of hydrocarbon is bicyclic and 0.1-5 times of polycyoalkane mixture quality, on theoretical cam curve 30-200 rectifying column Distillation, rectification pressure be 101KPa, reflux ratio 10:1—50:1, tower top temperature is 80-105 DEG C, and column bottom temperature is 85-110 DEG C.
- It is 10. according to claim 9 to separate bicyclic and polycyoalkane the method for bicyclic and polycyoalkane entrainer separation, It is characterized in that：Bicyclic and polycyoalkane is mixed, is added and is separated bicyclic and polycyoalkane entrainer, separated bicyclic and multi-ring The entrainer consumption of alkane is bicyclic and 0.5-3 times of polycyoalkane mixture quality, in theoretical cam curve 50-150 rectifying column Upper distillation, rectification pressure is 101KPa, reflux ratio 20:1—30:1, tower top temperature is 80-100 DEG C, and column bottom temperature is 90- 105℃。
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| CN201611227560.6A CN106673940B (en) | 2016-12-27 | 2016-12-27 | A method of it separating bicyclic and polycyoalkane entrainer and separates bicyclic and polycyoalkane with entrainer |
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| CN201611227560.6A CN106673940B (en) | 2016-12-27 | 2016-12-27 | A method of it separating bicyclic and polycyoalkane entrainer and separates bicyclic and polycyoalkane with entrainer |
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|---|---|---|---|---|
| US20010051755A1 (en) * | 2000-06-13 | 2001-12-13 | Takeshi Kawai | Process for producing adamantane |
| CN101081802A (en) * | 2007-05-30 | 2007-12-05 | 西安近代化学研究所 | Method for synthesizing hanger-type-tricycl [5.2.1.02,6] decane |
| CN101215218A (en) * | 2008-01-16 | 2008-07-09 | 西安近代化学研究所 | Method for preparing exo-tetrahydrocyclopentadiene |
| CN104130095A (en) * | 2014-08-04 | 2014-11-05 | 西安近代化学研究所 | Cis-decahydronaphthalene and trans-decahydronaphthalene separating method |
| 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 |
-
2016
- 2016-12-27 CN CN201611227560.6A patent/CN106673940B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010051755A1 (en) * | 2000-06-13 | 2001-12-13 | Takeshi Kawai | Process for producing adamantane |
| CN101081802A (en) * | 2007-05-30 | 2007-12-05 | 西安近代化学研究所 | Method for synthesizing hanger-type-tricycl [5.2.1.02,6] decane |
| CN101215218A (en) * | 2008-01-16 | 2008-07-09 | 西安近代化学研究所 | Method for preparing exo-tetrahydrocyclopentadiene |
| CN104130095A (en) * | 2014-08-04 | 2014-11-05 | 西安近代化学研究所 | Cis-decahydronaphthalene and trans-decahydronaphthalene separating method |
| 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 |
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| Title |
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| 杜咏梅 等: "高密度烃燃料挂式四氢双环戊二烯的研究进展", 《火炸药学报》 * |
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