CN104151127A - Method for synthesizing pinane through alpha-pinene hydrogenation - Google Patents
Method for synthesizing pinane through alpha-pinene hydrogenation Download PDFInfo
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- CN104151127A CN104151127A CN201410396832.XA CN201410396832A CN104151127A CN 104151127 A CN104151127 A CN 104151127A CN 201410396832 A CN201410396832 A CN 201410396832A CN 104151127 A CN104151127 A CN 104151127A
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Abstract
The invention discloses a method for synthesizing pinane through alpha-pinene hydrogenation, and relates to the technical field of terpenoid compound deep processing. According to the invention, reaction temperatures and hydrogenation pressures of various different alpha-pinene content stages of an alpha-pinene hydrogenation synthesis reaction process are subjected to corresponding adjustments and control, such that the reaction is mild and ordered, and is oriented to high yield of cis-structured pinane. Therefore, a purpose of improving cis-structured pinane content can be achieved.
Description
Technical field
The invention belongs to terpenoid deep process technology field, relate in particular to a kind of method of α-pinene hydrogenation synthesizing pinane.
Background technology
Along with China is to utilizing turps to extract going deep into of compound essence research, the research of α-pinene gets most of the attention more.Wherein, pinane is one of large deep processed product of α-pinene, and it is also synthetic senior spices and vitamin A, E, one of raw material of K.By pinane during for the synthesis of derived product, basic what utilize is the pinane of cis-structure.
Yet according to the existing pinane product that the technology of α-pinene hydrogenation synthesizing pinane is obtained, the pinane content of its cis-structure is only generally 80%～85%, thereby the following process that has increased pinane product is utilized cost.
Summary of the invention
A kind of method that the object of this invention is to provide α-pinene hydrogenation synthesizing pinane, the pinane content that the method can solve cis-structure in the pinane product making because of prior art is only generally 80%～85%, thereby the following process that has increased pinane product is utilized the problem of cost.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is:
It comprises the following steps:
A, α-pinene content is greater than to 93% α-pinene mixture and nickel catalyzator puts into reactor, pass into hydrogen, hydrogen pressure in control reactor is in the scope of 0.05MPa～0.10MPa, then start heating, make the temperature of reaction mass in reactor reach 120 ℃～130 ℃, carry out pressure-maintaining and heat-preservation reaction; Wherein, described α-pinene mixture and nickel catalyzator mass ratio are 1:0.005～0.02;
B, in reactor, in reaction mass during content≤60% of α-pinene, regulate hydrogen pressure to 0.1MPa～0.16MPa, control the temperature to 130 ℃ of reaction mass～140 ℃, carry out pressure-maintaining and heat-preservation reaction;
C, in reactor, in reaction mass during content≤30% of α-pinene, regulate hydrogen pressure to 0.16MPa～0.24MPa, control the temperature to 140 ℃ of reaction mass～150 ℃, carry out pressure-maintaining and heat-preservation reaction;
D, in reactor, in reaction mass during content≤10% of α-pinene, regulate hydrogen pressure to 0.24MPa～0.32MPa, control the temperature to 150 ℃ of reaction mass～160 ℃, carry out pressure-maintaining and heat-preservation reaction;
E, in reactor, in reaction mass during content≤1% of α-pinene, stop adding hydrogen in reactor, and stop heating, cooling after, discharging.
Owing to adopting technique scheme, the beneficial effect that the present invention obtains is:
The present invention is by carrying out the corresponding control that regulates to the temperature of reaction in a plurality of different α-pinene content stages of α-pinene hydrogenation synthesizing reaction process and hydrogenation pressure, thereby make reaction temperature and orderly carrying out towards the high direction of the pinane yield of cis-structure, to reach the high object of pinane content that improves cis-structure.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, and protection scope of the present invention is not only confined to following examples.
Embodiment 1
The method of this α-pinene hydrogenation synthesizing pinane comprises the following steps:
A, the α-pinene mixture and the 0.4g nickel catalyzator that by the content of 80g α-pinene, are 95.1% are put into reactor, first use nitrogen replacement three times, use again hydrogen exchange three times, then pass into hydrogen, then control hydrogen pressure in reactor in the scope of 0.1MPa, then start heating, make the temperature of reaction mass in reactor reach 120 ℃, carry out pressure-maintaining and heat-preservation reaction;
B, in reactor, in reaction mass during content≤60% of α-pinene, regulate hydrogen pressure to 0.16MPa, control the temperature to 130 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
C, in reactor, in reaction mass during content≤30% of α-pinene, regulate hydrogen pressure to 0.24MPa, control the temperature to 140 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
D, in reactor, in reaction mass during content≤10% of α-pinene, regulate hydrogen pressure to 0.32MPa, control the temperature to 150 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
E, in reactor, in reaction mass during content≤1% of α-pinene, stop adding hydrogen in reactor, and stop heating, open below cooling water temperature to 40 ℃ discharging.
The pinane product that the present embodiment is made carries out product analysis and obtains: cis-pinane content is: 93.4%, and α-pinene content is: 0.6%, transformation efficiency is 99.4%, cis-pinane selectivity is: 98.8%.
Embodiment 2
The method of this α-pinene hydrogenation synthesizing pinane comprises the following steps:
A, the α-pinene mixture and the 4g nickel catalyzator that by the content of 400g α-pinene, are 96.1% are put into reactor, first use nitrogen replacement three times, use again hydrogen exchange three times, then pass into hydrogen, then control hydrogen pressure in reactor in the scope of 0.08MPa, then start heating, make the temperature of reaction mass in reactor reach 125 ℃, carry out pressure-maintaining and heat-preservation reaction;
B, in reactor, in reaction mass during content≤60% of α-pinene, regulate hydrogen pressure to 0.13MPa, control the temperature to 135 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
C, in reactor, in reaction mass during content≤30% of α-pinene, regulate hydrogen pressure to 0.2MPa, control the temperature to 145 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
D, in reactor, in reaction mass during content≤10% of α-pinene, regulate hydrogen pressure to 0.28MPa, control the temperature to 155 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
E, in reactor, in reaction mass during content≤1% of α-pinene, stop adding hydrogen in reactor, control the reaction mass heating in reactor, then open below cooling water temperature to 40 ℃ discharging.
The pinane product that the present embodiment is made carries out product analysis and obtains: cis-pinane content is: 93.3%, and α-pinene content is: 0.7%, transformation efficiency is 99.3%, cis-pinane selectivity is: 97.8%.
Embodiment 3
The method of this α-pinene hydrogenation synthesizing pinane comprises the following steps:
A, the α-pinene mixture and the 24g nickel catalyzator that by the content of 1200g α-pinene, are 95.8% are put into reactor, first use nitrogen replacement three times, use again hydrogen exchange three times, then pass into hydrogen, then control hydrogen pressure in reactor in the scope of 0.05MPa, then start heating, make the temperature of reaction mass in reactor reach 130 ℃, carry out pressure-maintaining and heat-preservation reaction;
B, in reactor, in reaction mass during content≤60% of α-pinene, regulate hydrogen pressure to 0.1MPa, control the temperature to 140 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
C, in reactor, in reaction mass during content≤30% of α-pinene, regulate hydrogen pressure to 0.16MPa, control the temperature to 150 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
D, in reactor, in reaction mass during content≤10% of α-pinene, regulate hydrogen pressure to 0.24MPa, control the temperature to 160 ℃ of reaction mass, carry out pressure-maintaining and heat-preservation reaction;
E, in reactor, in reaction mass during content≤1% of α-pinene, stop adding hydrogen in reactor, control the reaction mass heating in reactor, then open below cooling water temperature to 40 ℃ discharging.
The pinane product that the present embodiment is made carries out product analysis and obtains: cis-pinane content is: 93.2%, and α-pinene content is: 0.8%, transformation efficiency is 99.2%, cis-pinane selectivity is: 98.1%.
Claims (1)
1. a method for α-pinene hydrogenation synthesizing pinane, is characterized in that comprising the following steps:
A, α-pinene content is greater than to 93% α-pinene mixture and nickel catalyzator puts into reactor, pass into hydrogen, hydrogen pressure in control reactor is in the scope of 0.05MPa～0.10MPa, then start heating, make the temperature of reaction mass in reactor reach 120 ℃～130 ℃, carry out pressure-maintaining and heat-preservation reaction; Wherein, described α-pinene mixture and nickel catalyzator mass ratio are 1:0.005～0.02;
B, in reactor, in reaction mass during content≤60% of α-pinene, regulate hydrogen pressure to 0.1MPa～0.16MPa, control the temperature to 130 ℃ of reaction mass～140 ℃, carry out pressure-maintaining and heat-preservation reaction;
C, in reactor, in reaction mass during content≤30% of α-pinene, regulate hydrogen pressure to 0.16MPa～0.24MPa, control the temperature to 140 ℃ of reaction mass～150 ℃, carry out pressure-maintaining and heat-preservation reaction;
D, in reactor, in reaction mass during content≤10% of α-pinene, regulate hydrogen pressure to 0.24MPa～0.32MPa, control the temperature to 150 ℃ of reaction mass～160 ℃, carry out pressure-maintaining and heat-preservation reaction;
E, in reactor, in reaction mass during content≤1% of α-pinene, stop adding hydrogen in reactor, and stop heating, cooling after, discharging.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201410396832.XA CN104151127A (en) | 2014-08-13 | 2014-08-13 | Method for synthesizing pinane through alpha-pinene hydrogenation |
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| CN201410396832.XA CN104151127A (en) | 2014-08-13 | 2014-08-13 | Method for synthesizing pinane through alpha-pinene hydrogenation |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108101728A (en) * | 2018-01-31 | 2018-06-01 | 梧州学院 | A kind of preparation method to Meng's alkane |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072508A1 (en) * | 2001-03-09 | 2002-09-19 | Valtion Teknillinen Tutkimuskeskus | HYDROGENATION OF α-PINENE |
| CN101884925A (en) * | 2010-07-09 | 2010-11-17 | 桂林理工大学 | Catalyst for synthesizing pinane by hydrogenating alpha-pinene and preparation method |
| CN101962310A (en) * | 2010-09-19 | 2011-02-02 | 湖南松源化工有限公司 | Method for continuously producing pinane by pinene and device therefor |
| CN102125864A (en) * | 2010-12-16 | 2011-07-20 | 昆明理工大学 | Supported catalyst for hydrogenation of alpha-pinene and preparation method and uses thereof |
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- 2014-08-13 CN CN201410396832.XA patent/CN104151127A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072508A1 (en) * | 2001-03-09 | 2002-09-19 | Valtion Teknillinen Tutkimuskeskus | HYDROGENATION OF α-PINENE |
| CN101884925A (en) * | 2010-07-09 | 2010-11-17 | 桂林理工大学 | Catalyst for synthesizing pinane by hydrogenating alpha-pinene and preparation method |
| CN101962310A (en) * | 2010-09-19 | 2011-02-02 | 湖南松源化工有限公司 | Method for continuously producing pinane by pinene and device therefor |
| CN102125864A (en) * | 2010-12-16 | 2011-07-20 | 昆明理工大学 | Supported catalyst for hydrogenation of alpha-pinene and preparation method and uses thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108101728A (en) * | 2018-01-31 | 2018-06-01 | 梧州学院 | A kind of preparation method to Meng's alkane |
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Application publication date: 20141119 |