CN106866431B - A kind of production method of N- (2- methoxycyclohexyls) -1,3- propane diamine - Google Patents
A kind of production method of N- (2- methoxycyclohexyls) -1,3- propane diamine Download PDFInfo
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- CN106866431B CN106866431B CN201710095091.5A CN201710095091A CN106866431B CN 106866431 B CN106866431 B CN 106866431B CN 201710095091 A CN201710095091 A CN 201710095091A CN 106866431 B CN106866431 B CN 106866431B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a kind of production methods of 1,3 propane diamine of synthesis of compound, separation method, in particular to a kind of N (2 methoxycyclohexyl).The present invention is using 3 (2 methoxycyclohexyl) aminopropionitriles as raw material, it is hydrogenated to synthesize and through detaching what is removed the low-boiling-point substances such as incoagulable gas and water and come, then feed separation is carried out through different knockout towers, obtain the higher product of purity, it is an advantage of the invention that the N (2 methoxycyclohexyl) 1 of high-quality is obtained, 3 propane diamine products, and various materials have obtained fully, effectively utilizing.This method separation process is concise, and energy consumption, consumption of raw materials are low, and the good product quality rate of recovery is high, and production cost is low.
Description
Technical field
The present invention relates to a kind of synthesis of compound, separation method, in particular to a kind of N- (2- methoxycyclohexyls) -1,
The separation method of 3- propane diamine.
Background technology
N- (2- methoxycyclohexyls) -1,3- propane diamine is a kind of important organic chemical industry's intermediate, as epoxy resin
Curing agent and modified firming agent raw material, be also used as polymerization auxiliary agent and rubber additive, also can be used as production medicine,
The intermediate of pesticide.Molecular formula：C10H22N2O, molecular weight：186.29.As a kind of novel organic chemical industry's intermediate, it is given birth to
Production (synthesis, separation) method existing literature is not also related to and is reported.
Invention content
The present inventor completes the present invention by a large amount of research work.
The object of the present invention is to provide a kind of flow advantages of simple, and production cost is low, good product quality, are suitble to industrial production
N- (2- methoxycyclohexyls) -1,3- propane diamine continuous production method.
The continuous production method of N- (2- methoxycyclohexyls) -1,3- propane diamine be with 3- (2- methoxycyclohexyls) -
Aminopropionitrile is raw material, hydrogenated to synthesize and through detaching what is removed the low-boiling-point substances such as incoagulable gas and water and come, i.e., institute of the present invention
For N- (2- methoxycyclohexyls) -1,3- propane diamine synthetic routes be 3- (2- methoxycyclohexyls)-aminopropionitrile route,
Part 2- methoxycyclohexyls amine and a small amount of can be contained in its raw material 3- (2- methoxycyclohexyls)-aminopropionitrile material system
Organic compound containing unsaturated bonds such as-C=C- ,-C ≡ C- ,-C ≡ N.
It can be methanol, 1,3- propane diamine and raw material to intend other impurities in the mixture A of separation in above-mentioned technical proposal
The medium substance come containing organic compound hydrogenation reactions of unsaturated bonds such as-C=C- ,-C ≡ C- ,-C ≡ N.
The present invention is to solve its technical problem by following technical proposals：
A kind of production method of N- (2- methoxycyclohexyls) -1,3- propane diamine, it is characterised in that include the following steps：
(1) using 3- (2- methoxycyclohexyls)-aminopropionitrile as raw material, the mixture obtained by hydrogenated synthesis；It will be above-mentioned
Mixture enters the separation of lighter component knockout tower, from low boilings impurity such as overhead extraction cyclohexyl methyl ether, 1,3- propane diamine, first containing 2-
Oxygroup cyclohexylamine, N- cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls
Base) mixtures of a small amount of high-boiling components such as-aminopropionitrile enters in the middle part of methoxycyclohexyl amine recovery tower from tower reactor and detached；
(2) into the material of methoxycyclohexyl amine recovery tower, through separation, from overhead extraction 2- methoxycyclohexyl amine products,
- the 1,3- of cyclohexyl containing N- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropan
The mixture of a small amount of high-boiling components such as nitrile enters product knockout tower from middle part；
(3) into the material of product knockout tower, after separation, from overhead extraction N- (2- methoxycyclohexyls) -1,3- third
Two amine products, tower reactor are the high-boiling components containing a small amount of N- (2- methoxycyclohexyls) -1,3- propane diamine products；Wherein product detaches
The number of plates of tower is 40~60 pieces, and rectifying section is 15~35 blocks of column plates, and tower top temperature is 100~160 DEG C, bottom temperature 120
~180 DEG C, tower top pressure -0.0998MPa<P≤0MPa, overhead reflux liquid reflux ratio are 4~10；
Preferably, N- (2- methoxycyclohexyls) -1,3- propane diamine product knockout towers described in aforementioned production method
Tower top pressure is -0.0998MPa<P≤-0.09MPa.It is due to N- (2- methoxycyclohexyls) -1,3- propane diamine product itselfs
The reason of physical property, the variation shown to pressure-temperature is more sensitive, since compound composition generated in organic reaction is answered
It is miscellaneous, so choosing the operating conditions such as accurate temperature, pressure, good separating effect can be not only obtained, it can also realization
Learn the suitable control of byproduct of reaction；So seem extremely important for controls such as pressure herein.
Preferably, the methoxycyclohexyl amine recovery tower described in aforementioned production method is vacuumizing, it is due to mixing
The reason of physical property of objects system substance itself, the variation shown to pressure-temperature is more sensitive, even if relatively low in pressure thus
In the case of, with.
Preferably, separation process system carries out closed cycle in aforementioned production method, Matter Transfer utilizes.
Preferably, lighter component knockout tower described in aforementioned production method, methoxycyclohexyl amine recovery tower, product knockout tower
Using calendering acanthopore mellapak packing tower, the feed rate of each tower is controlled in 4000 kgs/hr of every square metre of tower sections
Within product.
Preferably, entering in the mixture of methoxycyclohexyl amine tower in step (2) in aforementioned production method, do not include
The low-boiling-point substance mass content of 2- methoxycyclohexyl amine is controlled within 0.05%.
Preferably, enter in the material of product knockout tower in step (3) in aforementioned production method, cyclohexyl containing N- -1,
3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropionitrile high-boiling components mix
The mass content for closing object is controlled more than 99.5%.
In this application, due to certainly existing the by-products such as some incomplete reactants in organic synthesis, so will
Containing cyclohexyl methyl ether, propylamine, 2- methoxycyclohexyls amine, N- cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -
The high-boiling components such as 1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropionitrile and the mixture of a small amount of other impurities (referred to as mix
Object A) into lighter component knockout tower middle part, through separation, from low boilings impurity such as overhead extraction cyclohexyl methyl ether, propylamine；First containing 2-
Oxygroup cyclohexylamine, N- cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls
Base) mixtures (abbreviation mixture B) of a small amount of high-boiling components such as-aminopropionitrile enters in the middle part of methoxycyclohexyl amine tower from tower reactor and carries out
Separation, at this time low-boiling-point substance≤0.05% before 2- methoxycyclohexyls amine (not including) in mixture B under normal circumstances.Through detaching,
From the 2- methoxycyclohexyl amine of more than 99.5% overhead extraction content, cyclohexyl containing N- -1,3- propane diamine, N- (2- methoxy basic rings
Hexyl) a small amount of high-boiling components such as -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropionitrile mixture (abbreviation mixture C)
Into product knockout tower, 2- methoxycyclohexyls amine content≤0.5% in mixture C at this time；Mixture C is through separation, from product tower
N- (2- methoxycyclohexyls) -1,3- propane diamine products that top extraction content is more than 99.5%, tower reactor is high-boiling components.Entire point
Three low boiling impurity knockout tower, methoxycyclohexyl amine tower, product knockout tower knockout towers are shared from flow, and the form of knockout tower can be with
It is valve tower, bubble column, packed tower, but is best, feed rate≤4,000,000 of each tower to roll acanthopore mellapak packing tower
Gram/(every square metre of tower section product of hour).Wherein the number of plates of product knockout tower is 40~60 pieces, and rectifying section is 15~35 pieces
Column plate, tower top temperature are 100~160 DEG C, and bottom temperature is 120~180 DEG C, and tower top pressure is less than or equal to more than -0.0998
0MPa, overhead reflux liquid reflux ratio are 4~10.In this application, the low-boiling-point substance, high-boiling components are known normal in industry
Know, so no longer enumerating formula explanation to this.
The invention has the advantages that：N- (2- methoxycyclohexyls) -1,3- propane diamine products of high-quality have been obtained, and
And various materials have obtained fully, effectively utilizing.This method separation process is concise, and energy consumption, consumption of raw materials are low, good product quality
The rate of recovery is high, and production cost is low.
Specific embodiment
The implementation of the present invention is illustrated below：
Embodiment 1：
A kind of production method of N- (2- methoxycyclohexyls) -1,3- propane diamine, includes the following steps：
(1) using 3- (2- methoxycyclohexyls)-aminopropionitrile as raw material, the mixture obtained by hydrogenated synthesis；It will be above-mentioned
Mixture enters the separation of lighter component knockout tower, from low boilings impurity such as overhead extraction cyclohexyl methyl ether, 1,3- propane diamine, first containing 2-
Oxygroup cyclohexylamine, N- cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls
Base) mixtures of a small amount of high-boiling components such as-aminopropionitrile enters in the middle part of methoxycyclohexyl amine recovery tower from tower reactor and detached；
(2) into the material of methoxycyclohexyl amine recovery tower, through separation, from overhead extraction 2- methoxycyclohexyl amine products,
- the 1,3- of cyclohexyl containing N- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropan
The mixture of a small amount of high-boiling components such as nitrile enters product knockout tower from middle part；
(3) into the material of product knockout tower, after separation, from overhead extraction N- (2- methoxycyclohexyls) -1,3- third
Two amine products, tower reactor are the high-boiling components containing a small amount of N- (2- methoxycyclohexyls) -1,3- propane diamine products；Wherein product detaches
The number of plates of tower is 40~60 pieces, and rectifying section is 15~35 blocks of column plates, and tower top temperature is 100~160 DEG C, bottom temperature 120
~180 DEG C, tower top pressure -0.0998MPa<P≤0MPa, overhead reflux liquid reflux ratio are 4~10；
In the present embodiment, mixture A enters the piece-rate system of tower a diameter of 100 with about 50 kgs/hr of flow, this is mixed
The weight composition for closing each component in object is as follows：Cyclohexyl methyl ether 1.1%, 1,3- propane diamine 0.7%, other lighter components
1.65%th, 2- methoxycyclohexyls amine 15.95%, N- cyclohexyl -1,3- propane diamine 0.1%, N- (2- methoxycyclohexyls) -1,3-
Propane diamine 78.79%, 3- (2- methoxycyclohexyls)-aminopropionitriles and high-boiling components 1.71%.Mixture A is detached through lighter component
The lighter components such as tower separation tower top removal cyclohexyl methyl ether, 1,3- propane diamine, kettle material mixture B is through methoxycyclohexyl amine tower
Separation, the 2- methoxycyclohexyl amine of more than 99.5% overhead extraction, kettle material is mixture C.The weight of each component in mixture C
Amount composition is as follows：2- methoxycyclohexyls amine 0.25%, N- cyclohexyl -1,3- propane diamine 0.09%, N- (2- methoxycyclohexyls) -
1,3- propane diamine 97.55%, 3- (2- methoxycyclohexyls)-aminopropionitriles and high-boiling components 2.11%.The mixture C enters product
In the middle part of knockout tower, 40.385 kgs/hr of flow, product knockout tower is calendering acanthopore mellapak packing tower, shares 55 pieces of column plate.
Wherein 32 pieces of rectifying section, tower top pressure are -0.0995MPa, and tower top temperature is 110 DEG C, and bottom temperature is 124 DEG C, overhead reflux
Liquid reflux ratio is 4.Product knockout tower overhead extraction mass flow is 39.475 kgs/hr, wherein N- (2- methoxycyclohexyls
Base) -1,3- propane diamine mass content be 99.59%, high-boiling components 0.06%；Product knockout tower bottom of towe produces mass flow
0.91 kg/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 8.79%.
Embodiment 2：
By the condition and step of embodiment 1, change product knockout tower tower top pressure as -0.097MPa, tower top temperature 144
DEG C, bottom temperature is 160 DEG C, and overhead reflux liquid reflux ratio is 4.Product knockout tower overhead extraction mass flow for 39.5 kilograms/
Hour, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 99.53%, high-boiling components 0.13%；Product point
It it is 0.885 kg/hr from tower bottom of towe extraction mass flow, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine quality contains
Measure is 9.04%.
Embodiment 3：
By the condition and step of embodiment 1, it is -0.092MPa only to change product knockout tower tower top pressure, and tower top temperature is
170 DEG C, bottom temperature is 190 DEG C, and overhead reflux liquid reflux ratio is 4.Product knockout tower overhead extraction mass flow is 39.435
Kg/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 99.28%, high-boiling components 0.38%；
Product knockout tower bottom of towe extraction mass flow is 1.9 kgs/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine matter
It is 25.79% to measure content.
Embodiment 4：
By the condition and step of embodiment 1, it is -0.092MPa only to change product knockout tower tower top pressure, and tower top temperature is
170 DEG C, bottom temperature is 190 DEG C, and overhead reflux liquid reflux ratio is 10.Product knockout tower overhead extraction mass flow is 39.49
Kg/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 99.52%, high-boiling components 0.14%；
Product knockout tower bottom of towe extraction mass flow is 0.995 kg/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine
Mass content is 24.62%.
Embodiment 5：
By the condition and step of embodiment 1, only change product knockout tower tower height degree, total 48 pieces of number of plates.Wherein rectifying section
28 pieces.Product knockout tower overhead extraction mass flow is 39.42 kgs/hr, wherein N- (2- methoxycyclohexyls) -1,3- third
Diamines mass content is 99.51%, high-boiling components 0.49%；Product knockout tower bottom of towe extraction mass flow for 0.965 kilogram/it is small
When, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 17.62%.
Embodiment 6：
By the condition and step of embodiment 1, change product knockout tower tower top pressure as -0.092MPa, tower top temperature 170
DEG C, bottom temperature be 190 DEG C, overhead reflux liquid reflux ratio be 10, methoxycyclohexyl amine recovery tower be vacuumizing, separation process
System carries out closed cycle, and Matter Transfer utilizes, and enters in the mixture of methoxycyclohexyl amine tower in step (2), not comprising 2-
The low-boiling-point substance mass content of methoxycyclohexyl amine is controlled within 0.05%.Product knockout tower overhead extraction mass flow is
39.49 kgs/hr, wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 99.52%, and high-boiling components are
0.14%；Product knockout tower bottom of towe extraction mass flow is 0.995 kg/hr, wherein N- (2- methoxycyclohexyls) -1,3-
Propane diamine mass content is 23.78%.
Embodiment 7：
By the condition and step of embodiment 6, change product knockout tower tower top pressure as -0.092MPa, tower top temperature 170
DEG C, bottom temperature be 190 DEG C, overhead reflux liquid reflux ratio be 10, methoxycyclohexyl amine recovery tower be vacuumizing, separation process
System carries out closed cycle, and Matter Transfer utilizes, and enters in the material of product knockout tower in step (3), cyclohexyl containing N- -1,
3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropionitrile high-boiling components mix
The mass content for closing object is controlled more than 99.5%.Product knockout tower overhead extraction mass flow is 39.49 kgs/hr,
Middle N- (2- methoxycyclohexyls) -1,3- propane diamine mass content is 99.52%, high-boiling components 0.14%；Product knockout tower tower
Bottom extraction mass flow is 0.995 kg/hr, and wherein N- (2- methoxycyclohexyls) -1,3- propane diamine mass contents are
24.12%.
The present invention be suitable for 3- (2- methoxycyclohexyls)-aminopropionitrile hydrogenation method route N- (2- methoxycyclohexyls)-
The separating-purifying of 1,3- propane diamine but it is not limited to 3- (2- methoxycyclohexyls)-aminopropionitrile hydrogenation method route N- (2- methoxies
Butylcyclohexyl) -1,3- propane diamine separation, be equally applicable to other and finally add through 3- (2- methoxycyclohexyls)-aminopropionitrile
The separation of N- (2- methoxycyclohexyls) -1,3- propane diamine of hydrogen synthetic route, reference the method for the invention, by adjusting,
Changing the partial parameters in operating condition of the present invention can realize other finally through 3- (2- methoxycyclohexyls)-aminopropionitrile
The separation of N- (2- methoxycyclohexyls) -1,3- propane diamine of hydrogenation synthesis route.
For those skilled in the art, it is aobvious that the present invention, which carries out various modifications and variations (variation of material content),
And it is clear to, and be construed as such modifications and variations all within the scope of this specification, also appended claim
Spirit and scope within.
Claims (6)
1. a kind of production method of N- (2- methoxycyclohexyls) -1,3- propane diamine, it is characterised in that include the following steps：
(1) using 3- (2- methoxycyclohexyls)-aminopropionitrile as raw material, the mixture obtained by hydrogenated synthesis；By above-mentioned mixing
Object enters the separation of lighter component knockout tower, from low boilings impurity such as overhead extraction cyclohexyl methyl ether, 1,3- propane diamine, methoxyl group containing 2-
Cyclohexylamine, N- cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls) -
The mixture of a small amount of high-boiling components such as aminopropionitrile, which enters from tower reactor in the middle part of methoxycyclohexyl amine recovery tower, to be detached；
(2) into the material of methoxycyclohexyl amine recovery tower, through separation, from overhead extraction 2- methoxycyclohexyl amine products, containing N-
Cyclohexyl -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- propane diamine, 3- (2- methoxycyclohexyls)-aminopropionitrile etc.
The mixture of a small amount of high-boiling components enters product knockout tower from middle part；
(3) into the material of product knockout tower, after separation, from overhead extraction N- (2- methoxycyclohexyls) -1,3- propane diamine
Product, tower reactor are the high-boiling components containing a small amount of N- (2- methoxycyclohexyls) -1,3- propane diamine products；Wherein product knockout tower
The number of plates is 40~60 pieces, and rectifying section is 15~35 blocks of column plates, and tower top temperature is 100~160 DEG C, and bottom temperature is 120~180
DEG C, tower top pressure -0.0998MPa<P≤0MPa, overhead reflux liquid reflux ratio are 4~10；
2. the production method of N- (2- methoxycyclohexyls) -1,3- propane diamine according to claim 1, it is characterised in that institute
N- (2- the methoxycyclohexyls) -1,3- propane diamine product knockout towers tower top pressure stated is -0.0998MPa<P≤-0.09MPa.
3. the production method of N- (2- methoxycyclohexyls) -1,3- propane diamine according to claim 1, it is characterised in that institute
The methoxycyclohexyl amine recovery tower stated is vacuumizing.
4. the production method of N- (2- methoxycyclohexyls) -1,3- propane diamine according to claim 1, it is characterised in that institute
The separation process system stated carries out closed cycle, and Matter Transfer utilizes.
5. the production method of N- (2- methoxycyclohexyls) -1,3- propane diamine according to claim 1, it is characterised in that institute
It states lighter component knockout tower, methoxycyclohexyl amine recovery tower, product knockout tower and uses calendering acanthopore mellapak packing tower, each tower
Feed rate control is within 4000 kgs/hr of every square metre of tower sections accumulate.
6. the production method of N- (2- methoxycyclohexyls) -1,3- propane diamine according to claim 1, it is characterised in that step
Suddenly enter in the material of product knockout tower in (3), cyclohexyl containing N- -1,3- propane diamine, N- (2- methoxycyclohexyls) -1,3- third
Diamines, 3- (2- methoxycyclohexyls)-aminopropionitrile high-boiling components mixture mass content control more than 99.5%.
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| CN109725070B (en) * | 2017-10-31 | 2022-05-10 | 浙江新化化工股份有限公司 | Method for measuring content of N- (2-methoxycyclohexyl) -1,3-propane diamine |
| CN115108924A (en) * | 2022-06-24 | 2022-09-27 | 岳阳昌德新材料有限公司 | Amine intermediate and preparation method and application thereof |
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| CN1365965A (en) * | 2001-01-05 | 2002-08-28 | 巴斯福股份公司 | Method of preparing primary amine and secondary amine from nitrile |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1365965A (en) * | 2001-01-05 | 2002-08-28 | 巴斯福股份公司 | Method of preparing primary amine and secondary amine from nitrile |
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