CN107556197A - A kind of preparation method of tri-iso-octylamine - Google Patents
A kind of preparation method of tri-iso-octylamine Download PDFInfo
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- CN107556197A CN107556197A CN201710679056.8A CN201710679056A CN107556197A CN 107556197 A CN107556197 A CN 107556197A CN 201710679056 A CN201710679056 A CN 201710679056A CN 107556197 A CN107556197 A CN 107556197A
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- iso
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- octylamine
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- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006073 displacement reaction Methods 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 12
- 239000012043 crude product Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 claims description 3
- 229960001465 octodrine Drugs 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 229960004643 cupric oxide Drugs 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical group [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 2
- 239000000395 magnesium oxide Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 description 14
- 239000010949 copper Substances 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 238000009434 installation Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 241001550224 Apha Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a kind of preparation method of tri-iso-octylamine, its preparation process is：By two octodrines and the catalyst reduction reaction between 180 230 DEG C after nitrogen displacement, hydrogen displacement, isooctanol, hydrogen circulation is then added dropwise, after heating response, substantially not water outlet, tri-iso-octylamine crude product is obtained, again through rectifying, product is obtained, product content is more than 98Wt.%.A small amount of unreacted isooctanol can be with recycled, and simple to operate, non-corrosiveness or pungent produce in production process, thus will not corrode production equipment and generation environment pollution.The present invention uses catalyst to have higher activity, selectivity and stability and post-processed simply, and catalyst is reusable to be easily achieved industrialization.For the high conversion rate of isooctanol up to 89.5%, product selectivity is up to 81.3%.
Description
Technical field
The invention belongs to organic synthesis field, and in particular to a kind of preparation method of tri-iso-octylamine.
Background technology
Tri-iso-octylamine (Tris (2-ethylhexyl) amine) is a kind of special secondary amine class product, is colourless to yellow
There are the liquid compound of amine taste, chemical formula C24H51N.No. CAS is 1860-26-0, molecular weight 353.6684, alkalescent, density
(g/mL,25/4℃)：0.816, -94 DEG C of fusing point, boiling point:334.8 DEG C of at 1013.25hPa, flash-point:162℃at
1013.25hPa refractive index:n20/D 1.4501(lit.).It is not soluble in water, it is dissolved in ethanol and ether.
Purposes：Extractant, sheet processing auxiliary agent, powdery paints.
The synthesis main route of tri-iso-octylamine at present：
Tri-iso-octylamine crude product is generated under catalyst action in autoclave using different octanal and two octodrines, passes through rectifying
Obtain product.Major drawbacks are that the different octanal of raw material is not easy to obtain, and price is high, is unfavorable for industrialized production.
The content of the invention
The technical problem to be solved in the present invention is：Solve the deficiencies in the prior art, there is provided a kind of raw material is easily obtained different
The method that octanol synthesizes tri-iso-octylamine.
In order to solve the above technical problems, the technical solution adopted by the present invention is：A kind of method prepared by tri-iso-octylamine, it is made
Standby step includes：By in two octodrines, catalyst input reactor, nitrogen displacement, after hydrogen displacement, gone back between 180-230 DEG C
2 ± 1h of raw catalyst, isooctanol is then added dropwise, the wherein dosage of catalyst is the 0.5%-10% of isooctanol quality, and hydrogen follows
Ring, in 180-230 DEG C of reaction, substantially after not water outlet, sampling GC detections, two octodrine contents≤2%, which reacts, to be terminated；Otherwise continue
Insulation finally gives tri-iso-octylamine crude product until qualified；Then by a small amount of unreacted isooctanol essence in tri-iso-octylamine crude product
After evaporating, recycled；
Shown in described tri-iso-octylamine structural formula such as formula (I)：
Described catalyst is alkaline earth oxide catalyst.Described alkaline earth oxide catalyst is oxidation
One kind or two kinds and more than two kinds of mixing in magnesium, nickel oxide, zinc oxide, cupric oxide.
Described alkaline earth oxide catalyst, use copper nitrate, nickel nitrate aqueous solution using Cu and Ni as active matter
It is prepared using equi-volume impregnating, its step includes：By Cu (NO3)2·3H2O, Ni (NO3)2·6H2O, Zn (NO3)2·
6H2O, Mg (NO3)2·6H2O is dissolved in a certain amount of water, acetone or ethylene glycol, is then added corresponding with liquor capacity
SiO2、Al2O3、ZrO2、Ca2CO3In one or more as catalyst carrier, stir into a paste, in 50 ± 5 DEG C of water-baths
5 ± 1h of aging, drying is filtered, 1-24h is calcined at 300-800 DEG C, is crushed to below 200 mesh, that is, catalyst, high catalysis is made
Activity and selectivity.
The preferred sintering temperature of described catalyst is 450 ± 10 DEG C, and roasting time is 4 ± 0.5h.
In step 2), described isooctanol and two octodrine mol ratios are 1~2:1；
Method prepared by described tri-iso-octylamine, its reaction equation are：
Beneficial effect：
The present invention can realize obtained tri-iso-octylamine, more in the prior art using different pungent by the inexpensive raw material easily obtained
Aldehyde more has cost of material advantage.
A small amount of unreacted isooctanol can be with recycled, simple to operate, non-corrosiveness or excitant thing in production process
Matter produces, thus will not corrode production equipment and generation environment pollution.
The present invention uses catalyst to have higher activity, selectivity and stability and post processing is simple, catalyst
It is reusable to be easily achieved industrialization.For the high conversion rate of isooctanol up to 89.5%, product selectivity is up to 81.3%.
Embodiment
With reference to embodiment, the embodiment of the present invention is described in further detail.Following examples are used to say
The bright present invention, but it is not limited to the scope of the present invention.
GC analysis conditions：
Instrument and equipment
A) gas chromatograph：The gas chromatograph for any model that sensitivity and stability comply with relevant regulations；
B) chromatographic column：Capillary column model HP-5 provides the pillar of 50m × 0.32mm × 0.52 μm or other same types；
C) data processor or chromatographic work station；
D) flame ionization ditector；
E) microsyringe, 10 μ L.
Chromatographiccondition is set：
A) column temperature：Initial temperature is 180 DEG C, 10 DEG C/min of heating rate, final temperature 280 DEG C (10min)；
B) pressure before post：100kpa；
C) temperature of vaporization chamber：280℃；
D) detector temperature：280℃；
E) carrier gas flux：About 20ml/min；
F) gas flow：About 40ml/min；
G) combustion air current amount：About 400ml/min.
The physical parameter of gained tri-iso-octylamine product of the invention is as follows：
Outward appearance:It is colourless to arrive light yellow clear liquid；
Color and luster APHA：≤30；
Content:>98%；
Moisture content:<0.3%.
Embodiment 1
The preparation of catalyst：By Cu (NO3)2·3H2O, Ni (NO3)2·6H2O, Zn (NO3)2·6H2O, Mg (NO3)2·
6H2O is dissolved in a certain amount of water, acetone or ethylene glycol, then adds ZrO corresponding with liquor capacity2Carried as catalyst
Body, stir into a paste, in 50 ± 5 DEG C of water-bath 5 ± 1h of aging, filter drying, be calcined 4 ± 0.5h at 450 ± 10 DEG C, crush
To below 200 mesh, that is, catalyst is made.
Two octodrines (400g), catalyst (20g) are put into 1 liter of four mouthfuls of reaction bulb, reaction bulb band hydrogen is circulated and divided
Water installations.Nitrogen displacement, after hydrogen displacement, reducing catalyst 2 hours between 200-210 DEG C, isooctanol (260g) is then added dropwise,
Reaction temperature is 200-210 DEG C, and reaction constantly has water generation, and after 20 hours substantially after not water outlet, sampling GC is analyzed, two octodrines
1%, tri-iso-octylamine 74%.Gained crude product is directly used in rectification step, product content 98.3%.
Embodiment 2
The preparation of catalyst：By Cu (NO3)2·3H2O, Ni (NO3)2·6H2O, Zn (NO3)2·6H2O, Mg (NO3)2·
6H2O is dissolved in a certain amount of water, acetone or ethylene glycol, then adds Ca corresponding with liquor capacity2CO3Carried as catalyst
Body, stir into a paste, in 50 ± 5 DEG C of water-bath 5 ± 1h of aging, filter drying, be calcined 4 ± 0.5h at 450 ± 10 DEG C, crush
To below 200 mesh, that is, catalyst is made.
Two octodrines (450g), catalyst (20g) are put into 1 liter of four mouthfuls of reaction bulb, reaction bulb band hydrogen is circulated and divided
Water installations.Nitrogen displacement, after hydrogen displacement, reducing catalyst 2 hours between 190-200 DEG C, isooctanol (260g) is then added dropwise,
Reaction temperature is 200-210 DEG C, and reaction constantly has water generation, and after 18 hours substantially after not water outlet, sampling GC is analyzed, two octodrines
2%, tri-iso-octylamine 80%.Gained crude product is directly used in rectification step, product content 98.5%.
Embodiment 3
The preparation of catalyst：By Cu (NO3)2·3H2O, Ni (NO3)2·6H2O, it is dissolved in a certain amount of water, acetone or second
In glycol, Ca corresponding with liquor capacity is then added2CO3As catalyst carrier, stir into a paste, in 50 ± 5 DEG C of water
5 ± 1h of aging is bathed, drying is filtered, is calcined 4 ± 0.5h at 450 ± 10 DEG C, is crushed to below 200 mesh, that is, catalyst is made.
Two octodrines (450g), catalyst (20g) are put into 1 liter of four mouthfuls of reaction bulb, reaction bulb band hydrogen is circulated and divided
Water installations.Nitrogen displacement, after hydrogen displacement, reducing catalyst 2 hours between 190-200 DEG C, isooctanol (260g) is then added dropwise,
Reaction temperature is 200-210 DEG C, and reaction constantly has water generation, and after 18 hours substantially after not water outlet, sampling GC is analyzed, two octodrines
3%, tri-iso-octylamine 78%.Gained crude product is directly used in rectification step, product content 98.8%.
Embodiment 4
The preparation of catalyst：With embodiment 1
Two octodrines (450g), catalyst (25g) are put into 1 liter of four mouthfuls of reaction bulb, reaction bulb band hydrogen is circulated and divided
Water installations.Nitrogen displacement, after hydrogen displacement, reducing catalyst 2 hours between 190-200 DEG C, isooctanol (260g) is then added dropwise,
Reaction temperature is 220-230 DEG C, and reaction constantly has water generation, and after 18 hours substantially after not water outlet, sampling GC is analyzed, two octodrines
1.5%, tri-iso-octylamine 82.5%.Gained crude product is directly used in rectification step, product content 98.7%.
Claims (10)
1. a kind of preparation method of tri-iso-octylamine, its preparation process include：Two octodrines, catalyst are put into reactor, nitrogen
After gas displacement, hydrogen displacement, in 180-230 DEG C of 2 ± 1h of reducing catalyst, isooctanol is then added dropwise, hydrogen circulation, heating is instead
Should；GC detections are sampled, terminates when two octodrine contents≤2Wt.% reacts, obtains tri-iso-octylamine crude product；
Described tri-iso-octylamine structural formula is such as shown in (I)：
A kind of 2. preparation method of tri-iso-octylamine according to claim 1, it is characterised in that：Described isooctanol and two different
The mol ratio of octylame is 1~2:1.
A kind of 3. preparation method of tri-iso-octylamine according to claim 1：It is characterized in that：Described catalyst is alkaline earth
Metal oxide catalyst.
A kind of 4. preparation method of tri-iso-octylamine according to claim 1,2 or 3, it is characterised in that：Described catalyst
Dosage be isooctanol quality 0.5%-10%.
A kind of 5. preparation method of tri-iso-octylamine according to claim 3, it is characterised in that：Described alkaline-earth metal oxide
Thing catalyst is magnesia, nickel oxide, zinc oxide, one kind in cupric oxide or two kinds and more than two kinds of mixing.
A kind of 6. preparation method of tri-iso-octylamine according to claim 5, it is characterised in that：Described alkaline-earth metal oxide
Thing catalyst, its preparation method are：By Cu (NO3)2·3H2O, Ni (NO3)2·6H2O, Zn (NO3)2·6H2O, Mg (NO3)2·
6H2One kind or two kinds and more than two kinds of mixing in O, are dissolved in water, acetone or ethylene glycol, then addition and liquor capacity
Suitable catalyst carrier, stirs into a paste, and in 50 ± 5 DEG C of water-bath 5 ± 1h of aging, filters drying, is roasted at 300-800 DEG C
1-24h is burnt, is crushed to below 200 mesh, that is, obtains catalyst.
A kind of 7. preparation method of tri-iso-octylamine according to claim 6, it is characterised in that：Described catalyst carrier is
SiO2、Al2O3、ZrO2、Ca2CO3In one or more.
A kind of 8. preparation method of tri-iso-octylamine according to claim 6, it is characterised in that：Described catalyst it is preferred
Sintering temperature is 450 ± 10 DEG C, and roasting time is 4 ± 0.5h.
A kind of 9. preparation method of tri-iso-octylamine according to claim 1,2 or 3, it is characterised in that：Described isooctanol
With 180-230 DEG C of the reaction temperature of two octodrines.
A kind of 10. preparation method of tri-iso-octylamine according to claim 1,2 or 3：It is characterized in that：Described three are different pungent
The preparation method of amine, its preparation process also include：Tri-iso-octylamine crude product obtains tri-iso-octylamine finished product through rectifying.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106596779A (en) * | 2016-12-20 | 2017-04-26 | 广电计量检测（西安）有限公司 | Detection method for bis(2-ethylhexyl)amine in leather and textiles |
| CN111470972A (en) * | 2020-04-24 | 2020-07-31 | 安徽天择化工有限公司 | Isooctyl isotridecyl secondary amine and preparation method and application thereof |
| WO2022250790A1 (en) * | 2021-05-25 | 2022-12-01 | Dow Technology Investments Llc | Processes for the vapor phase hydrogenation of aldehydes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106513002A (en) * | 2016-11-03 | 2017-03-22 | 中南大学 | Catalyst used for catalyzing synthesis of aliphatic tertiary amine from primary amine or secondary amine and fatty alcohol as well as preparation and application of catalyst |
-
2017
- 2017-08-10 CN CN201710679056.8A patent/CN107556197A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106513002A (en) * | 2016-11-03 | 2017-03-22 | 中南大学 | Catalyst used for catalyzing synthesis of aliphatic tertiary amine from primary amine or secondary amine and fatty alcohol as well as preparation and application of catalyst |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106596779A (en) * | 2016-12-20 | 2017-04-26 | 广电计量检测（西安）有限公司 | Detection method for bis(2-ethylhexyl)amine in leather and textiles |
| CN111470972A (en) * | 2020-04-24 | 2020-07-31 | 安徽天择化工有限公司 | Isooctyl isotridecyl secondary amine and preparation method and application thereof |
| WO2022250790A1 (en) * | 2021-05-25 | 2022-12-01 | Dow Technology Investments Llc | Processes for the vapor phase hydrogenation of aldehydes |
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Application publication date: 20180109 |