CN110294678A - The method that fatty double alkyl secondary amines and formaldehyde prepare the double alkyl tertiary amines of N- methyl - Google Patents
The method that fatty double alkyl secondary amines and formaldehyde prepare the double alkyl tertiary amines of N- methyl Download PDFInfo
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- CN110294678A CN110294678A CN201910378721.9A CN201910378721A CN110294678A CN 110294678 A CN110294678 A CN 110294678A CN 201910378721 A CN201910378721 A CN 201910378721A CN 110294678 A CN110294678 A CN 110294678A
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- formaldehyde
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- fat
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 163
- -1 alkyl secondary amines Chemical class 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 3
- 238000006073 displacement reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 description 13
- 229910052759 nickel Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 6
- 238000012797 qualification Methods 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the methods that a kind of double alkyl secondary amines of fat and formaldehyde prepare the double alkyl tertiary amines of N- methyl, belong to the synthetic method field of compound in organic chemical industry, it is described the preparation method is as follows: fatty double alkyl secondary amines and formaldehyde are carried out hydrogenation under the action of catalyst at 100-170 DEG C, pressure is in 0.2-0.5mpa；Wherein the molar ratio of the double alkyl secondary amines of fat and formaldehyde is 1.0-1.5；The water of formalin institute's band and reaction generation is sloughed during the reaction, after the reaction was completed, directly filters, finished product can be obtained.Present invention reaction does not need to add alkali neutralization after the reaction was completed, does not need to wash, do not need drying, can reduce waste water displacement, simple flow since acid catalyst is not added.
Description
Technical field
The present invention relates to the methods that a kind of double alkyl secondary amines of fat and formaldehyde prepare the double alkyl tertiary amines of N- methyl, belong to organic
The synthetic method field of compound in chemical industry.
Background technique
Its structure of double alkyl tertiary amines is as follows:
R carbon atom is 8-20, and double alkyl tertiary amines are the important intermediates for preparing quaternary ammonium salt, do cation quaternary ammonium salt
Important source material, germicidal hard-surface agent, as the fabric softening processing after washing, at artificial, fiber antistatic softness
Reason has excellent flexibility；It is also used as cleanser sour in fuel oil, there is very big application in weaving, daily use chemicals；
It is to do bentonitic raw material.
Due to the high industrial significance of the double alkyl tertiary amines of N- methyl, prepare that there are many retouch to it in economic and technical document
It states.Fatty alcohol and monomethyl amine reaction generate double long-chain alkyl methyl tertiary amine.
Sun Baoxing is in its paper: the preparation of double long-chain alkyl methyl tertiary amine and its quaternary ammonium salt describes in this way, fatty alcohol and one
Methylamine reaction generates double long-chain alkyl methyl tertiary amine and water, and for reaction temperature in 210-220 degree, reaction temperature is higher, and reacts
After the completion, product is filtered into brown, needs extracting and refining, process cumbersome.See (fine chemistry industry double long-chain alkyl methyl tertiary amine and its
The preparation grandson Bao Xinglili nineteen nineties of page 64 of quaternary ammonium salt).
In the synthesis of fatty primary secondary amine and second phase Surfactant Industry page 18 of application (Li Jian) 2000, secondary amine and first
120-130 DEG C of aldehyde reaction, pressure 1-1.5mpa, continuous formaldehyde reaction, conversion ratio 98-100%；Yield is 95%.
The production domesticization of fatty amine process units, Ye Jianquan, introducing its technique in text is double alkyl secondary amines and formaldehyde reaction, is added
Acetic acid is catalyst, improves much than traditional Liu's Carter process technique, but since formaldehyde concentration itself is not high, can bring into
Many water enter reaction kettle, keep single batch of yield of reaction kettle very low, and need to add hydroxide since its subsequent processing of acetic acid is added
Sodium is neutralized, discharges water, is dried.Subsequent processing trouble, wastewater flow rate is big, poor product quality.Labor intensity of workers is big.
" 2005 Mount Huang world surfactant meetings and the 16th national industrial surface activity agent development seminar paper
Collection " the 33-36 pages.
Summary of the invention
It is insufficient according to prior art, the technical problem to be solved by the present invention is provide a kind of double alkyl secondary amines of fat and
Acid catalyst is not added in the method that formaldehyde prepares the double alkyl tertiary amines of N- methyl, the present invention, does not need to add in alkali after the reaction was completed
With do not need to wash, do not need drying, waste water displacement, simple flow can be reduced.
The technical solution adopted by the present invention to solve the technical problems is: providing a kind of fatty pair of alkyl secondary amine and formaldehyde system
The method of the double alkyl tertiary amines of standby N- methyl, it is described the preparation method is as follows:
Fatty double alkyl secondary amines and formaldehyde are subjected to hydrogenation under the action of catalyst at 100-170 DEG C, pressure exists
0.2-0.5mpa；Wherein the molar ratio of the double alkyl secondary amines of fat and formaldehyde is 1.0-1.5；Formalin is sloughed during the reaction
The water that institute's band and reaction generate directly filters after the reaction was completed, finished product can be obtained.
The method that the double alkyl secondary amines of the fat and formaldehyde prepare the double alkyl tertiary amines of N- methyl, the preparation method is such as
Under:
The double alkyl secondary amines of fat and catalyst is added in autoclave, is successively passed through nitrogen and hydrogen is replaced, maintain hydrogen
Atmospheric pressure is warming up to 100 DEG C -170 DEG C in 0.2mpa, starts successively to be passed through formaldehyde, while being successively vented outwards,
Reaction kettle is discharged in the water that reaction generates in time, the time that is passed through of formaldehyde is 2-6 hours.Discharge filters after reaction, can obtain
Product.
Hydrogenation temperature is 130-170 DEG C.
The molar ratio of the double alkyl secondary amines of the fat and formaldehyde is 1.05:1.2.
The catalyst is supporter nickel catalyst, and additive amount is the 0.2---1% that the quality of secondary amine is added.
The described double alkyl secondary amines of fat are mixing or the double alkylamines of symmetrical aliphatic, with straight chain, are saturated, have
The alkyl of 8-24 carbon atom.
The double alkyl secondary amines of the fat are the alkyl secondary amine of 12-24 carbon atom.
It is successively passed through formaldehyde, while being successively vented outwards and reaction kettle is discharged in the water that reaction generates in time, is made
It reacts and is carried out to the Direction of Reaction of target product.
The double alkyl tertiary amine new processes of double alkyl secondary amines and formaldehyde preparation N- methyl of the invention, with double alkyl secondary amines, formalin
Solution, hydrogen are raw material, and under the action of supporter nickel catalyst, catalytic hydrogenation generates double alkyl tertiary amines and water, and catalyst is to carry
Body nickel.
The reaction equation of the double alkyl tertiary amines of N- methyl of the present invention:
The double alkyl tertiary amine new processes of double alkyl secondary amines and formaldehyde preparation N- methyl of the invention, with double alkyl secondary amines, formalin
Solution, hydrogen are raw material, under the action of supporter nickel catalyst, generate double alkyl tertiary amines and water, water is in this temperature and pressure
Under, it is successively discharged from reaction kettle, carries out reaction towards goal response object.
The beneficial effects of the present invention are:
(1) reaction pressure is low, invests low；
(2) after the completion of due to this technological reaction, there is no water in reaction kettle, one-pot production capacity increases；
(3) reaction does not need to add alkali neutralization after the reaction was completed, does not need to wash, not need since acid catalyst is not added
It is dry, waste water displacement, simple flow can be reduced；
(4) this production technology fully reacting, product coloration is good, improves product quality, is easy to large-scale production.
The embodiment of the present invention is described further below:
Embodiment 1
The method that a kind of double alkyl secondary amines of fat and formaldehyde prepares N- methyl pair dodecyl tertiary amines, the preparation method
It is as follows:
Double dodecyl secondary amine 353.7 (1.09mol) gram are added in 1 liter of stainless steel autoclave, catalyst is added
0.2%, catalyst is carrier nickel, is then replaced 3 times with nitrogen, then replaced 3 times with hydrogen, heating, being flushed with hydrogen atmospheric pressure is
0.2mpa；Revolving speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, while to outlet
Gas, capacity are 0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, it is cold with condenser
It is solidifying.Hydrogen is constantly logical to reaction kettle, and maintenance pressure is 0.3mpa；37% formalin 88.2ml was squeezed at 5 hours
In reaction kettle, reaction temperature maintains 150 DEG C, and product, sampling analysis, when total amine value-tertiary amine value < 1 are made after the reaction was completed
Mg/g is the total amine value of qualification are as follows: 148.2, tertiary amine value: 147.5.
Embodiment 2
The method that a kind of double alkyl secondary amines of fat and formaldehyde prepares N- methyl pair myristyl tertiary amines, the preparation method
It is as follows:
Double myristyl secondary amine 386.8 (0.94mol) gram are added in 1 liter of stainless steel autoclave, catalyst is added
0.3%, catalyst is carrier nickel, is then replaced 3 times with nitrogen, then replaced 3 times with hydrogen, heating, being flushed with hydrogen atmospheric pressure is
0.2mpa；Revolving speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, while to outlet
Gas, capacity are 0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, it is cold with condenser
It is solidifying.Hydrogen is constantly logical to reaction kettle, and maintenance pressure is 0.2mpa；37% formalin 76.51ml was beaten at 4 hours
Enter in reaction kettle, reaction temperature maintains 150 DEG C, and product, sampling analysis, total amine value-tertiary amine value < 1 are made after the reaction was completed
When mg/g be the total amine value of qualification are as follows: 130.2, tertiary amine value: 129.5.
Embodiment 3
A kind of method that fatty pair of alkyl secondary amines and formaldehyde prepare N- methyl double hexadecyl tertiary amine, the preparation method
It is as follows:
Double hexadecyl secondary amine 388.3 (0.83mol) gram is added in 1 liter of stainless steel autoclave, catalyst is added
0.7%, catalyst is carrier nickel, is then replaced 3 times with nitrogen, then replaced 3 times with hydrogen, heating, being flushed with hydrogen atmospheric pressure is
0.2mpa；Revolving speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, while to outlet
Gas, capacity are 0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, it is cold with condenser
It is solidifying.Hydrogen is constantly logical to reaction kettle, and maintenance pressure is 0.3mpa；37% formalin 74.3ml was squeezed at 5 hours
In reaction kettle, reaction temperature maintains 150 DEG C, and product, sampling analysis, when total amine value-tertiary amine value < 1 are made after the reaction was completed
Mg/g is the total amine value of qualification are as follows: 114.2, tertiary amine value: 113.5.
Embodiment 4
The method that a kind of double alkyl secondary amines of fat and formaldehyde prepares N- methyl pair octadecyl tertiary amines, the preparation method
It is as follows:
Dioctadecyl Amine 389.5 (0.75mol) gram is added in 1 liter of stainless steel autoclave, catalyst 1% is added,
Catalyst is carrier nickel, is then replaced 3 times with nitrogen, then is replaced 3 times with hydrogen, heating, and being flushed with hydrogen atmospheric pressure is 0.2mpa；Turn
Speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, is vented outwards simultaneously, capacity is
0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, is condensed with condenser.Hydrogen continues not
Break logical to reaction kettle, maintenance pressure is 0.4mpa；37% formalin 66.6ml was squeezed into reaction kettle at 6 hours, is reacted
Temperature maintains 150 DEG C, after the reaction was completed sampling analysis, and mg/g is qualification total amine value when total amine value-tertiary amine value < 1 are as follows:
103.2, tertiary amine value: 102.5.
Embodiment 5
The method that a kind of double alkyl secondary amines of fat and formaldehyde prepares N- methyl pair tallow alkyl tertiary amines, the preparation method
It is as follows:
The double alkyl secondary amines 389.1 (0.78mol) gram of tallow are added in 1 liter of stainless steel autoclave, catalyst is added
0.3%, catalyst is carrier nickel, is then replaced 3 times with nitrogen, then replaced 3 times with hydrogen, heating, being flushed with hydrogen atmospheric pressure is
0.2mpa；Revolving speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, while to outlet
Gas, capacity are 0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, it is cold with condenser
It is solidifying.Hydrogen is constantly logical to reaction kettle, and maintenance pressure is 0.5mpa；37% formalin 69.3ml was squeezed at 5 hours
In reaction kettle, reaction temperature maintains 150 DEG C, and product, sampling analysis, when total amine value-tertiary amine value < 1 are made after the reaction was completed
Mg/g is the total amine value of qualification are as follows: 107.2, tertiary amine value: 106.5.
Embodiment 6
The method that a kind of double alkyl secondary amines of fat and formaldehyde prepares N- methyl pair palm alkyl tertiary amines, the preparation method
It is as follows:
Double palmityl secondary amine 388.8 (0.80mol) gram are added in 1 liter of stainless steel autoclave, catalyst 0.5% is added,
Catalyst is carrier nickel, is then replaced 3 times with nitrogen, then is replaced 3 times with hydrogen, heating, and being flushed with hydrogen atmospheric pressure is 0.2mpa；Turn
Speed is 1000 revs/min, and temperature rises to 140 DEG C, leads to formaldehyde into reaction kettle with metering pump, is vented outwards simultaneously, capacity is
0.1 liter/min；Reaction kettle is discharged in the water that formaldehyde is brought into and the water that reaction generates in time, is condensed with condenser.Hydrogen continues not
Break logical to reaction kettle, maintenance pressure is 0.3mpa；The formalin of 71.2ml37% was squeezed into reaction kettle at 2 hours, is reacted
Temperature maintains 150 DEG C, product is made after the reaction was completed, sampling analysis, mg/g is that qualification is total when total amine value-tertiary amine value < 1
Amine value are as follows: 109.2, tertiary amine value: 108.5.
Claims (7)
1. a kind of method that fat pair alkyl secondary amine and formaldehyde prepare the double alkyl tertiary amines of N- methyl, it is characterised in that the preparation
Method is as follows:
Fatty double alkyl secondary amines and formaldehyde are subjected to hydrogenation under the action of catalyst at 100-170 DEG C, pressure is in 0.2-
0.5mpa；Wherein the molar ratio of the double alkyl secondary amines of fat and formaldehyde is 1.0-1.5；Formalin institute band is sloughed during the reaction
The water generated with reaction directly filters after the reaction was completed, finished product can be obtained.
2. the method that fat pair alkyl secondary amine according to claim 1 and formaldehyde prepare the double alkyl tertiary amines of N- methyl, special
Sign be it is described the preparation method is as follows:
The double alkyl secondary amines of fat and catalyst is added in autoclave, is successively passed through nitrogen and hydrogen is replaced, maintain hydrogen pressure
Power is warming up to 100 DEG C -170 DEG C in 0.2mpa, starts successively to be passed through formaldehyde, while being successively vented outwards, will react
Reaction kettle is discharged in the water of generation in time, and the time that is passed through of formaldehyde is 2-6 hours.Discharge filters after reaction, can obtain product.
3. the method that fat pair alkyl secondary amine according to claim 1 or 2 and formaldehyde prepare the double alkyl tertiary amines of N- methyl,
It is characterized in that hydrogenation temperature is 130-170 DEG C.
4. the method that fat pair alkyl secondary amine according to claim 1 and formaldehyde prepare the double alkyl tertiary amines of N- methyl, special
Sign is that the molar ratio of the double alkyl secondary amines of the fat and formaldehyde is 1.05:1.2.
5. the method that fat pair alkyl secondary amine according to claim 1 and formaldehyde prepare the double alkyl tertiary amines of N- methyl, special
Sign is that the catalyst is supporter nickel catalyst, and additive amount is the 0.2---1% that the quality of secondary amine is added.
6. the method that fat pair alkyl secondary amine according to claim 1 or 3 and formaldehyde prepare the double alkyl tertiary amines of N- methyl,
It is characterized in that the double alkyl secondary amines of the fat are mixing or the double alkylamines of symmetrical aliphatic, with straight chain, is saturated, has
The alkyl of 8-24 carbon atom.
7. the method that fat pair alkyl secondary amine according to claim 5 and formaldehyde prepare the double alkyl tertiary amines of N- methyl, special
Sign is that the double alkyl secondary amines of the fat are the alkyl secondary amine of 12-24 carbon atom.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0492771A1 (en) * | 1990-12-21 | 1992-07-01 | Texaco Chemical Company | Continuous preparation of tertiary aliphatic methyl amines |
| CN1298865A (en) * | 1999-12-06 | 2001-06-13 | 巴斯福股份公司 | Amine prep. method |
| CN102822137A (en) * | 2010-04-07 | 2012-12-12 | 巴斯夫欧洲公司 | Process for preparing unsymmetrical secondary tert-butylamines in the liquid phase |
| CN103270014A (en) * | 2010-12-21 | 2013-08-28 | 花王株式会社 | Process for production of tertiary amine |
-
2019
- 2019-05-08 CN CN201910378721.9A patent/CN110294678A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0492771A1 (en) * | 1990-12-21 | 1992-07-01 | Texaco Chemical Company | Continuous preparation of tertiary aliphatic methyl amines |
| CN1298865A (en) * | 1999-12-06 | 2001-06-13 | 巴斯福股份公司 | Amine prep. method |
| CN102822137A (en) * | 2010-04-07 | 2012-12-12 | 巴斯夫欧洲公司 | Process for preparing unsymmetrical secondary tert-butylamines in the liquid phase |
| CN103270014A (en) * | 2010-12-21 | 2013-08-28 | 花王株式会社 | Process for production of tertiary amine |
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Application publication date: 20191001 |
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