CN110483322A - A kind of preparation method of adipamide - Google Patents
A kind of preparation method of adipamide Download PDFInfo
- Publication number
- CN110483322A CN110483322A CN201910750057.6A CN201910750057A CN110483322A CN 110483322 A CN110483322 A CN 110483322A CN 201910750057 A CN201910750057 A CN 201910750057A CN 110483322 A CN110483322 A CN 110483322A
- Authority
- CN
- China
- Prior art keywords
- adipamide
- preparation
- reaction
- adipic acid
- kilograms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000001361 adipic acid Substances 0.000 claims abstract description 21
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004202 carbamide Substances 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000011343 solid material Substances 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 18
- 238000003756 stirring Methods 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000001681 protective effect Effects 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 230000005311 nuclear magnetism Effects 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000011938 amidation process Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation methods of adipamide, the following steps are included: adipic acid, urea are placed in reaction kettle, it is heated to molten condition, it is reacted, reaction product by once it is cooling, water is added dropwise and stirs, solid material be obtained by filtration after secondary cooling, which obtains adipamide solid after washing.Compared with prior art, the present invention has the advantages that simple combined coefficient height, product yield high, process, environmentally protective, safety, good product quality, stable operation, the three wastes are few, production cost is low etc..
Description
Technical field
The present invention relates to chemical industry synthesis fields, more particularly, to a kind of preparation method of adipamide.
Background technique
Aliphatic polybasic amide is important chemical intermediate for synthesizing cyanides.Meanwhile it is also used as
Gu flux can effectively reduce the melt viscosity of block copolymer, but not reduce its mechanical strength.In addition polymer can also be used as
Raw material monomer, synthesize various amides high polymers, there is multiple use.
Prepare document very much, Chinese patent CN103140467A and the United States Patent (USP) US20060024747 of adipamide
Elaborate that a kind of bioenzymatic conversion method prepares adipamide using adiponitrile as raw material, the disadvantage is that wastewater flow rate is big, raw material oneself two
Nitrile is more expensive；In Chinese patent CN108250096A, Yan Yida et al. is using dimethyl adipate as raw material, with P-Toluidine's aqueous solution
It reacts to prepare adipamide, the method equally exists, generation waste water big disadvantage more using raw material；Chinese patent
In CN105001033A, Sun Hailong et al. propose one kind using adipic acid as raw material, it is anti-at high temperature under high pressure with ammonia or ammonium hydroxide
Should be come the method for preparing adipamide, the shortcomings that the method is high-temperature high-voltage reaction condition to be used, and is especially more than reaction, right
Equipment requirement is high, and there is also certain risk factors.
Summary of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide a kind of efficient, green rings
It protects, the preparation method of the adipamide of safety.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of preparation method of adipamide, comprising the following steps: adipic acid, urea are placed in reaction kettle, heated
To molten condition, reacted, reaction product by once it is cooling, water is added dropwise and stirs, solid be obtained by filtration after secondary cooling
Material, the solid material obtain adipamide solid after washing.
Specific reaction process is as follows:
It is reacted in Chinese patent CN105001033A using adipic acid and ammonia or ammonium hydroxide, and the present invention is using urine
Element is used as ammonia source, in the molten state due to urea and raw material adipic acid, amidation process occurs, thus release carbon monoxide and
Water, under normal pressure, the by-product of reaction are removed constantly from system, and reaction is constantly carried out to forward direction, thus reaction does not have substantially
There is side reaction product, thus realize Atom economy, it is environmentally protective.
The molar ratio of the adipic acid and urea is 1.0:0.8~2.0.
Preferably, the molar ratio of the adipic acid and urea is 1.0:1.0~1.3.
The reaction temperature of the reaction is 140~180 DEG C.
Preferably, the reaction temperature of the reaction is 160~170 DEG C.
The reaction time of the reaction is 5~7 hours.
The temperature once cooled down is 80~100 DEG C.
Preferably, the temperature once cooled down is 90-100 DEG C.
The quality that water is added dropwise is 0.8~30 times of adipic acid quality in raw material.
Preferably, the quality that water is added dropwise is 1~15 times of adipic acid quality in raw material.
Wherein, when stirring after dropwise addition water, temperature of charge remains 60~80 DEG C.
Compared with prior art, the invention has the following advantages that
(1) production process of the invention is simple, generated time section, high production efficiency, and entire production process green ring
It protects, safety；
(2) yield of the adipamide of the technique is up to 85~95%, and the product of production has high-quality, operation surely
Fixed, high income, the feature that the three wastes are few, production cost is low, have high economic benefit.
(3) operating condition of the invention is mild, does not need high-temperature and high-pressure conditions, lower to equipment requirement, is conducive to industry
Using.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.Following embodiment will be helpful to the technology of this field
Personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the ordinary skill of this field
For personnel, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to the present invention
Protection scope.
Embodiment 1
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100.0mol) and (6.2 kilograms, 102.6mol) of urea mixing, it is then heated to 165
Degree, system become liquid, after reacting 6 hours at this temperature, are cooled to 100 degree, are added dropwise 150 kilograms of water, stirring a period of time
Afterwards, cooling, filtering, washing obtains white solid, and 13.7 kilograms of target products after drying, yield is 95.0%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s, 2H), 6.69 (s, 2H), 1.95-2.03 (m, 4H), 1.41-1.46 (m, 4H) show that the target product is adipamide.
Embodiment 2
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100.0mol) and (5.4 kilograms, 90.0mol) of urea mixing, it is then heated to 165
Degree, system become liquid, after reacting 6 hours at this temperature, are cooled to 100 degree, are added dropwise 150 kilograms of water, stirring a period of time
Afterwards, cooling, filtering, washing obtains white solid, and 12.3 kilograms of target products after drying, yield is 85.0%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95–2.03(m,4H),1.41-1.46(m,4H)。
Embodiment 3
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100mol) and (6.2 kilograms, 102.6mol) of urea mixing, it is then heated to 175
Degree, system become liquid, after reacting 6 hours at this temperature, are cooled to 100 degree, are added dropwise 150 kilograms of water, stirring a period of time
Afterwards, cooling, filtering, washing obtains white solid, and 13.5 kilograms of target products after drying, yield is 93.7%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95–2.03(m,4H),1.41-1.46(m,4H)。
Embodiment 4
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100mol) and (7.2 kilograms, 120.0mol) of urea mixing, it is then heated to 165
Degree, system become liquid, after reacting 6 hours at this temperature, are cooled to 100 degree, are added dropwise 150 kilograms of water, stirring a period of time
Afterwards, cooling, filtering, washing obtains white solid, and 13.6 kilograms of target products after drying, yield is 94.7%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95-2.03(m,4H),1.41-1.46(m,4H)。
Embodiment 5
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100mol) and (4.8 kilograms, 80mol) of urea mixing, it is then heated to 180 degree, body
System becomes liquid, after reacting 5 hours at this temperature, is cooled to 90 degree, is added dropwise 438 kilograms of water, cold after stirring a period of time
But, it filters, washing obtains white solid, and 12.35 kilograms of target products after drying, yield is 81%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95-2.03(m,4H),1.41-1.46(m,4H)。
Embodiment 6
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100mol) and (14.4 kilograms, 240.0mol) of urea mixing, it is then heated to 140
Degree, system become liquid, after reacting 7 hours at this temperature, are cooled to 80 degree, are added dropwise 12 kilograms of water, after stirring a period of time,
Cooling, filtering, washing obtains white solid, and 12.6 kilograms of target products after drying, yield is 80%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95-2.03(m,4H),1.41-1.46(m,4H)。
Embodiment 7
A kind of preparation method of adipamide, its step are as follows:
By adipic acid (14.6 kilograms, 100mol) and (7.86 kilograms, 130mol) of urea mixing, 170 degree are then heated to,
System becomes liquid, after reacting 6 hours at this temperature, is cooled to 100 degree, is added dropwise 15 kilograms of water, cold after stirring a period of time
But, it filters, washing obtains white solid, and 13.8 kilograms of target products after drying, yield is 93.0%.
Obtained target product is characterized, nuclear-magnetism characterize data are as follows:1H NMR(500MHz,DMSO-d6)δ7.23
(s,2H),6.69(s,2H),1.95–2.03(m,4H),1.41-1.46(m,4H)。
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring substantive content of the invention.
Claims (10)
1. a kind of preparation method of adipamide, which comprises the following steps: adipic acid, urea are placed in reaction
In kettle, it is heated to molten condition, is reacted, reaction product is obtained by filtration solid after once cooling, dropwise addition water, secondary cooling
Body material, the solid material obtain adipamide solid after washing.
2. a kind of preparation method of adipamide according to claim 1, which is characterized in that the adipic acid and urea
Molar ratio be 1.0:0.8~2.0.
3. a kind of preparation method of adipamide according to claim 2, which is characterized in that the adipic acid and urea
Molar ratio be 1.0:1.0~1.3.
4. a kind of preparation method of adipamide according to claim 1, which is characterized in that the reaction temperature of the reaction
Degree is 140~180 DEG C.
5. a kind of preparation method of adipamide according to claim 4, which is characterized in that the reaction temperature of the reaction
Degree is 160~170 DEG C.
6. a kind of preparation method of adipamide according to claim 1, which is characterized in that when the reaction of the reaction
Between be 5~7 hours.
7. a kind of preparation method of adipamide according to claim 1, which is characterized in that the temperature once cooled down
Degree is 80~100 DEG C.
8. a kind of preparation method of adipamide according to claim 7, which is characterized in that the temperature once cooled down
Degree is 90-100 DEG C.
9. a kind of preparation method of adipamide according to claim 1, which is characterized in that the quality that water is added dropwise
It is 0.8~30 times of adipic acid quality in raw material.
10. a kind of preparation method of adipamide according to claim 9, which is characterized in that the matter that water is added dropwise
Amount is 1~15 times of adipic acid quality in raw material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910750057.6A CN110483322A (en) | 2019-08-14 | 2019-08-14 | A kind of preparation method of adipamide |
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| CN201910750057.6A CN110483322A (en) | 2019-08-14 | 2019-08-14 | A kind of preparation method of adipamide |
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| CN110483322A true CN110483322A (en) | 2019-11-22 |
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| CN201910750057.6A Pending CN110483322A (en) | 2019-08-14 | 2019-08-14 | A kind of preparation method of adipamide |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2109941A (en) * | 1936-06-05 | 1938-03-01 | Du Pont | Preparation of amides |
| CN102276477A (en) * | 2011-06-08 | 2011-12-14 | 珠海真绿色技术有限公司 | Preparation method of 1,8-diamino-octane |
-
2019
- 2019-08-14 CN CN201910750057.6A patent/CN110483322A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2109941A (en) * | 1936-06-05 | 1938-03-01 | Du Pont | Preparation of amides |
| CN102276477A (en) * | 2011-06-08 | 2011-12-14 | 珠海真绿色技术有限公司 | Preparation method of 1,8-diamino-octane |
Non-Patent Citations (2)
| Title |
|---|
| 张春华 等: "癸二酰胺的合成", 《青岛科技大学学报（自然科学版）》 * |
| 熊万明 等: "《有机化学实验》", 31 January 2017, 北京理工大学出版社 * |
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Application publication date: 20191122 |
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