CN1181047C - N,N-di (1-methyl, heptyl) acetylamine production method - Google Patents
N,N-di (1-methyl, heptyl) acetylamine production method Download PDFInfo
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- CN1181047C CN1181047C CNB011285524A CN01128552A CN1181047C CN 1181047 C CN1181047 C CN 1181047C CN B011285524 A CNB011285524 A CN B011285524A CN 01128552 A CN01128552 A CN 01128552A CN 1181047 C CN1181047 C CN 1181047C
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- Prior art keywords
- methylheptyl
- product
- amine
- production method
- acetamide
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- RTTCFFTVCUNXLX-UHFFFAOYSA-N n,n-di(octan-2-yl)acetamide Chemical compound CCCCCCC(C)N(C(C)=O)C(C)CCCCCC RTTCFFTVCUNXLX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- -1 1-methylheptyl Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 229910052742 iron Inorganic materials 0.000 claims description 7
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 6
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 3
- 150000004985 diamines Chemical class 0.000 abstract 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000005915 ammonolysis reaction Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a production method for preparing N, N-di(1-methyl heptyl) acetamide. In the method, raw materials of secondary octyl alcoho and NH3 react with each other at a certain temperature under the protection of H2 and the action of an R-Ni catalyst to generate crude diamine; then the crude diamine is rectified; the rectified crude diamine is used to carry out an acetylation reaction with acetic anhydride to obtain the product. The method has the advantages of production cost reduction and safe production.
Description
Technical Field
The invention relates to an improved production method of N, N-di- (1-methylheptyl) acetamide.
Background
The original method for producing N, N-di- (1-methylheptyl) acetamide is to use methyl heptanol to carry out ammonolysis by pure hydrogen under catalysis of Raney nickel to generate di- (1-methylheptyl) amine, and then to carry out acetylation reaction with acetic anhydride to obtain the product. In the process of generating the di- (1-methylheptyl) amine by ammonolysis, pure hydrogen is used for protecting the Raney nickel catalyst, so the method has the defects of large equipment investment, high production cost and multiple potential safety hazards.
Disclosure of Invention
The invention replaces pure hydrogen protected Raney nickel catalyst with mixed gas of hydrogen and nitrogen prepared by heating and catalytic decomposition of liquid ammonia to prepare di- (1-methylheptyl) amine intermediate, and then prepares N, N-di- (1-methylheptyl) acetamide from the intermediate, thereby saving equipment investment, reducing production cost and eliminating potential safety hazard brought by pure hydrogen production.
The reaction principle and the process of the invention are as follows:
the reaction mechanism is that when methyl heptanol is subjected to ammonolysis by introducing hydrogen and nitrogen under the catalysis of R-Ni, firstly, dehydrogenation is carried out to generate aldehyde, then, addition reaction with ammonia is carried out, dehydration is carried out to generate imine, then, hydrogenation is carried out to generate corresponding primary amine, the primary amine and sec-octanol react and dehydrate to obtain di- (1-methylheptyl) amine, and then, acetylation reaction is carried out on the di- (1-methylheptyl) amine and acetic anhydride to obtain the N, N-di- (1-methylheptyl) acetamide.
The specific reaction formula is as follows:
the principle and technical conditions of ammonia decomposition hydrogen production are as follows:
at a temperature of 600-740 ℃ and an iron catalyst (FeO/Fe)3O40.5 to 0.8) to obtain 75% H2And 25% N2The mixed gas of (1).
Liquid ammonia is easy to decompose, and NH is generated under the catalysis of iron catalyst at the normal pressure of 600-740 DEG C3The decomposition rate can reach more than 99.9 percent.
The technical scheme is as follows: a process for preparing N, N-di- (1-methylheptyl) acetamide from methylheptanol and NH3R-Ni catalyst and H obtained by decomposing liquid ammonia under the conditions of iron catalyst and 740 ℃ at 600-2、N2The mixed gas is reacted together to generate crude di- (1-methylheptyl) amine, and the crude di- (1-methylheptyl) amine is rectified and then is subjected to acetylation reaction with acetic anhydride to obtain the product. Methylheptanol and NH3The reaction temperature is 150-220 ℃.
A: preparation of H by liquid ammonia decomposition2Instead of pure H2The new process route for producing the product is feasible, and the conclusion can be drawn by the following comparison table and the physicochemical properties of the obtained product.
Preparation of H by decomposition of liquid ammonia2，N2Mixed gas and pure hydrogen ammonolysis are compared with the table.
Pure H for Shanghai2Preparation of H by ammonia liquid decomposition2Ammonolysis
(average of three months)
Hydrogen to ammonia ratio H2∶NH3＝10∶1 H2、N2∶NH3＝8∶1
The ammonolysis time of each batch is 28-30 hours/batch and 16-20 hours/batch
The consumption of the R-Ni catalyst is 13-15 kg/ton product and 5-6 kg/ton product
The yield of di- (1-methylheptyl) amine is 68 percent and 72 percent
The feeding amount of each batch of ammonolysis is 125kg and 500kg
The product quality is qualified
Generalization of all explosion-proof equipment for producing electric equipment
B: the product has physical and chemical properties.
Structural formula (xvi):
molecular weight: 283.5
The industrial product is yellow or light green non-volatile oil (the content is more than or equal to 95 percent).
Specific gravity: (d)4 25) 0.865～0.868
Viscosity (η)25) 19 to 20 centipoises
Light-inhibiting rate (η)25) 1.4450～1.4560
Ignition point: 190 deg.C
Flash point: 158 deg.C
Boiling point: 150 to 160 ℃ (1-2mmHg)
Solubility: (in water)<10mg/L
Toxicity: (LD50) 8.2g/KG
Thermal stability: 1mol of the product and 6NH in kerosene2SO4The solution or 6N NaOH solution has no obvious change after continuous reaction for 168 hours at 80 ℃.
Drawings
FIG. 1 is a flow chart of a process for producing N, N-bis- (1-methylheptyl) acetamide.
Detailed Description
Liquid ammonia (NH)3) The temperature was raised to 600 deg.C (740 deg.C) under the catalysis of iron catalyst (example is 600 deg.C, and the data in parentheses are the process conditions for carrying out the second). NH (NH)3Decomposition into H2And N2Under the two conditions, various raw materials and other process technical conditions are needed for producing 1 ton of the product.
Process technical conditions named ton consumption (t/t)
Methyl heptanol: 1.120(1.122) content is more than or equal to 90 percent
The content of 0.380(0.380) of acetic anhydride is more than or equal to 98 percent
Liquid ammonia (raw material): the content of 0.370(0.369) is more than or equal to 98 percent
Iron catalyst: 0.011(0.012) (FeO/Fe)3O4)＝0.5～0.8
Liquid ammonia (for producing H)2For use): 60(70) the content of the cubic liter per hour is more than or equal to 98 percent.
The obtained product meets the industrial standard and is widely used for extracting industrial phenol-containing sewage. The method is used for treating and recycling phenol-containing wastewater in the industries of pharmacy, pesticides, coking, dyes, paints, spices, plastics, insulating materials and the like, and the phenol extraction rate can reach more than 99 percent; the method is used for treating the cadmium-containing wastewater, and the recovery rate of cadmium reaches 99 percent; the method is used for separating and purifying the rare precious metals such as niobium, tantalum, gallium, indium, rhenium, gold, palladium and thelike in the hydrometallurgy industry; it is used for iron removal and extraction separation in a rare earth-hydrochloric acid system.
Claims (1)
1. A production method for preparing N, N-di- (1-methylheptyl) acetamide is characterized in that: starting materials methylheptanol together with NH3R-Ni catalyst and H obtained by decomposing liquid ammonia under the conditions of iron catalyst and 740 ℃ at 600-2、N2The mixed gas is reacted together to generate crude di- (1-methylheptyl) amine, and the crude di- (1-methylheptyl) amine is rectified and then is subjected to acetylation reaction with acetic anhydride to obtain the product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011285524A CN1181047C (en) | 2001-08-17 | 2001-08-17 | N,N-di (1-methyl, heptyl) acetylamine production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011285524A CN1181047C (en) | 2001-08-17 | 2001-08-17 | N,N-di (1-methyl, heptyl) acetylamine production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1405149A CN1405149A (en) | 2003-03-26 |
| CN1181047C true CN1181047C (en) | 2004-12-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011285524A Expired - Fee Related CN1181047C (en) | 2001-08-17 | 2001-08-17 | N,N-di (1-methyl, heptyl) acetylamine production method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1181047C (en) |
-
2001
- 2001-08-17 CN CNB011285524A patent/CN1181047C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1405149A (en) | 2003-03-26 |
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Owner name: SHAOYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Free format text: FORMER OWNER: LUO ZHANGZHENG Effective date: 20030208 |
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| DD01 | Delivery of document by public notice |
Addressee: Zhou Daren Document name: patent for invention |
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Addressee: Shaoyang City Inst. of Chemical Engineering Document name: Notification to Pay the Fees |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20041222 Termination date: 20190817 |
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| CF01 | Termination of patent right due to non-payment of annual fee |