CN104326940A - Method for synthesizing 2,6-dichlorobenzonitrile by ammoxidation - Google Patents
Method for synthesizing 2,6-dichlorobenzonitrile by ammoxidation Download PDFInfo
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- CN104326940A CN104326940A CN201410683052.3A CN201410683052A CN104326940A CN 104326940 A CN104326940 A CN 104326940A CN 201410683052 A CN201410683052 A CN 201410683052A CN 104326940 A CN104326940 A CN 104326940A
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- Prior art keywords
- dichlorobenzonitrile
- ammonia
- described catalyzer
- ammonia oxidation
- ammonium
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- 238000000034 method Methods 0.000 title claims abstract description 31
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 7
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 7
- 239000011609 ammonium molybdate Substances 0.000 claims description 7
- 229940010552 ammonium molybdate Drugs 0.000 claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 7
- 235000015320 potassium carbonate Nutrition 0.000 claims description 7
- 230000032683 aging Effects 0.000 claims description 5
- 239000012456 homogeneous solution Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- -1 salt ammonium meta-vanadate Chemical class 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 3
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 claims description 2
- 238000005554 pickling Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 abstract 3
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 abstract 3
- 230000002349 favourable effect Effects 0.000 abstract 1
- 229910003158 γ-Al2O3 Inorganic materials 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 3
- 238000010812 external standard method Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 2
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing 2,6-dichlorobenzonitrile by ammoxidation, which comprises the following step: by using 2,6-dichlorotoluene, ammonia and air as raw materials, carrying out one-step synthesis in a catalyst-filled fixed bed at 350-375 DEG C under the pressure of 0.02-0.1 MPa to obtain the 2,6-dichlorobenzonitrile, wherein the mole ratio of the 2,6-dichlorotoluene to the ammonia is 1:(2.8-5), the standard state air quantity is 0.2-0.5 m<3>/L catalyst L.h, and the catalyst is P-V-Mo-Cr-K-O/gamma-Al2O3. The method has the advantages of reasonable design, high operability and high overall yield. The brand-new ammoxidation catalyst is adopted to obtain favorable effect, so that the conversion rate of the 2,6-dichlorotoluene is up to 99.5%, and the mole yield of the 2,6-dichlorobenzonitrile is up to 95.0%.
Description
Technical field
The present invention relates to the method for a kind of ammonia oxidation synthesis 2,6-dichlorobenzonitrile.
Background technology
2,6-dichlorobenzonitrile may be used for the industries such as agricultural chemicals, medicine, pigment, dyestuff.The synthetic method of 2,6-traditional dichlorobenzonitriles is: 6-chlorine Ortho Nitro Toluene and chlorine reaction, and chlorination is also deviate from nitro and obtained 2,6-dichlorobenzyl chloride chlorinated mixture; 2,6-dichlorobenzyl chloride chlorinated mixture is hydrolyzed into 2,6-dichlorobenzaldehyde in formic acid, solder(ing)acid; 2,6-dichlorobenzaldehyde and oxammonium hydrochloride react and are dehydrated into 2,6-dichlorobenzonitrile.This method technical process is long, cost is high, wastewater flow rate is large, seriously polluted.
Current more advanced technique applies mechanically o-chloro benzonitrile fluidized-bed process and catalyzer; as Chinese patent ZL97109006.8; but; due to fluidized-bed special construction; residence time of material long (25 ~ 46 seconds), catalyst activity is too high, and 2; 6-dichlorobenzonitrile is very active, and easily carbonic acid gas and ammonium chloride are resolved in dechlorination open loop further.And traditional ammoxidation catalyst all adopts silica gel to do carrier.
Summary of the invention
Technical problem to be solved by this invention is for the deficiencies in the prior art, provides the method for ammonia oxidation synthesis 2, the 6-dichlorobenzonitrile that a kind of technological design is more reasonable, workable, excellent catalytic effect, yield are high.
For achieving the above object, the present invention adopts following technical scheme:
The method of a kind of ammonia oxidation synthesis 2,6-dichlorobenzonitrile, the method with 2,6-DCT, ammonia, air for raw material, loading catalyst in fixed bed, temperature 350 ~ 375 DEG C, under pressure 0.02 ~ 0.1MPa condition, one-step synthesis 2,6-dichlorobenzonitrile; The mol ratio of raw material is 2,6-DCT: ammonia=1: 2.8 ~ 5, and mark state air capacity is 0.2 ~ 0.5m
3/ rise catalyzer Lh;
Described catalyzer is P-V-Mo-Cr-K-O/ γ-Al
2o
3;
In described catalyzer, the soluble salt of activeconstituents is ammonium meta-vanadate, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood.
Described catalyzer adopts pickling process to prepare.
The soluble salt ammonium meta-vanadate of activeconstituents, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood are made into homogeneous solution, by carrier γ-Al by the preparation method of described catalyzer
2o
3be immersed, ageing under room temperature, put into electric furnace after oven dry and activate, obtain catalyzer.
The rate that supports of described catalyzer is 5-12%, is preferably 6%.
Compared with prior art, the inventive method is reasonable in design, workable, overall yield is high, have employed brand-new titanium oxide and aluminum oxide mixed carrier prepares novel fixed bed beaded catalyst, obtains good effect, make 2,6-toluene dichloride transformation efficiency reaches 99.5%, 2,6-dichlorobenzonitrile molar yield and reaches 95.0%.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but protection scope of the present invention is not limited to this.
Embodiment 1
The method of a kind of ammonia oxidation synthesis 2,6-dichlorobenzonitrile, the method with 2,6-DCT, ammonia, air for raw material, loading catalyst in fixed bed, temperature 350 DEG C, under pressure 0.02MPa condition, one-step synthesis 2,6-dichlorobenzonitrile; The mol ratio of raw material is 2,6-DCT: ammonia=1: 2.8, and mark state air capacity is 0.2m
3/ rise catalyzer Lh;
The soluble salt ammonium meta-vanadate of activeconstituents, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood are made into homogeneous solution, by carrier γ-Al by the preparation method of described catalyzer
2o
3be immersed, ageing under room temperature, put into electric furnace and activate, obtain catalyzer after oven dry, the rate of supporting is 8%;
Technological process is as follows: control fixed bed catalyst temperature 365 ± 1 DEG C, pre-mixing unstripped gas temperature 210 ± 10 DEG C, fixed-bed pressure 0.045MPa, opens spray absorber trapping product; Air flow quantity 112m
3/ h (mark state), ammonia flow 8.46m
3/ h (mark state, 357.8mol), 2,6-DCT 12.8 ㎏/h (79.5mol).Trapping product, by liquid chromatography external standard method content and purity, 2,6-DCT transformation efficiency reaches 99.2%, 2,6-dichlorobenzonitrile molar yield and reaches 93.1%.
Embodiment 2
The method of a kind of ammonia oxidation synthesis 2,6-dichlorobenzonitrile, the method with 2,6-DCT, ammonia, air for raw material, loading catalyst in fixed bed, temperature 350 DEG C, under pressure 0.02MPa condition, one-step synthesis 2,6-dichlorobenzonitrile; The mol ratio of raw material is 2,6-DCT: ammonia=1: 2.8, and mark state air capacity is 0.2m
3/ rise catalyzer Lh;
The soluble salt ammonium meta-vanadate of activeconstituents, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood are made into homogeneous solution, by carrier γ-Al by the preparation method of described catalyzer
2o
3be immersed, ageing under room temperature, put into electric furnace and activate, obtain catalyzer after oven dry, the rate of supporting is 6%;
Technological process is as follows: control fixed bed catalyst temperature 365 ± 1 DEG C, pre-mixing unstripped gas temperature 210 ± 10 DEG C, fixed-bed pressure 0.045MPa, opens spray absorber trapping product; Air flow quantity 112m
3/ h (mark state), ammonia flow 8.46m
3/ h (mark state, 357.8mol), 2,6-DCT 12.8 ㎏/h (79.5mol).Trapping product, by liquid chromatography external standard method content and purity, 2,6-DCT transformation efficiency reaches 99.5%, 2,6-dichlorobenzonitrile molar yield and reaches 95.0%.
Embodiment 3
The method of a kind of ammonia oxidation synthesis 2,6-dichlorobenzonitrile, the method with 2,6-DCT, ammonia, air for raw material, loading catalyst in fixed bed, temperature 350 DEG C, under pressure 0.02MPa condition, one-step synthesis 2,6-dichlorobenzonitrile; The mol ratio of raw material is 2,6-DCT: ammonia=1: 2.8, and mark state air capacity is 0.2m
3/ rise catalyzer Lh;
The soluble salt ammonium meta-vanadate of activeconstituents, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood are made into homogeneous solution, by carrier γ-Al by the preparation method of described catalyzer
2o
3be immersed, ageing under room temperature, put into electric furnace and activate, obtain catalyzer after oven dry, the rate of supporting is 12%;
Technological process is as follows: control fixed bed catalyst temperature 365 ± 1 DEG C, pre-mixing unstripped gas temperature 210 ± 10 DEG C, fixed-bed pressure 0.045MPa, opens spray absorber trapping product; Air flow quantity 112m
3/ h (mark state), ammonia flow 8.46m
3/ h (mark state, 357.8mol), 2,6-DCT 12.8 ㎏/h (79.5mol).Trapping product, by liquid chromatography external standard method content and purity, 2,6-DCT transformation efficiency reaches 98.7%, 2,6-dichlorobenzonitrile molar yield and reaches 91.4%.
Claims (6)
1. the method for ammonia oxidation synthesis 2, a 6-dichlorobenzonitrile, is characterized in that: the method is with 2,6-toluene dichloride, ammonia, air are raw material, loading catalyst in fixed bed, temperature 350 ~ 375 DEG C, under pressure 0.02 ~ 0.1MPa condition, one-step synthesis 2,6-dichlorobenzonitrile; The mol ratio of raw material is 3,4-toluene dichloride: ammonia=1: 2.8 ~ 5, and mark state air capacity is 0.2 ~ 0.5m
3/ rise catalyzer Lh;
Described catalyzer is P-V-Mo-Cr-K-O/ γ-Al
2o
3.
2. the method for ammonia oxidation synthesis according to claim 12,6-dichlorobenzonitrile, is characterized in that: in described catalyzer, the soluble salt of activeconstituents is ammonium meta-vanadate, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood.
3. the method for ammonia oxidation synthesis according to claim 12,6-dichlorobenzonitrile, is characterized in that: described catalyzer adopts pickling process to prepare.
4. the ammonia oxidation synthesis 2 according to any one of claim 1-3, the method of 6-dichlorobenzonitrile, it is characterized in that: the soluble salt ammonium meta-vanadate of activeconstituents, ammonium molybdate, ammonium chromate, phosphoric acid, salt of wormwood are made into homogeneous solution, by carrier γ-Al by the preparation method of described catalyzer
2o
3be immersed, ageing under room temperature, put into electric furnace after oven dry and activate, obtain catalyzer.
5. the method for ammonia oxidation synthesis 2, the 6-dichlorobenzonitrile according to any one of claim 1-3, is characterized in that: the rate that supports of described catalyzer is 5-12%.
6. the method for ammonia oxidation synthesis 2, the 6-dichlorobenzonitrile according to any one of claim 1-3, is characterized in that: the rate that supports of described catalyzer is 6%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410683052.3A CN104326940A (en) | 2014-11-24 | 2014-11-24 | Method for synthesizing 2,6-dichlorobenzonitrile by ammoxidation |
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|---|---|---|---|
| CN201410683052.3A CN104326940A (en) | 2014-11-24 | 2014-11-24 | Method for synthesizing 2,6-dichlorobenzonitrile by ammoxidation |
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|---|---|
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109046454A (en) * | 2018-08-23 | 2018-12-21 | 常州新日催化剂有限公司 | It is a kind of for synthesizing the catalyst and preparation method thereof of 2,6- dichlorobenzonitrile |
| CN111233705A (en) * | 2020-03-02 | 2020-06-05 | 南京工业大学 | Method for preparing corresponding benzonitrile by virtue of benzyl chloride derivative ammoxidation method |
| CN115646520A (en) * | 2022-11-15 | 2023-01-31 | 江苏新河农用化工有限公司 | Catalyst for synthesizing parachlorobenzonitrile and preparation method and application thereof |
| CN115819275A (en) * | 2022-12-28 | 2023-03-21 | 济宁正东化工有限公司 | Preparation method of 2, 6-dichlorobenzonitrile |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109046454A (en) * | 2018-08-23 | 2018-12-21 | 常州新日催化剂有限公司 | It is a kind of for synthesizing the catalyst and preparation method thereof of 2,6- dichlorobenzonitrile |
| CN109046454B (en) * | 2018-08-23 | 2022-11-18 | 常州新日催化剂股份有限公司 | Catalyst for synthesizing 2, 6-dichlorobenzonitrile and preparation method thereof |
| CN111233705A (en) * | 2020-03-02 | 2020-06-05 | 南京工业大学 | Method for preparing corresponding benzonitrile by virtue of benzyl chloride derivative ammoxidation method |
| CN115646520A (en) * | 2022-11-15 | 2023-01-31 | 江苏新河农用化工有限公司 | Catalyst for synthesizing parachlorobenzonitrile and preparation method and application thereof |
| CN115646520B (en) * | 2022-11-15 | 2024-05-14 | 江苏新河农用化工有限公司 | Catalyst for synthesizing p-chlorobenzonitrile and preparation method and application thereof |
| CN115819275A (en) * | 2022-12-28 | 2023-03-21 | 济宁正东化工有限公司 | Preparation method of 2, 6-dichlorobenzonitrile |
| CN115819275B (en) * | 2022-12-28 | 2024-05-14 | 济宁正东化工有限公司 | Preparation method of 2, 6-dichlorobenzonitrile |
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Application publication date: 20150204 |