CN101250115B - Method for synthesizing 3-amido-1,2-propanediol by pipe reactor - Google Patents
Method for synthesizing 3-amido-1,2-propanediol by pipe reactor Download PDFInfo
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- CN101250115B CN101250115B CN2008100602551A CN200810060255A CN101250115B CN 101250115 B CN101250115 B CN 101250115B CN 2008100602551 A CN2008100602551 A CN 2008100602551A CN 200810060255 A CN200810060255 A CN 200810060255A CN 101250115 B CN101250115 B CN 101250115B
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 19
- 239000003513 alkali Substances 0.000 claims abstract description 16
- 230000009615 deamination Effects 0.000 claims abstract description 12
- 238000006481 deamination reaction Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 9
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 45
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 45
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- 238000002156 mixing Methods 0.000 claims description 27
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims description 18
- 235000011187 glycerol Nutrition 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 8
- 238000004176 ammonification Methods 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 230000003472 neutralizing effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- -1 3-amino-1 Chemical class 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a method for synthesizing 3-amino-1, 2-propanediol via a tubular reactor, which comprises (1) ammoniation such as premixing liquid chlorine glycerol and ammonia water via a mixer, and reacting in a tubular reactor while the reaction temperature is 60-100DEG C, the pressure is 3-6MPa and the time is 6-12min, and obtain the mixture solution of 3-amino-1, 2-propanediol and ammonia water, (2) purification such as treating the mixture solution by depressurizing, flash evaporation and deamination, and treating the liquid after the deamination by adding alkali to neutralize, dehydrating, depressurizing and distilling, to obtain 3-amino-1, 2-propanediol. The synthesized 3-amino-1, 2-propanediol has the advantages of high yield.
Description
Technical field
The present invention relates to a kind of method of using the pipeline reactor synthetic compound, particularly 3-amino-1, the duct type synthesis method of 2-propylene glycol.
Background technology
CH
2ClCHOHCH
2OH+NH
3—→CH
2NH
2CHOHCH
2OH
CH
2NH
2CHOHCH
2OH+CH
2ClCHOHCH
2OH—→(CH
2OHCHOHCH
2)
2NH
S-2
The 3-amino-1 of molecular formula shown in S-1, the 2-propylene glycol is widely used in agricultural chemicals, medicine and other fields, is the important intermediate of synthetic non-ionic contrast agent.3-amino-1, the 2-propylene glycol is mainly obtained by the glycerin chlorohydrin ammonification, and reaction formula is shown in S-2.From reaction, outside the 2-propylene glycol, also there is the series connection side reaction except target product 3-amino-1 in the glycerin chlorohydrin aminating reaction simultaneously, generates two (2, the 3-dihydroxypropyl) amine of by product even uncle (2, the 3-dihydroxypropyl) amine.Present production technique mainly adopts tank reactor, is reflected under the full silver mixing spare to carry out, and produces more secondary amine and tertiary amine, has reduced product selectivity.
Be reported in adding glycerin chlorohydrin and ammoniacal liquor in the there-necked flask as patent CN1132739A, 80 ℃ were reacted 3 hours down, remove excess of ammonia water under reduced pressure, methanol solution with sodium hydroxide neutralizes then, remove by filter insolubles, 165～168 ℃/5mmHg cut, product yield 57.1% are collected in underpressure distillation.Patent USP4360697 is reported in the autoclave, and 85 ℃ of temperature of reaction under the pressure 4MP condition, are solvent with toluene, adds glycerin chlorohydrin and liquefied ammonia, reacts yield 53.5% 4 hours.Its shortcoming is that reaction preference is bad equally, and by product is more.
Summary of the invention
The technical problem to be solved in the present invention provides the synthetic 3-amino-1 of the higher pipeline reactor of a kind of yield, the method for 2-propylene glycol.
In order to solve the problems of the technologies described above, the invention provides the synthetic 3-amino-1 of a kind of pipeline reactor, the method for 2-propylene glycol comprises the steps:
1), ammonification: the glycerin chlorohydrin of liquid phase and ammoniacal liquor enter the pipeline reactor reaction then earlier through the mixing tank premix, and temperature of reaction is 60～100 ℃, and pressure is 3～6MPa, and the time is 6～12min, obtains 3-amino-1, the mixing solutions of 2-propylene glycol and ammoniacal liquor; The mol ratio of ammonia and glycerin chlorohydrin is 10～30: 1;
2), purify: above-mentioned mixing solutions is returned deamination through vacuum flashing; The liquid of then above-mentioned deamination being handled the back gained adds alkali neutralization, dehydration and rectification under vacuum successively, gets 3-amino-1, the 2-propylene glycol.
As the synthetic 3-amino-1 of pipeline reactor, the improvement of the method for 2-propylene glycol: the flow velocity of reactant in pipeline reactor is 1.9l/h～3.8l/h.
As the synthetic 3-amino-1 of pipeline reactor, the further improvements in methods of 2-propylene glycol: in the step 1), the concentration of ammonia is 30%wt～100%wt in the ammoniacal liquor.
As the synthetic 3-amino-1 of pipeline reactor, the further improvements in methods of 2-propylene glycol: the mixing tank in the step 1) is a static mixer.
As the synthetic 3-amino-1 of pipeline reactor, the further improvements in methods of 2-propylene glycol: step 2), the mol ratio of alkali and glycerin chlorohydrin is 1～3: 1, and alkali is mineral alkali, for example is potassium hydroxide, sodium hydroxide, calcium hydroxide, salt of wormwood or yellow soda ash etc.
The present invention is the principle analysis from chemical reaction engineering, is the reaction system of the intermediate of successive reaction for target product, adopts the flat push type reactor more reasonable, and is favourable to improving target product selectivity and reducing by product.
Pipeline reactor of the present invention synthesizes 3-amino-1, the method for 2-propylene glycol, compared with prior art,
Have the following advantages:
1, the reaction times weak point utilizes pipeline reactor to synthesize 3-amino 1, and the 2-propylene glycol reaction times is 6～12min, and it is 2～3 hours that document (CN1132739A) is introduced the technological reaction time.
2, yield height utilizes pipeline reactor to synthesize 3-amino 1, the 2-propylene glycol, and product yield can reach 71.3%, and it is 57.1% that document (CN1132739A) is introduced the handicraft product yield.
Description of drawings
Below in conjunction with accompanying drawing the specific embodiment of the present invention is described in further detail.
Fig. 1 is the synthetic 3-amino-1 of pipeline reactor of the present invention, the reacting flow chart of the method for 2-propylene glycol.
Embodiment
Embodiment 1, the synthetic 3-amino-1 of a kind of pipeline reactor, the method for 2-propylene glycol, carry out following steps successively:
1), ammonification, i.e. 3-amino-1, the preparation of the mixing solutions of 2-propylene glycol and ammoniacal liquor:
The ammoniacal liquor of 40%wt in the glycerin chlorohydrin 55g (0.5mol) of the liquid phase in the storage tank I 1 and the storage tank II 2, premix in mixing tank 3 forms reactant earlier, and the mol ratio of glycerin chlorohydrin and ammonia is 1: 10, and mixing tank 3 is a static mixer.With volume pump 10 reactant is sent in the pipeline reactor 4 then and reacted, 70 ℃ of temperature of reaction, reaction pressure 4Mpa, pipeline reactor 4 are that an internal diameter is that 4mm, length are the drum type brake reactor of 30m; The flow of control volume pump 10, making reactant is 3.2l/h at the flow velocity of pipeline reactor 4, even the reaction times is about 7min; Finally obtain 3-amino-1, the mixing solutions of 2-propylene glycol and ammoniacal liquor.
2), purify, i.e. 3-amino-1, the preparation of 2-propylene glycol:
Above-mentioned from pipeline reactor 4 effusive mixing solutions enter flashing tower 5 and carry out vacuum flashing, to remove most ammonia, promptly reclaim excess of ammonia; The condition of vacuum flashing is specific as follows: pipeline reactor 4 effusive mixing solutionss become superheated liquid through after reducing pressure, and unnecessary sensible heat discharges and makes most of light constituent ammonia evaporate from solution.
The ammonia that vacuum flashing produced enters recovery tower 6 and is recovered, and the liquid of gained enters neutralizing well 7 and carries out neutralizing treatment after the vacuum flashing.Placed potassium hydroxide solution in the neutralizing well 7, the amount of potassium hydroxide is 30g.
The liquid of gained is introduced into dehydration tower 8 after the neutralizing treatment, thereby removes big water gaging and little ammonia; Enter rectifying tower 9 at last and carry out rectification process, collect cut under the 164-166/5mmHg, finally obtain purity at the 3-amino-1 more than 99%, 2-propylene glycol, product yield 61.3%.
Embodiment 2, the synthetic 3-amino-1 of a kind of pipeline reactor, the method for 2-propylene glycol, used device specifically carries out following steps successively with embodiment 1:
1), ammonification, i.e. 3-amino-1, the preparation of the mixing solutions of 2-propylene glycol and ammoniacal liquor:
With glycerin chlorohydrin 55g (0.5mol) and ammoniacal liquor (80%wt) with 1: 15 mol ratio (being the mol ratio of glycerin chlorohydrin and ammonia) thorough mixing after, react, 90 ℃ of temperature of reaction, reaction pressure 6Mpa, reactant is 2.3l/h at the flow velocity of pipeline reactor 4, and promptly controlling reaction time is about 10min; Get 3-amino-1, the mixing solutions of 2-propylene glycol and ammoniacal liquor.
2), purify, i.e. 3-amino-1, the preparation of 2-propylene glycol:
Above-mentioned mixing solutions is returned deamination through vacuum flashing; The liquid of then above-mentioned deamination being handled the back gained adds the alkali neutralization successively, and (alkali is selected sodium hydroxide solution for use, the amount of sodium hydroxide is 40g), dehydration and rectification under vacuum, collect cut under the 164-166/5mmHg, obtain purity at the 3-amino-1 more than 99%, the 2-propylene glycol, product yield 66.3%.
Embodiment 3, the synthetic 3-amino-1 of a kind of pipeline reactor, the method for 2-propylene glycol, used device specifically carries out following steps successively with embodiment 1:
1), ammonification, i.e. 3-amino-1, the preparation of the mixing solutions of 2-propylene glycol and ammoniacal liquor:
With glycerin chlorohydrin 55g (0.5mol) and ammoniacal liquor (40%wt) with 1: 30 mol ratio (being the mol ratio of glycerin chlorohydrin and ammonia) thorough mixing after, react, 80 ℃ of temperature of reaction, reaction pressure 4Mpa, reactant is about 1.9l/h at the flow velocity of pipeline reactor 4, and promptly controlling reaction time is 12min; Get 3-amino-1, the mixing solutions of 2-propylene glycol and ammoniacal liquor.
2), purify, i.e. 3-amino-1, the preparation of 2-propylene glycol:
Above-mentioned mixing solutions is returned deamination through vacuum flashing; The liquid of then above-mentioned deamination being handled the back gained adds the alkali neutralization successively, and (alkali is selected solution of potassium carbonate for use, the amount of salt of wormwood is 60g), dehydration and rectification under vacuum, collect cut under the 164-166/5mmHg, obtain purity at the 3-amino-1 more than 99%, the 2-propylene glycol, product yield 71.3%.
Embodiment 4, the synthetic 3-amino-1 of a kind of pipeline reactor, the method for 2-propylene glycol, used device specifically carries out following steps successively with embodiment 1:
1), ammonification, i.e. 3-amino-1, the preparation of the mixing solutions of 2-propylene glycol and ammoniacal liquor:
With glycerin chlorohydrin 55g (0.5mol) and liquefied ammonia with 1: 20 mol ratio (being the mol ratio of glycerin chlorohydrin and ammonia) thorough mixing after, react 70 ℃ of temperature of reaction, reaction pressure 6Mpa, reactant is 2.3l/h at the flow velocity of pipeline reactor 4, and promptly controlling reaction time is about 10min; Get 3-amino-1, the mixing solutions of 2-propylene glycol and ammonia.
2), purify, i.e. 3-amino-1, the preparation of 2-propylene glycol:
Above-mentioned mixing solutions is returned deamination through vacuum flashing; The liquid of then above-mentioned deamination being handled the back gained adds the alkali neutralization successively, and (alkali is selected solution of potassium carbonate for use, the amount of salt of wormwood is 70g), dehydration and rectification under vacuum, collect cut under the 164-166/5mmHg, obtain purity at the 3-amino-1 more than 99%, the 2-propylene glycol, product yield 68.6%.
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (6)
1. a pipeline reactor synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that comprising the steps:
1), ammonification: the glycerin chlorohydrin of liquid phase and ammoniacal liquor/liquefied ammonia enters the pipeline reactor reaction then earlier through the mixing tank premix, and temperature of reaction is 60～100 ℃, pressure is 3～6MPa, time is 6～12min, obtains 3-amino-1, the mixing solutions of 2-propylene glycol and ammoniacal liquor; The mol ratio of ammonia and glycerin chlorohydrin is 10～30: 1;
2), purify: above-mentioned mixing solutions is returned deamination through vacuum flashing; The liquid of then above-mentioned deamination being handled the back gained adds alkali neutralization, dehydration and rectification under vacuum successively, gets 3-amino-1, the 2-propylene glycol.
2. pipeline reactor according to claim 1 synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that: the volumetric flow rate of reactant in pipeline reactor is 1.9l/h～3.8l/h.
3. pipeline reactor according to claim 2 synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that: the mixing tank in the described step 1) is a static mixer.
4. pipeline reactor according to claim 3 synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that: described step 2), the mol ratio of alkali and glycerin chlorohydrin is 1～3: 1.
5. pipeline reactor according to claim 4 synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that: described step 2), alkali is mineral alkali.
6. pipeline reactor according to claim 5 synthesizes 3-amino-1, and the method for 2-propylene glycol is characterized in that: described mineral alkali is potassium hydroxide, sodium hydroxide or calcium hydroxide.
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| CN2008100602551A CN101250115B (en) | 2008-04-01 | 2008-04-01 | Method for synthesizing 3-amido-1,2-propanediol by pipe reactor |
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| CN2008100602551A CN101250115B (en) | 2008-04-01 | 2008-04-01 | Method for synthesizing 3-amido-1,2-propanediol by pipe reactor |
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101648881B (en) * | 2009-09-03 | 2013-08-21 | 青岛中科荣达新材料有限公司 | New synthesis process of aminoglycerol |
| CN101993381B (en) * | 2010-10-27 | 2013-05-08 | 西安近代化学研究所 | Synthetic method of 3-amino-1, 2-propanediol |
| CN101973888B (en) * | 2010-10-30 | 2013-11-06 | 西安近代化学研究所 | Preparation method of 2,2,2-trifluoroethylamine |
| NO332670B1 (en) | 2011-02-10 | 2012-12-03 | Borregaard As | Process for the preparation of amino alcohols |
| CN103012164B (en) * | 2012-12-26 | 2014-12-31 | 上海安诺芳胺化学品有限公司 | Method for continuously producing m-diethylaminophenol through channelization |
| CN103319354B (en) * | 2013-05-14 | 2015-03-25 | 西安近代化学研究所 | Synthesis method of 3-amino-1,2-propanediol |
| CN103319353B (en) * | 2013-05-14 | 2014-07-16 | 西安近代化学研究所 | Catalyzed synthesis method of 3-amino-1, 2-propylene glycol |
| CN104130140B (en) * | 2014-08-06 | 2016-04-13 | 内蒙古圣氏化学有限公司 | By the method for continuous reacting device synthesis 3-amino-1,2-PD |
| CN111302957A (en) * | 2020-03-02 | 2020-06-19 | 杭州沈氏节能科技股份有限公司 | Preparation method of amino glycerol |
| CN113754548A (en) * | 2021-10-26 | 2021-12-07 | 合肥工业大学 | Preparation method of 3-aminopropanol |
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| CN1128018A (en) * | 1993-06-30 | 1996-07-31 | 普罗格特-甘布尔公司 | Reductive alkylation of amine to make tertiary amino polyol as precursor of fabric softening esters |
| CN1132739A (en) * | 1995-11-20 | 1996-10-09 | 江苏省原子医学研究所 | Prepn of polyhydric alcohol amine |
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Patent Citations (2)
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|---|---|---|---|---|
| CN1128018A (en) * | 1993-06-30 | 1996-07-31 | 普罗格特-甘布尔公司 | Reductive alkylation of amine to make tertiary amino polyol as precursor of fabric softening esters |
| CN1132739A (en) * | 1995-11-20 | 1996-10-09 | 江苏省原子医学研究所 | Prepn of polyhydric alcohol amine |
Non-Patent Citations (1)
| Title |
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| 张福根等.非离子型X射线造影剂中间体1-氨基-2,3-丙二醇的合成.精细化工15卷 6期.1998,15卷(6期),第35-37页. * |
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Address after: 317016 coastal industrial zone, Linhai City, Zhejiang Province Patentee after: Zhejiang Haizhou Pharmaceutical Co.,Ltd. Address before: 317016 coastal industrial zone, Linhai City, Zhejiang Province Patentee before: ZHEJIANG HAIZHOU PHARMACEUTICAL CO.,LTD. |