CN106380385A - Method for preparing cycloheptanone from cyclohexanone through one step - Google Patents
Method for preparing cycloheptanone from cyclohexanone through one step Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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Abstract
A method for preparing cycloheptanone from cyclohexanone through one step comprises the following steps: using diazomethane as a reagent to prepare a saturated low alcohol solution, adding cyclohexanone and a diluted acid catalyst to a diazomethane alcohol solution, carrying out a slow addition ring expansion reaction at 10-50 DEG C, and carrying out water vapor distillation to prepare crude cycloheptanone; and rectifying the crude cycloheptanone to obtain cycloheptanone. A saturated C4 or less low alcohol solution of diazomethane is prepared through the following steps: reacting hydrochloric acid with a methylamine solution, adding urea, adding a saturated sodium carbonate solution, carrying out a refluxing reaction, adding diluted sulfuric acid, reacting sulfuric acid with a sodium nitrite solution, adding a strong alkali solution to generate a diazomethane gas, introducing the diazomethane gas to a cooled receiving bottle provided with the C4 or less low alcohol. The method has the advantages of short synthetic route, simplicity in operation, environmental protection, high product yield, substantial reduction of the cost, and high facilitation of industrial production.
Description
Technical field
The invention belongs to the preparation technology of medicine intermediate is and in particular to a kind of antihypertensive drug guanethidine sulfate
The preparation method of intermediate cycloheptanone.
Background technology
Cycloheptanone is a kind of key intermediate producing antihypertensive drug guanethidine sulfate, is also used for synthesizing heptan simultaneously
Multiple organic fine chemicals such as diacid, wide market.
The conventional production methods of cycloheptanone, are with Ketohexamethylene as raw material, through nitromethane addition, neutralization, iron powder reducing, weight
The reaction of nitridation, ring expansion etc. five step is obtained, and its process route is shown in accompanying drawing 1.The wherein technique waste water such as neutralization, iron powder reducing, diazotising
More and not disposable, easily pollute environment.Iron powder and hydrochloric acid is especially used to reduce nitro, equipment requirements are high, the iron cement of generation is difficult
Process, this method has synthetic route length, complex operation, synthesis yield is low, environmental protection treatment is difficult, production cost is high etc. many lacks
Fall into.
Content of the invention
It is an object of the invention to provide a kind of preparation method of new cycloheptanone, it is to avoid technological operation in conventional production methods
Complicated, many defects such as synthesis yield is low, environmental protection treatment is difficult, production cost is high.It is also with Ketohexamethylene as raw material, by a step
Cycloheptanone is synthesized, this method synthetic route is short, technological operation is easy, production economy environmental protection, suitable industrialized production.
The technical scheme is that：The method that Ketohexamethylene one-step method prepares cycloheptanone, makees reagent preparation with Azimethylene.
Lower alcohol saturated solution, Ketohexamethylene, in below C4 lower alcohol saturated solution, slowly reacts in 10～50 DEG C, so under weak acid catalysis
After carry out steam distillation, prepared cycloheptanone crude product, cycloheptanone crude product obtains cycloheptanone through rectification again.
Concrete operation step is：
A, prepare Azimethylene. below C4 lower alcohol saturated solution method, it is characterized in that：By concentration at -10～10 DEG C
36% hydrochloric acid slowly drops to equipped with the reaction bulb of methylamine solution, until system pH=6～7, is subsequently adding carbamide, stirs 8-
10 minutes, add saturated sodium carbonate solution, slowly heat up, back flow reaction 4～6 hours, detection pH=7～8 after having reacted, so
Afterwards system is cooled to the dilute sulfuric acid of 20～25 DEG C of addition concentration 26-27%, further cools to 0 DEG C, slowly Deca is joined in advance
The sodium nitrite solution of good concentration 38%, after 1-1.5 hour drips off, stirring 0.5-1 hour makes reaction complete；In another gas
Below C4 lower alcohol is added, ice salt bath is placed in outside makes temperature in bottle be maintained at -10-0 DEG C, installs vent gas treatment in receiving flask
Device, UNICOM's reaction bulb and gas receiving flask, the seal of inspection system, start blender, at 20-40 DEG C after being ready to complete
The strong base solution of slowly Deca concentration 50% in reaction bulb, until Azimethylene. absorbs saturation, its content 18.5- in receiving flask
25.5%, close intercommunicating device, obtain Azimethylene. alcohol saturated solution；
Weight proportion between reactant is：40% methylamine：Concentrated hydrochloric acid：Carbamide：Sodium carbonate：Sulphuric acid：Sodium nitrite：Highly basic：Water=1：
1.00-1.25：0.95-1.05: 0.20-0.30：0.80-0.85：0.9-1.0:1.15-1.25:5.8-6.0；Reactant and weight
Proportioning between formylmerphalan alkane lyosoption is, 40% methylamine solution：Organic solvent=1g：4～8ml.
B, prepare cycloheptanone crude product：Add Ketohexamethylene and aqueous acid, pH=5.5 ~ 6.5 in Deca bottle, be positioned over
State on receiving flask；The slowly Deca Ketohexamethylene aqueous acid when temperature is at 10～50 DEG C in receiving flask, controls time for adding 2.5 ~ 3
Hour, drip off follow-up continuous insulation reaction 1.5 ~ 2 hours, reacted rear recovered under reduced pressure organic solvent, then carried out steam distillation,
Obtain cycloheptanone crude product, weight yield 90～95%, G/C content 65～70%；Reaction residue and vinasse all can be applied mechanically.
C, cycloheptanone crude product rectification obtain cycloheptanone：Under 5 ~ 10mmHg post vacuum, collect 102 ~ 105 DEG C of fractions, obtain cycloheptyl
Ketone；Content 99.0 ~ 99.5%, rectification weight yield 50-55%；Distillation residual liquid can be applied mechanically;In terms of the Equilibrium yield applied mechanically, synthesis
Weight total recovery 75 ~ 80%.
Above-mentioned below C4 low-carbon alcohols include methanol, ethanol, isopropanol；Acid catalyst includes the hydrochloric acid of mineral acid, sulphuric acid, phosphorus
Acid, or the acetic acid of organic acid, p-methyl benzenesulfonic acid, oxalic acid；The inorganic strong alkali solution of Deca includes sodium hydroxide solution, hydroxide
Potassium；Methylamine salt is -10～0 DEG C with methylamine urea reaction temperature, and Azimethylene. reacts temperature for 20～40 DEG C；Described sour water is molten
Liquid includes hydrochloric acid or the sulphuric acid of mineral acid, or the acetic acid of organic acid or p-methyl benzenesulfonic acid, sour water concentration 1%；Addition ring expansion
10～50 DEG C of reaction temperature, reactant Ketohexamethylene is 1g with the proportioning of Azimethylene. alcoholic solution：2.5~3.5ml.
Further preferably scheme, low-carbon alcohols ethanol, acid catalyst acetic acid, inorganic strong alkali sodium hydroxide solution, weight
The formylmerphalan alkane temperature that reacts is 25～30 DEG C；Weight proportion between reactant is：40% methylamine：Concentrated hydrochloric acid：Carbamide：Sodium carbonate：
Concentrated sulphuric acid：Sodium nitrite：Highly basic：Water=1:1.15 :1:0.26: 0.825: 0.95:1.2:5.9；Addition ring expansion anti-
Temperature is answered to be 30-35 DEG C；Ketohexamethylene is 1g with the proportioning of Azimethylene. alcoholic solution：3ml.
The invention has the beneficial effects as follows：Cycloheptanone is prepared using the inventive method, relatively conventional conventional production methods, tool
There is synthetic route short, production operation is easy, environmental friendly, many advantages, such as product yield is high, cost can be significantly reduced.In technique
The solvent using, recyclable recycled, both economical, and environmental protection, it is very beneficial to industrialized production.
Brief description
The synthetic route chart of Fig. 1 tradition cycloheptanone；
Fig. 2 cycloheptanone of the present invention synthetic route chart.
Specific embodiment
In order to main points and the spirit of the present invention are more easily described, citing below is explained：
Embodiment one：
A, prepare the alcohol saturated solution of Azimethylene.
In one 1000ml there-necked flask, add 100g 40% methylamine solution, after system temperature is down to -5～0 DEG C, by 36% salt
Sour 114g slowly drops in methylamine solution, until system pH=6～7, is subsequently adding 100g carbamide, stir about 10 minutes, then plus
Enter and the saturated sodium carbonate solution that 4ml water is made into is converted by 2.6g sodium carbonate, be slowly ramped to flow back, maintain the reflux for reacting 4～6 little
When, after having reacted, detect pH about 7-8, then system temperature is down to 20～25 DEG C, add 50ml tap water, add by
Dilute sulfuric acid that is that 82.5g concentrated sulphuric acid is made into 225ml tap water and being cooled to 5-10 DEG C, is further down to -5～0 DEG C, keeps
For 0 DEG C, what slowly Deca prepared in advance converts, by 95g sodium nitrite, the sodium nitrite solution that 155ml tap water is made and cooled down, about
Drip off within 1～1.5 hour, after dripping off, continuing stirring at 0～5 DEG C makes reaction complete in 0.5～1 hour.Another one 1000ml tri- of device
Mouth bottle, as Azimethylene. gas receiving flask, is added thereto to 600ml ethanol, and ice salt bath is placed in outside, so that temperature in bottle is kept
At -10～0 DEG C, install exhaust gas processing device, UNICOM's reaction bulb and gas receiving flask, the seal of inspection system, prepared
Cheng Hou, starts to stir, at 20-40 DEG C in reaction bulb slowly Deca ready 240g50% sodium hydroxide solution, until connecing
Absorbed saturation, its content about 22.5% by Azimethylene. in bottle, then, reaction bulb stops Deca alkali liquor, closes intercommunicating device, obtains
Azimethylene. alcoholic solution, in case the next step uses.
B, prepare cycloheptanone crude product
On the Azimethylene. receiving flask of above-mentioned 1000ml, load onto a 500ml Deca bottle, be added thereto to 200ml hexamethylene
Ketone and the aqueous hydrochloric acid solution of 5ml 1%, make pH5.5～6.5, standby；When above-mentioned receiving flask keeps internal temperature at 10～20 DEG C, open
Begin slowly Deca Ketohexamethylene aqueous acid, controls time for adding about 2.5～3 hours, and after dripping off, regulating and controlling temperature continues to 30-35 DEG C
Continuous reaction 1.5～2 hours, after having reacted, the ethanol of recovered under reduced pressure about 95%, then carry out vapor distillation, obtain cycloheptanone crude product
186ml, weight yield 93%, G/C content 68.5%.Reaction residue and vinasse all can be applied mechanically.
C, prepare cycloheptanone
In a 1000ml there-necked flask, add 100g cycloheptanone crude product, load onto rectifier unit, open vacuum, be slowly ramped to
80～84 DEG C, first reclaim Ketohexamethylene, then control and collect 101～103 DEG C of fractions under 5～10mm Hg post vacuum, obtain cycloheptanone
53.5g, G/C content 99.4%, yield 53.5%.Recovered liquid and rectification residual night apply mechanically.Convert weight yield 78.2 % by applying mechanically.
Embodiment two：
A, prepare the methanol saturated solution of Azimethylene.
In one 1000ml there-necked flask, add 100g 40% methylamine solution, after system temperature is down to -5～0 DEG C, by 114g
36% hydrochloric acid slowly drops in methylamine solution, until system pH=6-7, is subsequently adding 100g carbamide, stir about 10 minutes, then plus
Enter and the saturated sodium carbonate solution that 4ml water is made into converted by 2.6g sodium carbonate, be slowly ramped to flow back, maintain the reflux for reacting 4-6 hour,
After having reacted, detection pH is 7-8, then system temperature is down to 20～25 DEG C, adds 50ml tap water, adds by 82.5g
Dilute sulfuric acid that is that concentrated sulphuric acid is made into 225ml tap water and being cooled to 5-10 DEG C, is further down to -5～0 DEG C, keeps about 0
DEG C, what slowly Deca prepared in advance converts the sodium nitrite solution that 155ml tap water is made and cooled down, about 1- by 95g sodium nitrite
Drip off within 1.5 hours, after dripping off, continuing stirring 0.5-1 hour at 0～5 DEG C makes reaction complete.Another one 1000ml there-necked flask of device
As Azimethylene. gas receiving flask, be added thereto to 600ml methanol, ice salt bath is placed in outside, make temperature in bottle be maintained at-
10～0 DEG C, install exhaust gas processing device, UNICOM's reaction bulb and gas receiving flask, the seal of inspection system, be ready to complete
Afterwards, start stirring, at 20～40 DEG C, the slowly ready 50% potassium hydroxide solution 240g of Deca in reaction bulb, until
In receiving flask, Azimethylene. absorbs saturation, its content about 20.5%, and then, reaction bulb stops Deca alkali liquor, closes intercommunicating device,
Obtain Azimethylene. alcoholic solution, in case the next step uses.
B, prepare cycloheptanone crude product
On the Azimethylene. receiving flask of above-mentioned 1000ml, load onto a 500ml Deca bottle, be added thereto to 200ml hexamethylene
Ketone and 1% aqueous acetic acid 5ml, make pH be 5.5～6.5, standby；When above-mentioned receiving flask keeps internal temperature at 10-20 DEG C, start
Slowly Deca Ketohexamethylene aqueous acid, controls time for adding about 2.5～3 hours, and after dripping off, regulating and controlling temperature continues to 30～35 DEG C
Reaction 1.5～2 hours, after having reacted, the methanol of recovered under reduced pressure about 95%, then carry out vapor distillation, obtain cycloheptanone crude product
180ml, weight yield 90%, G/C content 66.2%.React residual night all can apply mechanically with distilling residual night.
C, prepare cycloheptanone
In a 1000ml there-necked flask, add 100g cycloheptanone crude product, load onto rectifier unit, open vacuum, be slowly ramped to
80～84 DEG C, first reclaim Ketohexamethylene, then control and collect 101～103 DEG C of fractions under 5～10mm Hg post vacuum, obtain cycloheptanone
50.5g, G/C content 99.2%, yield 50.5%.Recovered liquid and rectification residual night apply mechanically.Convert weight yield 75.8% by applying mechanically.
Embodiment three
A, prepare the isopropanol saturated solution of Azimethylene.
In one 1000ml there-necked flask, add the methylamine solution of 100g 40%, after system temperature is down to -5～0 DEG C, by 36% salt
Sour 114g slowly drops in methylamine solution, until system pH=6-7, is subsequently adding 100g carbamide, stir about 10 minutes, then plus
Enter and the saturated sodium carbonate solution that 4ml water is made into is converted by 2.6g sodium carbonate, be slowly ramped to flow back, maintain the reflux for reacting 4～6 little
When, after having reacted, detection pH be 7～8, then system temperature is down to 20～25 DEG C, add 50ml tap water, add by
Dilute sulfuric acid that is that 82.5g concentrated sulphuric acid is made into 225ml tap water and being cooled to 5～10 DEG C, is further down to -5～0 DEG C, protects
Hold about 0 DEG C, what slowly Deca prepared in advance converts, by 95g sodium nitrite, the sodium nitrite solution that 155ml tap water is made and cooled down,
Drip off within about 1～1.5 hour, after dripping off, continuing stirring at 0～5 DEG C makes reaction complete in 0.5～1 hour.Another one 1000ml of device
There-necked flask, as Azimethylene. gas receiving flask, is added thereto to 600ml isopropanol, and ice salt bath is placed in outside, makes temperature in bottle
It is maintained at -10～0 DEG C, install exhaust gas processing device, UNICOM's reaction bulb and gas receiving flask, the seal of inspection system, standard
After the completion of standby, start stirring, at 20～40 DEG C, the slowly ready 50% sodium hydroxide solution 240g of Deca in reaction bulb,
Until Azimethylene. absorbs saturation, its content about 25.5% in receiving flask, then, reaction bulb stops Deca alkali liquor, closes UNICOM's dress
Put, obtain the aqueous isopropanol of Azimethylene., in case the next step uses.
B, prepare cycloheptanone crude product
On the Azimethylene. receiving flask of above-mentioned 1000ml, load onto a 500ml Deca bottle, be added thereto to 200ml hexamethylene
Ketone and 1% aqueous sulfuric acid 5ml, make pH about 5.5～6.5, standby；When above-mentioned receiving flask keeps internal temperature at 10～20 DEG C, open
Begin slowly Deca Ketohexamethylene aqueous acid, controls time for adding about 2.5～3 hours, and after dripping off, regulating and controlling temperature continues to 30-35 DEG C
Continuous reaction 1.5～2 hours, after having reacted, the isopropanol of recovered under reduced pressure about 95%, then carry out vapor distillation, obtain cycloheptanone thick
Product 188.6ml, weight yield 94.3%, G/C content 69.5%.React residual night all can apply mechanically with distilling residual night.
C, prepare cycloheptanone
In a 1000ml there-necked flask, add 100g above-mentioned cycloheptanone crude product, load onto rectifier unit, open vacuum, slowly rise
Temperature, to 80～84 DEG C, first reclaims Ketohexamethylene, then controls and collect 101～103 DEG C of fractions under 5～10mm Hg post vacuum, obtain cycloheptyl
Ketone 55.0g, G/C content 99.5%, yield 55.0%.Recovered liquid and rectification residual night apply mechanically.Convert weight yield 79.6 % by applying mechanically.
Claims (6)
1. with Ketohexamethylene one-step method prepare cycloheptanone method it is characterised in that：Make reagent preparation below C4 with Azimethylene. low
Level alcohol saturated solution, add in Azimethylene. alcoholic solution Ketohexamethylene and diluted acid catalyst in 10～50 DEG C slowly addition ring expansion anti-
Should, then carry out steam distillation, prepared cycloheptanone crude product；Cycloheptanone crude product is obtained cycloheptanone through rectification again.
2. the method preparing below the C4 lower alcohol saturated solution of Azimethylene., is characterized in that：By concentration at -10～10 DEG C
36% hydrochloric acid slowly drops to equipped with the reaction bulb of methylamine solution, until system pH=6～7, is subsequently adding carbamide, stirs 8-
10 minutes, add saturated sodium carbonate solution, slowly heat up, back flow reaction 4～6 hours, detection pH=7～8 after having reacted, so
Afterwards system is cooled to the dilute sulfuric acid of 20～25 DEG C of addition concentration 26-27%, further cools to 0 DEG C, slowly Deca is joined in advance
The sodium nitrite solution of good concentration 38%, after 1-1.5 hour drips off, stirring 0.5-1 hour makes reaction complete；In another gas
Below C4 lower alcohol is added, ice salt bath is placed in outside makes temperature in bottle be maintained at -10-0 DEG C, installs vent gas treatment in receiving flask
Device, UNICOM's reaction bulb and gas receiving flask, the seal of inspection system, start blender, at 20-40 DEG C after being ready to complete
The strong base solution of slowly Deca concentration 50% in reaction bulb, until Azimethylene. absorbs saturation, its content 18.5- in receiving flask
25.5%, close intercommunicating device, obtain Azimethylene. alcohol saturated solution；
Weight proportion between reactant is：40% methylamine：Concentrated hydrochloric acid：Carbamide：Sodium carbonate：Sulphuric acid：Sodium nitrite：Highly basic：Water=1：
1.00-1.25：0.95-1.05: 0.20-0.30：0.80-0.85：0.9-1.0:1.15-1.25:5.8-6.0；Reactant and weight
Proportioning between formylmerphalan alkane lyosoption is, 40% methylamine solution：Organic solvent=1g：4～8ml.
3. the method that Ketohexamethylene one-step method prepares cycloheptanone according to claim 1, is characterized in that preparing cycloheptanone crude product
Method is to add Ketohexamethylene and aqueous acid, pH=5.5～6.5 in Deca bottle, be positioned on above-mentioned receiving flask；Work as acceptance
Temperature slowly Deca Ketohexamethylene and aqueous acid when 10～50 DEG C in bottle, controls time for adding 2.5～3 hours, drips off follow-up
Continuous insulation reaction 1.5～2 hours, has reacted rear recovered under reduced pressure organic solvent, has then carried out steam distillation, obtain cycloheptanone thick
Product, weight yield 90～95%, G/C content 65～70%；Reaction residue and vinasse all can be applied mechanically.
4. the method that Ketohexamethylene one-step method prepares cycloheptanone according to claim 1, is characterized in that, cycloheptanone crude product rectification obtains
Cycloheptanone, under 5～10mmHg post vacuum, collects 102～105 DEG C of fractions, obtains cycloheptanone；Content 99.0～99.5%, rectification
Weight yield 50～55%；Distillation residual liquid can be applied mechanically；In terms of the Equilibrium yield applied mechanically, synthesize weight total recovery 75～80%.
5. the method preparing cycloheptanone according to claim 2 Ketohexamethylene one-step method, is characterized in that, below C4 low-carbon alcohols include first
Alcohol, ethanol, isopropanol；Acid catalyst include the acetic acid of the hydrochloric acid of mineral acid, sulphuric acid, phosphoric acid, or organic acid, p-methyl benzenesulfonic acid,
Oxalic acid；The inorganic strong alkali solution of Deca includes sodium hydroxide solution, potassium hydroxide；Methylamine salt and methylamine urea reaction temperature are -10
～0 DEG C, Azimethylene. reacts temperature for 20-40 DEG C；Described aqueous acid includes hydrochloric acid or the sulphuric acid of mineral acid, or organic
The acetic acid of acid or p-methyl benzenesulfonic acid, sour water concentration 1%；10～50 DEG C of the reaction temperature of addition ring expansion, reactant Ketohexamethylene with
The proportioning of Azimethylene. alcoholic solution is 1g：2.5～3.5ml.
6. the method that Ketohexamethylene one-step method according to claim 2 or 5 prepares cycloheptanone, is characterized in that, low-carbon alcohols ethanol；
Acid catalyst acetic acid；Inorganic strong alkali sodium hydroxide solution；The Azimethylene. temperature that reacts is 25～30 DEG C；Between reactant
Weight proportion be：40% methylamine：Concentrated hydrochloric acid：Carbamide：Sodium carbonate：Concentrated sulphuric acid：Sodium nitrite：Highly basic：Water=1:1.15 :1:
0.26: 0.825: 0.95:1.2:5.9；The reaction temperature of addition ring expansion is 30～35 DEG C；Ketohexamethylene and Azimethylene. alcohol
The proportioning of solution is 1g：3ml.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253240A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method and system for synthesizing adipic acid by microreactor |
-
2016
- 2016-09-05 CN CN201610801017.6A patent/CN106380385A/en active Pending
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| Title |
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| 李良助等: "《有机合成原理和技术》", 31 May 1992, 高等教育出版社 * |
| 道客巴巴: "重氮甲烷的性质及制备", 《道客巴巴》 * |
| 邢其毅等: "《基础有机化学（第二版）》", 30 November 1993, 高等教育出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111253240A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method and system for synthesizing adipic acid by microreactor |
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