CN1616393A - Method for preparing anchoic acid by microwave cracking ozonization reaction product - Google Patents
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Abstract
The anchoic acid process includes the contact reaction between the mixture of oleic acid and solvent and ozone under controlled temperature inside a ozonizing reactor, setting the ozonized product in a microwave reactor and introducing oxygen to produce microwave oxidation cracking reaction of the ozonized product, and treating the product through distillation, extraction, crystallization, suction filtering and drying to obtain anchoic acid and side product nonoic acid. The said process has no need of catalyst, short cracking reaction time, high anchoic acid yield up to 80 %, reuse of solvent, reaction converting ozone into oxygen and no environmental pollution, and is suitable for large scale production.
Description
Technical field
The present invention relates to a kind of method for preparing nonane diacid with the microwave cracking ozonization reaction product.
Background technology
Nonane diacid (Azelaic acid) be lepargylic acid again, is that a kind of white is to little yellow monoclinic prisms, needle-like crystal or powder.Molecular formula C
9H
16O
4, molecular weight 188.22, proportion 1.0291 (4 ℃), 1.225 (25 ℃), 106.5 ℃ of fusing points, 286.5 ℃ of boiling points (13.33kPa), specific refractory power 1.4303 (111 ℃), the carbochain of moderate-length is added two carboxyls, gives nonane diacid wide purposes, is important organic synthesis intermediate.
Nonane diacid can be used to products such as synthetic dioctyl azelate (DOZ) softening agent, synthetic perfume, lubricating oil and polymeric amide.Dioctyl azelate, nonane diacid didecyl ester, the two tridecane esters of nonane diacid all are good lubricants.Nonane diacid also is used for the production of nylon 69 and nylon 9.Nonane diacid makes amino-nonanoic acid through amination, hydrogenation, and the amino-nonanoic acid direct condensation can be produced nylon 9.Nonane diacid can improve the snappiness of unsaturated polyester, can be used as the properties-correcting agent of terephthalic acid-polyglycol ester.In addition, other of nonane diacid used and also comprised dielectric liquid, emulsion splitter, mothproofing agent, urethane methyl ester foam, hydraulic efficiency oil, high molten coating, tackiness agent and water soluble resin etc.
The discovered in recent years nonane diacid has superior electrical property, is used for manufacturing (fine chemistry industry, 1994,11 (1): 56-58) of electrical condenser.Nonane diacid also is used to dermopathic control.The too much disease of acne, rosacea, chloasma and cutaneous pigmentation (Chinese Hospitals pharmaceutical journal, 2002,22 (4): 242-243) have been used for the treatment of clinically
At present, the production method of nonane diacid mainly is the oxidation style of unsaturated fatty acidss such as oleic acid, and used oxygenant has potassium permanganate, nitric acid, chromic acid, hydrogen peroxide, hypochlorite, ozone etc.
Liang Fangzhen uses phase-transfer catalyst (TBAB), and potassium permanganate is oxygenant, prepares nonane diacid from the Fructus Zanthoxyli oil soap stock.Yang Yang etc. compare and discuss (Jiangsu Petrochemical Engineering College journal, 2001,13 (1): 5-7) to the effect of several ammonium salt class phase-transfer catalysts.High farm member has inquired into reaction conditions (Hunan chemical industry, 2000,30 (3): 36-37) that utilize potassium permanganate to prepare nonane diacid.Sabarino Giampiero is with HWO
4Be catalyzer, with H
2O
2The oleic acid of oxidation purity 80%, the reaction intermediate blend is forced into about 70 normal atmosphere in the presence of cobaltous acetate, and reaction 4.5h obtains people such as nonane diacid and n-nonanoic acid .Pultinas EdmundP and utilizes 70% H under 66 ℃
2O
2Make acetate be converted into Peracetic Acid, again with CH
3COON (CH
3)
2Be solvent, at (CH
3COO)
2Co exists down, oxidation 9, and the 10-dihydroxystearic acid obtains reaction mixture, obtains nonane diacid and n-nonanoic acid through dioxygen oxidation again.It is the nitric acid oxidation process of raw material that National Oil Products Co. has developed with the Witconol 2301.Human oxyethyl group lauryl alcohols such as Zaidman B are mixed with the O/W emulsion to oleic acid, with RuCl
3Be catalyzer, use chlorine bleach liquor's oxidation, obtain nonane diacid and n-nonanoic acid (Speciality Petrochemicals, 1998, (6): 40-43) through separation.
English Patent GB 813,842 adopts the method for nitric acid oxidation to prepare nonane diacid.
(Catalysis Today.79-80 (2003): 59-65) method of Cai Yonging is wolframic acid to be made the product that the catalyzer hydrogen peroxide oxidation produced pour autoclave into to people such as E.Santacesaria, and adding is dissolved with the 300ml distilled water of 1.2 grams, four water cobaltous acetates, and be heated to 70 ℃, feed 15 atmospheric oxygen and 30 atmospheric nitrogen and impel 9, the oxicracking of 10-dihydroxystearic acid.
The method that people (Journal of molecular catalysis:chemical150 (1999) 105-111) such as M.chael A adopt: in the 25ml there-necked flask,, add oleic acid 2.0 mmoles at the bottom aerating oxygen.0.03 the mmole wolframic acid, the 5ml trimethyl carbinol, 11 moles of hydrogen peroxide drip, and are heated to reflux 2 hours, and temperature is transferred to 75 ℃ again, add 8 milligrams of NHPI, 8 milligrams of acetylacetone cobalts, aerating oxygen (0.5ml/min), stir separated in 3-5 hour product.
A kind of method that the patent WO of World Intellectual Property Organization 9410122 adopts is: with wolframic acid, molybdic acid or its basic metal or alkaline earth salt as catalyzer, the 50-70% hydrogen peroxide oxidation obtain 9,10-dihydroxyl intermediate product adds autoclave, the aqueous solution that adds cobaltous acetate, be pressurized to 70 normal atmosphere, reaction is 4.5 hours under 66 ℃ temperature, and the refrigerated separation purifying gets nonane diacid and n-nonanoic acid.
Danish Patent DE 2045558 is with 9, the 10-dihydroxystearic acid is a raw material, and vinylbenzene is solvent, cobaltous acetate (or manganous acetate, iron, lead, nickel) be catalyzer, with Peracetic Acid oxicracking 9, the 10-dihydroxystearic acid, product is handled with benzene, obtains nonane diacid with water crystallization, and the benzole soln underpressure distillation obtains n-nonanoic acid.
Danish Patent DE 2144015 is with 9, and the 10-dihydroxystearic acid is a raw material, and Glacial acetic acid is a solvent, cobaltous acetate is catalyzer and adds a certain amount of Peracetic Acid, is heated to 100 ℃, first blowing air 3 hours, add Peracetic Acid again, and aerating oxygen 1 hour, obtain nonane diacid and n-nonanoic acid.
The WO of World Intellectual Property Organization 9312064 adopts 45% hydrogen peroxide oxidation, and wolframic acid is made catalyzer and added phase-transfer catalyst Arqual 2HT (or tricaprylmethylammonium),, 100-104 ℃ of reaction 6 hours, reaction was finished, and separation and purification gets nonane diacid and n-nonanoic acid.
It is catalyzer that U.S. Pat 809451 adopts cobalt naphthenate, and oxidation oleic acid prepares nonane diacid.
The method that people such as S.E.Turnwald (Journal of materials science letters17 (1998) 1305-1307) adopt is under a kind of new catalyst P CWP effect, prepares nonane diacid with hydrogen peroxide oxidation oleic acid.
It is oxygenant that European patent EP 122804 adopts 40% hydrogen peroxide, at [(C
8H
17)
3NCH
3]
3PW
4O
22Under the catalysis, and add 1, the 2-ethylene dichloride 80 ℃ of reactions 5 hours, gets the nonane diacid of productive rate 83% and 66% n-nonanoic acid as solvent.
Lanzhou Inst. of Chemical Physics, Chinese Academy of Sciences's (Chinese patent, application number: 02150179.3 publication number: CN 1415593A) adopt the mesopore molecular sieve W-MCM-41 that supports tungsten to make the Preparation of Catalyst nonane diacid, with oleic acid, mesopore molecular sieve W-MCM-41, the superoxol and the trimethyl carbinol mix, under the stirring and refluxing state logical oxygen reaction 1-3 days, from reaction solution, extract the product nonane diacid.
Employing ozone oxidation legal systems such as Qian Weiqun are equipped with nonane diacid, and productive rate is about 45% (fine chemistry industry, 1994,11 (1): 56-58) under laboratory scale.
The king is big, and strange the grade with Oleum Gossypii semen soap stock lipid acid is raw material, adopts the ozone oxidation method to make nonane diacid (research and development of natural products, 1997,9 (2): 39-42).
The Emery Industries Inc (U.S. Pat 2,813,113) of the U.S. at first produces n-nonanoic acid and nonane diacid as oxygenant from oleic acid with ozone on industrial production.Their production method is roughly as follows: the mixture that at first makes oleic acid and n-nonanoic acid generates oleic ozonization product by the ozonization device; Then the ozonization product is heated to 80 ℃-100 ℃ reactions 1.5-3.0 hour, logical oxygen carries out oxicracking.Distill above oxidation mixture and obtain n-nonanoic acid, remaining resistates is used the water hot extraction, obtains product of nonane diacid with evaporation or crystalline method again.
On the research basis of U.S. Emery, the descendant is in choice of Solvent, selection of catalysts, the contact method of material, reactor design, aspects such as the separation and purification of product carried out improving (referring to patent US 2813113, GB757455, GB841653, GB810571, US2450858, US 3979450, US6362368B1, US 6512131, and US 20030032825), and the report of relevant mechanism research is arranged in recent years, and (referring to document: U.S. oil chemistry man can will JAOCS, 1995,72 (6), 745-740, the meeting will JAOCS of U.S. oil chemistry man, 1992,69 (2), 159-165), yet these improve the technology of still continuing to use traditional ozonization: carry out ozonization in 25-46 ℃ of temperature range, then temperature is raised to 75-120 ℃ of logical oxygen and carries out cracking.Also relevant for the report of ozonization product catalytic oxidative cracking, mainly use the catalyzer (referring to patent US 5399749, US 5420316) of molecular sieve and molecular sieve supported manganese salt in recent years
The selectivity of nitric acid oxidation method reaction is not high, and serious to equipment corrosion.With potassium permanganate is the thickened oil acid system of oxygenant, and yield is low, consumes a large amount of sulfuric acid and potassium permanganate again, cost height not only, and also seriously polluted.Although can improve the technology of potassium permanganate process with emulsion process, the consumption of potassium permanganate is still very big, and aftertreatment is very numerous and diverse, and is inadvisable economically., cost an arm and a leg as oxygenant with chromic acid, and make the oxidation products degradation easily, produce the low carbon chain diprotic acid, resulting product purity is not high.This shows in many prior arts, some method contaminate environment, the method steps that has is more numerous and diverse, and the method that has need support noble metal catalyst, and needs long-time logical oxygen, length consuming time, cost height.Some method needs high pressure, the implementation condition harshness, and the cost costliness is difficult to carry out large-scale production.
Microwave is the frequency hertzian wave in 300MHz～300GHz (being that wavelength is at 100cm to 1mm) scope greatly.It is positioned between the ir radiation (light wave) and radiowave of electromagnetic spectrum.Why microwave can be used in chemical field, be because when microwave oven magnetic control pass pipe gives off the microwave of very high frequency, microwave energy field is with the speed of per second 24.5 hundred million times conversion positive-negative polarity constantly, great change has taken place in molecular motion, molecular arrangement is got up and high-speed motion, run foul of each other, rub, push, make kinetic energy-micro-wave energy be converted into heat energy.Because this kind energy is from sample interior, itself does not need the medium that conduct heat, and by convection current, sample temperature just can very fast rising, thus can be comprehensively, fast, heated sample equably.That is to say that microwave heating is the endogenous thermal source, microwave heating has selectivity.
Because the type of heating of microwave uniqueness can greatly improve chemical reaction velocity in reaction, reduced the activation energy of reaction, changed reaction kinetics.Utilize the type of heating and the microwave of microwave uniqueness that there be " non-thermal effect " in chemical reaction, can add the carrying out of fast response.Demonstrate its be swift in response, fully, productive rate height, good selective.
Compared with the prior art the present invention has tangible technical progress with different.The present invention with the mixture controlled temperature of oleic acid and solvent in the ozonization device with ozone contact reaction, product is carried out the microwave oxidative cracking reaction.This method adopts microwave faster more than 2 times than conventional cracked speed; And compare with existing oleic acid ozonize technology, need not catalyzer in the cracking process of the present invention, and the time of scission reaction shorten greatly, shortened to 0.5-1 hour by original 1.5-3.5 hour.Technology cleaning of the present invention, environmental friendliness, free from environmental pollution, need not catalyzer, implementation condition is simple, is convenient to carry out large-scale production.
Summary of the invention
The object of the invention is to provide a kind of method for preparing nonane diacid with the microwave cracking ozonization reaction product, this method with the mixture controlled temperature of oleic acid and solvent at 25-60 ℃ of ozone contact reaction in the ozonization device, generate oleic ozonization product, then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, after reaction finishes, product obtains nonane diacid through routine distillation, extraction, crystallization, suction filtration, drying, gets the by product n-nonanoic acid simultaneously.This method adopts microwave reaction to carry out the cracking of ozonization product; need not catalyzer in the cracking process, the time of scission reaction shortens greatly, promptly adopts microwave faster more than 2 times than conventional cracked speed; the productive rate of product of nonane diacid is higher; reach as high as 80%, solvent can recycle and reuse, and is converted into oxygen behind the ozone reaction; compared with prior art be a kind of free from environmental pollution; technology cleaning, environmental friendliness is convenient to the method for large-scale production.
A kind of method for preparing nonane diacid with the microwave cracking ozonization reaction product of the present invention, this method with the mixture controlled temperature of oleic acid and solvent 25-60 ℃ in the ozonization device ozone contact reaction 1.5-3.5 hour, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, reaction times 0.5-1.0 hour; After reaction finished, product obtained nonane diacid through distillation, extraction, crystallization, suction filtration, drying, got the by product n-nonanoic acid simultaneously; Wherein the mol ratio of oleic acid and solvent is: 0.15: 0.75-15.
Solvent is industrial Glacial acetic acid or acetum or water or n-nonanoic acid or formic acid.
The mass percentage concentration of ozone is 2%-7%.
Characteristics of the present invention are to adopt the microwave cracking ozonization reaction product to prepare nonane diacid, and oxygenant is an ozone; Solvent can recycle and reuse.The present invention compared with the prior art; have following characteristics: (1) adopts microwave reaction to carry out the cracking of ozonization product; the time that need not catalyzer (2) scission reaction in the cracking process shortens greatly; shortened to 0.5-1 hour by original 1.5-3.5 hour; promptly adopt microwave than conventional cracked speed fast more than 2 times the productive rate of (3) product of nonane diacid higher; reaching as high as 80% (in the whole nonane diacid weight that transform of ideal) (4) solvent can recycle and reuse (5) and need not to be converted into oxygen behind catalyzer (6) ozone reaction; noresidue; so and potassium permanganate; nitric acid; hypochlorite is that the method for oxygenant is compared; be a kind of free from environmental pollution; the technology cleaning; environmental friendliness is convenient to the method for large-scale production.
Embodiment
Embodiment 1
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of industrial Glacial acetic acid 215ml (3.5mol) 42 ℃ in the ozonization device with ozone (controlling concn w (ozone)=7%) contact reacts 1 hour, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 0.5 hour reaction times; After reaction finished, product obtained product nonane diacid 16.7g through routine distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 80%.
Embodiment 2
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of industrial Glacial acetic acid 860ml (15mol) 60 ℃ in the ozonization device with ozone (control ozone concn w (ozone)=5%) contact reacts 1.5 hours, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 1.0 hours reaction times; After reaction finished, product obtained product nonane diacid 15.5g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 74%.
Embodiment 3
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of industrial Glacial acetic acid 43ml (0.75mol) 25 ℃ in the ozonization device with ozone (control ozone concn w (ozone)=2%) contact reacts 3.5 hours, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 0.8 hour reaction times; After reaction finished, product obtained product nonane diacid 16.9g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 81%.
Embodiment 4
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of aqueous acetic acid 200ml 40 ℃ in the ozonization device with ozone (control ozone concn w (ozone)=5%) contact reacts 2.5 hours, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 0.5 hour reaction times; After reaction finished, product obtained product nonane diacid 14.2g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 68%.
Embodiment 5
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of n-nonanoic acid 400ml (2.9mol) 35 ℃ in the ozonization device with ozone (controlling concn w (ozone)=7%) contact reacts 1.5 hours, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 1.0 hours reaction times; After reaction finished, product obtained product nonane diacid 15.9g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 76%.
Embodiment 6
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with water 200ml (11.1mol) emulsification after the mixture controlled temperature 45 ℃ in the ozonization device with ozone (controlling concn w (ozone)=7%) contact reacts 2.5 hours, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, 0.5 hour reaction times; After reaction finished, product obtained product nonane diacid 13.6g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 65%.
Embodiment 7
With chemical pure oleic acid 42.4g (0.15mol, oleic acid quality percentage composition is 74.1%) with the mixture controlled temperature of formic acid 200ml (5.3mol) 30 ℃ in the ozonization device with ozone (controlling concn w (ozone)=7%) contact reacts 1 hour, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, reaction times 0.5-1.0 hour; After reaction finished, product obtained product nonane diacid 14.2g through distillation, extraction, crystallization, suction filtration, drying, and productive rate fusing point 106-108 ℃, obtains the by product n-nonanoic acid simultaneously in oleic acid 68%.
Claims (3)
1, a kind of method for preparing nonane diacid with the microwave cracking ozonization reaction product, it is characterized in that, this method with the mixture controlled temperature of oleic acid and solvent 25-60 ℃ in the ozonization device ozone contact reaction 1.5-3.5 hour, generate oleic ozonization product; Then the ozonization product is put into microwave reactor, under the logical oxygen condition, carry out the microwave oxidative cracking reaction of ozonization product, reaction times 0.5-1.0 hour; After reaction finished, product obtained nonane diacid through distillation, extraction, crystallization, suction filtration, drying, got the by product n-nonanoic acid simultaneously; Wherein the mol ratio of oleic acid and solvent is: 0.15: 0.75-15.
2, according to claim 1ly a kind ofly prepare the method for nonane diacid, it is characterized in that solvent is industrial Glacial acetic acid or aqueous acetic acid or water or n-nonanoic acid or formic acid with the microwave cracking ozonization reaction product.
3, according to claim 1ly a kind ofly prepare the method for nonane diacid with microwave cracking ozonization product thing, the mass percentage concentration that it is characterized in that ozone is 2%-7%.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103467273A (en) * | 2013-09-24 | 2013-12-25 | 辽宁石油化工大学 | Method for preparing azelaic acid from rare earth Ce-loaded mesoporous molecular sieve catalyst |
| CN104447279A (en) * | 2014-12-05 | 2015-03-25 | 辽宁石油化工大学 | Method for synthesizing anchoic acid through combined oxidation of hydrogen peroxide and potassium permanganate |
| CN104797552A (en) * | 2012-11-09 | 2015-07-22 | 阿克马法国公司 | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
-
2004
- 2004-09-15 CN CN 200410079229 patent/CN1239459C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104797552A (en) * | 2012-11-09 | 2015-07-22 | 阿克马法国公司 | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
| CN103467273A (en) * | 2013-09-24 | 2013-12-25 | 辽宁石油化工大学 | Method for preparing azelaic acid from rare earth Ce-loaded mesoporous molecular sieve catalyst |
| CN104447279A (en) * | 2014-12-05 | 2015-03-25 | 辽宁石油化工大学 | Method for synthesizing anchoic acid through combined oxidation of hydrogen peroxide and potassium permanganate |
| CN104447279B (en) * | 2014-12-05 | 2016-05-18 | 辽宁石油化工大学 | The method of the synthetic azelaic acid of a kind of hydrogen peroxide and potassium permanganate co-oxidation |
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