What acrylic acid reacts. Non-precious acids

Acrylic (props, ethylene carbonic) acid CH2 \u003d CH-coxy - colorless liquid with a sharp odor; t. pl. 285-286.5 K, t. Kip. 413.9-414.6 K, D420 \u003d 1,0511. Dissolves in water, alcohol, SNS13, benzene. When stored is polymerized.

Acrylic acid and its salts are used for the manufacture of water-soluble polymers and copolymers, which are used as an appertain bonding dispersants. Approximately half of the acrylic-acrylic esters - acrylate is spent on the production of paints for internal and outer coatings. Coatings are distinguished by abrasion resistance, quickly dry and do not yellow. Acrylate based lacquers are used for coloring household appliances and car bodies by spraying. A significant part of the acrylate produced is used in textile industry. IN paper industry Polyacrylates are used for paper challenges and cardboard, as well as to obtain coatings. Polymers of ethyl-, butyl and 2-ethylhexyl acrylate often in combination with styrene, vinyl acetate or vinyl ethers are component parts Many adhesives. Copolymers of ethyl acrylate and ethylene are valuable elastomers.

The following methods for producing acrylic acid are being implemented in industry:

• - hydrolysis of ethylene cyanhydrin;
• - hydrolysis of acrylonitrile;
• - hydrocarboxylation of acetylene;
• - oxidation of propylene in the vapor phase with intermediate formation of acrolein;
• 1. Hydrolysis of ethylene cyangidrin

One of the variants of obtaining acrylic acid is based on the interaction of ethylene oxide with cyanhydrin to form ethylene cyanhydrin:

CH2 - CH2 + HCN HOCH2 CH2CN.

The subsequent hydrolysis of ethylene cyanhydrin to acrylic acid is carried out in a sulfuric acid medium in accordance with the reactions:

HOCH2CH2CN + 2H2O HOCH2CH2COOH + NH4HSO4

CH2 \u003d CHCOOH + H2O.

The overall yield of acrylic acid does not exceed 60-70%.

This method is developed by UNION CARBAID. However, he did not receive industrial development: the last operating plant for this method was stopped in 1971.

2. Hydrolysis acrylonitrile

Nitrile hydrolysis is one of the most common synthesis methods. carboxylic acids. The process is catalyzed by acids or alkalis and flows through the intermediate stage of formation of amides:

Conh2 + H2O RCOOH + NH3

The reaction is carried out in aquatic environment With a heating agent 323-353 K. The ratio of the velocities of both reactions depends on the structure of nitriles, the nature of the catalyst used and the conditions for conducting hydrolysis. If K1 \u003e\u003e K2, then, despite the excess of water, the reaction can be stopped at the stage of amide formation. When hydrolysis with sulfuric acid, the ratio k1: k2 depends on the concentration of the acid. For example, in the hydrolysis of propionitrile with sulfuric acid, only propionic acid is obtained (K1: K2\u003e 100). With an increase in the acid concentration of the speed of both reactions become commensurate. When processing many nitriles, 50% and more diluted with sulfuric acid, as a rule, carboxylic acids are obtained. In the interaction of nitriles with more concentrated acids, the reaction is often stopped at the formation stage of amide.

Thus, the use of highly concentrated mineral acids contributes to the preparation of amide, and carboxylic acids are formed in the field of low concentrations of acids (K2 \u003e\u003e k1).

When an acrylic acid is obtained by sulfuric acid hydrolysis, the process is carried out in two stages: first synthesize acrylamide sulfate, and then acrylamide sulfate is washed with the separation of acrylic acid.

After heat treatment, the mixture obtained by hydrolysis of acrylamide sulfate with water, acrylic acid is distilled off under reduced pressure. However, due to the polymerization of acid in the vapor phase, its significant amount is lost. The selection of acid from the mixture after hydrolysis of acrylamide sulfate can be carried out by distillation along with an organic solvent added to the hydrolyzed reaction mixture. In this case, the mixture of vapors enters the condenser in which an additional amount of water is supplied. The resulting mixture is separated on the layer organic solvent and a layer of aqueous acid solution, the concentration of which is regulated by the amount of added water. As solvents, O-, M-, P-Creensoles, Naphtol and Croose oil fractions can be used.

Adverse reactions in hydrolysis of acrylonitrile. In the sulfuric acid hydrolysis of acrylonitrile, along with the main reaction of the formation of acrylamide sulfate, cork reactions flow, leading to the formation of propionic acid amide sulfate, acrylic acid, etc. esterification is carried out in a reactor with a stirrer made of anticorrosive material - glass, ceramics, enamelled materials, polytetrafluoroethylene . At the esterification stage, alkyl and alkoxyalkylpropionates, dialkyl ether, ammonium sulfate are formed as by-products. At the esterification stage of acrylamide sulfate in an acidic medium, an alcohol dehydration is possible to form a simple ether, which, when contacting air, is easily converted into peroxide compounds, which are active polymerization initiators.

Acrylic acid polymerization inhibitors. When cleaning acrylic acid with rectification, it is polymerized, and this occurs significantly faster in the gas phase than in liquid, since the polymerization inhibitors usually used in the synthesis - hydroquinone, methylhydroquinone, phenothiazine, methylene blue and others - in the gas phase are contained in smaller quantity than It is necessary to stabilize the acid.

The resulting polymer acrylic acid, not soluble in acid and other solvents, quickly fills the distillation column, and the continuous process becomes impossible.

To prevent polymerization of acid at distillation, various polymerization inhibitors, such as hydroquinone, phenol or its derivatives and oxygen, diphenylamin or its derivatives, are added.

As an acrylic acid polymerization inhibitor, ammonium chloride can also be used, 1% solution of which is supplied to top distillation column.

In order to avoid the formation of a polymer on the surface of the apparatuses from steel, with distillation of acrylic acid, they are coated with polytetrafluoroethylene, which is applied to the surface of the evaporator in the form of a film.

3. Hydrokarboxylation acetylene

Acrylic acid or her ethers can be obtained by interaction of acetylene with nickel tetracronyl (carbon oxide source) in the presence of water or other protons donor (alcohols, mercaptans, amines, organic acids):

4CN CH + 4N2O + Ni (CO) 4 + 2NC1 4CN2 \u003d CH-coo + NIS12 + H2

If instead of water use single-napol, acrylic acid ester is formed:

4C2N2 + Ni (CO) 4 + 4Ron + 2NC1 4CN2 \u003d CH-COP + NIS12 + H2.

The reaction is carried out at a temperature of 313 K, atmospheric pressure and acetylene ratio: CO equal to 1: 1, in the presence of nickel tetracarbonyl catalyst.

The disadvantage of this method is the use of explosive acetylene.

4. Parophasic oxidation of propylene

The process of steaming oxidation of propylene is the main industrial method for producing acrylic acid. The preparation of acrylic acid by oxidation of propylene in the gas phase through the intermediate formation of acrolein is realized in two stages:

CH2 \u003d Chch3 + O2 CH2 \u003d ChCho + H2O DH298 \u003d -340 kJ / mol

CH2 \u003d CHCHO + 0.5O2 CH2 \u003d CHCOOH DH298 \u003d -250 KJ / MOL

In the first stage, the oxidation of propylene is carried out, and on the second - oxidation of acrolein.

Oxidation of propylene. The oxidation of propylene proceeds along a radically chain mechanism and includes the following steps:

CH2 \u003d CH - CH3 + O · CH2 \u003d CH - CH2 · + H2O, (circuit birth)

CH2 \u003d CH - CH2 · + O · CH2 \u003d CH - CH · + OH, (chain growth)

CH2 \u003d CH - CH · + O · CH2 \u003d CH - CHO, (chain opening)

CH2 \u003d CH - CHO + OH · CH2 \u003d CH - CO * + H2O,

CH2 \u003d CH - CO · + OH · CH2 \u003d CH - COOH.

In the process of oxidation, by-products are formed, which are a consequence of the reactions of partial or complete oxidation of propylene (acetaldehyde, acetic acid, CO, CO2) and polymerization reactions. An increase in the output of acrolein and acrylic acid and, accordingly, the suppression of the adverse reaction is favored by low temperatures: 673-773 K. The decrease in the reaction temperature is possible when using high-selective catalysts.

The oxidation of propylene is carried out at 573-623, a pressure of 0.1-0.3 MPa and the addition of water vapor on catalysts containing bismuth oxides, cobalt, nickel, iron, tin, etc. Moldable water ratio: propylene is maintained at 4-5 And the molar ratio of oxygen: propylene - ~ 2. Couples and nitrogen reduce not only the possibility of overheating, but also the risk of creating explosive situations. These gases also contribute to the increase in catalyst activity, facilitating the desorption of the reaction products, and an increase in the duration of stable operation to 24 months. The degree of propylene conversion in one pass is 90-95% and the yield of acrolein and acrylic acid - 80-90%.

Oxidation of acrolein. Oxidation of acrolein is carried out in a heterogeneous-catalytic embodiment on catalysts obtained on the basis of mixed molybdenum oxides and vanadium modified by tungsten oxides, chromium, copper, tellurium, arsenic, etc.

The activity of various oxides in the process of catalytic oxidation of acrolein decreases in the next row:

Moo3\u003e V2O5\u003e WO3\u003e SEO2\u003e TEO2\u003e NB2O5\u003e TA2O5\u003e CRO3.

For catalytic oxidation, only electronene catalysts are used above 2.93. Inactive oxides of CO2O3 and PBO2 acquire activity as a result of the introduction of H3ro4. The activating effects have strongly negative additives: H3Pro4, H2SO4, MO3, H3SO3, Teo2. The most effective catalyst for oxidation acrolein is Mo3.

The process is carried out at a temperature of 523-553 K and a pressure of 0.1-0.2 MPa in the presence of water vapor with a molar ratio of water: acrolein, equal to 2: 1. The degree of conversion for one pass is 95-97%, the yield of acrylic acid is more 90% per acherolein.

The technology of obtaining acrylic acid by oxidation of propylene was first developed by the firm "Distillers", and later concerns BASF, SOCHIO, Toyo Soda, Union Carbaid, "Jipan Catalytic".

In industry, acrylic acid is obtained by a two-stage method of propylene oxidation through acrolein without separation and purification of the acrolein-generated at the first stage.

acrylic Acrylic Acrylic Acrylic Acid Formula
(Propented Acid, Etencarboxylic Acid) CH2 \u003d CH-coton is the simplest representative of monosocondary non-perfection carboxylic acids.

• 1 Physical Properties
• 2 Synthesis
• 3 Chemical properties
• 4 Application
• 5 Safety
• 6 Notes
• 7 cm also
• 8 literature

Physical properties

Acrylic acid It is a colorless liquid with a sharp smell, soluble in water and organic solvents

Synthesis

For acrylic acid synthesis, steam oxidation of air oxygen on bismuth, cobalt or molybdenum catalysts is used:

CH2 \u003d CH-CH3 + O2 → CH2 \u003d CH-COOH

Previously, the reaction of the interaction of acetylene, carbon monoxide (II) and water was used:

HC≡CH + CO + H2O → CH2 \u003d CH-COOH

or ketten with formaldehyde:

CH2 \u003d C \u003d O + HCHO → CH2 \u003d CH-COOH

ROHM AND HAAS The technology of acrylic acid synthesis is developed from propane.

Chemical properties

It has chemical properties of carboxylic acids: interacts with active metals, bases, with salts of weaker acids with salts, with alcohols with the formation of esters.

Acrylic acid forms salts, chlorogenhydride, anhydrides, esters, amides, etc. It enters the reaction of the attachment characteristic of ethylene hydrocarbons. Under the action of sodium amalgam in aqueous solution and hydrogenation in the liquid phase in the presence of Ni, Pt, Pd to propionic acid. The addition of proton acids, water and NH3 occurs against the Markovnikov rule with the formation of substituted derivatives. As dioinophil acrylic acid participates in a diene synthesis. Condensing with alilds of arhydiazonium (reaction of Meersvein):

N-CLC6H4N2CL + CH2 \u003d CH-COOH → N-CLC6H5-CH \u003d CH-COOH + N2

With uv irradiation or in acidic aqueous solutions (pH \u003d 1), and also in the presence of polymerization initiators forms polyacrylic acid (N).

Application

To prevent polymerization during storage, an inhibitor is added - hydroquinone. Before use, explosive polymerization is possible with extreme caution.

Acrylic acid and its derivatives are used in the production of acrylic emulsions for paint and varnishes, impregnation of tissues and skin, as raw materials for polyacrylonitrile fibers and acrylate rubbers, construction mixes And adhesives. A significant part of acrylic acid is also used in the production of superabsorbents. The production of polymers is widely used by acrylic and methacrylic acid esters, mainly methyl esters: methyl acrylate and methyl methacrylate.

Safety

Acrylic acid is strongly annoying skin cover. Irritate the mucous membrane of the eyes (the threshold of irritating 0.04 mg / l). If you get into the eyes, it causes strong burn cornea burns and can cause irreversible damage. Inhalation of vapors can cause irritation respiratory tract, Headache, at high concentrations or exposure - edema lungs. Although the presence of smell does not mean any threat to health, air monitoring is necessary. The maximum permissible concentration is 5 mg / m³.

Notes

• Kirk-Othmer Encyclopedia, 3 ED., V. I, N.Y.-, 1978, p. 330-54. A.V. Gestka.
• Rabinovich V. A., Khavin Z. Ya. "Short Chemical Directory" L.: Chemistry, 1977 p. 121

see also

• Acrylate
• Acrolein
• Acrylonitrile
• Metacryl Acid

Literature

• Chemical encyclopedia / edge.: Knunyantz I.L. And others. - M.: Soviet Encyclopedia, 1988. - T. 1 (ABL-DAR). - 623 p.

acrylic Acrylic Acrylic Acrylic Acid Formula

Acrylic acid information about

The name acrylic acid is synonyms propacted acid; Registration number CAS 79-10-7 Molecular formula C 3 H 4 O 2 Molecular weight 72.06 INCHI INCHI \u003d 1S / C3H4O2 / C1-2-3 (4) 5 / H2H, 1H2, (H, 4,5) Inchikey NixowildQLNWCW-UHFFFAOYSA N Smiles C \u003d CC (\u003d O) o Einecs 201-177-9 HS Code 29161110

Chemical and physical properties

Density 1.051 Boiling point 139 ° C Melting point 13 ° C Flash temperature 48 ° C Storage temperature 15-25 ° C Refractive index 1.4192-1.4212 Solubility is mixed with water. Stability is unstable - may contain P-methoxyphenol as an inhibitor. Inclined to hazardous polymerization. Fuel. Incompatible S. strong oxidizing agents, strong bases, amines. Contact with oxidizing agents can lead to fire. Sensitivity to light and air. Gigroscopic. Appearance Colorless liquid.

Risks, Security and Terms of Use

Safety instructions S26; S36 / 37/39; S45; S61 R10 risk guidelines; R20 / 21/2 22; R35; R50 hazard class 8 danger symbols

Classification of chemical reagents

Clean ("h.") Acrylic acid C. The content of the main component is 98% and above (without impurities). Color stripes on packaging - green. Clean for analysis ("Ch.D.A.", "Chda") Acrylic Acryl Chda. The main component content is higher or significantly higher than 98%. Impurities do not exceed the permissible limit for accurate analytical studies. Color stripes on packaging - blue. Chemically pure ("H.Ch.", "HF") acrylic acid HF. The main component content of more than 99%. Color stripes on the package - red. Particularly pure ("OESC") Acrylic Acid Acid. Correction of impurities in such a minor quantity that they do not affect the basic properties. Color stripes on the package - yellow.

Building, nomenclature. Monolay uninustible (unsaturated) acid most often worn historically established names.

The protostic acid of ethylene row is called acrylic acid:

The next representative of this, a series containing 4 carbon atoms, can exist in the track isomeric

The position of the double bond in unsaturated acids in relation to the carboxyl group is denoted by the letters of the Greek alphabet, indicating the places of carbon atoms, between which there is a double bond, with the addition of non-defective acid. For example, vinyl bowl acid is a non-precious acid, and acrylic, crotonic and methacryl - unsaturated acids.

From the structural formulas of these acids it can be seen that the isomerism of non-precious acids depends on the branchiness of the wagon of carbon atoms and the position of the double bond.

Using the example of unsaturated organic acids, we will get acquainted with one of the isomerism bid, which is possessed by various unsaturated organic compounds - geometric isomeria (or, as they are often called, cis-trans-isomeria).

Fig. 16. Model of an ethane molecule.

If you depict the spatial structure of an extreme hydrocarbon molecuer of ethane, then it can be seen that the valence of carbon atoms of ethane is not located in one plane, but at some angle to each other (Fig. 16).

In the etham molecule, the free rotation of carbon atoms around the direction of the ordinary connection without its rupture is possible. It is clear that no matter how navigated atoms of hydrogen around the connection, we will always have the same structure.

Consider now the spatial structure of the milk acid molecule

In a crotonic acid molecule, the free rotation of carbon atoms, as in the molecule of ethane, is no longer possible, since the double bond between carbon atoms would occur.

If in the spatial model of the crotonic acid (Fig. 17, a) we change the right hydrogen and carboxyl group so that hydrogen is under the double bond plane, and the carboxyl group over the plane, then we obtain a different spatial Mr. (Fig. 17, b).

These two spatial models differ from each other in the fact that in the first of these, both hydrogen atoms are located one way from the plane undergoing curtain carbon atoms and a double bond, and in the second - on different sides of it. It may seem that there will be another third isomer of crotonic acid, if in the first spatial model to change the hydrogen atom and the methyl group (Fig. 17, B). However, it is easy to make sure that this model is completely similar to the second, if the entire molecule depicted by the last spatial model, turn around the double bond plane by 180 °.

Fig. 17. Spatial models of crotonic acid molecule.

For convenience, it was agreed upon image of spatial models to use the so-called projection formulas, which are obtained when designing spatial models on the plane. Then the formulas of the crotonic acid will look at:

Such formulas are often depicted somewhat differently, having carbon atoms vertically:

Isomers who have identical atoms or atomic groups (in this case hydrogen atoms) are directed in one direction from the double-bond plane, called cis-isomers, if these substituents are directed to other sides- Trans-isomers.

Thus, geometric yzomeria is one of the types of spatial isomerism and depends on the location of atoms or groups of atoms relative to the double-bond plane.

Spatial isomers differ among themselves and properties. For example, crotonic acid (trans-isomer) is a solid with the pace. Isochoton acid (cis-isomer) - conventional conditions Liquid with pace.

Usually one of the spatial isomers is resistant (stable), and the other - unstable (labile), and the unstable is leisure under the influence of heating, light or chemical effects easily goes into a steady isomer. So, isocrotonic acid is very unstable and easily passes with increased temperature and under action sunlight in stable crotonic acid.

Properties. Lower representatives of non-precious acids - liquids with a sharp smell, well soluble in water. Higher unforeseen acids - solids, odorless, insoluble in water.

For unsaturated acids, most of the reactions of acids of the limit range (the formation of salts, esters, anhydrides, halogen derivatives, etc.) and, moreover, a number of reactions peculiar to non-precious hydrocarbons are characterized.

When the hydrogen is connected in the presence of unsaturated acid catalysts, the acid of the limit range is formed:

With an energetic oxidation, the carbon chain of non-precious acid is broken at a dual connection, and two acids are obtained - a monosular and two-mine:

When heated-cardic acids with diluted mineral acids are formed so-called lactones - oxyc acid internal cyclic esters (see page 169).

For example, from vinyl ace acid under these conditions, U-butyrolacton is formed:

There are other ways to get lactones.

Methods for getting Unfigured acids are similar to methods for obtaining limit acids. For example, unsaturated acids are obtained with careful oxidation of the corresponding non-precious alcohols and aldehydes:

Acrylic acid . Liquid with a sharp odor, heavier than water; pace. From the acrylic acid derivatives, its nitrile has great importance (p. 148) and various ethers. It can be obtained from allyl alcohol.

Currently, acrylic acid industry is obtained by heating ethylene cyanhydrin with dilute sulfuric acid:

Metacryl Acid It turns out in a similar way from acetonecy hygidrine (p. 153). Great importance For the manufacture of organic glass (p. 326) has its methyl ether (methyl methacrylate).

Oleic acid. Its structure is expressed by the formula is an oil liquid (odorless density; Temp. Together with palmitic and stearic acids, it is included in the composition of fats. Oleic acid in especially large quantities It is part of olive, almond and sunflower oils.

When hydrogen is restored, in the presence of catalysts, it turns into an acid of the limit row - stearin. This process plays an important role in the production of Margarine (p. 139).

Under the action of small amounts of nitrogenous acid, oleic acid turns into a solid isomer - elaidic acid.

Olein and elaidinic acids are cis-trans isomers:

From unsaturated acids with two double connections the largest practical value It has sorbic acid. Due to the effective bactericidal properties and the absence of any unwanted side effect The organism of man and animals is sorbic acid and its salts have been applied as preservative funds in the food and other industries.

Sorbic acid is obtained by the interaction of keten (p. 134) with the Crotone aldehyde in the presence of zinc butirate. With this reaction, 3-oxigseanic acid polyester is formed:

When processing the resulting polyester with hydrochloric acid at 70 ° C, a sorbic acid is obtained:

Acrylic acid is one of the simplest representatives of carboxyous uninustible monoxide acids. Its formula is as follows: CH2 \u003d CH-coxy. This is a colorless liquid having a sharp and nasty smell. Soluble in water, chloroform, diethyl alcohol and ethanol, easily polymerizes with the further formation of polyacrylic acid. Acrylic acid has other names: ethencarboxylic acid and propacious acid.

How to get (or synthesized) acrylic acid?
1. Currently, acrylic acid is prepared by steam-oxidated oxidant with oxygen (O2) on molybdenum, cobalt or bismuth catalysts. An example is the following reaction:
CH2 \u003d CH-CH3 (propylene) + o2 (oxygen) \u003d CH2 \u003d CH-coxy (acrylic acid)
2. In the past, a reaction was used in which carbon monoxide II (CO) was interacted, acetylene (CH? CH) and water (H2O). Chemical reaction This will be like this:
CH? CH (acetylene) + co (carbon monoxide II) + H2O (water)? CH2 \u003d CH-coxy (acrylic acid).
Still used the formaldehyde reaction with the coteten:
CH2 \u003d C \u003d O (KOTEN) + H2C \u003d O (formaldehyde)? CH2 \u003d CH-coo (propacious acid).
3. Now the company ROHM AND HAAS creates a special technology of ethencarbonic acid synthesis from propane.
Chemical properties of acrylic acid

The acid under consideration can form salts, esters, anhydrides, amides, chloranhydrides and other connections. It can also join the attachment reaction that are characteristic of ethylene carbon. The addition of water, proton acids and NH3 does not occur on the rule of Markovnikov. At the same time, substituted derivatives are formed. Acrylic acid participates in the synthesis of dienes. It is also condensed with different alikes of Arildiazia. With ultraviolet irradiation, it forms polyacrylic acid.

Application of acrylic kilot

- used as raw materials in the production of a wide range of polymeric products with various chemical and physical properties (for example, plastic and coatings);
- It is used in the production of dispersions for acrylic water paints; At the same time, the scope of such paints will depend on the chemical properties of the copolymer - from the final color vehicle and to painting ceilings;
- acrylic acid and its derivatives are used to create impregnation for skin and tissues, emulsions to paint and varnish materials, as raw materials for acrylate rubbers and polyacrylonitrile fibers, construction adhesives and mixtures; esters of metacryl and acrylic acids (in most cases methyl methyl methacrylate ethers and methylacrylate are used) are used in the production of polymers;
- Often acrylic acid is used in the creation of superabsorbents.

Proper storage of acrylic acid
When storing this substance, inhibitor - hydroquinone is added to avoid polymerization. Before use, the acid must be distilled with caution, since the development of explosion-like polymerization is possible.

Safety when using acrylic acid

When working with acrylic acid, it should be noted that this substance It has an irritant effect on skin and mucous membranes. The threshold of an irritant acid is 0.04 mg / liter. If the eyeballs of the eyeballs come to the mucous membrane, as a rule, causes the strongest corneal burns, can lead to irreversible changes (damage to non-treatable). Inhalation of acrylic acid vapors can cause headache, irritation of the respiratory tract, and in excessive doses - the development of pulmonary edema. In rooms where work with acrylic acid is carried out, constant air control is required. MPC of this acid is 5 mg / meter?. Security measures must be observed when working with other derivatives. As an example, the nitrile of acrylic acid can be brought.

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