RU2502748C1 - Method of producing amidoimides of alkenylsuccinic acid - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: method of producing amidoimides of alkenylsuccinic acid is carried out by reacting aminoamides, obtained by reacting industrial polyamines or a mixture of polyamines with butyric acid or isobutyric acid or oleic acid or stearic acid or stearine, at temperature of 160-190°C for 4-6 hours in molar ratio polyamine: acid of 1-1.1:1, with alkenylsuccinic anhydride, first at temperature of 25-29°C for 0.5 hours, then at 110-115°C for 0.5-1 hours and the obtained mixture is then held at 145-150°C for 3-4 hours. The molar ratio of alkenylsuccinic anhydride to aminoamide is equal to 1:1.1-1.4 and the process is carried out in the presence of industrial oil. The industrial polyamines are selected from diethylenetriamine or triethylenetetramine or N,N'-bis(β-ethylamino)piperazine or tetraethylenepentamine or ethylenediamine.

EFFECT: improved method of producing succinimide additives, wider range of additives and corrosion inhibitors.

5 cl, 2 tbl, 30 ex

Description

The invention relates to the field of petrochemical synthesis, in particular to a method for producing alkenyl succinamidoimides, and can be used as an anti-corrosion, detergent and dispersant additive in lubricating oils to reduce the formation of carbon deposits on parts of internal combustion engines.

The synthesis of alkenyl bis succinimides is known by alkylation of maleic anhydride with tetra- and hexadecenes or with a mixture based on 58% tetradecene, 40% hexadecene and hydroquinone, followed by the reaction of the obtained alkenyl succinic anhydride with tetraethylene pentamine (TEPA) at 130 ° Тame Thrid Mamdouhs. P Petrol and Technol. 2001, 19, No. 5-6b S.547-560; RJH, 2002, 19P229).

A disadvantage of the known additive synthesis method is that it is not effective when used in engine oils due to the low molecular weight of the alkyl radical, but can be used in the manufacture of corrosion inhibitors for the extraction of aromatic hydrocarbons from non-paraffin gas oils. In addition, the individual tetraethylene pentamine used in the synthesis is a deficient substance.

A known method of producing a succinimide additive having detergent, dispersant and anticorrosive properties (US 3309316, Nitrogen and sulfur-containing detergent and anti-corrosion additive for lubricating oils / Me Ninch Herbert A., Karll Robert E. // RZH, 1968, 10P219), which is obtained treatment of the polyisobutenyl succinic anhydride with a nitrogen-containing compound, followed by reaction of the reaction product with a boron-containing compound.

The disadvantage of this method is the low anticorrosion properties and the complex composition of the additive components.

The closest method in technical essence and the achieved result is to obtain a detergent and anticorrosive additive by reacting alkenyl succinic anhydride with free sulfur and further processing the resulting compound with polyethylene polyamine (US 3306908. Reaction products of high molecular weight hydrocarbons substituted succinic acids, amines and metal compounds / Le Suer William M. RZH, 1968, 10P226).

The disadvantage of this method of obtaining additives is its low anticorrosive properties and the complex composition of the components included in the structure of the additive.

The task of the invention is to develop an effective method for the production of alkenylamino acid amidoimides - additives for motor oils, expanding the range of products and using available products as raw materials.

The technical result when using the invention is expressed in the intensification of production, improving product quality.

The above result of the preparation of alkenyl succinic acid amidoimides — anticorrosion additives for lubricating oils — is achieved by the method of producing alkenyl succinic amido imides by the interaction of individual polyamines or a mixture of polyamines with butyric (MK), or isobutyric (IMC), or oleic (Ol.k), or stearic acids (Stearic acid). K.), or stearin, which is a mixture of stearic and palmitic (PC) acids in a molar ratio of 1: 1, at a temperature of 160-190 ° C for 4-6 hours, while the molar ratio of polyamine: acid is is 1-1.1: 1, followed by the interaction of the obtained amino amides of acids with substituted alkenyl succinic anhydride in the presence of a hydrocarbon solvent and an industrial oil initiator, first at a temperature of 25-29 ° C for 0.5 h, then at 110-115 ° C for 0.5-1 h and keeping at 145-150 ° C for 3-4 h, while the molar ratio of alkenyl succinic anhydride: aminoamide is 1: 1.1-1.4.

As alkenyl succinic anhydride use substituted succinic acid anhydride described in patent document RU 2296134, publ. 03/27/2007.

As individual polyamines (PEPA) for the preparation of amidoimides, diethylenetriamine (DETA), or N, N'-bis (β-aminoethyl) piperazine (bis-AEP), or triethylenetetramine (TETA), or tetraethylene pentamine (TEPA), or ethylenediamine ( EDA).

The mixture of polyamines (PEPA mixture) contains, wt.%: H ₂ O - 0.1-0.5; ethylenediamine (EDA) - 0.05-0.2; piperazine - 0.2-0.4; N-β (aminoethyl) piperazine (N-AED) - 2.5-3.5; diethylene triamine (DETA) - 25-35; N, N'-bis (β-aminoethyl) piperazine (bis-AED) - 15-20; triethylenetetramine (THETA) - 30-35; tetraethylene pentamine (TEPA) and other higher amines - the rest.

As industrial oil use oil brand I-20A, or I-40A (GOST No. 20799-88 with amendment 1-5), or mixtures thereof.

where R = (CH ₂ ) ₂ CH ₃ , CH (CH ₃ ) ₂ , C ₁₇ H ₃₃ , C ₁₇ H ₃₅

or

or

Compound 1, R = (CH ₂ ) ₂ CH ₃ , n = 1 [amidoimide (AI) based on DETA, MK and alkenyl succinic anhydride (AAA)];

Compound 2, R = CH (CH ₃ ) ₂ , n = 1 [AI based on DETA, IMC and ALA];

Compound 3, R = C ₁₇ H ₃₃ , N = 1 [AI based on DETA, Ol. K. and the AAA];

Compound 4, R = C ₁₇ H ₃₅ , n = 1 [AI based on DETA, Art. and AAA];

Compound 5, R = C ₁₇ H ₃₅ and C ₁₉ H ₃₁ , n = 1 [AI based on DETA, St. K., PC and AA];

Compound 6, R = (CH ₂ ) ₂ CH ₃ , n = 2 [AI based on TETA, MK and AAA];

Compound 7, R = CH (CH ₃ ) ₂ , n = 2 [AI based on TETA, IMC and AAA];

Compound 8, R = C ₁₇ H ₃₃ , n = 2 [AI based on TETA, Ol. K. and the AAA];

Compound 9, R = C ₁₇ H ₃₅ , n = 2 [AI based on TETA, Art. and AAA];

Compound 10, R = C ₁₇ H ₃₅ + C ₁₅ H ₃₁ (1: 1), n = 2 [AI based on TETA, St. K., PC and AA];

Compound 11, R = (CH ₂ ) ₂ CH ₃ , n = 3 [AIs based on TEPA, MK and AAA];

Compound 12, R = CH (CH ₃ ) ₂ , n = 3 [AI based on TEPA, IMC and AAA];

Compound 13, R = C ₁₇ H ₃₃ , n = 3 [AI based on TEPA, Ol. K. and the AAA];

Compound 14, R = C ₁₇ H ₃₅ , n = 3 [TEPA-based AI, Art. and AAA];

Compound 15, R = C ₁₇ H ₃₅ + C ₁₅ H ₃₁ (1: 1), n = 3 [AI based on TEPA, St. K., PC and AA];

Compound 16, R = (CH ₂ ) ₂ CH ₃ , n = 3 [AI based on bis-AED, MK and AAA];

Compound 17, R = CH (CH ₃ ) ₂ , n = 3 [AI based on bis-AED, BCA and AAA];

Compound 18, R = C ₁₇ H ₃₃ , n = 3 [AI based on bis-AED, Ol. K. and the AAA];

Compound 19, R = C ₁₇ H ₃₅ , n = 3 [AI based on bis-AED, St. and AAA];

Compound 20, R = C ₁₇ H ₃₅ + C ₁₅ H ₃₁ (1: 1), n = 3 [AI based on bis-AED, St. K., PC and AA];

Compound 21, R = (CH ₂ ) ₂ CH ₃ , n = 0 [AI based on EDA, MK and AAA];

Compound 22, R = CH (CH ₃ ) ₂ , n = 0 [AI based on EDA, IMC and AAA];

Compound 23, R = C ₁₇ H ₃₃ , n = 0 [AI based on EDA, Ol. K. and the AAA];

Compound 24, R = C ₁₇ H ₃₅ , n = 0 [AI based on EDA, St. and AAA];

Compound 25, R = C ₁₇ H ₃₅ + C ₁₅ H ₃₁ (1: 1), n = 0 [AI based on EDA, St. K., PC and AA];

Compound 26, R = CH (CH ₃ ) ₂ , n = 1-3 [AI based on a mixture of PEPA, IMA and AAA];

Compound 27, R = (CH ₂ ) ₂ CH ₃ , n = 1 [AI based on DETA, MK and AAA];

Compound 28, R = CH (CH ₃ ) ₂ , n = 2 [AI based on TETA, IMC and AAA];

Compound 29, R = C ₁₇ H ₃₃ , n = 2 [AI based on bis-AED, Ol. K. and the AAA];

Compound 30, R = C ₁₇ H ₃₅ , n = 3 [AI based on TEPA, St. and AAA]. The invention is illustrated by the following examples:

Example 1. In a reactor equipped with a mechanical stirrer, a thermometer, a refrigerator and a dropping funnel, 20.6 g (0.2 mol) of diethylene-triamine (DETA) and 17.6 g (0.2 mol) of butyric acid are charged. The molar ratio of DETA: MK is 1: 1. The reaction mixture is stirred at a temperature of 160 ° C for 4 hours, at the same time produce distillation of water and lightly boiling components. The reaction mixture is cooled to 60-65 ° C and 34 g of I-20A oil (mass ratio of aminoamide: oil is 1: 1) is added to the obtained aminoamide of acids and 150 g (0.2 mol) of a solution of alkenyl succinic anhydride (AAA) in oil are dosed I-20A (mass ratio of AA and oil is 1: 1). The molar ratio of aminoamide: AA is 1.1: 1. The reaction mixture is heated first at a temperature of 25-29 ° C for 0.5 h, then at 110-115 ° C for 0.5 h and kept at a temperature of 145 ° C for 3 h, after which the mixture is cooled to 70 ° C. vacuum is connected to the system and water and low boiling substances (impurities contained in raw materials and partial decomposition of products) are distilled off at 120-125 ° C (7-12 mm Hg), then the contents of the reactor are cooled to 60 ° C and filtered through a cloth filter.

Received 172.3 g (95.2%) of alkylene succinamidoimide (compound 1).

The formation of amidoimide (1) is confirmed by the formation of an equimolar amount of water.

Example 2. Under the conditions of example 1, 10.8 g (0.105 mol) of DETA and 8.8 g (0.1 mol) of isobutyric acid (IMA) are charged to the reactor. The molar ratio of DETA: IMC is 1.05: 1. The reaction mixture was stirred at 160 ° C for 4 hours, water and light impurities were distilled off, then the contents of the reactor were cooled to 65 ° C, 18 g of I-40A oil was added and 75 g (0.1 mol) of AAA was dosed in 75 g of oil I-40A. The mass ratio of aminoamide: oil is 1: 1, and AAA: oil is 1: 1. The mixture is first heated at a temperature of 25-28 ° C for 0.5 h, then at 110 ° C for 45 min and kept at 145 ° C for 3 h, water is distilled off at 125 ° C (7-8 mm RT. Art.), after which the mixture is cooled to 65 ° C and amidoimide (2) is filtered through a cloth filter.

Received 87.7 g (96.4%) of compound (2).

In the reaction of the formation of aminoamide and alkylene succinamidoimide (2), equimolar amounts of water were isolated.

Example 3. Under the conditions of example 1, 11.33 g (0.11 mol) of DETA, 28.2 g (0.1 mol) of oleic acid (Ol. K.) are charged into the reactor. The molar ratio of DETA: Ol. K. is 1.1: 1. The mixture was heated at 170 ° C for 5 hours, water and impurities were distilled off, the contents of the reactor were cooled to 60 ° C, and 36.5 g of I-20A oil was added at this temperature. The mass ratio of aminoamide: oil is 1: 1. Then, 75 g (01 mol) of AAA in 75 g of oil are dosed to the aminoamide solution (mass ratio of AAA: oil is 1: 1). The contents of the reactor are first heated at 26-29 ° C for 0.5 h, at 115 ° C for 1 h and kept at 145-148 ° C for 3.5 h. Water and impurities are distilled off in vacuum and the target product ( 3) filtered.

Received 107.15 g (97.5%) of compound (3).

Example 4. Under the conditions of example 1, 10.3 g (0.1 mol) of DETA, 28.4 g (0.1 mol) of stearic acid (St.k.) are charged into the reactor. The molar ratio of DETA: is 1: 1. The reaction mixture is heated at 180 ° C for 6 hours (until an equimolar amount of water is isolated), water and impurities are removed, 3.6 g of a mixture of I-20A and I-40A oil are added to the contents of the reactor (mass ratio 1: 1). The mass ratio of aminoamide: oil (1: 1). Then 75.0 g (0.1 mol) of AA are dosed in 75 g of a mixture of I-20A and I-40A oil (1: 1) and stirred at 25-29 ° C for 0.5 h, at 115 ° C for 1 h and the reaction mixture was kept at 148-150 ° С for 3.5 h. Water and impurities of low-boiling components were removed, alkenyl succinamidoimide (4) was filtered off.

Received 104.48 g (94.9%) of compound (4).

Example 5. Under the conditions of example 1, 10.3 g (0.1 mol) of DETA are loaded into the reactor, 27.0 g of stearin - [mixture of stearic and palmitic acids (1: 1)] - 14.2 (0.05 mol) St. and 12.8 g (0.05 mol) of palmitic acid (PC). The molar ratio of DETA: and PC is 1: 1. The mixture is heated at 180 ° C for 6 hours. After removal of water and impurities, 35 g of I-20A oil is added to the reaction mixture (mass ratio of aminoamide: oil is 1: 1) and 75.0 g (0.1 mol) are dosed. AAA in 75 g of I-20A oil. The mixture is heated first at 29 ° C for 0.5 h, then at 115 ° C for 1 h and kept at 148-149 ° C for 3.5 h, after which water and impurities are distilled off in vacuo.

Received 101.9 (93.8%) of compound (5).

Example 6. Under the conditions of example 1, 14.6 g (0.1 mol) of triethylenetetramine (TETA), 8.8 g of butyric acid (MK) are loaded into the reactor (molar ratio of TETA: MK is 1: 1). The mixture is heated at 160 ° C for 5 hours, then 21 g of I-40A oil is added (weight ratio aminoamide: oil 1: 1). Then 95.0 g (0.1 mol) of AAA in 95 g of I-40A oil are dosed to the aminoamide solution (mass ratio of AAA and oil is 1: 1) and heated first at 25-27 ° C for 0.5 h, at 110 ° C for 0.5 hours and incubated at 145-147 ° C for 3.5 hours

Received 112.6 g (98.1%) of compound (6).

Example 7. Under the conditions of Example 1, from 20.44 g (0.14 mol) of TETA and 12.32 g (0.14 mol) of IMC, an aminoamide is obtained which is reacted with 95.0 g (0.1 mol) of AA in oil environment. The molar ratio of aminoamide: AA is 1.4: 1.

Received 123.94 g (98.4%) of compound (7).

Example 8. Under the conditions of example 1, 14.6 g (01 mol) of TE-TA, 28.2 g (0.1 mol) of ol. K. The mixture is heated at 180 ° C for 6 hours, water is distilled off and 41.0 g of I-40A oil is added to the mixture (mass ratio of aminoamide: oil is 1: 1) and 80.0 g (0.1 mol) are dosed. AAA in 80 g of I-40A oil (mass ratio AAA: oil is 1: 1), heated at a temperature of 28-29 ° C for 0.5 h, at a temperature of 110-115 ° C for 1 h and kept at 146 -149 ° C for 3.5 hours

Received 115.98 g (97.3%) of alkenylsuccinamidoimide (8) (compound 8).

Example 9. Under the conditions of example 1, 17.52 g (0.12 mol) of TETA, 34.08 g (0.1 mol) of Art. (molar ratio 1: 1), heated at 180 ° С for 6 h, water and low boiling components are distilled off, 41 g of I-20A oil are added, 120 g (0.1 mol) of AA are dosed in 120 g of oil (molar ratio of aminoamide : AA is 1.2: 1), the reaction mixture is heated at 28-29 ° C for 0.5 h, at 115 ° C for 1 h and kept at 147-150 ° C for 3.5 h. Water and impurities (decomposition products) are distilled off in vacuo, the product (9) is filtered off.

Received 162.83 g (95.9%) of amidoimide (9).

Example 10. In the reactor load of 16.06 g (0.11 mol) of TETA, 27.0 g of stearin (0.05 mol of St.k. and PC). The molar ratio of TETA: stearin is 1.1: 1. The mixture is heated at 180 ° C for 6 hours, at the same time water and impurities are removed, after which 40 g of I-20A oil (mass ratio 1: 1) are added and 80.0 g (0.1 mol) of AA are dosed in 80 g of oil I-20A. The mixture is heated at 28-29 ° C for 0.5 h, at 115 ° C for 1 h and kept at 146-149 ° C for 3.5 h. Then, water and low boiling components are distilled off (impurities contained in the feed and decomposition products).

Received 111.27 g (94.3%) of compound (10).

Example 11. To the reactor load 18.9 g (0.1 mol) of tetraethylene pentamine (TEPA), 8.8 g MK (molar ratio of TEPA: MK is 1: 1), heated at 180-190 ° C for 6 hours, water is distilled off, then 26.0 g of I-40A oil is added (mass ratio of aminoamide: oil is 1: 1), and then 95.0 g (0.1 mol) of AAA is dosed in 95.0 g of I-40A oil. The mixture is heated at 25-29 ° C for 0.5 h, then at 115 ° C for 1 h and kept at 145-148 ° C for 4 h, water and boiling components are distilled in vacuum.

Received 116.47 g (97.8%) of compound (11).

Example 12. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA are charged into the reactor, 8.8 g (0.1 mol) of IMC give an aminoamide which is reacted with 95.0 g (0.1 mol) АЯА in the environment of I-20A oil.

Received 116.12 g (97.5%) of compound (12).

Example 13. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA, 28.2 g (0.1 mol) of Ol are charged into the reactor. to. (molar ratio 1: 1). The mixture is heated at a temperature of 180-190 ° C for 6 hours, after distilling off the water, 45.0 g of I-40A oil is added (the mass ratio of aminoamide: oil is 1: 1) and 75.0 g (0.1 mol) of AA are dosed in 75.0 g of I-40A oil (mass ratio of aminoamide: oil is 1: 1), heated at 28-29 ° C for 0.5 h, then at 115 ° C for 1 h and kept at 145-149 ° C for 4 hours

Received 114.94 g (97.0%) of compound (13).

Example 14. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA, 28.4 g (0.1 mol) of St.k. (molar ratio of TEPA: St.k. is 1: 1). The mixture was heated at 190 ° C for 6 hours, water was distilled off, then 45.5 g of I-20A oil was added to the reaction mixture and 95.0 g (0.1 mol) of AAA was dosed in 95.0 g of I-20A oil. The reaction mixture is heated at 25-29 ° C for 0.5 h, at 115 ° C for 1 h and kept at 147-149 ° C for 4 h. After distillation of water and impurities in vacuum, the product is filtered off.

Received 131.48 g (94.8%) of compound (14).

Example 15. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA, 27.0 g of stearin (0.05 st. K. and PC) are loaded into the reactor. The mixture is heated at 180-190 ° C for 6 hours, water and impurities are removed, 44.0 g of a mixture of I-20A and I-40A oils (mass ratio 1: 1) are added to the contents of the reactor and 120.0 g (0 , 1 mol) AAA in 120.0 g of I-20A and I-40A oil (mixture mass ratio 1: 1), heated at 25-29 ° C for 0.5 h, at 115 ° C for 1 h and maintained at 147-149 ° C for 4 hours, at the same time remove water and boiling components in a vacuum.

152.72 g (94.1%) of compound (15) were obtained.

Example 16. Under the conditions of Example 1, 22.36 g (0.13 mol) of N, N'-bis (β-aminoethyl) piperazine (bis-AED), 11.44 g (0.13 mol) of MK ( molar ratio 1: 1), heated at 160 ° C for 5 h. Water was distilled off and 24.0 g of I-20A oil was added (mass ratio of aminoamide: oil was 1: 1), then 80.0 g (0, 1 mol) AAA in 80.0 g of I-20A oil. The molar ratio of aminoamide: AA is 1.3: 1. The reaction mixture is heated at 25-29 ° C for 0.5 hours, at 110 ° C for 0.5 hours and kept at 145-149 ° C for 4 hours. Water and impurities are distilled off in vacuo.

Received 110.43 g (98.6%) of alkenylsuccinamidoimide (16).

Example 17. Under the conditions of Example 1, from 17.2 g (0.1 mol) of bis-AED and 8.8 g (0.1 mol) of IMC, an aminoamide is obtained to which 24.0 g of I-20A oil is added and reacted with 80.0 g (0.1 mol) of AA in 80.0 g of I-20A oil.

Received 100.55 g (98.2%) of compound (17).

Example 18. Under the conditions of example 1, 17.2 g (0.1 mol) of bis-AED, 28.2 g (0.1 mol) of Ol are charged into the reactor. K., heated at 170-180 ° C for 6 hours. After distillation of water, 44.0 g of I-40A oil was added to the mixture (mass ratio of aminoamide: oil is 1: 1), then 95.0 g (0, 1 mol) AAA in 95.0 g of I-40A oil. The mixture is heated at 25-29 ° C for 0.5 h, at 110-115 ° C for 1 h and kept at 148-149 ° C for 3.5 h. After the water is distilled off, the product (18) is filtered off.

Received 133.79 g (97.8%) of compound (18).

Example 19. Under the conditions of example 1, 17.2 g (0.1 mol) of bis-AED, 28.4 g (0.1 mol) of Art. The mixture is heated at 180-190 ° C for 6 hours. After distillation of the water, 44.0 g of I-40A oil is added to the mixture and 75.0 g (0.1 mol) of AA is dosed in 75.0 g of I-40A oil. The mixture is heated at 28-29 ° C for 0.5 h, at 115 ° C for 1 h and incubated for 3.5 h. After distillation of water in vacuum, the product (19) is filtered off.

113.13 g (96.7%) of compound (19) were obtained.

Example 20. Under the conditions of Example 1 and 19, from 18.92 g (0.11 mol) of bis-AED and 27.0 g of stearin (molar ratio of bis-AED: stearin is 1.1: 1), the aminoamide is dosed. 75.0 g (0.1 mol) of AA in 75.0 g of I-20A oil.

Received 109.58 g (94.8%) of compound (20).

Example 21. Under the conditions of example 1, 12.0 g (0.2 mol) of ethylenediamine (EDA), 17.6 g (0.2 mol) of MK are charged to the reactor, the mixture is heated to 160 ° C and maintained at 160 ° C. for 4 hours, then distillate water and boiling impurities. Then, 24.0 g of I-40A oil (mass ratio of aminoamide: oil is 1: 1) is added to the reaction mixture and 180.0 g (0.2 mol) of AA is dosed in 180.0 g of I-40A oil, heated at 25 -29 ° C for 0.5 h, at 110 ° C for 1 h and kept at 145 ° C for 3 h. Received 187.57 g (93.6%) of compound (21).

Example 22. Under the conditions of Example 1 and 21, from 12.0 g (0.2 mol) of EDA and 17.6 g (0.2 mol) of IMC, an aminoamide is obtained to which 160.0 g (0.2 mol) of AAA is added. .

Received 169.98 g (93.4%) of product (22).

Example 23. In the conditions of example 1 and 21 of 13.2 g (0.2 mol) of EDA, 56.4 g (0.2 mol) of Ol. K. (the molar ratio of EDA: Ol. to. equal to 1.1: 1) and 180.0 g (0.2 mol) of AA in oils (mixture of I-20A and I-40A) synthesize compound (23).

224.55 g (93.1%) of product (23) are obtained.

Example 24. In the conditions of example 1 and 21 of 12.0 g (0.2 mol) EDA, 56.8 g (0.2 mol) and 150.0 g (0.2 mol) of ANA give 185.22 g (92.8%) of alkenyl succinamidoimide (24).

Example 25. Under the conditions of Example 1, 12.0 g (0.2 mol) of EDA, 54.0 g of stearin (0.05 St. And 0.05 PK) were loaded into the reactor, heated to 160 ° C and held at 160-180 ° C for 5 hours. Water and impurities are removed and 62.0 g of I-20A oil is added to the reaction mixture, then 150.0 g (0.2 mol) of AAA are dosed in 150.0 g of I-20A oil and heated at 25-29 ° C for 0.5 h, at 110-115 ° C for 1 h and kept at 147-149 ° C for 3.5 h. Water and impurities were removed in vacuo, the amidoimide was filtered off.

Received 195.64 g (93.7%) of compound (25).

Example 26. Under the conditions of example 1, 16.0 g (0.1 mol) of a PEPA mixture (average molecular weight 160) of the following composition, wt.%: H ₂ O — 0.15; EDA-0.1; DETA-26; N- (β-aminoethyl) piperazine (AED); bis-AEP-15.5; TETA-32; TEPA and other higher amines - the rest, 8.8 g (0.1 mol) of IMC, are heated at 160-170 ° С for 5 h, then water and low boiling impurities are distilled off. The mixture is cooled to 60 ° C, 21.0 g of I-20A oil is added (mass ratio of aminoamide: oil is 1: 1) and 90.0 g (0.1 mol) of AAA are dosed in 90.0 g of I-20A oil. The reaction mixture is heated at 25-29 ° C for 0.5 h, at 115 ° C for 1 h and kept at 145-149 ° C for 3.5 h, water and light impurities are distilled off in vacuum.

Received 108.42 g (97.5%) of a mixture of amidoimides (26).

Example 27. Under the conditions of example 1, 20.6 g (0.2 mol) of DETA, 19.36 g (0.22 mol) of MK (molar ratio of DETA: MK is 1.1: 1) are loaded into the reactor, heated at 130 -140 ° C for 3 hours, water and boiling substances are distilled off, the solution is cooled to 60-65 ° C, then 35.0 g of I-40A oil is added to the mixture (molar ratio of aminoamide: oil is 1: 1) and 160 , 0 g (0.2 mol) of AAA in 160.0 g of I-20A oil is heated at 120-130 ° C for 2 hours and the low-boiling components are distilled in vacuum.

78.88 g (71.2%) of amidoimide (27) are obtained.

Example 28. Under the conditions of Example 1, by heating 14.6 g (0.1 mol) of TETA, 8.8 g (0.1 mol) of IMC at a temperature of 130 ° C for 8 hours, an aminoamide is obtained, which is 75.0 g ( 0.1 mol) AAA at 160 ° C for 5 h gives amidoimide (28).

51.53 g (68.9%) of amidoimide (28) are obtained.

Example 29. Under the conditions of Example 1, 17.2 g (0.1 mol) of bis-AED, 22.56 g (0.08 mol) of Ol are charged into the reactor. K. (molar ratio of bis-AED: Ol. to. equal to 1: 0.8), the mixture is heated at 200 ° C for 7 hours, after distillation of water and adding the appropriate amount of oil (molar ratio of aminoamide: oil is 1: 1 ) 95.0 g (0.1 mol) of AA are metered into the reaction mixture and heated at 150-160 ° C for 6 hours. The color of amidoimide (29) has become dark brown.

Received 96.17 g (70.3%) of product (29).

Example 30. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA, 28.4 g (0.1 mol) of Art. (molar ratio of TEPA: St.c. is 1: 1, heated at 140-150 ° С for 3 hours. 120.0 g (0.1 mol) of ААА are dosed to the aminoamide solution, the mixture is heated at 130-135 ° С within 6 hours

Received 121.82 g (74.6%) of product (30).

The IR spectra of the obtained amidoimides have absorption bands at 1645 cm –1, characteristic of the amide group, at 1720 and 1780 cm ^–1 , characteristic of the C = O group in five-membered imides.

Table 1 shows the test results of amidoimides (1-30) as additives according to TU 38101146-77. Substituted succinic anhydride (alkylene succinic anhydride) was obtained under the conditions described in patent RU 2296134, publ. 03/27/2007.

Examples (1-26) provided that the declared parameters of the process for the production of alkenyl succinic acid amidoimides are maintained, confirm a high yield (92.8-98.2%) and the conformity of the test results of TU 38 101146-77 for succinimide additives (see table 1, paragraph 1 -26).

Examples (27-30) provided that deviations from the stated parameters of the process for the production of alkenyl succinic amidoimides confirm a decrease in yield (68.9-74.6%) and product quality.

The products in the examples (27-30) do not comply with the technical specifications in terms of "mass fraction of active substance", "mass fraction of free amines", "flash point".

Table 2 shows the test results of the compounds (compounds 1-30) as a corrosion inhibitor. From table 2 it is seen that the compositions (1-26) show a protective effect from 94.8 to 99.6%.

Examples 27-30 indicate that a deviation from the process parameters claimed in the claims also leads to a decrease in the protective properties of the target products (88.7-90.2%) (see table 2, p. 27-30).

Table 1 Test results of amidoimides (1-30) as additives according to TU 38 101 146-77 Connections The name of indicators Amine number, mg HCl per 1 g of additive, not less than Acid number, mg KOH per 1 g of additive, not more than Mass fraction of nitrogen in the additive,%, not less Mass fraction of mechanical impurities,%, no more Mass fraction of water,%, no more Mass fraction of active substance,%, not less Mass fraction of free polyamines,%, no more Flash point determined in an open crucible, ° С, not less than Norm according to TU 38 101 146-77 twenty 4.0 2,4 0.06 0.1 40 0.2 160 one 2 3 four 5 6 7 8 9 one 24.2 2,3 2.6 0.02 0.02 44,2 0.1 172 2 24.8 2.9 3.3 0.04 0,03 45.9 0.16 185 3 22.1 2.9 2,8 0.04 0.08 42,2 0.1 170 four 22.7 2.7 2.7 0.02 0.05 43.9 0.15 172 5 21.9 2,3 2.6 0.05 0,03 42.8 0.14 173 6 21.0 3.2 2.7 0,03 0.02 46.3 0.14 182 7 26.8 2,8 2,5 0.04 0.05 46.6 0.08 185 8 22.4 2,8 2.7 0.04 0.06 43.3 0.09 173 9 22.4 3,1 2,5 0.01 0,07 42.8 0.18 168 10 23.7 3.2 2,4 0.02 0,03 41.9 0.16 164 eleven 22.5 3.0 3.0 0.05 0.05 45.1 0.08 175 12 22.3 3.2 2,4 0.05 0,07 46.9 0.15 170 13 24.6 3,1 2,8 0.06 0.08 46,4 0,07 180 fourteen 22.0 3.6 2,5 0.02 0,07 42.6 1.12 166 fifteen 22.2 3.8 2.6 0,03 0.06 41.2 1.14 164

The end of table 1. one 2 3 four 5 6 7 8 9 16 25.7 2.2 3.2 0.01 0.08 48,2 1,11 177 17 26.1 2,4 3.4 0,03 0.05 47.6 0.1 179 eighteen 25.3 2.9 3,1 0.02 0.06 46.6 0.18 176 19 25.6 2,8 3.0 0,03 0,07 45.8 0.14 172 twenty 24.9 2.7 3.2 0.04 0.09 46.7 0.16 170 21 21,2 2.9 2,5 0.01 0,03 41.0 0.15 163 22 21,4 2,8 2,4 0,03 0.04 42.0 0.16 162 23 21.8 2.9 2.6 0.05 0.08 42.5 0.13 164 24 21.0 2,5 2,5 0.04 0,07 41.1 0.18 165 25 21.3 2,5 2,4 0,03 0.05 41.8 0.17 161 26 24.6 2,8 2,8 0.02 0.04 46.2 0.13 174 27 20.5 3.3 2,4 0.04 0,07 39.8 0.3 158 28 20.8 4.2 2,3 0.05 0.09 38.5 0.4 155 29th 28.8 2.6 2,5 0,03 0.08 39.0 0.6 153 thirty 22.8 4.3 2,4 0.02 0,07 37.5 0.3 152

table 2 The test results of compounds (1-30) for protective activity No. p / p Corrosion Inhibitor Composition Molar ratio Inhibitor Dosage, mg / L Degree of protection, % one 2 3 four 5 one DETA: MK: amide: AAA 1: 1: 1.1: 1 fifty 98.8 2 - DETA: IMC: amide: AAA 1.05: 1: 1: 1 fifty 99.3 3 DETA: All.k: amide: AAA 1.1: 1: 1: 1 thirty 98.5 four DETA: St.k.: amide: AAA 1: 1: 1: 1 thirty 97.4 5 DETA: Stearin: amide: AAA 1: 1: 1: 1 fifty 97.1 6 TETA: MK: amide: AAA 1: 1: 1: 1 fifty 99,2 7 THETA: IMC: amide: AAA 1: 1: 1.4: 1 fifty 99.1 8 TETA: Ol.c.: amide: AAA 1: 1: 1: 1 fifty 99.1 9 TETA: St.k.: amide: AAA 1: 1: 1.2: 1 thirty 95.8 10 TETA: Stearin: amide: AAA 1.1: 1: 1: 1 fifty 97.08 eleven TEPA: MK: amide: AAA 1: 1: 1: 1 fifty 99.3 12 TEPA: IMC: amide: AAA 1: 1: 1: 1 fifty 98.6 13 TEPA: Ol.c.: amide: AAA 1: 1: 1: 1 fifty 98.3 fourteen TEPA: St.k.: amide: AA 1: 1: 1: 1 thirty 97.2 fifteen TEPA: Stearin: amide: AAA 1: 1: 1: 1 fifty 97.15 16 bis-AED: MK: amide: AAA 1: 1: 1.3: 1 thirty 99,4 17 bis-AEP: IMC: amide: AAA 1: 1: 1: 1 fifty 99.6 eighteen bis-EP: Ol.k.: amide: AAA 1: 1: 1: 1 fifty 99.5 19 bis-AED: St. K.: amide: AAA 1: 1: 1: 1 fifty 97.8 twenty bis-AED: Stearin: amide: AAA 1.1: 1: 1: 1 fifty 98.2 21 EDA: MK: amide: AAA 1: 1: 1: 1 fifty 95.4 22 EDA: IMC: amide: AAA 1: 1: 1: 1 fifty 95.3 23 EDA: Ol.c.: amide: AAA 1.1: 1: 1: 1 thirty 94.8 24 EDA: St.c .: amide: AAA 1: 1: 1: 1 fifty 95.2 25 EDA: Stearin: amide: AAA 1: 1: 1: 1 fifty 95.1 26 PEPA mixture: IMC: amide: AAA 1: 1: 1: 1 fifty 99.15 27 DETA: MK: amide: AAA 1: 1.1: 1: 1 fifty 88.7 28 THETA: IMC: amide: AAA 1: 1: 1: 1 fifty 88.8 29th bis-AED: Ol.k.: amide: AAA 1: 0.8: 1: 1 fifty 89.4 thirty TEPA: St.k.: amide: AA 1: 1: 1.3: 1 fifty 90.2

Claims (5)

1. A method for producing alkenyl succinic acid amidoimides by reacting alkenyl succinic anhydride with polyamines at an elevated temperature in the presence of a hydrocarbon solvent and initiator, characterized in that the aminoamides obtained by reacting individual polyamines, or a mixture of polyamines with butyric, or isobutyric, or oleic, or stearic acids, or stearin at a temperature of 160-190 ° C for 4-6 hours, while the molar ratio of polyamine: acid is 1-1.1: 1, interact with alkenyl succinic anhydride in the presence of a hydrocarbon solvent and an industrial oil initiator, first at a temperature of 25-29 ° C for 0.5 h, then at 110-115 ° C for 0.5-1 h and kept at 145-150 ° C for 3 -4 hours in a molar ratio of alkenyl succinic anhydride: aminoamide equal to 1: 1.1-1.4. 2. The method according to claim 1, characterized in that diethylene triamine, or triethylenetetramine, or N, N'-bis (β-aminoethyl) piperazine, or tetraethylene pentamine, or ethylenediamine are used as individual polyamines. 3. The method according to claim 1, characterized in that a mixture of polyamines of the following composition is used, wt.%: H ₂ O 0.1-0.5; ethylenediamine 0.05-0.2; piperazine 0.2-0.4; N-β (aminoethyl) piperazine 2.5-3.5; diethylene triamine 25-35; N, N'-bis (β-aminoethyl) piperazine 15-20; triethylenetetramine 30-35; tetraethylene pentamine and other higher amines the rest. 4. The method according to claim 1, characterized in that the industrial oil is used industrial oil brand I-20A, or I-40A, or mixtures thereof. 5. The method according to claim 1, characterized in that the stearin is a mixture of stearic and palmitic acids in a molar ratio of 1: 1.