Method for preparing 2,6-di-(3,3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)-cyclohexane-1-one

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to an improved method for synthesis of 2,6-di-(3,3',5,5'-di-tert.-butyl-4,4'-oxybenzyl)-cyclohexane-1-one used as a stabilizing agent of polyolefins and low-unsaturated carbon=chain rubbers. Method involves interaction of cyclohexanone with N,N-dimethyl-(3,5-di-tert.-butyl-4-oxybenzyl)amine in the ratio = (1-1.2):2, respectively, and process is carried out at temperature 125-145°C up to ceasing isolation of dimethylamine. Method provides simplifying technology and preparing the end product with the yield 61-85.4%.

EFFECT: improved method of synthesis.

12 tbl, 23 ex

 

The invention relates to a chemical compound class spatial difficult phenols that can be used as a stabilizer for polyolefins and nizkoenergetickych chain rubbers.

The closest in technical essence is a method of obtaining 2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-she by reacting cyclohexanone with Basilisk reagent, and as benzylurea reagent take halide 3,5-dialkyl-4-hydroxybenzyl in a molar excess as the solvent used dioxane and the process is continued for 2.5 hours at the boiling temperature of the solvent. After heating the reaction mass of water is added to perform hydrolysis and continue mixing for another 15 minutes. Then the reaction mass is subjected to fractional distillation under a pressure of 0.08 mm Hg in the temperature range 147-183°With distilled viscous fraction, which is then recrystallized in isopropyl alcohol. The resulting product is a powder with a melting point 87-88°C. Analytical analysis shows that this substance is monosubstituted derivative, i.e. the 2-(3,5-di-tert-butyl-4-hydroxybenzyl)-cyclohexanone. The residue remaining in the reaction flask after the distillation, twice recrystallized in isopropyl alcohol. Received link is on is a white crystals with a melting point 221-223° And, according to NMR analysis, is a 2,6-bis(3,5-di-tert-butyl-4-hydroxybenzyl)cyclohexanone [see US 3631148 The B.F.Goodrich Company), 28.12.1971; US 3594424 The B.F.Goodrich Company), 20.07.1971].

The disadvantages of this method are the multistage process, the complexity of the separation of the mixture of products and not a high yield of the target product.

The objective of the invention is to simplify the process, increasing the yield of the 2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-it (I).

The technical problem is solved by a method of obtaining 2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-she by reacting cyclohexanone with Basilisk reagent, followed by separation of the target product, where as benzylurea reagent take the N,N-dimethyl-(3,5-di-tert-butyl-4-oxybenzyl)amine in a ratio of cyclohexanone and N,N-dimethyl-(3,5-di-tert-butyl-4-oxybenzyl)amine (1÷1,2):2, respectively, and the process is conducted at a temperature of 125-145°s to stop shedding dimethylamine.

Technical solution allows to obtain a target product in a single stage with output up to 86%.

The invention is illustrated by the following examples of specific performance.

Example 1.

2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-he get in one stage by reacting N,N-dimethyl-(3,5-di-tert-b is Tyl-4-oxybenzyl)Amin (Ω) with cyclohexanone (CG) with a ratio of Ω:CG=2:1,05 at a temperature of 135° And low vacuum up to 740 mm Hg to stop shedding dimethylamine, followed by separation of the target product, for example by recrystallization.

Examples 2-10 similar to example 1.

The ratio of the reagents, the performance conditions for obtaining the claimed chemical substances, the product yield from 1 to 10 examples of specific performance are shown in table 1.

Table 1
# examplePerformance conditionsThe melting temperature of the target product, °The yield of the target product, %
Mole of soothes. OM:TTTemperature interaction, °Pressure, mm Hg
12:1,0513574022374,1
22:1,113566022373,4
32:1,113566022375,8
42:1,114060022383,9
52:1,114066022374,0
621,0 14066022362,6
72:1,1125710221-22361,5
82:1,113566022363,0
92:1,213570022385,4
102:1,0145735222-22362,6

Example 11.

2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-it is produced by the interaction of N,N-dimethyl-(3,5-di-tert-butyl-4-oxybenzyl)Amin (Ω) with cyclohexanone (CG) with a ratio of Ω:CG=2:1,05 at a temperature of 135°when bubbling through the reaction mass with an inert gas before the termination of allocation dimethylamine, followed by separation of the target product.

Examples 12-15 analogous to example 11. The ratio of the reagents, the performance conditions for obtaining the claimed chemical substances, the product yield from 11 to 15 examples of specific performance are shown in table 2.

Table 2
# examplePerformance conditionsThe melting temperature of the target product, °You are the od of the target product, %
Mole of soothes. OM:TTInert gasTemperature interaction, °
112:1,05nitrogen14522370,25
122:1,05argon14522370,25
132:1,05nitrogen13522357,14
142:1,05nitrogen13522364,87
152:1,1nitrogen14522385,79

The claimed chemical compound target product 2,6-di(3',5'-di-tert-butyl-4'-oxybenzyl)-cyclohexane-1-it, then the stabilizer is a crystalline white powder, odorless, has a low volatility. TPL=223°C. the Structure of the claimed chemical substances confirmed by NMR1N-spectroscopy. The composition of the claimed chemical substances confirmed by elemental analysis. An NMR spectrum1N (δ, ppm): HAr 6.980s; HE 5.803s; CH31,412s; CH2-Ar quadruplet; a pair of CH21,44m; meta-CH21,3m. Elemental analysis data. Found, %: C 80,52; N 10,04; 534 MM. With36H54O3. Calculated, %: C 80,90; N 10,11; 8,99. M 534.

Examples of the use of 2,6-di(3',5'-di-tert-butyl-4'-oxybenzyl)-cyclohexane-1-she as a stabilizer.

Examples 16, 17.

The introduction of stabilizers in polyolefin low-pressure polyethylene (HDPE) is as follows. A portion of the polymer and the stabilizer is subjected to rolling at 160±5° (length rolls 260 mm, roll diameter 100 mm, the speed of rotation of the rolls 28 rpm, time, rolling 5±1 min). Razvaltsovannye in fabric for 5 min at the same temperature with constant trimming blade. Of rolled cloth pressed plate according to GOST 16338-85 open the mold at a temperature of 175±5°and pressure of 70-100 kg/cm2. The ratio of the stabilizer and HDPE and the original properties of the stabilized HDPE are shown in table 3.

Table 3
# exampleGOST 16338-8516 (control)18
1234
Put the stabilizerWithout stabilizerThe stabilizer of the formula (I)
The amount of stabilizer, wt.%00,1
HDPE 276-73100

Continuation of table 3
Initial physical-mechanical indicator
1234
The melt flow index at a load of 5 kg (g/10 min)2,6-3,22,82,7
Strength at break (MPa), not less than27,428,629,0
Yield strength tensile (MPa), not less than25,526,827,4
Elongation at break (%), min.700860920
Color(visually)-NaturalNatural

Determination of resistance to thermal-oxidative aging of samples of HDPE 276-73 obtained in examples 16, 17, implement the following methods:

1. By determining the change of the melt flow index (MFR) after exposure of samples HDPE 276-73 obtained in examples 16-18, the channel extrusion plastometer for 2 hours at a temperature of 190°under a load of 5 kg (table 4).

Table 4
# exampleThe composition of the sample PTR5, g/10 minThe change in VKT5, %
Ex.2 hours
16 (control)HDPE 276-73 without stabilizer2,82,318
17Composition HDPE 276-73 with a stabilizer of the formula (I) (0.1 wt.%)2,72,57

2. By determining the changes in rheological properties (bell method) and color when demostation samples HDPE 276-73 obtained in examples 16, 17, at a temperature of 175°in the air on an aluminum substrate within 8 hours, with intermediate removal of samples after 4 hours (table 5).

Table 5
# exampleThe composition of the sampleMFR, g/10 minChange the TPP, % over 8 hoursColor change (visually)
ex.4 hours8 hours
16 (control)HDPE 276-732,810,4to 12.0329Yellow spot
17Composition PEND-73 with a stabilizer of the formula (I) (0.1 wt.%)2,72,5,4 11No.

3. By determining the induction period of oxidation of HDPE samples 276-73 obtained in examples 16, 17, at a temperature of 200°C in an atmosphere of oxygen (PO2=250 mm Hg) (table 6). The induction period of oxidation of the polymer is determined in accordance with the method [see Piotrovsky K.B., Tarasova Z. Aging and stabilization of synthetic rubbers and vulcanizers. - M.: Chemistry, 1980. - 264 S.].

Table 6
# exampleThe composition of the sampleThe induction period of oxidation, min
16 (control)HDPE 276-7310
17Composition HDPE 276-73 with a stabilizer of the formula (I) (0.1 wt.%)100

4. By examining the changes in the properties of samples of HDPE 276-73 obtained in examples 16, 17, during long-term thermo-oxidative ageing at a temperature of 110°C for 1000 hours (table 7): strength at break δpyield strength tensile δt; relative elongation at break ε; melt flow index (MFR); color change. First release samples to determine changes of properties in the aging process was performed after 100 hours exposure, the trail is the following releases were made through 300, 700 and 1000 hours.

Determination of physico-mechanical properties of polyethylene with a stabilizer (tensile strength δpyield strength tensile δt, elongation at break ε carried out in accordance with GOST 11262-80 on samples of type 1 with a thickness of 1±0.1 mm in a tensile testing machine for testing plastics brand 2166 R-5 at a temperature of 20±3°and the moving speed of the rolling clamp bursting machine 50±5 mm/min For the test result arithmetic mean value of physical-mechanical indicators of the five samples.

The melt flow index (MFR) determined according to GOST 11645-73 on extrusion plastometer with a nozzle diameter of 2.09 mm (standard nozzle) at a temperature of 190±5°and a load of 5 kg after exposure of the material in the heated device for 4 minutes.

Table 7
# exampleThe composition of the sampleThe time of incubation, hIndex
ε, %δpδtMFR, g/10 minColor
16 (Control)HDPE 276-73086028,6 26,82,8Genuine cowhide leather-makes.
10053016,814,52,4Genuine cowhide leather-makes.
30048015,714,61,9Genuine cowhide leather-makes.
70027016,312,51,5Yellow spot
100030013,912,81,3Yellow spot
17Composition HDPE 276-73 with a stabilizer of the formula (I) (0.1 wt.%)092028,027,42,7Genuine cowhide leather-makes.
10090027,427,02,6Genuine cowhide leather-makes.
30085026,826,32,6Genuine cowhide leather-makes.
70067026,625,82,4Genuine cowhide leather-makes.
100059026,025,52,4Genuine cowhide leather-makes.

As can be seen from tables 4-7, the inventive stabilizer (I) has the property to slow down the aging of polyolefin HDPE preserving natural color polyolef is on. The stabilizer of the formula (I) is well combined with the polyolefin.

Examples 18, 19.

The introduction of stabilizers in polyolefin polypropylene (PP).

A portion of the polyolefin PP and stabilizer are rolling (length rolls 260 mm, roll diameter 100 mm, the speed of rotation of the rolls 28 rpm, time, rolling 5±1 min). The composition of the Board samples obtained in examples 18, 19 are shown in table 8.

Table 8
# example1819
StabilizerThe stabilizer of the formula (I) (0.2 wt.%)The stabilizer of the formula (I) (0.2 wt.%)
Calcium stearate0,10,05
PP-21030100

Determination of resistance of polyolefin PP to thermal-oxidative ageing carried out by the following methods criteria:

1) by measuring the melt flow index (MFR) and yellowness index during multiple extrusion. The TPP is determined on extrusion plastometer at a temperature of 230±5°and a load of 2.16 kg after exposure of the material in the heated device for 4 minutes (table 9)

2) by determining the time to failure of the sample in air at 150°With (CBT). Testing TOC samples made method is m injection molding. For tests using samples 50×15×1 mm, which is placed in a heat chamber at 150°C. the Results are given in table 9.

Table 9
# example19
Stabilizer (wt.%)Composition 1111-21030 with a stabilizer of the formula (I) (0.2 wt.%)
The results of the tests
PTR5, g/10 min
ex.2,5
The multiplicity of extrusion:
13,6
36,2
57,0
The yellowness index
The multiplicity of extrusion:
13,5
36,1
59,0
CBT, h
>360

3) the Change of physico-mechanical properties after thermostate (135°C, 7 days). Samples for the determination of physico-mechanical properties are prepared by casting under pressure, after which their condition at 23°C for 24 hours. Termostate samples performed within 7 days at T=135°C. the results of the IP is itani are given in table 10.

Table 10
# example19
The composition of the sampleComposition PP-21030 with a stabilizer of the formula (I) (0.2 wt.%)
The results of physico-mechanical tests
After conditioning (23°C, 24 h)After thermostate (135°C, 7 days)
Yield strength tensile (MPa)35,433,2
Relates. elongation at yield, %16,828,6
Ultimate tensile strength, MPa44,634,2
Relates. elongation at break, MPa348,088,0
The modulus of tensile elasticity859,0561,0

The findings suggest that the polyolefin polypropylene containing a stabilizer of the formula (I) in an amount of 0.2 wt.% is thermostable, the stabilizer of the formula (I) provides svetostoyjkostj polymer.

Examples 20, 21.

Stability of synthetic ethylene-propylene rubber (Sept) determine elaut on the following criteria:

1) for the duration of the induction period of oxidation of the polymer (pO2=250 mm Hg, T=165-170°C

2) by the change in Mooney viscosity in terms of thermo-mechanical treatment by passing through an extruder 1,2 min 220°C.

The stabilizer content in the sample and the results are given in table 11.

Table 11
# example20 (control)21
The composition of the sampleSept-40The composition of Sept-40 with a stabilizer of the formula (I) (0.2 wt.%)
The results of the tests
The Indus. the period of oxidation160170
The Mooney viscosity of the rubber to the extrusion4242
The Mooney viscosity of the rubber after extrusion4142

Examples 22, 23.

The stability of butyl rubber (BK) is determined according to the following criteria:

1) for the duration of the induction period of oxidation of the polymer (pO2=250 mm Hg, T=165-170°C

2) by the change in Mooney viscosity in terms of thermo-mechanical treatment by passing through an extruder 1,2 min 220°C.

The stabilizer content in the sample and the test results Pref is found in table 12.

Table 12
# example22 (control)23
The composition of the sampleBq-1675Composition BK-1675 with a stabilizer of the formula (I), (0,2 wt.%)
The results of the tests0,2
100
The results of the tests
The Indus. the period of oxidation260270
The Mooney viscosity of the rubber to the extrusion7474
The Mooney viscosity of the rubber after extrusion5273

Thus, the inventive method allows to simplify the process by reducing the number of operations and to obtain 2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)cyclohexane-1-he yields up to 86%.

The method of obtaining 2,6-di(3,3',5,5'-di-tert-butyl-4,4'-oxybenzyl)-cyclohexane-1-she by reacting cyclohexanone with Basilisk reagent, followed by separation of the target product, characterized in that as benzylurea reagent take the N,N-dimethyl-(3,5-di-tert-butyl-4-oxybenzyl)amine in a ratio of cyclohexanone and N,N-dimethyl-(3,5-di-tert-butyl-4-oxybenzyl)amine (1÷1,2:2, respectively, and the process is conducted at a temperature of 125-145° To stop shedding dimethylamine.



 

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