SU925940A1 - Process for preparing protein food jellies - Google Patents

Description

(5) METHOD FOR OBTAINING L-SUBSTITUTED UREAS WITH END HYDROXYL GROUPS

I

The invention relates to an improved process for the preparation of substituted hydroxyl terminated ureas, which can be used as starting components in the production of polyurethanes, for example, as a chain extender and structuring agent.

A known method for the preparation of a urea-containing compound with terminal HYDROXYL groups by reacting carbon monoxide sulfide COS in a mixture with other gases, such as Ng, CDg, CO, Nd, Alc with primary aliphatic amines 111.

However, the known method has technological difficulties associated with the use of toxic raw materials COS, carbon dioxide CO. fire and explosion hazardous SND, with instrumentation requiring a tight supply of a mixture of toxic gases, bubbling gases through the solution.

with the use of toxic and flammable solvents, with the need for pre-cleaning, drying and subsequent removal of solvents. In addition, the reaction by this method is the release of hydrogen sulfide HgS, known for its high toxicity.

A method of obtaining urea-containing compounds by the reaction

10 alkylamines with ureas in aqueous or acetic acid solutions 2.

However, the urea-containing compounds obtained in a known manner cannot be used in the production of polyurethane materials either as a chain extender or as a structure-forming agent, since they do not have terminal functional groups. In that case,

30 when urea with terminal HYDROXYL groups is prepared, then under the conditions of synthesis of the known method they can hardly be extracted. The method has significant technological difficulties associated with the use of solvents and with the release of a side gas of W. There is also known a method for producing N-substituted Urea with terminal hydroxyl groups, which can be used as precursors in the production of polyurethanes, for example as a chain extender and structuring agent. This method carried out by reacting diisocyanates with amino alcohol D1. However, diisocyanates are highly toxic, their high reactivity, including with respect to atmospheric moisture, as well as their high cost, are the main aspects hindering the wide application of this method. The closest to the invention to the technical essence and the achieved result is a method of producing N-substituted urea with one terminal hydroxyl group by reacting urethane-containing compounds with amino alcohols, namely N-phenylbenzyl-carbamates of the general formula NH-O - OCH3 O substituted in the ring methyl, methane, chloro, and nitro groups in the ortho, meta, and para positions, with monoethanolamine in a solution of benzyl alcohol in the temperature range of 130-170 ° C. However, N-substituted urea with one hydroxyl group, obtained by this method, cannot be used either as a chain extender or as a structure-forming agent in the synthesis of polyurethane materials. This is due to the fact that, having one hydroxyl group in its composition and interacting with the prepolymer NCO group, it breaks the chain, i.e. It has an effect completely opposite to the extension of the chain. In addition, this method has a number of significant technological drawbacks associated with the use of toxic and fire-cleaning solvents If drying and subsequent distillation to isolate the target product. The aim of the invention is to simplify the process and expand the range of target products. The goal is achieved by the fact that according to the method of obtaining -substituted ureas with terminal hydroxyl groups by reacting urethane-containing compounds with amino alcohols, when heated, urethane glycols are used as urethane-containing compounds and the process is carried out / at a temperature of 80-T20 ° C. As urethane-containing glycols, diurethane glycols of the formula RRR are used predominantly, where B- is the safe (cis), g tte is with at the 2nd, xCHCh- - (G-TI (, N-CCHa-CHj- and // -C-NH-dflg c., O R- // J7u-OCgHgOH. Urethane-containing glycols can also be used as monourethane glycols of the general formula with terminal hydroxyl groups in a fairly simple instrumentation. The absence of solvents eliminates the risk of fire and reduces toxic as well as simplifies the technology, since there are no operations such as pre-cleaning and drying of solvents and subsequent removal to isolate the target product. During the reaction no toxic side products are formed, and the distilled excess amine can be used in recycling. S, 3 g of urethane glycol, having the formula, is loaded into a reactor equipped with a thermometer, a stirrer and a vacuum bead. . HE — CrH4-o — with —NH — with rH-t- it — about the reaction temperature, supported by the supply of the Vaseline TH fluid coolant to the oil in the jacket of the reactor, is set, and 19 tg of monoethanolamine is added with stirring, i.e. 0 mole The reaction is monitored by the disappearance of amino groups by direct titration of the reaction mixture in an aqueous solution of 0.1 n. with a solution of HC1 in the presence of an indicator of the brpmcresol green indicator. Upon reaching the conversion in the ur tan group, the excess monoethanolamine is distilled off at 5 mm Hg and OST. to a residual concentration of mon ethanolamine in a mixture of 1,. 0 mol / kg. The resulting product is washed with chloroform and recrystallized. The yield of the product is 87%, composition, Oj so pl. 85 ° C. Elementary composition: ОН- CaH -NH-C-NH-CsjH pOH О Calculated,%: C 40.5; H 8.1; N 18.9v O 32. Found,%: kl; H 8.05; N 18.6-, O 32.3., Formula of the obtained N, N-dihydroxyethyl urea OHCgHiNH-C-BH-O Example 2. The experiment was carried out according to the procedure described in Example 1. To 5.3 g of urethane glycol having Formula OH-CzH-O-C-NH-OaH4-OH O is added 23.57 g of diethanolamine. Product yield 82%. Composition so pl. 90 ° C.

The elementary composition :, Calculated,%: C, 8; H 8,

Tt, 6; About 33.3 ... -

Found,%: C 43.5. H 8I; N Il, 9;

33.5. ..

70 g monoethanolamine are added.

The product yield 75%, so pl.

Elementary composition.

Calculated,%: C, 7, - H 6.86; N 10.75; About 36.7. The formula for the resulting N, N, N -trihydroxy istilurea: OH-CgH-i. No-C-Sh-OgH4-OH OH-Cg1C O Example 3. The experiment was carried out according to the procedure described in Example 1. To 5.6 g of urethane glycol HOdjHeO - C-INSaH OH O was added 23.6 g of diethanolamine. Product yield 85%. Elementary composition. . Calculated D: C, 8; H V. 1.6J ° 33.3. Found,%: C, 5; H 8.1; N}, E; - tx, g, Formula of the obtained N, N, N -trihydroxyethyl urea. OHCgH x N-O-NHCjH OH OHC2H4 / o Example. The experiment was conducted as in Example 1. To 1.92 g of urethane glycol having the formula HOC2H40C-NHlCH2) 6-NH-C-OC2H OH OH, 126 g of diethanolamine was added. Product yield 87%. Elementary composition.i Calculated,%: C 52.2; N 15.3; 6.52., O 26. Found,%: C 50.8; N 15.2; I. 7.15; 26.8. The formula of the obtained N, N, N, N -thetagidroxyethyl (hexamethylene) -dimerochiny: oSgN4) 2N-o-1 "n- (cNg) in - - {-G rN40N) 2 o Example 5. The experiment is carried out according to the method described in example 1. To 6.6 g of urethane glycol having the formula -dHjCHjx HOCoH OC-N .NC-OCgH OH CHjCMf

Claims (1)

Claim 1. The method of obtaining N-substituted urea with terminal hydroxyl R- -OS ₂ H ₄ OH IM -OS ^ H _b O ". The method of pop. 1, characterized in that as urethaglycols use monourethaglycols of the general formula o, ⁿ K — C —NHCgH ₄ OH where R ′ is as defined.