Trimethylolpropane (referred to as TMP) chemical name is 2-ethyl-2-hydroxymethyl-1,3-propanediol, likewise called trimethylolpropane, 2,2-dimethylol butanol, its molecule has 3 normal hydroxymethyl teams, so they have polyol buildings similar to glycerol,and also react with diisocyanates to create carbamates Esters, etc, are widely utilized chemical basic materials and also chemical products, primarily used in alkyd resins, polyurethanes, unsaturated resins, polyester materials, coatings and various other fields, and also can also be utilized in the synthesis of air travel lubricating substances, plasticizers, surface area energetic It can additionally be directly used as textile accessories and heat stabilizers for PVC resins. Trihydroxymethylpropane is slightly toxic to mice and low toxicity to Japanese medaka embryos. In the production process of paper, including cigarette lining paper, tipping paper, box wrapping paper, etc., various chemicals such as bleaching agents, processing aids, printing inks, antiseptics and bactericides need to be added to prevent the production of paper. Improve its packaging performance and aesthetics. However, studies have found that these chemicals, including 1,1,1-trihydroxymethylpropane, can remain in paper and migrate into cigarettes, some of which are toxic and even carcinogenic, posing a health hazard to consumers. The United States, the European Union, Japan and other developed countries have formulated corresponding regulations and limited standards for packaging materials that come into contact with food, and implemented strict market access management.
Trimethylolpropane Properties:
Melting point
56-58 °C(lit.)
Boiling point
159-161 °C2 mm Hg(lit.)
density
1.176
vapor density
4.8 (vs air)
vapor pressure
<1 mm Hg ( 20 °C)
refractive index
1.4850 (estimate)
Fp
172 °C
storage temp.
Store below +30°C.
solubility
H2O: 0.1 g/mL, clear
pka
14.01±0.10(Predicted)
form
Flakes
color
White
PH
6.5 (100g/l, H2O, 20℃)(External MSDS)
explosive limit
2-11.8%(V)
Water Solubility
soluble
Trimethylolpropane Uses
Trimethylolpropane is used as a glycerin substitute and also in the synthesis of drying oils.
Trimethylolpropane is extensively used in polyester as well as polyurethane foam production, along with in the manufacture of alkyd finishings, synthetic lubricating substances, plasticizers, surfactants, rosin esters and also dynamites. It is also straight utilized as a fabric auxiliaries and also thermal stablizing of PVC resins, as well as can be utilized in alkyd materials to boost the firmness, shade tone, climate resistance, chemical resistance, and sealing residential or commercial properties of the resin.
Trimethylolpropane is scheduled to be used in the manufacture of composite solid propellant charge coating layers and thermal insulation layers, as well as resin modifiers and cross-linking agents.
Trimethylolpropane contains three hydroxymethyl groups on the A-position of the molecule, and is a trivalent alcohol with a neopentyl structure. It can improve the firmness, corrosion resistance and sealing performance of the resin; it has good stability to hydrolysis, pyrolysis and oxidation; the three hydroxyl groups have excellent properties such as the same reaction.
Preparation Method of Trimethylolpropane
1. Cross Canizaro condensation method Cross Canizaro condensation method is also known as sodium formate method. Aldol condensation reaction between n-butyraldehyde and formaldehyde solution under the action of alkaline catalyst to generate 2,2-dimethylolbutyraldehyde, 2,2-dimethylolbutyraldehyde then reacts with excess formaldehyde under strong alkali conditions Cross-Connizzaro reaction generates trimethylolpropane, formaldehyde is oxidized to generate formic acid, formic acid is neutralized with sodium hydroxide to generate sodium formate, and the reaction mixture is desalted and refined to obtain qualified products. The relevant reaction equation is:
Fig. 1 is the reaction equation that crosses Cannizzaro condensation method to synthesize TMP When adopting this method to produce trimethylolpropane, the used catalyst mainly contains sodium hydroxide, calcium hydroxide, calcium oxide and organic tertiary amines (such as trimethylamine, triethylamine, etc.) etc. When using sodium hydroxide as a catalyst, because it is soluble in water, the process difficulty increases when the sodium formate is finally removed, so the catalyst has been eliminated abroad; using an organic tertiary amine as a catalyst, the separation is easier, but the catalyst is expensive. As a result, the production cost of trimethylolpropane increases; calcium hydroxide (or calcium oxide) can be precipitated due to its low solubility in water, and the rest can be separated by centrifugal separation and membrane separation. Calcium can be directly used in feed additives, preservatives, etc. At present, most of the foreign trimethylolpropane is produced by this catalyst. Cross-Canizaro condensation method is a traditional method for producing trimethylolpropane. However, this method has many by-products, poor product quality, and large post-processing workload, and the product yield is only 60% to 70%. In order to reduce the formation of by-products, a large excess of formaldehyde (generally 8 to 10:1 molar ratio) is required to facilitate the completion of the reaction and to suppress the formation of some difficult-to-separate heat-sensitive substances, but a large excess of formaldehyde increases the load of the post-processing dealdehyde tower , the energy consumption increases. In addition, the post-treatment of this process is cumbersome, and 1 t of sodium formate with very low added value is by-produced for every 1 t of trimethylolpropane, resulting in a very low utilization rate of formaldehyde, an increase in production costs, and difficulty in refining trimethylolpropane. , How to effectively remove formate is the key to the preparation of high-quality trimethylolpropane. 2. Aldehyde hydrogenation reduction method n-butanol reacts with formaldehyde under the catalysis of trialkylamine (such as triethylamine) to obtain 2,2-dimethylol butyraldehyde, the aldol condensation product, and then in the presence of a catalyst, to 2,2-Dimethylolbutyraldehyde is hydrogenated to produce trimethylolpropane. The relevant reaction equation is:
Figure 2 shows the reaction equation for synthesizing TMP by the aldehyde hydrogenation reduction method. During the aldol condensation, triethylamine is mainly used as the catalyst, and triethylamine is used as the catalyst for the aldol condensation reaction, which can control the selectivity of the reaction and suppress the side effects of The occurrence of the reaction reduces the formation of formate. The aqueous hydrogenation catalyst is mainly nickel or nickel oxide distributed on the carrier, and copper chromite can also be used, and copper oxide or copper-chromium is used as a cocatalyst. The aldehyde hydrogenation reduction method has high formaldehyde utilization rate, strong hydrogenation technology, can save a lot of formaldehyde and alkali, relatively few side reaction products, good product quality, simple purification and purification, less equipment, and low production cost, but it needs to add The hydrogen unit adopts high-pressure equipment, which has high requirements on hydrogenation equipment and catalysts, as well as high production technology requirements, and is more suitable for large-scale continuous production. At present, some trimethylolpropane manufacturers in Europe and the United States mainly use this method for production.
Trimethylolpropane Determination
The method for the determination of trimethylolpropane, firstly cut the cigarette paper into pieces, add ultrapure water, then ultrasonically extract, centrifuge the extract, and directly measure the trimethylolpropane in the paper by liquid chromatography-tandem mass spectrometry, specifically Include the following steps:
a. Weigh 1.0g of the sample (accurate to 0.01g) and place it in a 50mL conical flask with a stopper.
b. Extraction of samples: Accurately add 20 mL of extract: ultrapure water, and ultrasonically extract for 30 minutes; optimization of extract: We have added methanol, acetonitrile and water to the positive samples for ultrasonic extraction for 30 minutes and then centrifugal filtration. The extraction effect of different solvents on 1,1,1-trihydroxymethylpropane in cigarette paper is almost the same, and the average recovery rate is above 85%. However, both methanol and acetonitrile have certain toxicity, and the chromatographic peaks are not symmetrical. Therefore, considering the selection of ultrapure water as the extraction solvent.
c. Sample purification: stand for 5 minutes, pipette 8 mL of the extract into a 10 mL centrifuge tube, and centrifuge at 5000 rpm for 10 minutes. The supernatant was aspirated and filtered through a 0.22 μm organic filter.
d. Pipette 100 μL of the filtrate, dilute the sample to 1.0 mL with ultrapure water, and use it as the sample to be tested for LC-MS/MS analysis;
e. Prepare standard working solution: Weigh 0.01g of 1,1,1-trimethylolpropane standard into a 10mL volumetric flask, dilute with ultrapure water and finally prepare a standard working solution with a concentration gradient;
f. Determination of liquid chromatography-tandem mass spectrometry: draw the prepared standard working solutions of different concentrations and the sample liquid to be tested, and inject them into the liquid chromatography-tandem mass spectrometer respectively;
g, 1,1,1-Trimethylolpropane determination result calculation
Quantitative analysis was carried out by the external standard method, that is, the peak area of the quantitative ion pair of trimethylolpropane was used to perform regression analysis on its corresponding concentration to obtain a standard curve, and the correlation coefficient was greater than or equal to 0.999. The extracted sample liquid to be tested is measured, the peak area of the quantitative ion pair of trimethylolpropane is detected, and the residual amount of trimethylolpropane in the sample is obtained by substituting it into the standard curve.
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