77-99-6

Basic information

• Product Name: Trimethylolpropane
• Synonyms: NSC 3576;Propane,1,1,1-tris(hydroxymethyl)-;RC Crosslinker TR;TMP;TMP (alcohol);Hexaglycerine;Tris(hydroxymethyl)propane;Trimethylol Propane (TMP);1,1,1-Tri(hydroxymethyl)propane;1,1,1-Trimethylolpropane;1,1,1-Tris(hydroxymethyl)propane;2,2-Bis(hydroxymethyl)-1-butanol;2-Ethyl-2-(hydroxymethyl)-1,3-propanediol;2-Ethyl-2-(hydroxymethyl)propanediol;Addolink TR;Ethriol;Ethyltrimethylolmethane;Ettriol
• CAS NO: 77-99-6
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.17356
• EINECS: 201-074-9
• Mol File: 77-99-6.mol

Chemical Properties

• Melting Point: 56-60℃
• Boiling Point: 295.7 °C at 760 mmHg
• Flash Point: 147.7 °C
• Appearance: white crystalline flakes
• Density: 1.116 g/cm³
• Vapor Pressure: 0.000155mmHg at 25°C
• Refractive Index: 1.484
• PKA: 14.01±0.10(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: Trimethylolpropane(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylolpropane(77-99-6)
• EPA Substance Registry System: Trimethylolpropane(77-99-6)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 77-99-6(Hazardous Substances Data)

Usage

Uses

Used in Synthetic Lubricants:
Trimethylolpropane is used as a building block for synthetic lubricants, contributing to their combat against oxidation. Its stability properties make it an ideal component in the formulation of lubricants that require resistance to temperature extremes.
Used in Alkyd Resins for Coating Materials:
In the coatings industry, Trimethylolpropane is used as a component in alkyd resins, which are essential for the production of various types of coatings. Its inclusion in these resins enhances the overall performance and durability of the coatings, making them suitable for a wide range of applications.

InChI:InChI=1/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3

Synthetic route

formaldehyd (50-00-0) + butyraldehyde (123-72-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With water; sodium hydroxide In ethanol at 55℃; for 0.0833333h; Temperature;	90%
With calcium hydroxide
With sodium hydroxide In water at 40 - 60℃; for 0.75h;

butyraldehyde (123-72-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With sodium hydroxide; formaldehyd; triethylamine; Ni-Cr-Al	88.5%
With formaldehyd; triethylamine In water	82.77%
With formaldehyd; triethylamine In water	81.59%

2,2-dimethylolbutanal (41966-25-0) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With hydrogen at 115℃; under 22502.3 Torr; for 8h;	84.8%
With hydrogen; Cu/TiO2 catalyst B of PCT/WO 02/85825; activated at 110℃; under 67506.8 Torr; for 2112h; Conversion of starting material;
With hydrogen; citric acid; activated Cu/TiO2 catalyst J PCT/WO 99/44974 In water at 120℃; under 60006 Torr; Conversion of starting material;
With hydrogen at 120℃; under 22502.3 Torr;

copper-II acetate + tris-methylamino-borane (7397-44-6) + butyraldehyde (123-72-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With triethylamine In methanol; formaldehyd	74.6%

ethylacrolein (922-63-4) + formaldehyd (50-00-0) → bis-TMP + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3,3,7,7-tetra(hydroxymethyl)-5-oxanonane (23235-61-2)

Conditions	Yield
In water at 96 - 100℃; for 3.3h;	A 2% B 67.5% C 15%

nickel(II) oxide (1313-99-1) + Al2 O3 + butyraldehyde (123-72-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With formaldehyd; triethylamine	14%

2-hydroxymethyl-2-vinyl-propane-1,3-diol (103205-80-7) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

2,2-bis(hydroxymethyl)-1,4-butanediol (95461-66-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium acetate 2: 500 °C 3: barium methylate; methanol 4: palladium/charcoal; ethanol / Hydrogenation View Scheme

4-acetoxy-3,3-bis-acetoxymethyl-but-1-ene (105790-11-2) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: barium methylate; methanol 2: palladium/charcoal; ethanol / Hydrogenation View Scheme

1,4-diacetoxy-2,2-bis-acetoxymethyl-butane → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 500 °C 2: barium methylate; methanol 3: palladium/charcoal; ethanol / Hydrogenation View Scheme

formaldehyd (50-00-0) + butyraldehyde (123-72-8) → bis-TMP + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3,3,7,7-tetra(hydroxymethyl)-5-oxanonane (23235-61-2)

Reaxys ID: 11464418 → 1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3,3,7,7-tetra(hydroxymethyl)-5-oxanonane (23235-61-2) + 5-ethyl-1,3-dioxane-5-methanol (5187-23-5)

Conditions	Yield
With toluene-4-sulfonic acid In water at 90℃; for 6h;	A n/a B 5.9 g C n/a
With toluene-4-sulfonic acid In water at 90℃; for 6h;	A n/a B 15.2 g C n/a

crude TMP → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
Stage #1: crude TMP With phosphoric acid at 150℃; under 50 Torr; for 1h; Stage #2: With phosphoric acid at 180℃; for 1h;

2,2-dimethylolbutanal (41966-25-0) → methanol (67-56-1) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + trimethylamine-formic acid complex (58828-90-3)

Conditions	Yield
With hydrogen In water at 115℃; under 67506.8 Torr;

piperidine (110-89-4) + N-Formylpiperidine (2591-86-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

succinic acid anhydride (108-30-5) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With pyridine In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane

formaldehyd (50-00-0) + 2,2-dimethylolbutanal (41966-25-0) → 1,1,1-tri(hydroxymethyl)propane (77-99-6) + sodium formate (141-53-7)

Conditions	Yield
With sodium hydroxide In water at 45 - 50℃; for 3.75 - 4.25h; Product distribution / selectivity; Cannizzaro Reaction;

formaldehyd (50-00-0) + butyraldehyde (123-72-8) → ethylacrolein (922-63-4) + 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With water; sodium carbonate at 73 - 84℃; Product distribution / selectivity;
With sodium carbonate In water Reagent/catalyst; Temperature; Concentration; Reflux;	A 58 g B 15 g

ethylacrolein (922-63-4) + formaldehyd (50-00-0) → 1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3,3,7,7-tetra(hydroxymethyl)-5-oxanonane (23235-61-2)

Conditions	Yield
Stage #1: ethylacrolein; formaldehyd In water at 100℃; Stage #2: With sodium hydroxide In water at 100℃; Reagent/catalyst; Time; Concentration;	A 253 g B 66 g

C6H11O3(3-)*Sb(3+) → 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With water-d2 In dimethylsulfoxide-d6 Glovebox;

formaldehyd (50-00-0) + butyraldehyde (123-72-8) → 1,1,1-tri(hydroxymethyl)propane (77-99-6) + 2,2-dimethylolbutanal (41966-25-0)

Conditions	Yield
With triethylamine at 35℃; for 3h; Cannizzaro Reaction;

formaldehyd (50-00-0) + butyraldehyde (123-72-8) → methanol (67-56-1) + 1,1,1-tri(hydroxymethyl)propane (77-99-6)

Conditions	Yield
With potassium hydroxide In water at 60℃; for 1h; Temperature; Cannizzaro Reaction;	A 11.71 %Chromat. B 76.63 %Chromat.

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3-chloroprop-1-ene (107-05-1) → trimethylolpropane triallyl ether (682-08-6)

Conditions	Yield
With sodium hydroxide; sodium chloride; tetrabutylammomium bromide In toluene	100%
With sodium hydroxide; tetrabutylammomium bromide 1.) water, 80 deg C, 0.5 h, 2.) 80 deg C, 7 h; Yield given. Multistep reaction;
With sodium hydroxide; tetrabutylammomium bromide In water at 45℃; for 22h; Allylation;
With tetrabutylammomium bromide; sodium hydroxide at 45℃; for 22h;

2-bromophenylacetic acid (4870-65-9) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) → Bromo-phenyl-acetic acid 2,2-bis-(2-bromo-2-phenyl-acetoxymethyl)-butyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃;	100%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + oxiranyl-methanol (556-52-5) → C72H107N3O34

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane With potassium tert-butylate In tetrahydrofuran at 120℃; for 18h; Inert atmosphere; Stage #2: oxiranyl-methanol In tetrahydrofuran at 120℃; for 0.5h; Inert atmosphere; Stage #3: 2-oxiranylmethylisoindole-1,3-dione In tetrahydrofuran at 120℃; Inert atmosphere;	100%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + vinyl glycolic acid (600-17-9) → C18H26O9

Conditions	Yield
With salicylaldehyde In toluene at 100℃; for 14h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	100%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + salicylaldehyde (90-02-8) → 2-[(5-ethyl-5-hydroxymethyl)-1,3-dioxan-2-yl]phenol (22251-64-5)

Conditions	Yield
With sulfuric acid at 80℃;	100%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + Diethyl carbonate (105-58-8) → trimethylolpropane cyclic monocarbonate + C9H18O5 (1286272-49-8)

Conditions	Yield
With Novozym435 at 60℃; for 48h; Molecular sieve; Enzymatic reaction; neat (no solvent);	A 6% B 99.4%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + acetone (67-64-1) → 1,3-dioxa-5-ethyl-2,2-dimethyl-5-cyclohexylmethanol (20761-68-6)

Conditions	Yield
With toluene-4-sulfonic acid In water; Petroleum ether for 10h; Reflux;	99%
With toluene-4-sulfonic acid at 20℃; for 16h;	78%
With toluene-4-sulfonic acid In Petroleum ether Heating;	76%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 4-Phenylbutyric acid (1821-12-1) → 1,1,1-tri(4-phenylbutyroxymethyl)propane

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 24h; Heating;	99%
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 24h;	99%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + tributyltin methoxide (1067-52-3) → 1,1,1-tris(tributyltinoxymethyl) propane (79428-57-2)

Conditions	Yield
In neat (no solvent) 1,1,1-trymethylolpropane to methoxytributyltin ratio 1:3; mixed, heatedat 100-150°C for 1 h at P=50 mm; evacuated to P=1 mm for 0.5 h, heated at 190-220°C; distd., IR, elem. anal.;	99%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + C27H43N3O13 → C87H137N9O39

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; acetonitrile at 20℃;	99%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + acryloyl chloride (814-68-6) → 2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate (15625-89-5)

Conditions	Yield
With 4-methoxy-phenol; triethylamine; hydroquinone at 60℃; for 2h; Temperature;	98.38%
In pyridine; benzene at 50℃; for 30h;	81%
With pyridine In benzene at 50℃; for 30h;	81%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 1,4-Cyclohexanedione (637-88-7) → C18H32O6

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 90 - 112℃; for 10h; Reagent/catalyst; Solvent; Dean-Stark;	98%

formaldehyd (50-00-0) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) → 5-ethyl-1,3-dioxane-5-methanol (5187-23-5)

Conditions	Yield
With cationite KU-2 In benzene Reflux; Dean-Stark;	97%
With toluene-4-sulfonic acid In toluene for 4h; Heating;	95%
With toluene-4-sulfonic acid In toluene for 4h; Heating;	95%
With toluene-4-sulfonic acid In tetrahydrofuran for 3h; Reflux;	93%
With toluene-4-sulfonic acid

1,1,1-tri(hydroxymethyl)propane (77-99-6) + isooctanoic acid (929-10-2) → C30H56O6

Conditions	Yield
With chlorosulfonic acid; 3,5-dichloro-2-hydroxybenzenesulfonyl chloride; 3-methylimidazoletrifluoromethanesulfonate; toluene-4-sulfonic acid In tetrahydrofuran; propan-1-ol at 200℃; for 10h; Temperature; Large scale;	97%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + p-toluenesulfonyl chloride (98-59-9) → C20H26O7S2 + 2-ethyl-2-((tosyloxy)methyl)propane-1,3-diyl bis(4-methylbenzenesulfonate) (6962-93-2)

Conditions	Yield
With pyridine at -5 - 20℃; for 48h;	A n/a B 96.5%

1,10-decanedioic acid (111-20-6) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + hydrogenated castor oil → polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

Conditions	Yield
With dibutyltin(II) dilaurate at 180 - 200℃;	96.4%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → tris((trimethylsiloxy)methyl)propane (17940-81-7)

Conditions	Yield
With activated clay at 60 - 70℃; for 3h;	96.4%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 4-(1,3-diacetoxypropan-2-yloxy)-4-oxobutanoic acid → C39H56O24

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; for 24.5h;	96%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + ethyl chlorocarbonylacetate (36239-09-5) → O,O'-(2-(((3-ethoxy-3-oxopropanoyl)oxy)methyl)-2-ethylpropane-1,3-diyl) diethyl dimalonate

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; for 12h;	96%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + phosphorous acid trimethyl ester (121-45-9) → dimethyl methane phosphonate (756-79-6)

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; phosphorous acid trimethyl ester at 80 - 120℃; for 4h; Stage #2: With methyl p-toluene sulfonate at 170 - 180℃; for 2h; Reagent/catalyst; Temperature;	96%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + Dipentaerythritol (126-58-9) + dimethyl methane phosphonate (756-79-6) + phosphorous acid trimethyl ester (121-45-9) → methyl-(5-ethyl-2-methyl-1,3,2-dioxaphosphorinan-5-yl)methyl methyl ester (P-oxide phosphonate)

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; Dipentaerythritol; phosphorous acid trimethyl ester With phosphoric acid at 85℃; for 5h; Inert atmosphere; Stage #2: dimethyl methane phosphonate With 1-bromo-butane at 185℃; for 16h;	95.8%

trimethyl phosphite (512-56-1) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + tri-n-butyl phosphite (102-85-2) + Dipentaerythritol (126-58-9) → C13H25O10P3

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; tri-n-butyl phosphite; Dipentaerythritol With sulfuric acid at 85℃; for 5h; Inert atmosphere; Stage #2: trimethyl phosphite With 1-Bromopentane at 185℃; for 16h;	95.6%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + bromoacetic acid (79-08-3) → C12H17Br3O6 (343846-05-9)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; toluene-4-sulfonic acid In toluene for 7h; Reflux;	95.1%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + C32H50O15S4 → TMP-(S-S)3-G1-(acet)3

Conditions	Yield
With pyridine; dmap In dichloromethane at 0℃;	95.1%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + perfluoroisobutylene (382-21-8) → 1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (382-24-1) + 2-hexafluoroisopropylidene-5-ethyl-5--1,3-dioxane (97651-62-2)

Conditions	Yield
With potassium fluoride In acetonitrile 1) 0 deg C, 1 hour 2) 20 deg C, 11-12 h;	A n/a B 95%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + acrylic acid (79-10-7) → 2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate (15625-89-5)

Conditions	Yield
With methanesulfonic acid; hypophosphorous acid; hydroquinone In cyclohexane at 70 - 91℃; under 3750.38 Torr;	95%
Stage #1: With hypophosphorous acid; 4-methoxy-phenol; copper dichloride In cyclohexane; water at 70 - 75℃; Stage #2: 1,1,1-tri(hydroxymethyl)propane; acrylic acid With toluene-4-sulfonic acid In cyclohexane; water at 95 - 130℃; for 6 - 10h;
With methanesulfonic acid; hydroquinone In toluene at 120℃; for 5h;

Upstream product

• 103205-80-7 2-hydroxymethyl-2-vinyl-propane-1,3-diol 
• 50-00-0 formaldehyd 
• 123-72-8 butyraldehyde 
• 41966-25-0 2,2-dimethylolbutanal 
• 105790-11-2 4-acetoxy-3,3-bis-acetoxymethyl-but-1-ene 
• 110-89-4 piperidine 
• 2591-86-8 N-Formylpiperidine 
• 1313-99-1 nickel(II) oxide 
• 7397-44-6 tris-methylamino-borane 
• 108-30-5 succinic acid anhydride 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 922-63-4 ethylacrolein 
• 95461-66-8 2,2-bis(hydroxymethyl)-1,4-butanediol 

Downstream Products

• 78-16-0 trimethylolpropane triheptanoate 
• 4826-87-3 1-octanoyloxy-2,2-bis-octanoyloxymethyl-butane 
• 126-57-8 1-nonanoyloxy-2,2-bis-nonanoyloxymethyl-butane 
• 78-17-1 1-decanoyloxy-2,2-bis-decanoyloxymethyl-butane 
• 922-63-4 ethylacrolein 
• 32321-45-2 2-(bromomethyl)-2-ethyl-1,3-propanediol 
• 6974-30-7 1,1,1-tri(bromomethyl)propane 
• 2921-92-8 1-nitryloxy-2,2-bis-nitryloxymethyl-butane 
• 25268-74-0 1-myristoyloxy-2,2-bis-myristoyloxymethyl-butane 
• 20668-43-3 3-propylquinoline 
• 82925-88-0 2,2-bis-(chloromethyl)-1-chlorobutane 
• 23382-23-2 trimethylolpropane trihexanoate 
• 3047-32-3 3-ethyl-3-(hydroxymethyl)oxetane 
• 17940-81-7 tris((trimethylsiloxy)methyl)propane 

Relevant articles and documents

METHOD FOR PREPARING TRIMETHYLOLPROPANE

A method for preparing trimethylolpropane, the method including: subjecting dimethylolbutanal (DMB) to a hydrogenation reaction in the presence of a metal catalyst and an alcohol solvent. During the hydrogenation reaction, a weight ratio of the alcohol solvent based to dimethylolbutanal is 2 to 10.

SEPARATION METHOD OF DIMETHYLOLBUTANAL AND PREPARATION METHOD OF TRIMETHYLOLPROPANE

The present specification relates to a separation method of dimethylolbutanal comprising: a step (A) of making n-butylaldehyde (n-BAL) react with formaldehyde (FA) under an alkylamine catalyst, thereby obtaining a dimethylolbutanal mixed product including dimethylolbutanal (DMB) and trimethylolpropane (TMP); and a step (B) of extracting 95% or more of DMB and 80% or more of TMP from the dimethylolbutanal mixed product by using a counter flow type extraction method using an organic solvent. In the step (B), the organic solvent has a flow rate of 70 to 110 g/min, the DMB mixed product has a flow rate of 40 to 70 g/min, and a weight ratio of the organic solvent to the DMB mixed product is 1.2 to 3. According to an embodiment of the present specification, the separation method can obtain DMB, at a high efficiency, which is used as a raw material for producing TMP. TMP can be obtained at a high efficiency by using the obtained DMB as a raw material for hydrogenation.COPYRIGHT KIPO 2019

Method for continuous preparation of trimethylolpropane

A method for continuous preparation of trimethylolpropane includes: taking a mixture of formaldehyde and butyraldehyde as a raw material, absolute ethyl alcohol as a solvent and sodium hydroxide solution as chemical agent, allowing the mixture and a catalyst to flow and mix in capillaries to form a reaction mixture therein, performing aldol condensation and disproportionated reaction on the reaction mixture in the capillaries to obtain a product comprising trimethylolpropane, wherein the temperature of the reaction mixture is controlled to be 25 to 75 DEG C, and the reaction standing time ranges from 2 to 25 minutes by prolonging the capillaries and/or increasing volume thereof or reducing flow rate of the reaction mixture. Synthesis reaction time of trimethylolpropane is shortened as compared with that of the prior art (4-6 hours), and the yield is increased to 90% from about 75%.

Method For The Combined Production of Polyols In The Presence Of An Inorganic Base

The present invention relates to a process for simultaneously consecutive preparation of polyols by base-catalysed reaction of at least two different mid-chain aldehydes with formaldehyde. The simultaneous consecutive mode of operation makes it possible to achieve high conversions and high selectivities for both aldehydes, with additional achievement of a distinct reduction in the amount of unreacted formaldehyde remaining. This leads to improved process economics, since the energy costs for workup of the formaldehyde stream are distinctly reduced.

Precise Steric Control over 2D versus 3D Self-Assembly of Antimony(III) Alkoxide Cages through Strong Secondary Bonding Interactions

Antimony(III) alkoxide cages were designed as building blocks for predictable supramolecular self-assembly. Supramolecular synthons featuring two Sb···O secondary bonding interactions (SBIs), each SBI stronger than 30 kJ/mol, were used to drive the formation of the supramolecular architectures. Judicious choice of pendant groups provided predictable control over the formation of self-assembled 3D columnar helices, which crystallized with hollow morphologies, or a self-assembled 2D bilayer. The Sb-O stretching frequency provides a spectroscopic signature of Sb···O SBI formation.

PROCESS FOR PRODUCTION OF DITRIMETHYLOLPROPANE

Provided is a method for producing di-TMP by reacting n-butyl aldehyde (NBD), formaldehyde and a base, said method including a first step of reacting the NBD, formaldehyde (1) and a base (I) to obtain a reaction mixture solution containing trimethylolpropane (TMP), di-TMP and 2-ethyl-2-propenal (ECR); a second step of distilling the reaction mixture solution to recover the ECR therefrom; and a third step of sequentially adding the ECR recovered by distillation, and adding at least one of a base (II) and formaldehyde (2), to the reaction mixture solution from which the ECR has been recovered by distillation, and thereby allowing a reaction for production of the di-TMP to proceed gradually, in which TMP is added in any one of the first to third steps or in plural steps of the first to third steps.

METHOD FOR PRODUCING DITRIMETHYLOLPROPANE

The present invention provides a method for producing ditrimethylolpropane which is characterized by the following (1) and (2): (1) a distillation still residue separated from purified trimethylolpropane is subjected to re-distillation under specific conditions to obtain a ditrimethylolpropane-containing solution having given contents of bis-TMP and tri-TMP; and (2) when subjecting the ditrimethylolpropane-containing solution to crystallization with an organic solvent, the crystallization is initiated under pressure at a temperature exceeding a boiling point of the organic solvent as measured under normal pressures, and the resulting crystallization product solution is cooled at a temperature drop rate of 2° C./min or less. According to the above method, it is possible to produce a high-purity ditrimethylolpropane from a distillation still residue obtained upon production of trimethylolpropane in a simple, industrially useful manner.

Method for improving the color number of trimethylolpropane

The present invention relates to a method for producing trimethylolpropane having a low color number by processing a raw reaction solution obtained according to the inorganic Cannizarro process while adhering to precisely defined pH values.

PROCESS FOR PRODUCTION OF DITRIMETHYLOLPROPANE

The present invention provides a method for producing ditrimethylolpropane including reacting n-butyraldehyde with formaldehyde in the presence of a base catalyst to thereby produce trimethylolpropane and ditrimethylolpropane, wherein the method includes (I) a step of reacting n-butyraldehyde with formaldehyde (1) in the presence of a base catalyst (1), to thereby produce a reaction mixture containing trimethylolpropane, ditrimethylolpropane, and 2-ethyl-2-propenal; (II) a step of recovering 2-ethyl-2-propenal through distillation of the produced reaction mixture; and (III) a step of adding, to a distillation residue obtained through recovery of 2-ethyl-2-propenal, the recovered 2-ethyl-2-propenal and formaldehyde (2), and optionally a base catalyst (2), to thereby allow reaction for production of ditrimethylolpropane to proceed, wherein the amounts of formaldehyde (I) and the base catalyst (1) supplied in step I and formaldehyde (2) and the base catalyst (2) supplied in step II are controlled to specific amounts, to thereby effectively produce ditrimethylolpropane. According to the present invention, the yield of di-TMP is considerably increased, and the amount of bis-TMP by-produced can be considerably reduced with respect to the amount of di-TMP (i.e., a product of interest) produced; that is, di-TMP can be effectively produced in an industrially advantageous manner.

PROCESS FOR HYDROGENATING METHYLOLALKANALS

A process for catalytically hydrogenating methylolalkanals of the general formula in which R1 and R2 are each independently a further methylol group or an alkyl group having from 1 to 22 carbon atoms or an aryl or aralkyl group having from 6 to 33 carbon atoms, in the liquid phase over a hydrogenation catalyst, which comprises setting a pH of from 7.0 to 9.0 in the hydrogenation effluent by adding at least one tertiary amine, an inorganic base or an inorganic or organic acid to the hydrogenation feed.