144-19-4

Basic information

• Product Name: 2,2,4-Trimethyl-1,3-pentanediol
• Synonyms: 2,2,4-Trimethylpentandiol;1,3-PENTANEDIOL,2,2,4-TRIME;2,2,4-TRIMETHYLPENTANE-1,3-DIOL 96%;2,2,4-Trimethylpentane-1,3-diol,96%;2,2,4-Trimethylpentane-1,3-diol,98%;2,2,4-TriMethyl-1,3-pentandiol;2,2,4-TriMethyl-1,3-pentanediol (TMPD);2,2,4-Trimethyl-1,3-pentanediol 97%
• CAS NO: 144-19-4
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• EINECS: 205-619-1
• Product Categories: Alcohols;Monomers;Polymer Science;Fine Chemical
• Mol File: 144-19-4.mol

Chemical Properties

• Melting Point: 50-53 °C(lit.)
• Boiling Point: 232 °C(lit.)
• Flash Point: >230 °F
• Appearance: white crystalline powder
• Density: 0,937 g/cm3
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.4513
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 14.81±0.20(Predicted)
• Water Solubility: 31.5g/L at 20℃
• BRN: 1698098
• CAS DataBase Reference: 2,2,4-Trimethyl-1,3-pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,4-Trimethyl-1,3-pentanediol(144-19-4)
• EPA Substance Registry System: 2,2,4-Trimethyl-1,3-pentanediol(144-19-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• RTECS: SA1400000
• TSCA: Yes
• Hazardous Substances Data: 144-19-4(Hazardous Substances Data)

Usage

Uses

Used in Polyester Resins:
2,2,4-Trimethyl-1,3-pentanediol is used as a component in polyester resins for food packaging. It is also used as an insect repellent, providing a dual purpose in this application industry.
Used in Plasticizers, Lubricants, Surface Coatings, and Printing Inks:
2,2,4-Trimethyl-1,3-pentanediol is utilized in the production of plasticizers, lubricants, surface coatings, and printing inks, contributing to the enhancement of these products' performance and quality.
Used in Film-Forming Auxiliaries in Paint Substances:
In the paint industry, 2,2,4-Trimethyl-1,3-pentanediol is used in the synthesis of monoisobutyrate derivatives, which are employed as film-forming auxiliaries in paint substances, improving the overall properties of the paint.
Overall, 2,2,4-Trimethyl-1,3-pentanediol is a versatile compound with applications in various industries, including food packaging, pest control, plastics, coatings, and paints. Its chemical properties make it a valuable component in the development and enhancement of these products.

Production Methods

2,2,4-Trimethyl-1,3-pentanediol is made by reacting isobutyryl chloride with ethyl isobutyrate.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H18O2/c1-6(2)7(10)8(3,4)5-9/h6-7,9-10H,5H2,1-4H3/t7-/m1/s1

Synthetic route

texanol (77-68-9) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With Cr2O3/SO42 solid acid catalyst at 160℃; for 6h; Reagent/catalyst; Temperature;	A n/a B 93%

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With nickel In sodium hydroxide at 20℃; Electrochemical reaction;	92%
With sodium hydroxide
With calcium hydroxide

ethene (74-85-1) + isobutyraldehyde (78-84-2) → 2,4-dimethyl-1,3-pentane diol + 2,2,4-trimethylpentan-1,3-diol (144-19-4) + (2R,3S)-2,4-dimethyl-1,3-pentane diol (3876-46-8, 3876-47-9, 60712-38-1, 82335-99-7, 97906-32-6, 98391-91-4, 103729-84-6, 103729-88-0, 129262-73-3)

Conditions	Yield
Stage #1: ethene; isobutyraldehyde With carbon monoxide; hydrogen; triphenylphosphine; acetylacetonatodicarbonylrhodium(l); L-proline In N,N-dimethyl-formamide at 5℃; under 22502.3 Torr; for 48h; Stage #2: With sodium tetrahydroborate In methanol; N,N-dimethyl-formamide at 0℃; for 0.666667h; Further stages.;	A n/a B n/a C 76%

7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione (221319-52-4) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
	48%

5,5-dimethyl-2,6-bis(propan-2-yl)-1,3-dioxan-4-ol (16889-18-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With water; nickel at 50 - 85℃; Hydrogenation;
With hydrogen; chromium nickel
Multi-step reaction with 2 steps 1: aqueous acetic acid / Abdestillieren des entstehenden Isobutyraldehyds 2: Raney nickel; water / 125 - 165 °C / Hydrogenation View Scheme

3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With sodium amalgam; ethanol; sulfuric acid
With water; nickel at 125 - 165℃; Hydrogenation;

3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2)

Conditions	Yield
With potassium hydroxide zuletzt bei Siedetemperatur;

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6)

Conditions	Yield
With potassium hydroxide

3-Chloro-2-methylpropene (563-47-3) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With sodium hydroxide at 200℃;
With water; calcium carbonate at 150℃; under 40452.9 Torr;

ethyl 2,2,4-trimethyl-3-hydroxyvalerate (7403-65-8) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With lithium aluminium tetrahydride

2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
With sodium hydroxide In methanol

sodium amide + isobutyraldehyde (78-84-2) + acetylene (74-86-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 4-methylpent-1-yn-3-ol (565-68-4) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6)

Conditions	Yield
at 20 - 25℃;

diethyl ether (60-29-7) + sodium amide + isobutyraldehyde (78-84-2) + acetylene (74-86-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 4-methylpent-1-yn-3-ol (565-68-4) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + isobutyl alcohol(?)

Conditions	Yield
at 20 - 25℃;

2.2.4-trimethyl-pentanediol-(1.3)-isobutyrate-(1) → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

Conditions	Yield
durch Verseifen;
With alkaline solution

3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + KOH-solution → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

ethanol (64-17-5) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + sulfuric acid (7664-93-9) + sodium amalgam → 2,2,4-trimethylpentan-1,3-diol (144-19-4)

2,2,4-trimethyl-3-hydroxyvaleric acid (35763-45-2) + alcoholic KOH-solution → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2)

texanol (77-68-9) + alcoholic potash → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2)

3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + aqueous methanolic KOH → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2)

Conditions	Yield
at 25℃;

3-(α-hydroxy-isobutoxy)-2,2,4-trimethyl-valeraldehyde (43079-80-7) + ethanolic KOH-solution → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyric Acid (79-31-2)

2,4-dihydroxy-3,3,5-trimethyl-hexanenitrile (5333-89-1) + KOH-solution → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + hydrogen cyanide (74-90-8) + isobutyric Acid (79-31-2)

2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2,2,4-trimethyl-3-oxo-1-pentanol (15904-30-0) + cis-2,2,4,4-tetramethylcyclobutane-1,3-diol + trans-2,2,4,4-tetramethylcyclobutane-1,3-diol + 3-hydroxy-2,2,4,4-tetramethylcyclobutane-1-one (4916-59-0)

Conditions	Yield
With hydrogen; A280 cobalt on alumina catalyst In isobutyl isobutanoate at 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity;
With hydrogen; A280 cobalt on alumina catalyst promoted with Ir(OAc)x In isobutyl isobutanoate at 135 - 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity;
With hydrogen; G-96B-RS 62percent nickel on kieselguhr catalyst In isobutyl isobutanoate at 160℃; under 46504.7 Torr; for 3h; Product distribution / selectivity;

2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + cis-2,2,4,4-tetramethylcyclobutane-1,3-diol + trans-2,2,4,4-tetramethylcyclobutane-1,3-diol + 3-hydroxy-2,2,4,4-tetramethylcyclobutane-1-one (4916-59-0)

Conditions	Yield
With hydrogen; G-67A 20percent cobalt on silica catalyst In isobutyl isobutanoate at 135℃; under 25877.6 Torr; for 2h; Product distribution / selectivity;
With hydrogen; cesium-promoted copper on silica catalyst In isobutyl isobutanoate at 135℃; under 75007.5 Torr; for 2h; Product distribution / selectivity;

2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2,2,4-trimethyl-3-oxo-1-pentanol (15904-30-0) + cis-2,2,4,4-tetramethylcyclobutane-1,3-diol + trans-2,2,4,4-tetramethylcyclobutane-1,3-diol

Conditions	Yield
With hydrogen; chromium-promoted KL2015-T5 copper on zinc oxide catalyst In isobutyl isobutanoate at 135℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity;

2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + cis-2,2,4,4-tetramethylcyclobutane-1,3-diol + trans-2,2,4,4-tetramethylcyclobutane-1,3-diol

Conditions	Yield
With hydrogen; cesium-promoted copper on silica catalyst In isobutyl isobutanoate at 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity;
With hydrogen; chromium-promoted KL2015-T5 copper on zinc oxide catalyst In isobutyl isobutanoate at 135 - 165℃; under 75007.5 Torr; for 2h; Product distribution / selectivity;

trans-2,2,4,4-tetramethylcyclobutane-1,3-diol → 2,2,4-trimethyl-1-pentanol (123-44-4) + 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2,2,4-trimethyl-3-pentanol (5162-48-1) + 2,4-dimethyl-3-pentanol (600-36-2) + cis-2,2,4,4-tetramethylcyclobutane-1,3-diol

Conditions	Yield
With isobutyl isobutanoate; 5 % platinum on carbon at 50 - 200℃; under 5250.53 - 21002.1 Torr; Product distribution / selectivity; Inert atmosphere;

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + texanol (77-68-9) + 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1) + isobutyric Acid (79-31-2)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 4h; Concentration; Overall yield = 63.6 %Chromat.;

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + texanol (77-68-9) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1) + isobutyric Acid (79-31-2)

Conditions	Yield
Stage #1: isobutyraldehyde With sodium hydroxide at 60℃; for 4h; Stage #2: With hydrogenchloride Concentration; Overall yield = 59.3 %Chromat.;

isobutyraldehyde (78-84-2) → 2,2,4-trimethylpentan-1,3-diol (144-19-4) + texanol (77-68-9) + 2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester (18491-15-1) + isobutyric Acid (79-31-2)

Conditions	Yield
Stage #1: isobutyraldehyde With sodium hydroxide at 60℃; for 4h; Stage #2: With hydrogenchloride Concentration; Overall yield = 85.4 %Chromat.;

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 2,2,4-trimethyl-3-oxo-1-pentanol (15904-30-0)

Conditions	Yield
With tert.-butylhydroperoxide; [π-C5H5N(+)(CH2)15CH3]3(PMo12O40)(3-) In benzene for 24h; Heating;	100%
With dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 12h; chemoselective reaction;	99%
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol; oxygen; nitric acid at 20℃; for 5h; Catalytic behavior;	96%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + benzoyl chloride (98-88-4) → 2,2,4-trimethyl-1,3-pentanediol monobenzoate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;	100%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6)

Conditions	Yield
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 0.5h;	98%
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; sodium hypochlorite; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;	96%
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Reagent/catalyst; Inert atmosphere;	96%

4-(4-t-butylphenylsulphinyl)acetophenone + 2,2,4-trimethylpentan-1,3-diol (144-19-4) → C26H36O3S

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 105℃; for 7h; Inert atmosphere;	98%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + butyric acid (107-92-6) → C17H32O4

Conditions	Yield
With potassium dihydrogenphosphate; sodium hydrogensulfate monohydrate at 160℃; for 8h; Reagent/catalyst; Inert atmosphere;	97%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → dimethyl(3-hydroxy-2,2,4-trimethylpentyloxy)(1,1,2-trimethylpropyl)silane (1061244-98-1)

Conditions	Yield
With 1-methyl-1H-imidazole; iodine In dichloromethane at 20℃; for 0.0833333h;	96%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + 3-Chloro-2-methylpropene (563-47-3) → 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol (526218-21-3)

Conditions	Yield
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydroxide; tetrabutylammomium bromide In water at 50℃; Stage #2: 3-Chloro-2-methylpropene In water at 100℃; for 3.83333h;	94.1%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + (1S,2R)-1,2-diphenylethane-1,2-diol (579-43-1) → 4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane (24571-18-4)

Conditions	Yield
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 61h;	94%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + allyl bromide (106-95-6) → 1,3-bis(allyloxy)-2,2,4-trimethylpentane (5511-07-9)

Conditions	Yield
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;	93%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 2,2,4-trimethyl-3-hydroxyvaleric acid (35763-45-2)

Conditions	Yield
With sodium hypochlorite; sodium chlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl In aq. phosphate buffer; acetonitrile at 25℃; for 7h; pH=6.8; Catalytic behavior; Reagent/catalyst;	92%
With potassium permanganate; water

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + 3-oxo-2,2,4-trimetheyl-1-pentanal (1482-01-5)

Conditions	Yield
With sodium hypochlorite; C9H14NO; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere;	A 92% B 6%
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;	A 69% B 17%

diazomethane (186581-53-3, 908094-01-9) + 2,2,4-trimethylpentan-1,3-diol (144-19-4) → methyl 3-hydroxy-2,2,4-trimethylpentanoate (67498-08-2)

Conditions	Yield
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hypochlorite; sodium chlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl In aq. phosphate buffer; water; acetonitrile for 7h; pH=6.8; Inert atmosphere; Stage #2: diazomethane In diethyl ether Reagent/catalyst; Inert atmosphere;	92%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + trans-Stilbene oxide (1439-07-2) → 4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane (24571-18-4)

Conditions	Yield
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 46h;	91%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + benzoic acid (65-85-0) → 2,2,4-Trimethyl-1,3-pentanediol Dibenzoate (68052-23-3)

Conditions	Yield
With H2SO4/TiO2-La2O3-solid acid catalyst In dibutyl ether at 170 - 180℃; for 10h;	90.5%

tert-butyl acetoacetate (1694-31-1) + 2,2,4-trimethylpentan-1,3-diol (144-19-4) → 2,2,4-Trimethylpentane-1,3-diol bisacetoacetate (58213-74-4)

Conditions	Yield
In xylene for 0.5h; Heating;	87%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + acetic anhydride (108-24-7) → 1,3-diacetoxy-2,2,4-trimethyl-pentane (4100-09-8)

Conditions	Yield
bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 1h;	87%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 3-oxo-2,2,4-trimetheyl-1-pentanal (1482-01-5)

Conditions	Yield
With sodium hypochlorite; 1-methyl-2-azaadamantane-N-oxyl; tetrabutylammomium bromide; potassium bromide In dichloromethane; sodium hydrogencarbonate at 0℃; for 0.333333h;	87%
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; sodium hypochlorite; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;	87%
With sodium hypochlorite; 3-methyl-4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere;	84%
With polystyrene-supported oxorhenium catalyst activated by iPrOH; dimethyl sulfoxide In toluene for 15h; Heating; Dean-Stark apparatus;	82%
With sodium hypochlorite; C8H12NO; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere;	72%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 3-hydroxy-2,2,4-trimethylpentanenitrile (59346-56-4)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; ammonium acetate In water; acetonitrile at 20℃; for 8h; chemoselective reaction;	87%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + 1,1,2-triphenyl-1,2-ethanediol (6296-95-3) → benzophenone (119-61-9) + 4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane (24571-18-4)

Conditions	Yield
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 42h;	A 86% B 84%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + diphenylsilanediol (947-42-2) + boric acid (11113-50-1) → (C6H5)2Si(OBO2C3H3(CH3)2CH(CH3)2)2 (255849-43-5)

Conditions	Yield
In toluene byproducts: H2O; inert atmosphere; refluxing (8 h); evapn., hexanes addn., filtering, pptn. on concg. (-22°C, severalh); elem. anal.;	85.2%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + isobutyryl chloride (79-30-1) → 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (6846-50-0)

Conditions	Yield
With zinc(II) chloride In dichloromethane at 0 - 40℃; Molecular sieve;	85.2%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + 2-(4-bromomethyl-2-methoxyphenyl)benzothiazole (949913-33-1) → 1-[4-(benzothiazol-2-yl)-3-methoxybenzyloxyl]-2,2,4-trimethylpentan-3-ol (1225265-83-7)

Conditions	Yield
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: 2-(4-bromomethyl-2-methoxyphenyl)benzothiazole In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Williamson synthesis; Inert atmosphere;	85%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + carbonic acid dimethyl ester (616-38-6) → methanol (67-56-1) + 4-isopropyl-5,5-dimethyl-[1,3]dioxan-2-one (32368-14-2)

Conditions	Yield
zinc(II) acetylacetonate at 20 - 155℃; for 10.5h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation;	A n/a B 84.9%
zinc diacetate at 20 - 155℃; for 12.5h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation;	A n/a B 81.3%
tin(II) octanoate at 20 - 155℃; for 18h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation;	A n/a B 78.2%
zinc stearate at 20 - 155℃; for 18h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation;	A n/a B 73.5%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → 3-hydroxy-2,2,4-trimethyl-pentanal (918-79-6) + 2,2,4-trimethyl-3-hydroxyvaleric acid (35763-45-2)

Conditions	Yield
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Reagent/catalyst; Inert atmosphere;	A 81% B 6%

2,2,4-trimethylpentan-1,3-diol (144-19-4) + 1,1,3,3-tetraphenyldisiloxane-1,3-diol (1104-93-4) + boric acid (11113-50-1) → O(Si(C6H5)2OBO2C3H3(CH3)2CH(CH3)2)2 (255849-48-0)

Conditions	Yield
In not given byproducts: H2O; inert atmosphere; elem. anal.;	80%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → trans-2-chloro-4-isopropyl-5,5-dimethyl-1,3,2-dioxaphosphorinane (80812-98-2, 95115-80-3, 99835-52-6, 103228-82-6)

Conditions	Yield
With triethylamine; phosphorus trichloride In benzene for 4h; Ambient temperature;	76%
With triethylamine; phosphorus trichloride In diethyl ether for 2h; Ambient temperature;	71%

2,2,4-trimethylpentan-1,3-diol (144-19-4) → C16H32O4Si

Conditions	Yield
With silica gel; sodium hydroxide for 24h; Reagent/catalyst; Inert atmosphere;	73%

Upstream product

• 16889-18-2 5,5-dimethyl-2,6-bis(propan-2-yl)-1,3-dioxan-4-ol 
• 918-79-6 3-hydroxy-2,2,4-trimethyl-pentanal 
• 78-84-2 isobutyraldehyde 
• 563-47-3 3-Chloro-2-methylpropene 
• 7403-65-8 ethyl 2,2,4-trimethyl-3-hydroxyvalerate 
• 6846-50-0 2,2,4-trimethyl-1,3-pentanediol diisobutyrate 
• 74-86-2 acetylene 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 35763-45-2 2,2,4-trimethyl-3-hydroxyvaleric acid 
• 77-68-9 texanol 
• 43079-80-7 3-(α-hydroxy-isobutoxy)-2,2,4-trimethyl-valeraldehyde 
• 5333-89-1 2,4-dihydroxy-3,3,5-trimethyl-hexanenitrile 

Downstream Products

• 15721-83-2 2,2,4-trimethyl-1,3-bis-nonanoyloxy-pentane 
• 3601-65-8 2,3,4-trimethyl-pentanal 
• 35763-45-2 2,2,4-trimethyl-3-hydroxyvaleric acid 
• 565-80-0 2,4-dimethylpentan-3-one 
• 4100-09-8 1,3-diacetoxy-2,2,4-trimethyl-pentane 
• 77-68-9 texanol 
• 3358-28-9 2,2,4,4-Tetramethyltetrahydrofuran 
• 102369-79-9 2,3,4,4-Tetramethyl-tetrahydro-furan 
• 5451-59-2 2,2,4-trimethyl-1,3-pentanediol, diformate 
• 31951-95-8 4t-isopropyl-2r-phenoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-sulphide 
• 96794-66-0 4-isopropyl-5,5-dimethyl-2-phenyl-[1,3,2]dioxaborinane 
• 625-65-0 2,4-dimethyl-2-pentene 
• 6846-50-0 2,2,4-trimethyl-1,3-pentanediol diisobutyrate 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Trimerization of aldehydes with one α-hydrogen catalyzed by sodium hydroxide

Trimerization of 2-methylpropanal (isobutyraldehyde) is a simple and effective method to synthesize 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate and 2,2,4-trimethyl-1,3-pentanediol-3-monoisobutyrate which are often used as film forming auxiliaries in paints. The use of solid sodium hydroxide as a catalyst provides an excellent yield of above 85 % after the optimization of the reaction time and the catalyst dosage. Furthermore, trimerization of four other aldehydes with one α-hydrogen catalyzed by solid sodium hydroxide can also take place and the yield of 1,3-diol monoesters reaches 50-70 %. Trimerization of aldehydes with one α-hydrogen can be explained by a three-step reaction mechanism: (i) aldol condensation of aldehyde; (ii) crossed Cannizzaro reaction; and (iii) esterification of carboxylic acid and alcohol.

CATALYST AND METHOD FOR HYDROGENATION OF 1,3-CYCLOBUTANEDIKETONE COMPOUND

Catalyst for hydrogenation of 1,3-cyclobutanediketone compound is provided, which includes a support and VIIIB group transition metal loaded thereon. The support includes a first oxide powder with a surface wrapped by a second oxide. The first oxide includes silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, zinc oxide, or a combination thereof. The second oxide has a composition of MxAl(1-x)O(3-x)/2, M is alkaline earth metal, and x is from 0.3 to 0.7.

Preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate

The invention discloses a preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. The preparation method includes the steps that isobutyraldehyde serves as the raw material and is converted into 2,2,4-trimethyl-1,3-pentanediol with a base catalyst, and then, 2,4-trimethyl-1,3-pentanediol is converted into 2,2,4-trimethyl-1,3-pentanediol diisobutyrate with an acid catalyst. The preparation method of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate has the advantages that the material source is wide, the technological process is simple, the conversion rate is high, the product purity is high, and the cost is low.

Method for simultaneous synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and 2,2,4-trimethyl-1,3-pentanediol

The present invention relates to the field of fine chemicals, and in particular relates to a method for simultaneous synthesis of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and 2,2,4-trimethyl-1,3-pentanediol. The 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and the 2,2,4-trimethyl-1,3-pentanediol can be obtained by transesterification of 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate under the effect of an acidic catalyst according to the method. A new method for synthesis of the 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and the 2,2,4-trimethyl-1,3-pentanediol is provided, and according to the situation, product separation can be performed by ordinary distillation or reactive distillation. When the ordinary distillation is used for the product separation, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate conversion rate is 45 to 60%. When the reactive distillation is used for the product separation, the 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate conversion rate is high and can reach 98 to 99%.

Isoleucine-catalyzed direct asymmetric aldol addition of enolizable aldehydes

Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

PROCESS FOR THE ISOMERIZATION OF 2,2,4,4-TETRAALKYLCYCLOBUTANE-1,3-DIOLS

Disclosed is a process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols, such as 2,2,4,4-tetramethylcyclobutane-1,3-diol, by contacting the diol with a supported ruthenium catalyst in the presence of hydrogen at elevated pressures and temperatures. The process is carried under conditions in which there is no net production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase.

Asymmetric acid-catalyzed meerwein-ponndorf-verley-aldol reactions of enolizable aldehydes

A highly, stereo- and regioselective Meerwein-Ponndorf-Verley-Aldol etherification process of enolizable aldehydes is described. This new transformation is catalyzed by trifluoroacetic acid. The method also allows cross-aldol reactions with α-branched enolizable aldehydes and thus provides access to defined configured quaternary stereogenic centers.

PROCESS FOR THE PREPARATION OF TETRAALKYLCYCLOBUTANE-1,3-DIOL IN THE PRESENCE OF A COBALT-BASED CATALYST

The present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the presence of a cobalt-based catalyst.

PROCESS FOR THE PREPARATION OF A TETRAALKYCYCLOBUTANE-1,3-DIOL USING A PROMOTED-COPPER CATALYST

The present disclosure relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a promoted copper-based catalyst.

PROCESS FOR THE PREPARATION OF A TETRAALKYLCYCLOBUTANE-1,3-DIOL USING AN IRIDIUM-PROMOTED COBALT-BASED CATALYST

The present disclosure relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of an iridium-promoted cobalt-based catalyst.