36177-92-1

Basic information

• Product Name: N-BUTYL TRIACETONEDIAMINE
• Synonyms: N-BUTYL TRIACETONEDIAMINE;N-BUTYL-TAD;N-butyl-2,2,6,6-tetramethyl-4-Piperidinamine;N-butyl-2,2,6,6-tetramethylpiperidin-4-amine;4-(Butylamino)-2,2,6,6-tetramethylpiperidine;N-Butyl-2,2,6,6-tetramethylpiperidin-4-amin;Butyl(2,2,6,6-tetramethyl-4-piperidinyl)amine;N-Butyl-2,2,6,6-tetramethylpiperidine-4-amine
• CAS NO: 36177-92-1
• Molecular Formula: C₁₃H₂₈N₂
• Molecular Weight: 212.37
• EINECS: 252-899-6
• Mol File: 36177-92-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 249.7 °C at 760 mmHg
• Flash Point: 97 °C
• Appearance: /
• Density: 0.87 g/cm³
• Vapor Pressure: 0.0226mmHg at 25°C
• Refractive Index: 1.471
• PKA: 10.89±0.10(Predicted)
• Water Solubility: 797.5g/L at 20℃
• CAS DataBase Reference: N-BUTYL TRIACETONEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BUTYL TRIACETONEDIAMINE(36177-92-1)
• EPA Substance Registry System: N-BUTYL TRIACETONEDIAMINE(36177-92-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 36177-92-1(Hazardous Substances Data)

Usage

General Description

N-BUTYL TRIACETONEDIAMINE, also known as NBTA, is a chemical compound commonly used as a catalyst for epoxy resins. It has a molecular formula of C13H27NO4 and a molecular weight of 257.36 g/mol. NBTA is a clear, colorless to slightly yellow liquid with a mild odor. It is soluble in organic solvents such as acetone, toluene, and ethyl acetate. NBTA is known for its high reactivity and selectivity, making it an effective catalyst for various industrial processes such as polymerization and chemical synthesis. It is also used in adhesives, sealants, and coatings. However, it is important to handle NBTA with proper care, as it can be harmful if inhaled, swallowed, or in contact with skin, and may cause irritation to the eyes and skin.

InChI:InChI=1/C13H28N2/c1-6-7-8-14-11-9-12(2,3)15-13(4,5)10-11/h11,14-15H,6-10H2,1-5H3

Synthetic route

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + N-butylamine (109-73-9) → 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
Pt on carbon In water	98%
With hydrogen at 100℃; under 6750.68 Torr; for 5h; Pressure; Temperature; Autoclave;	97.4%
Stage #1: 2,2,6,6-Tetramethyl-4-piperidone; N-butylamine With acetic acid at 25℃; for 12h; Stage #2: With methanol; sodium tetrahydroborate for 8h; Temperature; Reagent/catalyst;	95.2%

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE (36768-62-4) + butyraldehyde (123-72-8) → 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
With hydrogen In toluene at 60 - 120℃; under 7500.75 Torr; for 5h; Reagent/catalyst; Autoclave;	15%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) + N-butylamine (109-73-9) → 4-hydroxy-2,2,6,6-tetramethylpiperidine (2403-88-5) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
With hydrogen In 1,4-dioxane at 120℃; under 30003 Torr;

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / Reflux 2: 5%-palladium/activated carbon; hydrogen / cyclohexane / 4 h / 60 - 120 °C / 11251.1 Torr / Autoclave View Scheme

butyl-(2,2,6,6-tetramethyl-piperidin-4-ylidene)-amine (35517-43-2) → 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In cyclohexane at 60 - 120℃; under 11251.1 Torr; for 4h; Autoclave;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → 2-chloro-4,6-bis-((2,2,6,6-tetramethyl-piperidin-4-yl)butylamino)-1,3,5-triazine

Conditions	Yield
With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 12h; Reagent/catalyst; Solvent; Temperature; Cooling with ice;	98.3%
With sodium carbonate In toluene at 80℃; for 3h; Product distribution / selectivity;
With sodium carbonate In toluene at 80℃; for 3h; Product distribution / selectivity;
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 4-n-butylamino-2,2,6,6-tetramethylpiperidine In xylene at 20℃; for 0.5h; Stage #2: With sodium hydroxide In water; xylene at 20 - 95℃; for 2h;
With potassium hydroxide In water; toluene at 20 - 45℃; Reagent/catalyst; Solvent;

formaldehyd (50-00-0) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → butyl-methyl-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-amine (36177-99-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol; water at 80 - 140℃; under 15001.5 - 31503.2 Torr; Solvent; Autoclave;	93.7%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-butyl-N-(2,2,6,6-tetramethyl-piperidin-4-yl)formamide (124172-46-9)

Conditions	Yield
With acetic acid; boric acid In xylene for 6h; Inert atmosphere; Reflux;	92%

C90H165Cl3N22O3 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C129H246N28O3

Conditions	Yield
With sodium hydroxide In water; xylene Reflux;	90.9%

chloroform (67-66-3) + 2,6-di-tert-butylphenol (128-39-2) + cyclohexanone (108-94-1) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-cyclohexanecarboxylic acid butyl-(2,2,6,6-tetramethyl-piperidin-4-yl)-amide

Conditions	Yield
With sodium hydroxide at 10℃;	85%

2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide (4090-55-5) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → 2-[butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-5,5-dimethyl[1,3,2]dioxaphosphinane-2-oxide

Conditions	Yield
With triethylamine In acetonitrile for 7h; Inert atmosphere; Reflux;	81.7%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + 4-(2-bromoethyloxy)benzaldehyde (52191-15-8) → C22H36N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	78.2%

formaldehyd (50-00-0) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C14H30N2 + butyl-methyl-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-amine (36177-99-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol; water at 80 - 140℃; under 15001.5 - 31503.2 Torr; Autoclave;	A 77.8% B n/a

C78H144Cl2N16O4 (1372610-77-9) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C104H198N20O4

Conditions	Yield
With sodium hydroxide In water; xylene for 20h;	76%

C15H13BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C28H40N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	75.2%

chloroform (67-66-3) + 2,6-di-tert-butylphenol (128-39-2) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + acetone (67-64-1) → N-butyl-2-(3,5-di-tert-butyl-4-hydroxy-phenyl)-N-(2,2,6,6-tetramethyl-piperidin-4-yl)-isobutyramide

Conditions	Yield
With sodium hydroxide at 10℃;	75%

(3-chloro-propyl)-dodecyl sulfide (197514-15-1) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C28H58N2S (745044-20-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h;	73%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + 4-(4-bromobutoxy)benzaldehyde (72621-19-3) → C24H40N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	69.7%

glycidyl n-dodecyl thioether (20256-76-2) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C28H58N2OS

Conditions	Yield
at 110℃; for 25h;	69%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-diaminohexane (61260-55-7) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → N,N'-bis-(2,2,6,6-tetramethylpiperidin-4-yl)-N,N'-bis-{2,4-bis-{n-butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino}-[1,3,5]triazin-6-yl}hexane-1,6-diamine (210988-99-1)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 4-n-butylamino-2,2,6,6-tetramethylpiperidine With sodium hydroxide In water; toluene at 70℃; for 1h; Inert atmosphere; Stage #2: N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-diaminohexane In water; toluene at 20℃; Reflux; Inert atmosphere;	69%

C29H23BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C42H50N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	66.5%

2,4-dichloro-6-(diethylamino)-1,3,5-triazine (1722-19-6) + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → 2,4-bis[N-(2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine

Conditions	Yield
With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene	66%

C17H17BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C30H44N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	65.8%

C31H27BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C44H54N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	62.1%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + 4-((6-bromohexyl)oxy)benzaldehyde (141823-14-5) → C26H44N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	58.3%

C19H21BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C32H48N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	54.3%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + 4-(8-bromooctane-1-oxy)benzaldehyde → C28H48N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	51.7%

C33H31BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C46H58N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	50.3%

C21H25BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C34H52N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	49.2%

4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) + 4-(10-bromo-n-decyloxy)benzaldehyde (143773-73-3) → C30H52N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	46.1%

C35H35BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C48H62N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	44.2%

C23H29BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C36H56N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	42.1%

4-(12-bromo-dodecyloxy)-benzaldehyde + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C32H56N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	39.6%

C37H39BrO2 + 4-n-butylamino-2,2,6,6-tetramethylpiperidine (36177-92-1) → C50H66N2O2

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	39.3%

Upstream product

• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 109-73-9 N-butylamine 
• 35517-43-2 butyl-(2,2,6,6-tetramethyl-piperidin-4-ylidene)-amine 
• 36768-62-4 4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE 
• 123-72-8 butyraldehyde 

Downstream Products

• 80387-98-0 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazine-6-yl]-1, 5,8,12-tetraazadodecane 
• 69303-52-2 2,2-bis[4-{3-[N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-2-hydroxypropoxy}phenyl]propane 
• 63812-63-5 2,4-dichloro-6-[(2',2',6',6'-tetramethyl-piperidin-4'-yl)-butylamino]-1,3,5-triazine 

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The invention provides a preparation method of a multifunctional light stabilizer, and particularly relates to the field of light stabilizers; the structure of the multifunctional light stabilizer isshown as follows, wherein the R1 is any one of oxygen, hydrogen, hydroxyl, halogen, C1-C20 alkyl, C4-C10 naphthenic base, C1-C12 alkoxy, C4-C12 naphthenyloxy, C1-C10 chain enyloxy or cyclic enyloxy, C1-C10 cyano substituted alkyloxy and C1-C15 aromatic alkoxy; and R2 is hydrogen, a C1-C20 alkyl group or an oxygen atom substituted C1-C20 alkyl group. The triazine multifunctional light stabilizer with the double hindered amine piperidine groups can be prepared, and the triazine multifunctional light stabilizer has more excellent ultraviolet absorption spectrum characteristics, free radical capturing capacity and high polymer compatibility and also has certain flame retardant characteristics.

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The invention discloses a preparation process of a light stabilizer intermediate N-butyl-2,2,6,6-tetramethyl-4-piperidylamine. The preparation process comprises the following steps: dissolving triacetonamine in excess n-butylamine, introducing hydrogen gas under the action of a metal catalyst, raising the temperature, and directly performing hydrogenated reduction and amination to obtain the target product N-butyl-2,2,6,6-tetramethyl-4-piperidylamine. The process disclosed by the invention has the advantages that the procedures are simple, no reaction medium is added, the capacity is big, by-products are few, the conversion rate of the main raw material triacetonamine is high, and the excess auxiliary material n-butylamine can be recycled.

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