2516-92-9

Basic information

• Product Name: Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate
• Synonyms: BIS(2,2,6,6-TETRAMETHYLPIPERIDINE-1-OXY)-SEBACATE;1-Piperidinyloxy, 4,4-(1,10-dioxo-1,10-decanediyl)bis(oxy)bis2,2,6,6-tetramethyl-;Piperidinooxy, 4-hydroxy-2,2,6,6-tetramethyl-, sebazat (2:1);4,4'-[(1,10-dioxo-1,10-decanediyl)bis(oxy)]bis[2,2,6,6-tetramethyl-1-Piperidinyloxy;bis(i-0xyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate;BIS(2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY-4-YL) SEBACATE;4,4'-[(1,10-Dioxo-1,10-decandiyl)bis(oxo)bis[2,2,6,6-tetramethyl-1-piperidinyloxy];Bis-(2,2,6,6-tetramethylpiperidine-1-oxyl)-sebacate
• CAS NO: 2516-92-9
• Molecular Formula: C₂₈H₅₀N₂O₆
• Molecular Weight: 510.7064
• EINECS: 1308068-626-2
• Product Categories: Pharmaceutical Intermediates
• Mol File: 2516-92-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 99.0 to 103.0 °C
• Boiling Point: 523.5°C at 760 mmHg
• Flash Point: 270.4°C
• Appearance: /
• Density: 1.12 at 22℃
• Vapor Pressure: 3.81E-13mmHg at 25°C
• CAS DataBase Reference: Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate(2516-92-9)
• EPA Substance Registry System: Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate(2516-92-9)

Safety Data

• Hazardous Substances Data: 2516-92-9(Hazardous Substances Data)

Usage

General Description

Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate is a chemical compound commonly used as a non-polluting, non-toxic, and non-flammable stabilizer for various materials, including plastics, rubber, adhesives, and coatings. It acts as a hindered amine light stabilizer (HALS), providing protection against degradation caused by UV radiation and thermal oxidation. Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate is particularly effective at inhibiting the degradation of polymers and extending their service life in outdoor applications. It works by scavenging free radicals and preventing their detrimental effects on the material. Bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate is considered to be environmentally friendly and is approved for use in various industries, including food packaging and agricultural applications.

InChI:InChI=1/C19H35NO6/c1-18(2)12-14(21)13-19(3,4)20(18)26-15(17(24)25)10-8-6-5-7-9-11-16(22)23/h14-15,21H,5-13H2,1-4H3,(H,22,23)(H,24,25)/p-2

Synthetic route

bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate (52829-07-9) → bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9)

Conditions	Yield
With sodium tungstate; dihydrogen peroxide; edetate disodium In methanol; acetonitrile	10%

bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate (52829-07-9) → bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + C28H51N2O5 (80004-15-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane 1) 273 K, 1 h, 2) 1 h, reflux;

TEMPOL (45985-24-8, 2226-96-2) + sebacic acid mono methyl ester (818-88-2) → bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9)

Conditions	Yield
With sodium methylate In n-heptane Heating / reflux;

sebacoyl chloride (111-19-3) + TEMPOL (45985-24-8, 2226-96-2) → bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h;

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + octane (111-65-9) → bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate

Conditions	Yield
With dihydrogen peroxide at 75 - 80℃; for 9h; Reagent/catalyst; Temperature;	89.7%
With iron(III) chloride; dihydrogen peroxide; acetic acid In water; acetonitrile at 76℃; for 4h; Heating / reflux;	31%

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → di(1-phenoxy-2,2,6,6-tetramethyl-piperidin-4-yl) sebacate (371756-16-0)

Conditions	Yield
With pyridine; tert.-butylnitrite; aniline In n-heptane; ethyl acetate	47.9%

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + cyclohexane (110-82-7) → bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

Conditions	Yield
With methanesulfonic acid; dihydrogen peroxide; iron(II) sulfate In water; acetonitrile at 55℃; for 5.5h; Heating / reflux;	43%

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate (52829-07-9)

Conditions	Yield
With ethanethiol In benzene	17%

styrene (292638-84-7) + bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → polymer, Mn (g/mol) = 20600, Mw/Mn = 1.68; monomer(s): styrene; decanedioic acid bis(1-oxy-2,2,6,6-tetramethylpiperidin-4-yl) ester

Conditions	Yield
With dibenzoyl peroxide at 130℃; for 2.5h;	53 % Turnov.

styrene (292638-84-7) + bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → polymer, Mn (g/mol) = 25000, Mw/Mn = 1.72; monomer(s): styrene; decanedioic acid bis(1-oxy-2,2,6,6-tetramethylpiperidin-4-yl) ester

Conditions	Yield
With dibenzoyl peroxide at 130℃; for 14h;	86 % Turnov.

styrene (292638-84-7) + bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → polymer, Mn (g/mol) = 26300, Mw/Mn = 1.60; monomer(s): styrene; decanedioic acid bis(1-oxy-2,2,6,6-tetramethylpiperidin-4-yl) ester

Conditions	Yield
With dibenzoyl peroxide at 130℃; for 5h;	76 % Turnov.

nonan-1-al (124-19-6) + bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate

Conditions	Yield
With dihydrogen peroxide; acetic acid; calcium chloride; copper dichloride In water; toluene at 20 - 40℃; for 11h; Product distribution / selectivity;
With dihydrogen peroxide; acetic acid; copper dichloride In water; toluene; tert-butyl alcohol at 25 - 40℃; for 12h; Product distribution / selectivity;

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + n-heptane (142-82-5) → bis(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

Conditions	Yield
With hydrogenchloride; iron(III) chloride; dihydrogen peroxide In water; acetonitrile at 33 - 68℃; for 6.5h;

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + oct-1-ene (111-66-0) → C44H80N2O6 + C44H80N2O6 (865710-98-1)

Conditions	Yield
With tert.-butylhydroperoxide; copper(ll) bromide In water at 60℃; for 0.5h; Product distribution / selectivity;
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 60℃; for 2.5 - 5.25h; Product distribution / selectivity;
With tert.-butylhydroperoxide; copper dichloride In water at 60℃; for 3h; Product distribution / selectivity;

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + 1-bromo-3-propanol (627-18-9) → bis[1-(3-hydroxypropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] Sebacate (1098596-25-8)

Conditions	Yield
With tri-n-butyl-tin hydride In chlorobenzene

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + 12-bromododecanol (3344-77-2) → Bis[1-(12-hydroxy-1-dodecyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] Sebacate (1098596-19-0)

Conditions	Yield
With tri-n-butyl-tin hydride In chlorobenzene

1-bromo-2-propanol (19686-73-8) + bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → bis[1-(2-hydroxypropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] Sebacate (1098596-20-3)

Conditions	Yield
With tri-n-butyl-tin hydride In chlorobenzene

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) + boron trifluoride diethyl etherate (109-63-7) → 4,4'-[(1,10-dioxo-1,10-decanediyl)bis(oxy)]bis[2,2,6,6-tetramethyl-1-oxo-piperidinium] tetrafluoroborate

Conditions	Yield
Stage #1: boron trifluoride diethyl etherate With isopentyl nitrite In diethyl ether for 0.0833333h; Inert atmosphere; Stage #2: bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate In diethyl ether for 0.5h; Inert atmosphere;

bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate (2516-92-9) → 1,10-bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl) decanedioate (30538-92-2)

Conditions	Yield
With ascorbic acid In 1,4-dioxane; water at 20℃; for 1h; Inert atmosphere;

Upstream product

• 45985-24-8 TEMPOL 
• 818-88-2 sebacic acid mono methyl ester 
• 111-19-3 sebacoyl chloride 
• 52829-07-9 bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate 

Downstream Products

• 371756-16-0 di(1-phenoxy-2,2,6,6-tetramethyl-piperidin-4-yl) sebacate 
• 52829-07-9 bis-(2,2,6,6-tetramethyl-4-piperidinyl) sebacate 

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