77-58-7

Basic information

• Product Name: Dibutyltin dilaurate
• Synonyms: DBTDL;Aids010213;Aids-010213;Ditin butyl dilaurate(dibutyl bis((1-oxododecyl)oxy)-Stannane);Two dibutyltin dilaurate;dibutyltin(IV) dodecanoate;The two butyltintwo lauricacid;Dibutyltin dilaurate 95%
• CAS NO: 77-58-7
• Molecular Formula: C₃₂H₆₄O₄Sn
• Molecular Weight: 631.56
• EINECS: 201-039-8
• Product Categories: organotin compound;PU additive;Used for plastic heat stabilizer, organic silicon material treatment;Solvent;Classes of Metal Compounds;Sn (Tin) Compounds;Typical Metal Compounds;Organometallic Reagents;Organotin;Organotins
• Mol File: 77-58-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 22-24°C
• Boiling Point: >204°C/12mm
• Flash Point: >230 °F
• Appearance: Clear pale yellow/Oily Liquid
• Density: 1.066 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.2 mm Hg ( 160 °C)
• Refractive Index: n20/D 1.471(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: <1.43mg/l
• Water Solubility: <0.1 g/100 mL at 20℃
• Stability: Stability Combustible. Incompatible with strong oxidizing agents. May be air sensitive.
• Merck: 14,3038
• BRN: 4156980
• CAS DataBase Reference: Dibutyltin dilaurate(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutyltin dilaurate(77-58-7)
• EPA Substance Registry System: Dibutyltin dilaurate(77-58-7)

Safety Data

• Hazard Codes: T+,N,C,T
• Statements: 22-26-36/38-50/53-68-48/25-43-34-61-60
• Safety Statements: 26-28-36/37-45-60-61-36/37/39-24-53
• RIDADR: UN 2922 8/PG 3
• WGK Germany: 3
• RTECS: WH7000000
• F: 10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 77-58-7(Hazardous Substances Data)

Usage

Organic tin additive

Dibutyltin dilaurate is an organic tin additives, and can be soluble in benzene, toluene, carbon tetrachloride, ethyl acetate, chloroform, acetone, petroleum ether and other organic solvents and all industrial plasticizers, but insoluble in water. Multipurpose high-boiling organic tin catalyst circulation of dibutyltin dilaurate are usually specially treated liquefaction, and at room temperature as a pale yellow or colorless oily liquid, when low temperature as white crystals, and it can be used for PVC additives, it also has excellent lubricity, transparency, weather resistance, and better resistance for sulfide pollution. It can also uesd the stabilizer of the soft transparent products and efficient lubricants in hard transparent products, and can also be used acrylate rubber and rubber carboxyl crosslinking reaction, the catalyst of synthesis of polyurethane foam and polyester synthetic, and RTV silicone rubber. The above information is edited by the lookchem of Wang Xiaodong.

Chemical properties

It is pale yellow flammable liquid, and soluble in acetone and benzene, can not dissolve in water.

Uses

Different sources of media describe the Uses of 77-58-7 differently. You can refer to the following data:
1. It can be used as PVC heat stabilizers, and it is the earliest used varieties in organotin stabilizers, heat resistance is less than tributyltin maleate, but it has excellent lubricity, weather resistance and transparency can be ok, and it has good compatibility with plasticizers, non-blooming, non-sulfide pollution, no adverse effects on heat sealing and printability. For it is liquid at room temperature, so the dispersion in plastic is better than solid stabilizer.The product is mainly used in soft transparent products or semi-soft products, generally in an amount of 1-2%. In hard products, the product can be used as lubricant, and when used with maleic acid organic tin or thiol-containing organic tin can improve the fluidity of the resin material. Compared with other organic tin, the goods early color large will cause yellow discoloration.The product can also be used as catalysts of synthesizing polyurethane, the curing agents of silicone rubber. In order to enhance the thermal stability, transparency, compatibility with resins, as well as improve the impact strength for hard products and its other properties, now it has developed a number of modified varieties. Lauric acid and other fatty acids is generally added in the category of pure, the epoxy ester or other metal soap stabilizer is also added in. The product is toxic materials. Rat oral is LD50 of 175mg/kg.
2. Stabilizer for polyvinyl chloride resins. Catalyst for curing certain silicones.
3. Di-n-butyltin dilaurate is used as a catalyst for the production of polyurethanes as well as for the transesterification reactions. It is involved in the vulcanization of silicones and a stabilizer in polyvinyl chloride (PVC). It acts as a rust inhibitor for polyurethanes, polyols, silicones and as a fuel additive.
4. Dibutyltin dilaurate has been used as a catalyst in a protocol for the covalent attachment of poly(ethylene glycol) (PEG) to silicon oxide to form a hydrophilic non-fouling surface. It can also be used as a catalyst in the preparation of polymers by reacting hydroxyl-terminated macromonomers and aliphatic diisocyanates.

Production method

It is condensed by DBTO and lauric acid at 60℃. After condensation, vacuum dehydration, cooling, pressure filtration derived products.

Category

Toxic Substances.

Acute toxicity

Oral-rat LD50: 175 mg/kg; oral-mouse LDL0: 710 mg/kg.

Stimulus data

Skin-rabbit 100 mg/24 hours moderate.

Flammability hazard characteristics

Combustible fire.

Storage Characteristics

Treasury should be ventilated and low-temperature drying; and should transport separately with food materials.

Extinguishing agent

Carbon dioxide, sand, water, foam.

Occupational standards

TWA 0.1 mg (Sn)/cubic meter; STEL 0.2 mg (Sn)/cubic meter.

Chemical Properties

yellow liquid

Air & Water Reactions

Dibutyltin dilaurate may be sensitive to air or heat. . Insoluble in water.

Reactivity Profile

Dibutyltin dilaurate is strongly reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents.

Fire Hazard

Dibutyltin dilaurate is combustible.

Safety Profile

Poison by ingestion and intraperitoneal routes. A skin and eye irritant. Avoid the vapor produced by heating. Combustible when exposed to heat or flame; reacts with oxidizers. When heated to decomposition it emits acrid smoke and fumes. See also TIN COMPOUNDS

InChI:InChI=1/2C12H24O2.2C4H9.Sn/c2*1-2-3-4-5-6-7-8-9-10-11-12(13)14;2*1-3-4-2;/h2*2-11H2,1H3,(H,13,14);2*1,3-4H2,2H3;/q;;;;+2/p-2/rC32H64O4Sn/c1-5-9-13-15-17-19-21-23-25-27-31(33)35-37(29-11-7-3,30-12-8-4)36-32(34)28-26-24-22-20-18-16-14-10-6-2/h5-30H2,1-4H3

Synthetic route

lauric acid (143-07-7) + di(n-butyl)tin oxide (818-08-6) → dibutyltin dilaurate (77-58-7)

Conditions	Yield
at 20 - 60℃; for 2.5h; Temperature;	97.2%

Bu2Sn(CH2CH2OCO-n-C11H23)2 (125610-44-8) → dibutyltin dilaurate (77-58-7)

Conditions	Yield
In neat (no solvent) Kinetics; byproducts: C2H4; decompn. (140°C, 5 h);

lauric acid (143-07-7) + dibutyltin chloride (683-18-1) → dibutyltin dilaurate (77-58-7)

Conditions	Yield
With sodium hydroxide In n-heptane at 50℃;

dibutyltin dilaurate (77-58-7) + 3-Chloropropyltrimethoxysilan (2530-87-2) → octakis(3-chloropropyl)octasilsesquioxane (161678-38-2)

Conditions	Yield
Stage #1: 3-Chloropropyltrimethoxysilan With hydrogenchloride In methanol at 20℃; Stage #2: dibutyltin dilaurate In methanol for 48h;	35%

dibutyltin dilaurate (77-58-7) → tin (7440-31-5)

Conditions	Yield
In gaseous matrix deposition onto Ti plate by thermal pyrolysis in horizontal tube furnace; at ultrapure Ar flow rate 100 sccm; heating up to 350°C at a rate 50°C/min, kept for 1.5 h, naturally cooled to room temp.; detd. by SEM, XRD;

diphenylphosphinic acid hydrazide (6779-66-4) + dibutyltin dilaurate (77-58-7) → dibutyltin dilaurate{diphenylphosphinic acid hydrazide}

Conditions	Yield
In benzene to a soln. of hydrazide in anhydrous benzene at 20-25°C is added a soln. tin-compd. in a 1:1 mole ratio, the reaction mixt. is left for 12 h; detected by IR-spectroscopy;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → barium stannate titanate

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → Ba(Ti0.88Sn0.12)O3

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → barium stannate titanate

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → Ba(Ti0975Sn0.025)O3

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → barium stannate titanate

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

tetrabutoxytitanium + barium(II) acetate (543-80-6) + dibutyltin dilaurate (77-58-7) → Ba(Ti0.95Sn0.05)O3

Conditions	Yield
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C;
With acetic acid In ethanol soln. of C32H64O4Sn and CH3COOH added to Ti(OC4H9)4 with costant stirring for 30 min; Ba(CH3COO)2 added with constant stirring for 30 min; kept at 70°C for 24 h; calcined at 750,800,850,900,and 1000°C; ground in ball mill, 12h; dried...;

2-Isocyanatoethyl methacrylate (30674-80-7) + C35H98O14Si13 + dibutyltin dilaurate (77-58-7) → C42H107NO17Si13

Conditions	Yield
In dichloromethane for 48h;

Upstream product

• 143-07-7 lauric acid 
• 818-08-6 di(n-butyl)tin oxide 
• 125610-44-8 Bu₂Sn(CH₂CH₂OCO-n-C₁₁H₂₃)2 
• 683-18-1 dibutyltin chloride 

Downstream Products

• 161678-38-2 octakis(3-chloropropyl)octasilsesquioxane 
• 7440-31-5 tin 

Relevant articles and documents

Synthesis method of dibutyltin dilaurate

The invention discloses a synthesis method of dibutyltin dilaurate. The method comprises steps as follows: 1, a solid mixture of lauric acid and dibutyltin oxide is stirred at the temperature of 20-30 DEG C to be converted into a liquid mixture; 2, the liquid mixture is heated to 60-70 DEG C and then subjected to a reflux reaction for 2-3 h; 3, the liquid mixture subjected to the reflux reaction is cooled to 10-30 DEG C, left to stand for layering and then collected, an organic phase is obtained, anhydrous magnesium sulfate is added to the organic phase for water removal, the mixture is filtered, and obtained filtrate is dibutyltin dilaurate. The solid mixture of lauric acid and dibutyltin oxide is converted into the liquid mixture, then the liquid mixture is subjected to the reflux reaction, cooled, separated and dried, and dibutyltin dilaurate is obtained. The process is simple, requirements for equipment are lower, the method takes short time and is convenient, efficient and environment-friendly, and the obtained dibutyltin dilaurate has no solvent or catalyst residues.

PROCESS FOR PRODUCTION OF ALKYL TIN ALKOXIDE COMPOUND, AND PROCESS FOR PRODUCTION OF CARBONATE ESTER USING THE COMPOUND

The present invention provides a process for producing : a compound represented by XOR2; a dialkyl tin dialkoxide compound having one tin atom, two Sn-R1 bonds and two Sn-OR2 bonds; and/or a tetraalkyl dialkoxy distannoxane compound having one Sn-O-Sn bond, in which each tin atom of the tetraalkyl dialkoxy distannoxane compound has two Sn-R1 bonds and one Sn-OR2 bond, the process comprising reacting in the absence of a catalyst at least one alkyl tin compound selected from the group consisting of i) and ii) below: i) a dialkyl tin compound having one tin atom, two Sn-R1 (wherein R1 represents an alkyl group) bonds, and two Sn-OX bonds (wherein OX is a group in which HOX that is a conjugate acid of OX is a Bronsted acid having a pKa of from 0 to 6.8); and ii) a tetraalkyl distannoxane compound having one Sn-O-Sn bond, in which each tin atom of the tetraalkyl distannoxane compound has two Sn-R1 bonds and one Sn-OX bond (wherein OX is a group in which HOX that is a conjugate acid of OX is a Bronsted acid having a pKa of from 0 to 6.8); and a carbonic acid ester represented by R2OCOOR2 (wherein R2 represents a linear or branched, saturated or unsaturated hydrocarbon group, a hydrocarbon group having a saturated or unsaturated cyclic hydrocarbon substituent, or a Y-CH2- group (wherein Y represents an alkyl polyalkylene group, an aromatic group or a cyclic saturated or unsaturated alkylene ether group)), and/or an alcohol represented by R2OH (wherein R2 is the same as defined above).