111-17-1

Basic information

• Product Name: 3,3'-Thiodipropionic acid
• Synonyms: 3,3'-THIODIPROPIONIC ACID;3,3-THIODIPROPIONIC ACID;3,3'-THIODIPROPIONIC ACID, POLYMER-BOUND;LABOTEST-BB LT00254336;DIETHYL SULFIDE 2,2'-DICARBOXYLIC ACID;BIS(2-CARBOXYETHYL) SULFIDE;Dimethyl sulfide 2,2-dicarboxylic acid;3,4'-Thiodipropionic acid
• CAS NO: 111-17-1
• Molecular Formula: C₆H₁₀O₄S
• Molecular Weight: 178.21
• EINECS: 203-841-3
• Product Categories: Others;Supported Reagents;Supported Synthesis
• Mol File: 111-17-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 280.43°C (rough estimate)
• Flash Point: 128 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1.238 (estimate)
• Vapor Pressure: 0.004Pa at 25℃
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 40g/l
• PKA: pK1:4.085;pK2:5.075 (18°C)
• Water Solubility: 40 g/L (25 ºC)
• Merck: 14,9332
• BRN: 1210299
• CAS DataBase Reference: 3,3'-Thiodipropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Thiodipropionic acid(111-17-1)
• EPA Substance Registry System: 3,3'-Thiodipropionic acid(111-17-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36-37/39-24/25
• WGK Germany: 2
• RTECS: UF7990000
• TSCA: Yes
• Hazardous Substances Data: 111-17-1(Hazardous Substances Data)

Usage

Chemical Properties

3,3'-Thiodipropionic acid is WHITE FINE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 111-17-1 differently. You can refer to the following data:
1. Antioxidant in food packaging, soaps, plasticizers, lubricants, fats, and oils.
2. 3,3'-Thiodipropionic acid is an antioxidant used to prevent fats and oils from going rancid. It has the same functionality as bha, bht, and propyl gallate.
3. 3,3'-Thiodipropionic acid is used as an antioxidant for fats and other foodstuffs.

Definition

3,3'-Thiodipropionic acid is a dicarboxylic acid.

Hazard

Use in foods restricted to 0.02% of fat and oil content, including essential oils.

Flammability and Explosibility

Notclassified

Safety Profile

A poison by intraperitoneal andintravenous routes. Moderately toxic by ingestion. A skinand eye irritant. When heated to decomposition it emitstoxic fumes of SOx.

Purification Methods

Crystallise the sulfide from water. [Beilstein 3 IV 735.]

Synthetic route

acrylic acid (79-10-7) → 4-thiaheptane-1,7-dioic acid (111-17-1) + 3-mercaptopropionic acid (107-96-0)

Conditions	Yield
Stage #1: acrylic acid With sodium hydroxide In water at 45 - 50℃; for 0.5h; Stage #2: With hydrogen sulfide In water at 45 - 100℃; Concentration; Time;	A n/a B 94.4%
Stage #1: acrylic acid With sodium hydroxide In water at 45 - 50℃; for 0.5h; Stage #2: With hydrogen sulfide In water at 45 - 100℃; for 9.46h; Stage #3: With sulfuric acid; iron In water for 2.5h; Concentration; Reagent/catalyst; Inert atmosphere;

3,3'-sulfinyldipropionic acid (3680-08-8) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With silica bromide In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	94%

3,3'-thiobis-propanenitrile (111-97-7) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With water for 48h; Rhodococcus rhodochrous AJ270;	60%
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 48h;	60%
With hydrogenchloride

β-Propiolactone (57-57-8) + 3-mercaptopropionic acid ethyl ester (5466-06-8) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With sodium hydroxide at 10℃; folgende Verseifung in der Siedehitze;

β-Propiolactone (57-57-8) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With sodium sulfide; water at 200℃;

β-Propiolactone (57-57-8) → 4-thiaheptane-1,7-dioic acid (111-17-1) + 3-mercaptopropionic acid (107-96-0)

Conditions	Yield
With sodium sulfide; water

3-iodopropanoic acid (141-76-4) → 4-thiaheptane-1,7-dioic acid (111-17-1) + 3-mercaptopropionic acid (107-96-0)

Conditions	Yield
With potassium hydrosulfide
With alkali hydrosulfide

3,3'-sulfinyldipropionic acid (3680-08-8) + mercaptoacetic acid (68-11-1) → 4-thiaheptane-1,7-dioic acid (111-17-1) + disulfanediyldiacetic acid (505-73-7)

Conditions	Yield
at 60℃; Rate constant;

acrylonitrile (107-13-1) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With potassium hydroxide; hydrogen sulfide at 15 - 25℃; folgende Verseifung mit verduennter Natronlauge bei 65grad;

acrylic acid methyl ester (292638-85-8) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With hydrogenchloride

acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With aqueous alkali
With sulfuric acid; acetic acid; hydroquinone

acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1) + tris-(2-carboxy-ethyl)-sulfonium ; chloride (39669-77-7)

Conditions	Yield
With hydrogenchloride; water; acetic acid

acrylic acid (79-10-7) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With sodium sulfide; water pH 9;

β-Propiolactone (57-57-8) + water (7732-18-5) + sodium hydrogensulfide → 4-thiaheptane-1,7-dioic acid (111-17-1) + 3-mercaptopropionic acid (107-96-0)

sulfuric acid (7664-93-9) + acetic acid (64-19-7) + hydroquinone (123-31-9) + acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1)

3-mercaptopropionic acid (107-96-0) + acrylic acid (2 mol) → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
in neutraler oder schwach mineralsaurer wss. Loesung;

acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) + alkali → 4-thiaheptane-1,7-dioic acid (111-17-1)

3-mercaptopropionic acid (107-96-0) + HCl 5n → 4-thiaheptane-1,7-dioic acid (111-17-1)

piperidine (110-89-4) + water (7732-18-5) + hydroquinone (123-31-9) + acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1) + (+/-)-2-methyl-3-thia-adipic acid (52662-37-0)

hydrogenchloride (7647-01-0) + acetic acid (64-19-7) + hydroquinone (123-31-9) + acrylic acid (79-10-7) + 3-mercaptopropionic acid (107-96-0) → 4-thiaheptane-1,7-dioic acid (111-17-1) + tris-<2-carboxy-ethyl>-sulfonium-chloride

hydrogenchloride (7647-01-0) + acetic acid (64-19-7) + 3-mercaptopropionic acid (107-96-0) + acrylic acid (3 mol) → 4-thiaheptane-1,7-dioic acid (111-17-1) + tris-<2-carboxy-ethyl>-sulfonium-chloride

β-iodo-propionate sodium → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With sodium sulfide

sodium-salt of/the/ 3-bromo-propionic acid + disodium-salt of/the/ 3-mercapto-propionic acid → 4-thiaheptane-1,7-dioic acid (111-17-1)

Conditions	Yield
With water

hydrogenchloride (7647-01-0) + 3,3'-thiobis-propanenitrile (111-97-7) → 4-thiaheptane-1,7-dioic acid (111-17-1)

3,3'-sulfinyldipropionic acid (3680-08-8) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → 4-thiaheptane-1,7-dioic acid (111-17-1)

hydrogenchloride (7647-01-0) + methyl 3-(methylthio)propionate (13532-18-8) → 4-thiaheptane-1,7-dioic acid (111-17-1) + dimethylsulfide (75-18-3)

hydrogenchloride (7647-01-0) + 3-(methylthio)propanoic acid ethyl ester (13327-56-5) → 4-thiaheptane-1,7-dioic acid (111-17-1) + dimethylsulfide (75-18-3)

methyl 3-(methylthio)propionate (13532-18-8) + sulfuric acid (7664-93-9) → 4-thiaheptane-1,7-dioic acid (111-17-1) + dimethylsulfide (75-18-3)

hydrogenchloride (7647-01-0) + 3-(methylsulfanyl)propionic acid (646-01-5) → 4-thiaheptane-1,7-dioic acid (111-17-1) + methylthiol (74-93-1) + dimethylsulfide (75-18-3)

4-thiaheptane-1,7-dioic acid (111-17-1) → 3,3'-sulfinyldipropionic acid (3680-08-8)

Conditions	Yield
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.0333333h; Reagent/catalyst;	99%
With dihydrogen peroxide at 20℃; for 0.0166667h; Reagent/catalyst;	98%
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.0166667h; Reagent/catalyst; chemoselective reaction;	98%

4-thiaheptane-1,7-dioic acid (111-17-1) + (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine (138500-88-6) → C19H28BNO5S

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride for 36h;	98%

4-thiaheptane-1,7-dioic acid (111-17-1) + allyl alcohol (107-18-6) → diallyl 3,3'-thiodipropanoate (39557-51-2)

Conditions	Yield
toluene-4-sulfonic acid In toluene Heating;	93%
With toluene-4-sulfonic acid In toluene for 8h; Heating / reflux;	20 g

4-thiaheptane-1,7-dioic acid (111-17-1) + 1,10-Phenanthroline (66-71-7) + copper(II) nitrate trihydrate + water (7732-18-5) → [Cu2(μ2-tdp)(1,10-phenanthroline)4](NO3)2·2H2O

Conditions	Yield
With sodium hydroxide In ethanol at 80℃; for 2h;	92%

4-thiaheptane-1,7-dioic acid (111-17-1) + esculin (531-75-9) → aesculin thiodipropionic acid ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 40℃; for 4h; Temperature; Reagent/catalyst; Solvent; Sonication; Inert atmosphere;	89.03%
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 40℃; for 4h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	89.03%

4-thiaheptane-1,7-dioic acid (111-17-1) + 1,10-Phenanthroline (66-71-7) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) → {[Cu(μ3-tdp)(1,10-phenanthroline)]·2H2O}n

Conditions	Yield
Stage #1: 4-thiaheptane-1,7-dioic acid; water; copper(II) acetate monohydrate at 70℃; for 1h; Stage #2: 1,10-Phenanthroline In ethanol at 70℃; for 2h;	86%

methanol (67-56-1) + 4-thiaheptane-1,7-dioic acid (111-17-1) → Dimethyl 3,3'-thiodipropionate (4131-74-2)

Conditions	Yield
With sulfuric acid Heating;	85%
With sulfuric acid

2,6-Diaminopyridine (141-86-6) + 4-thiaheptane-1,7-dioic acid (111-17-1) → 1,3,5,13,15,17-hexaaza-6,12,18,24-tetraoxo-9,21-dithia-2,3,4:14,15,16-dipyridine cyclotetracosane (1120337-12-3)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85℃;	85%

4-thiaheptane-1,7-dioic acid (111-17-1) + 1-Hexadecanol (36653-82-4) → dihexadecyl 3,3'-thiodipropionate (3287-12-5)

Conditions	Yield
With Novozym 435 at 80℃; under 600.048 Torr; for 4h;	84%

4-thiaheptane-1,7-dioic acid (111-17-1) → 3,3'-sulfonyldipropanoic acid (6291-88-9)

Conditions	Yield
With dihydrogen peroxide In methanol at 40℃; for 1h; chemoselective reaction;	82%
With potassium permanganate
With water; bromine
With dihydrogen peroxide; acetic acid
With Oxone In tetrahydrofuran; water at 20℃; for 3h;

4-thiaheptane-1,7-dioic acid (111-17-1) + benzoguanamine (91-76-9) → 1,11(2,6)-ditriazina-2,10,12,20-tetraaza-3,9,13,19-tetraoxo-6,16-dithiacyclocosa-phan-1(4),11(4)-diphenyl (1198294-59-5)

Conditions	Yield
With hydrogenchloride In ethanol; water Heating;	82%

guanidine carbonate (593-85-1) + 4-thiaheptane-1,7-dioic acid (111-17-1) + neodymium(III) nitrate hexahydrate → guanidinium tris(thiodipropionato)neodymium(III) trihydrate

Conditions	Yield
Stage #1: guanidine carbonate; 4-thiaheptane-1,7-dioic acid; neodymium(III) nitrate hexahydrate In water pH=6.55; Stage #2: With nitric acid In water pH=4 - 4.5;	80.5%

4-thiaheptane-1,7-dioic acid (111-17-1) → β,β'-thiodipropionic acid dichloroanhydride (18733-39-6)

Conditions	Yield
With thionyl chloride In benzene Heating;	80%
With thionyl chloride In chloroform; N,N-dimethyl-formamide at 50℃; for 0.166667h;	80%
With thionyl chloride

4-thiaheptane-1,7-dioic acid (111-17-1) + ethanol (64-17-5) → diethyl 3,3'-thiobispropionate (673-79-0)

Conditions	Yield
With sulfuric acid Heating;	80%
With sulfuric acid for 4h; Reflux;

4-thiaheptane-1,7-dioic acid (111-17-1) + butan-1-ol (71-36-3) → dibutyl thiodipropionate (6975-31-1)

Conditions	Yield
With sulfuric acid Heating;	79%
With sulfuric acid
With toluene-4-sulfonic acid; benzene unter Entfernen des entstehenden Wassers;

4-thiaheptane-1,7-dioic acid (111-17-1) + thiosemicarbazide (79-19-6) → 5,5'-(thiobis(ethane-2,1-diyl))bis(1,3,4-thiadiazol-2-amine) (303065-25-0)

Conditions	Yield
With trichlorophosphate at 90℃; for 3h;	79%
With trichlorophosphate at 90℃; for 3h;	60%

[2,2]bipyridinyl (366-18-7) + 4-thiaheptane-1,7-dioic acid (111-17-1) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) → {[Cu(μ3-tdp)(2,2'-bipyridine)]·H2O}n (142576-33-8, 1574389-81-3)

Conditions	Yield
Stage #1: 4-thiaheptane-1,7-dioic acid; water; copper(II) acetate monohydrate at 70℃; for 1h; Stage #2: [2,2]bipyridinyl In ethanol at 70℃; for 2h;	79%

guanidine carbonate (593-85-1) + 4-thiaheptane-1,7-dioic acid (111-17-1) + praseodymium(III) nitrate hexahydrate → guanidinium tris(thiodipropionato)praseodymium(III) trihydrate

Conditions	Yield
Stage #1: guanidine carbonate; 4-thiaheptane-1,7-dioic acid; praseodymium(III) nitrate hexahydrate In water pH=6.55; Stage #2: With nitric acid In water pH=4 - 4.5;	78.1%

4-thiaheptane-1,7-dioic acid (111-17-1) + 1-octadecanol (112-92-5) → distearyl thiodipropionate (693-36-7)

Conditions	Yield
With sulfuric acid Heating;	78%

4-thiaheptane-1,7-dioic acid (111-17-1) + 1-(4-hydroxyphenylethynyl)-1,2,3,4,5-pentaphenyl-1H-silole → C90H66O4SSi2

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h;	78%

4-thiaheptane-1,7-dioic acid (111-17-1) + copper(II) perchlorate hexahydrate + N,N,N',N'',N'''-pentamethyldiethylenetriamine (3030-47-5) → [Cu2(N,N,N′,N″,N″-pentamethyldiethylenetriamine)2(H2O)2(μ-tdpa)](ClO4)2*H2O

Conditions	Yield
With potassium hydroxide In methanol; water	77%

guanidine carbonate (593-85-1) + 4-thiaheptane-1,7-dioic acid (111-17-1) + samarium(III) nitrate hexahydrate → guanidinium tris(thiodipropionato)samarium(III) trihydrate

Conditions	Yield
Stage #1: guanidine carbonate; 4-thiaheptane-1,7-dioic acid; samarium(III) nitrate hexahydrate In water pH=6.55; Stage #2: With nitric acid In water pH=4 - 4.5;	76.7%

4-thiaheptane-1,7-dioic acid (111-17-1) + 1-dodecyl alcohol (112-53-8) → dilauryl thiodipropionate (123-28-4)

Conditions	Yield
With sulfuric acid Heating;	76%
With Novozym 435 at 80℃; under 600.048 Torr; for 24h;

4-thiaheptane-1,7-dioic acid (111-17-1) + hexan-1-ol (111-27-3) → dihexyl thiodipropionate (15206-58-3)

Conditions	Yield
With sulfuric acid Heating;	76%

4-thiaheptane-1,7-dioic acid (111-17-1) + 5-Hexen-1-ol (821-41-0) → C18H30O4S

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	76%

4-thiaheptane-1,7-dioic acid (111-17-1) + Trimethylenediamine (109-76-2) → 1,9,13,21-tetraaza-5,17-dithiacyclotetracosane-2,8,14,20-tetraone (1192661-22-5)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85℃; for 14h; pH=3 - 4;	75%

4-thiaheptane-1,7-dioic acid (111-17-1) + zinc(II) chloride (7646-85-7) → zinc thiodipropionate (18080-37-0)

Conditions	Yield
With Na2CO3 In water byproducts: CO2; under aerobic condns.; to aq. soln. of thiodipropionic acid, added Na2CO3; mixt. stirred, then soln. mixed with aq. ZnCl2; soln. stirred for 10 min; acetone added; left overnight at room temp.; crystals filtered off, washed with acetone and Et2O; dried in air; elem. anal.;	75%

4-thiaheptane-1,7-dioic acid (111-17-1) + C37H28OSi → C80H62O4SSi2

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h;	74%

Upstream product

• 57-57-8 β-Propiolactone 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 111-97-7 3,3'-thiobis-propanenitrile 
• 3680-08-8 3,3'-sulfinyldipropionic acid 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 646-01-5 3-(methylsulfanyl)propionic acid 
• 68-11-1 mercaptoacetic acid 
• 79-10-7 acrylic acid 
• 20986-22-5 (2-carboxyethyl)dimethylsulfonium bromide 
• 107-96-0 3-mercaptopropionic acid 
• 13532-18-8 methyl 3-(methylthio)propionate 
• 18673-13-7 3-ethylsulfanylpropionic acid methyl ester 

Downstream Products

• 4131-74-2 Dimethyl 3,3'-thiodipropionate 
• 111329-19-2 3,3'-sulfanediyl-di-propionic acid bis-(N'-phenyl-hydrazide) 
• 5459-10-9 thiodipropionic acid bis-amide 
• 57717-38-1 thiodipropionic acid di-[3-(3-tert.butyl-4-hydroxy-5-methylphenyl)-2,2-dimethylpropyl] ester 
• 693-36-7 distearyl thiodipropionate 
• 3006-27-7 dioctyl 3,3'-thiodipropionate 
• 673-79-0 diethyl 3,3'-thiobispropionate 
• 123-28-4 dilauryl thiodipropionate 
• 10595-09-2 3,3'-thiodipropanol 
• 56173-25-2 p-Nitrophenylthiodipropionat 
• 3680-08-8 3,3'-sulfinyldipropionic acid 
• 6291-88-9 3,3'-sulfonyldipropanoic acid 
• 17043-10-6 di(cis-9-octadecenyl) 3,3'-thiodipropionate 
• 3287-12-5 dihexadecyl 3,3'-thiodipropionate 

Relevant articles and documents

PROCESS FOR PREPARING ?-MERCAPTOCARBOXYLIC ACID

There is provided a process for preparing β-mercaptocarboxylic acid represented by the following General Formula (3) comprising step of reacting hydrogen sulfide, alkali hydroxide represented by a formula: XOH (X represents Na or K), and unsaturated carboxylic acid represented by the following General Formula (1) under atmospheric pressure to obtain a reaction solution including a compound represented by the following General Formula (2) and step of neutralizing the reaction solution in an acid. An amount of the alkali hydroxide is equal to or greater than total moles of the unsaturated carboxylic acid and the hydrogen sulfide.

A very useful and mild method for the deoxygenation of sulfoxide to sulfide with silica bromide as heterogeneous promoter

Silica bromide (SB) as heterogeneous reagent and promoter is prepared from reaction of silica gel with PBr3 as a non-hydroscopic, filterable, cheap, and stable yellowish powder that can be stored for months. The results show that the SB is suitable and efficient reagent for deoxygenation of sulfoxides to the corresponding sulfides under mild conditions at room temperature. The easy availability of this reagent makes this simple procedure attractive and a practical alternative to the existing methods.

Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270

Aliphatic dinitriles undergo regioselective hydrolysis with the title organism to give monoacids with up to four methylenes between the nitrile functions (optimally 2-3) or when either an oxygen is placed β, γ or δ to the nitrile (δ-placement being optimal) or β or γ (optimally γ) but not δ sulfur substituents are present; nitrogen substituents appear to behave as for oxygen but suffer a steric limitation of the size of the nitrogen substituent.