7575-23-7

Usage

Uses

Pentaerythritol Tetra(3-mercaptopropionate) can be used for additives for hair treatments.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H16O5S/c1-6(14)7(12)13-5-8(2-9,3-10)4-11/h6,9-11,14H,2-5H2,1H3

Synthetic route

Pentaerythritol (115-77-5) + 3-mercaptopropionic acid (107-96-0) → pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7)

Conditions	Yield
With dmap; thionyl chloride In 1,2-dichloro-ethane at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature;	98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20 - 40℃; Reagent/catalyst; Temperature;	88.81%
With toluene-4-sulfonic acid In toluene at 110℃;

Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9) + 3-mercaptopropionic acid (107-96-0) → pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7)

Conditions	Yield
toluene-4-sulfonic acid In water; toluene at 104 - 121℃; for 5h; Product distribution / selectivity; Heating / reflux;

Pentaerythritol (115-77-5) + 3-mercaptopropionic acid (107-96-0) → pentaerythritol tris(3-mercaptopropionate) (7539-04-0) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 130℃; for 9h; Dean-Stark; Inert atmosphere;	A 79 %Chromat. B 20 %Chromat.

Pentaerythritol (115-77-5) + Methyl 3-mercaptopropionate (2935-90-2) → pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7)

Conditions	Yield
With methanesulfonic acid at 80 - 85℃; for 6h; Temperature;	473 g

Limonene oxide (1195-92-2) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C57H92O12S4

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In chlorobenzene at 60℃; for 24h;	100%

maleiimide (541-59-3) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C33H40N4O16S4

Conditions	Yield
In ethanol at 45℃; for 12h;	95%

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + 1,2:3,4-di-O-isopropylidene-6-O-vinylsulfonyl-α-D-galactopyranose → C73H116O40S8

Conditions	Yield
With triethylamine; triphenylphosphine In dichloromethane; isopropyl alcohol at 20℃; for 48h; Michael Addition; Inert atmosphere;	93%

3-methacryloyloxyphenyl isocyanate (911390-20-0) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C61H64N4O20S4 (1008528-96-8)

Conditions	Yield
With dibutyltin dilaurate In dichloromethane for 7.75h;	90%

carbon disulfide (75-15-0) + Methyl 2-bromopropionate (5445-17-0) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → pentaerythritol tetrakis(3-(S-(1-methoxycarbonylethyl)trithiocarbonyl)propionate) (1190289-66-7)

Conditions	Yield
Stage #1: carbon disulfide; pentaerythritol tetrakis(3-mercaptopropionate) With triethylamine In dichloromethane at 20℃; for 1h; Stage #2: Methyl 2-bromopropionate In dichloromethane	88%

2-Isocyanatoethyl methacrylate (30674-80-7) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C45H64N4O20S4 (1008528-95-7)

Conditions	Yield
With dibutyltin dilaurate In toluene at 35℃; for 8h;	86%

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + C61H90N7O14(1+)*2F6P(1-)*H(1+) → C78H118N7O22S4(1+)*2F6P(1-)*H(1+)

Conditions	Yield
In acetonitrile for 1h; UV-irradiation;	79.2%

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + C63H92N7O15(1+)*F6P(1-) → C80H120N7O23S4(1+)*F6P(1-)

Conditions	Yield
In acetonitrile for 1h; UV-irradiation;	74.3%

carbon disulfide (75-15-0) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + benzyl bromide (100-39-0) → pentaerythritol tetrakis(3-(S-benzyltrithiocarbonyl)propionate) (303040-80-4)

Conditions	Yield
Stage #1: carbon disulfide; pentaerythritol tetrakis(3-mercaptopropionate) With triethylamine In chloroform at 20℃; for 1h; Stage #2: benzyl bromide In chloroform for 2h;	73%
Stage #1: carbon disulfide; pentaerythritol tetrakis(3-mercaptopropionate) With potassium phosphate In tetrahydrofuran for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran for 24h;	62%
With triethylamine In chloroform at 20℃;

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + (2R,3R,4R,5R,6S)-non-8-ene-1,2,3,4,5,6-hexaol → 2,2-bis(((3-(((4S,5R,6R,7R,8R)-4,5,6,7,8,9 hexahydroxynonyl)thio)propanoyl)oxy)methyl)propane-1,3-diylbis(3-(((4S,5R,6R,7R,8R)-4,5,6,7,8,9-hexahydroxynonyl)thio)propanoate)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; water for 1h; UV-irradiation;	73%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → 2,2',3,3',11,11',12,12'-octahydro-7,7'-spirobi[naphtho[2,3-j] [1,5,9,12]dioxadithiacyclopentadecin]-4,4',10,10',14,14',19,19'(6H,6'H,8H,8'H)-octaone (1347739-43-8)

Conditions	Yield
With triethylamine In chloroform for 4h;	57.5%

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + (S)-2-(pyridin-2-yldisulfanyl)ethyl 4-cyano-4-(((ethylthio)carbonothioyl)thio)pentanoate → C61H88N4O16S20

Conditions	Yield
With acetic acid In dichloromethane at 20℃; for 48h;	14%

Triethylene glycol divinyl ether (765-12-8) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): pentaerythritol tetra(3-mercaptopropionate); triethylene glycol divinyl ether

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 30h; UV-irradiation;

hexamethylene glycol diacrylate (13048-33-4) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): pentaerythritol tetra(3-mercaptopropionate); 1,6-hexanediol diacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 30h; UV-irradiation;

trimethylol propane diallyl ether (682-09-7) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): pentaerythritol tetra(3-mercaptopropionate); trimethylolpropane diallyl ether

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In various solvent(s) Kinetics; Irradiation;
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 30h; UV-irradiation;

1,6-hexanediol di(norborn-2-ene-5-carboxylate) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): pentaerythritol tetra(3-mercaptopropionate); 1,6-hexanediol di(norborn-2-ene-5-carboxylate)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 30h; UV-irradiation;

triallyl isocyanurate (1025-15-6) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; pentaerythritol tetra(3-mercaptopropionate)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; Kinetics; UV-irradiation;

hexane-1,6-diol dimethylacrylate + triallyl isocyanurate (1025-15-6) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → polymer; monomer(s): 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; pentaerythritol tetra(3-mercaptopropionate); hexane-1,6-diol dimethylacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; Kinetics; UV-irradiation;

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C17H27NO9S4

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + poly(ethylene glycol) diacrylate → poly(ethylene glycol) hexathiol

Conditions	Yield
With sodium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran; dichloromethane; water for 0.916667h;

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + poly(ethylene glycol) diacrylate → poly(ethylene glycol) tetraacrylate

Conditions	Yield
With sodium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran; dichloromethane; water for 0.5h;

pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) + m-xylylene diisocyanate (3634-83-1) → poly(pentaerythritol 3-mercaptopropionic ester-co-m-xylylene diisocyanate)

Conditions	Yield
With ZELEC UN; Viosorb 583; dibutyltin chloride at 10 - 120℃; for 18h; Product distribution / selectivity;
dithiocyanato tetramino cobalt tetraphenyl borate In 1-methyl-pyrrolidin-2-one for 0.0166667h; Reactivity; Irradiation;
acetato pentamino cobalt tetraphenyl borate In 1-methyl-pyrrolidin-2-one for 0.0166667h; Reactivity; Irradiation;

propargyl acrylate (10477-47-1) + pentaerythritol tetrakis(3-mercaptopropionate) (7575-23-7) → C41H52O16S4 (1148009-98-6)

Conditions	Yield
With hexan-1-amine for 1h; Michael reaction;
for 1h;
With hexan-1-amine at 20℃; for 1.03333h;

Upstream product

• 115-77-5 Pentaerythritol 
• 107-96-0 3-mercaptopropionic acid 
• 126-58-9 Dipentaerythritol 
• 2935-90-2 Methyl 3-mercaptopropionate 

Downstream Products

• 303040-80-4 pentaerythritol tetrakis(3-(S-benzyltrithiocarbonyl)propionate) 
• 1287759-43-6 2,2-bis(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) 
• 1008528-96-8 C₆₁H₆₄N₄O₂₀S₄ 

Relevant academic research and scientific papers

Method for preparing pentaerythritol tetra (3-mercaptopropionic acid) ester

The invention relates to the field of chemical synthesis, in particular to a method for preparing pentaerythritol tetra (3-mercaptopropionic acid) ester, the method comprises the following steps: using dichloromethane as a solvent, N, N '-dicyclohexylcarbodiimide (DCC) as a water-carrying agent and 4-dimethylaminopyridine (DMAP) as a catalyst, carrying out esterification reaction on pentaerythritol by using 3-mercaptopropionic acid to obtain pentaerythritol tetra (3-mercaptopropionic acid) ester; the preparation method is simple in process, easily available in raw materials, high in added value of products and suitable for industrial production.

Preparation method of high-content pentaerythritol tetra (3-mercaptopropionic acid) ester

The invention belongs to the field of chemical industry, and particularly relates to a preparation method of high-content pentaerythritol tetra (3-mercaptopropionic acid) ester, and the method comprises the following steps: reacting pentaerythritol, mercaptopropionic acid and an acylating reagent as raw material and organic alkali as a catalyst in a certain solvent at a certain temperature, and finally carrying out alkali washing, acid washing, water washing and negative pressure solvent recovery to obtain the target product. The preparation method disclosed by the invention has the advantagesof high reaction rate, low product chromaticity, small smell, high main content and the like.

Novel synthesis method of pentaerythritol tetra(3-mercaptopropionate)

The invention belongs to the field of chemical technology synthesis, and concretely relates to a synthesis method of pentaerythritol tetra(3-mercaptopropionate). Pentaerythritol reacts with 3-mercaptopropionic acid under the action of a catalyst silicon sulfonic acid to obtain the pentaerythritol tetra(3-mercaptopropionate). The silicon sulfonic acid is adopted as the catalyst, so that the esterification efficiency can be greatly improved, the reaction time is shortened, the energy consumption is reduced, the impurity content of the obtained product is low, and the post-treatment steps are greatly simplified; and the catalyst can be recycled, so the method is suitable for industrial production.

Preparation method of pentaerythritol mercaptocarboxylate

The invention discloses a preparation method of pentaerythritol tetra (3-mercaptopropionate). According to the preparation method, methyl mercaptopropionate and pentaerythritol are used as raw materials for catalytic reaction to obtain the product pentaerythritol tetra (3-mercaptopropionate), and the problems of low reaction speed, many side reactions and inevitable generation of impurity A in theprior art are solved. The preparation method is high in reaction speed, side reactions are reduced, and the content of impurities in the product is reduced.

POLYTHIOL COMPOSITION FOR A PLASTIC OPTICAL LENS

The embodiments relate to a polythiol composition for a plastic optical lens and a polythiourethane-based plastic optical lens prepared therefrom. In the embodiments, a first polythiol compound having an ester group and a mercapto group only as a hydrogen-bondable functional group and a second polythiol compound having an ester group and a hydrogen-bondable functional group other than a mercapto group are used in an appropriate amount. Thus, it is possible to control the viscosity of a polymerizable composition at the initial stage of polymerization at a low temperature of 5 to 15℃ and to stabilize the rate of increase in the viscosity of the composition and the reaction rate thereof, thereby preventing the generation of striae, bubbles, and the like. Further, various plastic lenses such as eyeglass lenses, camera lenses, and the like having excellent appearance characteristics (without striae and bubbles) and excellent optical characteristics can be obtained from the composition.

PROCESS FOR PRODUCING PENTAERYTHRITOL MERCAPTOCARBOXYLIC ACID ESTER, POLYMERIZABLE COMPOSITION, RESIN, OPTICAL MATERIAL, AND LENS

A process for producing a pentaerythritol mercaptocarboxylic acid ester of the present invention includes: a step of reacting pentaerythritol with a mercaptocarboxylic acid, in which an absorbance of a 5 wt % aqueous solution of the pentaerythritol at a wavelength of 270 nm, which is measured using a quartz cell having an optical path length of 50 mm, is 0.07 or less.

METHOD FOR PRODUCING 3-MERCAPTOPROPIONIC ACID, AND METHODS USING SAME FOR PRODUCING CARBOXYLIC ACID ESTER COMPOUND HAVING MERCAPTO GROUP AND THIOURETHANE-BASED OPTICAL MATERIAL

A method for producing 3-mercaptopropionic acid and methods using same for producing a carbonic acid ester compound having a mercapto group and a thiourethane-based optical material. The present invention improves a process during the production of 3-mercaptopropionic acid, significantly increases yield, and reduces the temperature and time during vacuum distillation, thereby preventing the destruction of a product and significantly increasing productivity. The present invention allows high-purity 3-mercaptopropionic acid having an excellent color to be finally yielded; accordingly, by using same, a high-purity carbonic acid ester compound having an excellent color and a mercapto group can be inexpensively obtained. A thiourethane-based polymeric composition and a thiourethane-based optical material obtained by polymerizing same can likewise be inexpensively obtained by using said carbonic acid ester compound. Such carbonic acid ester compound can be used for the production of inexpensive thiourethane optical lenses; consequently, inexpensive optical lenses having an excellent color can be obtained.

PURIFICATION METHOD OF THIOL COMPOUND, AND MANUFACTURING METHOD OF THIOL COMPOUND

PROBLEM TO BE SOLVED: To provide a purification method of a thiol compound capable of easily conducting removal of acidic impurities containing a sulfur element from the thiol compound, and applicable to manufacturing in an industrial scale. SOLUTION: The purification method of a thiol compound is a method for purifying the thiol compound obtained by a reaction using an acidic compound containing a sulfur element as a catalyst, and includes a process for mixing the thiol compound and an inorganic compound containing at least one kind selected from a group consisting of layered double hydroxide represented by the following formula (1) and zinc oxide, and a process for separating the inorganic compound from a mixture obtained in the mixing process. (M1)1-x(M2)x(OH)2(An-)x/n mH2O (1), where M1 represents at least one kind selected from a group consisting of Zn, Mg, Fe and Ca, and at least a part is Zn, M2 represents at least one kind element selected from a group consisting of Al and Fe, An- represents n-valent interlayer anion, x and n are numbers satisfying conditions 0.2≤x≤0.4, 1≤n≤4 respectively, and m is the number of 0 or more. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Preparing method for multi-mercapto carboxylic ester

The invention provides a preparing method for multi-mercapto carboxylic ester. The preparing method comprises the steps that mercapto carboxylic acid and polyhydric alcohol react under the conditions that the pressure intensity is smaller than or equal to -0.07 MPa and the temperature ranges from 80 DEG C to 100 DEG C, and multi-mercapto carboxylic ester is obtained. According to the preparing method, the esterification reaction of mercapto carboxylic acid and polyhydric alcohol is carried out under the conditions of the high temperature and negative pressure, and a water-carrying agent is not needed, so that a series of problems brought by the water-carrying agent are solved, the loss of the water-carrying agent is avoided, the reaction speed is increased, and meanwhile the product quality is improved.

Abrasion-resistant optical article and process for manufacturing thereof

Optical article comprising a transparent substrate and an abrasion-resistant layer appended to the at least one surface of said substrate, wherein said abrasion-resistant layer results from the reaction mixture of the following compounds: - a first organo-silane chosen from thiocarbamate-silane matrix precursor containing at least one terminal alkoxysilane group, or hydrolysates thereof, - an inorganic oxide selected from the group consisting of silica, iron, titanium, cerium, zirconium, antimony, zinc, tin oxides, and composite oxides thereof, - a curing catalyst for said thiocarbamate-silane, and - a solvent for said organo-silane. The invention also relates to a process for manufacturing said articles, and to the use of the above-mentioned article for the manufacturing of optic glasses or lenses.