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Triphenyl phosphite

HCID 7540
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Basic information

CAS
101-02-0
Standard SMILES
c1ccc(OP(Oc2ccccc2)Oc2ccccc2)cc1
InChIKey
HVLLSGMXQDNUAL-UHFFFAOYSA-N
Molecular formula
C18H15O3P
Average molar mass
310.3 g/mol
Monoisotopic mass
310.07588097

Overview

Triphenyl phosphite is a clear, pale yellow liquid with a clean, pleasant odor. (NTP, 1992)

Names & identifiers

Preferred name
Triphenyl phosphite
IUPAC
triphenyl phosphite
English name
Triphenyl phosphite
Molecular formula
C18H15O3P
Molecular weight
310.28

Names & synonyms

TRIPHENYL PHOSPHITE101-02-0Phosphorous acid, triphenyl esterTriphenoxyphosphinePhenyl phosphiteAdvance TPPTris(phenoxy)phosphineSumilizer TPP-RTrifenoxyfosfinTrifenylfosfitStabilizer P 36Phosclere T 36
Show more names
TPOP(OPh)3(PhO)3Pp36P 36SK28jp360
EFEDMellite 310P 36 (stabilizer)Sumilizer TTP-RWeston TPPTPP (plasticizer)ADK Stab TPPTP 1 (plasticizer)

Database identifiers

CAS
101-02-0
PubChem CID
7540
DTXSID
DTXSID0026252
ChEMBL
CHEMBL1875503
UNII
9P45GRD24X
EC Number
202-908-4
Nikkaji
J3.594G

Properties

Computed structural properties

XLogP
5.5
Topological polar surface area
27.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
22
Formal charge
0
Complexity
247

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phosphite Compounds
Polymers · 3 items

Plastics -> PVC (soft); PVC (rigid)

Plastics -> Heat stabilisers

Plastics -> Other functions -> Other stabiliser

SpringerMaterials PropertiesChemical shift
OdorPleasant odor
Density · 4 items

1.1844 at 68 °F (NTP, 1992) - Denser than water; will sink

1.1842 @ 20 °C

Relative density (water = 1): 1.18

1.184 @25 °C

Color/FormWater-white to pale yellow solid or oily liquid
Solubility · 3 items

less than 0.1 mg/mL at 68 °F (NTP, 1992)

Insoluble in water. Very soluble in ethanol, organic solvents.

Solubility in water: none

Flash Point · 3 items

425 °F (NTP, 1992)

425 °F (218 °C) (OPEN CUP)

218 °C o.c.

Boiling Point · 3 items

680 °F at 760 mmHg (NTP, 1992)

360 °C

360 °C

DecompositionWhen heated to decomp ... emits toxic fumes of /phosphorus oxides/.
Melting Point · 3 items

72 to 75 °F (NTP, 1992)

25 °C

22-25 °C

Vapor Density>1 (air = 1)

Physicochemical properties

Melting point
22 · 22-24 °C (lit.)
Boiling point
360 °C · 360 °C (lit.)
Density
1.184 g/mL · 1.184 g/mL at 25 °C (lit.)
vapor density
10.7 · 10.7 (vs air)
vapor pressure
5 mm · 5 mm Hg ( 205 °C)
refractive index
20 · n20/D 1.59(lit.)
Flash point
425 °F · 425 °F
storage temp.
30 °C · Store below +30°C.
solubility
25 mg/mL, · methanol: 25 mg/mL, clear
form
Liquid
color
Clear colorless to pale yellow
PH
1 · 1 (200g/l, H2O, 20℃)
Water Solubility
insoluble
Sensitive
Air & Moisture Sensitive
BRN
1079456 · 1079456
Henry's Law Constant
1.8 · 1.8×101 mol/(m3Pa) at 25℃, Zhang et al. (2010)
Dielectric constant
3.2 · 3.2(24℃)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
1S/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H
InChIKey
HVLLSGMXQDNUAL-UHFFFAOYSA-N
SMILES
O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3
Indirect Additives used in Food Contact Substances
TRIPHENYL PHOSPHITE
CAS DataBase Reference
101 · 101-02-0(CAS DataBase Reference)
EWG's Food Scores
1 · 1
NCI Dictionary of Cancer Terms
TPO
FDA UNII
9 P45GRD24X · 9P45GRD24X
NIST Chemistry Reference
Phosphorous acid, triphenyl ester(101-02-0)
EPA Substance Registry System
Triphenyl phosphite (101-02-0)
UNSPSC Code
12352108 · 12352108
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H410
Precautionary statements
501 · P501-P273-P270-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
target organs
Nervous system
Hazard Codes
Xn,N,Xi
Risk Statements
36 · 36/38-50/53
Safety Statements
28 · 28-60-61-28A-26
RIDADR
3077 · UN 3077 9/PG 3
WGK Germany
2 · 2
RTECS
1575000 · TH1575000
TSCA
TSCA listed
HazardClass
9 · 9
PackingGroup
III
HS Code
29209085 · 29209085
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT RE 2
Hazardous Substances Data
101 · 101-02-0(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 444mg/kg
REACH Registrations
Active
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (43.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Chemical: Phosphorous acid, triphenyl ester

Phosphorous acid, triphenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorous acid, triphenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14793

Triphenyl phosphite: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire Potential · 2 items

COMBUSTIBLE

COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME

Health Hazards · 1 item

SYMPTOMS: This compound exhibits symptoms similar to those caused by phenols: dizziness muscle weakness; dimness of vision; ringing in the ears; irregular and rapid breathing; weak pulse; shortness of breath. All these may be followed by loss of consciousness, collapse and death.

Hazards Summary · 1 item

Reacts with water; A skin, eye, and respiratory tract irritant; May cause skin sensitization; High concentrations may cause nervous system effects; [ICSC] An eye and severe skin irritant; A mild sensitizer; Emergency treatment: TOCP and related agents; Following exposure to >6-7 mg/kg of TOCP, patients have acute GI symptoms of vomiting, diarrhea and abdominal pain; After a delay of 8-35 days, patients develop peripheral neuropathy (flaccid paralysis) that resolves over the next 2-3 months in some patients; Some patients remain permanently paralyzed; [HSDB] Causes flaccid paralysis in rats after subcutaneous doses >2000 mg/kg; [RTECS] A skin irritant; [CAMEO] A skin and eye irritant; [eChemPortal: ESIS] An irritant; Harmful if swallowed; Toxic to aquatic organisms; [MSDSonline] See Triorthocresyl phosphate.

Reactive GroupSulfonates, Phosphonates, and Thiophosphonates, Organic
EC ClassificationSymbol: Xi, N; R: 36/38-50/53; S: (2)-28-60-61
Reactivity Profile · 1 item

Organophosphates, such as TRIPHENYL PHOSPHITE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Chemical DangersDecomposes on burning. This produces toxic fumes including phosphorus oxides. Reacts with strong oxidants. Reacts with water.
Air and Water ReactionsInsoluble in water.
NFPA Hazard Classification · 3 items

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Safety & protection

Fire Fighting · 2 items

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong oxidants. Well closed.
Fire Fighting Procedures · 2 items

To fight fire use, use /carbon dioxide/, mist, dry chemical.

WATER OR FOAM MAY CAUSE FROTHING.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 item

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Eye PreventionWear safety goggles or face shield.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 3 items

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

TSCA Test Submissions · 1 item

The ability of triphenyl phosphite to increase the incidence of micronucleated polychromatic erythrocytes was evaluated in the bone marrow of CD-1 mice. Based on preliminary toxicity determinations, three groups of mice (5/sex/group) were treated with total doses of 1250, 2500 and 5000mg/kg of test material as two equal oral administrations separated by an interval of 24 hours. Animals at the highest dose level experienced tremors and 5 mortalities. The incidence of micronucleated cells were analyzed in 1000 polychromatic erythrocytes per animal. The incidence of micronucleated polychromatic erythrocytes and the ratio of normochromatic to polychromatic erythrocytes were comparable to the vehicle control (corn oil).

Human Toxicity Excerpts · 3 items

...TRIPHENYLPHOSPHITE IS STRONG IRRITANT SUBSTANCE & MILD SENSITIZER.

...TRIPHENYL...PHOSPHITE ARE DELAYED NEUROTOXINS LACKING POTENT ANTI-CHOLINESTERASE PROPERTIES.

NONE OF THESE COMPD /PHOSPHATE & PHOSPHITE ESTERS/ PRODUCES TYPICAL SYMPTOMS ASSOCIATED WITH CHOLINESTERASE INHIBITION...

Non-Human Toxicity Excerpts · 5 items

...TRIPHENYL PHOSPHITE...PRODUCE/S/ TYPICAL FLACCID PARALYSIS IN CATS, DOGS, & MONKEYS

TREMORS, DIARRHEA, VASODILATATION BY ALL ROUTES; NO PARALYSIS IN SURVIVORS. INHIBITION OF CHOLINESTERASE IN WHOLE BLOOD IN MICE. SKIN & EYE IRRITANT. /FROM TABLE/

TRIPHENYL PHOSPHITE DID NOT SHOW IRRITATING OR RESORPTIVE EFFECTS WHEN APPLIED TO SKIN OF MICE, BUT CAUSED DERMATITIS WHEN APPLIED TO SKIN OF GUINEA PIGS; ALSO HAD SENSITIZING ACTION.

THRESHOLD DOSES CAUSING CHANGES IN FUNCTION OF RABBIT NERVOUS SYSTEM WAS 17 MG/KG FOR TRIPHENYL PHOSPHATE.

For more Non-Human Toxicity Excerpts (Complete) data for TRIPHENYL PHOSPHITE (7 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 2 items

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 m1/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Administer activated charcoal ... . If product was ingested, protect yourself from contact with vomitus as it may cause burns. /Phosphorus and related compounds/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload. Treat seizures with diazepam ... . Monitor for signs of hypoglycemia and administer 50% dextrose if necessary. Draw blood sample before administration ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phosphorus and related compounds/

Toxicity DataLC (rat) > 6,700 mg/m3/4h
Non-Human Toxicity Values · 3 items

LD50 MICE ORAL 1330 MG/KG

LD50 Rat oral 1600 mg/kg

LD50 Mouse ip 1167 mg/kg

Safety data

wgk
2
tsca
TSCA listed
rtecs
TH1575000
ridadr
UN 3077 9/PG 3
hs_code
29209085
Toxicity
LD50 oral in rat: 444mg/kg
risk_code
36/38-50/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N,Xi
safety_code
28-60-61-28A-26
hazard_class
9
Storage Class
10 - Combustible liquids
packing_group
III
target organs
Nervous system
Hazard statements
H302-H315-H319-H410
Limited Quantities
5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT RE 2
Precautionary statements
P501-P273-P270-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Hazardous Substances Data
101-02-0(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Metabolism/Metabolites...LIKELY THAT.../TRIPHENYL PHOSPHITE/ MAY BE HYDROLYZED READILY.
Absorption, Distribution and Excretion · 2 items

...(32)P-LABELED TRIPHENYL PHOSPHITE (0.3 ML/KG) IP IN CATS, INDICATED CONSIDERABLE HYDROLYSIS & ONLY SMALL AMT OF LABELED PHOSPHORUS IN CNS. ... PRESENCE OF SMALL CONCN OF PHOSPHOROUS ACID IN NERVOUS TISSUE MAY BE RELATED TO DEGENERATIVE CHANGES...

ABSORBED THROUGH GUINEA PIG SKIN. /FROM TABLE/

Uses & manufacturing

Uses · 6 items

Used as a stabilizer/antioxidant (rubber and plastics industries), metal scavenger, epoxy resin diluent, and insecticide synergist; [HSDB] Used as a reducing agent and in paints, lacquers, and varnishes; [IUCLID]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Chemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins.

ANTIOXIDANT FOR SYN RUBBERS

STABILIZER IN RUBBER & PLASTICS INDUSTRY

COLOR STABILIZER IN ALKYD RESINS

U.S. Production2023: 10,000,000 - <25,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesStabilizing agent
Methods of Manufacturing · 2 items

REACTION OF PHOSPHORUS TRICHLORIDE & PHENOL IN THE PRESENCE OF A TERTIARY AMINE

The commercial production method for triphenyl phosphite is believed to be based on the reaction of phenol and phosphorus trichloride in a moisture-free atmosphere.

Use Classification · 3 items

Plastics -> Polymer Type -> PVC (soft); PVC (rigid)

Plastics -> Heat stabilisers

Plastics -> Other functions -> Other stabiliser

General Manufacturing Information · 5 items

Synthetic Rubber Manufacturing

Phosphorous acid, triphenyl ester: ACTIVE

TRIPHENYL PHOSPHITE USED TO SYNTHESIZE HERBICIDE N-(O,O-DIPHENYLPHOSPHONOMETHYL)GLYCINE ETHYL ESTER.

TRIPHENYL PHOSPHITE DID NOT REACT WITH FERROUS CYTOCHROME P 450 & ITS DENATURED FORM, CYTOCHROME P 420, TO PRODUCE COMPLEXES HAVING 2 PEAKS IN SORET REGION OF OPTICAL DIFFERENCE SPECTRA.

TPP STRONGLY SYNERGIZED TOXICITY OF MALATHION & DIMETHOATE AGAINST RESISTANT GREEN LEAFHOPPER.

Applications · 5 items

Uses(1) Triphenyl phosphite is used as chelating agents, plastics antioxidant, alkyd resin and pesticide intermediate raw material. (2) It is used for synthetic rubber and resin stabilizer, PVC antioxidant, alkyd resin and pesticide intermediate raw material. (3) Triphenyl phosphite is used as secondary antioxidants, it has effect of light stability, it is suitable for polyvinyl chloride, polypropylene, polystyrene, polyester, ABS resin, and epoxy resin. (4) It is used as chelating agent in PVC products, it can enable products to maintain transparency, and suppresse color change. It can also be used for the production of trimethyl phosphite. (5) Antioxidants, stabilizers TPPi is mainly applied to polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyester, ABS resin, epoxy resin, synthetic rubber antioxidant stabilizer for PVC vinyl products as chelating agent, when the metal is as based stabilizer, coordinating with the product can reduce the harm of metal chloride (6) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (7) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (8) Chelating agent, it is widely used in all kinds of PVC products, it can enable products to maintain its transparency and suppress color change, and it can increase the antioxidant and light and heat stability of the primary stabilizer. In addition, the product is also used for PE, PP, ABS, SBS and other products, and it can be used for pesticide intermediates. It can be used for synthetic alkyd resins and polyester materials and polyester resins.

UsesTriphenyl phosphite (TPP) is the chemical compound with the formula P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes.

UsesStabilizer/antioxidant for vinyl plastics and polyethylene, polypropylene, styrene copolymers, and rubber.

UsesTriphenyl phosphite can be used:As a source of phosphorus and as a ligand for the synthesis of transition metal phosphide nanoparticles via heating-up process.To convert alcohols to alkyl halides.As a peptide coupling agent.As a low-temperature source of singlet oxygen after forming an adduct with ozone.To synthesize bromotriphenoxyphosphonium bromide, a brominating agent, by reacting with bromine.

UsesChemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins.

Upstream & downstream products

Upstream raw materials

PhenolPhosphorus trichloridePhosphorous acid, 2,6-diethylphenyl 2-ethylphenyl phenyl esterPhosphorous acid, 2,6-diethylphenyl diphenyl esterPhosphorous acid, 2,2-dimethylpropyl diphenyl esterPhosphorous acid, bis(2,2-dimethylpropyl) phenyl esterPhosphonic acid, methyl-, 2,2-dimethylpropyl phenyl ester (9CI)Phosphorous acid, 2-(1-methylethyl)phenyl diphenyl ester

Downstream products

polyester-based liquid crystalling ionmer containing sulfonate groupTetrachlorvinphosPhosphiteO,O'-Dioctadecylpentaerythritol bis(phosphite)Unsaturated polyester resinNeopentyl iodideTris(2-chloroethyl) phosphate3-Hydroxydiphenylaminebis(2-ethylhexyl) phenyl phosphiteTrimethyl phosphiteTriphenylphosphineScale inhibitorTriphenyl phosphate

Related reactions

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HRID 35837 reaction equation
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HRID 69579 reaction equation
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HRID 69606 reaction equation
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HRID 69612 reaction equation
HRID 69612As reactantuspto-grants-2014_09
HRID 69623 reaction equation
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HRID 69642 reaction equation
HRID 69642As reactantuspto-grants-2014_09
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