Download - Lab HIRA
Lab-HIRA: Hazard Identification and Risk Analysis for the
Chemical Research Laboratory
Dr. David LeggettLeggett Technical Consulting
Los Angeles, CA
243rd ACS National Meeting San Diego CA, March 2012
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A straightforward technique designed to identify and assess the hazards of conducting a chemical synthesis in the research environment.
Once hazards have been recognized appropriate risk minimization or mitigation measures can be implemented by the researcher.
An additional formal hazard analysis for the synthesis reaction may be recommended.
Lab-HIRA: Hazard Identification and Risk Assessment
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Lab-HIRA: Hazard Identification and Risk Assessment
• An explosion at Sussex University (UK, 1988) seriously injured a student. o UK H&SE prosecuted SU for negligence. o Today, British researchers are required to write down
risk assessments before every experiment.
• Univ. of California (Los Angeles), Texas Tech Univ. & Univ. of Florida have had well-publicized serious accidents in their chemistry labs
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Lab-HIRA: Hazard Identification and Risk Assessment
• Accident rate is 10 to 50 times higher than that in industrial laboratorieso In industry scientists are required to do a careful hazard
analysis and follow strict safety precautions
o Very few [academic] scientists have taken formal courses in safety, health, and toxicology
o Most relevant safety articles are published in journals devoted outside of an academics major field of interest
A.K. Furr, Handbook of Laboratory Safety (2000)
US Chemical Safety Board, Texas Tech University Laboratory Explosion Case Study (2010)
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Chemical Industry Typically Requires Hazards Testing for New Chemistry Destined for Full Scale Manufacture
Scale of Reaction Type of Hazard Assessment Typical Approaches
Research & Development
Desktop StudySmall Scale Testing
Calculations, Literature,DSC, Mixing Cal, RSST
Pilot or Kilo Lab Qualitative and Semi-Quantitative Testing
Reaction Calorimetry, Adiabatic Calorimetry
Manufacturing Custom testing for Engineering Design
DIERS, Dust, Reaction Calorimetry, Flammability
Lab-HIRA: Hazard Identification and Risk Assessment
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Lab-HIRA: Hazards Identification and Risk Analysis for New Chemistry at Research Scale
Desktop StudySmall Scale Testing
Calculations, LiteratureDSC, Mixing Calorimetry, RSST
SWIF or Simple HAZOP, if needed
Lab-HIRA: Hazard Identification and Risk Assessment
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Lab-HIRA uses the physical, chemical, and health data for reactants and reactions:• Flammability – vapors, liquids, solids
• Specific Chemical Hazards
• Health Data – toxicity, exposure, carcinogenicity
• Reaction Conditions
• Equipment such as radiation sources
Lab-HIRA Step 1: Hazard Identification
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Four Classes of Data Support Lab-HIRA
Class 1: Property Expressed as Specific Value
Class 2: Hazardous Characteristic of Molecule
Class 3: Reaction Hazards, by Type or Named Rxn
Class 4: Conditions of Synthesis
Lab-HIRA Step 1: Hazard Identification
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Properties Expressed as Discrete Values
Property Chemical / Energy Source Value
IDLH Hydrazine 50 ppm
LD50 (rats) 1,4-Dioxane 5,200 mg kg-1
TWA (OSHA) SO2 5 ppm
Flash Point THF -14 °C
Laser Source High intensity laser Class 4
Flammability Hexane Class IA
Lab-HIRA Step 1: Hazard Identification
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For discrete values, such as LD50, map values to an index scale 0 thru’ 4
United Nations, Globally Harmonized System of Classification and Labeling of Chemicals (2005)
Hazard Index Value Hazard Min Max
0 No Hazard > 5,000
1 Minimal > 500 5,000
2 Minor > 50 500
3 Moderate 5 50
4 Major < 5
Lab-HIRA Step 1: Hazard Identification
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Properties are expressed in various units:
PropertyHazard Index Value
0 1 2 3 4Flammability NF / NC IIIB II or IIIA IB or IC IA
Laser Source None Class 1 Class 2 Class 3 Class 4
UV Source, nm None 400-320 320-280 280-100 <100MIE, mJ > 5 2 - 5 0.5 - 2 0.05 - 0.5 < 0.05Auto-Ign, °C > 500 350 - 500 250 - 350 150 - 250 < 150Hazard No Haz Minimal Minor Moderate Major
Lab-HIRA Step 1: Hazard Identification
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Four Classes of DataClass 1: Property Expressed as Specific Value
Class 2: Hazardous Characteristic of Molecule
Class 3: Reaction Hazards, by Type or Named Reaction
Class 4: Conditions of Synthesis
Lab-HIRA Step 1: Hazard Identification
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Hazardous Characteristics of Molecules
Specific Hazard Index Code
Index Value
Pyrophoric: spontaneously flammable or reactive with air < 130 °F AIR 3
Forms gaseous products during reaction –CO2, CO, H2, N2, C4H10
GAS 2
Suspected carcinogen, teratogen, mutagen or reproductive hazard HLTH 4
Impact or friction sensitive IMPT 3
Molecule requires temperature controlled storage or handling TCN 2
Lab-HIRA Step 1: Hazard Identification
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Four Classes of DataClass 1: Property Expressed as Specific Value
Class 2: Hazardous Characteristic of Molecule
Class 3: Reaction Hazards, by Type or Named Rxn
Class 4: Conditions of Synthesis
Lab-HIRA Step 1: Hazard Identification
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Hazardous Characteristics of Molecules
Reaction Type Reaction Type Index Value
Decarboxylation Removal of –COOH with CO2 evolved 2
Nitration Red fuming or white HNO3, N2O4 3
ReductionsLiAlH4, N2H4 in KOH, NaBH4 in CH3OH 3
BF3 / NaBH4, H2 + catalyst 2
EsterificationsOxalyl chloride – high health hazard 3
RCOOH + SOCl2 followed by R’OH 2
Lab-HIRA Step 1: Hazard Identification
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Hazard Levels of Named Reactions
Reaction Type Reaction Type Index Value
Wolff-KishnerReduction
Reduction of RCHO or R2CO to RH with H2NNH2
3
Grignard Reaction Reaction of R’MgCl to RCHO or RR”CO to form RR’CHOH or RR’R”COH 3
Kochi Reaction One-carbon oxidative degradation of R-COOH using a Pb(IV) reagent 1
Meerwein-Ponndorf-VerleyReduction
The aluminum-catalyzed hydride shift from the α-carbon of an alcohol reagent to RR’CO forming RR’CHOH
2
Lab-HIRA Step 1: Hazard Identification
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Four Classes of DataClass 1: Property Expressed as Specific Value
Class 2: Hazardous Characteristic of Molecule
Class 3: Reaction Hazards, by Type or Named Reaction
Class 4: Conditions of Synthesis
Lab-HIRA Step 1: Hazard Identification
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Properties are expressed in various units:
Synthesis Conditions
Hazard Index Value0 1 2 3 4
TPROCESS, MAX (°C) < 75 75 - 150 150 -250 250 - 400 > 400
PPROCESS (psig) < 10 10 - 25 25 - 75 75 - 150 > 150
TFEED (°C) < 35 35 - 60 60 - 80 80 - 100 > 100
Scale-up Ratio 1 1 - 5 5 - 50 50 - 500 > 500
Reaction Mass (kg) < 0.005 0.005 – 0.1 0.1 - 1 1 - 5 > 5
Lab-HIRA Step 1: Hazard Identification
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Lab-HIRA compared to OSHA Lab Standard (29 CFR 1910.1450)
Health Properties: Lab-HIRA and 1910.1450
Physical and Chemical Properties: Lab-HIRA only
Reaction Conditions: Lab-HIRA only
Lab-HIRA Step 1: Hazard Identification
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Overall Hazard Index, OHI given by:
DIS_PR = Discrete property (LD50, Flash Pt.) mapped to range
DIS_CND = Discrete reaction condition (TRXN) mapped to range
CHM_HZ = Index value for specific chemical hazard (AIR, WAT)
NAME = Specific named reaction (Wolff-Kirshner)
TYPE = Type of reaction (Decarboxylation)
Lab-HIRA Step 1: Hazard Identification
TYPENAMECHM ︳HZDIS ︳CNDDIS ︳PRIVIVIVIVIVOHI
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Case Study 1: Diphenylmethane from Benzophenone, using Wolff-Kishner reaction:
Populate Lab-HIRA Chemical Hazard Review form for:• Benzophenone• Potassium hydroxide pellets• Hydrazine hydrate• Ethylene glycol
KOH, HOCH2CH2OH
H2NNH2 200 °C, Reflux
Lab-HIRA Step 1: Hazard Identification
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ACGIH TLVs
OSHA PEL & NIOSH IDLH
n/a Nuclear Radiation Type
5
B Pt
Dust Expl Severity: ST / Pmax / MIE
Lower Flam Limit
mg/kg
ST Dust Class n/a
Melting & Boiling Pt; AutoIgnition
Flammability (Liquid) LEL / UEL ; Fl Pt v/v%
113
Radiation Sources, Nuclear, Laser, UV
°C
ppm TWA (OSHA) n/a Exposure Limits
Toxicity LD50 oral (rat) 129
TWA (ACGIH) 40 ppm
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C (ACGIH) n/a
nmn/a UV WavelengthLaser Classn/a
ppm
ppm LC50 inhal Gas (rat)600
Upper Flam Limit
°C
AutoIgn Temp M Pt 270
7298
-52
Flash Point
mg/kg LD50 skin (rabbit) 570
°C
mJ
50
n/a n/a
Laser Type
IDLH (NIOSH)
°C
v/v%
Pmax psi Vapor MIE
ppmppm1PEL (OSHA)
STEL (ACGIH) 1 ppm
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Specific Hazard
Index Code Data for Hydrazine Index
Value
Flash Point FlPt 72 °C 2
Flam. Liquid FLAM Class IIIA 2
Explosion EXPL LFL = 5; UFL = 98 v/v% 4
Toxic Hazard TOXIC LD50 oral = 129mg kg-1; LC50 Inh = 570ppm; LC50 skin = 600mg kg-1 2
Exposure EXPOS IDLH = 50 ppm;PEL = 1ppm; TLV = 40ppm 4
AI Temperature AIT 270 °C 2
Fl. Pt vs BPt FPBP FlPt = 72 °C; BPt = 113 °C; Rxn T = 200 °C 2
Lab-HIRA Step 1: Hazard Identification
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FlPt 2 FLAM 2 EXPL 4 TOXIC 2 EXPOS 4
AIT 2 FPBP 2
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Severe A formal Risk Analysis MUST be performed for this chemical
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Repeat data entry for other reactants
Review results of Hazard Identification and Risk Analysis on Reaction Summary:
• Potentially Hazardous Reaction Conditions
• Summary of Hazard Properties of all Reagents
• Potentially Hazardous Reaction Chemistry
• Additional Concerns
• Recommendations for Additional Hazard Review
Lab-HIRA Step 1: Hazard Identification
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200 °C
25 °C
25 °C
0 psig
0 psig
Conversion of Existing Hazardous Functional Group (y/n)
1
y
Reaction performed less than 3 times (y/n)
Hazardous Functional Group Added to Molecule (y/n)n
n
Hazard Rating for Reaction Hazard
Maximum pressure of feed Maximum pressure of reaction Maximum temperature of feed Minimum reaction temperature
Minor
Hazards of Reaction Conditions (Check all that apply)
y
Maximum reaction temperature Scale-up reaction? Enter scale-up factor (Default = 1) Reaction to be run unattended (y/n)
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Toxic ba
sed on
LC(D) 50 value
s for
Oral, Skin or Inh
alation
Expo
sure based
on TLV,
PEL, or IDL
H
Classification of Flammab
le or
Combu
stible Liqu
id
Minim
um Ignitio
n En
ergy
(Vap
or or G
as)
Autoignitio
n Hazard
TOXIC EXPOS FLAM MIE-V AIT
1 Hydrazine hydrate y y y n y2 Benzophenone y y n n n3 Potassium Hydroxide y n n n n4 Diethylene glycol y n y n y5
6
.
Check Safeguards Compliance
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The reduction of aldehydes and ketones to alkanes. Condensation of the carbonyl compound with hydrazine forms the hydrazone, and treatment with base induces the reduction of the carbon coupled with oxidation of the hydrazine to gaseous nitrogen, to yield the corresponding alkane. The Huang-Minlon modification removes water and excess hydrazine by distillation, using a Dean Stark distillation trap, so that he reaction temperature can rise to 200 C. This allows the use of the cheaper hydrazine hydrate in place of anhydrous hydrazine. The Clemmensen Reduction can effect a similar conversion under strongly acidic conditions, and is useful if the starting material is base-labile.
Wolff-Kishner Reduction
Named Reaction Hazard Rating
Hazard Rating for Named Reactions
Wolff-Kishner Reduction
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138 °C
25 °C
25 °C
0 psig
0 psig
Major
Toxic based on
LC(D) 50 values for
Oral, Skin or Inh
alation
Expo
sure based
on TLV,
PEL, or IDLH
Classification of Flammable or
Combu
stible Liqu
id
Minim
um Ignitio
n Energy
(Vapor or G
as)
Autoignition
Hazard
Explosive Va
por
Flash Po
int H
azard
Ionizing Radiatio
n (alpha, beta, gam
ma, X‐Ray)
Laser Sou
rce
(Class 1, 2, 3, or 4
)
UV Ra
diation Source
(100 to
400 nm)
Strong Oxidizer / Reducer
Static Sensitive
Easily Polym
erizes
Suspected Cancer, M
utagenic,
Birth Defects, Teratogenic Risk
Water re
active
Air Sensitive
Peroxide
Former
High Re
actio
n Ra
te
Impact / Friction Sensitive
Temp control needed for storage
Sensitizer
Second
ary Ru
naway Reaction(s)
Gas fo
rmed
during reactio
n
TOXIC EXPOS FLAM MIE-V AIT EXPL FlPt NUCL LASER UV RDOX STAT POLY HLTH WAT AIR PERX HIRR IMPT TCN SENS RUN GAS
1 Hydrazine hydrate y y y n y y y n n n y n n y n n n n n n y n n 28 Severe
2 Benzophenone y y n n n y n n n n n n n n n n n n n n y n n 8 Minor
3 Potassium Hydroxide y n n n n n n n n n n n n n y n n y n n n n n 9 Minor
4 Diethylene glycol y n y n y y y n n n n n n n n n n n n n n n n 7 Minor
5 No Hazard
6 No Hazard
7 No Hazard
8 No Hazard
9 No Hazard
10 No Hazard
Overall Hazard Ratings and Recommendations
SEVERE HAZARD: Consider substituting one or more reagents for less hazardous compounds. Perform a Risk Analysis focusing on reagent handling and use.
At least one reactant, or solvent, has a flash point 25 C, or lower, than the planned max reaction temperature (138 C)
NO HAZARD
MAJOR HAZARD: Perform a Risk Analysis focusing on the reactive chemistry and synthetic methods for this step
Additional Concerns
Maximum reaction temperature Scale-up reaction? Enter scale-up factor (Default = 1) Reaction to be run unattended (y/n) Reaction performed less than 3 times (y/n)
Standad Synthesis Protocols Followed? (Provide reference)
Named Reaction Hazard Rating
Hazardous Functional Group Added to Molecule (y/n)n
n
Hazard Rating for Reaction Hazard
Maximum pressure of feed Maximum pressure of reaction Maximum temperature of feed Minimum reaction temperature
No HazardHazard Rating for Reaction Classes Hazard Rating for Named Reactions Minimal
Hazards of Reaction Conditions (Check all that apply)
Name of Reviewer
Name of Chemist
Documentation for Hazard Review
3/2/1912
3/1/1912
y
Use Named Reactions Hazards
n
y
n
y n
COR
Wolff-Kishner Reduction
n
n
y
Use the named reactions hazards to evaluate the potential hazards
Lab-HIRA Hazard Assessments for Synthesis Step
Section 3: Hazard Ratings, Recommendations and Documentation for Lab-HIRA Review
Section 1: Named Reaction or Reaction Class and Reaction Conditions for Step 1 of the Diphenylmethane synthesis
Section 2: Summary Table of Reagents Used During Step 1 of the Diphenylmethane synthesis.
Chemical Hazards Score
and RatingRe
actio
n Temperature
> Flash Po
int
High Co
rrosivity
FPBP
Reaction Class Hazard Rating
Conversion of Existing Hazardous Functional Group (y/n)The reduction of aldehydes and ketones to alkanes. Condensation of the carbonyl compound with hydrazine forms the hydrazone, and treatment with base induces the reduction of the carbon coupled with oxidation of the hydrazine to gaseous nitrogen, to yield the corresponding alkane. The Huang-Minlon modification removes water and excess hydrazine by distillation, using a Dean Stark distillation trap, so that he reaction temperature can rise to 200 C. This allows the use of the cheaper hydrazine hydrate in place of anhydrous hydrazine. The Clemmensen Reduction can effect a similar conversion under strongly acidic conditions, and is useful if the starting material is base-labile.
1
y
Lab-HIRA © Copyright Leggett Technical Consulting 2008 - 2011. Version 4.5; Date November, 2011
Use of Hazardous Chemicals
Hazard Potential of Reaction Chemistry
Hazard Potential of Reaction Conditions
Date Form Completed
Date Form Reviewed
Rudolp Fittig
Ludwig Kirshner
Location of notes and other related documention for this hazard review
Check Safeguards Compliance
Use Named Reactions Hazards Wolff-Kishner Reduction
Use of Hazardous Chemicals
Hazard Potential of Reaction Chemistry
Hazard Potential of Reaction Conditions
Overall Hazard Ratings and Recommendations
SEVERE HAZARD: Consider substituting one or more reagents for less hazardous compounds. Perform a Risk Analysis focusing on reagent handling and use.
At least one reactant, or solvent, has a flash point 25 C, or lower, than the planned max reaction temperature (200 C)
MINOR HAZARD: No Additional Risk Analysis needed
MAJOR HAZARD: Perform a Risk Analysis focusing on the reactive chemistry and synthetic methods for this step
Additional Concerns
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Case Study 2:• Synthesis of a vinyldecane derivative using t-BuLi.
• Researcher was exposed to t-BuLi during a transfer.
• The nitrile gloves and synthetic sweater, worn by the researcher at the time of the accident, caught fire; the chemist was not wearing a lab coat at the time.
• She received burns over 40% of her body and died a few weeks later.
How would Lab-HIRA have helped in this situation?
Lab-HIRA Step 1: Hazard Identification
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Lab-HIRA produces a Safeguards Com-pliance Checklist for each reagent, including PPE recommendations
13 Handling techniques for these chemicals have been reviewed and approved by Chemical Safety Committee Hazard Codes: AIR
14 Written contingency plans are available covering worst case accident scenarios Hazard Codes: WAT, AIR
Signed: ____________________________________ Print Name: ________________________________ Grad Student Post Doc Supervisor
Date: _________
Safeguards Required to Work With This Material Use
Safe-guard?(Y/N)
Describe other risk reduction measures
1 Confirm that only Class I Division 2 rated electrical equipment will be used during this synthesis
Hazard Codes: WAT, AIR, EXPL, FLAM
2 Consider using a glove box or bag to handle t-Bu Lithium
Hazard Codes: WAT, AIR
3 Material transfers will be done in the hood, glove box or bag. Open-bench work prohibited for this chemical
Hazard Codes: WAT, AIR, TCN
Lab-HIRA Step 1: Hazard Identification
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Lab-HIRA Step 2: Risk Assessment
Lab-HIRA may recommend a formal risk analysis such as a What-If or procedural HAZOP
• Chose the hazard analysis technique• Assemble necessary documentation• Conduct risk analysis• Evaluate recommendations for risk reduction• Close out recommendations
o Items to be completed before beginning worko Schedule other items for timely completion
• Document Lab-HIRA findings
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Lab-HIRA Step 2: Risk Assessment
A typical synthesis procedure for Case Study 1:In a suitable fume hood set up a nitrogen-purged multi-neck flask
equipped with an agitator, reflux condenser, Dean-Stark trap, and
temperature controller.
Suspend the ketone (85 g) in an alkylene glycol (~2 L).
Place the flask in a room temperature oil bath then add KOH (70 g).
Gradually add 80% solution of hydrazine hydrate (65 mL).
Heat the reaction mixture slowly heated to 200oC ………
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Lab-HIRA Step 2: Risk Assessment
Action: Install and set a temperature controller for reactor
What-If Scenario 1: Temperature controller incorrectly set up or fails
Consequence: Failure to control reaction temperature; possible runaway reaction; possible loss of containment
Risk Assessment: Major, if consequence plays out
Current Safeguards: Chemist monitors reaction regularly
Recommendation: Determine if runaway is possible; consider using redundant T controller if true
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Lab-HIRA Step 2: Risk Assessment
Action: Install and set a temperature controller for reactor
What-If Scenario 2: Runaway reaction occurs before evasive action can be taken?
Consequence: Probable loss of containment; possible fire/ explosion
Risk Assessment: Severe, if consequence plays out
Current Safeguards: None at present – no GS willing to camp out beside fume hood
Recommendation: Determine if runaway is possible; consider using redundant T controller if true; do not perform overnight runs for this reaction
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Lab-HIRA: Summary and Conclusions• Lab-HIRA identifies and assesses reaction hazards
and gives guidance about formal hazard review.
• Designed for use by chemists who have sufficient knowledge to safely handle the chemicals and the equipment planned for the synthesis.
• The hazard potential may be estimated from readily available physical, chemical, and health data.
• Thirty three parameters, indicative of one or more hazardous properties of molecules or synthesis conditions, are used to assess the reaction hazards.
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Lab-HIRA: Summary and Conclusions
• The risk-based assessments tend to be conservative.
• Once hazards have been recognized appropriate risk reduction measures can be implemented.
• If a formal hazard analysis for the synthesis reactions is indicated then techniques, such as Check-List, What-If, SWIF or HAZOP are available.
• Thermal hazards testing may be required to quantify the consequences of equipment upsets or procedural short-comings.
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Lab-HIRA: Summary and Conclusions
Only open literature data are used.Some hazards associated with thesynthesis reaction may be missed.
It is the responsibility of the user todetermine the adequacy of thehazard identification and riskanalysis of their synthesis.
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D. Leggett, Lab-HIRA: Hazard Identification and Risk Analysis for the Chemical Research Laboratory: Part 1. Preliminary Hazard Evaluation, J. Chem. Health & Safety, In pressDOI 10.1016/j.jchas. 2012.01.012
D. Leggett, Lab-HIRA: Hazard Identification and Risk Analysis for the Chemical Research Laboratory: Part 2. Risk Analysis of Laboratory Operations, J. Chem. Health & Safety, In pressDOI 10.1016/j.jchas.2012.01.013
Lab-HIRA: Publications