Encoding Reactive Chemical Hazards and Incompatibilities in an Alerting System. John May and Roger Sayle NextMove Software Cambridge, UK
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1 Encoding Reactive Chemical Hazards and Incompatibilities in an Alerting System John May and Roger Sayle NextMove Software Cambridge, UK
2 MOTIVATION (THE ALERTING SYSTEM) this talk
3 Reason, Primary Citations, Category
4 EVOLUTION OF HAZARD ALERTING 1. Chemical Compound (MSDS) Lookup a. Exact name/mfcd/synonym comparison b. Name-to-structure canonical match c. Normalised representation (InChI) match 2. Chemical Incompatibility Lookup 3. Substructure Patterns 4. Chemical Class Incompatibility 5. Reaction Mechanism Recognition (+ H2 Gas) 6. Physical Property Thresholds (BP,HoD,VP) Known Knowns Known Unknowns
5 HAZARD COMPATABILITY TIMELINE (INCOMPLETE) Bretherick's Handbook of Reactive Chemical Hazards (hazmatnavigator) 1980 A Method for Determining Hazardous Waste Compatibility (EPA) 1994 Cargo Compatibility Chart (USCG) 1998 New Program for Chemical Compatibility (NOAA) 2009 A Representative- Compound Approach to Functionality- Based Prediction of Reactive Chemical Hazards (NOAA) 2013 Enhanced NOAA chemical reactivity worksheet for determining chemical compatibility
6 1980 Hatayama HK et al. A Method for Determining Hazardous Waste Compatibility (EPA)
7 1994 Cargo Compatibility Chart, USCG 46 CFR part 150
8 CRW 3.0/CAMEO 1. Acetals, Ketals, Hemiacetals, and Hemiketals 2. Acid Halides, Sulfonyl Halides, and Chloroformates 3. Acids, Carboxylic 4. Acids, Strong Non-oxidizing 5. Acids, Strong Oxidizing 6. Acids, Weak 1. Acetals, Ketals, Hemiacetals, and Hemiketals 2. Acid Halides, Sulfonyl Halides, and Chloroformates Incompatible 3. Acids, Carboxylic Compatible Incompatible 4. Acids, Strong Non-oxidizing Caution Incompatible Incompatible 5. Acids, Strong Oxidizing Incompatible Incompatible Incompatible Incompatible 6. Acids, Weak Compatible Incompatible Compatible Caution Incompatible 7. Acrylates and Acrylic Acids Caution Caution Caution Incompatible Incompatible Caution 1998 J. Farr et al New Program for Chemical Compatibility Chemical Health and Safety 5
9 CAMEO: Computer- Aided Management of Emergency Operations
10
11 DESCRIBE COMPABILITIY MATRICES in XML? Encode in XML format ARE THEY APPLICABLE? Statistics on reaction corpus
12 CASANDRA 1.0 RULE EXPRESSIONS ContainsComponent Find a reactant by name (spelling corrected) chemical structure (Unique SMILES or InChI) quantity threshold and normalisation (e.g. > 10 g) role (e.g. solvent) ContainsPattern Find reactants that a SMARTS pattern hits Contains - enables indirection
13 Self Contained Implementation independent Facilitate exchange and reuse Flexible Arbitrarily complex expressions Meta- Information Description/Message Citation, Links Category Hierarchy
14 ENCODED Reactive GROUPS 3 Acids, Carboxylic 5 Aldehydes 6 Amides and Imides 7 Amines, Phosphines, and Pyridines 8 Azo, Diazo, Azido, Hydrazine, and Azide Compounds 9 Carbamates 11 Cyanides, Inorganic 12 Thiocarbamate Esters and Salts/Dithiocarbamate Esters and Salts 13 Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters 14 Ethers 17 Halogenated Organic Compounds 18 Isocyanates and Isothiocyanates 19 Ketones 20 Sulfides, Organic 21 Metals, Alkali, Very Acgve 22 Metals, Elemental and Powder, Acgve 23 Metals, Less Reacgve 26 Nitriles 27 Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic 30 Peroxides, Organic 31 Phenols and Cresols 32 Sulfonates, Phosphonates, and Thiophosphonates, Organic 34 Epoxides 35 Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes 37 Anhydrides 38 Salts, Acidic (dictonary list) 39 Salts, Basic (dictonary list) 40 Acid Halides, Sulfonyl Halides, and Chloroformates 42 Organometallics 44 Oxidizing Agents (dictonary list) 47 Fluorinated Organic Compounds 55 Chlorosilanes 58 Siloxanes 65 Conjugated Dienes 66 Aryl Halides 68 Amines, Aromagc 69 Nitrate and Nitrite Compounds, Inorganic 70 Acetals, Ketals, Hemiacetals, and Hemiketals 71 Acrylates and Acrylic Acids 72 Phenolic Salts 73 Quaternary Ammonium and Phosphonium Salts 74 Sulfite and Thiosulfate Salts 75 Oximes
15 REMAINING REACTIVE GROUPS Planned (17) 1 Acids, Strong Non- oxidizing 2 Acids, Strong Oxidizing 4 Alcohols and Polyols 10 Bases, Strong 16 Hydrocarbons, Aromagc 28 Hydrocarbons, Aliphagc Unsaturated 29 Hydrocarbons, Aliphagc Saturated 33 Sulfides, Inorganic 45 Reducing Agents 46 Non- Redox- Acgve Inorganic Compounds 51 Nitrides, Phosphides, Carbides, and Silicides 59 HalogenaTng Agents 60 Acids, Weak 61 Bases, Weak 62 Carbonate Salts 63 Alkynes, with Acetylenic Hydrogen 64 Alkynes, with No Acetylenic Hydrogen Difficult non- structural categories: 76 Polymerizable Compounds 98 Not Chemically Reacgve 99 Insufficient Informagon for Classificagon 100 Water and Aqueous Solugons 101 Highly Flammable 102 Explosive 103 Polymerizable 104 Strong Oxidizing Agent 105 Strong Reducing Agent 106 Known Catalygc Acgvity 107 Water- Reacgve 108 Air- Reacgve 109 Pyrophoric 110 Decomposes at Elevated Temperatures (<120 deg. C) 111 Peroxidizable Compound 400 Radioacgve Material
16 cameochemicals.noaa.gov/reactivity/ documentation/rg5-rg7
17 RULE HIERARCHY rg-5_7 (general) Aldehydes and Amines, Phosphines, and Pyridines rg-5_7* (specific) a. Acetaldehyde reacts violently with amines. b. Tertiary amines promote exothermic aldol condensations between aldehydes and/or ketones. c. Acrolein polymerizes explosively on contact with amines. a. Ethylenediamine may react violently with acrolein. b. Amines such as dimethylamine and triethylamine promote polymerization of acrolein.
18
19 COMPONENT EXPRESSIONS (2.0)
20 1,375 rules (18K lines) GENERAL COMBINATIONS semi- automatic 297 incompatible 191 caution SPECIFIC COMBINATIONS manual 744 incompatible 143 caution
21 1,566,049 USPTO REACTIONS US A1 [paragraph:943] H 3 C N + CH 3 O CH 3 N N N OH O + CH 3 N O O H 3 C N N N CH 3 N + + N F F F P F H N O H 3 C N CH 3 DMF O O CH 3 EtOAc N N O N O N F F N 4- (1- (4- cyanophenyl)- 1H- benzo[d]imidazol- 6- yl)benzoic acid (300 mg, 0.88 mmol) NMM (0.178 ml, 1.76 mmol) HATU (501 mg, 1.32 mmol) morpholine (0.84 ml, mmol) 4- (6- (4- (morpholine- 4- carbonyl)phenyl)- 1H- benzo[d]imidazol- 1- yl)benzonitrile (100 mg) nextmovesoftware.com/leadmine.html nextmovesoftware.com/blog/2014/02/
22 WARNINGS OVERVIEW 1,431,165 (91%) reactions flagged in 3h3m12s 7 ms avg per reactions (142 s - 1 ) 6,200,046 incompatibles 1,477,142 specific in 642,649 (41%) reactions 3,247,847 cautions 1,194,938 specific in 600,209 (38%) reactions
23 TOP 15 GENERAL INCOMPATIBILITIES Name rg 17_68 rg 6_68 rg 7_17 rg 3_68 rg 6_7 rg 8_17 rg 8_14 rg 9_17 rg 17_42 rg 3_7 rg 8_68 rg 14_42 rg 3_8 rg 42_66 rg 13_ Organic Halogens Amines, Arom Amides/Imides Amines, Arom Amines Organic Halogens COOH Amines, Arom Amides/Imides Amines Azo/Diazo/Azide Organic Halogens Azo/Diazo/Azide Ethers Carbamates Organic Halogens Organic Halogens Organometalics COOH Amines Azo, Diazo, Azide Amines, Arom Ethers Organometalics COOH Azo/Diazo/Azide Organometalics Aryl Halides Esters Metal Hydrides 0e+00 1e+05 2e+05 3e+05 4e+05 5e+05 n
24 TOP 15 SPECIFIC INCOMPATIBILITIES Name rg 7_13a rg 13_39a rg 5_7b rg 26_55a rg 19_21a rg 19_21b rg 40_68a rg 7_40a rg 3_39a rg 35_68b rg 7_35b rg 40_70i rg 26_55b rg 5_21b rg 35_68a Amines COOH Esters COOH Esters Amines Aldehydes/Ketones TerTary Amines Nitriles Halogens Ketones GI or GII Metal Ketones GI Metal Acyl Halides Amines, Arom Amines Acyl Halides COOH NaHCO Hydrides Amines, Arom Amines Metal Hydrides Acyl Halides Ethers Acetonitrile Halogens Na Aldehydes Organo- Li/Mg Amines, Arom 0e+00 2e+05 4e+05 6e+05 n
25 INFORMATION OVERLOAD 1. Scope/Structure of CRW/CAMEO for emergency responders rather than experimentalists 2. Coarse Hazard Level dimethylmercury and methanol pictograms: 3. Classification accuracy Loose structural patterns
26 US A1 [paragraph:0056] rg- 13_35e esters can be reduced to alcohols with complex metal hydrides, especially lithium aluminum hydride. rg- 13_35b carboxylic acid esters can be reduced to aldehydes or alcohols, depending on conditions, by complex hydrides such as LiAlH4, LiBH4, NaAlH4, or DIBAL (diisobutylaluminum hydride) rg- 35_70d hydrides react spontaneously and irreversibly with proton donors, including alcohols, evolving flammable H2 gas
27 US A1 [paragraph:0056] rg- 14_42 solutions of molybdenum hexacarbonyl (42?) in diethylether (14) can explode after standing in air for an extended period. Chromium hexacarbonyl in diethylether may behave the same way rg- 35_42 the interaction between tetravinyllead (42?) and diborane (35) is explosively violent at ambient temperature. 14: Ethers 35: Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes 42: Organometallics (previously just matched as has metal )
28 ORGANOMETALIC STRUCTURAL PATTERN [#6]-[#M] carbon-metal bond H 3 C Li [#6].[#M] carbon and metal H 3 C CH 3 Li [#M] metal H 3 C CH 3 + Li [#M] = [!#1!#2!#5!#6!#7!#8!#9!#10!#14!#15!#16!#17! #18!#35!#36!#53!#54!#85!#86!#117!#118]
29 CAMEO COMPLETENESS
30 CAMEO INCONSISTENCIES
31
32
33 CONCLUSIONS Able to encode many chemical incompatibility matrices in Casandra s self contained XML rule format real- time alerting (ELN interaction) even with the moderately large rule set v2.0: Markush like queries, Custom properties CAMEO is an excellent resources for hazard information Still room for improvement and reorganisation: wiki, ontology, self- organising hierarchy, citations Repurposing for experimentalist is feasible given dedicate manual curation Validation corpus are relevant hazards identified/missed
34 FUTURES Classification And Labelling Requirements For Hazardous Substances And Mixtures Table Category Flash Point Initial Boiling Point GHS 1 Flammable Liquids < 23 C 35 C GHS 2 Flammable Liquids < 23 C > 35 C GHS 3 Flammable Liquids 23 C 60 C Liquid: i. vapour pressure 300 kpa at 50 C ii. not completely gaseous at 20 C at a standard pressure 101,3 kpa iii. (initial) melting point 20 C at a standard pressure 101,3 kpa
35 NextMove Software Daniel Lowe Noel O Boyle Bristol- Myers Squibb Dana Vanderwall Ramesh Durvasula Dong Li Carol McNab AMGEN Bharath Ramachandran Jen Sonnenberg Rhim Derek Brown ACKNOWLEDGEMENTS Booth #643 (too late) Slides will be available:
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