# US 10,309,212 B2 · Energetic cocrystals for treatment of a subterranean formation

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- Number: US 10,309,212 B2
- Document ID: US10309212B2
- Status: Granted
- Kind: B2
- Application number: 14/910,528
- Filed: 2013-08-27
- Published: 2016-06-23
- Granted: 2019-06-04
- Earliest claimed: 2013-08-27
- Assignees: Halliburton Energy Services, Inc.
- Applicants: Halliburton Energy Services, Inc.
- Inventors: Nathan Carl Schultheiss; Jeremy A. Holtsclaw
- Web page: https://patentgrep.com/patent/US10309212B2

## CPC

- E21B 49/00: Testing the nature of borehole walls; Formation testing; Methods or apparatus for obtaining samples of soil or well fluids, specially adapted to earth drilling or wells
- C06B 21/0066: {by granulation, e.g. flaking}
- C06B 25/04: the nitrated compound being an aromatic
- C06B 25/34: the compound being a nitrated acyclic, alicyclic or heterocyclic amine
- C06B 47/00: Compositions in which the components are separately stored until the moment of burning or explosion, e.g. "Sprengel"-type explosives; Suspensions of solid component in a normally non-explosive liquid phase, including a thickened aqueous phase
- C06B 47/14: comprising a solid component and an aqueous phase
- C09K 8/03: Specific additives for general use in well-drilling compositions
- C09K 8/52: Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K 8/62: Compositions for forming crevices or fractures
- C09K 8/72: Eroding chemicals, e.g. acids
- C09K 8/805: {Coated proppants}
- E21B 43/26: by forming crevices or fractures
- E21B 43/267: reinforcing fractures by propping
- G01V 1/104: using explosive charges (G01V1/157 takes precedence)
- G01V 1/288: {Event detection in seismic signals, e.g. microseismics (G01V1/36 takes precedence)}
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- C06B: EXPLOSIVES OR THERMIC COMPOSITIONS (blasting F42D); MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES (compounds in general C01, C07 or C08; {demolition agents based on cementitious or like materials C04B41/0009})
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G01V: GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS (means for indicating the location of accidentally buried, e.g. snow-buried, persons A63B29/02)

## Abstract

The present invention relates to energetic cocrystals, and to methods for using the same for treatment of a subterranean formation. In various embodiments, the present invention provides a method of treating a subterranean formation, the method including obtaining or providing a composition including energetic cocrystals. Each energetic cocrystal independently includes an energetic compound and a secondary material. The method also includes placing the composition in a subterranean formation.

## Claims

### Claim 1

A method of treating a subterranean formation, the method comprising:
placing in the subterranean formation a composition comprising energetic cocrystals, each energetic cocrystal independently comprising:
an energetic compound; and
a secondary material;
wherein each energetic cocrystal has a particle size of about 0.01 mm or less;
detonating the energetic cocrystals, wherein detonating the energetic cocrystals produces a compression wave;
measuring the compression wave; and
determining at least one characteristic of a fracture, flow path, area surrounding the fracture, area surrounding the flow path, or any combination thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein placing the composition in the subterranean formation comprises placing the composition in at least one of a fracture, at least a part of an area surrounding a fracture, a flow pathway, an area surrounding a flow pathway, and an area desired to be fractured.

### Claim 3 (depends on 2)

The method of claim 2, wherein the method further comprises hydraulic fracturing to generate the fracture or flow pathway.

### Claim 4 (depends on 1)

The method of claim 1, wherein the method comprises a method of approximately measuring at least one dimension of a fracture or flow pathway in the subterranean formation.

### Claim 5 (depends on 1)

The method of claim 1, further comprising detonating at least some of the cocrystals downhole.

### Claim 6 (depends on 5)

The method of claim 5, comprising triggering the detonating.

### Claim 7 (depends on 6)

The method of claim 6, wherein the triggering comprises exposing at least some of the cocrystals to at least one of a compression wave, a chemical activator, heat, pH change, pressure, friction, passage of time, and vibration.

### Claim 8 (depends on 5)

The method of claim 5, wherein the detonating is sufficient to generate a compression wave downhole at least partially within a fracture or flow pathway, wherein the method further comprises using the compression wave to measure at least one characteristic of the fracture or the flow pathway.

### Claim 9 (depends on 8)

The method of claim 8 wherein the measured characteristic comprises at least one of length, height, width, volume, surface area, shape, degree of closure, and time of closure.

### Claim 10 (depends on 8)

The method of claim 8, wherein using the compression wave to measure the characteristic comprises using a compression wave detector to approximately determine at least one dimension of an area surrounding the composition placed in the subterranean formation.

### Claim 11 (depends on 10)

The method of claim 10 wherein the compression wave detector is located at least one of downhole or above the surface.

### Claim 12 (depends on 1)

The method of claim 1, wherein the composition further comprises a carrier fluid.

### Claim 13 (depends on 1)

The method of claim 1, wherein the composition further comprises a viscosifier.

### Claim 14 (depends on 1)

The method of claim 1, wherein the cocrystal comprises a crystalline structure comprising a unit cell comprising both the energetic compound and the at least one secondary material.

### Claim 15 (depends on 1)

The method of claim 1, wherein the cocrystals are at least partially coated on a proppant.

### Claim 16 (depends on 1)

The method of claim 1, wherein the energetic compound is at least one of acetone peroxide, ammonium azide, ammonium chlorate, ammonium dinitramide, ammonium nitrate, ammonium permanganate, 1,1′-azobis-1,2,3-triazole, barium azide, benzotrifuroxan (BTF), tricyclo[3.1.0.02,6]hex-3-ene or benzvalene, 1,2,4-butanetriol trinitrate, chlorine azide, copper(I) acetylide, copper(II) azide, cyanuric triazide, diacetyl peroxide, 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), 6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one or diazodinitrophenol, diazomethane, diethylene glycol dinitrate, 4-dimethylaminophenylpentazole, 4,4′-dinitro-3,3′-diazenofuroxan (DDF), 2,4-dinitrotoluene, [(2R,3R)-1,3,4-trinitrooxybutan-2-yl] nitrate or erythritol tetranitrate, ethyl azide, ethylene glycol dinitrate, fluorine perchlorate, 1,1-diamino-2,2-dinitroethene (FOX-7 or DADNE), N,N′-bis-(1H-tetrazol-5-yl)-hydrazine (HMT), heptanitrocubane (HNC), 3,4,8,9,12,13-hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane or hexamethylene triperoxide diamine (HMTD), hexanitrobenzene (HNB), 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)aniline or hexanitrodiphenylamine (HND), hexanitroethane, 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW or CL-20), 1,3,5-trinitro-2-[2-(2,4,6-trinitrophenyl)ethenyl]benzene or hexanitrostilbene (HNS), 2,6-dioxo-1,3,4,5,7,8-hexanitrodecahydro-1H,5H-diimidazo[4,5-b:4′,5′-e] (HHTDD), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hydrazoic acid or hydrogen azide, lead 2,4,6-trinitrobenzene-1,3-diolate or lead styphnate, lead(II) azide, manganese heptoxide, (2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol-1,2,3,4,5,6-hexanitrate or mannitol hexanitrate, methyl azide, methyl nitrate, methylammonium nitrate; 1-methyl-2-nitro-benzene or mononitrotoluene, nitrocellulose, nitrogen trichloride, nitrogen triiodide, nitroglycerin, nitroguanidine, nitromethane, nitrostarch, 5-nitro-1,2,4-triazol-3-one (NTO), nitrourea, octaazacubane, octanitrocubane (ONC), [3-nitrooxy-2,2-bis(nitrooxymethyl)propyl]nitrate or pentaerythritol tetranitrate (PETN), pentazenium, pentazole, picric acid, picryl chloride, polycarbonyl, polyvinyl nitrate, potassium picrate, propylene glycol dinitrate, 1,3,5-trinitroperhydro-1,3,5-triazine (RDX), silicon tetraazide, silver acetylide, silver azide, silver nitride, sodium azide, 2,4,6-trinitrobenzene-1,3-diol or styphnic acid, 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), tetraazidomethane, tetranitromethane, 1-(5-tetrazolyl)-3-guanyl tetrazene hydrate, N-methyl-N,2,4,6-tetranitroaniline or tetryl, 1,3,5-triazido-2,4,6-trinitrobenzene, 2,2′-(ethane-1,2-diylbis(oxy))bisethyl dinitrate] or tri ethylene glycol dinitrate, [2-methyl-3-nitrooxy-2-(nitrooxymethyl)propyl] nitrate or trimethylolethane trinitrate (TMETN or METN), 2,4,6-trinitroaniline, 2-methoxy-1,3,5-trinitrobenzene or trinitroanisole (TNA), 1,3,5-trinitrobenzene (TNB), 2,4,6-trinitrobenzenesulfonic acid, 1,3,3-trinitroazetidine (TNAZ), 1-methyl-amino-2,4,6-trinitrobenzene (MATNB), 2-methyl-1,3,5-trinitrobenzene or trinitrotoluene (TNT), 2,4,6-trinitro-1,3,5-triazine or trinitrotriazine, 2,4,6-tris(trinitromethyl)-1,3,5-triazine, urea nitrate, and 1,2,3,4,5-pentakis-nitrooxy-pentane or xylitol pentanitrate.

### Claim 17 (depends on 1)

The method of claim 1, wherein the secondary material is a substantially nonenergetic material or a substantially inert material, or an energetic material that is different than the energetic compound.

### Claim 18 (depends on 1)

The method of claim 1, wherein the secondary material is at least one of acetone peroxide, ammonium azide, ammonium chlorate, ammonium dinitramide, ammonium nitrate, ammonium permanganate, 1,1′-azobis-1,2,3-triazole, barium azide, benzotrifuroxan (BTF), tricyclo[3.1.0.02,6]hex-3-ene or benzvalene, 1,2,4-butanetriol trinitrate, chlorine azide, copper(I) acetylide, copper(II) azide, cyanuric triazide, diacetyl peroxide, 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), 6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one or diazodinitrophenol, diazomethane, diethylene glycol dinitrate, 4-dimethylaminophenylpentazole, 4,4′-dinitro-3,3′-diazenofuroxan (DDF), 2,4-dinitrotoluene, [(2R,3R)-1,3,4-trinitrooxybutan-2-yl] nitrate or erythritol tetranitrate, ethyl azide, ethylene glycol dinitrate, fluorine perchlorate, 1,1-diamino-2,2-dinitroethene (FOX-7 or DADNE), N,N′-bis-(1H-tetrazol-5-yl)-hydrazine (HBT), heptanitrocubane (HNC), 3,4,8,9,12,13-hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane or hexamethylene triperoxide diamine (HMTD), hexanitrobenzene (HNB), 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)aniline or hexanitrodiphenylamine (HND), hexanitroethane, 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW or CL-20), 1,3,5-trinitro-2-[2-(2,4,6-trinitrophenyl)ethenyl] benzene or hexanitrostilbene (HNS), 2,6-dioxo-1,3,4,5,7,8-hexanitrodecahydro-1H,5H-diimidazo[4,5-b:4′,5′-e] (HHTDD), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hydrazoic acid or hydrogen azide, lead 2,4,6-trinitrobenzene-1,3-diolate or lead styphnate, lead(II) azide, manganese heptoxide, (2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol-1,2,3,4,5,6-hexanitrate or mannitol hexanitrate, methyl azide, methyl nitrate, methyl ammonium nitrate, 1-methyl-2-nitro-benzene or mononitrotoluene, nitrocellulose, nitrogen trichloride, nitrogen triiodide, nitroglycerin, nitroguanidine, nitromethane, nitrostarch, 5-nitro-1,2,4-triazol-3-one (NTO), nitrourea, octaazacubane, octanitrocubane (ONC), [3-nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate or pentaerythritol tetranitrate (PETN), pentazenium, pentazole, picric acid, picryl chloride, polycarbonyl, polyvinyl nitrate, potassium picrate, propylene glycol dinitrate, 1,3,5-trinitroperhydro-1,3,5-triazine (RDX), silicon tetraazide, silver acetylide, silver azide, silver nitride, sodium azide, 4,6-trinitrobenzene-1,3-diol or styphnic acid, 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), tetraazidomethane, tetranitromethane, 1-(5-tetrazolyl)-3-guanyl tetrazene hydrate, N-methyl-N,2,4,6-tetranitroaniline or tetryl, 1,3,5-triazido-2,4,6-trinitrobenzene, 2,2′-(ethane-1,2-diylbis(oxy))bisethyl dinitrate] or triethylene glycol dinitrate, [2-methyl-3-nitrooxy-2-(nitrooxymethyl)propyl] nitrate or trimethylolethane trinitrate (TMETN or METN), 2,4,6-trinitroaniline, 2-methoxy-1,3,5-trinitrobenzene or trinitroanisole (TNA), 1,3,5-trinitrobenzene (TNB), 2,4,6-trinitrobenzenesulfonic acid, 1,3,3-trinitroazetidine (TNAZ), 1-methyl-amino-2,4,6-trinitrobenzene (MATNB), 2-methyl-1,3,5-trinitrobenzene or trinitrotoluene (TNT), 2,4,6-trinitro-1,3,5-triazine or trinitrotriazine, 2,4,6-tris(trinitromethyl)-1,3,5-triazine, urea nitrate, and 1,2,3,4,5-pentakis-nitrooxy-pentane or xylitol pentanitrate, N-methyl-2-pyrrolidone, 2,4-dinitro-2,4-diazapentane, 1,2-phenylenediamine, 2-bromoaniline, 3,4-diaminotoluene, 4-fluoroaniline, thieno[3,2-b]thiophene, dimethylformamide (DMF), 2-pyrrolidone, 2-picoline-N-oxide, 4-picoline-N-oxide, naphthalene, 1-bromonaphthalene, 9-bromonaphthalene, anthracene, 9-bromoanthracene, phenanthrene, perylene, tetrathiafulvalene, phenothiazine, dibenzothiophene 4,6-dimethyldibenzothiophene, 1,2-phenylenediamine, 1,4-dimethyoxybenzene, 4-aminobenzoic acid, 1,4-piperazinedicarboxaldehyde, anthranilic acid, pyrene, caprolactam, H2O, CO2, dimethylformamide (DMF), 1,4-□□□□□□□□□□-butyrolactone, and hexamethylphosphoramide.

### Claim 19 (depends on 1)

The method of claim 1, wherein at least one of
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is N-methyl-2-pyrrolidone,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 2,4-dinitro-2,4-diazapentane in a mole ratio of about 1:2,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 1,2-phenylenediamine in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 2-bromoaniline in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 3,4-diaminotoluene in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 4-fluoroaniline in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is thieno[3,2-b]thiophene in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is dimethylformamide (DMF),
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 2-pyrrolidone in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 4-picolene-N-oxide in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 2-picoline-N-oxide in a mole ratio of about 1:2,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 1,4-piperazinedicarboxaldehyde in a mole ratio of about 1:1,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) in a mole ratio of about 1:2,
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is 5-nitro-1,2,4-triazol-3-one (NTO),
the energetic compound is octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and the secondary material is H2O in a mole ratio of about 2:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 1,3,5-trinitrobenzene (TNB) in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is naphthalene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 1-bromonaphthalene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 9-bromonaphthalene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is anthracene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 9-bromoanthracene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is phenanthrene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is perylene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is tetrathiafulvalene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is thieno[3,2-b]thiophene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is phenothiazine in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is dibenzothiophene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 4,6-dimethyldibenzothiophene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 1,2-phenylenediamine in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 1,4-dimethyoxybenzene in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 4-aminobenzoic acid in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is 4-aminobenzoic acid in a mole ratio of about 1:2,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is anthranilic acid in a mole ratio of about 1:1,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is anthranilic acid in a mole ratio of about 1:2,
the energetic compound is 2,4,6-trinitrotoluene (TNT) and the secondary material is pyrene in a mole ratio of about 1:1,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is caprolactam,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is H2O in a mole ratio of about 1:1,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is dimethylformamide (DMF) in a mole ratio of about 1:2,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is CO2 in a mole ratio of about 2:1,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is γ-butyrolactone in a mole ratio of about 1:1,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and and the secondary material is benzotrifuroxan (BTF) in a mole ratio of about 1:1,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is 1,4-dioxane in a mole ratio of about 2:7,
the energetic compound is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) and the secondary material is hexamethylphosphoramide in a mole ratio of about 1:4,
the energetic compound is benzotrifuroxan (BTF) and the secondary material is 1,3,5-trinitrobenzene (TNB) in a mole ratio of about 1:1,
the energetic compound is benzotrifuroxan (BTF) and the secondary material is 2-methoxy-1,3,5-trinitrobenzene or trinitroanisole (TNA) in a mole ratio of about 1:1,
the energetic compound is benzotrifuroxan (BTF) and the secondary material is 2,4,6-trinitrotoluene (TNT) in a mole ratio of about 1:1,
the energetic compound is benzotrifuroxan (BTF) and the secondary material is 1,3,3-trinitroazetidine (TNAZ) in a mole ratio of about 1:1, and
the energetic compound is benzotrifuroxan (BTF) and the secondary material is 1-methyl-amino-2,4,6-trinitrobenzene (MATNB) in a mole ratio of about 1:1.

### Claim 20 (depends on 1)

The method of claim 1, wherein the secondary material is not energetic, and wherein the energetic crystals are detonated in the fracture in the subterranean formation.

### Claim 21 (depends on 20)

The method claim 20, wherein the energetic cocrystals are stable at surface temperatures and pressures, and wherein the energetic cocrystals detonated in response to at least one of heat or pressure in the subterranean formation, wherein the pressure is from closure stress of the fracture.

### Claim 22

A method of treating a subterranean formation, the method comprising:
placing a composition comprising energetic cocrystals in the subterranean formation comprising at least one of a fracture, flow pathway, area surrounding a fracture, and an area surrounding a flow pathway, each energetic cocrystal independently comprising
an energetic compound; and
a secondary material that is not energetic;
detonating at least some of the energetic cocrystals to generate a compression wave, wherein detonating at least some of the energetic cocrystals to generate a compression wave comprises exposing at least some of the cocrystals to at least one of a compression wave, heat, pH change, pressure, friction, and vibration; and
using the compression wave to determine at least one characteristic of the fracture, flow pathway, area surrounding the fracture, or area surrounding the flow pathway.

### Claim 23 (depends on 22)

The method of claim 22, wherein the energetic cocrystals are stable at surface temperatures and pressures, and wherein the energetic cocrystals detonate in response to at least one of heat or pressure in the subterranean formation, wherein the pressured is from closure stress of the fracture.