WO2017211932A1 - Cyclohexandiamine zur verwendung in der gaswäsche - Google Patents
Cyclohexandiamine zur verwendung in der gaswäsche Download PDFInfo
- Publication number
- WO2017211932A1 WO2017211932A1 PCT/EP2017/063921 EP2017063921W WO2017211932A1 WO 2017211932 A1 WO2017211932 A1 WO 2017211932A1 EP 2017063921 W EP2017063921 W EP 2017063921W WO 2017211932 A1 WO2017211932 A1 WO 2017211932A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- absorbent
- diaminocyclohexane
- carbon dioxide
- absorption
- gas
- Prior art date
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- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical class NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 title description 2
- 238000005201 scrubbing Methods 0.000 title description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 98
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 59
- 239000012530 fluid Substances 0.000 claims abstract description 31
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 29
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical class NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 150000003141 primary amines Chemical class 0.000 claims abstract description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 239000002250 absorbent Substances 0.000 claims description 84
- 230000002745 absorbent Effects 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 16
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 12
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- KIDJHPQACZGFTI-UHFFFAOYSA-N [6-[bis(phosphonomethyl)amino]hexyl-(phosphonomethyl)amino]methylphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCCCCCN(CP(O)(O)=O)CP(O)(O)=O KIDJHPQACZGFTI-UHFFFAOYSA-N 0.000 description 1
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- KVZJLSYJROEPSQ-UHFFFAOYSA-N cis-DMCH Natural products CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 description 1
- PFURGBBHAOXLIO-OLQVQODUSA-N cis-cyclohexane-1,2-diol Chemical compound O[C@H]1CCCC[C@H]1O PFURGBBHAOXLIO-OLQVQODUSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000009264 composting Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- STENYDAIMALDKF-UHFFFAOYSA-N cyclobutane-1,3-diol Chemical compound OC1CC(O)C1 STENYDAIMALDKF-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 150000004985 diamines Chemical group 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- XYXCXCJKZRDVPU-UHFFFAOYSA-N hexane-1,2,3-triol Chemical compound CCCC(O)C(O)CO XYXCXCJKZRDVPU-UHFFFAOYSA-N 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- AAYGSSGHJGVNSK-UHFFFAOYSA-N hexane-1,3,6-triol Chemical compound OCCCC(O)CCO AAYGSSGHJGVNSK-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- RCZLVPFECJNLMZ-UHFFFAOYSA-N n,n,n',n'-tetraethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN(CC)CC RCZLVPFECJNLMZ-UHFFFAOYSA-N 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1475—Removing carbon dioxide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
- C10L3/101—Removal of contaminants
- C10L3/102—Removal of contaminants of acid contaminants
- C10L3/104—Carbon dioxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/2041—Diamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20436—Cyclic amines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
Definitions
- the present invention relates to the use of certain cyclohexanediamines for removing carbon dioxide from fluid streams, absorbents containing these compounds, and a method for removing carbon dioxide from fluid streams.
- the content of sulfur compounds of natural gas must be reduced by suitable treatment measures directly at the natural gas source, because the sulfur compounds form acids in the water frequently carried by natural gas, which have a corrosive effect.
- suitable treatment measures directly at the natural gas source, because the sulfur compounds form acids in the water frequently carried by natural gas, which have a corrosive effect.
- LNG natural gas liquefaction plant
- predetermined limit values of the sulfur-containing impurities must be adhered to.
- many sulfur compounds are foul-smelling and toxic even at low concentrations.
- washes are used with aqueous solutions of inorganic or organic bases.
- ions form with the bases.
- the absorbent can be regenerated by relaxing to a lower pressure and / or stripping whereby the ionic species react back to sour gases and / or are stripped off by steam. After the regeneration process, the absorbent can be reused.
- High CO 2 absorption rates are achieved through the use of high C02 affinity absorbents, such as primary and secondary alkanolamines.
- the high C02 affinity implies that the CO 2 absorption is highly exothermic. However, such absorbents require due to the high amount of Absorption reaction enthalpy also usually higher energy consumption during regeneration.
- Sterically unhindered primary or secondary amines for example piperazine
- promoters can accelerate the CO 2 absorption of tertiary amines by intermediate formation of a carbamate structure.
- the absorption rate is high, but only one C02 molecule can be taken up by two amine molecules.
- US 4,336,233 discloses a method for removing CO2 and / or H2S from gases by means of an aqueous absorbent containing MDEA and piperazine.
- the use of piperazine as the C02 promoter allows a much higher CO 2 absorption rate over systems without a promoter.
- piperazine is a solid at ambient temperatures; his dusts have a sensitizing effect.
- the invention has for its object to provide further compounds which promote rapid absorption of carbon dioxide from fluid streams.
- the aqueous solutions containing the compounds should have low crystallization temperatures.
- the object is achieved by using a 1, 3-Diaminocyclohexans of the general formula (I) for removing carbon dioxide from fluid streams
- R is independently C 1-4 -alkyl; and n is an integer from 0 to 3.
- the invention also relates to an absorbent for removing carbon dioxide from fluid streams containing
- the invention also relates to a process for removing carbon dioxide from a fluid stream by contacting the fluid stream with the absorbent.
- the radical R is preferably methyl or ethyl, in particular methyl.
- the coefficient n is preferably 1 or 2, in particular 1.
- each of R's is preferably located in the ⁇ position to at least one amino group.
- Particularly preferred compounds are 4-methylcyclohexane-1,3-diamine, 2-methylcyclohexane-1,3-diamine or a mixture thereof, in particular trans-4- Methylcyclohexane-1,3-diamine, frans-2-methylcyclohexane-1,3-diamine or a mixture thereof.
- the amino groups in the 1, 3-diaminocyclohexane of the general formula (I) are arranged trans to each other with respect to the Cyclohexanringebene.
- the configuration information ice or trans in ice or tränst, 3-diaminocyclohexane refers to the relative arrangement of the amino groups with respect to the cyclohexane ring level. It can be seen that the number of stereoisomers is higher if, in addition to the two amino groups, further substituents on the cyclohexane ring are present. For the purposes of the present invention, these stereoisomers are assigned to two groups, namely a group in which the amino groups are present to each other ice, and a group in which the amino groups frans to each other.
- the proportion of the frans-diaminocyclohexane based on the sum of the cis- and tränst, 3-diaminocyclohexane, preferably at least 80%, in particular at least 95%, particularly preferably a substantially pure, tränst, 3-diaminocyclohexane eingtag. Since the trans-diaminocyclohexane is not able to react irreversibly with carbon dioxide, the cyclic capacity of the absorbent remains long-term.
- 1, 3-diaminocyclohexanes are available, for example, by hydrogenation of 1, 3-phenylenediamines. Such a method is described in US 6,075,167.
- the 1, 3-phenylenediamines are obtainable by reduction of dinitroalkylbenzenes. accessible.
- a suitable starting material is 2,4-dinitrotoluene, which may contain varying amounts of 2,6-dinitrotoluene.
- polyols such as ethylene glycol, 1, 2-propanediol, 2-methylpropane-1, 3-diol, 1, 2-butanediol, 2,3-butanediol, 2-methyl-1-butan-1, 2-diol, 3 -Methylbutane-1, 2-diol, 3-methyl-1, 3-butanediol, 1, 2-pentanediol, 1, 3-pentanediol, 2,4-pentanediol, 2,3-pentanediol, 1, 2-hexanediol, cis -1, 2-cyclopentanediol, trans-1, 2-cyclopentanediol, cis-1, 2-cyclohexanediol, trans-1, 2-cyclohexanediol, 1, 3-propanediol, 2-methyl-1, 3-propanediol, 2 , 2, --
- 1, 3-propanediol is preferred.
- the extractant has a higher affinity for c / s-1,3-diaminocyclohexane than for frans-1,3-diaminocyclohexane.
- fran-enriched 1,3-diaminocyclohexane can be obtained overhead, while the extractant and c / s-1,3-diaminocyclohexane remain in the bottom of the distillation during the distillation or, in the case of continuous reaction, are withdrawn via the bottom.
- Discrimination of cis- and frans-1, 3-diaminocyclohexanes is also possible by reacting a mixture of cis- and frans-1,3-diaminocyclohexanes with carbon dioxide and selectively obtaining the urea of c / s-1,3-diaminocyclohexane.
- the reaction takes place, for example, in aqueous solution by heating a CO 2 -saturated aqueous solution of a mixture of cis- and p-1,3-diaminocyclohexanes under autogenous pressure in a pressure-tight vessel.
- the urea derivative can then be readily separated from the unreacted frans-1,3-diaminocyclohexane, e.g. B. by precipitation, crystallization or distillation.
- Particularly suitable is a two-stage separation process in which initially an enrichment of frans-1, 3-diaminocyclohexanes by extractive distillation takes place and the remaining remaining cis-, 3-diaminocyclohexanes is selectively reacted with carbon dioxide and separated. In this way, the frans-1, 3-diaminocyclohexane can be obtained substantially free from c / s-1,3-diaminocyclohexane.
- the absorbent according to the invention contains a 1, 3-diaminocyclohexane of the general formula (I). In a preferred embodiment, it also contains at least one tertiary amine and / or a sterically hindered primary or secondary amine.
- the concentration of the tertiary amine and / or sterically hindered primary or secondary amine in the absorbent is 10 to 60 wt .-%, preferably 20 to 50 wt .-%, particularly preferably 30 to 50 wt .-%, the
- Concentration desl, 3-cyclohexanediamine in the absorbent 5 to 40 wt .-%, preferably 5 to 30 wt .-%, particularly preferably 10 to 25 wt .-%.
- the absorbent comprises an aqueous solution.
- the absorbent contains at least one organic solvent.
- the organic solvent is preferably selected from sulfolane, glycols such as ethylene glycol, diethylene glycol, ethylene glycol dimethyl ether,
- Triethylene glycol triethylene glycol dimethyl ether, di- or mono (C 1-4 -alkyl ethers) monoethylglycols and di- or mono (C 1-4 -alkyl ethers) polyethylene glycols, N-methylpyrrolidone, N-methyl-3-morpholine, N-formylmorpholine, N-acetylmorphine, N, N-dimethylformamide, N, N-dimethylimidazolidin-2-one, N-methylimidazole, and mixtures thereof.
- the absorbent contains in addition to the compound of the general formula (I) at least one tertiary amine and / or a sterically hindered primary or secondary amine.
- tertiary amine is understood as meaning compounds having at least one tertiary amino group
- the tertiary amine preferably contains exclusively tertiary amino groups, that is to say it contains no primary or secondary amino groups in addition to at least one tertiary amino group.
- Suitable tertiary amines include in particular: 1. Tertiary alkanolamines like
- ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylethylenediamine N, N-diethyl-N', N'-dimethylethylenediamine, ⁇ , ⁇ , ⁇ ', ⁇ '-tetraethylethylenediamine, N, N, N', N'-tetramethyl- 1,3-propanediamine (TMPDA), N, N, N ', N'-tetraethyl-1,3-propanediamine (TEPDA), N, N, N', N'-tetramethyl-1,6-hexanediamine, N, N-dimethyl-N ', N'-diethylethylenediamine (DMDEEDA), 1-dimethylamino-2-dimethylaminoethoxyethane (bis [2- (dimethylamino) ethyl] ether),
- steric hindrance is meant the presence of at least one secondary or tertiary carbon atom in the immediate vicinity of the sterically hindered position.
- amines include, in addition to sterically hindered amines, also compounds which are referred to in the art as highly hindered amines and have a steric parameter (taffeta constant) of greater than 1.75.
- a secondary carbon atom is understood to mean a carbon atom which has two carbon-carbon bonds in addition to the bond to the sterically hindered position.
- a tertiary carbon atom is understood to mean a carbon atom which has three carbon-carbon bonds in addition to the bond to the sterically hindered position.
- a secondary amine is meant a compound having a nitrogen atom substituted with two organic radicals other than hydrogen (eg, alkyl radical, alkenyl radical, aryl radical, alkylaryl radical, etc.).
- suitable sterically hindered primary or secondary amines are 2- (2-tert-butylaminoethoxy) ethanol (TBAEE), 2- (isopropylamino) ethanol (IPAE) and
- the absorbent contains at least one acid.
- the acid is suitably selected from protonic acids (Brönstedt acids).
- the acid is selected from organic and inorganic acids. Suitable organic acids include, for example, phosphonic acids, sulfonic acids, carboxylic acids and amino acids.
- the acid is a polybasic acid.
- phosphoric acid and sulfuric acid are preferable.
- carboxylic acids formic acid, acetic acid, benzoic acid, succinic acid and adipic acid are preferred.
- sulfonic acids methanesulfonic acid, p-toluenesulfonic acid and 2- (4- (2-hydroxyethyl) -1-piperazinyl) ethanesulfonic acid (HEPES) are preferable.
- phosphonic acids are 2-hydroxyphosphonoacetic acid, 2-phosphonobutane-1, 2,4-tricarboxylic acid, 1-hydroxyethane-1,1-diphosphonic acid, ethylenediamine-tetra- (methylenephosphonic acid), diethylenetriamine-penta (methylenephosphonic acid),
- HDTMP Bis (hexamethylene) triamine penta (methylenephosphonic acid)
- nitrilotris methylenephosphonic acid
- the absorbent may also contain additives such as corrosion inhibitors, enzymes, etc.
- additives such as corrosion inhibitors, enzymes, etc.
- the amount of such additives will range from about 0.01 to 3% by weight of the absorbent.
- the absorbent or method according to the invention is suitable for the treatment of fluids of all kinds.
- Fluids are on the one hand gases such as natural gas, synthesis gas, coke oven gas, cracked gas, coal gasification gas, cycle gas, landfill gas and combustion gases, and on the other hand with the absorbent substantially immiscible liquids, such as liquefied petroleum gas (LPG) or natural gas liquefied natural gas (NGL).
- LPG liquefied petroleum gas
- NTL natural gas liquefied natural gas
- the fluid stream is a flue gas stream, e.g. B. from incinerators, production gases, synthesis gas or indoor air.
- C02-containing fluid streams are fermentation gases from the methanogenesis of biomass, digestion gases from the aerobic and / or anaerobic composting of biomass, combustion gases, animal digestive gases in factory farming and C02-containing indoor air in building and vehicle air conditioning systems.
- the fluid stream contains carbon dioxide and / or hydrogen sulfide; it may also contain other acidic gases, such as COS and mercaptans.
- S0 3 , S0 2 , CS 2 and HCN can be removed.
- the compounds of the general formula (I) according to the invention are particularly suitable in processes or absorption media for the treatment of hydrocarbon-containing fluid streams.
- the hydrocarbons contained are z.
- aliphatic hydrocarbons such as Ci-C4 hydrocarbons such as methane, unsaturated hydrocarbons such as ethylene or propylene, or aromatic hydrocarbons such as benzene, toluene or xylene.
- the method according to the invention is suitable for the treatment of a natural gas stream.
- the inventive method or absorbent is particularly suitable for the removal of CO2.
- the fluid stream is brought into contact with the absorption medium in an absorption step in an absorber, whereby at least partial leaching of carbon dioxide and / or hydrogen sulphide takes place.
- the absorber is a washing device used in conventional gas scrubbing processes. Suitable washing devices are, for example, random packings, packing and tray columns, membrane contactors, radial flow scrubbers, jet scrubbers, venturi scrubbers and rotary scrubbers, preferably packed, packed and tray columns, more preferably bottom and packed columns.
- the treatment of the fluid stream with the absorbent is preferably carried out in a column in countercurrent.
- the fluid is generally fed into the lower region and the absorbent in the upper region of the column.
- tray columns sieve bell or valve trays are installed, over which the liquid flows.
- Packed columns can be filled with different moldings. Heat and mass transfer are improved by the enlargement of the surface due to the usually about 25 to 80 mm large moldings.
- Raschig ring a hollow cylinder
- Pall ring a hollow cylinder
- Hiflow ring Hiflow ring
- Intalox saddle the like.
- the packing can be ordered, but also random (as a bed) are introduced into the column.
- Possible materials are glass, ceramics, metal and plastics.
- Structured packings are a further development of the ordered packing. They have a regularly shaped structure. This makes it possible for packings to reduce pressure losses in the gas flow.
- the material used can be metal, plastic, glass and ceramics.
- the temperature of the absorbent in the absorption step is generally about 30 to 100 ° C, using a column, for example 30 to 70 ° C at the top of the column and 50 to 100 ° C at the bottom of the column.
- the total pressure in the absorption step is generally about 1 to 180 bar, preferably about 1 to 100 bar.
- the inventive method may one or more, for. B. comprise two, successive absorption steps.
- the absorption can be carried out in several successive sub-steps, wherein the raw gas containing the acidic gas constituents in each of the substeps is brought into contact with a partial stream of the absorbent.
- the absorbent, with which the raw gas is brought into contact may already be partially loaded with acidic gases, d. H. it may, for example, be an absorbent, which has been recycled from a subsequent absorption step to the first absorption step, or partially regenerated absorbent.
- the performance of the two-stage absorption reference is made to the publications EP 0 159 495, EP 0 190 434, EP 0 359 991 and WO 00100271.
- the method preferably comprises a regeneration step in which the CO2 and F S-laden absorbent is regenerated.
- the regeneration step CO2 and H2S and possibly other acidic gas constituents are released from the CO2- and Fs-laden absorption medium, a regenerated absorption medium being obtained.
- the regenerated absorbent is then returned to the absorption step.
- the regeneration step comprises at least one of heating, relaxing and stripping with an inert fluid.
- the regeneration step preferably comprises heating the absorbent laden with the acidic gas constituents.
- the absorbed acid gases are stripped off by means of the water vapor obtained by heating the solution.
- an inert fluid such as nitrogen may also be used.
- the absolute pressure in the desorber is normally 0.1 to 3.5 bar, preferably 1 to 0 2.5 bar.
- the temperature is usually from 50 ° C to 170 ° C, preferably from 80 ° C to 130 ° C, the temperature of course being dependent on the pressure.
- the regeneration step may alternatively or additionally include a pressure release. This involves at least a pressure release of the loaded absorbent from a high pressure, as it prevails in the implementation of the absorption step, to a lower pressure.
- the pressure release can be done for example by means of a throttle valve and / or an expansion turbine.
- the regeneration with a relaxation stage is described, for example, in the publications US Pat. Nos. 4,537,753 and 4,553,984.
- the release of the acidic gas constituents in the regeneration step for example, in a flash column, z. B. a vertically or horizontally installed flash tank or a countercurrent column with internals, done.
- the regeneration column may likewise be a packed, packed or tray column.
- the regeneration column has a heater at the bottom, z. B. a reboiler, natural circulation evaporator, forced circulation evaporator, or forced circulation evaporator.
- the regeneration column has an outlet for the released acid gases. Entrained absorbent vapors are condensed in a condenser and returned to the column.
- FIG. 1 is a schematic representation of an apparatus suitable for carrying out the method according to the invention.
- FIG. 2 is a schematic representation of a double stir cell arrangement used to determine the relative rates of CO2 absorption of absorbents.
- FIG. 1 a suitably pretreated gas containing hydrogen sulphide and / or carbon dioxide is brought into contact in a countercurrent via the feed line Z in an absorber A1 with regenerated absorption medium which is supplied via the absorption medium line 1 .01.
- the absorbent removes hydrogen sulfide and / or carbon dioxide by absorption from the gas;
- clean gas, depleted in hydrogen sulphide and / or carbon dioxide is obtained via the exhaust line 1.02.
- the heat exchanger 1 .04 in which the CO2 and / or F s-laden absorbent is heated with the heat of the fed via the absorption medium line 1 .05, regenerated absorbent, and the absorbent line is 1.06 fed with CO2 and / or F S-laden absorbent of the desorption column D and regenerated. From the lower part of the desorption column D, the absorbent is fed to the reboiler 1 .07, where it is heated.
- the main water-containing vapor is returned to the desorption column D, while the regenerated absorbent via the absorbent line 1.05, the heat exchanger 1 .04 in which the regenerated absorbent heats the CO2 and / or F S-loaded absorbent and thereby cools the absorbent line 1.08, the radiator 1.09 and the absorbent line 1.01 the absorber A1 is fed back.
- the heat exchanger types for generating the stripping steam can be used, such as a natural circulation evaporator, forced circulation evaporator, or Zwangsumlau- fentnapssverdampfer.
- a mixed phase stream of regenerated absorbent and stripping vapor is returned to the bottom of the desorption column where phase separation between the vapor and the absorbent takes place.
- the regenerated absorbent to the heat exchanger 1.04 is either withdrawn from the recycle stream from the bottom of the desorption column to the evaporator, or passed through a separate line directly from the bottom of the desorption column to the heat exchanger 1 .04.
- the released in the desorption column D CO2 and / or F S-containing gas leaves the desorption column D via the exhaust pipe 1.10. It is passed into a capacitor with integrated phase separation 1.1 1, where it is separated by entrained absorbent vapor. Condensation and phase separation are also present separately.
- a liquid consisting mainly of water passed through the absorbent line 1.12 in the upper region of the desorption column D, and carried out a CO2 and / or h S-containing gas via the gas line 1.13.
- A C02 storage tank
- B double stirrer cell
- C temperature controller
- D metering valve
- E pressure gauge.
- A C02 storage tank
- B double stirrer cell
- C temperature controller
- D metering valve
- E pressure gauge.
- A C02 storage tank
- B double stirrer cell
- C temperature controller
- D metering valve
- E pressure gauge.
- A C02 storage tank
- B double stirrer cell
- C temperature controller
- D metering valve
- E pressure gauge.
- the double-stirred cell had an inner diameter of 85 mm and a volume of 509 ml.
- the temperature of the cell was maintained at 50 ° C during the measurements.
- the cell according to FIG. 2 comprised two stirrers. Before starting the measurement, the double-stirred cell was evacuated. A defined volume of degassed absorbent was added to the double-stirred cell and the temperature was controlled to 50 ° C. The stirrers were already turned on during the heating of the unloaded absorbent. The speed of the stirrer was chosen so that a planar phase interface formed between the liquid and the gas phase. A wave development at the phase interface must be avoided, otherwise no defined phase interface would exist.
- the absorption rate in moles (CO 2) / (m 3 absorption medium * min) was calculated as a function of the loading of the absorbent.
- the absorption rate was calculated from the volume flow of the carbon dioxide and the volume absorbent provided.
- the load was calculated from the cumulative amount of carbon dioxide fed into the measuring cell and the mass absorbent presented.
- a loading test and a subsequent stripping test were carried out for the following aqueous absorbents:
- the apparatus used was a thermostatted glass cylinder with an attached reflux condenser. Of the Reflux condenser was operated at a temperature of about 5 ° C and prevented that water and amine was discharged during the loading or the stripping.
- each 100 ml_ of the absorbent were filled into the glass cylinder. Via a frit at the lower end of the glass cylinder, 20 NL / h of pure CO2 were bubbled into the absorption solution for about 4 h. Subsequently, the loading of CO2 in the absorbent was determined by measuring the total inorganic carbon content (TOC-V Series Shimad-zu). The loaded solutions were then stripped in an identically constructed apparatus at 80 ° C with nitrogen (20 NL / h). After 60 minutes, a sample of the absorbent was taken and analyzed for CO 2 content. The difference between the C02 loading reached at the end of the loading test and the end of the stripping test results in the cyclic capacities of the absorbents.
- Example 2-5 shows that an MDACH-containing absorbent has a higher cyclic capacity than an absorbent containing the primary alkanolamine MEA (Comparative Example 2-4).
- a sample jar was filled with about 5-20 ml of unloaded absorbent.
- a thermometer was introduced. The system was first homogenized in liquid phase and then slowly cooled until solid formation was observed. At that moment, the sample glass was taken out of the cooling bath and the temperature allowed to rise slowly. The temperature was recorded at which the solid was completely dissolved again and there was only one liquid phase. The procedure was performed in triplicate for each sample.
- the MDACH-containing absorbents advantageously show low crystallization temperatures.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Gas Separation By Absorption (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2017277604A AU2017277604A1 (en) | 2016-06-10 | 2017-06-08 | Cyclohexandiamines for use in gas scrubbing |
EP17728220.9A EP3468692A1 (de) | 2016-06-10 | 2017-06-08 | Cyclohexandiamine zur verwendung in der gaswäsche |
US16/306,784 US20190126194A1 (en) | 2016-06-10 | 2017-06-08 | Cyclohexanediamines for use in gas scrubbing |
RU2019100012A RU2019100012A (ru) | 2016-06-10 | 2017-06-08 | Циклогександиамины для применения в промывке газов |
CA3027122A CA3027122A1 (en) | 2016-06-10 | 2017-06-08 | Cyclohexandiamines for use in gas scrubbing |
JP2018564729A JP2019520201A (ja) | 2016-06-10 | 2017-06-08 | ガススクラビング用のシクロヘキサンジアミン |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP16173866 | 2016-06-10 | ||
EP16173866.1 | 2016-06-10 |
Publications (1)
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WO2017211932A1 true WO2017211932A1 (de) | 2017-12-14 |
Family
ID=56134155
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2017/063921 WO2017211932A1 (de) | 2016-06-10 | 2017-06-08 | Cyclohexandiamine zur verwendung in der gaswäsche |
Country Status (7)
Country | Link |
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US (1) | US20190126194A1 (de) |
EP (1) | EP3468692A1 (de) |
JP (1) | JP2019520201A (de) |
AU (1) | AU2017277604A1 (de) |
CA (1) | CA3027122A1 (de) |
RU (1) | RU2019100012A (de) |
WO (1) | WO2017211932A1 (de) |
Families Citing this family (7)
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WO2018146233A1 (en) | 2017-02-10 | 2018-08-16 | Basf Se | Process for removal of acid gases from a fluid stream |
CA3061843A1 (en) | 2017-05-15 | 2018-11-22 | Basf Se | Absorbent and process for selectively removing hydrogen sulfide |
ES2952010T3 (es) * | 2019-02-18 | 2023-10-26 | Basf Se | Proceso para la eliminación de gases ácidos de una corriente de fluido con un absorbente líquido que comprende un anillo de piperazina |
WO2023018974A2 (en) * | 2021-08-13 | 2023-02-16 | The Regents Of The University Of California | Absorbent compounds for capturing carbon dioxide |
CN114452777A (zh) * | 2022-01-25 | 2022-05-10 | 江苏创新石化有限公司 | 一种炼油厂硫磺回收装置scot尾气专用超低排放脱硫溶剂 |
CA3212395A1 (en) * | 2022-04-28 | 2023-10-28 | Mitsubishi Heavy Industries, Ltd. | Composite amine absorbent, removal unit, and removal method |
DE102022116362A1 (de) | 2022-06-30 | 2024-01-04 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verfahren zur Abscheidung von Kohlenstoffdioxid |
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EP0121109A2 (de) | 1983-03-08 | 1984-10-10 | BASF Aktiengesellschaft | Verfahren zum Entfernen von C02 und/oder H2S aus Gasen |
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EP0159495A2 (de) | 1984-03-10 | 1985-10-30 | BASF Aktiengesellschaft | Verfahren zum Entfernen von C02 und/oder H2S aus Gasen |
US4553984A (en) | 1984-03-06 | 1985-11-19 | Basf Aktiengesellschaft | Removal of CO2 and/or H2 S from gases |
EP0190434A2 (de) | 1984-12-11 | 1986-08-13 | BASF Aktiengesellschaft | Verfahren zum Entfernen von Co2 und/oder H2S aus Gasen |
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US4094957A (en) * | 1976-12-14 | 1978-06-13 | Exxon Research & Engineering Co. | Process for removing acid gases with hindered amines and amino acids |
DE102007056625B3 (de) * | 2007-11-23 | 2008-09-04 | Lurgi Gmbh | Verfahren zur Behandlung eines CO2 enthaltenden Prozessgasstrom |
US9359518B2 (en) * | 2011-11-23 | 2016-06-07 | Basf Se | Aqueous binder for granular and/or fibrous substrates |
-
2017
- 2017-06-08 RU RU2019100012A patent/RU2019100012A/ru not_active Application Discontinuation
- 2017-06-08 CA CA3027122A patent/CA3027122A1/en not_active Abandoned
- 2017-06-08 AU AU2017277604A patent/AU2017277604A1/en not_active Abandoned
- 2017-06-08 JP JP2018564729A patent/JP2019520201A/ja not_active Withdrawn
- 2017-06-08 US US16/306,784 patent/US20190126194A1/en not_active Abandoned
- 2017-06-08 EP EP17728220.9A patent/EP3468692A1/de not_active Withdrawn
- 2017-06-08 WO PCT/EP2017/063921 patent/WO2017211932A1/de active Search and Examination
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EP0121109A2 (de) | 1983-03-08 | 1984-10-10 | BASF Aktiengesellschaft | Verfahren zum Entfernen von C02 und/oder H2S aus Gasen |
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EP0159495A2 (de) | 1984-03-10 | 1985-10-30 | BASF Aktiengesellschaft | Verfahren zum Entfernen von C02 und/oder H2S aus Gasen |
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EP0359991A1 (de) | 1988-08-19 | 1990-03-28 | BASF Aktiengesellschaft | Verfahren zum Entfernen von CO2 und gegebenenfalls H2S aus Gasen |
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Also Published As
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RU2019100012A3 (de) | 2020-11-18 |
RU2019100012A (ru) | 2020-07-13 |
AU2017277604A1 (en) | 2019-01-03 |
JP2019520201A (ja) | 2019-07-18 |
EP3468692A1 (de) | 2019-04-17 |
CA3027122A1 (en) | 2017-12-14 |
US20190126194A1 (en) | 2019-05-02 |
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