CA1092115A - Caustic-free process for the production of monochlorodiamino-s-triazines - Google Patents
Caustic-free process for the production of monochlorodiamino-s-triazinesInfo
- Publication number
- CA1092115A CA1092115A CA293,466A CA293466A CA1092115A CA 1092115 A CA1092115 A CA 1092115A CA 293466 A CA293466 A CA 293466A CA 1092115 A CA1092115 A CA 1092115A
- Authority
- CA
- Canada
- Prior art keywords
- triazine
- process according
- temperature
- alkylamine
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000006227 byproduct Substances 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkylamine hydrochloride Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-UHFFFAOYSA-N 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 2
- 208000036366 Sensation of pressure Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- 239000004009 herbicide Substances 0.000 abstract description 10
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JAKGSRMGAOOKEU-UHFFFAOYSA-N 2-n,4-n-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC=NC(NC(C)C)=N1 JAKGSRMGAOOKEU-UHFFFAOYSA-N 0.000 description 1
- JOZZAIIGWFLONA-UHFFFAOYSA-N 3-methylbutan-2-amine Chemical compound CC(C)C(C)N JOZZAIIGWFLONA-UHFFFAOYSA-N 0.000 description 1
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical class NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 1
- JDAPQMINSZDTBM-UHFFFAOYSA-N 4,6-dichloro-n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC(Cl)=NC(Cl)=N1 JDAPQMINSZDTBM-UHFFFAOYSA-N 0.000 description 1
- ADVLDTBFANVFFD-UHFFFAOYSA-N CCN.OCC(O)CO Chemical compound CCN.OCC(O)CO ADVLDTBFANVFFD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity 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
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BAGYZOGNODXYLV-UHFFFAOYSA-N n,n-di(propan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)N(C(C)C)C1=NC=NC=N1 BAGYZOGNODXYLV-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75303276A | 1976-12-22 | 1976-12-22 | |
| US753,032 | 1976-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092115A true CA1092115A (en) | 1980-12-23 |
Family
ID=25028865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,466A Expired CA1092115A (en) | 1976-12-22 | 1977-12-20 | Caustic-free process for the production of monochlorodiamino-s-triazines |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5379887A (cs) |
| AT (1) | AT358055B (cs) |
| AU (1) | AU518756B2 (cs) |
| BE (1) | BE862101A (cs) |
| BR (1) | BR7708540A (cs) |
| CA (1) | CA1092115A (cs) |
| CS (1) | CS194827B2 (cs) |
| DD (1) | DD133947A5 (cs) |
| DE (1) | DE2756865A1 (cs) |
| ES (1) | ES465280A1 (cs) |
| FR (1) | FR2375220A1 (cs) |
| GB (1) | GB1593169A (cs) |
| HU (1) | HU175717B (cs) |
| IL (1) | IL53667A0 (cs) |
| NL (1) | NL7713691A (cs) |
| ZA (1) | ZA776989B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1081516B (it) * | 1977-07-07 | 1985-05-21 | Rumianca Spa | Procedimetno per la produzione di cloro-bis(alchilammine)-s-triazine |
| DE2912267A1 (de) * | 1979-03-28 | 1980-10-09 | Rumianca Spa | Verfahren zur kontinuierlichen herstellung von chlor-di-(alkylamino)- s-triazinen |
| DE3171901D1 (en) * | 1980-05-30 | 1985-09-26 | Ciba Geigy Ag | Process for the preparation of amino-fluor-s-triazine dyestuffs |
| IT1204459B (it) * | 1986-02-20 | 1989-03-01 | Glaxo Spa | Derivati eterociclici |
-
1977
- 1977-11-23 ZA ZA00776989A patent/ZA776989B/xx unknown
- 1977-12-09 NL NL7713691A patent/NL7713691A/xx not_active Application Discontinuation
- 1977-12-20 DE DE19772756865 patent/DE2756865A1/de not_active Withdrawn
- 1977-12-20 DD DD77202814A patent/DD133947A5/xx unknown
- 1977-12-20 CA CA293,466A patent/CA1092115A/en not_active Expired
- 1977-12-21 BR BR7708540A patent/BR7708540A/pt unknown
- 1977-12-21 ES ES465280A patent/ES465280A1/es not_active Expired
- 1977-12-21 IL IL53667A patent/IL53667A0/xx unknown
- 1977-12-21 AT AT919977A patent/AT358055B/de not_active IP Right Cessation
- 1977-12-21 AU AU31828/77A patent/AU518756B2/en not_active Expired
- 1977-12-21 GB GB53224/77A patent/GB1593169A/en not_active Expired
- 1977-12-21 JP JP15427177A patent/JPS5379887A/ja active Pending
- 1977-12-21 BE BE183663A patent/BE862101A/xx unknown
- 1977-12-21 HU HU77CI1787A patent/HU175717B/hu unknown
- 1977-12-22 FR FR7738781A patent/FR2375220A1/fr active Granted
- 1977-12-22 CS CS778704A patent/CS194827B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD133947A5 (de) | 1979-01-31 |
| CS194827B2 (en) | 1979-12-31 |
| ZA776989B (en) | 1978-09-27 |
| JPS5379887A (en) | 1978-07-14 |
| GB1593169A (en) | 1981-07-15 |
| ATA919977A (de) | 1980-01-15 |
| BR7708540A (pt) | 1978-08-08 |
| FR2375220B1 (cs) | 1980-05-16 |
| AT358055B (de) | 1980-08-25 |
| ES465280A1 (es) | 1978-09-16 |
| BE862101A (fr) | 1978-06-21 |
| FR2375220A1 (fr) | 1978-07-21 |
| HU175717B (hu) | 1980-10-28 |
| DE2756865A1 (de) | 1978-06-29 |
| NL7713691A (nl) | 1978-06-26 |
| AU518756B2 (en) | 1981-10-22 |
| IL53667A0 (en) | 1978-03-10 |
| AU3182877A (en) | 1979-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |