CA2331663A1 - Oxydation regulee d'hydrocarbures en produits d'oxydation intermediaires - Google Patents
Oxydation regulee d'hydrocarbures en produits d'oxydation intermediaires Download PDFInfo
- Publication number
- CA2331663A1 CA2331663A1 CA002331663A CA2331663A CA2331663A1 CA 2331663 A1 CA2331663 A1 CA 2331663A1 CA 002331663 A CA002331663 A CA 002331663A CA 2331663 A CA2331663 A CA 2331663A CA 2331663 A1 CA2331663 A1 CA 2331663A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- acid
- polyamide
- cyclohexane
- xylene
- 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.)
- Abandoned
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 112
- 230000003647 oxidation Effects 0.000 title claims abstract description 111
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 59
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 214
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 158
- 238000006243 chemical reaction Methods 0.000 claims abstract description 117
- 239000007789 gas Substances 0.000 claims abstract description 110
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 106
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 102
- 239000001301 oxygen Substances 0.000 claims abstract description 97
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 96
- 239000001361 adipic acid Substances 0.000 claims abstract description 79
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 79
- 238000001816 cooling Methods 0.000 claims abstract description 64
- 239000002253 acid Substances 0.000 claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007788 liquid Substances 0.000 claims abstract description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 239000011261 inert gas Substances 0.000 claims abstract description 20
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 114
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 82
- 239000004952 Polyamide Substances 0.000 claims description 59
- 229920002647 polyamide Polymers 0.000 claims description 59
- 239000004215 Carbon black (E152) Substances 0.000 claims description 47
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 41
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 40
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 38
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 38
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 36
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 36
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 36
- 239000000835 fiber Substances 0.000 claims description 30
- 229920000768 polyamine Polymers 0.000 claims description 30
- 229920000728 polyester Polymers 0.000 claims description 30
- 229920005862 polyol Polymers 0.000 claims description 30
- 150000003077 polyols Chemical class 0.000 claims description 30
- 239000004962 Polyamide-imide Substances 0.000 claims description 29
- 239000004642 Polyimide Substances 0.000 claims description 29
- 239000000654 additive Substances 0.000 claims description 29
- 239000002131 composite material Substances 0.000 claims description 29
- 239000000945 filler Substances 0.000 claims description 29
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims description 29
- 238000002156 mixing Methods 0.000 claims description 29
- 229920002312 polyamide-imide Polymers 0.000 claims description 29
- 229920001721 polyimide Polymers 0.000 claims description 29
- 239000000376 reactant Substances 0.000 claims description 29
- 238000009987 spinning Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229940078552 o-xylene Drugs 0.000 claims description 18
- 238000004064 recycling Methods 0.000 claims description 6
- 238000010907 mechanical stirring Methods 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 abstract description 12
- 230000008569 process Effects 0.000 description 33
- 239000000047 product Substances 0.000 description 29
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 22
- 238000010926 purge Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 13
- 239000001569 carbon dioxide Substances 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000001590 oxidative effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000012886 linear function Methods 0.000 description 8
- 238000013461 design Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- 150000001868 cobalt Chemical class 0.000 description 6
- 239000000498 cooling water Substances 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000013459 approach Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000004880 explosion Methods 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- -1 cyclic alcohols Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- DQSJGBWCBXHQCT-UHFFFAOYSA-N 6-cyclohexyloxy-6-oxohexanoic acid Chemical class OC(=O)CCCCC(=O)OC1CCCCC1 DQSJGBWCBXHQCT-UHFFFAOYSA-N 0.000 description 2
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 238000013528 artificial neural network Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- RPYFZMPJOHSVLD-UHFFFAOYSA-N copper vanadium Chemical compound [V][V][Cu] RPYFZMPJOHSVLD-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000004200 deflagration Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention porte sur des procédés régulant l'oxydation d'hydrocarbures en leurs produits d'oxydation intermédiaires respectifs, par exemple des acides dibasiques, en ajustant la température du bain en cours d'oxydation à l'aide d'un élément refroidissant dont la température est maintenue au-dessus du niveau où les solides se déposent sur l'élément, et/ou en maintenant la concentration d'oxygène dans les gaz effluents du condenseur à un niveau de préférence inférieur à 90 % en volume de la concentration en oxygène inflammable, et/ou en fournissant de l'oxygène et un gaz inerte (de préférence de l'azote) à la zone de réaction, le gaz inerte et l'oxygène étant de préférence dans un rapport GI/O allant de 1:5 à 1:200. L'invention s'applique en particulier à l'oxydation directe du cyclohexane en acide adipique.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8611998P | 1998-05-20 | 1998-05-20 | |
| US8615998P | 1998-05-20 | 1998-05-20 | |
| US8611898P | 1998-05-20 | 1998-05-20 | |
| US60/086,118 | 1998-05-20 | ||
| US60/086,159 | 1998-05-20 | ||
| US60/086,119 | 1998-05-20 | ||
| US10191898P | 1998-09-24 | 1998-09-24 | |
| US60/101,918 | 1998-09-24 | ||
| PCT/US1999/008296 WO1999059953A1 (fr) | 1998-05-20 | 1999-04-15 | Oxydation regulee d'hydrocarbures en produits d'oxydation intermediaires |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2331663A1 true CA2331663A1 (fr) | 1999-11-25 |
Family
ID=27492018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002331663A Abandoned CA2331663A1 (fr) | 1998-05-20 | 1999-04-15 | Oxydation regulee d'hydrocarbures en produits d'oxydation intermediaires |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1080064A1 (fr) |
| JP (1) | JP2002515473A (fr) |
| KR (1) | KR20010052376A (fr) |
| CN (1) | CN1307555A (fr) |
| AU (1) | AU3646399A (fr) |
| BR (1) | BR9910513A (fr) |
| CA (1) | CA2331663A1 (fr) |
| MX (1) | MXPA00011514A (fr) |
| WO (1) | WO1999059953A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949673B2 (en) | 2000-01-12 | 2005-09-27 | E.I. Du Pont De Nemours And Company | Process for producing carboxylic acids |
| US7060853B2 (en) | 2000-01-12 | 2006-06-13 | Invista North America S.A R.L. | Method for increasing oxidation reactor production capacity |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| JP6883696B1 (ja) * | 2020-11-16 | 2021-06-09 | 株式会社日本触媒 | 第２級アルコールの製造方法 |
| CN117326928A (zh) * | 2022-06-24 | 2024-01-02 | 中国石油化工股份有限公司 | 尾气回用的环己烷氧化的方法和产物及系统 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439513A (en) * | 1945-11-30 | 1948-04-13 | Du Pont | Adipic acid process |
| US3869508A (en) * | 1968-12-13 | 1975-03-04 | Witco Chemical Corp | Process of producing adipic acid |
| US5883292A (en) * | 1996-01-17 | 1999-03-16 | Twenty-First Century Research Corporation | Reaction control by regulating internal condensation inside a reactor |
-
1999
- 1999-04-15 CA CA002331663A patent/CA2331663A1/fr not_active Abandoned
- 1999-04-15 BR BR9910513-6A patent/BR9910513A/pt not_active Application Discontinuation
- 1999-04-15 EP EP99918587A patent/EP1080064A1/fr not_active Withdrawn
- 1999-04-15 KR KR1020007013045A patent/KR20010052376A/ko not_active Withdrawn
- 1999-04-15 WO PCT/US1999/008296 patent/WO1999059953A1/fr not_active Ceased
- 1999-04-15 JP JP2000549572A patent/JP2002515473A/ja not_active Withdrawn
- 1999-04-15 CN CN99807609A patent/CN1307555A/zh active Pending
- 1999-04-15 AU AU36463/99A patent/AU3646399A/en not_active Abandoned
- 1999-04-15 MX MXPA00011514A patent/MXPA00011514A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA00011514A (es) | 2002-04-24 |
| BR9910513A (pt) | 2001-09-04 |
| EP1080064A1 (fr) | 2001-03-07 |
| AU3646399A (en) | 1999-12-06 |
| CN1307555A (zh) | 2001-08-08 |
| JP2002515473A (ja) | 2002-05-28 |
| WO1999059953A1 (fr) | 1999-11-25 |
| KR20010052376A (ko) | 2001-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |