DE2658657C2 - Verfahren zur Herstellung von Kresolen - Google Patents
Verfahren zur Herstellung von KresolenInfo
- Publication number
- DE2658657C2 DE2658657C2 DE2658657A DE2658657A DE2658657C2 DE 2658657 C2 DE2658657 C2 DE 2658657C2 DE 2658657 A DE2658657 A DE 2658657A DE 2658657 A DE2658657 A DE 2658657A DE 2658657 C2 DE2658657 C2 DE 2658657C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- xylenol
- cresol
- reaction
- oxide
- 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 description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000001896 cresols Chemical class 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 32
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000395 magnesium oxide Substances 0.000 claims description 20
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 17
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 9
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 9
- 150000003739 xylenols Chemical class 0.000 claims description 9
- 239000011787 zinc oxide Substances 0.000 claims description 5
- 229910000439 uranium oxide Inorganic materials 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 4
- WZECUPJJEIXUKY-UHFFFAOYSA-N [O-2].[O-2].[O-2].[U+6] Chemical compound [O-2].[O-2].[O-2].[U+6] WZECUPJJEIXUKY-UHFFFAOYSA-N 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 34
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 28
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 18
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 14
- 230000008929 regeneration Effects 0.000 description 13
- 238000011069 regeneration method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 9
- 239000012190 activator Substances 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 7
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- KHRHTUNJTHWJPV-UHFFFAOYSA-N 2,6-dimethylphenol 4-methylphenol Chemical compound CC1=C(C(=CC=C1)C)O.C1=CC(=CC=C1O)C KHRHTUNJTHWJPV-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- UFGSOCHCLHKBDB-UHFFFAOYSA-N 3,5-dimethylphenol 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=CC(O)=C1.CC1=CC(C)=C(O)C(C)=C1 UFGSOCHCLHKBDB-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940100630 metacresol Drugs 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical class CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical class CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- 150000000341 2,3-xylenols Chemical class 0.000 description 1
- KOHSRHXKURUXCP-UHFFFAOYSA-N 2,4,6-triethylphenol Chemical compound CCC1=CC(CC)=C(O)C(CC)=C1 KOHSRHXKURUXCP-UHFFFAOYSA-N 0.000 description 1
- 150000000343 2,5-xylenols Chemical class 0.000 description 1
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- -1 Uranium oxide activated magnesium oxide Chemical class 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by exchange of hydrocarbon groups, which may be substituted, from the same of other compounds, e.g. transalkylation
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/670,772 US4060560A (en) | 1976-03-26 | 1976-03-26 | Disproportionation of xylenols with phenol to form cresols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2658657A1 DE2658657A1 (de) | 1977-09-29 |
| DE2658657C2 true DE2658657C2 (de) | 1986-04-10 |
Family
ID=24691803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2658657A Expired DE2658657C2 (de) | 1976-03-26 | 1976-12-23 | Verfahren zur Herstellung von Kresolen |
Country Status (9)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110253A (en) * | 1977-01-24 | 1978-08-29 | Continental Oil Company | Method for the disproportionation of highly alkylated phenols with phenol |
| US4269735A (en) * | 1980-01-21 | 1981-05-26 | Conoco, Inc. | Magnesium oxide catalyst |
| US4359408A (en) * | 1981-06-04 | 1982-11-16 | Conoco Inc. | Activated magnesium oxide catalysts |
| US4476329A (en) * | 1983-04-04 | 1984-10-09 | General Electric Company | Selective alkylation of phenol to o-cresol |
| US4533767A (en) * | 1984-05-03 | 1985-08-06 | General Electric Company | Catalytic hydrodealkylation of alkylated phenols |
| US4533768A (en) * | 1984-05-03 | 1985-08-06 | General Electric Company | Zinc oxide catalyzed dealkylation of alkylated phenols |
| US8722557B2 (en) * | 2008-12-30 | 2014-05-13 | Lyondell Chemical Technology, L.P. | Catalyst regeneration |
| CN103896740B (zh) * | 2012-12-25 | 2016-08-10 | 中国科学院大连化学物理研究所 | 一种生产甲酚的方法 |
| US11485694B2 (en) | 2019-02-04 | 2022-11-01 | China Petroleum & Chemical Corporation | Dealklylation and transalkylation of mixed phenols to make cresols |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2295675A (en) * | 1937-09-14 | 1942-09-15 | Bakelite Corp | Dealkylation using barium, cadmium, and zinc compounds as catalysts |
| US2446856A (en) * | 1943-10-16 | 1948-08-10 | Univ Minnesota | Method of treating phenols |
| GB695464A (en) * | 1950-06-23 | 1953-08-12 | C U R A Patents Ltd | Improvements relating to the manufacture of phenols |
| US2777881A (en) * | 1952-08-06 | 1957-01-15 | Consolidation Coal Co | Catalytic conversion of methyl phenols |
| US3446856A (en) * | 1964-05-29 | 1969-05-27 | Gen Electric | Methylation of phenols |
| US3417149A (en) * | 1966-03-16 | 1968-12-17 | Consolidation Coal Co | Transmethylation of methylsubstituted phenols |
| US3479410A (en) * | 1967-05-18 | 1969-11-18 | Gen Electric | Selective vapor phase methylation of phenols |
| GB1232027A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-08-16 | 1971-05-19 | ||
| GB1291191A (en) * | 1970-01-08 | 1972-10-04 | Chemische Werke Lowi Ges Mit B | Process for the isomerization and disproportioning of methyl phenols |
| US3998892A (en) * | 1975-11-17 | 1976-12-21 | Continental Oil Company | Preparation of prehnitenol |
-
1976
- 1976-03-26 US US05/670,772 patent/US4060560A/en not_active Expired - Lifetime
- 1976-12-21 NL NL7614226A patent/NL7614226A/xx not_active Application Discontinuation
- 1976-12-22 GB GB53559/76A patent/GB1500676A/en not_active Expired
- 1976-12-23 JP JP51154362A patent/JPS6030658B2/ja not_active Expired
- 1976-12-23 DE DE2658657A patent/DE2658657C2/de not_active Expired
- 1976-12-23 FR FR7638915A patent/FR2345418A1/fr active Granted
- 1976-12-28 BE BE173672A patent/BE849900A/xx not_active IP Right Cessation
-
1977
- 1977-01-20 CA CA270,269A patent/CA1081259A/en not_active Expired
- 1977-03-25 CH CH384277A patent/CH602532A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2345418B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-01-07 |
| GB1500676A (en) | 1978-02-08 |
| DE2658657A1 (de) | 1977-09-29 |
| BE849900A (fr) | 1977-06-28 |
| JPS6030658B2 (ja) | 1985-07-17 |
| JPS52116429A (en) | 1977-09-29 |
| NL7614226A (nl) | 1977-09-28 |
| FR2345418A1 (fr) | 1977-10-21 |
| CH602532A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-31 |
| CA1081259A (en) | 1980-07-08 |
| US4060560A (en) | 1977-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: CONOCO INC., 74601 PONCA CITY, OKLA., US |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |