CA1058220A - Manufacture of formaldehyde - Google Patents
Manufacture of formaldehydeInfo
- Publication number
- CA1058220A CA1058220A CA233,565A CA233565A CA1058220A CA 1058220 A CA1058220 A CA 1058220A CA 233565 A CA233565 A CA 233565A CA 1058220 A CA1058220 A CA 1058220A
- Authority
- CA
- Canada
- Prior art keywords
- methanol
- per
- catalyst
- mole
- gas
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 105
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 264
- 239000003054 catalyst Substances 0.000 claims abstract description 111
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000008569 process Effects 0.000 claims abstract description 39
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052709 silver Inorganic materials 0.000 claims abstract description 16
- 239000004332 silver Substances 0.000 claims abstract description 16
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims abstract description 11
- 239000007789 gas Substances 0.000 claims description 67
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000008246 gaseous mixture Substances 0.000 claims description 2
- 229940105305 carbon monoxide Drugs 0.000 claims 2
- 208000036366 Sensation of pressure Diseases 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000000645 desinfectant Substances 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 239000004826 Synthetic adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 description 24
- 229960004279 formaldehyde Drugs 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 230000009102 absorption Effects 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000011261 inert gas Substances 0.000 description 11
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 11
- 239000006200 vaporizer Substances 0.000 description 10
- 239000008098 formaldehyde solution Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000009434 installation Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XDJWZONZDVNKDU-UHFFFAOYSA-N 1314-24-5 Chemical compound O=POP=O XDJWZONZDVNKDU-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 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
- 230000002844 continuous effect Effects 0.000 description 1
- -1 hydrogèn Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442231A DE2442231C2 (de) | 1974-09-04 | 1974-09-04 | Verfahren zur Herstellung von Formaldehyd |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058220A true CA1058220A (en) | 1979-07-10 |
Family
ID=5924799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,565A Expired CA1058220A (en) | 1974-09-04 | 1975-08-15 | Manufacture of formaldehyde |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4072717A (enExample) |
| JP (1) | JPS5833846B2 (enExample) |
| BE (1) | BE833029A (enExample) |
| CA (1) | CA1058220A (enExample) |
| DE (1) | DE2442231C2 (enExample) |
| FR (1) | FR2283882A1 (enExample) |
| GB (1) | GB1510856A (enExample) |
| IT (1) | IT1041827B (enExample) |
| ZA (1) | ZA755572B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4315799A1 (de) * | 1993-05-12 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Formyldehyd durch oxidative Dehydrierung von Methanol in Gegenwart von Distickstoffoxid |
| US6147263A (en) * | 1998-04-30 | 2000-11-14 | Lehigh University | Formaldehyde production |
| FR2900925B1 (fr) * | 2006-05-09 | 2008-10-17 | Arkema France | Procede de fabrication de produits d'oxydation partielle d'alcools inferieurs par oxydation directe d'un alcool inferieur |
| WO2014097873A1 (ja) | 2012-12-18 | 2014-06-26 | 花王株式会社 | アルデヒドの製造方法 |
| GB201502894D0 (en) | 2015-02-20 | 2015-04-08 | Johnson Matthey Plc | Process |
| GB201502893D0 (en) * | 2015-02-20 | 2015-04-08 | Johnson Matthey Plc | Process |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2436287A (en) * | 1943-04-15 | 1948-02-17 | Du Pont | Conversion of methanol to formaldehyde |
| US2462413A (en) * | 1946-06-06 | 1949-02-22 | Allied Chem & Dye Corp | Production of formaldehyde |
| FR2038646A5 (enExample) * | 1969-03-20 | 1971-01-08 | Charbonnages Chimiques | |
| IT988916B (it) * | 1972-06-26 | 1975-04-30 | Basf Ag | Processo per la preparazione di formaldeide |
-
1974
- 1974-09-04 DE DE2442231A patent/DE2442231C2/de not_active Expired
-
1975
- 1975-08-12 IT IT26318/75A patent/IT1041827B/it active
- 1975-08-15 CA CA233,565A patent/CA1058220A/en not_active Expired
- 1975-08-22 US US05/606,773 patent/US4072717A/en not_active Expired - Lifetime
- 1975-09-02 JP JP50105680A patent/JPS5833846B2/ja not_active Expired
- 1975-09-02 ZA ZA00755572A patent/ZA755572B/xx unknown
- 1975-09-03 FR FR7527005A patent/FR2283882A1/fr active Granted
- 1975-09-03 BE BE159710A patent/BE833029A/xx not_active IP Right Cessation
- 1975-09-03 GB GB36221/75A patent/GB1510856A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5833846B2 (ja) | 1983-07-22 |
| FR2283882B1 (enExample) | 1980-11-07 |
| GB1510856A (en) | 1978-05-17 |
| BE833029A (fr) | 1976-03-03 |
| DE2442231A1 (de) | 1976-03-18 |
| JPS5154507A (en) | 1976-05-13 |
| FR2283882A1 (fr) | 1976-04-02 |
| ZA755572B (en) | 1976-08-25 |
| DE2442231C2 (de) | 1982-04-01 |
| IT1041827B (it) | 1980-01-10 |
| US4072717A (en) | 1978-02-07 |
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