US3350463A - Process for the manufacture of esters of orthoformic acid with alkanols with 2 to 6 carbon atoms - Google Patents
Process for the manufacture of esters of orthoformic acid with alkanols with 2 to 6 carbon atoms Download PDFInfo
- Publication number
- US3350463A US3350463A US426445A US42644565A US3350463A US 3350463 A US3350463 A US 3350463A US 426445 A US426445 A US 426445A US 42644565 A US42644565 A US 42644565A US 3350463 A US3350463 A US 3350463A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- esters
- acid
- orthoformic acid
- alkanol
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/60—Preparation of compounds having groups or groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K20/00—Non-electric welding by applying impact or other pressure, with or without the application of heat, e.g. cladding or plating
- B23K20/06—Non-electric welding by applying impact or other pressure, with or without the application of heat, e.g. cladding or plating by means of high energy impulses, e.g. magnetic energy
- B23K20/08—Explosive welding
Definitions
- orthoformic acid esters of lower alkanols can be re-esterfied to form orthoesters of higher alkanols.
- the orthoformic acid esthers of the lower alkanol is boiled with the higher alkanol with reflux, so that the low alkanol that is released during the slow process of re-esterification is drawn oif at the head.
- Re-esterification under the above conditions is so slow that the process is uneconomicalit takes days to perform.
- the addition of sulfuric acid has been proposed for the purpose of accelerating this re-esterification reaction.
- esters of orthoformic acid with alkanols having 2 to 6 carbon atoms from orthoformic acid trimethyl ester with with alkanols having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, in the presence of 001 to 1 weight-percent, and preferably 0.04 to 0.6 weightormic acid.
- the percentage of formic acid added is based on the total amount of the reactants.
- the re-esterification equilibrium is established within a short time. Then the released ing composition can be ad usted, whereupon the percentage of the triester of the higher alkanol increases in such a manner that separation of the starting ester and the intermediate esters by distillation is economical.
- An elevated temperature can be used.
- the reactants can be heated to any temperature up to the boiling point of the mixture. It is desirable, however, to employ room temperature for the reaction.
- the reactants can be left at room temperature until the new equilibrium for the reactants is established. This will commonly require a period of hours, for example 1-3 hours.
- the process of the invention can also be performed continuously, if desired.
- the alkauols, the starting ester and the intermediate esters are removed at the top, while the desired triester remains in the sump of the column.
- the head product can then be fed back into the process at an appropriate point.
- Example 1 Equivalent amounts of orthoformic acid trimethyl ester (106 grams) and ethanol (138 grams) are combined with 0.12 gram of formic acid and thoroughly mixed together until homogeneous. After two hours the re-esterification equilibrium has established itself. The mixture then contams orthoformic acid triethyl ester, orthoformic acid the remaining has the highest amounts to more than to the orthoformic acid.
- Orthoformic acid triisopropyl ester 636 grams of orthoformic acid trimethyl ester are thorremainder produces 800 to 880 grams (70 to 77% of the theory) of orthoformic acid triisopropyl ester.
- Example 3 Orthoformic acid tributyl ester: 530 grams of orthoformic grams of Torr produces about 1060 of the theory) of orthoformic acid tributyl ester.
- Example 4 Orthoformic acid tripropyl ester: Equivalent quantities of trimethyl orthoformate and nmixed with 0.06% formic acid.
- the head product contains mainly n-propanol, the intermediate esters and tripropyl orthoformate, plus a little methanol.
- Process for the manufacture of a triester of orthoformic acid and an alkanol having 2-6 carbon atoms by liquid phase reaction which comprises contacting orthoformic acid trimethyl ester with an alkanol having 2-6 carbon atoms in the presence of 0.01-1 wt. percent of formic acid based on the total amount of the reactants, at a temperature and for a time sufficient for formation in said liquid phase of said triester of orthoformic acid and. alkanol containing 2-6 carbon atoms, methyl alcohol, and esters of said formic acid, and separating methyl alcohol and said esters of formic acid from said liquid phase by distillation.
- Process according to claim is ethanol, isopropanol, n-butanol,
- Process according to claim is ethanol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1964D0043383 DE1205076C2 (de) | 1964-01-18 | 1964-01-18 | Verfahren zur Herstellung von Estern der Orthoameisensaeure mit Alkanolen mit 2 bis 6 Kohlenstoffatomen |
Publications (1)
Publication Number | Publication Date |
---|---|
US3350463A true US3350463A (en) | 1967-10-31 |
Family
ID=7047536
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US426445A Expired - Lifetime US3350463A (en) | 1964-01-18 | 1965-01-18 | Process for the manufacture of esters of orthoformic acid with alkanols with 2 to 6 carbon atoms |
Country Status (8)
Country | Link |
---|---|
US (1) | US3350463A (de) |
BE (1) | BE658411A (de) |
CH (1) | CH447137A (de) |
DE (1) | DE1205076C2 (de) |
FR (1) | FR1420966A (de) |
GB (1) | GB1029092A (de) |
LU (1) | LU47801A1 (de) |
NL (2) | NL6500507A (de) |
-
0
- BE BE658411D patent/BE658411A/xx unknown
-
1964
- 1964-01-18 DE DE1964D0043383 patent/DE1205076C2/de not_active Expired
-
1965
- 1965-01-14 CH CH50965A patent/CH447137A/de unknown
- 1965-01-15 FR FR2076A patent/FR1420966A/fr not_active Expired
- 1965-01-15 NL NL6500507A patent/NL6500507A/xx unknown
- 1965-01-15 LU LU47801A patent/LU47801A1/xx unknown
- 1965-01-15 GB GB2013/65A patent/GB1029092A/en not_active Expired
- 1965-01-15 NL NL656500506A patent/NL143834B/xx unknown
- 1965-01-18 US US426445A patent/US3350463A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
None * |
Also Published As
Publication number | Publication date |
---|---|
DE1205076B (de) | 1965-11-18 |
NL6500506A (de) | 1965-07-19 |
CH447137A (de) | 1967-11-30 |
GB1029092A (en) | 1966-05-11 |
BE658411A (de) | |
NL6500507A (de) | 1965-07-19 |
FR1420966A (fr) | 1965-12-10 |
DE1205076C2 (de) | 1973-07-05 |
NL143834B (nl) | 1974-11-15 |
LU47801A1 (de) | 1965-03-15 |
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