US1281662A - Method for the production of guaiacol. - Google Patents
Method for the production of guaiacol. Download PDFInfo
- Publication number
- US1281662A US1281662A US14106717A US14106717A US1281662A US 1281662 A US1281662 A US 1281662A US 14106717 A US14106717 A US 14106717A US 14106717 A US14106717 A US 14106717A US 1281662 A US1281662 A US 1281662A
- Authority
- US
- United States
- Prior art keywords
- guaiacol
- pyrocatechin
- veratrol
- production
- grams
- 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
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 title description 20
- 238000000034 method Methods 0.000 title description 14
- 229960001867 guaiacol Drugs 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 3
- 239000012022 methylating agents Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001327708 Coriaria sarmentosa Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001071861 Lethrinus genivittatus Species 0.000 description 1
- 241001446467 Mama Species 0.000 description 1
- CCAZWUJBLXKBAY-ULZPOIKGSA-N Tutin Chemical compound C([C@]12[C@@H]3O[C@@H]3[C@@]3(O)[C@H]4C(=O)O[C@@H]([C@H]([C@]32C)O)[C@H]4C(=C)C)O1 CCAZWUJBLXKBAY-ULZPOIKGSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Definitions
- Our invention relates to a method for producing guaiacol from pyrocatechin.
- pyrocatechin could be methylated by means of methyl sulfuric acid or its alkali salts; for instance, Gorup-Besanez (Ann. 147. 2 17.) has described such a method.
- t e yield of guaiacol is so poor that a commercial applieation of said method is not feasible.
- energetic methylating means are employed, as for instance dimethyl sulfate,
- the herein described method of producing guaiacol from pyrocatechin which comprises subjecting the pyrocatechin to the action of an alkali salt of methyl sulfuric acid in the presence of veratrol, and adding a weak alkali metal compound to the material under treatment, while the mixture is held at a temperature of substantially 160 to 180 degrees.
- guaiacol which comprises subjecting pyrocatechin to the action of a methylating agent, in the presence or veratrol, and adding a weal: alkali metal compound.
- the method of producing guaiacol from pyrocatechin which comprises subjecting the pyrccatechin to the action of a methylating agent in the presence or veratrol at a tempyrocatechin which comprises subjecting the pyrocatechin to the action of a salt of methyl sulfuric acid in the presence of veratrol, adding a weakly alkaline compound while the mixture is held at a temperature of substantially 160 to 180' degrees coclin and acidifying the reaction product, distil ating the reaction product and separating the guaiacol from the distillate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- ll'ftllTED nnrrs'rn. sotnrnenn, or aonrcn, swrrznanann, nun near/ram:
tutu/"norms, Wisconsin.
nonnative, or"
METHQED 3P0 tiff-IE FROIDUGTXGH F QUAIAGQL,
Ho Drawing.
To all whom may concern:
Be it known that we, Euns'r id. Zonnrnenn and HERMANTN Ronrrmnc, citizens, respectively, of the Republic of Switzerland and the United States, residing. respectively, at Zurich, in the Republic of Switzerland, and
- at Milwaukee, State of Wisconsin, U. S. A,
have invented a certain new and useful Tl provement in Methods for the Production of Guaiacol, of which the following is a full, clear, concise, and exact description.
Our invention relates to a method for producing guaiacol from pyrocatechin. Prior to our invention of the process hereinaf er claimed it was known that pyrocatechin could be methylated by means of methyl sulfuric acid or its alkali salts; for instance, Gorup-Besanez (Ann. 147. 2 17.) has described such a method. Accordin to the Gorup-Besanez method, however, t e yield of guaiacol is so poor that a commercial applieation of said method is not feasible. Ti, however, energetic methylating means are employed, as for instance dimethyl sulfate,
which in view of its exceedingly poisonous qualities is little used for technical purposes, veratrol is produced in great quantities. (Ulhnann Amt. 327. 10 i, Per/ 0in and Weds mama Zentmlblatt 07. i; 406.)
We have found that when pyrocatechin and potassium methyl sulfate are intimately mixed and melted in the presence of veratrol guaiacol is produced in considerable quantities provided a weak alkaline compound, such as carbonate or bicarbonate of sodium is gradually added to the mixture. The great advantage of this method is obvious when consideration is given to the fact that pyrocatechin is inclined to undergo considerable changes in alkaline watery solutions. This method whereby we methylate pyrocatechin in veratrol as a solvent at a temperature of 180 degrees has the advantage that only one hydroxyl' group is methylated in a yield exceeding 85 per cent. The folmama Specification of Eetters Patent.
net, as, rare.
' application filed January 8, 153.7". ijerialfio. lancer. i
lowin exam is will sufficientl illustrateour improved method.
Eammple.
11 grams of pyrocatechin are intimately grated with 25 grams of potassium methyl sulfate and mixed with 15 grams of vera-' trol. To this mixture 25 grams of sodium bicarbonate is added in portions during two hours at a temperature of 169 to 180 degrees. Upon getting cold, the reaction product is acidified and subjected to a steam distillation. From this distillate the guaiacol as well as the unchanged veratrol is recovered, according to known methods. The yield of guaiaccl amounts to 10.5 grams.
What we claim as new and desire to secure by Letters Patent of the United States is: v
1. The herein described method of producing guaiacol from pyrocatechin, which comprises subjecting the pyrocatechin to the action of an alkali salt of methyl sulfuric acid in the presence of veratrol, and adding a weak alkali metal compound to the material under treatment, while the mixture is held at a temperature of substantially 160 to 180 degrees.
. 2. The herein described method of producing guaiacol, which comprises subjecting pyrocatechin to the action of a methylating agent, in the presence or veratrol, and adding a weal: alkali metal compound.
3, The method of producing guaiacol from pyrocatechin which comprises subjecting the pyrccatechin to the action of a methylating agent in the presence or veratrol at a tempyrocatechin which comprises subjecting the pyrocatechin to the action of a salt of methyl sulfuric acid in the presence of veratrol, adding a weakly alkaline compound while the mixture is held at a temperature of substantially 160 to 180' degrees coclin and acidifying the reaction product, distil ating the reaction product and separating the guaiacol from the distillate.
5. The herein described method of proweakly alkaline compound while the mixture 10 is maintained at a temperature causing a reaction of the methylating agent with the pyrocatechin.
In W1tness whereof ERNST H ZOLLINGER has hereunto subscribed his name this 14th day of March, A. D. 1917.
' ERNST H. ZOLLINGER. In witness whereof HERMANN ROEHLING has hereunto subscribed his name this 5 day of May, A. D. 1917. HERMANN BOEHLING.
Oopies of this patent may be obtained tor five cents each, by addressing the fGommissioner o1 Batents,
' Washington, D. 0. i
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14106717A US1281662A (en) | 1917-01-06 | 1917-01-06 | Method for the production of guaiacol. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14106717A US1281662A (en) | 1917-01-06 | 1917-01-06 | Method for the production of guaiacol. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1281662A true US1281662A (en) | 1918-10-15 |
Family
ID=3349252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14106717A Expired - Lifetime US1281662A (en) | 1917-01-06 | 1917-01-06 | Method for the production of guaiacol. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1281662A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801268A (en) * | 1957-07-30 | Method of making z-tertiarybutyl-x- | ||
| US2887515A (en) * | 1959-05-19 | Preparation of tertiary butyl-x- |
-
1917
- 1917-01-06 US US14106717A patent/US1281662A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801268A (en) * | 1957-07-30 | Method of making z-tertiarybutyl-x- | ||
| US2887515A (en) * | 1959-05-19 | Preparation of tertiary butyl-x- |
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