US841999A - Process of making formaldehyde sulfoxylates. - Google Patents
Process of making formaldehyde sulfoxylates. Download PDFInfo
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- US841999A US841999A US30703206A US1906307032A US841999A US 841999 A US841999 A US 841999A US 30703206 A US30703206 A US 30703206A US 1906307032 A US1906307032 A US 1906307032A US 841999 A US841999 A US 841999A
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- US
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- sulfoxylates
- formaldehyde
- acetone
- formaldehyde sulfoxylates
- making formaldehyde
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
Definitions
- Ph. D., and WOLDEMAR W LLENBER Phl- D chemists citizens of the Empire of Germany, residing at H6chst-onthe-Main, Ger many,,have invented certain new and useful Improvements in Formaldehyde Sulfoxylates and Processes of Making Same, of which the following is a specification. v
- ketone s'ulfoxylates can also be produced by reducing the products of reaction of bisulfites, sulfurous acid, or hydro sulfite on acetone or ethylmethylketone or by subject'- ing these compounds to reduction in press ence of said ketones;
- the ketone sulfoxylates are obtained, for instance, as follows: Into asolution of sixtyfive parts of acetone in one thousand parts of water are introduced sixty-four parts of sul- 2 5 fur dioxid. One hundred and twenty parts of zinc-dust are thcn'addedwhile stirring and well cooling, and if no further spontaneous heating occurs thetemperature is raised to 50 to 60 ccntigrade. After heating for some hours a solution of acetone .zinc sulfoxylate is obtained, which when treated with sodium carbonate is transformed int acetone sodium sulfoxylate. v
- the rocess for obtaining formaldehyde sulfoxy ate from ketone sulfoxylates may be carried out, for instance, as follows: To a solution containing one hundred and forty parts of acetone sodium sulfoxylate of one hundred percent. strength in one liter of water are added while stirring seventy five parts of formaldehyde of fortyper -cent. strength. -The combination occurs rapidly, and the formaldehyde sodium sulfoxylate may then be obtained in solid form by evaporating in a vacuum, While the acetone is dis tilled ofi.
- other salts-such, for instance, as the zinc salt- may be used in a like manner.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
RUDOLF Mf'lLL-ER AND .-WOLDEMAR WOLLENBERG, or Hooiisr oN-THE- MAIN, GERMANY, AssicNoRs TO FARBWERKE, V-ORM. MEisrEa' LUCIUS & BRUNIN'G, OF HOGHST-ONJIHE-MAIN,'GERMANY, A CORPO- RATION OF GERMANY.
- PROCESS OF-MAKING: YFORMALDIEHYDE SULFOXYLATES.
Specification of Letters Patent. I
Patented. J an. 22, 1907.
Application filed March 20,1906. vi Serial N el 307.032. (Specimens) To all mil/m it may concern.-
Be it known that we, RUDoLF Mt'in En,
Ph. D., and WOLDEMAR W LLENBER Phl- D chemists, citizens of the Empire of Germany, residing at H6chst-onthe-Main, Ger many,,have invented certain new and useful Improvements in Formaldehyde Sulfoxylates and Processes of Making Same, of which the following is a specification. v
As by the action of formaldehyde on h drosulfite 'ketone sulfoxylates mayv also ev obtained by the action ofacetqne or ethylmeth lketone on alkaline hydrosulfites, which may e isolated afterward. by crystallization is These ketone s'ulfoxylates can also be produced by reducing the products of reaction of bisulfites, sulfurous acid, or hydro sulfite on acetone or ethylmethylketone or by subject'- ing these compounds to reduction in press ence of said ketones;
The ketone sulfoxylates are obtained, for instance, as follows: Into asolution of sixtyfive parts of acetone in one thousand parts of water are introduced sixty-four parts of sul- 2 5 fur dioxid. One hundred and twenty parts of zinc-dust are thcn'addedwhile stirring and well cooling, and if no further spontaneous heating occurs thetemperature is raised to 50 to 60 ccntigrade. After heating for some hours a solution of acetone .zinc sulfoxylate is obtained, which when treated with sodium carbonate is transformed int acetone sodium sulfoxylate. v
We have found that lretone sulfoxylates may be transformed into the more stable formaldehyde sulfoxylates if the former are treated with formaldehyde. By the action of the formaldehyde on kctonc sulfoxylatcs' theketone is eliminated with formation of 4 formaldehyde sulfoxylate, which is readily observed in that thesolution of the ketone sulfoxylates treated with the equivalent proportion offormaldehyde no longer reduces indigo-sulfonic acid in the cold. The reaction of this process may be interpreted by the following equation:
The rocess for obtaining formaldehyde sulfoxy ate from ketone sulfoxylates may be carried out, for instance, as follows: To a solution containing one hundred and forty parts of acetone sodium sulfoxylate of one hundred percent. strength in one liter of water are added while stirring seventy five parts of formaldehyde of fortyper -cent. strength. -The combination occurs rapidly, and the formaldehyde sodium sulfoxylate may then be obtained in solid form by evaporating in a vacuum, While the acetone is dis tilled ofi. For the acetone sodium sulfoxylate other salts-such, for instance, as the zinc salt-may be used in a like manner.
Having now described our invention, what' we claim'is 1. The herein-described process for the manufacture of formaldehyde sulfoxylates, which consists in treating the sulfoxylates of ketones having the. formula CH COX, wherein X means methyl or ethyl, with formaldeiyde. 2. The herein-described process for the "manufacture of formaldehyde sulfoxylates, which consists in treating the sulfoxylates of acetone with formaldehyde.
In testimony that we claim the foregoing as our invention we have signed our names in preseni ze of two subscribing witnesses.
\ UDOLF MULLER.
VVOLDEMAR VVOLLENBERG. Witnesses:
JEAN GRUND,
CAPL GR ND.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30703206A US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30703206A US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
Publications (1)
Publication Number | Publication Date |
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US841999A true US841999A (en) | 1907-01-22 |
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Application Number | Title | Priority Date | Filing Date |
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US30703206A Expired - Lifetime US841999A (en) | 1906-03-20 | 1906-03-20 | Process of making formaldehyde sulfoxylates. |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3248278A (en) * | 1962-02-16 | 1966-04-26 | Pritchard & Co J F | Method of recovering monovalent cations from spent monovalent cation sulfite pulpingliquor |
US4657593A (en) * | 1981-11-10 | 1987-04-14 | Skw Trostberg Aktiengesellschaft | Modifying surface tension of finely-divided materials in a liquid |
US4818288A (en) * | 1983-12-07 | 1989-04-04 | Skw Trostberg Aktiengesellschaft | Dispersant for concrete mixtures of high salt content |
-
1906
- 1906-03-20 US US30703206A patent/US841999A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3248278A (en) * | 1962-02-16 | 1966-04-26 | Pritchard & Co J F | Method of recovering monovalent cations from spent monovalent cation sulfite pulpingliquor |
US4657593A (en) * | 1981-11-10 | 1987-04-14 | Skw Trostberg Aktiengesellschaft | Modifying surface tension of finely-divided materials in a liquid |
US4818288A (en) * | 1983-12-07 | 1989-04-04 | Skw Trostberg Aktiengesellschaft | Dispersant for concrete mixtures of high salt content |
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