CN104908123A - Preparation method and application of sulfanilamide preservative - Google Patents
Preparation method and application of sulfanilamide preservative Download PDFInfo
- Publication number
- CN104908123A CN104908123A CN201510237235.7A CN201510237235A CN104908123A CN 104908123 A CN104908123 A CN 104908123A CN 201510237235 A CN201510237235 A CN 201510237235A CN 104908123 A CN104908123 A CN 104908123A
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- Prior art keywords
- anticorrisive agent
- preparation
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- ASPPCEPTSNCRPU-UHFFFAOYSA-N CC(C(CC=C(C1)OC)C1OC)=O Chemical compound CC(C(CC=C(C1)OC)C1OC)=O ASPPCEPTSNCRPU-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/20—Removing fungi, molds or insects
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
The invention discloses a wood preservative. The wood preservative comprises, by mass, 20-30% of copper carbonate, 30-40% of a compound I, 5-10% of allethrin and 30-40% of ammonia water. The structure of the compound I is represented by a formula shown in the specification; and a preparation method of the compound I comprises the following steps: mixing a 2,4-dihydroxyacetophenone and diazomethane ether mixed liquor with a boron trifluoride-ether complex, stirring for about 0.2-1h, carrying out a refluxing reaction for 5-7h, filtering after the reaction, washing the above obtained solid, drying, re-crystallizing to obtain an intermediate I, and reacting the intermediate I with 5-methyl-furan-2-formaldehyde to obtain an intermediate II; and reacting the intermediate II with 4-sulfamoylphenyl hydrazine to obtain an intermediate III, and reacting the intermediate III with dichloromethane and boron tribromide to obtain the target compound.
Description
Technical field
The invention belongs to Field of Fine Chemicals, be specifically related to a kind of preparation method and application of sulfamido anticorrisive agent.
Background technology
Sulfanilamide (SN) was just synthesized as the intermediate of azo dyes as far back as 1908.1932, Germany scientist K. rice very synthesized red azo compounds Prontosil; 1932 ~ nineteen thirty-five, G. Thomas gram finds that it has good therapeutic action to some bacterial infection of animal used as test.After this epochal discovery was delivered in nineteen thirty-five, cause a sensation global the world of medicine.Soon, the research of French scientist illustrates the bacteriostasis of Prontosil, is caused by the sulfanilamide (SN) that generates through metabolism in animal body due to it.In order to expand sulfanilamide (SN) antimicrobial spectrum and strengthen its antibacterial activity; the scientist of European and American countries has carried out many-sided transformation to its structure; synthesize thousands of amine compounds (according to statistics in 1945; reach kind more than 5000); therefrom filter out more than 30 kind of good effect and the lower sulfa drug of toxicity, such as: Prontosil, sulfapryidine (SP), sulphadiazine (SD), thalazole (PST), sulphathiazole (ST), sulphoamidine (SG), sulfanilamide (SN) are different? azoles (SIZ), sulfadimidine (SM2).The derivative of P-aminobenzene-sulfonamide (abbreviation sulfanilamide (SN)) is the chemical synthetic drug that a class has bacteriostatic activity, and sulfa drug mainly suppresses it to breed to bacterium.
Anticorrisive agent refers to chemical composition that is natural or synthesis, for adding food, medicine, pigment, biological sample etc., to postpone the corruption that growth of microorganism or chemical change cause.Nitrite and sulfur dioxide are one of conventional anticorrisive agents.Anticorrisive agent Main Function suppresses microbial growth and breeding, to extend the holding time of food, and the medicament of inhibiting substances corruption.Timber preservative (Wood Preservative) is a kind of chemical agent, adopting after by some means or other by its injection timber, can strengthen the effect of timber opposing mycocriny, insect pest, marine borer erosion etc.Up to the present, the most conventionally prevent the method for foxiness from still using chemical agent anticorrosion.What current use was maximum is waterborne-type preservation, accounts for 3/4 of anticorrisive agent use total amount.
One of important channel preservative treatment is carried out to timber, extends the service life of woodwork, be saving timber, protecting forest resources.The timber that nowadays China use after preservative treatment is little, and mostly uses the mankind and the large traditional timber preservative of environmental hazard.Therefore Study and Development novel wood preservative is very necessary.
Summary of the invention
Goal of the invention: the preparation method that the invention provides a kind of anticorrisive agent.
Technical scheme: the preparation method that the invention provides a kind of anticorrisive agent, concrete steps are as follows:
Under ice-water bath stirring action, 2,4-dihydroxyacetophenone is mixed with diazomethane ether mixed liquor, boron trifluoride-ether complex, after stirring about 0.2 ~ 1h, back flow reaction 5 ~ 7h again, after reaction terminates, filters, by gained solids wash, drying, recrystallization, obtains intermediate compound I
by intermediate compound I and 5-methyl-ribofuranosyl-2-formaldehyde
reaction, obtains intermediate II
by intermediate II and to Hydrazinobenzenesulfonamide
reaction, obtains intermediate III
intermediate III and carrene, Boron tribromide react, and obtain target compound;
Above-mentioned target compound is mixed with copper nitrate, allethrin and ammoniacal liquor, obtains anticorrisive agent.
The mass ratio of each component of anticorrisive agent be: 20 ~ 30% copper nitrates, 30 ~ 40% target compounds, 5 ~ 10% allethrins, 30 ~ 40% ammoniacal liquor.
In above-mentioned preparation process, described washing methods is successively with watery hydrochloric acid, distilled water, cold ethanol, distilled water washing.
Described drying means is that infrared lamp irradiates lower drying, and temperature is 80 ~ 100 DEG C, and the time is 2 ~ 10 hours.
Described recrystallization method is be solvent with absolute ethyl alcohol, is recrystallized.
Beneficial effect: preservative substance formula provided by the invention is simple, effectively can place decay of wood.
Detailed description of the invention:
Embodiment 1
Step 1, puts into there-necked flask by 2,4-dihydroxyacetophenone, then adds diazomethane ether mixed liquor, boron trifluoride-ether complex, after reaction about 0.2h, then back flow reaction 5h.After reaction terminates, filter, obtaining solid uses watery hydrochloric acid (3 × 100mL), distilled water (3 × 150mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, is dissolved in absolute ethyl alcohol recrystallization and obtains lenticular intermediate I by the solid crude product obtained.
Under stirring at room temperature, intermediate, the KOH aqueous solution, 5-methyl-ribofuranosyl-2-formaldehyde, ethanol is added successively in round-bottomed flask, after continuing stirring reaction 4h, watery hydrochloric acid acidifying, regulate pH to be 4, filter, the solid obtained uses distilled water (3 × 100mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, obtains lenticular intermediate II.
At-20 DEG C, stir, in there-necked flask, add intermediate II, carrene successively on one side, and progressively drip Boron tribromide, after stirring about 1h, room temperature continues reaction about 12h, after reaction terminates, filter, solid distilled water washs, last vacuum drying, and the solid obtained is dissolved in absolute ethyl alcohol, recrystallization is purified, and obtains lenticular target compound.
Step 2, mass percent, by 20g copper nitrate, 30g above-claimed cpd, 5g allethrin is dissolved in 30g ammoniacal liquor, obtain preservative.
Embodiment 2
Step 1, puts into there-necked flask by 2,4-dihydroxyacetophenone, then adds diazomethane ether mixed liquor, boron trifluoride-ether complex, after reaction about 0.2h, then back flow reaction 5h.After reaction terminates, filter, obtaining solid uses watery hydrochloric acid (3 × 100mL), distilled water (3 × 150mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, is dissolved in absolute ethyl alcohol recrystallization and obtains lenticular intermediate I by the solid crude product obtained.
Under stirring at room temperature, intermediate, the KOH aqueous solution, 5-methyl-ribofuranosyl-2-formaldehyde, ethanol is added successively in round-bottomed flask, after continuing stirring reaction 4h, watery hydrochloric acid acidifying, regulate pH to be 4, filter, the solid obtained uses distilled water (3 × 100mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, obtains lenticular intermediate II.
At-20 DEG C, stir, in there-necked flask, add intermediate II, carrene successively on one side, and progressively drip Boron tribromide, after stirring about 1h, room temperature continues reaction about 12h, after reaction terminates, filter, solid distilled water washs, last vacuum drying, and the solid obtained is dissolved in absolute ethyl alcohol, recrystallization is purified, and obtains lenticular target compound.
Step 2, by 20g copper nitrate, 40g above-claimed cpd, 5g allethrin is dissolved in 30g ammoniacal liquor, obtain preservative.
Embodiment 3
Step 1, puts into there-necked flask by 2,4-dihydroxyacetophenone, then adds diazomethane ether mixed liquor, boron trifluoride-ether complex, after reaction about 0.2h, then back flow reaction 5h.After reaction terminates, filter, obtaining solid uses watery hydrochloric acid (3 × 100mL), distilled water (3 × 150mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, is dissolved in absolute ethyl alcohol recrystallization and obtains lenticular intermediate I by the solid crude product obtained.
Under stirring at room temperature, intermediate, the KOH aqueous solution, 5-methyl-ribofuranosyl-2-formaldehyde, ethanol is added successively in round-bottomed flask, after continuing stirring reaction 4h, watery hydrochloric acid acidifying, regulate pH to be 4, filter, the solid obtained uses distilled water (3 × 100mL), cold ethanol (3 × 50mL), distilled water (3 × 100mL) to wash successively, drying, obtains lenticular intermediate II.
At-20 DEG C, stir, in there-necked flask, add intermediate II, carrene successively on one side, and progressively drip Boron tribromide, after stirring about 1h, room temperature continues reaction about 12h, after reaction terminates, filter, solid distilled water washs, last vacuum drying, and the solid obtained is dissolved in absolute ethyl alcohol, recrystallization is purified, and obtains lenticular target compound.
Step 2, by 30g copper nitrate, 30g above-claimed cpd, 10g allethrin is dissolved in 40g ammoniacal liquor, obtain preservative.
During use, timber is all infiltrated with anticorrisive agent in 2 ~ 3 hours, taking-up is dried.
Claims (7)
1. a preparation method for anticorrisive agent, is characterized in that carrying out according to the following steps:
Under ice-water bath stirring action, 2,4-dihydroxyacetophenone is mixed with diazomethane ether mixed liquor, boron trifluoride-ether complex, after stirring about 0.2 ~ 1h, back flow reaction 5 ~ 7h again, after reaction terminates, filters, by gained solids wash, drying, recrystallization, obtains intermediate compound I
by intermediate compound I and 5-methyl-ribofuranosyl-2-formaldehyde
reaction, obtains intermediate II
by intermediate II and to Hydrazinobenzenesulfonamide
reaction, obtains intermediate III
intermediate III and carrene, Boron tribromide react, and obtain target compound;
Above-mentioned target compound is mixed with copper nitrate, allethrin and ammoniacal liquor, obtains anticorrisive agent.
2. the preparation method of anticorrisive agent as claimed in claim 1, is characterized in that the mass ratio of its each component is: 20 ~ 30% copper nitrates, 30 ~ 40% target compounds, 5 ~ 10% allethrins, 30 ~ 40% ammoniacal liquor.
3. the preparation method of anticorrisive agent as claimed in claim 3, is characterized in that described washing methods is for washing with watery hydrochloric acid, distilled water, cold ethanol, distilled water successively.
4. the preparation method of anticorrisive agent as claimed in claim 3, it is characterized in that described drying means is that infrared lamp irradiates lower drying, temperature is 80 ~ 100 DEG C, and the time is 2 ~ 10 hours.
5. the preparation method of anticorrisive agent as claimed in claim 3, is characterized in that described recrystallization method is for being solvent with absolute ethyl alcohol, is recrystallized.
6. utilize the anticorrisive agent that the preparation method of the anticorrisive agent described in claim 1 obtains.
7. the application of anticorrisive agent as claimed in claim 6, is characterized in that being applied to wood preservation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510237235.7A CN104908123B (en) | 2015-05-12 | 2015-05-12 | The preparation method and application of sulfonamides preservative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510237235.7A CN104908123B (en) | 2015-05-12 | 2015-05-12 | The preparation method and application of sulfonamides preservative |
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| Publication Number | Publication Date |
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| CN104908123A true CN104908123A (en) | 2015-09-16 |
| CN104908123B CN104908123B (en) | 2016-12-07 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1413467A (en) * | 2001-10-26 | 2003-04-30 | 周平安 | Wood antiseptic |
| CN1701936A (en) * | 2004-05-24 | 2005-11-30 | 虞选勇 | Wood anti-corrosion infusion |
| CN1835830A (en) * | 2003-06-17 | 2006-09-20 | 法布罗技术有限公司 | Particulate wood preservative and method for producing same |
| CN101450496A (en) * | 2007-11-29 | 2009-06-10 | 虞选勇 | Wood preservative |
| US8722198B2 (en) * | 2004-05-17 | 2014-05-13 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
-
2015
- 2015-05-12 CN CN201510237235.7A patent/CN104908123B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1413467A (en) * | 2001-10-26 | 2003-04-30 | 周平安 | Wood antiseptic |
| CN1835830A (en) * | 2003-06-17 | 2006-09-20 | 法布罗技术有限公司 | Particulate wood preservative and method for producing same |
| US8722198B2 (en) * | 2004-05-17 | 2014-05-13 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
| CN1701936A (en) * | 2004-05-24 | 2005-11-30 | 虞选勇 | Wood anti-corrosion infusion |
| CN101450496A (en) * | 2007-11-29 | 2009-06-10 | 虞选勇 | Wood preservative |
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| Publication number | Publication date |
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| CN104908123B (en) | 2016-12-07 |
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Address after: 215138 No. 1 Zhangtangbangxiang, Yangchenghu Town, Xiangcheng District, Suzhou City, Jiangsu Province Patentee after: Suzhou Xiangyuan New Materials Co., Ltd. Address before: Suzhou City, Xiangcheng District province 215138 Jiangsu Yangchenghu town (Hunan City) ten Village Patentee before: Suzhou Xiangyuan Speical Fine Chemical Co., Ltd. |
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