Lignosulfonic acid
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Lignosulfonic acid
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CAS No:
8062-15-5
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Chemical Name:
Lignosulfonic acid
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Synonyms:
Lignosulfonic acid;Lignin,sulfite;Protektol W;Ligninsulfonic acid;Poly(lignosulfonic acid);Sulfite lignin;Lignosulfonate;Ligninsulfonate;Lignosulfate;LST 7;Sulfonyllignin;Sulfonic acids,ligno;Ameribond 2X;Indulin SN;Wafex SR;Sulfolignin;Borresperse 3A;HR 7;HR 6L;Ultrazine;Stepsperse DF 500;Stepsperse DF 200;Stepsperse DF 400;Lignotech DP 524;Tembec ARBO-A 02;Stepsperse DF 100;Lignosulfonic acids;Wafolin;DP 651;Vanillex HWR;Sulfonated lignin;EAX 907;EAX 910;EAX 402;58318-45-9;92680-76-7;1222186-64-2
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CAS No:
Characteristics
173
1.9
284 °C
Lignosulfonates show good water solubility in water over the entire pH range but are insoluble in many organic solvents. /Ligninsulfonate salts/
... ligninsulfonates must be easily soluble and the dispersions stable at higher temperature. These properties are achieved by suitable purification and chemical treatment of the crude product. /Ligninsulfonate salts/
Safety Information
SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Toxicity
IDENTIFICATION AND USE: Lignosulfuric acid is a by-product of the pulp and paper industry. Worldwide, the single largest use of lignosulfonates is as water reducers for concrete. Additional large-volume uses of lignosulfonates include animal feed pellet binders, dispersants for gypsum board manufacture, thinners/fluid loss control agents for drilling muds, dispersants/grinding aids for cement manufacture, binders for granulated fertilizers and in dust control applications, particularly road dust abatement, and other specialty dust control applications. Lignosulfuric acid was extensively studied for its anti-HIV and anti-HSV activity in various cellular assays and demonstrated broad anti-HIV and anti-HSV activity. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Lignosulfuric acid inhibited loose sperm attachment and the development of tight binding on the zona pellucida. It was causing inhibition of fertilization and embryo development in a number of nonmammalian species. Due to the antifertility properties of this nontoxic molecule, lingosulfuric acid appears to have potential as a vaginal contraceptive.
/AQUATIC SPECIES/ Young S. gairdneri were exposed to lignosulfonates (LS (environmental pollutants)) at concentrations of 0, 40, 80, 160, 320, 640, 1280 and 1920 ppm for 35 or 60 days. At concentrations of 160 ppm LS and higher the growth rates were slower. The higher concentrations had the most retarding effect on growth, but a clear general relationship between LS concentration and growth retardation was not observed. The bacterial flora in the digestive tract of the fish was examined. The predominant micro-organisms were flavobacteria, bacilli, streptococci and yeasts (Cryptococcus spp.), which were also isolated from the diet. There were about 10,000 viable aerobic and 1000 anaerobic bacteria/g of intestinal contents. There was no significant difference in quantitative or qualitative composition of the intestinal flora of the different groups. The following groups of digestive enzymes were studied: proteinases, amylases, lipases and DNases. The activities of proteinases and nucleases were significantly impaired in fish exposed to concentrations of 1280 ppm LS and higher, and those of amylases at concentrations of 320 ppm LS and higher. A possible connection between the reduced growth rates and depressed activities of the digestive enzymes is discussed, but no firm conclusion regarding the mechanism by which LS effects fish growth can be made.
Ligninsulfonic acids are made from native lignon ... lignin made from sulfate pulping and ... lignin made from alkaline (kraft) pulping of wood|... Under optimal conditions, 1 kg wheat straw could produce 0.225 kg xylose with 95% purity, 4.16 kg hydrolyzate of sulfomethylation treatment containing 5.5% lignosulfonate, 0.183 kg ethanol and 0.05 kg lignin residue. Compared to present technology, this process is a potential economically profitable wheat straw biorefinery.
Use of lignosulfonates for various industrial applications is dependent on purity, degree of sulfonation, number of hydroxyl groups and molecular mass distribution of the sulfonates.|Most applications of lignin and lignosulfonates are based on their dispersing, binding, complexing, and emulsion-stabilizing properties. About 50% of all lignosulfonates produced worldwide are used for concrete mixtures, usually in the form of calcium or sodium salts. Addition of 0.1-0.3% lignosulfonates to cement retards the setting or hydration of concrete. The second most important application is as a binder for animal feed pellets, where mainly calcium and ammonium salts are applied in order to improve pellet durability and abrasive resistance. A maximum dosage of 4% is possible in finished pellets. Primarily chrome and ferrochrome salts of lignosulfonates function in oil well drilling muds as mud thinners, clay conditioners, viscosity-control agents, and fluid-loss additives. Mud systems conditioned with 0.2-0.5% lignosulfonates, applied in the crude oil industry, perform well at high pressures and at temperatures of up to 175 °C. Another major market, especially for crude lignosulfonate spent liquors, is the dust control application for stabilizing insurfaced roads. In addition to these bulk applications a variety of specialty markets exist. Lignosulfonates are used for the granulation, complexation, or encapsulation of pesticides and as additives for gypsum boards in order to disperse the stucco. Lignosulfonates are used as dispersant in water-based paints and inks. Lignosulfonates and spent sulfite liquors are used for water treatment plants and paper machines to reduce deposits and slime formation or to complex metals such as zinc in cooling-water cycles. They are used in industrial cleaner formulations, for the complexation of nutrients in soil stabilization, for dyes or as additives in the brick industry. Modified lignosulfonates are additives in lead - acid batteries, which extend the service life of the product significantly. As further future uses the stabilization of enzyme formulations, biocide neutralization, and applications exploiting the antiviral and the chelating properties have been targeted. /Lignosufonates/|Soil microcosms were constructed and monitored to evaluate the impact of substrate addition and transient aerobic and anaerobic conditions on TNT, RDX and HMX biodegradation in grenade range soils. ... glycerin and lignosulfonate can be potentially used to stimulate RDX and HMX biodegradation by increasing oxygen consumption rates in soil.|Recently, there has been a growing research interest on renewable composite due to sustainability concerns. This work demonstrated the possibility of using eucalyptus lignosulfonate calcium (HLS) particles as reinforcement in polyvinyl alcohol (PVA) matrix. ...|For more Artificial Pollution Sources (Complete) data for Lignosulfuric acid (6 total), please visit the HSDB record page.
According to the 2016 TSCA Inventory Update Reporting data, 1 reporting facility estimated the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of lignosulfuric acid in the United States is fewer than 10 workers; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).
Drug Information
/EXPL THER/ OBJECTIVES: Lignosulfonic acid (LA), a low-cost lignin-derived polyanionic macromolecule, was extensively studied for its anti-HIV and anti-HSV activity in various cellular assays, its mechanism of viral inhibition and safety profile as potential microbicide. RESULTS: LA demonstrated potent inhibitory activity of HIV replication against a wide range of R5 and X4 HIV strains and prevented the uptake of HIV by bystander CD4+ T cells from persistently infected T cells in vitro (IC50: 0.07 - 0.34 uM). LA also inhibited HSV-2 replication in vitro in different cell types (IC50: 0.42 - 1.1 uM) and in rodents in vivo. Furthermore, LA neutralized the HIV-1 and HSV-2 DC-SIGN-mediated viral transfer to CD4+ T cells (IC50: ~1 uM). In addition, dual HIV-1/HSV-2 infection in T cells was potently blocked by LA (IC50: 0.71 uM). No antiviral activity was observed against the non-enveloped viruses Coxsackie type B4 and Reovirus type 1. LA is defined as a HIV entry inhibitor since it interfered with gp120 binding to the cell surface of T cells. Pretreatment of PBMCs with LA neither increased expression levels of cellular activation markers (CD69, CD25 and HLA-DR), nor enhanced HIV-1 replication. Furthermore, we found that LA had non-antagonistic effects with acyclovir, PRO2000 or LabyA1 (combination index (CI): 0.46 - 1.03) in its anti-HSV-2 activity and synergized with tenofovir (CI: 0.59) in its anti-HIV-1 activity. To identify mechanisms of LA resistance, we generated in vitro a mutant HIV-1 NL4.3LAresistant virus, which acquired seven mutations in the HIV-1 envelope glycoproteins: S160N, V170N, Q280H and R389T in gp120 and K77Q, N113D and H132Y in gp41. Additionally, HIV-1 NL4.3LAresistant virus showed cross-resistance with feglymycin, enfuvirtide, PRO2000 and mAb b12, four well-described HIV binding/fusion inhibitors. Importantly, LA did not affect the growth of vaginal Lactobacilli strains. CONCLUSION: Overall, these data highlight LA as a potential and unique low-cost microbicide displaying broad anti-HIV and anti-HSV activity.|/EXPL THER/ Some secondary metabolites from plants show to have potent inhibitory activities against microbial pathogens, such as human immunodeficiency virus (HIV), herpes simplex virus (HSV), Treponema pallidum, Neisseria gonorrhoeae, etc. Here we report that lignosulfonic acid (LSA), a polymeric lignin derivative, exhibits potent and broad activity against HIV-1 isolates of diverse subtypes including two North America strains and a number of Chinese clinical isolates values ranging from 21.4 to 633 nM. Distinct from other polyanions, LSA functions as an entry inhibitor with multiple targets on viral gp120 as well as on host receptor CD4 and co-receptors CCR5/CXCR4. LSA blocks viral entry as determined by time-of-drug addiction and cell-cell fusion assays. Moreover, LSA inhibits CD4-gp120 interaction by blocking the binding of antibodies specific for CD4-binding sites (CD4bs) and for the V3 loop of gp120. Similarly, LSA interacts with CCR5 and CXCR4 via its inhibition of specific anti-CCR5 and anti-CXCR4 antibodies, respectively. Interestingly, the combination of LSA with AZT and Nevirapine exhibits synergism in viral inhibition. For the purpose of microbicide development, LSA displays low in vitro cytotoxicity to human genital tract epithelial cells, does not stimulate NF-kappaB activation and has no significant up-regulation of IL-1alpha/beta and IL-8 as compared with N-9. Lastly, LSA shows no adverse effect on the epithelial integrity and the junctional protein expression. Taken together, our findings suggest that LSA can be a potential candidate for tropical microbicide.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
AHR 2438B
Lignosulfonic acid Use and Manufacturing
Ligninsulfonic acids are made from native lignin. Two different starting materials are available: (1) lignin made from sulfite pulping and (2) lignin made from alkaline (kraft) pulping of wood. In the first case, the sulfite waste liquor is purified and marketed as a liquid or a solid. Lignin from kraft pulping is first purified and then sulfonated.|Various methods have been developed for isolating and purifying lignosulfonates from spent pulping liquors. One of the earliest and most widely used industrial processes is the Howard process, where calcium lignosulfonates are precipitated from spent pulping liquor by addition of excess lime. Lignin recoveries of 90-95% are obtainable through this process. Other methods used industrially include ultrafiltration and ion-exclusion, which uses ion-exchange resins to separate lignin from sugars. Laboratory methods for isolating lignosulfonates include dialysis, electrodialysis, ion exclusion, precipitation in alcohol, and extraction with amines. They can also be isolated by precipitation with long-chain-substituted quaternary ammonium salts. /Lignosulfonates/
Adhesives and sealant chemicals
Adhesives and sealants
Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Lignosulfonic acid:
Adhesive manufacturing|Lignosulfonic acid: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|Industrial lignins are by-products of the pulp and paper industry. Lignosulfonate [8062-15-5], derived from sulfite pulping of wood, and kraft lignin [8068-05-1], derived from kraft pulping, are the principal commercially available lignin types.|Industrial ligninsulfonates are globular colloids with molecular masses between 2000 and 100,000 whose structures have not yet been fully elucidated. Their basic structural unit is phenylpropane. The structural formula shows five structural units linked with the parent unit in various ways. The degree of sulfonation varies between 0.3 and 1.0 sulfite groups per phenylpropane unit.|The suitability of ligninsulfonates for various industrial purposes depends on the purity, degree of sulfonation, number of hydroxyl groups, and molecular mass distribution of the sulfonates. In addition to highly dispersive action during milling and ease of redispersion, ligninsulfonates must be easily soluble and the dispersions stable at higher temperature. These properties are achieved by suitable purification and chemical treatment of the crude product.
Computed Properties
Molecular Weight:490.5
XLogP3:1.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:12
Exact Mass:490.09673937
Monoisotopic Mass:490.09673937
Topological Polar Surface Area:173
Heavy Atom Count:32
Complexity:758
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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