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Chlorinated paraffin(CAS No. 63449-39-8)

Chlorinated paraffin C23H41Cl7 (cas 63449-39-8) Molecular Structure

63449-39-8 Structure

Identification and Related Records

【Name】
Chlorinated paraffin
【CAS Registry number】
63449-39-8
【Synonyms】
Cereclor 70
Chlorcosane
Paraffin waxes and Hydrocarbon waxes, chloro
A 70
ADK Cizer E 410
ADK Cizer E 450
Adekacizer E 470
Aquamix108
Arubren
Arubren CP
CP 42
Cereclor 45
Cereclor 50LV
Cereclor 51L
Cereclor 52
Cereclor 54
Cereclor65L
Cereclor 70L
Cereclor S 63
Cereclor S 70
Chlorez 700
Chlorez 700SSNP
Chlorez 760
Chlorinated paraffin waxes
Chloroflo 42
Chloroparaffin waxes
Chlorowax
Chlorowax 170
Chlorowax 40-40
Chlorowax 50
Chlorowax 500C
Chlorowax 60-50
Chlorowax 70L
Chlorowax LV
Chlorowax S 70
Cloparin S 70
Diablo 700X
Empara L 50
Hordaresin CH 171F
Hordaresin NP 70
Paroil 140
Paroil 145
Paroil170HV
Unichlor
Unichlor 50
Unichlor 70AX
【EINECS(EC#)】
264-150-0
【Molecular Formula】
C23H41Cl7 (Products with the same molecular formula)
【Molecular Weight】
348.95204
【Inchi】
InChI=1S/C10H16Cl6/c1-3-6(12)4-7(13)9(15)10(16)8(14)5(2)11/h5-10H,3-4H2,1-2H3
【InChIKey】
GJGHBJCMOWRRSZ-UHFFFAOYSA-N
【Canonical SMILES】
CCC(CC(C(C(C(C(C)Cl)Cl)Cl)Cl)Cl)Cl

Chemical and Physical Properties

【Appearance】
Clear, colorless liquid.
【Density】
1.153 g/cm3
【Boiling Point】
500.8°Cat760mmHg
【Refractive Index】
n20/D 1.525
【Flash Point】
255.9°C
【Water】
tetrahydrofuran: 0.1 g/mL, clear
【Solubilities】
tetrahydrofuran: 0.1 g/mL, clear
【Color/Form】
Generally they are viscous liquids.
Light yellow to amber, thick, oily liquid.
Colorless to pale yellow liquids
【Stability】
Stable.
【Storage temp】
Keep tightly closed in a cool place in a tightly closed container.
【Computed Properties】
Molecular Weight:348.95204 [g/mol]
Molecular Formula:C10H16Cl6
XLogP3-AA:5.8
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:7
Exact Mass:347.935367
MonoIsotopic Mass:345.938317
Topological Polar Surface Area:0
Heavy Atom Count:16
Formal Charge:0
Complexity:188
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:6
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Safety Statements 】
S23;S24/25
【HazardClass】
9
【Safety】

Suspected carcinogen. A skin and eye irritant. When heated to decomposition it emits toxic vapors of Cl?.
Safety Statements?of Paraffin waxes and hydrocarbon waxes, chlorinated (CAS NO.63449-39-8):?23-24/25?
S23: Do not breathe vapour.?
S24/25: Avoid contact with skin and eyes.
RIDADR:?UN 3082 9/PG 3
WGK Germany:?3
HazardClass:?9
PackingGroup: III

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
/Chlorinated paraffins produce/ only a weak or no irritating effect was observed, which decreased with increasing chain length.
Mild erythema
【Cleanup Methods】
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
Land spill. Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Water spill. Use natural barriers or oil spill control booms to limit spill travel. Air spill. Apply water spray or mist to knock down vapors.
【Transport】
UN 3082
【Fire Fighting Procedures】
Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources.
【Formulations/Preparations】
Chlorinated paraffins are available commercially under the following names: Cereclor (Imperial Chemical Industries); Clorafin (Hercules Powder); Chlorowax (Diamond Alkali Co).
"Chlorowax" Trademark for a series of liquid and resinous chlorinated paraffins containing from 40% to 70% Cl by wt.
/Composed of/ chlorinated paraffin waxes and hydrocarbon waxes.
【Reactivities and Incompatibilities】
... Chlorinated paraffins to release hydrochloric acid at elevated temperatures, and the hydrochloric acid inhibits the radical reaction in a flame. This property is considerably enhanced by the addition of antimony trioxide or other additives.
Prolonged exposure to light can ... cause dehydrochlorination.
Degradation by dehydrochlorination can be accelerated at elevated temperatures in the presence of aluminium, zinc, and iron oxide or chloride
【Other Preventative Measures】
Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Attempt to stop leak if without undue personnel hazard. Keep upwind. Avoid breathing vapors. Do not handle broken packages unless wearing appropriate personal protective equipment.
【Protective Equipment and Clothing】
Wear appropriate chemical protective gloves, boots and goggles.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Chlorinated paraffins are prepared by reacting pure gaseous chlorine with the starting paraffins in the absence of any solvents at temperatures between 80 deg C and 100 deg C. ... Small amounts of oxygen are frequently used to catalyze the chlorination process. Temperatures above 120 deg C must be avoided as these may cause dark or black products. Ultraviolet light is used by some manufacturers for initiating the reaction at relatively low temperatures. Once the reaction has started, the light source may be reduced in intensity or eliminated. ... The reaction is terminated by stopping the chlorine flow once the required degree of chlorination is reached. The end point is assessed by a variety of methods including refractive index and viscosity. The product is then blown with nitrogen gas to remove any unreacted chlorine and residual HCl. In most case a small amount of a storage stabilizer, usually an epoxidized vegetable oil, is then added prior to sending the finished product for storage or drumming.
Produced by passing chlorine gas into C10-C30 paraffins
U.S. Exports

CHEMICAL PROFILE: Chlorinated paraffins: Exports: 2000-2001: 11-16 million lb/yr
(1977) Data not reported separately
(1979) 3.89X10+9 g
U.S. Imports

(1977) ND
(1979) ND
U.S. Production

Paraffin waxes and hydrocarbon waxes, chloro are listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >100 million - 500 million 1990 >10 million - 50 million 1994 >10 million - 50 million 1998 >10 million - 50 million 2002 >50 million - 100 million
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Aggregated National Production Volume (pounds) 2006 10 to <50 million
CHEMICAL PROFILE: Chlorinated paraffins: US Capacity: 2001: 140 million lb.
Demand in 2000 was 97 million lb, in 2001 96 million lb, expected demand for 2005 was 97 million lb.
(1977) More than 3.26X10+10 g (C10-C30)
(1979) More than 5.13X10+10 g (C10-C30)
The total world production ... is estimated to be 500,000 tons per year
Consumption Patterns

CHEMICAL PROFILE: Chlorinate paraffins: Major uses: Metal working fluids and lubricants, 50 percent; plastics additives, 20 percent; rubber, 12 percent; coatings, 9 percent; caulks, sealants and adhesives, 6 percent; miscellaneous, 3 percent. Medium-Chain Chlorinated Paraffins represent the largest production and use category in North America (46 percent). Long-Chain Chlorinated Paraffins are second (33 percent) and, Short-Chain Chlorinated Paraffins account for the rest (21 percent).
Extreme pressure lubricant additive, 50%; plasticizer for plastics, 22%; plasticizer for paints, 9%; plasticizer for rubber, 8%; plasticizer for adhesives, 5%; plasticizer for caulks and sealants, 2%; export and others, 4% (1980)
CHEMICAL PROFILE: Chloroparaffins. Lube oil additives, 45%; plastics, including coated fabrics, 20%; rubber, 13%; paint, 9%; adhesives, 4%; caulks and sealants, 2%; miscellaneous, 7%.
CHEMICAL PROFILE: Chloroparaffins. Demand: 1986: 93 million lb; 1987: 92 million lb; 1991 /projected/: 85 million lb.
CHEMICAL PROFILE: Chlorinated paraffins: US Demand: 2000: 97 million pounds; 2001: 96 million pounds; 2005: 97 million pounds (projected).
【Usage】

As solvent for dichloramine-t, dissolving about 8%.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
Chlorinated paraffins are slowly absorbed by the dermal route in Sprague-Dawley rats. Two (14)C-labeled chlorinated paraffins, C18;50-53% Cl (CP-LH) and C28;47% Cl (CP-LL), were applied to rat skin (5-7 animals of each sex) at a concentration of 66 mg/sq cm, approximately equivalent to 2000 mg/kg body weight. Only 0.7% (males) and 0.6% (females) of the C18 dose was absorbed after 96 hr. Only 0.02% of the C28 dose was absorbed in males whereas in females the level was not detectable. This indicates that increasing chain length leads to decreased permeability. Of the absorbed C18 dose, 40% was exhaled as (14)C-labeled CO2, and 20% was excreted in urine and 20% in feces. /Long chain length chlorinated paraffins/
The absorption of two chlorinated paraffins through human skin has been studied in vitro. There was no absorption of Cereclor S52 (C14-19;52% Cl, CP-MH) following a 54-hr application to the surface of the epidermal membranes using five different receptor media. Similarly, using Cereclor 56L (C10-13; 56% Cl, CP-SH; 18.5% w/w solution in a typical cutting oil) no absorption was detected for 7 hr, but after 23 hr a slow but steady rate of absorption was detected (e.g., 0.05 +/- 0.01 ug/sq cm per hr +/- SEM; n = 6; receptor medium PEG-20 oleyl ether in saline), which was maintained for the duration of the experiment (56 hr). Owing to the anticipated low rate of absorption, the chlorinated paraffin samples were spiked with [(14)C] n-pentadecane and [(14)C] n-undecane for Cereclor S52 and 56L, respectively, in order to facilitate detection of the absorbed material. Measurement of the (14)C-alkanes was taken as a surrogate for the chlorinated paraffins, on the assumption that their rates of absorption were similar.
Female C57Bl mice were administered 12.5 MBq/kg body weight (340 uCi) (for autoradiography) or 1.25 MBq/kg body weight (34 uCi) (for determination of radioactivity) of (14)C-labeled chlorododecanes (C12) with different chlorine contents (17.5% [CP-SL], 55.9% [CP-SH] and 68.5% [CP-SH]) either by gavage or intravenous injection. Uptake of radioactivity was found by autoradiography to be highest in tissues with high cell turnover/high metabolic activity, e.g., intestinal mucosa, bone marrow, salivary glands, thymus and liver. The highest radioactivity was achieved with the chlorinated paraffin that had the lowest chlorine content. It was found that the long period of retention of heptane-soluble radioactivity, which indicated unmetabolized substance, in liver and fat after oral dosing increased with degree of chlorination. In this study it was also found that 30 to 60 days after injection of C12;17.5% Cl and C12;55.9% Cl a considerable retention of radioactivity was seen in the central nervous system. Exposure of late gestation mice showed a transplacental passage of radioactivity, and (14)C-labeling was primarily noted in the liver, brown fat and intestine of the fetuses. /short chain length chlorinated paraffin/
(14)C-Labeled [1-(14)C]polychlorohexadecane (C16;34.1% Cl, CP-ML) was given to C57Bl mice either by gavage (females) or intravenously (both sexes) at a radioactivity level of 370 kBq/animal (10 uCi) (corresponding to 0.44 umol of the chlorinated paraffin). No difference in the distribution patterns was found between the oral and intravenous administration routes. After analysis by autoradiography a high level of radioactivity was found in tissues with a high cell turnover rate and/or high metabolic activity, and lower levels could be seen in the white fat depots. High levels of radioactivity were observed in the liver, kidneys, spleen, bone marrow, brown fat, intestinal mucosa, pancreas, salivary gland and the Harderian gland 24 hr after intravenous injection. After 12 days high levels of radioactivity were seen in the adrenal cortex, abdominal fat and in the bile. Later after injection (30 days), prominent radiolabeling of the brain was found which was as high as in the liver. The chlorinated paraffin was also administered intravenously to pregnant mice, and uptake of radioactivity in the fetuses was observed. When the mice were administered on day 10 of pregnancy no tissue-specific localization was found, but after administration in late pregnancy (day 17) the distribution pattern after 6 hr was similar to that of adult mice when examined 24 hr after administration. /Intermediate chain length chlorinated paraffin/
The distribution of radioactivity in the brain and liver has been studied after gavage administration of (14)C-labeled polychloro- hexadecane (C16;69% Cl, CP-MH) (1.48 MBq/kg body weight or 40 uCi, corresponding to 1.1 mg/kg body weight) to pre-weaning NMRI mice. The chlorinated paraffin was administered by gavage at the age of 3, 10 and 20 days, and the animals were killed 24 hr and 7 days later. The radioactivity in the brain declined more rapidly in the 3-day-old mice compared to the 10- and 20-day-old mice. In the 10-day-old mice approximately 0.02% of the total administered dose was detected in the brain 24 hr after administration. Approximately 80% of the radioactivity in the brain was still present after 7 days. In the liver the radioactivity disappeared more rapidly both in younger and older animals. The radioactivity in the brain was found primarily in the white matter of the cerebellum, in the space between the neocortex and the mesencephalon and thalamus, the corpus callosum, the pons and the outer part of medulla spinalis. The radioactivity was higher in the parts of the brain which also stained for myelin, and the levels at 7 days were almost the same as those at 24 hr. After whole body autoradiography, high levels of radioactivity were found in the liver, intestinal contents, adipose tissue and adrenals. A differential labeling of the liver was observed in the 3-day-old mice, where only certain parts of the liver lobules were labeled. /Intermediate chain length chlorinated paraffin/
After oral administration of (14)C-labeled C22-26;70% Cl (CP-LH) to Fischer-344 rats at the end of a 90-day exposure period, a small part of the dose was absorbed. The highest level of radioactivity was found in the liver. Retention of radioactivity in adipose tissue, which was eliminated slowly, was also observed. In an identical study, C20-30;43% Cl (CP-LL) gave the highest levels in the liver and ovary. /long chain length chlorinated paraffin/
The exhalation of (14)CO2 was compared after single gavage or intravenous administration to female C57Bl mice of 1.25 MBq/kg body weight (34 uCi) of three chlorododecanes (C12) with different chlorine contents (17.5% [CP-SL], 55.9% [CP-SH] and 68.5% [CP-SH]. Of the administered radioactive dose 52% of C12;17.5% Cl, 32% of C12;56% Cl and 8% of C12;68% Cl were exhaled as (14)CO2 within 12 hr after dosing by either route. The major excretion route for C12;56% Cl was by urine (intravenous: 21%; oral: 29%) and for C12;68% Cl was by feces (intravenous: 8.6%; oral: 21%). The total elimination decreased as the chlorine content increased. /short chain length chlorinated paraffin/
The half-time for removal of radioactivity from abdominal fat was estimated during and after dietary administration for 8 or 10 weeks of 0.4 and 40 mg/kg feed of (36)Cl]Cereclor S52 (C14-17;52% Cl, CP-MH) in male Wistar rats. Equilibrium in liver and abdominal fat was reached at 1 and 7 weeks, respectively. The half-time for removal was about 8 weeks for abdominal fat, and it was observed that the level of radioactivity in the liver declined below the detection limit within one week. /Intermediate chain length chlorinated paraffins/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), estimated Koc values of 5900 to 2.2X10+8(SRC), determined from log Kows of 4.4 to 12.8(2) and a regression-derived equation(3), indicate that chlorinated paraffins are expected to be immobile in soil(SRC). Volatilization of chlorinated paraffins from moist soil surfaces is not expected to be an important fate process(SRC) based upon the low vapor pressure of 2X10-5 mm Hg and extremely low water solubility(4). Chlorinated paraffins are not expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure(4). Based on limited biodegradation studies chlorinated paraffins may biodegrade in soil(5-6).
AQUATIC FATE: Based on a classification scheme(1), estimated Koc values of 5900 to 2.2X10+8(SRC), determined from log Kows of 4.4 to 12.8(2) and a regression-derived equation(3), indicate that chlorinated paraffins are expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected based upon the low vapor pressure of 2X10-5 and extremely low water solubility(4). According to a classification scheme(5), the log BCF for Cereclor 52 in fish of 1.69(6) and a BCF of 7800 for fresh water fish(7), suggest the potential for bioconcentration in aquatic organisms is moderate to very high(SRC). Based on limited biodegradation studies chlorinated paraffins may biodegrade in aqueous environments(8-9). Chlorinated paraffins are not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorinated paraffins, which have a vapor pressure on the order of 2X10-5 mm Hg(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorinated paraffins are degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC). Particulate-phase chlorinated paraffins may be removed from the air by wet or dry deposition(SRC). Sunlight appears to catalyze the decomposition of chlorinated paraffins with the evolution of hydrogen chloride(3).

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