FORM 2
THE PATENTS ACT, 1970
(39 of 1970)
&
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
(See section 10, rule 13)
1. Title of the invention: C5 SUGAR BASED GELATORS FOR OIL SPILLS
2. Applicant(s)
NAME NATIONALITY ADDRESS
HINDUSTAN PETROLEUM
CORPORATION LIMITED
Indian Hindustan Petroleum Corporation
Ltd, Petroleum House, 17 Jamshedji
Tata Road, Churchgate, Mumbai
400020, India
3. Preamble to the description
COMPLETE SPECIFICATION
The following specification particularly describes the invention and the manner in which it
is to be performed.
1
2
TECHNICAL FIELD
[0001] The subject matter described herein in general relates to sugar-based compounds that are
able to form gels. The subject matter further relates to methods of making the sugar-based
compounds, and gels including such compounds. The sugar-based compounds can be used to
control hydrocarbon spill by gel formation. The subject matter further 5 relates to methods for
recovery of hydrocarbons and the sugar based compounds from the gel.
BACKGROUND
[0002] A gel can be defined as a solution in which the solid, also known as a gelator, is meshed
to form a rigid or semi-rigid mixture. Depending on the structural nature of gel networks, gels
10 can be simply divided into chemical gels and physical gels. In the case of chemical gels, the
aggregation units at different levels are connected into three-dimensional networks via covalent
bonds whereas in physical gels, the molecules of a gelator aggregate into network structure via
various non-covalent interactions, which are considerably weaker than covalent bonds.
[0003] Physical gelation of water and solvents include polymers, micro- or nano-particles, and
15 low-molecular mass organic compounds (LMMGs). The gels formed by latter are named
supramolecular gels or molecular gels and can be used for gelation of oil from oil–water
mixtures for oil spill recovery. The spilled oil is transformed from a liquid into semi-solid or
rubber-like materials floating on the surface of water by introducing LMMGs into the oil
contaminated water.
20 [0004] Kar and co-workers have disclosed supramolecular hydrogelation of a composite
including single walled nanotubes (SWNTs) and amphiphilic dipeptide carboxylates (Chem.
Commun., 2012, 48, 8389–8391).
[0005] Kar and co-workers have disclosed dipeptide-based long-chain acids/salts capable of
efficiently gelating organic solvents and water. The xerogels prepared from the organogels
25 showed time-dependent adsorption of dyes such as crystal violet (Langmuir 2009, 25(15), 8639–
8648).
SUMMARY
[0006] The present disclosure relates to a compound having the Formula:
3
Formula I
Where in, R1 and R2 are independently selected from hydrogen or C1 to C6 alkyl. The present
disclosure also relates to a method of preparing the compound of Formula I.
[0007] The present disclosure further relates to a gel comprising 5 a compound of Formula I and a
solvent. The present disclosure further relates to a method of a gel comprising contacting the
compound of Formula I with solvent.
[0008] The present disclosure further relates to a method of containing the spill of a
hydrocarbon, the method comprising contacting the hydrocarbon with the compound of Formula
10 I to obtain a gel. The present disclosure further relates to a method of reclaiming solvent from the
gel comprising a compound of Formula I and a solvent.
[0009] These and other features, aspects and advantages of the present subject matter will be
better understood with reference to the following description and appended claims. This
summary is provided to introduce a selection of concepts in a simplified form. This summary is
15 not intended to identify key features or essential features of the claimed subject matter, nor is it
intended to be used to limit the scope of the claimed subject matter.
DETAILED DESCRIPTION
[0010] Those skilled in the art will be aware that the present disclosure is subject to variations
20 and modifications other than those specifically described. It is to be understood that the present
disclosure includes all such variations and modifications. The disclosure also includes all such
steps, features, compositions and compounds referred to or indicated in this specification,
individually or collectively and any and all combinations of any or more of such steps or
features.
25 Definitions
4
[0011] For convenience, before further description of the present disclosure, certain terms
employed in the specification, and examples are collected here. These definitions should be read
in the light of the remainder of the disclosure and understood as by a person of skill in the art.
The terms used herein have the meanings recognized and known to those of skill in the art,
however, for convenience and completeness, particular terms 5 and their meanings are set forth
below.
[0012] The articles “a”, “an” and “the” are used to refer to one or to more than one (i.e., to at
least one) of the grammatical object of the article.
[0013] The terms “comprise” and “comprising” are used in the inclusive, open sense, meaning
10 that additional elements may be included. Throughout this specification, unless the context
requires otherwise the word “comprise”, and variations, such as “comprises” and “comprising”,
will be understood to imply the inclusion of a stated element or step or group of element or steps
but not the exclusion of any other element or step or group of element or steps.
[0014] The term “including” is used to mean “including but not limited to”. “Including” and
15 “including but not limited to” are used interchangeably.
[0015] The term "hydrocarbon(s)" refers to organic compounds that are made of hydrogen and
carbon atoms. The source of the hydrocarbons may be from crude oils and refined petroleum
products. Crude oil and other petroleum fractions may include compoundswith hetero atoms like
nitrogen, oxygen, sulfur, halogens and metallic elements along with hydrocarbons.
20 [0016] The term "gel" refers to a colloidal suspension of a solid dispersed in liquid and appears
like semi solid.
[0017] The term “CRN” means cracked run naptha (mainly comes from the Fluidized Catalytic
Cracking (FCC) unit in the refinery).
[0018] The term “SRN” means straight run naphtha, which comes from direct distillation of
25 crude oil.
[0019] The term “diesel”means a specific fractional distillate of petroleum crude oil between
200°C and 350°C at atmospheric pressure.
[0020] Ratios, concentrations, amounts, and other numerical data may be presented herein in a
range format. It is to be understood that such range format is used merely for convenience and
30 brevity and should be interpreted flexibly to include not only the numerical values explicitly
recited as the limits of the range, but also to include all the individual numerical values or sub5
ranges encompassed within that range as if each numerical value and sub-range is explicitly
recited. For example, a temperature range of about 140°C to about 180°C should be interpreted
to include not only the explicitly recited limits of about 140°C to about 180°C, but also to
include sub-ranges, such as 145°C to 155°C, 150°C to 170°C, and so forth, as well as individual
amounts, including fractional amounts, within the specified ranges, such 5 as 142.2°C, 140.6°C,
and 141.3°C, for example.
[0021] The present disclosure relates to a class of amphiphilic gelators which can be used for
selective extraction of oil in water systems and water in oil systems. The oil can include, but not
limited to, straight run naphtha, gasoline, diesel fractions and crude oil individually and as a
10 mixture of oil and water emulsion. The gelators on contact with the oil absorb the oil and swell
to form a gel. This causes phase separation of the oil from the water. Theoil absorbed onto the
gelators can be easily recovered from the gel by heating the gel. Although the description
herewith provided is with reference to the use of gelators in oil spill recovery, it may be
understood by a person skilled in the art, that the gelators find use in other areas, such as
15 cosmetics, tissue engineering, drug delivery, separation of biomolecules, and stimulusresponsive
advanced materials, as well, albeit with a few variations, as may be understood by a
person skilled in the art.
[0022] In one implementation, the present disclosure relates to a compound having the Formula:
20
Formula I
wherein, R1 and R2 are independently selected from hydrogen or C1 to C6 alkyl.
[0023] The present disclosure also relates to a method of preparing the compound of Formula I.
[0024] The molecular gelators of Formula I can be used for the containment of spilled refinery
25 products such as straight run naphtha, gasoline, diesel fractions and crude oil individually and as
a mixture of oil and water emulsion.
6
[0025] The compounds of Formula I can be used for remediation of a release of spilled crude oil
or hydrocarbon.
[0026] In one implementation, the present disclosure relates to a compound having the Formula:
5
Formula I
wherein, R1 is hydrogen and R2 is C1 to C6 alkyl.
[0027] In another implementation, the present disclosure relates to a compound having the
Formula:
10
Formula I
wherein, R1 is C1 to C6 alkyl and R2 is hydrogen.
[0028] In yet another implementation, the present disclosure relates to a compound having the
Formula:
15
Formula I
7
wherein, R1 and R2 are C1 to C6 alkyl.
[0029] In one implementation, the present disclosure relates to a compound having the Formula:
Formula I
wherein, 5 R1 and R2 are hydrogen.
[0030] In one implementation, the present disclosure relates to a compound having the Formula:
Formula I
wherein, R1 and R2 are is C1 alkyl.
10 [0031] In another implementation, the present disclosure relates to a compound having the
Formula:
Formula I
wherein, R1 and R2 are is C2 alkyl.
15 [0032] In yet another implementation, the present disclosure relates to a compound having the
Formula:
8
Formula I
wherein, R1 and R2 are C2 to C4 alkyl.
[0033] In one implementation, the present disclosure relates to a compound having the Formula:
5
Formula I
wherein, R1 and R2 are C4 to C6 alkyl..
[0034] In one implementation, the present disclosure relates to a compound having the Formula:
10 Formula I
wherein, R1 and R2 are C4 alkyl.
[0035] In another implementation, the present disclosure relates to a compound having the
Formula:
9
Formula I
wherein, R1ishydrogenand R2 is C2 alkyl.
[0036] In one implementation, the present disclosure relates to a compound having the Formula
shown below with the substituents as provided 5 in the below Table:
Compound IUPAC names R1 R2
1 (2,2'-diphenyl-4,4'-bi(1,3-dioxolan)-5-
yl)methanol)
H H
2 (2,2'-dimethyl-2,2'-diphenyl-4,4'-
bi(1,3-dioxolan)-5-yl)methanol)
-CH3 -CH3
3 (2,2'-diethyl-2,2'-diphenyl-4,4'-bi(1,3-
dioxolan)-5-yl)methanol)
-CH2CH3 -CH2CH3
[0037] In one implementation, the present disclosure provides a process for the preparation of
compound Formula I, the process comprising the steps of: mixing a non polar solvent and a polar
10 solvent to obtain first solution, contacting xylitol and a reagent to obtain a second solution,
adding second solution to the first solution to obtain a solution and reacting the solution with a
second reactant to obtain the desired product.
[0038] In another implementation, the non polar solvent is selected from the group consisting of
cyclohexane, hexane and heptane.
10
[0039] In one implementation, the polar solvent is selected from the group consisting of
methanol and ethanol.
[0040] In another implementation, the present disclosure provides a process for the preparation
of compound Formula I, wherein the step of adding second solution to the first solution to obtain
a solution is done at a temperature range of 60-1000C for 5-20 mins, 5 preferably at a temperature
of 70-900C for 5-15 mins and most preferably at a temperature of 800C for 10 mins.
[0041] In another implementation, the reagent is selected from the group consisting of p-TsOH
and dodecyl benzene sulfonic acid.
[0042] In another implementation, the second reactant is selected from the group consisting of
10 benzaldehyde, acetophenone, and phenyl ethyl ketone.
[0043] The process for the preparation of compound Formula I further comprises the purification
step.
[0044] The compounds of Formula I can be used to form gels. In one implementation, the
compounds of Formula I can be added to one or more solvents in order to produce a gel. In
15 another implementation, the compounds of Formula I can be added to a solvent in order to
produce a gel.
[0045] The present disclosure also relates to a method for producing a gel comprising contacting
the compound of Formula I with a solvent. The term solvent refers to a polar solvent, non-polar
solvent and mixtures thereof.
20 [0046] In another implementation, the solvent comprises water, an organic solvent, or mixtures
thereof. Solvents can be nonpolar such as, for example, hydrocarbons like pentane, cyclopentane,
hexane, cyclohexane, benzene, toluene, xylene, 1,4-dioxane, chloroform, diethyl ether or
mixtures thereof.
[0047] In one implementation, the solvents can be polar, aprotic solvents such as,
25 dichloromethane, tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, acetonitrile,
pyridine, carbon disulfide, benzonitrile, or dimethyl sulfoxide.
[0048] In another implementation, the solvent can be polar protic solvents such as alcohols and
carboxylic acids including, but not limited to, formic acid, n-butanol, isopropanol, n-propanol,
ethanol, methanol, acetic acid, ethylene glycol, propylene glycol, glycerin, or water. Mixtures of
30 solvents can also be used herein.
11
[0049] In one implementation, the solvent can be a mixture of water with a hydrocarbon. In
another implementation, the solvent is a hydrocarbon. In another implementation, the solvent is
selected from crude oil, or a petroleum product.
[0050] The gelators of the present disclosure are effective in forming gels in water in oil systems,
and oil in water systems. On this account, the gelator is highly versatile, 5 inexpensive, easy to
prepare, biodegradable, and non-toxic, unlike the conventionally used gelators.
[0051] The present disclosure also relates to method of recoveringthe spill of a hydrocarbon in a
water body. The water body may includes, oceans, seas, rives, etc. In an embodiment, the spill of
the hydrocarbon in the water body is recovered by contacting the hydrocarbon with the
10 compound of Formula I to obtain a gel. The formation of gel separates the oil from the water
body; the gel is further separated and recovered from the water body to recover the hydrocarbon
spill.
[0052] In one implementation, a method of recovering crude oil, or petroleum product from a
spill of crude oil, or the petroleum product comprises: (a) forming a gel comprising the crude oil,
15 or the petroleum product and a compound of formula I; (b)collecting the gel; and (c) reclaiming
the crude oil or the petroleum product from the gel.
[0053] In another implementation, method of reclaiming solvent and a compound of Formula I
from the gel comprising heating the gel to a suitable temperature for a suitable time to separate
the solvent and the compound of Formula I.
20 Examples
[0054] The disclosure will now be illustrated with working examples, which is intended to
illustrate the working of disclosure and not intended to take restrictively to imply any limitations
on the scope of the present disclosure. Other examples are also possible which are within the
scope of the present disclosure.
25 Example 1
Synthesis of compound of Formula I
[0055] The compound of Formula I was synthesized according to Scheme 1.
Scheme 1
12
[0056] Sugar based amphiphiles were synthesized by conventional solution phase methodology
as represented inScheme 1. 60 mL cyclohexane was added to a round bottomed 5 flask followed
by 15 mL of MeOH and kept under N2 atmosphere. Xylitol (4.2 g, 27.5 mmol) and p-TsOH (0.5
g, 2.7 mmol) was added to the solvent mixture and heated to 80��C for 10 min. Then
benzaldehyde (5.6 ml, 55 mmol) was added to the former solution and the whole mixture was
refluxed at 80��C for 2 hours. After the reaction, solvent was removed under reduced pressure on
10 a rotary evaporator to obtain a white solid. The solid was washed with DCM followed by water
and filtered. The product 1 was obtained as a white solid in 90% yield.1H NMR (500 MHz,
CDCl3, rt): �� =7.60-7.58 (dd,4H), 7.54-7.52 (t, 2H), 7.41-7.34 (m, 4H), 5.66 (s, 1H), 5.58 (s, 1H),
4.41-4.39 (dd, 1H), 4.16-4.14 (dd, 1H), 4.09-3.97 (m, 3H), 3.86-3.84 (dd, 2H).
[0057] Compound 2 was also synthesized following the reaction procedure as that of previous
15 reaction but using acetophenone (27.5 mmol) instead of benzaldehyde. The reaction was
performed for 12 hours in this case. The mixturethus obtained after reaction was subjected to
washing by DCM and water and the product was isolated as a white solid after drying in 64%
yield.1H NMR (500 MHz, CDCl3, rt): �� =7.97-7.95 (d, 4H), 7.58-7.55 (t, 2H), 7.48-7.46 (t, 4H),
4.42-4.39 (dd, 1H), 4.23-4.21 (dd, 1H), 4.08-3.87 (m, 3H), 3.55-3.53 (dd, 2H), 1.68 (s, 6H).
20 [0058] Compound 3 was also synthesized following the reaction procedure as that of compound
1 but using phenyl ethyl ketone (27.5 mmol) instead of benzaldehyde. The reaction was
performed for 24 hours in this case. The mixturethus obtained after reaction was subjected to
washing by DCM and water where the product was isolated as a white solid after drying in 62%
yield.1H NMR (500 MHz, CDCl3, rt): �� =7.97-7.95 (d, 4H), 7.57-7.53 (t, 2H), 7.47-7.43 (t, 4H),
13
4.43-4.41(dd, 1H), 4.20-4.17 (dd, 1H), 4.05-3.80 (m, 3H), 3.53-3.50 (dd, 2H), 3.03-2.98 (q, 4H),
1.24-1.21 (t, 6H).
Example 2
Gelation Study with crude oil
[0059] In a typical procedure, 10 mg of the gelator compound of 5 Formula I was added to 0.5 ml
of crude oil in a glass vial with an internal diameter (i.d.) of 10 mm. The mixture was warmed
gently to dissolve the solid compound in crude oil. Then the solution was allowed to cool slowly
to room temperature without disturbance. After few minutes, the solid aggregate mass was found
to be stable to inversion of the glass vial, and then the compound was recognized to form a gel.
10 [0060] To calculate minimum gelation concentration (MGC), gelator was added gradually from
1 mg to higher amount in required solvent/oil (0.5 ml) and the above process (heating and
cooling) was repeated until gel was formed.
[0061] Gel melting temperature was determined by typical tube inversion method. The vial
containing the gel, as prepared above was immersed in the oil-bath ‘upside down’ and slowly
15 heated. The temperature at which the viscous gel melted down was recorded as Tgel.
Gelation Study with other oils and solvents
[0062] The gelation process for crude oil was repeated taking CRN, SRN and diesel as refinery
distillates and taking hexane, octane, dodecane, hexadecane, benzene, toluene and xylene as
solvents (Table 1-3).
20 Table 1: Gelation abilities of compound of Formula I in different hydrocarbon solvents
1 2 3
MGC
(%w/v)
MUC
(%w/v)
MGC
(%w/v)
MUC MGC
(%w/v)
MUC
Hexane P P P … P …
Octane P P P … P ...
Dodecane 1.8 55.5 1.91 52.3 P …
Hexadecane 1.65 60.6 1.75 57.1 1.9 52.6
Benzene 1.16 86.2 1.22 81.9 1.43 69.9
14
Toluene 1.12 89.2 1.2 83.3 1.37 72.9
Xylene 1.05 95.2 1.2 83.3 1.35 74.0
MGC = Minimum Gelation Concentration (amount in g of gelator required for 100 ml of
hydrophobic material to be gelated), MUC = Minimum Uptake Capability (volume in ml
of hydrophobic material gelated by 1 g of gelator), P = Precipitate
[0063] Gelation ability of three compounds is tabulated in the above table. From the table it is
quite evident that gelator compounds are more susceptible to form gel with aromatic solvents
than paraffinic solvents. Their minimum uptake capability towards aromatic solvents varies in
between 70 to 95 times. Gelation ability towards aromatic solvents 5 decreases from 1 to 3 i.e.
with increasing carbon number in the molecule hydrophobicity increases making it tough to be
soluble. Very poor gelation abilities towards paraffinic solvents are exhibited by these three
gelators. All are unable to convert low molecular weight paraffinic solvents e.g. hexane and
octane to their respective gel form. However, hexadecane and dodecane can be converted to gel
10 by gelator 1 and 2. Gelator 3 is active only for hexadecane again signifying its poor gelation
ability. Thus, higher the molecular weight of the paraffinic solvent lower is the MGC. Superior
gelation affinity of these compounds towards aromatic solvents and poor gelation ability for
paraffinic solvents might be due to presence of aromatic rings as hydrophobic part in these
gelator compounds coming from two capping benzaldehyde/aromatic ketone.
15 Table 2: Gelation abilities of compound of Formula I in different oils
1 2 3
MGC
(%w/v) MUC MGC
(%w/v) MUC MGC
(%w/v) MUC
CRN 1.07 93.4 1.28 78.1 P …
SRN 1.31 76.3 P … P …
Kero 0.62 161.2 1.1 90.9 1.84 54.3
Diesel 0.43 232.5 0.62 161.2 0.77 129.8
15
Crude oil 1.69 59.1 1.85 54.0 2.01 49.7
Vegetable oil 0.65 153.8 0.78 128.2 0.92 108.6
MGC = Minimum Gelation Concentration, MUC = Minimum Uptake Capability, P =
Precipitate
[0064] All three gelators are capable in transforming crude oil into gel phase with different MGC
values. Along with crude oil, different refinery distillates also converted to gel by the gelator
compounds as depicted in Table 2. Poor gelation ability of these compounds with paraffinic
solvents is reflected in their gelation abilities with refinery distillates 5 also. As SRN have least
aromatic content than other distillates, the gelation efficiency for SRN was found to be lowest;
even gelator 2 and 3 was unable to form gel with SRN. CRN having higher percentage of
unsaturations e.g. olefins and aromatics is converted to gel easily than SRN. As we move from
lighter fractions to heavier fractions (from SRN to Diesel via Kero) aromatic content gradually
10 increases resulting successive increment of gelation ability by these gelators. Thus heavier
refinery distillates are easily gelated than the lighter distillates. Crude oil having complex
composition have poor gelation tendency than its various fractions where minimum uptake
capability for crude oil was found to be in between 49 to 59 times whereas, maximum gelation
ability is observed for diesel (upto 232 times). Comparison of gelation ability of 1-3 for crude oil
15 as well for other oils dictates superior gelation ability of 1 followed by 2 and 3. Gelation ability
of three gelators for vegetable oil was also proved, exhibiting minimum uptake capabilities
ranging from 108 to 153 times.
Table 3: Gelation abilities of compound of Formula I in different crude oils
1 2 3
MGC
(%w/v) MUC MGC
(%w/v) MUC MGC
(%w/v) MUC
(C1, API = 18.8) 2.33 42.9 2.42 41.3 2.53 39.5
16
(C2, API = 27.1) 2.1 47.6 2.2 45.4 2.35 42.5
(C3, API = 28.1) 2.106 47.4 2.12 47.1 2.22 45.0
(C4, API = 35.5) 1.69 59.1 1.85 54.0 2.01 49.7
(C5, API = 40.5) 1.92 52.0 2.1 47.6 2.21 45.2
MGC = Minimum Gelation Concentration, MUC = Minimum Uptake Capability
[0065] In order to check the effect of the composition of crude oil on the gelation ability of the
organogelator, experiments were conducted with crudes with varying API gravities ranging from
very low API (C1, 18.8��) to high API (C5, 40.5��). Table 3 describes the effect of API gravity
(crude composition) on the uptake (MGC) capability of the gelators. Higher 5 gelation ability is
again exhibited by 1 than 2 and 3. It is evident from Table 3 that heavy crude (lower API) have
higher MGC and lighter crude (higher API) have lower MGC and the uptake capability
decreased with increase in API gravity. Higher the resins & asphaltenes content in the crude,
lower is its API gravity.Thereby a reduction in the uptake capacity with lowering API may be
10 attributed to successive percentage increase of resins & asphaltenes content in crude oil. This
trend is discontinued when moving from API 35.5 to 40.5 and this phenomenon can be explained
according to higher paraffinic content in extra light crude (API 40.5) as thesegelators have poor
gelation capability for paraffinic solvents. However, minimum uptake capability ranging from 40
to 60 times for various crude oils arequite remarkable regarding compositional complexities of
15 the crude oils. These findings indicatethat the composition of crude oil played a major role in the
oil uptake capability by the gelator compounds. Hence these gelators could be used for the most
of the crudes covering the wide spectrum of crude basket available from different parts of the
globe.
Example 3
20 Selective Gelation of crude oil from a Biphasic Mixture of Oil and Water
[0066] In a typical procedure, 0.5 mL of crude oil and 0.5 mL of water were taken in a sample
tube to which 10 mg of the gelator compound of Formula I (as required to attain at least MGC)
was added (Table 4). The gelator was then solubilized in this two-phase solution by heating.
17
After the mixture was cooled to room temperature, the crude oil layer was gelated, keeping the
water layer intact in the liquid state.The same process was followed for other oils like CRN,
SRN, Kero, diesel and vegetable oil.
Table 4: Gelation abilities of compound of Formula I in various oil-water mixtures
1 2 3
MGC
(%w/v) MUC MGC
(%w/v) MUC MGC
(%w/v) MUC
CRN-Water 1.2 83.3 1.31 76.3 P …
SRN-Water 1.4 71.4 P … P …
Kero-Water 0.65 153.8 1.17 85.4 1.85 54.0
Diesel-Water 0.5 200 0.73 136.9 0.8 125
Crude-water 1.8 55.5 1.96 51.0 2.05 48.7
Veg Oil-Water 0.7 142.8 0.81 123.4 0.98 102.0
MGC = Minimum Gelation Concentration, MUC = Minimum Uptake Capability
5
[0067] Selective gelation of oil from a biphasic mixture of oil and water was performed and the
results are noted in Table 4. Six oil samples containing crude oil, refinery distillates as well as
vegetable oil were subjected for gelation experiment prior to practical application in oil spillage.
All three gelators were able to gelate exclusively the oil phase without altering the water phase
during performance evaluation gelation experiments. Gelation abilities 10 of the gelators follow the
same order as reported in Table 2 i.e. gelation ability of 1>2>3. SRN was unable to be gelated by
2 and 3 whereas CRN was unable to be gelated by 3. Selective gelation of other oils was
successful and there was no significant alteration in their gelation abilities in biphasic mixture
ascomparedto that of individual oils from table 2. MGCs for all oils were increased not more
15 than 0.2 % (w/v) from their respective individual/single phase studies. Thus, oil over water can
be contained using these gelators leaving water phase unaffected.
Example 4
18
Selective Gelation of crude oil from a Biphasic Mixture of Oil and Salt Solution:
[0068] In a typical procedure, 0.5 mL of crude oil and 0.5 mL of 3.5% of NaCl solution
(equivalent salt concentration to that of sea water) were taken in a sample tube to which required
of the gelator compound of Formula I was added. The gelator was then solubilized in this twophase
solution by heating. After the mixture was cooled to room temperature, 5 the crude oil layer
was gelated, keeping the water layer intact in the liquid state. The same process was followed for
other oils like CRN, SRN, Kero, diesel and vegetable oil.
Table 5: Gelation abilities of compound of formula I in various oil-sea water mixture
1 2 3
MGC
(%w/v)
MUC MGC
(%w/v)
MUC MGC
(%w/v)
MUC
CRN-Sea Water 1.2 83.3 1.35 74.07 P …
SRN-Sea Water 1.38 72.4 P … P …
Kero-Sea Water 0.65 153.8 1.2 83.3 1.85 54.0
Diesel-Sea Water 0.48 208.3 0.75 133.3 0.82 121.9
Crude-Sea water 1.81 55.2 1.95 51.2 2.1 47.6
Veg Oil-Sea Water 0.7 142.8 0.8 125 1.0 100
MGC = Minimum Gelation Concentration, MUC = Minimum Uptake Capability
10 [0069] Oil Selective gelation of oils from a biphasic mixture of oil and sea water was also
performed and the results are tabulated in Table 5. Again the gelator compounds1-3were able to
gelate exclusively the oil phase without altering the sea water phase during performance
evaluation gelation experiments. Comparison of the results from Table 4 and Table 5 clearly
dictates that even under highly saline conditionsMCG & MUC for those oils remained almost
15 unchanged. Thus, strength and capability of the organogelators towards gelation for organic
phase is highly encouraging even under extreme conditions reveling practical application
towards oil spillage recovery over sea.
Example 5
19
Oil Spill Recovery:
Oil spill recovery was performed taking 10 ml of SRN over 20 ml of water. An ethanolic
solution of the compound of Formula I (0.25 g in 5 mL of ethanol, 5 w/v%; only 2.5 ml of the
ethanolic solution was used for 10 ml of SRN) was added to the SRN-water mixture and allowed
to stand for about 15 min where SRN phase was transformed to 5 the gel keeping the water layer
intact in the liquid state. The gel phase was filtered off and processed to recover the oil.
Example 6
Room Temperature Gelation of Crude Oil from a Biphasic Mixture of Oil and Salt
Solution:
10 For the phase selective gelation purpose volatile and oil miscible solvent dichloromethane
(DCM) was used. In a typical procedure 10% solution of the gelator was prepared by dissolving
it in DCM at room temperature without applying heat. To a 25 ml of crude oil layer over 100 ml
of salt solution the gelator solution was applied to ensure complete dispersion. Within a few
minutes volatile DCM is evaporated and the crude oil layer is transformed to the gel state.
15 Utilizing the volatile solvent e.g. DCM, phase selective gelation of crude oil as well as other oil
fraction are possible. The advantage of this process is that without applying any heating and
cooling process phase selective gelation is possible making the process very much economical.
Thus the process can be applied for larger scale for practical remediation of oil spillage.
Generally use of other hydrophobic solvent e.g. toluene, diesel or SRN for phase selective
20 gelation require excess amount of gelator to congeal the oil phase as well as carrier solvent but,
applying our above said process these drawbacks can be neglected and maximum efficiency can
be achieved.
Example 7
Reclaiming solvent from Gel
25 [0070] 10 ml of SRN was transformed into gel phase using 80 mg of compound of Formula I.
The gel was then subjected to vacuum distillation for oil phase recovery. After successful
distillation 8.9 ml of SRN was recovered leaving white powder of the gelator compound with
89% of solvent recovery.The vacuum distillation was carried out at 60oC for 1 hour.
20
Advantages gained in the example illustrative process in this subject matter:
[0071] Environmentally benign sugar based phase selective gelator has been developed for oil
phase gelation from a mixture of oil and water. The gelatorsefficiently work even at a very low
concentration and at room temperature. The gelators find application in marine oil spill
recovery.Oil from the gel can be recovered and gel can be recycled 5 and reused for number of
cycles without loss of activity
[0072] Although the subject matter has been described in considerable detail with reference to
certain examples and implementations thereof, other implementations are possible. As such, the
spirit and scope of the appended claims should not be limited to the description of the preferred
10 examples and implementations contained therein.
15
20
21
I/We Claim:
1. A compound having the Formula:
5 Formula I
wherein,
R1 and R2 are independently selected from hydrogen or C1 to C6 alkyl.
2. The compound as claimed in claim 1, wherein R1and R2 arehydrogen
10 3. The compound as claimed in claim 1, wherein R1 is hydrogen and R2 is C1 to C6 alkyl.
4. The compound as claimed in claim 1, wherein R1 is C1 to C6 alkyl and R2 is hydrogen.
5. The compound as claimed in claim 1, wherein R1 and R2 are C1 to C6 alkyl.
6. The compound as claimed in claim 1, wherein R1 and R2 are is C1 alkyl.
7. The compound as claimed in claim 1, wherein R1 and R2 are is C2 alkyl.
15 8. A method of preparing the compound as claimed in claim 1.
9. A gel comprising a compound as claimed in claim 1 and a solvent.
10. The gel as claimed in claim 9, wherein the solvent is selected from water, an organic
solvent, or mixtures thereof.
11. A method for preparinga gel comprising contacting the compound as claimed in claim
20 1 with a solvent.
12. The method as claimed in claim 11, wherein the solvent is selected from water, an
organic solvent, or mixtures thereof.
13. The method of claim 11, wherein the solvent is a hydrocarbon.
14. The method of claim 11, wherein the solvent comprises a mixture of a hydrocarbon and
25 water.
15. A method of containing the spill of a hydrocarbon, the method comprising contacting the
hydrocarbon with the compound as claimed in claim 1 to obtain a gel.
22
16. A method of reclaiming solvent and a compound as claimed in claim 1 from the gel as
claimed in claim 9.