US 2011 OO60.

048A1
(19) United States
(12) Patent Application Publication (10) Pub. No.: US 2011/0060048A1
L0 (43) Pub. Date: Mar. 10, 2011
(54) REMOVING ALCOHOL IN VIVO THROUGH (57) ABSTRACT
ESTERIFICATION
The present invention is pertaining to a method to chemically
remove ethanol in the stomach before a significant amount of
(76) Inventor: Atly Regina Lo, San Diego, CA ethanol enters the blood stream. The key chemical reaction
responsible for ethanol removal is esterification through a
(21) Appl. No.: 12/554,899 reaction between ethanol and acetic acid. Ethanol reacts with
acetic acid to produce water and ethyl acetate, which is a
(22) Filed: Sep. 5, 2009 harmless ester found in many food products. In theory, if an
intoxicated individual consumes a molar quantity of vinegar
Publication Classification similar to the amount of ethanol in the alcoholic beverage,
much of the ethanol will be converted into harmless products.
(51) Int. Cl. Low cost, practical methods for alcohol drinkers to orally take
A6 IK3I/I9 (2006.01) a sufficient amount of acetic components are invented. These
A6 IK3I/I94 (2006.01) methods include drinks containing a mixture of acetic acid
(52) U.S. Cl. ......................................... 514/574: 514/557 and potassium hydroxide with an appropriate level of acidity.
US 2011/0060048 A1 Mar. 10, 2011

REMOVING ALCOHOL IN VIVO THROUGH eliminated through urination and respiration. However, the
ESTERIFICATION alcohol oxidase does not naturally exist in the human body in
Sufficient amounts, and is very costly. A Solution containing
BACKGROUND approximately 17,200 EU of alcohol oxidase is needed to
neutralize the ethanol in a can of beer within 15 minutes. This
0001 Ethanol (CHOH) is a depressant that is present in amount of enzyme will cost nearly $370. A method that
all alcoholic beverages in varying percentages. On an empty requires nearly four hundred dollars to reverse the effects of a
stomach, 20% of the ethanol consumed almost immediately single serving of a mild alcoholic beverage cannot be applied
diffuses into the bloodstream through the walls of the stom commercially, or developed into an easily-accessible sobriety
ach. Within 30 minutes, all of the ethanol will have entered the drug.
blood, and clear symptoms can be observed if the BAC (blood 0008. Another method was published in a 1975 volume of
alcohol content) of the drinker is over 0.08. Years of chronic the American Journal of Clinical Nutrition, for removing
drinking leads to lasting damage on vital organs. ethanol from the body through ingesting Sugars. Eight male
0002 Effects of alcohol on various parts of the body are volunteers 25-50 years old, of approximately the same height
summarized below: and weight, were each given a few servings of alcoholic
0003 1. The liver: The majority of alcohol consumed is beverage, followed by 30 grams of fructose or sucrose. Mea
transported to the liver to be converted into harmless Surements were taken each hour, and the percent of ethanol
products. As a result, 15% of all alcohol-related deaths decrease flattened out at 29% on average. This experiment is
are attributable to liver failure. Liver damage begins with dubious, because a). It only eliminated 29% of the ethanol
the hepatotoxic effect (aka fatty liver), and inflicts mod from the bodies of the drinkers, and thus does not appear to be
erate, reversible damages on the liver. If drinking con a very efficient antidote, b). Fructose is very expensive, and
tinues, Scarring and inflammation will deteriorate, and c). It promotes a high-Sugar diet.
eventually culminate in liver cirrhosis, which is irrevers 0009. As will be discussed below, the use of the acetate ion
ible and usually fatal. to neutralize ethanol is a much more efficient method.
0004 2. The brain: Short term effects include drowsi
ness, loss of coordination, dizziness, and mood Swings. SUMMARY OF INVENTION
Long-term effects include memory loss, strokes, and 0010. The key principle of this invention for ethanol
concussions.
0005 3. Reproductive system: In males, alcohol abuse removal is ethanolesterification with acetic acid, as described
results in prostate inflammation and erectile disorder. In in the following reaction:
women, it results in irregular menstrual cycles, hor CH-OH-CHCOOH-CHCHOCOCH.K.
M 45
monal imbalance, infertility, and—if pregnant physi
cal deformities and mental retardation in the fetus. 0011. In an in-vitro test, a known volume (17.15 mL) and
Alcoholism has far-reaching ramifications on both individu concentration (0.4M, 0.6M, 0.8M, 10M) of ethanol reacted
als and Society. Although it is impractical to forbid people with the same Volume and concentration of acetic acid. Titra
from drinking altogether, there is a need to limit its effects. tions with potassium permanganate (KMnO) were later per
formed after the contents of each beaker received 5 minutes
Prior Arts: each of vigorous stirring and 25 minutes of inactivity to
0006. In January 2008, a patent was filed under the name compare the final amount of ethanol left with the original
“Method for the Accelerated in Vivo Removal of Ethanol amount. In agreement with the calculations done using the
(U.S. Pat. No. 7,323,452). The patent stated that the liver known equilibrium constant of K-45 M', a 79-86%
decrease in the amount of ethanol was demonstrated when the
naturally converts ethanol into acetaldehyde using an enzyme system reaches equilibrium. Average results calculated after 5
called alcohol dehydrogenase, but that the equilibrium con trials were within a 4% margin of error, as shown in Table 1.
stant of 1 indicated inefficiency. It suggested that a pill, cap
Sule, or nasal spray containing chemicals accelerators in the TABLE 1
direction of acetaldehyde (such as zinc ions) could be added
in order to increase the proportion of ethanol that was being In vitro experiment of esterification with different values of initial
eliminated. However, this proposal is based on the assump ethanol and acetic acid concentrations. The last column indicates
tion that ethanol has already entered the bloodstream, and the amount of decrease in the ethanol concentration after the
System reaches equilibrium.
must be eliminated from there. By the time ethanol has
entered the bloodstream, it is extremely difficult to eliminate Initial
it in large quantities. Ethanol is a very Small molecule (molar C2H5OH =
mass 46 g/mol) compared to the organic macromolecules, Initial Equilibrium Concentrations % Ethanol
and even molecules Such as glucose and amino acids, that CHCOOH CH-OH=CHCOOH CHCHOCOCH, Decrease
normally circulate throughout the bloodstream. Its solubility
in water additionally allows it to circulate rapidly throughout O4 M
O.SM
O.O84M
O.095 M
O.316M
O4OSM
79.0%
81.0%
the body. Clearly, the removal process must take before etha O.6M O.1OSM O49SM 82.5%
nol enters the bloodstream. O.7M O. 114 M O.S86M 83.7%
0007. In 1984, a patent was filed under the title of "Alcohol O.8M
O.9 M
O.123 M
O.131 M
O.677M
O.769 M
84.6%
85.4%
removal from blood with alcohol oxidase (U.S. Pat. No. 1.OM O.138M O.862 M 86.2%
4.450,153). Alcohol oxidase is an enzyme that converts etha
nol into acetaldehyde in the following method: primary alco
hol--O<san aldehyde--HO. After the aldehyde is produced, The amount of alcohol intake before reaching the DUI level
it naturally decays into water and carbon dioxide, which are could vary widely among individuals and depends on many
US 2011/0060048 A1 Mar. 10, 2011

factors such as weight, age, gender, and race. It is generally 0016. Although we have used acetic acid as an example to
believed that, for most people, four cans of beer or an equiva turn the harmful ethanol into a product that is more benign,
lent amount of ethanol taken over a time period of 1-2 hours one can choose other organic acid such as citric acid to
can influence people's health, behaviors, and judgment. Four achieve the similar effect. Each citric acid molecule contains
cans of beer contain approximately 1 mole of ethanol. three functional sites to react with three ethanol molecules to
According to the above in vitro experiment, it will take about generate a product of triethylcitrate. Since citric acid is a
an equal amount (i.e. 1 mole) of acetic acid to Substantially weak acid too, the above mentioned technique of partial neu
reduce the amount of ethanol throughesterification. A 100 ml tralization with strong base is applicable too. It should be
of off-the-counter vinegar (5% acidity), on the other hand, understood that all approaches based on the similar principle
contains only 0.086 mole of acetic acid. It is unconceivable discussed in this disclosure are covered by this invention.
that anyone is able to take 1160 ml of off-the-shelf vinegar in DETAILED DESCRIPTION OF INVENTION
order to effectively remove the ethanol. Both the sheer vol
ume and the acidity of the vinegar make the approach imprac 0017. The first part of the invention is the process of turn
tical. ing ethanol into ester from an oral intake of acetic acid. The
0012. An important part of the invention is about practical reaction of esterification occurs inside stomach. The second
methods to orally take the required amount of acetic acid to part of the invention is the methodology of making oral intake
react with ethanol. A practical approach has to meet two products that contain a Sufficient amount (e.g. 1 mole) of
requirements: (a) Substantially reduce the intake Volume of acetic acid in a relatively small volume (e.g. 75 mil) of proper
acetic acid containing liquid, and (b) introducing the required acidity (e.g. PH: 3-4).
amount (around 1.0 mole) of acetic acid in a harmless and 0018. In the following we describe the detailed procedure
least intrusive manner, meaning to create no acid burn or of in vitro experiment to verify the validity of reducing the
discomfort. In accordance with the invention, these practical amount of ethanol by esterification:
approaches are developed based on one key concept: reduc 0019 1. Label four 100-mL beakers, 0.4M, 0.6 M, 0.8
ing the acidity of concentrated acetic acid with a proper M, and 1.0 M.
amount of strong base to yield a final product having a proper 0020 2. Put 17.15 mL of distilled water into each.
level of acidity, i.e. for a range of PH value between 3-4. For 0021 3. Add 0.4 mL of concentrated ethanol to the first
references, the PH value is 2.9-3.3 for apple juice, 3-4 for beaker, 0.6 mL to the second, 0.8 mL to the third, and 1.0
orange juice, and 4.2 for tomato juice. Possible choices of mL to the fourth. Swivel each beaker gently for 20-30
strong base include NaOH and KOH. Added to concentrated seconds to ensure mixing. See calculations below for
acetic acid, the solution contains CHCOONa or CHCOOK explanation.
and CHCOOH with lower acidity. The mixed solution con 0022 4. Add another 17.15 mL of water to each beaker
tains sodium and/or potassium, and the amount should be 0023 5. Add 0.4 mL of glacial acetic acid to the first
kept well below the FDA recommended daily allowance. beaker, 0.6 mL to the second, 0.8 mL to the third, and 1.0
Since it is less desirable to create high sodium-containing mL to the fourth. See calculations below for explanation.
drinks, KOH becomes a more attractive choice of base to 0024 6. Stir each sample vigorously for five minutes in
partially neutralize the acetic acid. succession. Each beaker will have had a total of twenty
0013 The detailed analysis, to be discussed in the follow minutes for the reaction to proceed.
ing section, Suggests the following practical recipe: 0.025 7. Put on latex gloves before handling potassium
permanganate.
Adding 0.02 mole of KOH (20% FDA recommended daily 0026 8. Set up two burettes, and fill each with approxi
dosage for potassium) to 1 mole of 50% concentrated acetic mately 100 mL of 0.2M potassium permanganate. This
acid, one can take 1 mole of acetic acid in a 75 mil drink at a will enable two titrations to be simultaneously done.
PH-value of around 3.3.
0014) Numerous recipes following the similar principle 0027 9. Record the initial volume of potassium per
manganate present in both burettes.
can be created to produce essentially the same effect of turn 0028. 10. Place 1.0 M and 0.8 Mbeakers on hot plate,
ing ethanol into ester in stomach. Additional flavors and com and turn to power level 3. Heating quickens the titration
ponents can also be introduced to the drink without altering its process.
function while improving the taste. Furthermore, the same 0029 11. Slowly drip KMnO, into beakers while stir
ingredients can also be incorporated into Solid food Such as ring. Make Sure that each beaker is consistently titrated
cakes, Snack bars, cookies, and other bakeries in manners that with the same burette to ensure that the exact volumes of
the heating process of making such goods will not degrade the KMnO, that each beaker received can be easily calcu
performance. It is also conceivable that the mixed KOH/ lated.
CHCOOH solution may be turned into powder or gel with 0030) 12. Potassium permanganate is purple in color.
extra additives so that it can be packaged into pills that are When reacted with ethanol, a brown color (manganese
easier to carry. oxide, MnO) appears. The reaction is as follows:
0015 The invention produces a solution for removing the
harmful effects of alcohol and is inexpensive, safe and effec 3CHOH+4KMnO->3CHCOOH-4MnO+4KOH+
tive. Compared to approaches that use enzymes, acetic acid HO
and bases such as KOH and NaOH are easy to obtain in large When potassium permanganate ceases to be converted into
quantities at very low cost. In addition, all ingredients manganese oxide, and the purple color stays, the titration is
(CHCOOK and CHCOOH) are safe to use and their daily finished. There is no ethanol left in the beaker to react with
dosages (e.g. K and Na) are well established. Therefore, the potassium permanganate.
product can be off the counter without prescription. It does 0.031) 13. Remove both beakers from hot plate. Measure
not require FDA approval either. the Volume of potassium permanganate remaining in
US 2011/0060048 A1 Mar. 10, 2011

each burette. Subtract from the original volumes to find stronger acetic acid than the off-the-counter white vinegar
the volume of KMnO consumed in each reaction. and the solution is corrosive and could cause acid burn, not
0032) 14. Repeat steps 9-13 for the 0.6 M and 0.4 M suitable for oral intake.
beakers. 0042. For 0.1% highly diluted vinegar, X-0.03 M, the PH
0033 15. Use stoichiometry to calculate the molar value, according to Eq. (2), becomes 3.3. This is close to the
amount of 0.2 M potassium permanganate used in each PH value of applejuice and orange juice, a PH value we are
titration. used to in food and beverage. Our approach is to create an
0034 16. Ethanol and potassium permanganate react in acetic Solution containing a large enough amount of acetic
a 3:4 molar ratio, according to the equation3CH3OH+ acid while keeping the PH value at the level of fruit juice.
4KMnO->3CHCOOH-4MnO+4KOH+H.O. 0043. Next we calculate how the PH value of the acetic
0035. Again, use a chain calculation to calculate the molar solution changes with the addition of a small amount of KOH.
amount of ethanol remaining in each beaker, then divide by Before reaction, we assume the initial molar concentration of
0.01715 mL HO to convert to molarity. Compare to the CHCOOH and KOH is X and Y, respectively. We also
molarity of ethanol originally in each beaker. Calculate % assume that we have a large amount of CHCOOH so the final
eO. PH value of the solution is slightly acidic. This assumption
0036) 17. Results (see Table 2) works for our purpose because we try to maximize the amount
of CHCOOH but control the amount of KOH so the potas
TABLE 2 sium intake can be kept well within the FDA recommended
daily dosage (i.e. 4 g or 0.1 mole of potassium).
Summary of the results of 5 repeats of in vitro experiment. 0044. After equilibrium is reached, the final concentration
The last column indicates the amount (in percentage) of reduction for each component becomes:
in ethanol with the addition to acetic acid.

Initial C2H5OH% Decrease at Equilibrium

CHCOOH = X -u, CH3COO = u, H = u - Y > 0
CH-OH Trial 1 Trial 2 Trial 3 Trial 4 Trial 5 Average
K, (CH3COOH => it - Y = K(X - it) (3)
O4 M 78.1% 81.5% 81.2% 80.0% 80.2% CHCOO) ii.
O.6M 82.7% 83.8% 83.7% 82.5% 83.2%
O.8M 89.1% 86.2% 84.7% 84.6% 85.5% 86.0%
1.OM 91.3% 88.8% 86.5% 91.1% 90.4% 89.6%
0045 Since acetic acid is a weak acid with a very low
value of K?1, we can find an approximate solution for u:
Table 2 summarizes the results of 5 repeats of experiment.
The results indicate that over a wide range of ethanol concen
tration relevant to our application, adding an equal molar
number of acetic acid to the ethanol solution can reduce the ii. a
2.
--
2
ethanol amount by as much as 80-90%.
0037. The second part of the invention is regarding to the
methodology of creating products that contain a sufficient 0046. Then the PH value can be represented as
amount (e.g. 1 mole) of acetic acid in a relatively small
volume (e.g. 75 mil) with proper acidity (e.g. PH: 3-4). The
design principle and analysis are discussed in the following: w Y’ + 4.K., X Y --- Ko X X (5)
0038 We use KOH as an example to reduce the acidity of PH = -logo — — — 5- -logo y =5 -logo
a large amount of CHCOOH so that one can comfortably
drink enough amount of acetic acid by mouth to remove
alcohol in the stomach. 0047 Table 3 shows the PH value of the solution for dif
0039. The chemical reaction for dissociation of ferent concentration ratios between CHCOOH and KOH
CHCOOH: before mixture.

TABLE 3
CH3COOH- CH3COO + H" (1)
Dependence of PH value of the solution on the ratio of
(CH,COOH"). -5 CH3COOH and KOH before reaction.
Ka = CHCOOH- Ka = 1 x 10 M
X/Y: initial ratio of ICHCOOH) and KOH) PH value at equilibrium
10 4.0
0040. If we do not add any KOH, then the PH value of 50 3.3
CHCOOH becomes 1OO 3.0

1 (2) 0048. This result is highly significant. It shows that we can

PHCH, Cooh s -logo WKX = 2.5- 5 logo X mix KOH with 50 times as much as CHCOOH while main
taining an acidity level comfortable for drinking (i.e. equiva
lent to 0.1% highly diluted acetic acid).
0041. Where X is the molar concentration of CHCOOH. 0049. The daily recommended potassium (K) intake is 4 g.
For 50% acetic acid, X=13.5 M. From Eq. (2), the acetic equivalent to 0.1 moles. That means the above approach
solution has a PH value of 2.0. Note that this is 10 times allows us to take as many as 5 moles of acetic acid without
US 2011/0060048 A1 Mar. 10, 2011

feeling acid burn or discomfort 5 moles of acetic acid is (d) the base in the composition contains ions of an alkali or
much more than we need for ethanol esterification since 4 alkaline earth metal.
cans of beer contain only a total amount of 1.0 mole of 12. The composition of claim 11, wherein the alkali metal
ethanol. is potassium.
0050. While the invention has been described in connec 13. The composition of claim 11, wherein the alkali metal
tion with various embodiments, it is not intended to limit the is sodium.
scope of the invention to the particular form set forth. It is 14. The composition of claim 11, wherein the alkaline earth
intended to cover Such alternatives, modifications, and metal is calcium.
equivalents as may be included within the spirit and scope of 15. The composition of claim 11, wherein the alkaline earth
the invention as defined by the appended claims metal is magnesium.
We claim: 16. The composition of claim 11, wherein the composition
1. A process for in vivo esterification of ethanol, compris is in liquid form.
ing the steps of 17. The composition of claim 11, wherein the composition
(a) preparing a composition containing acetic acid and a contains food color, or food flavor, or other ingredients to
base wherein the base partially neutralizes the acetic make the composition more palatable to take orally.
acid to a PH value of greater than 2.5; and 18. The composition of claim 11, wherein the composition
(b) administering the composition in vivo to reduce the is solidified with additional process and additives.
amount of ethanol by turning a certainamount of ethanol 19. The composition of claim 11, wherein the liquid is
into ester, and mixed with other ingredients to become a form of solid food
(c) the reaction of esterification occurs mostly within stom or pill that can be taken orally.
ach in an acetic environment and in the presence of 20. A composition to be taken orally to reduce the amount
stomach juice. of ethanol inside body
2. The process of claim 1, wherein the base contains potas (a) the composition contains at least 0.1 mole of organic
sium hydroxide. acid;
3. The process of claim 2, wherein the amount of potassium (b) the composition contains a base solution to increase the
is less than 8 grams or 200% of FDA recommended daily overall PH value above 2.5;
dosage. (c) the composition can react with ethanol to form ester in
4. The process of claim 1, wherein the base contains V1Vo:
Sodium hydroxide. (d) the base in the composition contains ions of an alkali or
5. The process of claim 4, wherein the amount of sodium is alkaline earth metal.
less than 4.6 grams or 200% of FDA recommended daily 21. The composition of claim 20, wherein the organic acid
dosage. is citric acid.
6. The process of claim 1, wherein the base contains cal 22. The composition of claim 20, wherein the alkali metal
cium hydroxide. is potassium.
7. The process of claim 1, wherein the composition is in 23. The composition of claim 20, wherein the alkali metal
liquid form. is sodium.
8. The process of claim 1, wherein the composition con 24. The composition of claim 20, wherein the alkaline earth
tains food color, or food flavor, or other ingredients to make metal is calcium.
the composition more palatable to take orally. 25. The composition of claim 20, wherein the alkaline earth
9. The process of claim 1, wherein the composition is metal is magnesium.
solidified with additional process and additives. 26. The composition of claim 20, wherein the composition
10. The process of claim 5, wherein the liquid is mixed with is in liquid form.
other ingredients to become a form of solid food or pill that 27. The composition of claim 20, wherein the composition
can be taken in by mouth. contains food color, or food flavor, or other ingredients to
11. A composition to be taken orally to reduce the amount make the composition more palatable to take by mouth.
of ethanol inside body 28. The composition of claim 20, wherein the composition
(a) the composition contains at least 0.1 mole of acetic is solidified with additional process and additives.
acid; 29. The composition of claim 20, wherein the liquid is
(b) the composition contains a base solution to increase the mixed with other ingredients to become a form of solid food
overall PH value above 2.5; or pill that can be taken orally.
(c) the acetic acid in the composition can react with ethanol c c c c c
to form ester in vivo;