9/24/2020 CA1193610A - Production of indanes - Google Patents

 Patents

Production of indanes

Abstract
CA1193610A
ABSTRACT
Canada

The reaction between particular styrenes and particular alkenes to produce alkyl substituted indanes
has been discovered to give improved yields when phosphoric acid is used as the catalyst. The Find Prior Art Similar
catalyst is readily separated from the organic products at the end of the reaction and can be used
repeatedly to catalyse further reactions. The product further comprises novel adducts of the alkene Other languages: French
and styrene which are converted into the desired isochroman products when the indanes are used
Inventor: Peter J. Goddard, Gerald J. Ferber
as intermediates in the production of isochromans.
Current Assignee : Solvay Solutions UK Ltd

Classi cations
Worldwide applications
C07D311/76 Benzo[c]pyrans
1982 CA US ES DE DK AT EP JP ES
View 5 more classi cations
Application CA000398073A events

1981-03-13 Priority to GB8108050

1981-03-13 Priority to GB8108050

1982-03-11 Application led by Albright and Wilson Ltd

1985-09-17 Application granted

1985-09-17 Publication of CA1193610A

Status Expired

Info: Patent citations (11), Cited by (4), Legal events, Similar

documents, Priority and Related Applications

External links: Espacenet, Global Dossier, CIPO, Discuss

Claims (20) Hide Dependent

The embodiments of the invention in which an exclusive property or privilege is claimed are de ned as follows:

1. A process for the production of an indane of the formula:

wherein R3 represents a hydrogen atom or a methyl group, at least one of R1 and R2 represents a methyl group and the other represents a hydrogen atom or a methyl group;
and R4 and R5 which may be the same or different represent alkyl groups having from 1 to 3 carbon atoms, which com-prises reacting a styrene of the formula (1):

(1) wherein R1 represents a hydrogen atom or a methyl group;

with an alkene which is selected from the group consisting of propylene, 2 methyl but-1-ene, 2 methyl but-2-ene, 2 methyl pent-1-ene, 2 methyl pent-2-ene, 3 methyl but-1-ene,
isobutylene and diisobutylene, in the presence of an acid catalyst which is an aqueous solution of phosphoric acid consisting of above 85% by weight of phosphoric acid.

2. A process according to claim 1, wherein, in the styrene having the formula (1), R1 represents a methyl group.

3. A process according to either of claim 1 or 2, wherein the alkene is selected from the group comprising 2 methyl-but-1-ene, 2 methyl-but-2-ene and isobutylene.

4. A process according to claim 1, wherein the catalyst is an aqueous solution of phosphoric acid which comprises less than 95% w/w phosphoric acid.

5. A process according to claim 1, wherein the catalyst is an aqueous solution of phosphoric acid which comprises 88 to 92% w/w phosphoric acid.

6. A process according to claim 1, wherein a quantity of from 1.0 to 5.0 moles of phosphoric acid per mole of styrene is employed.

7. A process according to claim 6, wherein from 1.25 to 2 moles of phosphoric acid per mole of styrene is employed.

8. A process according to claim 1, wherein the reaction is carried out at a temperature in the range 0° to 50°C.

9. A process according to any one of claims 5, 7 or 8, wherein the reaction is carried out at a temperature of from 25° to 35°C.

10. A process according to claim 1, wherein the reaction product mixture separates into an organic layer containing the indane and an acid layer containing the
phosphoric acid catalyst, the layers are separated and the acid layer is reused as the acid catalyst in a subsequent reaction of styrene and alkene.

11. A process according to claim 1, wherein R1 and R2 represent methyl groups.

12. A process according to claim 1, wherein R4 and R5 represent methyl groups.

13. A process according to any of claim 1, 11 and 12, wherein R3 represents a methyl group.

14. A process according to claim 1, wherein there is produced a mixture of the compound wherein R1 R2, R3, R4 and R5 each represent a methyl group with the
compound wherein R1, R2 and R4 each represent a methyl group, R3 represents a hydrogen atom and R5 represents an ethyl group.

15. A process according to claim 14, wherein the product mixture comprises 2,3,4-trimethyl-4-phenyl-pent-1-ene and 2,4-dimethyl-2-phenyl-hex-4-ene.

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16. A process according to claim 1, wherein the product indane is further reacted with an alkylene oxide in the presence of an electrophillic catalyst and subsequently
with formaldehyde to produce an isochroman of the formula:

when produced by the process of claim 1.

17. A process according to claim 16, wherein the indane reactant comprises indane precursors and is obtained by fractional distillation of the product of a process
accord-ing to claim 1.

18. A process according to claim 17 wherein the indane precursors are 2,3,4 trimethyl-4-phenyl-pent-1-ene and 2,4 dimethyl-2-phenyl hex-4-ene.

19. 2,3,4-trimethyl-4-phenyl-pent-1-ene.

20. 2,4-dimethyl-2-phenyl-hex-4-ene.

Description

~193~
~ 1 --This invention relates to a novel process for the production of polyalkyl indanes which are useful as intermediates in the synthesis of a variety of valuable organic
chemicals. They nd particular appl ication as ;ntermediates in the production of a variety o~ polycyclic compcunds which a~e useful as Lngredients c~
compounded perfumery ccmpositions.

United States Patent No. 2,851,501 describes the utility of polyalkyl indanes having the formula:-~ 3 Rt ~
wherein R1 6 represent hydrogen atoms or alkyl groups comprising1 to 3 carbon atoms as intermediates in chemical synthesis.

A convenient method for the production of these indanes is the reaction between a styrene and an alkene in the presence of an acid catalyst,such as is described in
United States Patent No-15 2,851,501 a~d Br~tish Patent No. 991,146~ U.S. P~tent No~ 2,851,501 states that the reaction should be carried out in the presence ofa
catalyst which is an acid acting catalyst. Speci c ca~alysts which are suggested as being useful are sulphuric acid and phosphoric acid (as aqueous solutions having
concentration of 70 to 85~ acid or in the presence of monobasic organic acids haviny from 1 to 3 carbon atoms,such as formic acid, propionic acid, chloro-substituted
acetic acid etc.~, boron tri uoride, zinc chloride and their complexes such as their etherates or mixtures of any one of these with monob2sic organic acids having from 1
to 3 carbon atoms and monobasic organic acids having a dissociation constant of 1.76 x 10-4 or more, such as formic acid and halogenated acetic acids.
The processes exemplif;ed in this patent employ a mixture of su1phuric acid with acetic acid as the catalyst in all of the examples except one in which a complex of
boron tri uoride and .. ~ .

methyl ether is used. The use of an organic acid with the sulphuric acid promotes mutual solubility between the acid and organic phases in a two phase system. This
mutual solubility leads to some organic acid being dissolved in the organic phase at the end of the reaction. This is disadvantageous in that this dissolved acid has to be
washed out from the organic product and organic acid content of the catalyst system must be replenished.

The organic reaction product is a mixture comprising the desired indanes and dimeric products derived from the alkene and styrene in varying proportions. The formation
of the dimeric products derived fro~ the alkene and the styrene as well as other by-product materia1s reduces the yield of the desired indanes and is thereby
disadvantageous.

I~e have now discovered that the yield of indanes and useful by-products obtained by the reaction of particular styrenes with particular alkenes can be increased by using
phosphoric acid as the catalyst for the reaction. The phosphoric acid readily separates virtually completely from the organic phase at the end of the reaction and can be
recovered and recycled ~ith a high degree of e `cienCY-In accordance with one aspect of the present in~ention, there is provided a process for the production of an
indane of the formula:
R~ RL --\ ~1~A~ F~3 ~;t R5 wherein R3 represents a hydrogen atom or a methyl group, at least one of R1 and R2 represents a methyl ~roup and the other represents a
hydrogen atom or a methyl group,and R4 and R5, which may be the same or different, represent alkyl groups having ,. .

1:~L93~
~ 3 --from 1 to 3 carkon atoms, which comprises reacting a styrene of the forn~la (1):

~ C - CH2 -(1) wherein ~ represents a hydrogen atom or a methyl group with an alkene which is selected from the group consist mg of propylene, 2 methyl but-l-ene, 2
methyl but~2-ene, 2 methyl pent-l-ene, 2 methyl pent-2-ene, 3 methyl but~ e isobutylene and di-isobutylene, in the presence of an acid catalyst which is an aqueous
solution of phosphoric acid consisting of above 85~ by weight of phosphoric acid.
The novel processes of our invention may also be carried out utillsing an alcohol as the reactant in place of the alkene, the alcohol being such that it is capable of being
dehydrated to form alkenes under the conditions employed for the reaction. Examples of alcohols which may be employed are tertiary amyl alcohol (which acts as a
precursor of 2 methyl-but-2-ene and 2 methyl but-1-ene) and

2-methyl propan-1-ol, 2 methyl propan 2-ol, secondary amyl alcohol, tertiary methyl pentanol and 2-methyl-pentan-3-ol.

The phosphoric acid may contain minor quantities e.g. less than 20~ of the acid content, of other acids, but preferably no other acid is present.

The phosphoric acid catalyst is preferably employed in the form of an aqueous solution thereof containing from 85 to 9S~ or preferably 88 to 92~ by weight of
phosphoric ac.id. The quantity of phosphoric acid which is employed may vary through a wide range but preferably a quantity of from 1.0 to 3.0, or most preferably about
1.25 to 2.0, moles of acid per mole of alkene reactant are employed.
The reaction can conveniently be carried out by reacting substantially equimolar quantities of styrene and alkene.
Preferably the quantity of the styrene is least equal to the quantity of alkene and it may be employed in excess quantities, e.g. up to 3.0 moles of styrene per moles of
alkene.

;~

36~

The reaction may conveniently be carried out by the gradual addition of a mixture of the styrene and alkene reactants to the catalyst in an appropriate reaction vessel.
The temperature of the reaction medium is perferably maintained within the range 0 to 50~ or more preferably in the range 2~ to 35c, mDst preferably 25 to 30C. The
phosphoric acid r~y be a liquid phase, a supercooled liquid cr a slurry of phosphoric acid crystals in a liquid phase,depending upon the concentration of acid used and the
temperature employed. The reaction medium is usually stirred in order to ensure thorough mixing, and preferahly su ciently strongly to achieve the formation of of a
meta-stable emulsion. It may be advantageous to add a small quantity,e.g. 1 or 2%,of an emulsifying agent or agents (usually a cationic or non-ionic emulsifying agent) to
the reaction medium in order to encourage the formation of such an emulsion. The quantity of any such additive should be carefully controlled so as to avoid the

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formation of a stable emulsion at the end of the reaction thereby allowing the acid and organic phases to separate. The presence of impurities in the reactants, especially
the styrene, may prevent the formation of a meta-stable emulsion during the reaction and it may be preferable to purify the reactants e.g. by fractional distillation prior to
the reaction.

The rate of addition of the reactants is adjusted so as to .;;s ~936~

~.~

help maintain the temperature of the reaction medium within the desired range. Normally the addition will be completed within a period of from 2 to 6 hours. Thereafter
the reaction medium is stirred to a period of up to 2 hours in order to ensure complete reaction.

The reaction is preferably carried out in the absence of a solvent although an inert so7vent may be added if desired.
Aliphatic hydrocarbons and chlorinated hydrocarbons may be employed as solvents.

The reaction product rapidly settles into an acid layer and an organic layer which may be separated. The acid layer comprises the catalyst and may be recycled for use
with another reaction batch. A further advantage of this invention is that the separated acid can be repeatedly recycled without losing its e cacy or contaminating the
product in any way. Also the acid is recovered in almost quantitative amounts (99~) even after repeated recycling~ whereas when mixtures of sulphuric and an organic
acid are used signi cant quantities ( 5%) of the acid separate into the organic phase and are lost during the puri cation thereof.

The separated organic phase is conveniently worked up e.g. by washing with dilute alkali and water. The components thereof can be separated by fractional distillation. In
general three main product fractions can be identi ed. The lowest boiling comprises the dimeric materials formed from the alkene, the second (boiling at 70-lloC at 6mm
Hg) the indanes and precursors thereof and the highest boiling the dimeric materials formed from the styrene.

The most valuable fraction is the second. It will usually comprise a mixture of at least two indanes even when the process has been carried out using a single styrene and
a single alkene. The use of mixtures of alkenes or styrenes as starting material(s) usually leads to the formation of a product containing a more complex mixture of
indanes.
The second products fraction may be separated into its component chemicals but, more usually, where the indanes are for use as a chemical intermediate, this product is
used directly withouyt any separation.
The products of the precesses of our invention nd [articular application as intermediates in the synthesis of certain isochromans such as are described in Britsh Patent
No 991,146 and which nd use as ingredients of compunded perfumery composition. They may, therefore, be reacted with an alkylene oxide in the presence of an
electrophilic catalyst and subsequently with formuldehyde to yield such isochromans, using the tecniques described in aforesaid British Patent No. 991,146 or those
described in Britsh Patents Nos.
1,219,046, 1,452,049 and 1,524,076 and published European Patent Application No. 0004914. The use of th4 mixture of compounds obtained leads to the production of a
mixture of isochromans which mixture has an attrative odour and may be used as an ingredient of compounded perfumery compositions. We have discovered that in the
course of this sythesis of the isochromans from the indanes which form part of the second product fravton vertain of the other components of that product fraction are
converted to the desired isochromans. Thus, procedures using the unseparated second prodcut frqction obataine by fraction dis-tillation represent a preferred as[ec of
out invention.
The preferred indane products of out invention are those having the aforesaid formula wherein both R1 and R2 represents methyl goups, the most preferred being tyhose
wherein both R4 and R5 also represent methyl groups. The most preferred indane is the compound having the aforesaid formula wherein R3 represents a methyl group.
The most preferred styrene for present use is .alpha.-methyl styrene, i.e. the compound of the above formula wherein R1 represents a 36i~L~

methyl group. I'ne preferred al~enes for presert use are 2 methyl-but-l-ene, 2 methyl-but-2-ene and isobutylene.

The processes of our invention f;nd particular 2ppl ication to the reaction between ~-methyl styrene and a 2-methyl butene, 5 especially 2-methyl-2-butene (or tertiary
amyl alcohol). Such a ?rocess is preferably carried ou~ by adding equimolar quantities of the reactants to from 1.0 to 5.0 moles,preferably from 1.0 to 3.0 or most
preferably 1.5 to 2.0 moles,of 90% w/w phosphoric acid and ma;ntaining the reaction medium at the temperature of from 0to 50C or more preferably ~rom 25 to 30C. The
pro~uct o~ such a reaction has been found to comprise a mixture of the indane having the formula:

i.e. wherein R1, R2, R3 and R4 and 25 represent methyl 15 groups which compound is commonly termed pentamethylindan and an indane having the formula:

i.e. wherein R1, R2 and R4 represents methyl groups and R5 represents an ethyl group and R3 represents a hydrogen atom which 20 is (1,1, 3-trimethyl-3-ethyl) indane.

The product of this reaction has been discovered to comprise at least two chemicals whch are adducts of the butenes and styrene which are useful as intermediates in
the synthesis of isochromans by ~r~

~iL936~L~

virtue of the fact that they appear to cyclise to form indanes and subsequently to be converted to isochromans. The compounds in question are 2,3,4-trimethyl-4- phenyl-
pent-l~ene and 2,4-dim~thyl-2-phenyl-hex-4-ene (cis and trans isomers thereof) i.e. the compounds having the formulae:

3 ~ , and ~ / )1 These compounds are believed to be novel and constitute another aspect of our invention.

The invention is illus~rated by the following examples:-EXAMP!E 1 A mixture of~-methylstyrene 1 (345, 3 moles) and commercial grade 2-methylbut-2-ene 2 containing
85~ 2 methylbut-2-ene, 8~o 2 methylbut-1-ene and 77O C5 alkanes (2109, 3 moles) was added over 3.75 hours to 90~ w/w ortho phosphoric acid (5199, 4.8 moles as
100%
phosphoric ac;d) 3 at 25-27C. Stirring was continued for a further 2 hours. The mixture was allowed to separate when 5119 of the acid was recovered. ~e organic layer
was washed successively with water (75g), 57~ sodium hydroxide solution (2059) and water (75g). The resu1tant oil (547g) was distilled under vacuum to give 0 3 main
fractions:-w/w yields Butene dimers b.p. 38-40/llmm Hg lO~o Indanes and precursors b.p. 70-100G/6mm Hg 63~o ~-methyl sytrene dimers b.p. 114 140/2mm Hg 19%

36~L0 G.l.C. analysis (9-10' SP 2100 at 180C) of the second fraction gave the following individual yields of components .

1,1,2,3,3 - penta methylindane 55.5%

1,1,3 - trimethyl-3-ethyl indane 4.0~
Indane precursors 3.5%

1 99% pure by GLC supplied by the Koch-Light Company 2 as supplied by Shell (Holland) 3 SLR grade (S.G 1.75) as supplied by the Fisons Company Ltd.

A mixture of -methyl styrene (3499) and commercial grade 2-methylbut-2-ene as used in Example 1 (2079) was added over 3.75 hour to the acid recovered from Example
1 (5119) at 25-27C. Stirring was continued for a further 2 hours. The organic layer was separated, washed and distilled as in Example 1 to give a 63.5~ w/w yield of

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indanes and precursors.

EXAMPLE 3 - Example of multiple Recycle of Phosphoric Acid A mixture of -methylstyrene (2369) and commercial grade 2-methylbutene-2, as used in Example 1, (140g)
was added over 4 hours to 90% w/w ortho phosphoric acid (3469) at 25-30C. Stirring was continued for a further 2 hours. After the two phases had separated out 95% by
volume of the top (organic) phase was sucked off and washed separately (as in Example 1). A fresh mixture of c~
methylstyrene (2369) and 2-methylbutene -2 (1409) was then added to the same phosphoric acid under identical condi~ions used for the rst batch. This oil was sucked
off and washed and a further six charges of mixed reagent feed were added to the phosphoric acid.
At the end of the eighth batch 3459 of orthophosphoric acid was recovered. (99.7% recovery).

3L ~ 3 6 ~

The washed oil phases were combined to give 29489 of crude product which was distilled as in Example 1. 1950g of indanes and precursors (b.p. 70-110/6mm Hg) or
6470 ~/w yield were recovered.

Patent Citations (11)

Publication number Priority date Publication date Assignee Title

Family To Family Citations

GB796130A * 1953-10-09 1958-06-04 Polak Frutal Works Polyalkylindanes and process for manufacturing the same

GB796129A * 1953-10-09 1958-06-04 Polak Frutal Works Polyalkylindane derivatives and process for manufacturing the same

US2851501A * 1954-10-05 1958-09-09 Polak Frutal Works Production of poly alkyl indanes from styrene compounds

US3151174A * 1961-05-02 1964-09-29 Givaudan Corp 1, 1-dimethyl tetrahydronaphthindans and process for preparing
same

GB991146A * 1962-07-23 1965-05-05 Int Flavors & Fragrances Inc New tricyclic isochromans with musk odour

US3347946A * 1966-02-17 1967-10-17 Givaudan Corp Derivatives of hydrindacene and process for preparing same

US3532719A * 1968-10-28 1970-10-06 Int Flavors & Fragrances Inc Process for production of isochromans

US3751500A * 1969-08-18 1973-08-07 Int Flavors & Fragrances Inc Hydrogenated indane derivatives and processes for producing same

JPS5610891B2 * 1974-11-21 1981-03-11

US4265818A * 1979-08-03 1981-05-05 International Flavors & Fragrances Indane alkanols and tricyclic isochromans and organoleptic uses
Inc. thereof

US4308412A * 1979-08-03 1981-12-29 International Flavors & Fragrances Indane alkanols and tricyclic isochromans and organoleptic uses
Inc. thereof

* Cited by examiner, † Cited by third party

Cited By (4)

Publication number Priority date Publication date Assignee Title

Family To Family Citations

US4596896A * 1985-06-03 1986-06-24 Phillips Petroleum Company Acid catalyzed reactions of monovinyl aromatic compounds

US5034562A * 1990-06-08 1991-07-23 Phillips Petroleum Company Acid-sulfolance catalyzed production of cyclic alkylated compounds

US20110077440A1 * 2009-09-28 2011-03-31 Adeniyi Lawal Process for Producing Alkyl Substituted Indanes

CN103772119A * 2012-10-26 2014-05-07 国际香料和香精公司 1,1,2,3,3-pentamethyl-indan and preparation method thereof

* Cited by examiner, † Cited by third party, ‡ Family to family citation

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Priority And Related Applications

Priority Applications (2)

Application Priority date Filing date Title

GB8108050 1981-03-13

GB8108050 1981-03-13

Legal Events

Date Code Title Description

2002-09-17 MKEX Expiry

Concepts

machine-extracted Download Filter table

Name Image Sections Count Query match

manufacturing process title,claims,abstract,description 8 0.000

indanes title,abstract,description 18 0.000

chemical reactions claims,abstract,description 31 0.000

phosphoric acid claims,abstract,description 27 0.000

HO
O
P
HO
OH

phosphoric acid claims,abstract,description 27 0.000

aluminium phosphate claims,abstract,description 24 0.000

alkenes claims,abstract,description 20 0.000

styrene claims,abstract,description 19 0.000

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9/24/2020 CA1193610A - Production of indanes - Google Patents

products claims,abstract,description 17 0.000

catalysts claims,abstract,description 15 0.000

alkyl group claims,abstract,description 4 0.000

isochromane claims,abstract 2 0.000

O

methods claims,description 26 0.000

methyl group claims,description 22 0.000

mixtures claims,description 22 0.000

acids claims,description 20 0.000

Indane claims,description 12 0.000

2-Methyl-2-butene claims,description 10 0.000

compounds claims,description 9 0.000

hydrogen atoms claims,description 9 0.000

* H

precursors claims,description 8 0.000

reactants claims,description 8 0.000

Protein Precursors claims,description 7 0.000

Protein Precursors claims,description 7 0.000

aqueous solutions claims,description 6 0.000

layers claims,description 5 0.000

acid catalysts claims,description 4 0.000

carbon atoms claims,description 4 0.000

isobutene claims,description 4 0.000

organic layers claims,description 4 0.000

alkylene oxide claims,description 3 0.000

chemical reaction products claims,description 3 0.000

fractional distillation claims,description 3 0.000

2-methylpent-2-ene claims,description 2 0.000

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ethyl group claims,description 2 0.000

propylene group claims,description 2 0.000

*:1
*:2

2,3,4-trimethylpent-4-en-2-ylbenzene claims 3 0.000

2,4-dimethylhex-4-en-2-ylbenzene claims 3 0.000

2-methylbut-1-ene claims 2 0.000

2,4,4-trimethylpent-1-ene claims 1 0.000

2-methylpent-1-ene claims 1 0.000

3-methylbut-1-ene claims 1 0.000

formaldehyde claims 1 0.000

formaldehyde claims 1 0.000

intermediates abstract,description 6 0.000

styrenes abstract,description 3 0.000

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