Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/38—Polysiloxanes modified by chemical after-treatment
  • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
  • C08G77/398—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
  • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
  • C07F15/0086—Platinum compounds
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
  • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
  • B01J31/123—Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain
  • B01J31/124—Silicones or siloxanes or comprising such units
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
  • C07B47/00—Formation or introduction of functional groups not provided for in groups C07B39/00 - C07B45/00
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0803—Compounds with Si-C or Si-Si linkages
  • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
  • C07F7/0827—Syntheses with formation of a Si-C bond
  • C07F7/0829—Hydrosilylation reactions
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
  • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
  • B01J2231/32—Addition reactions to C=C or C-C triple bonds
  • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
  • B01J2531/82—Metals of the platinum group
  • B01J2531/828—Platinum
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/06—Preparatory processes
  • C08G77/08—Preparatory processes characterised by the catalysts used

Definitions

• a process forms a platinum organosiloxane complex, which is useful as a hydrosilylation reaction catalyst. More particularly, the process is robust and produces a platinum organosiloxane complex with lowered reaction processing time to achieve good yield regardless of the quality of starting materials as compared to previous methods.
• One method for preparing a platinum organosiloxane complex includes concurrently combining a platinous halide, a polar organic liquid and an organosiloxane having silicon bonded organic groups with terminal olefinic unsaturation under conditions to react the platinous halide with the organosiloxane.
• This method may lack robustness in that various factors, such as crystallite size and/or quality of the platinous halide can lower the yield of platinum organosiloxane complex.
• a process can be used to form a product comprising a platinum
• organosiloxane complex comprising:
• R1 to R10 are each independently selected from hydrogen, an alkyl group having from 1 to 6 carbon atoms, and a phenyl group, or any two of R1 to R10 may combine to form one or more carbocyclic groups; with the proviso that when R1 is methyl and one of R2 and R3 is hydrogen and the other of R2 and R3 is methyl, and R5 and R6 are both hydrogen; then R4 is not methyl; and
• the process described herein forms a product comprising a platinum organosiloxane complex, which is useful as a hydrosilylation reaction catalyst.
• the process comprises:
• R1 to R10 are each independently selected from hydrogen, an alkyl group having from 1 to 6 carbon atoms, or a phenyl group, or where any two of R1 to R10 may combine to form one or more cyclic groups; with the proviso that when R1 is methyl and one of R2 and R3 is hydrogen and the other of R2 and R3 is methyl, and R5 and R6 are both hydrogen; then R4 is not methyl; and
• the process may further comprise:
• the process may further comprise step 4) adding E) an additional polyorganosiloxane to the reaction mixture and/or the neutralized reaction product during and/or after step 2).
• Step 1 ) of the process described above may be performed at ambient or elevated temperature.
• the starting materials may be combined at room temperature of 25°C.
• the starting materials may be combined with heating, up to a temperature that does not degrade the platinous halide selected as starting material A) and/or that does not remove too much of the ketone selected as starting material B) and/or that does not remove too much of the enone additive selected as starting material C) and that does not degrade the platinum organosiloxane complex.
• the starting materials may be combined by mixing at 25°C to 90°C.
• Step 1 may be performed by heating the starting materials for at least 8 hours at a temperature of 30°C or less, e.g., 25°C to 30°C.
• step 1 ) may be performed by heating the starting materials for 1 to 8 hours at a temperature of 55°C to 90°C, alternatively 2 to 5 hours at a temperature of 85°C.
• Starting materials A), B), C) and D) may be combined in any order.
• starting materials B), C) and D) may be combined to form a mixture, and thereafter the mixture and starting material A) may be combined in step 1 ).
• the process may further comprise milling A) the platinous halide in the presence of B) the ketone before and/or during step 1 ).
• step 1 ) may be performed by milling A) the platinous halide in the presence of C) the enone additive before adding B) the ketone.
• the process may further comprising milling A) the platinous halide in the presence of B) the ketone and C) the enone additive before and/or during step 1 ).
• Milling may be performed by any convenient means, such as adding inert particles, such as glass beads, to a container containing the starting materials in step 1 ) and subjecting the container to rolling or agitation. Milling may be performed at ambient or elevated temperatures, such as the temperatures described above for step 1 ).
• Step 1 ) of the process produces a reaction mixture.
• Step 2) of the process described herein comprises neutralizing the reaction mixture formed in step 1 ).
• Neutralizing the mixture may be accomplished by mixing the reaction product with a hydrocarbon solvent, such as heptane, toluene, or xylene and a basic buffer solution at elevated temperature.
• a hydrocarbon solvent such as heptane, toluene, or xylene
• the exact temperature selected for step 2) depends on various factors including the volatility of the ketone selected for starting material B), however, step 2) may be performed at 40°C to 50°C.
• the buffer solution comprises deionized water and a salt such as sodium bicarbonate, calcium carbonate, magnesium oxide, or magnesium carbonate.
• the buffer solution comprises sodium bicarbonate.
• the platinum organosiloxane complex may be recovered from the neutralized reaction product formed in step 2) by any convenient means, such as filtering, stripping and/or distillation. Pressure may be reduced to facilitate removal one or more starting materials and/or by-products.
• step 1 it is not necessary to dry the starting materials before their use in this process, however, drying one or more of the starting materials may be performed as an additional step before step 1 ).
• step 1 is performed in the absence of added water.
• the reaction mixture may be stripped and/or distilled to remove excess water, ketone, enone additive, and/or excess polyorganosiloxane. Pressure may be reduced to facilitate removal one or more starting materials and/or by-products.
• reaction mixture may be filtered after step 1 ) and before step 2) to remove unreacted solids and/or solid by-products, and/or inert particles used for milling, if any.
• Starting material A) used in the process described above is a platinous halide.
• the platinous halide has general formula Pt a X , where subscript a is 1 to 6 and subscript b is 2 to 12.
• Each X is independently a halogen atom, such as Br, CI, F or I; alternatively Br, CI or F; alternatively Br or CI; and alternatively CI.
• the particle size and/or crystallite size of starting material A) is not critical.
• Starting material A) may include an impurity, for example, starting material A) may contain up to 10% of zero valent platinum (Pt ⁇ ). Alternatively, starting material A) may contain up to 5%, alternatively up to 0.6%, and alternatively up to 0.3% of zero valent platinum (PtO). Alternatively, starting material A) may contain 0.3% to 1 %, and alternatively 0.3% to
• platinous halides 0.6% of zero valent platinum (Pt ⁇ ).
• suitable platinous halides for starting material A) include platinum dichloride of formula ⁇ - ⁇ 2- Platinous halides, such as platinum dichloride are commercially available from Heraeus, Johnson Matthey, or Sigma Aldrich.
• Starting material B) is a ketone.
• the ketone may have 4 to 8 carbon atoms.
• Starting material B) may be acetone and/or methyl ethyl ketone.
• starting material B) may be methyl ethyl ketone.
• Starting material B) may be used in an amount of 1 to 20 moles of ketone per mole of platinous halide.
• Starting material C) is an enone additive included in the process in step 1 ).
• the enone additive is in addition to the other starting materials, and in addition to any enone compound that may form by rearrangement/reaction of the ketone selected for starting material B).
• the enone additive for starting material C) may be distinct from any compound formed by rearrangement/reaction of the ketone and/or the enone additive may be an additional amount of a compound that is the same as a
• the enone additive is a compound of formula (I) and/or formula (II), where
• R1 to R10 are each independently selected from hydrogen, an alkyl group having from 1 to 6 carbon atoms, and a phenyl group, or any two of R1 to R10 may combine to form one or more cyclic groups; with the proviso that when R1 is methyl and one of R2 and R3 is hydrogen and the other of R2 and R3 is methyl, and R5 and R6 are both hydrogen; then R4 is not methyl.
• each of R1 to R10 is independently selected from H and a methyl group.
• one of R5 and R6 is hydrogen and the other of R5 and R6 is an alkyl group, such as methyl.
• the enone additive may have 4 to 20 carbon atoms.
• R1 and R2 may combine to form a carbocyclic group.
• R4 and R6 may combine to form a carbocyclic group.
• both R1 and R2, and R4 and R6, may combine to form carbocyclic groups.
• Suitable enone additives include (C1 ) (4E)-3-4-Dimethyl-4-hexen-2-one; (C2) (5E)-5- Methyl-5-hepten-3-one; (C3) 4-Penten-2-one; (C4) 3-Methyl-4-penten-2-one; (C5) 4- Methyl-4-penten-2-one; (C6) 3,3-Dimethyl-4-penten-2-one; (C7) 3,3,4-Trimethyl-4- penten-2-one; (C8) (4Z)-3,4-Dimethyl-4-hexen-2-one; (C9) 2-(1 - cyclohexenyl)cyclohexanone (commercially available from Alfa Aesar); (C10) 3-Buten-2- one (commercially available from Aldrich); (C1 1 ) (3E)-3-Penten-2-one (commercially available from Aldrich); (C12) (3E)-3-Methyl-3-penten-2-one (commercially available from
• the enone additive may be selected from the group consisting of (C3), (C4), (C5), (C6), (C7), (C8), (C9), (C10), (C1 1 ), (C12), (C13), and two or more of C3), (C4), (C5), (C6), (C7), (C8), (C9), (C10), (C1 1 ), (C12), and (C13).
• Suitable enone additives of formula (I) include (C1 ), (C2), (C3), (C4), (C5), (C6), (C7), (C8), and (C9).
• Suitable enone additives of formula (II) include (C10), (C1 1 ), (C12), and (C13).
• Starting material C) may be used in an amount 0.1 % to 50%, alternatively 1 % to 10%, and alternatively 1 % to 5%, based on combined weights of liquid starting materials used in step 1 ) (e.g., starting materials B),
• Starting material D) is a polyorganosiloxane having, per molecule, 2 to 4 silicon bonded terminally unsaturated hydrocarbon groups having from 2 to 6 carbon atoms and any remaining silicon bonded organic groups being monovalent hydrocarbon groups of 1 to 12 carbon atoms.
• unsaturated groups include alkenyl groups such as vinyl, allyl, butenyl, and/or hexenyl, alternatively vinyl or alkynyl groups such as propynyl and/or butynyl.
• the remaining silicon bonded organic groups in the polyorganosiloxane may be alkyl, aryl, and/or phenyl groups.
• Alkyl groups are exemplified by methyl, ethyl, propyl and butyl; alternatively methyl or ethyl; and alternatively methyl.
• polyorganosiloxane may be linear, branched, cyclic or resinous; alternatively linear or cyclic; alternatively resinous; and alternatively linear.
• the polyorganosiloxane may be, for example, a vinyl terminated polydimethylsiloxane, methyl-vinyl cyclotetrasiloxane, trimethylsiloxy-terminated (dimethylsiloxane/methylvinylsiloxane) copolymer, and/or (dimethylsiloxane/methylvinylphenylsiloxane) copolymer. Specific examples include 1 ,3- divinyl tetramethyldisiloxane.
• the polyorganosiloxane may have unsaturated groups present on adjacent silicon atoms. Resinous polyorganosiloxanes suitable for starting material C) may comprise unit formula:
• each R1 1 is independently a monovalent hydrocarbon group of 1 to 12 carbon atoms (as described above), each R 1 2 is independently a terminally unsaturated hydrocarbon group (as described above), subscript v ⁇ 0, subscript w is 1 to 3, subscript x ⁇ 0, subscript y > 0, and subscript z > 0.
• subscript x is 0 to 200
• subscript y is 1 to 202
• subscript z is 1 to 100.
• each R 1 1 is a methyl or phenyl group and each
• R 1 2 is a vinyl group.
• the resinous polyorganosiloxane may contain an average of 3 to 30 mole percent of unsaturated groups, alternatively 0.1 to 30 mole percent, alternatively 0.1 to 5 mole percent, alternatively 3 to 100 mole percent.
• the mole percent of unsaturated groups is the ratio of the number of moles of unsaturated group-containing siloxane units in the resinous polyorganosiloxane to the total number of moles of siloxane units in the resinous polyorganosiloxane, multiplied by 100.
• resinous polyorganosiloxanes are known in the art.
• resinous polyorganosiloxane may be prepared by treating a resin copolymer produced by the silica hydrosol capping process of Daudt, et al. with at least an alkenyl- containing endblocking reagent.
• the method of Daudt et al. is disclosed in U.S. Patent 2,676,182.
• the method of Daudt, et al. involves reacting a silica hydrosol under acidic conditions with a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof, and recovering a copolymer having M-units and Q-units.
• a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof.
• the resulting copolymers may contain from 2 to 5 percent by weight of hydroxyl groups.
• the polyorganosiloxane may be used in an amount of at least 3.5 moles of polyorganosiloxane per mole of platinous halide, alternatively 3.5 moles to 150 moles of polyorganosiloxane per mole of platinous halide, alternatively 3.5 moles to 130 moles of polyorganosiloxane per mole of platinous halide, alternatively 3.5 moles to 20 moles of polyorganosiloxane per mole of platinous halide; alternatively 5 moles to 15 moles of polyorganosiloxane per mole of platinous halide.
• Starting material E) is an additional polyorganosiloxane, other than the polyorganosiloxane selected for starting material D).
• the additional polyorganosiloxane may be added in an amount up to 25% based on weight of the reaction mixture formed in step 1 ) of the process described above.
• Starting material E) may be an additional amount of a polyorganosiloxane selected as starting material D).
• starting material E) may be a non-functional polyorganosiloxane, such as trimethylsiloxy- terminated polydimethylsiloxane.
• a mixture of a non-functional polyorganosiloxane such as trimethylsiloxy- terminated polydimethylsiloxane.
• a mixture of a non-functional polyorganosiloxane such as trimethylsiloxy- terminated polydimethylsiloxane.
• a mixture of a non-functional polyorganosiloxane such as trimethylsiloxy- terminated polydi
• starting material E polyorganosiloxane and an additional amount of a polyorganosiloxane selected as starting material D) may be used as starting material E).
• Starting material E when present, may be used in an amount up to 25% based on weight of all starting materials.
• Enone Additive L3, 4-Penten-2-one was prepared as follows. To a suspension of PCC (16.2 g) in 25 mL of dichloromethane was added penten-4-ol (5.1 mL) in 5 mL of dichloromethane at room temperature. After addition, the mixture was stirred at room temperature for 3 hours, then 50 mL of diethyl ether was added. Black tar rapidly formed on the bottom of the flask. The liquid phase was separated, and the black tar was washed with diethyl ether (20 mL x 3).
• Examples 1 - 1 1 and Comparative Examples 1 and 2 were prepared using the following general experimental procedure. A mixture containing ⁇ 3 ⁇ 4 (1 g), MEK (5 g),
• Examples 1 - 1 1 and Comparative Examples 1 and 2 were prepared using the general procedure above. The enone additive, reaction time, and yield are shown below in Table 2.
• a 100 mL flask was assembled (no grease) with a 12" water-jacketed reflux column, a thermocouple, a turbidity probe, a magnetic stirbar and a heating mantle, blanketed with nitrogen.
• 0.3g of an enone additive was mixed with 9.9g MEK and 19.8g DVTMDS. This 30g solution (containing 1 wt% enone) was added to 2.0g PtCI2 in the flask.
• the contents of the flask were stirred and heated to 85°C, making sure not to overshoot by more than 2°C.
• the contents of the flask were then refluxed with water cooling on the column.
• Example 15 and Comparative Examples 5 and 6 were prepared as in examples 12-14 and comparative examples 3 and 4, respectively, using a different batch of PtCI2. Yield was calculated as described above, but after different amounts of time.
• Examples 12 to 15 and Comparative Examples 3-6 show that adding an enone additive can improve yield with the same or shorter processing time as compared to a process with the same conditions except that the enone additive is omitted.
• Comparative Example 3 shows the reaction mixture took 14 hours to reach 98.4% yield, but adding 1 % of enone additive L5 in example 12 shortened reaction time to 1 1 hours to reach 98.7% yield.
• Enone additives L9 and L3 provided further benefits in that even shorter reaction times achieved the same or higher yield as in Comparative Example 3, as shown in Examples 13 and 14.
• Example 15 shows that adding enone additive L3 improved yield in 4 hours to 98.8% as compared to only 91 .7% yield achieved under the same conditions but without the enone additive in Comparative Example 6.
• the present process is robust in that quality of the platinous halide selected for starting material A) is not critical to achieve the yields of the present process.
• the platinous halide useful as starting material A) may contain up to 10% zero valent platinum (PtO) without expectation of a detrimental effect on yield achieved with the present process.
• the yield of the present process is not dependent upon particle size and/or crystallite size of the platinous halide selected for starting material A), as may have been required for previous processes.
• disclosure of a range of, for example, 2.0 to 4.0 includes the subsets of, for example, 2.1 to 3.5, 2.3 to 3.4, 2.6 to 3.7, and 3.8 to 4.0, as well as any other subset subsumed in the range.
• disclosure of Markush groups includes the entire group and also any individual members and subgroups subsumed therein.
• disclosure of the Markush group a hydrogen atom, an alkyl group, an alkenyl group, or an aryl group includes the member alkyl individually; the subgroup alkyl and aryl; and any other individual member and subgroup subsumed therein.
• Alkyl means an acyclic, branched or unbranched, saturated monovalent hydrocarbon group.
• alkyl groups include methyl, ethyl, propyl, 1 - methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, 1 -methylbutyl, 1 - ethylpropyl, pentyl, 2-methylbutyl, 3-methylbutyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, heptyl, 2-ethylhexyl, octyl, nonyl, and decyl; and as well as other branched saturated monovalent hydrocarbon groups with 6 or more carbon atoms.
• Alkyl groups have at least one carbon atom.
• alkyl groups may have 1 to 12 carbon atoms, alternatively 1 to 10 carbon atoms, alternatively 1 to 6 carbon atoms, alternatively 1 to 4 carbon atoms, alternatively 1 to 2 carbon atoms, and alternatively 1 carbon atom.
• Alkenyl means an acyclic, branched, or unbranched monovalent hydrocarbon group, where the monovalent hydrocarbon group has a double bond.
• Alkenyl groups include ethenyl, allyl, propenyl, butenyl, and hexenyl. Alkenyl groups have at least 2 carbon atoms. Alternatively, alkenyl groups may have 2 to 12 carbon atoms,
• Alkynyl means an acyclic, branched, or unbranched monovalent hydrocarbon group, where the monovalent hydrocarbon group has a triple bond.
• Alkynyl groups include ethynyl, propynyl, and butynyl. Alkynyl groups have at least 2 carbon atoms. Alternatively, alkynyl groups may have 2 to 12 carbon atoms, alternatively 2 to 10 carbon atoms, alternatively 2 to 6 carbon atoms, alternatively 2 to 4 carbon atoms, and alternatively 2 carbon atoms.
• Aryl means a hydrocarbon group derived from an arene by removal of a hydrogen atom from a ring carbon atom.
• Aryl is exemplified by, but not limited to, phenyl and naphthyl.
• Aryl groups have at least 5 carbon atoms.
• Monocyclic aryl groups may have 5 to 9 carbon atoms, alternatively 6 to 7 carbon atoms, and alternatively 6 carbon atoms.
• Polycyclic aryl groups may have 10 to 17 carbon atoms, alternatively 10 to 14 carbon atoms, and alternatively 12 to 14 carbon atoms.
• Carbocycle and “carbocyclic” refer to a hydrocarbon ring. Carbocycles may be monocyclic or polycyclic, e.g., bicyclic or with more than two rings. Bicyclic
• carbocycles may be fused, bridged, or spiro polycyclic rings.
• Carbocycles have at least 3 carbon atoms.
• Monocyclic carbocycles may have 3 to 9 carbon atoms, alternatively 4 to 7 carbon atoms, and alternatively 5 to 6 carbon atoms.
• Polycyclic carbocycles may have 7 to 17 carbon atoms, alternatively 7 to 14 carbon atoms, and alternatively 9 to 10 carbon atoms.
• Carbocycles may be saturated ⁇ e.g., cyclopentane or cyclohexane), partially unsaturated ⁇ e.g., cyclopentene or cyclohexene), or fully unsaturated ⁇ e.g., cyclopentadiene or cycloheptatriene).
• Cycloalkyi refers to a saturated hydrocarbon group including a carbocycle. Cycloalkyi groups are exemplified by cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl. Cycloalkyi groups have at least 3 carbon atoms.
• Monocyclic cycloalkyi groups may have 3 to 9 carbon atoms, alternatively 4 to 7 carbon atoms, and alternatively 5 to 6 carbon atoms.
• Polycyclic cycloalkyi groups may have 7 to 17 carbon atoms, alternatively 7 to 14 carbon atoms, and alternatively 9 to 10 carbon atoms.

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